An Escort's Journal

Chapters

First-timers
Every-now-and-thens
Regulars
Stocking up
Odd Requests
Refusing Service
Days Off
Basics
Threesomes
Inter-escort Relationships
Escort-client Relationships
Friends
Lovers
Making the Rules
Breaking the Rules
Confessions
Clients that aren't Clients
Dating a Client
Charity
Couples
Letting Loose
Angry Spouses
Changes of Role
Home
Family
Unpredictable Ponies
Impossible Ponies

First-timers

Chapter 1

First-Timers.

Dear Journal,

I awoke this morning to the tinny ring of my cheap alarm clock hammering at my senses, shaking me from slumber with its angry shriek. In a semi-conscious daze I managed to get my hoof onto the switch, and rolled myself out of bed, my bed to be precise not the bed. I blearily searched my small, sparsely furnished room. No decorations colored the walls here, not in this room. This room was my vacation from the rest of my life, and certainly the rest of my house. All that was in here was a single bed, one dresser, and a bedside table topped with my two-bit alarm clock.

I trudged over to my dresser, still barely awake, and let my hooves find my reading glasses. I popped them and grabbed my small black appointment ledger. The cover bore no title or image, only black pleather and little gold corners. With practiced ease I flipped over to today. An appointment awaited me: 3 o’ clock, anonymous. “Terrific,” I groaned to myself “another first-timer.”

First-times usually make anonymous appointments. Sometimes it’s because they’re not sure if they want to go through with it, and leave themselves a little safety barrier. Other times, they just prefer I know as little about them as possible.

I remember, when I received this particular appointment. I found the letter in my mailbox, free of any address, stamp, or name. The letter itself, on the other hoof, was positively loaded with ink. There was a lot of “If it isn't too much trouble” and “If you please”s and endless formality within.

I shook my head, rattling free the negative thoughts in my brain as best I could. It would do no good to head into a meeting with a brand new client with a head full of preconceptions. That’s a good way to lose perfectly good business. I trotted down the hall toward the bathroom. There was much personal maintenance to be done. I examined my reflection in the full body mirror that sat across from my shower. My fetlocks needed to be shorn, my hooves filed a bit, my mane was... fine... for now, but a trim would be needed soon. My coat, definitely needed a good brushing, and lastly, my scruff needed to be shaved.

I sighed, dreading the ordeal. Most ponies would find it silly, going through all this self-beautifying hassle. But hey, no one wants to make a second appointment with a slovenly, unkempt pony; and I’d be damned if I let myself lose a single precious customer just because I was too tired to shave that morning. Not that some ponies don’t like a little scruff; I just like to make a good, clean first impression.

I stepped into my shower, big enough for two ponies, and turned the cold valve. I read somewhere that cold showers are good for you, they help with circulation, help you wake up, and shivering helps burn calories, apparently. All I was thinking about, however, was how much I desperately wished that I did not know that, so that I might have continued to take nice, pleasant, warm showers in blissful ignorance.

After the rather lengthy procedure of getting myself (and the bathroom) neat and tidy, I took a glance examined my reflection once more, to see the face and body that my clients expect of me. Handsome devil.

I made my way downstairs into the main room of my two story cottage, and began my routine inspection, to make sure nothing was even an inch out of place. Two large, comfortable cushions sat opposite each other, sandwiching a small wooden table complete with two white tea cups, and a tea kettle atop a decorative trivet. Across the room from the small arrangement stood my fireplace, a small marble hearth decorated with ivy (the plastic kind) and filled with enough wood to get a roaring fire burning. The rest of the room was dotted with carefully placed decorative throw pillows and candles. Everything was absolutely perfect.

I grinned to myself, and walked into my kitchenette to make some breakfast. I poured myself a nice big bowl of breakfast cereal. I know that a guy who takes as much care of his body as I do probably shouldn't start the day with something almost entirely marshmallows, but hey who’s perfect. I happily chewed into the sugary blobs. A glance at the clock told me that this was, in fact, lunch; because 2:30 was far too late for breakfast. 'Wait a second, 2:30?'

“Shit.” I quietly swore, as I began to wolf down my cereal like a prison inmate. I had only 30 minutes to finish my breakf… lunch, tidy the kitchen, and get dressed. I know a lot of ponies talk about getting dressed like it’s easy, and there is a very good reason for them to believe that.

They are unicorns.

I would like to make something perfectly clear, putting on clothes without the telekinetic aid of magic is, and pardon my language, a fucking chore. Hooves and mouth alone make the task of changing pretty difficult. Even wings would be nice, I've seen pegasi use those babies with amazing levels or precision, if fact just two weeks ago a lovely client… never mind.

Now, while I’m fully aware that it’s socially acceptable to not wear clothes in public, especially in this rural setting, I like to wear clothes. I’m from Manehattan, and a lot more ponies wear clothes there. That, and I feel that the addition of jeans to my image makes me a bit more mysterious; mystery gets ponies talking, which gets them interested.

Where was I? Oh yes, getting dressed. After I wriggled my way into my signature blue jeans, (a task I feel I have adequately covered the difficulty of,) I made my way back downstairs with only moments to spare. I watched the large clock in the main room tick over to 3 o’ clock. Right as I was about to sit myself down onto one of the green cushions, there was a faint knock at the door. That’s another first-timer habit, they always knock quietly, hoping I won’t hear, so they can just turn around and say ‘oh well, guess he’s not home.’

I quickly jogged to the door, and prepared my act. My eyes half lidded themselves into a sultry gaze, my face plastered itself into my practiced ‘pleasant grin,’ and I cleared my throat, preparing for what could potentially be hours of suave baritone.

Okay, maybe it’s more of a tenor.

I slid open the door coming face to face with my client. She was purple, lavender really, her mane a sort of deep indigo. A duo of stripes, pink and purple ran down one side of her bangs, just past her horn. Her face was a mix of nervous and embarrassed; she was blushing almost up to her ears. The moment her gaze met mine it shot to her hooves, which raked nervously against the brick stoop of my home. She was adorable.

“H-H-Hi…” was all she managed to get out before an almost tangible wave of embarrassment swelled up her face.

“Hello, miss.” My voice slid into its sultry cadence, if only just so. This wasn't the time to lay it on thick. “Please, come in…” I slid back, as she stepped into my home. As she walked past, I caught a glimpse of her cutie mark: a pink starburst fringed with smaller white stars. An astronomer maybe? “Take a seat, please, and I’ll put the kettle on.” She obliged, legs folding under her as she got comfortable on a cushion. I grabbed the kettle and trotted off to my little kitchenette. I like to take my time when I do this, give the client a chance to acclimate, take in the surroundings. It puts them at ease.

After a few minutes, I returned, and took the seat opposite her. “Do you have a preference for tea? I've got quite a selection,” I recited.

Her words came as a whirlwind, flying out of her mouth in nervous flurries. “Oh none for me thanks, I think right now stimulants would only exacerbate my already tremendous amounts of nervous energy!” She stated very matter-of-factly despite her panic. Big on words, this one.

I stopped myself from rolling my eyes. I tried to meet her gaze only to find hers staring dead at my table. “I should say so.” I chuckled. “Well, let’s get started shall we?”

“Oh, right now? As in, right now right now?” Her eyes began to dart every which way around the room. “Because I’m not ready, I mean I only just got here and I thought I’d have a few minutes or so to prepare myself and...”

“Calm down.” I cut her off as gently as I could. “I only meant let’s get started talking, there’s some things to discuss before we do anything.” I put on a reassuring smile, and she relaxed a bit. “Firstly, I have a question.” She gulped; she didn't know what to expect. First-timers never do. “What should I call you? You can use your name, or anything, really. But I can’t go around calling you ‘you,’ now can I?”

She blinked, and her hoof met her chin in contemplation. She pondered for a while. A less-experienced pony of my profession might be tempted to hurry her along, but two very important facts keep me from ever rushing a client. First, in my line of work you never want to rush anypony, this is the sort of thing that needs to be done at their pace. Second, I’m hourly, why would I ever hurry anything?

She finally spoke up, looking me straight in the eye for the first time. “My name is Twilight.” She said, with only slight waver in her voice. She smiled nervously.

“Very well,” I smiled back at her. “It’s a pleasure to meet you Twilight. Now there are a few more questions I’d like to ask, if that’s alright.” She nodded. “Firstly there’s the matter of *ahem*…” I adjusted my position slightly to appear nervous. I wasn't really nervous, but seeing me a little nervous tends to calm ponies down. It’s all part of the act. “…payment. You never mentioned in your letter how much time you were planning on spending here.”

“Oh!” she piped up, her voice the calmest I’d heard it yet. “I didn't think of that.” She pondered once more. “Um… how long do ponies usually take to… I mean, do you charge just for the time when you’re…” she trailed off, as her blush crept back into her face.

“I start charging from the moment you walk in the door, and I stop charging when you leave. I’m sorry if there was any confusion.” I adjusted myself again, okay, maybe I was nervous. I never like telling ponies they owe me money. ‘But hey business is business,’ I told myself. “My price will be 20 bits an hour, starting from 3 o’ clock.”

“Oh… okay um… I guess I’ll pay for 3 hours. What happens if I run over?” Her nervousness was picking back up. I had to rein her in fast, or this mare was going to escalate into full meltdown.

“How about I just collect at the end, and charge you for the time you used, sound good?”

“O-Okay, that sounds fine.” Her bout of nerves passed; and she began to glance about the room. “You have a lovely home, must be nice living here… but it’s so far from Ponyville.” Finally, she was easing into casual conversation.

“Well, thank you, I do love living here…” Well, not here here, I live upstairs, but she didn't need to know that. “And as for it being far, that’s... uh... not really by choice. There are a number of ponies who prefer that my... entrepreneurial escapades, shall we say, be kept far out of Ponyville proper.”

“Really? Why?” She inquired, genuinely curious.

“Well I’m sure it’s just because many ponies don’t agree with my profession. But the official reason is so that no children accidentally wander in and be horribly traumatized, or something along those lines.” I concluded with a sigh. “Well enough about me, I’m more interested in you.” I playfully smirked. “One thing I’m curious about. How did you hear about me?”

I took a moment for her to realize I was asking her a question, until she gasped in realization. “Oh, um, from a friend.” She grinned wide, hoping that would suffice.

“Everypony knows everypony in Ponyville.” I smirked right back. I made a small bridge with my hooves and delicately rested my chin on them. “I want to know which friend. If you don’t want to tell me their name, that’s fine, but could you maybe describe them.”

Her eyes closed, and she took a deep breath. “Her name is Rarity.” She said with calm resolve. This mare was proving to be a lot more confident than I took her for.

“Oh, Rarity?” I couldn't help but laugh. Close to half of my clientele is referred by her.

“What’s so funny?” There was a sort of innocent curiosity about the way she said that.

“Oh, I just get a lot of clients from her.” I reined in my outburst. “Well, all that’s left is the big question.” She gulped. “What can I…” I motioned toward myself with a hoof and swung it around to point at her “…do for you?” Normally I would lay it on thick with my 'what-I-really-wish-was-low-enough-to-be-baritone,’ but something told me that this unicorn is just a little too smart for that, so instead I adopted a tone similar to her own, one of genuine inquiry and wonder. I did my best to appear curious.

“Oh well…” She swallowed hard again. Just as she opened her mouth to speak again, the air began to fill with the rising whistle of the tea kettle.

“Hold that thought.” I raised myself off the cushion and cantered into the kitchen. I quickly scooped a half-measure of tea leaves into the kettle. As I stepped back into the living room, kettle in mouth, I came to a sudden realization. 'Oh, HAY, I forgot to put on music.' One thing you learn in my profession, is that if things are going well, you don’t go out of your way to change them. Now, music serves a number of purposes, it’s a conversation topic, and the right music can certainly set the right mood, but above all, music makes the awkward silences that much less awkward, which is why, it really sucked that I didn't have any. The issue was, if I started the music then, it would have looked like I was trying to set up a certain mood, much more so than if it had been playing from the beginning. Clients, new clients especially, hate feeling like they’re being nudged into anything. Even the mares who like being tied up need to be in control.

But hey I’m a perfectionist, things were probably going to be fine… probably.

I returned to the table, placing the kettle on the trivet. I sat back down on my little cushion. “I made it a bit weak just in case you wanted some.”

“Oh... thanks…” Her face found its way to the table once more. This time it seemed to be depression, not nerves.

“Something wrong?” I inquire.

“No… It’s just… it feels weird… paying for…”

“You, Miss Twilight, are paying for somepony's valuable time and nothing more.” I cut her off. I really wasn't planning on doing that, but this is a point of pride for me. “As a matter of fact, I have had a number of jobs wherein my client and I only chatted.” I announced proudly. It wasn't exactly a large number, but it was a number.

“You mean… we don’t have to have sex?” I just shook my head and smiled.

“Well that certainly simplifies things.” She gave a relieved sigh.

My face became one of confusion. “Well I guess that brings me back to my question… what can I do for you, Miss Twilight?”

She reddened again, but only slightly. “Well, Mister… Oh my gosh.” Her pupils shrank. “I... I don’t even know your name!” ‘She’s about to start freaking out again, isn't she.’ “Oh my gosh, and I call myself a student of friendship?! Some friend I am…” ‘Yes, Yes she is.’ She stood up, and began pacing about the room in a nervous tizzy ranting to herself about being sent to the moon or something. I knew I had to stop this nervousness once and for all.

I walked right up to her and looked her in the eyes. “My name…” My voice was even and low. Her gaze snapped to meet mine, tears starting to form in her eyes, and breath heavy with panic. “… is Guilty Pleasure, and I am an Escort. It is my job to make you happy, and to be your friend. You cannot disappoint me, you cannot offend me, and I will never ever judge you for anything you say or do in this house.” Her face became one of contented calm, hopefully for good this time. “So don’t worry so much.” I threw on my very best, ‘I understand, everything is going to be okay, award winning, hunky smile.’ She just stared up at me, for a bit, almost in awe. She opened her mouth to speak, I expected something along the lines of ‘thank you for being so understanding, you've really put me at ease.’

“I wanna watch you masturbate.” she said bluntly.

“Um… okay.” I was not prepared for that. “any particular reason? Not that I mind... at all!” I stammered. That one had taken me off guard.

“Well…” her whole temperament had pulled a 180°, and suddenly she was acting like she’d been coming here for years. “… I met this Stallion, and he’s really nice. I haven’t asked him out yet, but I want to. The thing is, I've never had… any real contact with the opposite sex.” She took her seat once again and magically poured herself a cup of tea, and a cup for me as well. Her magic had a beautiful hue to it, purple and pink, almost like the stripes that ran through her mane.

I sat opposite her once more. “Go on.” Finally I was getting somewhere.

“Well I was talking with Rarity…” She took a swig from her cup “… oh wow that really is weak.” She interrupted herself, scowling at her cup. “Anyways, Rarity said that I should just go for it and ask him out. So I said, I wasn't sure and I’d never dated a guy, and we got to talking and she kind of helped me figure out why I was so nervous about it. I’d never even seen a guy’s thingy before.” ‘Thingy... adorable’ She finished off her cup, and set it down. “So Rarity told me about you, and what you do. She said you were well-mannered and considerate.”

“Well I like to think I am.” I harrumphed softly and took a sip from my own cup. She was right it was far too weak, even if I had meant it. “So if I understand this, you want to ask a guy out, but not without understanding his... biology? Can I ask why? Are you planning on going that far on the first date?” I took another sip. “Not that that’s bad or anything.” I hastily added.

“Well, I guess I was, I mean... if he wants to and everything.” She murmured.

“Not that it’s really my place, Miss Twilight…”

“Please…” She smiled “Just Twilight.”

I grinned back at her, I take a certain pride in getting a client comfortable enough to be casual. “Certainly, Twilight, but if I may...” She nodded. “You should not be having sex before you are ready.”

“But what if he wants to?” she inquired.

“Simple…” I stated “Say ‘no.’”

“I couldn't do that, what if he never talks to me again because of that!?” She sounded almost angry at me for even suggesting such an outrageous course of action.

“Then he was never worth your time to begin with,” I say flatly. “Trust me.” She seemed to accept that. After only a moment, she stood up, “Okay then, Now w-w-why don’t we get those pants off of you.” She was blushing again, but she wasn't letting her embarrassment stop her.

I snickered like a schoolfilly, hearing her say that so nervously. I led her to the door opposite the kitchen, and into the bedroom, HER bedroom, not MY bedroom.

Stepping into the bedroom is quite an experience, especially for a first timer. Large trunks sit in various arrangements about the room, housing all manner of naughty apparatus, from ropes and handcuffs, to edible socks, to some stuff that I’m still not sure are even meant for ponies. Tall shelves line half of the walls, lined with potions and oils, books and scrolls. And, of course. what bedroom is complete without a bed.

The bed is easily the most expensive thing I own; perfectly round and free of any sort of headboard. The pillows are filled with real phoenix down; the comforter is stuffed with golden wool. But the mattress is where it really shines, a simple sheet wrapped around an enchanted cloud, the most comfortable thing I've ever had the pleasure of sleeping on.

Twilight, on the other hoof, was much more interested in the books. “ I've never even heard of half of these. Where did you get them?” She asked, stepping over to a rather sizable bookshelf. Her magic slid a small scroll off the shelf, and she began to peruse its rather graphic imagery, a blush once more creeping into her face, more from arousal than embarrassment, I assumed.

I trotted over to a smaller trunk, and pulled out a long fragrant stick of incense and a book of matches. “A lot are from a little antique shop I used to live near in Manehattan. Over the years I built up quite a collection.” I slid the lavender stick into a small holder beside the bed. “That’s a translated copy of the Camel Sutra, unabridged, by the way. Would you mind lighting this?” I indicated the incense.

“Huh? Oh, sure, no problem.” She quickly rolled the scroll up tightly, and magicked it back to its spot on the shelf. With a quick flash of her horn, the incense was suddenly lit, its pale smoke, wafting into the air and into my nostrils.

“Wow, so is that your special talent? Fire, I mean? I was just going to ask you to use one of these.” I briefly regarded the matchbook.

“Oh, no no no.” She turned, putting her cutie mark on display just for me. “My special talent is magic.” She smiled to herself, bringing a hoof to her chest in triumph.

Absolutely. Adorable.

“I didn't know magic could be a unicorn’s special talent. Wouldn't that just make you good at… everything?” I half asked half joked.

She scratched the back of her neck with a hoof. “Well I don’t like to brag or anything… oh WOW that smells good.” She regarded the smoldering stick of lavender just as a single burning cherry of ash fell onto the decorative wooden holder.

“I’m glad you like it, and if you’d like to borrow any of those books, just ask, I’ll let you know.” I grinned. I was actually enjoying talking to this mare; She was fairly comfortable with me for a first-timer.

“Thanks, but that might not be the best idea.” She sounded a little disappointed. “I would really love to, but I kind of… live with a kid a little young for that kind of stuff, and I’d really hate for him to stumble across it.” She sighed heavily. She clearly wanted to take something with her. An idea popped into my head right then, but I decided to give voice to it later, and see if I couldn't get some repeat business from this mare. But right now, I figured it was about time to get down to the deed.

“So shall we begin?” I queried, flopping down on my bed made of pure heaven.

“No time like the present.” She said, a smile almost free of worry adorning her face. Her magic rather suddenly extracted a pad of paper and pencil from her mane. “Do you mind if I take notes?”

I smiled back, and began to undo the button on my jeans. I could already feel myself hardening. “Go right on ahead, Twilight.” I giggled, delighting in her cute innocence once more. Fortunately for me, Undressing takes much less time than actually dressing. With a few careful motions, I slid my jeans down around my fetlocks, and playfully kicked them away. I looked back to Twilight. Her face was... confused. I wondered briefly precisely what she was expecting, until I noticed that her gaze was not directed toward my semi-firm stallionhood, but rather my flank. “Your cutie mark is a book?!” She almost yelled.

“Huh? Oh... Yes, yes it is.” Everyone asks that eventually, I just thought the little lavender mare might have more pressing priorities, like the ever expanding organ between my hind legs. “You want me to do this or…”

“What? Oh, yes of course, I just… a book?” She said perplexedly, “It just seems so…” she mused. “It doesn't fit. Wait, what is your special talent? I just assumed it was…. you know.” Her ears went flat as a sad ache crept into her voice.

‘Great, now she’s angry at herself for making assumptions… she REALLY needs to lighten up… Let’s see if I can’t distract her.’ I punctuated my interior monologue with a mischievous grin. I spread my legs wide toward her, as she looked despondently at the floor. “Twilight,” I softly called her name, adopting my ‘bedroom voice.’ Her eyes turned to me and immediately caught sight my now fully erect self. Her blush rocketed to new levels, turning even the tips of her ears red.

“Wow…” she mumbled. Her eyes transfixed on my stallionhood. “I knew they were supposed to get bigger but… oh my gosh.” Her hover pencil began scribbling furiously, but her attention seemed to be entirely on me.

“Just so you know…” I said, shifting my shoulders into a slightly more comfortable lean. “I’m actually a little on the small side.” I let hoof find its way up my shaft, gently tickling its sensitive surface.

“That’s… terrifying to think about,” she pondered. I fell into a rhythm of gently stroking myself, My skin stretching slightly with each pump. I watched Twilight as she stared at my little performance, her hips ever so slightly twitching as she stood, her tail slowly raising itself. Sadly from my position, I had no view of the sopping prize beneath. Her pencil and notepad scribbled furiously seemingly of their own accord.

I stopped my movements as I felt myself beginning to crest. As good with my hooves as I am, It certainly doesn’t take me that long to get people I’ve never met off, much less myself, and I felt no reason to end Twilight’s little show so soon. I raised myself from the bed and began to walk past Twilight over to one of the shelves across the room. I made sure to raise my tail, just enough to make myself visible, should she decide to turn around and catch a glimpse. I snatched a bottle off of the shelf, and turned back to the bed, Twilight’s face asked the obvious question before her lips even could.

“What’s that?” came her inquiry, eyes locked on something other than my cock.

“It’s honey-lemon oil. It’s my favorite.” I smiled as I appreciated the small, half-full carafe of pale yellow fluid. “It smells absolutely wonderful, especially with the lavender.” I grabbed the small glass stopper in my teeth as I took my spot on the bed once more. I poured a small dribble of the fluid onto my free hoof, and bent myself down to place the bottle on the floor.

My newly oiled hoof took a firm grasp of my flesh and began pumping with renewed vigor. The familiar warming sensation of the oil seeped its way into me as the delicious honey-lavender -lemon smell permeated the air. After minutes of grunting and the slapping noises of wet flesh, I felt myself approaching the point of no return.

“I’m going to finish soon,” I breathed. “Where do you want it?” My hoof began to stroke faster than ever.

“Want what?” I imagine she would have reddened further if such a thing were possible.

“My come, Twilight. Where do you want me to come?” I managed to hold myself off long enough to make sure I had time to hear her answer.

“I don’t know… anywhere!” she shouted, her voice fraught with alarm and confusion.

‘I may as well give her a show.’ I took hold of myself, and aimed upwards across the room. Climax filled my senses as my testes clenched tight, and ribbons of sticky jism cascaded a short way across the room. The spent seed splattered unceremoniously onto the wooden floor a yard away from my seat, and the only sound that filled the room was my blissful panting. I collapsed against the bed, forelegs sore and breath heavy. It took some effort to even speak.

“That… *huff*…*huff*… felt good.” I laughed heartily as I sat myself up. “I really should do that more often.” I cast a lazy glance at Twilight, who appeared to be stunned into silence, staring at the sticky clear splotches on the floor, her pencil and paper dead in the air. “So what did you think?”

“That…” she continued to stare at the floor “… was interesting.” She looked back to face me; her hovering notepad snapped shut, and quickly found its way back into her mane. Her expression was... troubled? She noticed my look of concern. “I don’t know it all just seems very… hard?”

“Well it does tend to get pretty firm…,” I teased. She glared at me a bit. “…but that’s not what you meant.” I did my best to be supportive, and help her sort out all the new information she’d learned. “Sex can be… exhausting, but it’s really worth it. At least in my opinion it is.” I stood myself up, and stepped over to another chest in the corner of the room. I picked a white towel out of it and walked over to the mess I’d left on a large portion of my floor.

“Worth it how? It seems like a whole lot of work, for only a few moments of payoff.” She looked skeptical, and that look caused something to suddenly click for me.

“Oh my gosh, you've never had an orgasm have you?” I asked without thinking, as I began to meticulously wipe my spunk off of the hard wood.

“What?! Of course not! I've never had sex!” She looked almost hurt, as though I’d made some terrible accusation against her personage.

“Well we didn't have sex, and I just came.” I offered, confident she’d pick up the implication.

“But I've never… how could I… It’s so… girls don’t do that!” She was on the defensive yet again… something was really eating at her, I could tell.

“Twilight, I have extensive firsthand experience, that tells me that girls can, and do, masturbate…” I countered. I finished wiping up, only to notice another mess on the floor, a mess that did not belong to me. “…and by the looks of things you could really afford to rub one out, as well.” I regarded a small clear puddle on the floor, directly beneath where Twilight’s hind legs.

Twilight followed my gaze, and twisted her face into one of shocked horror, as she realized precisely what she was looking at.

“Oh no no no no no no…” she frantically shook her head. “I don’t… I know I’m not going to have sex so why…?”

“Because you’re aroused,” I stated. “It happens.”

“But it’s not supposed to just happen!” she looked pleadingly in my eyes, wanting me to somehow make it better, to make everything okay. So, that’s exactly what I did.

“Twilight, you don’t think you’re capable of controlling when you’re aroused do you? Because If anyone in all of Ponyville could do that, It would be me. With all my experience, all of my practice, and all of my sheer force of will... I still get stiffies when I don’t want them.” I walked up and placed my hoof… my clean hoof… on her shoulder. “There’s no shame in being horny for no reason.”

“You’re sure?” She had tears in her eyes now, I only saw them briefly before her face was thrust into my shoulder, and she began bawling. I had figured something out about poor Twilight. She had thought she was a ‘bad girl’ for getting aroused, and without an outlet she only got more and more horny, which in turn only made her feel worse and worse. It was tragic... adorably tragic... but tragic.

Her head pulled away from my shoulder as bawling gave way to sobs, which in turn gave way to quiet sniffs. “Sorry,” she laughed despite herself, eyes puffy and wet.

“What did I say earlier? No judgment.” I smiled. “Now, how about this. I am going to teach you, Twilight, how to pleasure yourself, because you are in desperate need of a way to blow off some steam.”

“What? But, if all goes well, soon I won’t need to. I mean, If I end up with a boyfriend, why would I need to blow off steam?” She looked at me quizzically. “I always heard that boys want it all the time, so I should be in the clear right?”

I rolled my eyes. “You’d be surprised, I wouldn't be at all shocked if this guy couldn't keep up with you. Even so, sometimes you’ll rather just jerk it than have sex.”

“Okay, but don’t say ‘jerk it.’” she laughed, as I led her to yet another on the chests in my room.

“These, Twilight…” I pause for effect as I lifted the lid, displaying its contents within. Several plastic toys of varying length and girth, arranged in a foam display casing sat inconspicuously in the box. “… are vibrators,” I stated as reassuringly as I could. She immediately began examining one of the larger specimens: a great big, veiny, black monster of a dildo.

“Oh my Gosh, It’s enormous!” She giggled for a while before hovering it back into its slot. She then removed a small pink egg vibrator, and gave the switch an exploratory flip. The little egg hummed to life in the air, and she giggled once more.

“That one is probably more your speed. Come, sit on the bed.” She trotted over to the bed, vibrating egg in telekinetic tow. She tentatively sat the bed, and gave the mattress a scrutinizing.

“This is really comfy, what is it?”

“Uhh, it’s enchanted cumulus,” I explained.

Her eyes went wide. “Wait, you mean this is a cloud, but how come we can touch it? I mean, I know a spell to make a pony walk on clouds, but not one that makes a cloud solid for all ponies. How do they do it?” Her eager smile beamed at me.

I shrugged. “Oh man, heck if I know, I know nothing about magic.”

She prodded the cloud bed with a hoof. “It’s fascinating.”

I chuckled. “I’m glad you like it. Shall we begin?”

She blushed once more, and nodded her head with conviction. She gulped audibly. “Um we can start but, I don’t want you to see anything.” She crossed her legs defensively.

‘Damn,’ I lamented internally. “No problem, Twilight, let me just grab a cushion from the living room.” I quickly fetched a cushion and placed it between the bed and the door. I sat, facing away from Twilight. “How’s that?”

“No peaking!” I could practically hear her blush.

“No peaking, Twilight,” I reassured her. “Now let’s do it like this: I’ll direct you from here, and if anything makes you uncomfortable you let me know.”

“O-Okay,” she said.

“Okay, now I want to lie back and take a deep breath.”

“Okay.” I heard the sound of sheets ruffling under her coat, followed by a long heavy breath.

“Now I want you to spreeeaaad your hind legs,” I kept my voice as gentle as I could, scaring this far in could set her back miles.

“O-Okay,” she complied… or at least I assumed she did.

“Is the toy still on?”

“It’s on!” I don’t think she meant to yell, but she was starting to panic.

“Calm down, Twilight, For now I want you to turn it off, can you do that?”

“Sure.” I heard the quiet click of the toys switch being set into an off position.

“Okay, now we’re going to get a little more serious. If you’re comfortable, I want you to take hoof, and reach slowly down between your hind legs.” There was no response this time, but the faint sound of rustling fur told me she had complied. “Now I just want you to touch yourself, don’t try to stimulate yourself yet, just get familiar with the area.” I cleared my throat slightly. “Now one thing I want you to keep in mind is that there is nothing to be ashamed of here. Whether they’re public about it or not, lots of ponies masturbate, and it’s perfectly natural and normal.” I felt a little bit like an X-rated after school special, my speech was a little generic, but it got the point across. “Now if you don’t mind me asking, how do you feel?”

Her response came after a long pause, “It kind of… tickles, I guess. I’m still all w-wet from… you know… watching you.” I could hear her breathing become excited and heavy. “I like it so far.”

“That’s good, now I want you to find something you do that feels especially good, and keep doing it, go as fast and firm as you’re okay with.” An almost soundless schlicking noise started to rise in the room, as well as an occasional blissful whimper. “Feel good?” I asked.

“Y-y-y-yeah,” came her pleasure laden response.

“Now I just want you to keep at it for a while, I’ll be here, just let me know if you need anything, or if something feels wrong.” I figured the odds of that were very low, but anything to comfort my client.

Minutes passed and the pace of her movement began to pick up, and her moans became long and throaty. I could tell she was really getting into it… as was I. I could feel myself getting hard in my seat.

I’ll be honest. I wanted very badly to mount her then and there, to rush over and teach her all kinds of pleasure. That said, I have standards, I was here to help her as best I could with what she wanted, not what I wanted. I was not about to seduce a mare who had plans of asking out some lucky… very lucky… stallion with hopes of starting something meaningful. I’m not the kind of stallion who does that kind of thing… at least not anymore.

Eventually she spoke up, voice panting and drunk on pleasure. “I think… *huff*… I’m ready to try… *huff*… something more… *huff*… advanced.” Her newly broken-in hooves had apparently brought her as close to orgasm as they could at present. I wasn't worried, I was sure that before long, she’d be able to get off with the best of them.

“Okay Twilight, now do you see that bottle of oil from Earlier?” I asked.

Shifting fabric preceded her response. “Yeah.”

“I’d like you to pour a little out onto your hoof, and rub it on the egg.” My own need for satisfaction was becoming unbearable; if I didn't do something about it I was going to lose all sanity. “On an unrelated note, I’d like to ask your permission for something.”

“What is it? Did I do something wrong?”

I answered before she had a chance to panic. “No, Twilight, I just have a request. I’m getting very aroused, and I was wondering if you would mind if I pleasured myself as well.” A response came in the form of the small crystal bottle of oil levitating over to me. ‘She wasn't kidding about her special talent’ I mused ‘that’s quite some range for a pleasure drunk unicorn.’

I doled myself out a small portion of oil and took grip of my stallionhood. A small gasp came from the mare. “This stuff gets warm.”

“Sorry, I should have warned you… does it feel okay?” I really hoped I hadn't messed up with that one.

“Yeah, it’s okay… a little weird, but okay,” she responded. “So now what?”

“I want you to turn on the toy, it’s only got one setting, and put it wherever feels best, a lot of mare like it right at the top of their lips, there’s a little nub…”

“I know what a clitoris is,” she deadpanned. The buzzing of the toy hummed through the silence, when suddenly Twilight let forth a far from quiet moan of ecstacy. “Aaah!” The buzzing continued and I could hear Twilight kicking at the sheets, I could tell this wouldn't take long.

Breathing, kicking, panting, the furious shlicking noises, everything began to escalate to climax, for both her and myself. The smell of wanting mare filled my nostrils and tipped me over the edge. Hot cum sputtered out of me. nowhere near the force of earlier, dribbling out onto my chest and down my ever-shrinking shaft.

Just as the wave of my orgasm began to pass, I could her Twilight’s crest. “AAAAAAAAAOOOOOOHCELESTIATHATFEELSGOOOOOOOOOOOOD!” Her screaming continued for what could easily have been half a minute, until finally I heard her collapse.

I let her stew in her own pleasure for a while, before finally saying something. “So…?”

“Okay... definitely, definitely, definitely, worth it.” I could practically hear her smile.

“Why don’t you collect yourself and we’ll…”

“Oh my gosh... Oh no no no no!”

‘Sweet Luna what is it this time?’ “What happened, are you okay?”

“I’m sorry, I’m sorry, I’m sorry! I just… it felt so good, I….”

“Can I turn around? Are you decent?” I asked, genuinely concerned, I was fairly certain it was no big deal, but she
needed reassuring, or else all of this work could end up bolstering any discomfort with sex.

“I’m decent but don’t turn around!” she shouted.

“What happened?” my voice was nothing but concern and worry. Tone of voice goes a long way, it can make the difference between a pony trusting you or not. I’m very good at getting ponies to trust me.

“Oh, please don’t be mad,” she fretted

“I won’t, now just tell me what happened,” I said, keeping frustration out of my voice completely.

“W-well, when I... um… came,” she whispered that word, “ I kind of… um…” she mumbled something I didn’t quite catch.

“What was that?”

“I… peed… a lot.” Her voice began to once more turn to tears.

“Oh, is that all?” I ask, my voice thick with relief.

“What do you mean is that all!? Something must be wrong with my vagina! How does this kind of thing even happen!?” I heard her hooves tapping the wood as she paced around the room in what had to have been her twentieth nervous tizzy of the evening.

“Well, I can’t attest to precisely how it happens, but I can tell you that it happens all the time,” I informed her.

“R-really?” she asked in hopeful desperation.

“Yes,” I reassured her. “Can I turn around now?”

“I guess.” She finally surrendered, and I turned around to survey the damage, well aware that no matter how bad it was, that I’d play it off like it was nothing. I took a glance at the puddle in the middle of the bed, it was pretty big, but nothing I haven’t seen before.

I let my face relax into one of calm reassurance. I looked to Twilight who stood as small as she could, eyes downcast, rubbing her fetlocks together is shame. “It’s not a big deal, Twilight. It’s not that uncommon.” Her face looked up at mine, the absolute picture of embarrassment. “In fact, It’s so ‘not-uncommon’ it has a name. It’s called ‘Stress Incontinence.’ The short version is that lots of stress, namely stimulation, makes you lose control of your bladder.

Her face began to relax, she seemed to like when I sounded like a textbook. “But, I made such a mess of your bed,” she half-cried, eyes stuck on her shameful splotch.

“Sheets can be washed; and the mattress is a cloud. Everything rains out of it.”

She was quiet for a long time. When I say quiet, I mean she didn't say anything; she was still sobbing a little. “Okay,” she finally managed.

“Now, I’ll worry about this. You’re probably going to want to shower or something; you can use the bathroom upstairs. You saw the stairs when you came in right?” I asked, already hard at work taking the sheets off the bed.

“Yeah,” she answered, clearly happy to have something else to think about.

“First door on the right, you’re welcome to any shampoo or anything in there… I got all kinds.” Twilight nodded, and left the bedroom quietly, still partially ashamed of herself. The smell of urine started to permeate the air as I carried the sheets into the hamper I keep in the closet. I sighed heavily, hopefully after a quick rinse Twilight would come downstairs and be satisfied with my services, and we could discuss future business.

I decided that rather than sit there and twiddle my hooves, a more productive thing to do would be to clean the semen out of my coat, put the cushion back where it belonged, and make some actually tasty tea. After that ordeal I was sure we could both use some. A quick rub down with a wet towel and I was good to go, and after a few minutes of preparation the kettle began to whistle, just as I heard Twilight make her way down the stairs.

‘Here’s the Moment of truth.’ “That has got to be the nicest bathroom I've ever seen. I didn't know anyone even made zap apple Shampoo.” Her smile positively beamed as she trotted past the kitchen. ‘Well, she’s happy at least, that’s a good sign.’

I cleared my throat. “So, Twilight, I must ask… were you happy with our little… show and tell?” I tried my very best not to sound desperate.

She took deep breath and smiled dreamily toward me. “More than happy, Mr. Pleasure, It was… you were… completely perfect.” I fight the urge to pump my hoof wildly. “You taught me so much and I really… I can’t thank you enough.”

“Let’s not go that far. I’m glad I could help, but I’m sure it wasn't that mind-blowing.” I motioned over to the table. “Why don’t we have a cup or two? I promise it’s good this time.”

She tittered as we both made our way to the table. Twilight poured tea into the two cups as we took our seats. “So, would you say you’re all ready to ask out your hopefully-special-somepony?” I took a deep swig of the tea, thankfully it was good.

“I would have to say, Mr. Pleasure, that I believe I am.” Her pride practically poured out of her.

“Please,” I corrected her. “Just Guilty.”

“Okay, Guilty. So, uh…” she glanced curiously at me. “What happens now?” It was her turn to drink, a smiling glance at the tea told me she approved.

“I’m glad you asked. One thing I would like to discuss, if I may be so bold, Is the prospect of repeat business.” I put down my teacup. “I know you plan on seeing someone, but that doesn’t mean your appointments need to stop. If you like, you can always come over for dating advice, should you feel your friends aren’t helping you.” It was time to enact the plan I’d been formulating since she first laid eyes on my collection of antique books. “However one thing I think we’d both enjoy is if got together for study sessions.” Her eyes absolutely lit up at the suggestion. “Well I could tell you liked my books but didn’t really feel safe taking them home, so if you like, we could get together for a little… reading party every so often… does that sound nice?” I finished my proposition, and finished my tea as well.

“That sounds… well, as a certain friend of mine would say… totally awesome.” She regarded her tea thoughtfully. “Orgasms too, they’re also totally awesome.” She polished off her cup as I laughed uproariously.

“I gotta say Twilight, It’s refreshing to have a client like you.” I reached to pour myself a second glass, but Twilight beat me to it, distributing tea into both cups.

“How do you mean?”

“Well…” I pondered a while, and tried to figure out precisely what I meant as well. Eventually I found the words. “Most ponies come to me, and they’re trying to escape. Some just need me for physical satisfaction; some just need someone to whine to. Occasionally ponies come in out of pure boredom, But all of them are just trying to get away from something or someone. But you… you came to me not for escape, but for help. You came to me, looking to better yourself. It’s…” I gazed into her eyes, and for the first time really noticed their hue, a vivid purple, just like the stripe in her mane. “…refreshing.”

She frowned. “That’s a sad way of looking at it.”

“Oh?” I confess I was curious to see where she was going with this.

“Those ponies that come to you… they need help to. They all have problems they need help with. Maybe they are using you as an escape, but maybe that’s what they need: an evening away from their problems, a vacation just for them.”

“Maybe you’re right, Twilight.” I looked at the clock; it read 5:12. Well unless you have anything you’d like to discuss…” I waited to see if she would interrupt me “… then I think we are done here. That was just over two hours, normally once we break into an hour I charge for it, but I’ll make an exception this time.” I winked at her. “So that will come to forty bits, Twilight. I hope you find the price acceptable.”

“That’s perfectly fine, guilty.” A coin purse levitated out of her mane, and forty bits counted itself onto my table.

“How much cool stuff can you fit into that mane?” I ask with a chuckle.

“Oh it’s just a spatial compression spell I've been working on. I've been messing around with the Hoofstein laws of spacial condensing to see if I can’t find a way to…”

“Aaaand you've lost me.” I stopped her for fear of my mind imploding.

She tittered again, and rose from her seat. “Well I need to get going, I have a letter to write.”

“Pen pal?” I ventured, standing as well.

“Something like that.” She made her way to the front door, and I walked her out.

“Good luck, Twilight”

“Thank you, Guilty.” She took four steps out the door before turning around.

“Oh, I almost forgot to ask… what is your special talent?”

“That, Twilight, is a secret.” I waved goodbye to her as she turned once more toward Ponyville. I was about to close the door when a rather strong gust of wind forced it back open. As I stumbled, I caught glimpse of Twilight. Her tail had been upturned by the gust, Providing me with a absolute perfect view of here tight marehood. The thing that caught my attention however was the small pink wire that connected her opening to a small equally pink remote nestled in her tail.

‘Oh well,’ I concluded, ‘she can keep the vibrator. I’m sure it will be very happy with its new owner.’ I closed the door to my home, and hefted my tired self upstairs. Twilight wasn't the only one in need of a shower. I spoiled myself with a nice, warm, sane shower.

As I write now, nestled back into MY bedroom, laundry done, dinner eaten, and house re-beautified, I find myself feeling rather satisfied with myself. I feel as though I've done a good deed breaking Twilight out of her little shell. I hope she and her stallion get along well.

Here it is! My First Fanfic! Criticism and comment welcome. Hope you enjoy.

Every-now-and-thens

Chapter 2

Every-now-and-thens

Dear Journal,

“5 o’ clock, Rarity,” I read aloud to myself. With a sigh, I quickly replaced my spectacles and my ledger, and made my way out of my bedroom. I made a mental checklist as I set about my practiced morning routine; there was much preparation to be done for the coming visit from Ponyville’s premiere fashionista.

The first order of business was styling my hair. Rarity was not looking for a visit with ‘ruggedly handsome’ Guilty. She was much more interested in a nice night in with ‘positively dashing’ Mr. Pleasure. Somewhere within the ordeal of brushing, and combing, and gelling, and styling, My mind began to wander. I wondered precisely what troubles were bringing Rarity to my door (and my bedroom) this time: a particularly bad date? An order bigger than she can handle? Whatever the case, I was sure I’d be hearing plenty about it.

I finished gussying up, tying off my mane in a ponytail with a dark blue ribbon; the top was styled nicely and cemented with gel. Happy with the results of my tedious grooming, I walked downstairs, moving on the next item on my checklist: the atmosphere. Easily the most lengthy and daunting task, setting up a suitable atmosphere is never exactly a fun thing to do. Most ponies think atmosphere only consists of candles and music; and while I will admit that soft melodies and mood lighting certainly work, there’s so much more that one can do.

I made sure that everything was clean, first of all; dusty floors are never really a turn on. I placed some fresh wood in the fireplace, ensuring a nice roaring fire would keep us warm long into the night. I put down a nice soft rug directly in front of the fireplace, in case anything too “active” happened before we made it to the bedroom. Just because one owns a sickeningly expensive enchanted bed does not mean one is always in it when the fun starts. I placed my table directly in the center of the room, a comfortable distance from the fireplace.

Okay fine maybe I did place some candles around and put some light piano on the gramophone; it’s a cliché for a reason. Lastly, I placed a pair of paper folding screens on either side of my little dining table. Successfully blocking the view of the kitchen and creating a secluded, little, private room. The stage was set, all that remained was the act.

Conversation with a client can be very tricky business. Sometimes clients don’t want to talk about anything at all, they just want to hit it and quit it. Other clients expect a little small talk, preferring to ease themselves into the more… adult… aspects of their session. Others come looking for advice (and sex). When someone comes to you for advice, it’s sort of a prerequisite that you are actually be able to give them any.

That said, if Rarity was having a fashion emergency, I would certainly need to be up to speed with any passing trends or fads in the fashion world. I pulled my latest issue of The Art of Fashion out of small pile of magazines I keep handy, and began my research.

I once had someone ask me, “If you do research like this for every client with a problem, wouldn’t that make you an expert in everything?”

“Of course not,” I responded. “It just means I seem like an expert in everything.”

The magazine was interesting enough, a couple of articles about the latest Canterlot style, an interview with Hoity Toity. It was more than enough ammunition for a couple hours of small talk. I checked the clock, 3:30, just enough time to get my best suit put on, and get a start on dinner. I never was one for formal attire, mostly because it takes forever to put on, but if a client expects a suit and tie, you wear it, or you lose a client. After a good hour of working my way into my modestly priced tux, I trotted into my kitchen and put on an apron.

Cooking is, of course, an art form, one for which I have much respect. Cooking while wearing a tuxedo, however, is a challenge. I worked carefully: pouring some canned sauce into a pot to simmer, getting some spaghetti noodles in boiling water, chopping a simple salad. I was well on my way to finishing up dinner when I heard the knock. I hurriedly flipped off my apron and answered the door.

She was stunning, she’s always stunning. She was wearing a thin black dress, it clung tight to her frame yet still managed to flow off of her. Her mane was, as it always was, styled perfectly; it cascaded down past her ears, yet retained a healthy bounce.

“Miss Rarity, a pleasure as always,” I practically crooned. For Rarity foreplay begins the moment she arrives, every word and line, every step and movement, all of it calculated and precise to make Rarity’s night in with me perfect. I knew I’d be keeping up the suave act for quite a while.

“Well,” her words came breathy and sultry, “If Mr. Pleasure himself says so, that must be the case,” she said, giggling slightly. I noticed her sapphire eyes catching fleeting glances at my attire, if she found any fault in my dress she made no mention.

“Please, come in. Dinner is almost ready,” I said, showing her inside. Her hips swayed heavily as she stepped inside. I have to admit I couldn’t help but stare.

It would have been rude not to.

She sat down at the table, her telekinetic grasp finding my issue of The Art of Fashion. She grinned coyly as she flipped through the pages. “Doing some research, I take it?”

‘Damn it!’ I scolded myself internally. ‘How did I forget the magazine?’ I’ll be the first to admit that I tend to micromanage meetings with clients, but there’s a good reason for it. When a client comes to me, they come expecting a certain level of quality, and with some clients that level comes very close to perfection. Still, even the greatest escort in history would never be able to create a truly perfect evening, so I have to take a ‘nice’ evening, and dress it up a bit. Illusion is a very big part of what I do, and it’s often what makes the difference between an escort and a whore. Knowing that small talk is hurriedly scrounged out of a magazine certainly breaks that illusion.

What I am trying to say, is that I had very suddenly been robbed of any ammunition I had had for this evening’s conversation.

“Just some light reading. Let me go finish dinner, it’s almost done.” I stepped briefly into the kitchen, just long enough to get the noodles onto plates and get some marinara on it. I returned to the dining room, with our food on a decorative silver tray.

“Oh spaghetti sounds absolutely perfect. I am positively famished,” she said, eyeing the pasta with hungry eyes. I quickly made one more trip to the kitchen, returning with a bottle of wine and two glasses.

“I’m glad,” I replied. “I do hope you find it to your satisfaction.” I snuggled myself into my cushion, across from my ‘date.’ My voice kept its very best high-society accent, as I poured each of us a glass of wine. “I say, Miss Rarity, You look more than stunning this evening,” I said as I raised my glass into the air. “To what shall we drink?”

Her glass raised itself, wrapped in a satiny, sky blue glow. “To my friend, Twilight,” she said with a mischievous grin, “and her new boyfriend, may they find luck in love.” I could already tell where she was going with this.

“To Twilight,” I mirrored, betraying nothing. Our glasses clinked together, and we both drank deep of the sweet spirits.

Rarity was the first to speak. “However I’m sure she won’t be needing any luck, what with all the sage wisdom she’s been receiving.” Her eyes looked knowingly at me, a smirk on her lips.

“And whose advice would that be?” I inquired innocently, raising a fork full of pasta to my mouth. ‘Well, thankfully the spaghetti’s good.’

“Come now, don’t play dumb, Guilty. Twilight’s told me all about her little visit.” She raised a fork of her own to her lips, daintily nibbling at the noodles.

“Miss Rarity, you know full well that I’ll neither confirm nor deny any sessions with any other pony.” Rarity always does that, she tries to eke whatever gossip she can out of me, hoping for something juicy. I never give her anything, of course, It’s a poor excuse for an escort that shares private information about his clients.

Even though she does this, it’s as much for her curiosity as it is for her peace of mind. After all, If I were to share anything about another client, who knows what I might share about her.

“Well, from what I hear, you’re even more of a gentlecolt than I would have ever imagined. Twilight just went on and on about how you were more polite and comforting than she could’ve ever dreamed.” She took another bite of spaghetti, and another, longer sip of wine. “So, tell me Guilty. How have you been?”

“Well I certainly can’t complain. Work’s been a bit slow lately, but it gives me more time to relax.” I sighed dramatically. “I just wish I had more clients like you, who appreciate proper romance.” It wasn’t entirely true, but that doesn’t mean Rarity doesn’t want it hear it.

“Like reading?” She teased, her tongue sticking out of her lips playfully.

I gasped mockingly, feigning offense at the gesture. “How positively unladylike,” I shot back. We both giggled for a while, until we slowly sank back into conversation. For a while we talked about her latest exploits in the world of fashion. Apparently she was making a killing off of some scarf craze that was sweeping Equestria. We also talked about her friends, Twilight included. I was glad to hear that she and her new boyfriend were getting along swimmingly.

As the sun dipped past the horizon I kindled the fireplace, sending a dancing orange glow across our private dining room. Rarity’s face was turning red from the wine, and her speech was ever-so-slightly slurred. I pretended not to notice. I was still trailing far behind her in terms of inebriation; getting too drunk was an easy way to get a case of ‘whiskey dick’. There are some tricks, though, to drinking without getting drunk. Refill your glass before it’s empty, always take your sip with a bite of something absorbent, like pasta, and if the setting permits, spill frequently.

“Oh, I do so enjoy these evenings with you Guilty,” she hummed, resting her head in her Forelegs. “Twilight wasn’t wrong about you, you know? You really are the picture of a gentlecolt.” She raised her head from the table, long enough to take another sip of wine. “So, tell me, any interesting clients lately?”

I chuckled playfully. “Wouldn’t you like to know?” , as I began to clear our empty plates from the table.

“Yes, very much so,” she laughed as I took our dinnerware back into the kitchen.

I returned to find Rarity staring longingly into the fire, her mind clearly miles away. She seemed not to notice my return, even as I took my seat once more. She sighed heavily as I poured her yet another glass.

“Is something the matter?” I asked.

“Hmmm?” she responded, oblivious to my question.

“Rarity?” I asked. She turned to me, her face flashing a hint of melancholy. “What’s the matter… something is bothering you.” I looked her straight in the eye. “Talk to Guilty.”

“Oh it’s just… It’s nothing…” she said, flustered.

“Rarity,” I deadpanned, “talk to Guilty.”

“Oh, I don’t know It’s just… *sigh*… I had a particularly bad evening recently,” she said. ‘Of course she did.’

I smiled a well- practiced, comforting smile, “Why don’t you tell me all about it?” I asked.

Her glass floated down to the table, free of its magical bonds. She stared into the flames once more. “Well, two weeks ago, I was asked out by a customer. He was sweet… charming… handsome… and well off to boot. He had come in for a suit; I ended up giving him… something plum I think. Anyways, on his way out the door he sort of… asked me to dinner.” She smiled in remembrance.

“The evening was… wonderful; We ate, we drank… we even danced. He was a real charmer… but when it was over… He… well… he didn’t want it to be.” She stared into her wine. “It was dreadful. He started yelling... made an absolute scene. He ended up waking up my neighbors. Can you believe it?”

“Oh, my goodness” I was flabbergasted. “Did you call the police?” I asked. I’ll admit my inner gossip was just eating this up.

“Indeed I did… but by the time they’d arrived he was… long gone.” She sighed.

“That sounds absolutely horrific, Rarity,” I spoke gently. “Allow me, if you will, to apologize on behalf of my gender.”

“Now, now... it’s not as though I’ve lost faith in stallion kind,” she divulged. “It’s just… Is that what ponies think of me? That I’m some… easy mare expected to put out on the first date. I always thought I looked like a lady, not like a…”

“…whore?” I offered.

The color drained from her face. “Oh no… Oh nonono, I didn’t mean it like that!”

“Relax Rarity… I’m just teasing,” I said, sticking my tongue out at her teasingly.

Rarity smiled briefly, only to sink her head into a pile of folded forelegs. “Do I, though?” Her voice came muffled through her limbs. “Do I… overdo it? Do I look like a whore?” She looked up at me pleadingly.

“Of course not, Rarity. Trust me, I would know,” I teased.

“I’m serious… Every day when I get up I spend hours plucking and styling and grooming…” ‘I know the feeling.’ “…and I do this… all of this, so that I come across as someone elegant, refined, and classy. It just feels like all my efforts make me seem…”

“…slutty?” I offered again.

Rarity frowned. “Stop finishing my… sennences.” ‘…and here comes the wine.’ Her eyes locked on to mine. “I’m nodda slut am I?” Tears began to well up in her eyes.

“Of course not dear,” I said, donning my most reassuring smile.

“Then why do all these stallions keep expecting me to *sniff* put out?” she sniffed.

Truth be told, I didn’t have an answer for her. There are any number of reasons a mare has a string of bad dates. Maybe she leads guys on without realizing it. Maybe she just has poor taste in guys. Whatever the case, what Rarity needed right now, more than ever, was to feel respected, and pampered.

“My dear, why don’t we lay down, you’re looking a little… tipsy,” I suggested.

“You might be right about that,” she admitted. Her half lidded gaze found my face. “I think I’d like to stay the night, dear. What does that cost again?”

“An extra fifty,” I divulged. Whenever a client stays the night, the pricing gets a little steep. I honestly do that to deter people. I prefer to sleep in my own bed.

We quickly made our way to the bedroom, bottle and glasses following in the best magical grip a half-drunk dress maker could muster. Rarity instantly dropped what she was holding and plopped down onto the silken sheets of the bed and I swiftly began lighting the myriad of candles that littered the room. I also made a quick stop at one of the many chests nearby, and pulled out a small phial of cloudy blue liquid. I pulled the cork out with my teeth and quickly down the potion. The all too familiar flavor of burnt hay and licorice briefly filled my mouth. Birth control potions don’t go down smooth, but they are necessary. After all, the last thing Rarity would want tonight was an unexpected pregnancy.

“Mmmmm, I always forget how wonderful this bed is.” She stretched herself lazily. “How does one even begin to afford such a luxury?” she asked, rolling across the mattress playfully.

“I’m not cheap, dear. You know that better than most I should say.” I smirked at her. She stuck hers out right back, and fell into a fit of giggles. She was most certainly drunk at this point. I was beginning to feel a little buzzed myself.

“Seriously though, I’ve seen what these things cost,” she asked with an eyebrow cocked. “,and I know what you cost.”

I never like questions that enter into my personal life.

“It was a gift… from a friend,” I quickly answered, desperately hoping that no follow-up questions would ensue.

“Nice to have friends with deep pockets,” she said, smiling. I joined her on the bed, and slid myself next to her prone frame. I wanted to change the subject quickly.

“Are you alright, dear?” I asked her smiling face.

Her eyes quickly adopted a sultry nature and she quickly licked her lips. “I will be, once you help me forget aaaaaall about it,” she went in for a quick kiss. My head jerked back with furious speed, deftly dodging her lips.

“Rarity…” I seethed. I did my best to keep from losing my temper, but one thing that most clients know is that kisses on the lips are off-limits. It’s a rule that Rarity tries to break occasionally, particularly when she’s depressed. “…you know the rules.”

“Oopsssssorry. I forgot,” she slurred as she smiled drunkenly. It looked like I could chalk this one up to the wine. “You juss looked so completely haaanssome.” Her face began to close in on mine again. For a second I was worried she would try to kiss me again, but when her cheek came alongside mine in an affectionate nuzzle, I relaxed. “I wish I could find a nice, dashing stallion like you… someone sweet and caring, who’s willing to go that extra step to make me sssmile,” she spoke just above a whisper into my ear. Her voice, if only for a while began to lose its formal cadence. She didn’t speak with any sort of pomp or elegance, she just sort of… spoke.

“Issa waste really… you could make sssome lucky mare very very happy.” She rolled onto her back and stared solemnly at the ceiling.

“But this way I can make lots of mares happy,” I said coyly.

“But issall just make-believe…” I was trying to make her laugh, but I think that only made her a little sad.

For a while nothing happened, we just lay in the candlelight quietly. Eventually she spoke up. “Guilty?” Her voice was filled with her high-society accent once more, and positively dripping with a musky allure.

“Hmm?” I brilliantly responded.

“Be a dear and fuck me, would you?” I’ve never been one for ‘dirty talk.’ Rarity, on the other hand, eats it up, so I oblige as best I can. ‘Alright, Guilty, time to let lose the almost-Baritone.’

“It would be my absolute pleasure, dear,” I crooned. She snickered slightly. I slid myself down between her haunches. I had a perfect view of everything. She was already soaking wet, her fur matted against her skin. My tongue gleefully dove into her tender pink flesh.

I absolutely love giving head, I would say it’s one of my favorite things to do to a mare behind bedroom doors.

I was greeted with the familiar sour flavor of mare, which swiftly washed the taste of birth control potion from my mouth. “Mmmmmmmmmmmm, you’re ssso good at that,” she hummed as my tongue probed her insides. I eagerly lapped up the taste of her arousal, brushing my lip against the tiny pink nub at the top of her lips.

“OOOH, Guilty, I think I’m already…!” Her hurried words were cut off and replaced with only silence as pleasure racked her brain. Her inner walls clenched around my tongue, as her hind legs squeezed my head. It hurt a little bit, actually. For a moment she was nothing but twitches and spasms. Eventually her facilities returned and she propped herself up to look down at me, still between her legs.

“How…*huff*… are you so… *huff*… good at that?” Her chest heaved as she spoke. I just smiled up at her, and gave her soaking vertical lips a quick peck. Her back instantly arched as she let out a breathy moan.

“More?” I offered.

“More!” was her reply, insistent and maybe a tad desperate. She remained propped up to look at me as I worked my magic on her nethers. Her tongue began to loll out of her mouth. I was tempted to say ‘How very un-ladylike!’ but speaking was not something I was in the… uh… position to do. Before too long, her walls took firm grip of my tongue once more, and an absolutely primal moan erupted from her mouth. “NNNNGGGGUUUUUUH!” She collapsed into a squirming pile of sweaty mare onto the cloud.

For minutes there was no movement save the rise and fall of Rarity’s chest. “Okay…” she spoke, “…new plan: find somepony…*huff*… half as good at that as you…*huff*… and marry him.”

I chuckled to myself. “Even if he’s an absolute slob?” I teased.

“Compleeeeeeeeeetely worth it!” she declared, smiling like a fool, staring hazily into nothing at particular.

I began to undo the buttons on my chest. Halfway down, I found my buttons enveloped by her magic. “Allow me, my dear,” she said as my shirt and tie began to remove themselves. Rarity’s own garb was soon caught in her magical field, and with a little squirming found its way onto the bedroom floor. The mare rolled onto all-fours, and turned away from me, and stuck her rear-end high into the air.

“Mount me, you sexy stallion, you,” she said. I had to do mental backflips not to break down in laughter at the pure corniness of the line.

“As you wish, my lady,” I said, just as corny. I slid across the surface of the bed and planted my hooves on her backside. I only then realized how hard I had become. I brought myself to her entrance and teased her moist folds.

“Just take me, already!” she begged, pushing her wanting sex into my own. I didn’t need to be told twice. I slid myself gently into her, reveling in the sensation on her marehood.

“OOOOOoooooh yeeeeeeeeeeeeeeeeeeeesss,” she moaned softly. After a few moments I began to pump in and out of her slowly. Each motion of my hips elicited a pleasured gasp from the fashionista. With each thrust, I buried my length inside of her, scraping myself against her insides.

“Is that good?” I teased as I thrusted away.

“It’s perfect… Don’t stop!” Her gasps began to run together into one continuous pleasured hum. I started to pick up my pace and made my strokes deeper, thrusting into her flesh. Our hips slapped together and slowly the intensity of the moment rose. Pleasure gave way to ecstasy , as I rhythmically pushed myself forward into the ivory mare again and again.

Eventually all of our toil and sweat paid off in glorious climax. I spilled into her as her walls gripped my rod with renewed force. For sweet seconds we both floated through a haze of pleasure, lost in our mutual orgasm. There were no screams or moans, no ‘Oh, Celestia!’ or ‘Sweet Luna!’ to punctuate our sweet relations. It was only candlelight and pleasure.

We collapsed into a pile of pony, nothing but spasms, and pants, and sweat bleeding into the sheets. I won’t say it was the best I’ve ever had, but it was definitely the best I’ve had with her. Rarity was the first to speak, her words slurred, drunk on wine and climax. “That was… *huff*… wonderful,” she sighed.

“I’m glad… *huff*… you think so.” I smiled at her as she lay there. Her face was still the picture of bliss: flushed and dreamy-eyed.

“You… *huff*… you really outdid… *huff*… yourself,” she said, her speech returning to her.

“Thanks… *huff*…” I untangled my limbs from hers and rolled onto my back, and I felt a dry sleepiness start to creep into my eyes. If I wasn’t careful I might fall asleep on her. Totally unprofessional.

“Mind if I smoke?” her voice shook me from my tired cloud.

“You know I don’t.” I heard the hum of magic and the sounds of a lighter. I stared upward for a while, and slowly trails of smoke began to billow up towards my ceiling. I love those moments: the moments between, ‘OH GOD YES’ and ‘let’s go again.’ For a few seconds it feels like there’s nothing on my plate, like there’s no job, no client, no nothing.

It’s nice.

“I must say, Guilty, that was, without a doubt, the best I’ve ever had.” She breathed a thick cloud of fumes into the air.

“I know what you mean… best for me in… quite some time,” I admitted.

“Oh?” she asked, I could hear the smile on her lips. “Now that’s a story I’d like to hear… ‘Guilty’s best.’” She really is a shameless gossip.

“Not going to happen, my dear,” I deadpanned.

“Oh, you’re no fun.” She took a drag of her cigarette, and daintily shook the ashes off, onto the floor. “You know, for all the time I spend over here, I don’t really know that much about you.” I didn’t like where this was going. “You never really… open up to me.” I really didn’t like where this was going.

“Why would I bother you with that? I’m here for you tonight, not the other way round.” I stole a glance at her as she puffed out smoke, like some kind of incredibly sexy chimney. She stared into space, her face a mask of concern.

“Well, be that as it may, that doesn’t mean I’m not willing to reciprocate.” Her gaze met mine. “I live to give, Guilty.”

“Well if you are, in fact, willing to reciprocate there’s something you could take care of for me,” I deflected, doing my best to showcase my ever expanding goods as subtly as possible. Anything to change the topic. Luckily, Rarity never turns down an opportunity to give head.

Rarity’s bedroom eyes kicked in again; she tittered. “Why Mr. Pleasure, it would be my… pleasure.” She slid around in front of me. She began to delicately rub her muzzle against the inside of my legs. Her breath tickled my loins, sending my member to full attention. I was honestly a little excited; Rarity is good at fellatio.

Her lips wrapped themselves around my rod rather suddenly. I gasped in surprise, my back arching slightly. Her tongue and lips played across me with practiced skill, lapping, and kissing, and sucking. By now she knows all my weak spots; she knows right where I liked it.

Soon I felt the entirety of my member slide deep into her throat. Did I mention Rarity is really good at fellatio? It was quick. It didn’t take long before I felt that familiar pressure build up and my loins started to clench. I exploded into her with potent force, her mouth eagerly accepting my load.

Her lips slid off of me, and I fell limp, letting out a satisfied sigh. The bed bounced slightly as Rarity hurried off the bed and, ultimately, left the room. Rarity never swallows. She says she’ll save that for the man she marries. We all have our reservations.

She returned moments later, cuddling up to my prone form, her head on my chest. “So... do I still ‘got it,’ as they say?” she asked.

“I should say so.” I quipped. She smiled up at me, looking proud. I could only grin. It was a short lived grin.

“Seriously though, you never tell me anything about you,” she whined, putting on a mask of mock hurt. Apparently a quick blowy was not enough to rattle this persistent mare’s memory. ‘Oh well, It was worth a shot… and I got head out of it.’

“I mean... For all the time I spend over here, all the things I tell you…” trailed off. ‘Okay Guilty...time to be serious.’

“Rarity, I don’t like talking to clients about my personal life,” I conceded.

“Well, that’s awfully rude, wouldn’t you say?” She was frowning at me now, anger brimming in her eyes.

I frowned right back. “How do you figure that?”

“Well it’s just… I tell you everything, Guilty… everything. It’s not too much to expect a little give and take is it?” She was starting to pout.

“Look, Rarity...” I did my best to look earnest. “I know... I know that I’m not exactly... forthcoming with my personal life. And the truth is... ninety percent of what I do, I do for my job, so there’s really not much to say. And as for other clients… well... you know I can’t talk about them.”

“Well…well okay, but… but what about your time before Ponyville… what about when you lived in Manehattan?” she asked.

And there it was. There are too many reasons I don’t like talking about my life in Manehattan, but Rarity wasn’t going to just walk away from this. I had to say something, and say something, I did.

“Can I be very very honest Rarity?” I asked, earnestly.

Rarity caught the sober tone in my voice, and calmed herself accordingly. “Of course, Guilty.” Her voice was all... concern.

“My personal life… or at least my life before Ponyville... it’s a very sore subject for me, and it... *sigh*... it isn’t something I really want to discuss… with anyone.” I stared straight into those sapphires she calls eyes, she was rapt with attention. “But even more than that… I just want a few things in my life that I can call.. mine.” Her eyebrow cocked.

“It’s like this: four times a week or so, I’m not me… I’m whoever the client needs me to be. I’m a psychiatrist, a confidant, a quick lay… a date. I never get to be… me. I mean… I don’t even use my real name… no one names their kid ‘Guilty Pleasure.’” I could see something resembling guilt begin to overtake her features. She was starting to get it.

“And even more than just that: It’s not just my... my, attitude or my time… It’s my body... it’s me. Every part of me belongs to someone else. For a few hours I exist for the pleasure of the client, in every way. So if there are just a few things, a few sacred things… just a few bastions of privacy I keep in my very exposed life… I think, Rarity, that it isn’t too much to ask that you respect that.”

It took a lot of effort, but I managed to keep a smile on my face the whole time. Rarity on the other hand was at a total loss for words; her jaw just... hanged open. I reached up and closed it for her. “Careful, dear, you’ll attract flies.” I was once more in the act, back to being the proper gentlemen.

“I’m… I’m so sorry. I-I wasn’t trying to pry or anything I jus-” I cut her off.

“Yes you were, Rarity… you were exactly trying to pry,” I teased. I stuck my tongue out at her playfully. “You naughty girl, you.”

“I… uh… I *ahem* Yes, well… I guess I have been rather naughty this evening haven’t I?” She was smiling again, thank goodness. “I am sorry, though.” She looked sincere. ‘Hmmm, I guess I shouldn’t hold it against her.’

“Don’t’ worry about it, m’dear.”

“Can I ask just one question, Guilty?” She looked up at me pleadingly. “Why do you do this? Why do you put yourself through all that?”

“Oh, it’s not so bad. For the most part I really love this job,” I replied.

“But why this? I’m sure there a hundred things a stallion of your talents could do,” she asked.

“Because, Rarity… this is the nicest way I’ve found to use my special talent,” I answered cryptically. I knew I wasn’t really giving her much to go on; but it was as much as I was willing to give.

To her credit, she seemed to accept that answer, surprisingly. “One of these days I am going to figure out what exactly that is, you know,” she teased. “One more question, Guilty?”

“Of course”

“What do you want to do?”

That’s not a question I get asked a lot. Even when I do, I don’t usually answer it honestly. I just tell the client something they want to hear.

For some reason, though, when Rarity asked me right then, I didn’t lie. “You know what I’d like to do, Rarity? I’d like to run into the kitchen, grab two spoons and a gallon of cookie dough ice cream, and just eat and talk until we fall asleep… How does that sound?”

“That… sounds very nice, actually.” Her smile right then... right when she said that... it was perfect. Any description I could give wouldn’t do it justice. It was just so happy... caring... serene.

The two of us spent what must have been hours just gossiping and devouring frozen goodness. It was heavenly, I even went so far as to drop my act… sort of… briefly… a couple times. We eventually polished off the entire gallon; and I must admit, it was the most fun I’ve ever had with Rarity. She fell asleep sometime after midnight, cuddling up next to me in the waning candlelight of the bedroom. It was nice.

Even now as I write, her delicate frame clings to mine, and soon the combined exhaustion and food coma will push me over the edge into unconsciousness. I’m somewhat thankful to her, It’s not often I enjoy myself that much during an appointment. I hope Rarity enjoyed it just as much as I did.

Regulars

Chapter 3

Regulars

Dear Journal,

I awoke entangled in a ball of pony, hooves intertwined with my partner’s. I blearily pried my eyes open to see the sleeping mare in front of me. Before long, memories of last night’s debauchery began to sink in. I quickly freed myself and rolled off of the bed. A quick glance at the clock told me it was still before noon. I don’t usually sleep in, but then again I don’t usually sleep downstairs, or wrapped in anypony's hooves for that matter. My head was throbbing, a far cry from the worst hangover I've ever had but still enough to warrant some aspirin.

As I returned from the bathroom to wash my face I found Rarity beginning to stir. “Mmmmwhat time is it?” she groaned, as her eyes blearily scanned the room.

“Ten-thirty,” I said. “And how did we sleep?”

“Oh, splendidly,” she winced. “Though, I can’t say much for this headache.”

“A bit too much to drink, my dear?” I giggled, triumphantly. I may have had a hangover, but it wasn't nearly as bad as hers by the looks of it.

“How do you do that? You drink nearly as much as I do, but you never seem…rrrgh,” she held cradled her head in her hooves, “…too suffer like I do.”

“Years of practice,” I teased, as I left to grab some aspirin.

I returned with pills and water, which Rarity and I happily downed. “Thank you, darling,” she gasped, “What are the damages?”

It took me a minute to realize what she was asking, and after some quick math, I had her answer. “Counting until eleven o'clock… four-hundred and ten bits.”

She winced, this time at the price. She quickly searched through her dress, pulling a small coin purse from somewhere within, and began counting out my fee. “Oh dear… I, uh, I only have four-hundred,” she admitted.

I always hate this, as much as I would love to just call it even, I can’t. It’s a slippery slope. The moment a client thinks I can be persuaded out of money, it’s only a matter of time until they start coming over and expecting me to knock time off of the meter. “Then just bring the extra ten next time… up front.” There was no charm or pomp in my voice; it was stern and unyielding. As much as I enjoy the company of some of my clients, they are just that… clients, and have to be treated as such.

“O-Of course...” she stuttered, looking a little guilty. It’s never fun to be the bad guy, but sometimes I have to. “I, uh, do I still have until 11 then?” she asked, albeit very cautiously.

“Certainly.” I smiled at her. Even if I have to play the bad guy, I don’t have to play it for very long… usually. “But, I must ask… aren't you usually open by now?”

“Oh, I don’t open on Sundays, dear,” she remarked, folding her dress into a neat pile.

I was already walking out of the room, off to prepare breakfast, when I heard her.

Sunday.

“I, uh, I’m sorry, Rarity, did… haha… did you say… Sunday?” I asked, praying I’d misheard her.

“Why, yes dear… I couldn't very well stay the night if it was a work night, now, could I?” She smiled at me once more. I wasn't even looking at her at this point.

“I’m terribly sorry, Rarity, But I’m afraid I’m going to have to ask you to leave.”

“But, I thought you said-”

“Ignore that… I only have 30 minutes to get ready for my appointment!”

“But what about-”

“Forget the extra ten bits… in fact…” I hoofed her back ten bits. “Call it until ten, and then its only three-ninety.” So much for stern and unyielding.

“Oh, uh, alright then.” She took the bits, looking more than a little confused.

I slowed down… I realized how fast I was moving… and talking, and it was upsetting my client. I composed myself almost instantly. “Forgive me Rarity, It’s just… I completely forgot that today was Sunday, and I have a client coming in…” I glanced at the clock “28 minutes, and I really hate to do this to you, but I really must ask you to leave a bit early… to protect their anonymity… and yours.” Cue the dazzling smile. “You do understand, don’t you?”

Rarity grinned. “Nice save,” she teased. I’m fairly certain I blushed a little.

I helped Rarity gather her things and after a quick brush of her mane, I led her out… she didn't seem to upset by the whole… getting kicked out thing… but hey I had more important matters to attend to. First, I had to erase all evidence of Rarity. Perfume still lingered in the air, sheets still smelled of sex, ice cream lay melting into soup, I still reeked of mare, the folding screens were still out, and there were dishes to be done… there was much to do.

Windows were opened to air out my home. I always have a set of clean sheets for the bed, which was quickly remade. The Puddles that was once a half-eaten gallon of cookie dough ice cream was quickly poured down the sink and a quick shower washed me of my offending odors. I let myself dry while I put away screens, cleaned plates, and downed a birth control potion.

10:55, no time for pants, but other than that, everything was just about perfect, leaving me five minutes to catch my breath. I trotted downstairs and unlocked the door, waiting for my client’s arrival. Out of all my clients she is certainly the one I’m the most grateful for. You see, every Sunday, and I do mean every Sunday, I have a two hour appointment, with what is probably the only client I consider a regular.

With most of my clients, it’s a guessing game. I’m always trying to figure out what is wanted of me, trying to figure out who I need to be. With her it’s easy, not because she’s transparent, or simple, but because she knows exactly what she wants and isn't afraid to ask for it.

The door flew open and she was there, with a small basket in her mouth. She stepped into my home and placed her basket on a table. “Hey, Guilty! No pants today?” I smiled at her, an honest smile, because I truly am happy to see her.

“Not today Derpy,” I mused, staring into her mismatched sunset eyes.

“Mmkay!, I brought zucchini today!” she said. She instantly began walking into the bedroom. “C'mon Guilty, it’s time for sex!” she announced giddily, trotting away, wiggling her rear end at me. Celestia, love her.

“You’re the boss.” I happily followed her, watching her blonde tail twitch and raise. Her rear-end bounced with each step.

She has a dynamite ass.

It’s always like this, every week she brings muffins, apparently today was zucchini. She’s always ready to go right when she arrives, and always so happy every step of the way. It really feels good, having a client that so enjoys my efforts, that appreciates what I do enough to come back every week... and bring muffins.

She trotted over to the bed, now free of any sign of recent use, and folded her forehooves on the mattress. She raised her tail high, and it splayed out on her back. I eagerly walked up behind her, mounting myself atop her frame, planting my own fore-hooves on either side of her head, like always.

“So, how’s business?” she asked, turning a curious glance back at me as I fumbled with my ever swelling self.

“Not bad, made a small fortune last night,” I responded, as I pressed the end of my now firm stallionhood against her entrance.

“That’s niiIIIIIIIIIIIIIce,” she moaned as I thrust the length of myself inside her with ease. “Anyone *huff* I know?”

“You *huff* know I can’t *huff* discuss that.” It’s sort of our little ritual, she always wants to small talk during sex. I’m actually pretty thankful for the mental stimulation during sex. When you do this as much as I do and it can get monotonous. Fun, but monotonous.

“Weather's *huff* supposed to be *huff* rainy s-soon.” Each word was a struggle for her, but she continued on regardless.

“*huff* Yeah?” It wasn't much easier for me.

“Yeah *huff* Rainbow Dash t-told me.” She talks about Rainbow Dash sometimes; she’s apparently a friend of hers who works on the weather patrol.

“Huh… How’s Dinky?” Most ponies I know would probably not want to talk about their children during a good plowing, but Derpy is not most ponies.

“Oh, my little muffin is in troooOOOOOUUUUUUUUBLLLLLLLLLLLE!” I felt her insides clench me tight as a brief orgasm shot through her.

“*huff* Yeah? *grunt * What’d she do?” Her answer took a few seconds, she was still riding waves of pleasure. I continued to thrust away, regardless.

“She was *huff* fighting *huff* somepony at *huff* school.”

“Oh?” I’d never met Dinky, but I had grown to know her through her mother’s weekly news, and that didn’t sound anything like the Dinky I’d heard so much about. “That doesn't *grunt* sound anything *grunt* like the Dinky *grunt* I’ve heard so much about.”

She grumbled. “Something’s *mmm* been upsetting her... she won’t talk *huff* to meeEEEEEEEEEEEEEEEEEEEEEEE OOOOOH LUNA!!!” Another climax shot through her, and her walls clenched my throbbing self again. My humping continued on through her pleasure. Derpy was fairly easy to please, and multiply orgasmic to boot, but that doesn't mean I don't give it my all. After several orgasms I knew she’d be worn out, and we’d retire to the foyer for talk. And muffins. I like muffins.

“Wish I could *nngh* help you there… no good with *huff* kids.” Sweat began to build up on both of us, and I could taste the salt on my lips.

She groaned in response, partially from frustration and partially from pleasure. “I just *huff* I don’t know *huff* how to *ugh* talk to her.”

“Hmm *huff* did she *huff* win at least?” I asked. Pleasing Derpy was second nature at this point, so I was more focused on the conversation.

“Ooooh yeah *huff* she did. *huff* chipped the *grunt* poor kid’s *ngh* tooooOOOOOO-OOOOOOOOOTH!”

“Yeeeesh, that kid *unf* must have a *grunt* hell of a kick.”

“No, She *huff* threw her lunchbox *huff* aaAAAAAAAAAA SWEET CELESTIA!... at the kid with *nngh* her MAAAAAAAAAAAAAAAAAAAAAAAAAAaaagic!”

“Twice in one *huff* sentence?” I have to say I was genuinely impressed with myself.

“Yeah… *huff*… *huff*… gimme a minute.”

I dismounted the grey mare and she sank forward into the bed, legs twitching erratically. She slowly managed to squirm her way up onto the cloud, panting heavily, lazily rolling over onto her back. She was really quite beautiful like that, wings splayed out at her sides, a satisfied smile on her face, eyes half lidded. Picturesque. I climbed on next to her, (mindful of her wings) and rolled to face her. “So… she’s grounded then?”

“I dunno…” she managed between breaths. “Lick me?”

“Of course,” I responded, eager to dive right in. I grabbed her by the knees, sliding her over to face me, she gave a surprised yelp as I plunged my muzzle between her legs. Now came the part of our appointment in which Guilty’s mouth was otherwise occupied, and could not entertain dialogue. Luckily, Derpy seems more than content with monologue. She spoke as I eagerly lapped up her juices.

There’s no need to start slow with Derpy, in any regard. I can always start full throttle. So my tongue was quickly exploring her deepest regions.

“I dunno… It’s just *mmmmmm* hard to get her to *huff* open up, you know? As much as I try, *nngh* I can’t seem get her to *huff* to talk to me. Something is *huff* definitely bothering her but… *sigh*I just *mmm* I don’t know. Her father was much better at this… *ah*” She began to squeak in pleasure as I licked her. Her hoof found its way to my head, pushing my snout encouragingly deeper into her folds. “It’s *ah* frustrating.”

Her hips began to rock slightly against my face, and a throaty moan escaped her lips. “You’re really good at that you know? This is *huff* just what I needed after a week like this. My boss yelled at me *huff*… again; I dropped another *nngh* package. Broke a bunch of glassware, cheap stuff but… aaaaAAAAAAAAAAAAH!” Her inner walls pulsed and swelled with her climax, clenching pleasantly down on my tongue. When her climax subsided, I pulled myself up to face her, staring back into her mixed expression of sadness, guilt, and post orgasmic bliss. “…*huff*… I think I’m getting worse, Guilty… making more mistakes… getting… clumsier.”

I gazed down at her, trying my best to appear sympathetic... well as sympathetic as one can with a face covered in mare juices. “You know, you always say you’re clumsy, but I've never seen you do anything clumsy.”

“Well, I mean, I’m not exactly handling delicate packages or anything over here,” she said.

“I beg to differ,” I responded, chuckling at my own joke.

“Oh shut up, you,” she practically giggled the words, playfully kicking me onto my back.

She crawled on top of me, her face was deadly serious. I was almost worried, until she threw up a hoof in mock salute. “Sir, permission to handle delicate package!” I almost broke out in laughter, it was priceless. I don’t know why she suddenly decided she was a soldier but I didn't particularly care.

“Granted!” I bellowed in the most ‘military’ cadence a stallion of my… octave… could muster. Derpy took hold of my knees, spreading my legs to get a better look at my still fully erect self. She brought her lips to the end of me and gave my flesh a quick peck before talking the end of it in her mouth. She might lack the pure skill of Rarity, but that doesn't mean getting head from Derpy is anything less than pleasurable. However, this turn of events meant it was Guilty’s turn to talk.

“You know *nngh* Derpy? I think you’re *huff* being hard on yourself.*guh* Dinky’s lucky *huff* to have a parent *huff* as good as you. Oh fuck that feels good. Trust me. And don’t worry so much *huff* about trying to *ugh* get her to *huff* open up. Kids deserve *huff* at least one secreAAHAAHA-AAAAAH!” I gasped in surprise as she took another few inches of my flesh into her mouth. I noticed that at some point during our fun she had slipped one of her hooves down between her haunches, and had been clopping herself silly.

“And as for *huff* work… damn, your getting good at this… but, ah, as for work, I *guh* seriously have never seen you be *nnnnf* clumsy. Maybe it’s *guh* stress. You get all *huff* worked up and you *huff* get all ditzy… maybe.” I felt a familiar clenching in my testes and I knew I was almost done. “I’m pretty close… where do you want it?”

*Mmmmph!” was her only response. ‘Looks like she’s hungry.’

My hips bucked and my eyes clenched as climax overtook me. I spilled myself into her wanting mouth; several short bursts shot down her throat. I sank back into the cloud as aftershocks of pleasure sent shivers through my limbs. My cock slipped messily out my Derpy's mouth with a slight *pop.* I gasped for air.

Derpy's face rose up next to mine; she was licking her lips thoughtfully. “It’s pretty thin today… some one’s been busy!” she teased. I love that about her, never afraid of crude humor, never afraid of asking for what she wants, never ashamed of anything. She laid down next to me, grinning like a fool. “I really needed this.”

“Glad I could help… feel like a shower?”

“Sounds great!” Ever chipper this one. We trotted through the foyer to the staircase… I could hear the siren song of zucchini muffins as we went. Their sinful chords caressing my ears, their sweet aroma wafting across my nose and though my brain, I wanted… needed them.

‘No Guilty!… the muffins will wait.’

Up the stairs and into the bathroom we walked. My shower is perfectly big enough for two ponies, more like a shower room than a shower box, two nozzles too. A myriad of shampoos and soaps litter the walls, half of them have never been used, but I like to collect them, makes the shower look exciting. Derpy never uses any of it though. As always, she just turned on the water and let it soak her. She looked particularly meditative today, just letting the water run down her mane and over her back, just the hint of a grin on her face. Very... Peaceful.

I had already been rinsing some vanilla peach shower gel out of coat by the time she spoke up. It was strange, She’s usually so quiet during our shower. “Hey, Guilty?” she asked, her voice betraying caution.

“Mmmm,” I hummed in answer.

“Do you really think I’m a good mom?” I didn't need to look at her to see the pleading look on her face. She tends to underrate herself, and... I dunno... I felt a little self-esteem boosting could do her some good. I just smiled and told her:

“Heck, yeah! The way my dad treated me, I would have killed for a parent as nice as you. At least you don’t hit her or anything. You’re a great parent.”

I didn't realize until moments later what exactly I had said. I had laid bare a tiny, secret part of myself; but the unsettling thing is I hadn't even realized it. I’d let loose something from beyond the obscuring veil that hides my past from my clientele, a veil I used to think I watched like a hawk. To be fair, I hadn't really said anything; but I had heavily implied it, and even that… well quite frankly that scares me.

Derpy didn't say anything. She returned to her Zen state of warm showery bliss. I wonder if she picked up on what I’d said. I wonder if she picked up on how much it bothered me. Whether she did or she didn't, she didn't say anything. Our little shower continued on in silence. The smile never left Derpy's face.

After drying off and heading back into the kitchen, I put the kettle on. I could barely contain my desire for warm fresh-baked zucchini goodness, but I had waited this long, certainly I could wait for some tea. Derpy and I sat opposite each other, as always, and began the final part of our short weekly ritual.

“So… any luck?” It’s the same question I ask every week, and it always has the same answer.

“Meh…” Derpy responded for what must be nearly the hundredth time. “…I asked out my hairdresser.” The look on her face said it all, but I asked anyways. Derpy has been trying to get an honest date for longer than she’s been seeing me. Sadly, the only action she gets she has to pay for… not that I’m complaining.

“How’d that go?”

“…He’s gay…” her eyes fell to the floor in embarrassment, and she started to turn as red as a tomato. “… looking back it was actually pretty obvious. I had always thought that guy he was hugging was his brother... Oh, well.” Derpy shrugged. She’d struck out again… poor girl. As much as I enjoy her patronage, that mare really needs a stallion in her life. It’s gotta be tough being a single mother. Whatever the case the kettle was whistling which meant it was finally time to eat.

I returned from the kitchen, tea tray in tow. I tried to hide the drool dripping ever so slightly down the side of my face. Derpy unveiled the picnic basket of unearthly delights. I don’t know how she makes muffins this good, and I no longer care. Seeing her take two brown little pastries out from that wicker basket was the highlight of my week… like every week. She knows how much I love them, and she’s always happy to bring them. “Here’s your guilty pleasure, Guilty Pleasure,” she recited, laughing at her own terrible joke and passing me a solid nugget of heaven itself.

I quickly snatched it up and wasted no time in taking a huge bite out of the side of it. They’re perfect. They’re never anything but perfect. Despite all my attempts I've never been able to make a muffin on par with Derpy's. My guest was enjoying her muffin just as much as I was mine. Silence passed over us as the two of us basked in warm moist goodness, and not the erotic kind. My foyer was filled with wet smacking noises, the slurping of tea, and many *mmmmms* from both of us.

Muffin induced bliss, however glorious, is always short lived. There is no use in attempting to savor the muffin; you cannot help but take each bite right after the next. After our scrumptious snack was complete, satisfied smiles on both of our muzzles, we both let out a long contented sigh. “That was real good,” I said, the absolute height of articulation.

“Heck yeah, it was.” She said, a tiny avalanche of crumbs falling from her lips. “I’m thinking next week I’ll bring some Cranberry orange ones.”

“Oooh, I loooove those,” the words were practically drooled out of my mouth. I was already imagining them, warm and moist. Filled with berries, to the point where every bite ha at least five. Perfection. It was the only word for them. The way the moist little cranberries add bursts of flavor to-

“Guilty… you’re drooling,” she giggled. I hadn't even realized I’d spaced out. Muffins have that effect on me. I flushed a bit, scarcely believing I had let merely the prospect of future muffins send me into a full on muffin fantasy.

As much as I didn't want to disrupt our post-muffin Zen, I knew Derpy still had issues to work through, and being the good little escort I am, I wasn't about to let her walk out of here without a solid plan in mind. I had to get her back on track. It’s… well… it’s what I do.

One of the first things you learn as an escort is when it’s appropriate to handle things delicately, and when it’s time to be a little forceful. “So about Dinky…” This was the latter. “What’s your plan?”

Derpy just grumbled as her face fell into a pile of her hooves on the table. “I dunno,” came her muffled reply. She looked really pathetic, to be honest. I extended a hoof and patted her on the back.

“Well, what’s her punishment?” I asked.

“I dunno… I just… I always feel so mean when I punish her.” She rolled her face over to glance up at me with one very tired eye. “I’m just so sick of having to be the bad guy.” I wished I could relate with her. I hardly ever have to be the bad guy, I’m always the good guy, the Yes-Stallion, the pick-me-up. I really didn't know what to say.

Not that that’s ever stopped me.

“Derpy… as much as you don’t want to be the bad guy… I’m pretty sure you have to. Dinky needs discipline; she needs to learn that actions have consequences.” I wasn't doing half-bad, I may have been BS-ing it but it sounded halfway believable. “And... look, as long as she knows you love her, she’ll turn out halfway decent.” I wasn't really sure where I was getting this from. I felt like I was channeling a cheesy self-help book. Whatever the case, my tiny motivational speech seemed to cheer Derpy up considerably.

Before I could continue, she roped me into a tight hug, burying her face into my shoulder. “Thanks, Guilty. You always know just what to say.”

Apparently. I chuckled internally. Just it soon as it began, our embrace was over, and she was grinning up at me. “So…” she asked apprehensively “... what should I do? How do I punish her for fighting?”

“I dunno. No muffins for a week? That'd set me straight.” She giggled at that one.

“Hehehehe. No, I think I should just make her apologize.”

I scowled at that. It didn't sound right, the prospect of making a kid apologize. I mean, what if she’s not sorry? Kids should be allowed to be mad at each other. “I dunno, Derpy, seems weird to me... If she’s not sorry, she’s not sorry. I think she just needs some punishment. No allowance for a while, or no dessert for a week… something like that. Don’t make her be on good terms with a kid she clearly doesn't like.” Part of me felt I was overstepping my bounds, but Derpy and I are fairly close; plus I think she really appreciates any direction I can give her.

“Maybe… well whatever the case, I’ll figure it out.” And just like that, the smile was back on her face; the confidence was back in her voice. It always feels good doing that, bringing the life back into somepony so drained. There was a brief moment where she just smiled at me, a deep, grateful smile. It’s moments like that that really make me love what I do. That feeling of really helping someone with something… it really keeps me going some days. I didn't want that moment to end… I wanted her to keep smiling like that.

“Anyways, I should get going.” ‘Damn.’ She began grabbing up her things, putting everything back into her little basket.

“So soon?” I may have sounded the tiniest bit desperate.

“Guilty, It’s been...” she looked at the clock, “... almost two hours… besides, I gotta get home, or dinky will start to worry.” ‘Has it really been that long?’

That made me a little curious about something. “Where do you tell her you are every week?”

“Muffins with a friend.” She smiled that smile again. “Anyways… bye, Guilty.” She turned to walk out the door, and I watched her go. I do love watching that mare walk away. About twenty paces out she turned back and waved. She always does that, and I’m always sad to see her go.

I don’t have that many clients that make me feel that good about what I do. Mares like Rarity come to me because they need me to be someone. Some mares come to me just to see what it’s like to be with a… professional. Derpy's different; she comes to me because she likes sex. She treats me like a friend, and just so happens to enjoy supporting her friend’s business. I imagine that’s what it’s like to run a more… conventional business. Having a friend stop by, having a brief chat, providing your services, and ending everything with a thanks and a friendly goodbye. That sounds... It sounds… satisfying. Most clients just make me feel… tired.

I let out a massive yawn… ‘Speaking of tired’ I made my way back up to my room, trotting lazily up the stairs. Once there, I plopped down on my bed realizing how exhausted I was. What time had I fallen asleep? I couldn't remember. Whatever the case, I was just happy to be done...

I was done right?

I brought myself to my hooves and quickly snatched up my ledger. I had realized that I hadn't actually checked it yet. I hadn't been in my room at all really. I quickly flipped through it to today’s page.

‘Oh no… not her… anyone but her.’

It took all my mental fortitude not to just collapse at the sight of her name. I’d completely forgotten. She’d written last month, said she couldn't make her normal appointment… I must have penciled her in for today… what was I thinking?

2 ‘o’ clock, it read. That gave me… little more than an hour to do… everything… again. I groaned, one emergency clean-up was draining enough, but two? Two was just hell.

The second time through went much slower. I was exhausted, in every sense of the word. Bedroom aired out, table cleaned, emergency sheets put in laundry, non-emergency sheets cleaned and dried with a space heater, hair washed and brushed. After two sessions I still couldn't quite get the smell of mare off of me, so a little cologne was necessary.

I was silently cursing myself. How could I schedule so many clients so close together? . I should've paid more attention to my schedule. I shouldn't have let Rarity stay the night. I was drained. Knowing this mare, it wasn't going to be a long session, but still, any amount of time with her was a chore.

A knock came at the door. She was here. I gathered up all of my exhaustion, and shoved it deep inside of me. Even if I was exhausted, and even if I wasn't exactly fond of this client, I still have standards. I swallowed hard, put a smile on my face and answered the door. “Hello again, Miss Carrot Top.”

“Hey.” That’s all I got. No, ‘Nice to see you.’ No, ‘How’s it going.’ She practically pushed me over rushing inside. Didn't want to be seen at the whore’s house. She took her saddle bags off and made a beeline for the bedroom, her little curly tail bobbing to and fro. She is pretty attractive, truth be told. Cute face, nice little ass, I’m sure if she put any effort into being nice she wouldn't need to come to me.

And that’s what it really comes down to with her. She needs to be here, she just doesn't want to be. I've serviced plenty of mares like her in my time, it’s just that most of them don’t come back for seconds. Most of the time, mares like her are curious, lonely, or both. Maybe they haven’t had a date in a few months, maybe they just want to try it out. Whatever the case, they usually show up, get down to business, and go home feeling dirty and empty.

Carrot Top (which I’m fairly certain is not her real name) on the other hand has, shall we say, developed a bad habit. Every few weeks or so, she writes in, desperate for pleasure, with a time and date. She pays for one hour, and rarely uses the whole thing. She can never get out of here fast enough, quite frankly. But she needs it. And she hates that she does.

“You coming?” She glared back at me, impatient.

“Of course.” As a totally unrelated side note, I've become very good at keeping the venom out of my voice. She trotted into the bedroom like she owned the place. To be fair, for the next hour, she sort of did. “The usual, I presume.” She didn't answer, she just took her usual position on the bed. Bent over the end of it, tail up, legs spread. “Okay, lemme just...” I opened one of my wooden chests and took a swig of what I then realized was my last birth control potion. “Alright, then.”

I took my position behind her. Normally, with her, I’m just as eager to get it over with as she is, but an overnight and a visit with Derpy had taken their toll, and well… ‘The flesh is weak.’ I had to stroke myself for a bit, just to get myself hard enough to get inside. From the looks of her, she was more than ready.

I eased myself inside her once I could, my half-erection sliding inside her sopping lips. I took no pleasure from sex with Carrot Top, I never do. It’s just a job. “Is that okay?” I asked.

“Yes. Fine. Just… stop talking.” I often wonder who she imagines is fucking her. She must be imagining someone; because once I’ve started I’m not supposed to say a word. Before long I felt my erection reach full mass, and Carrot Top started moaning.

We carried on like this for a short while. Carrot Top, Imagining the Stallion of her dreams; Myself trying to pretend I was anywhere else. We never changed position, we never spoke, we never looked each other in the eyes. It was nothing but eleven and a half minutes of cold emotionless thrusting, like always.

She came, quietly, motionlessly, almost like she didn't want me to know. I could feel her though, her inner walls squeezing on me, her legs shivering slightly. I came soon after. She wants me to come inside; she likes the feeling of being filled. I started to fall into her, sinking down into her as much out of exhaustion as bliss, only to have her ungracefully wriggle out from beneath me. “Was that to your satisfaction?” I asked her, half out of spite.

“Yeah, fine… I’m gonna shower.” She was already out the bedroom door. She didn't look back at me; she just hurried out of the room, tail between her legs. I already knew she was headed upstairs to wash my smell off of her.

It’s jobs like this that really wear on an escort’s soul, the ones who aren't interested in your services, but just interested in being serviced. On jobs like this, I’m not engaging the client. I’m not learning about them or helping them with their problems. As much as I hate to admit it, jobs like this just make me feel like a whore again. I’m just a toy for the client to play with, only to be forsaken once I've lost my usefulness. The client is just using me to masturbate.

It makes me feel… I don’t know… spent, used up, empty.

Minutes later, I heard Carrot Top descend the stairs. I picked myself up off of the bed and meet her in the foyer. When I got there, I found her sniffing curiously at the air. “Do you smell that?” She asked… SHE asked. She actually engaged me. Was this a chance to actually connect with this impossible mare? I was so stunned I almost didn't have the mental awareness to respond. Almost.

I took a whiff. Heaven. Perfect muffiny bliss still permeated the room, teasing me with memories of pastries gone. “Just smells like muffins. I had some earlier.”

“Huh,” she practically grunted… so much for connecting. “Anyways...” she reached into her bags, which leaned against the door, and produced a small pouch of coins, only to dump it out atop my table. The coins clattered haphazardly onto the wood. “…bye, Guilty.”

And then she left. She just walked out the door leaving me to gather up my coins. Still, that’s exactly what I did; I gathered up my earnings. It doesn't really bother me… not really. I've had plenty of clients pull that sort of thing, at least she had the decency to dump it on the table, and not the floor. Some of my clients have even stayed and watched me pick it all up. It makes them feel better about the whole thing somehow. I dunno. Speaking of earnings, I had made quite the haul today, four hundred and fifty bits in total. Not too shabby.

There’s not a lot of cleanup whenever Carrot Top visits. Barely even messes up the bed. Still, I wouldn't be a professional if I just left used sheets out. My place would require another quick round of clean-up. But first, a shower… a proper, warm, relaxing, lengthy, indulgent shower.

I trudged up the stairs into my bathroom, still steamy from Carrot Top’s shower. I turned the valves and my shower sprang to life. It felt good... damn good. It was my third shower of the day, but my first actually relaxing one. Nice and hot, it washed the day off of me; it was divine. So much built up sweat and ache, all washed away in the shower’s cleansing waters. For the longest time I just stood in the nozzles line of fire. My head slumped down, water dripping off my muzzle. I swear; I almost fell asleep standing there.

It wasn't until I started actually washing myself that things took a turn for the unpleasant. When starting out as a… well as a whore… showers are not exactly a happy place. You can’t help but feel filthy. You have to wash everything off of you, and sometimes you kind of... freak out.

I remember, after my first job I was in the shower for HOURS. It wasn't that it was unpleasant, or even my first time having sex. It was just... I kinda can’t put it into words. I felt dirty. I felt... well, guilty. Did I feel bad that I was making money with sex? Not really, sex has always just been... sex. Did I feel bad because it was degrading and humiliating? No, it wasn't bad, in fact she was a very nice older woman. Did I feel bad because I felt like I made a mistake? Definitely not, Getting into the escort business got me out of a bad home life. Given the opportunity I’d do it all over again.

Whatever the case, after my first job I just... I just needed to get clean. I hopped in a shower and... by the time I got out I had scrubbed myself raw, and damn near had first degree burns from the water. I just couldn't get the water hot enough. Apparently it’s fairly common, at least according to some of the other escorts at... where I used to work. It... it honestly wasn't that bad. For a while I had to take extra care not to scrub too hard, but that was it, honest. After a while showers were just... showers again.

But every once in a while... I... fuck... I fall back into old habits. I had a bit of a breakdown tonight, alone in my shower. It started out fine. I grabbed a loofah and a little dollop of liquid soap, and got to work, scrubbing the sweat and cum and juices out of my coat and mane. I don’t know exactly when I started, but before I realized it I was scrubbing very hard. I couldn't keep my breath even, I couldn't stop scrubbing. My mind kinda... seized up and the only thing I could do was clean. Clean clean clean. I had to get clean, had to wash it all off of me, wash off the filth. Wash wash wash; scrub scrub scrub it all away. I felt dirty, so so so dirty. It was... It felt like I was eighteen again, back after my first job.

Pain is what snapped me out of it, a combination of raw skin and hot water made me wince and lose grip of the loofah. I realized then what I had been doing. ‘Really?! I haven’t freaked out like this in… AGES.’ I rushed out of the shower, not even bothering to turn off the water as I went to the mirror. I wiped the built up steam off the mirror; I just had to see myself
.

I looked awful. My eyes were red from crying. Had I been crying? I honestly don’t remember, but I must have been. More than anything, though, I looked... fatigued... is the word I’m gonna use. I had dark circles under my eye; my skin was red. Even under my coat, I could see it. My mane was a mess, I hadn't really shampooed it at all, much less conditioned. Eventually I had the presence of mind to turn off the shower and dry myself off.

I honestly didn't know what set me off. Carrot Top hadn't been any worse than usual, better even. She actually asked me a question after her shower, and she never engages me if she doesn't have to. Was I just worn out? Had too many appointments taken their toll? Was it all the showers in one day, maybe? Was it overexposure triggering an episode?

Whatever the case there was still work to be done, and plans to be made. I trudged through my final chores. Cleaning the sheets once more. The backup sheets were stashed away once again, ready for action in case of another mishap. The sheets were put into the washer, I’d run it in the morning. More importantly I had to take inventory. Tomorrow is a free day, and I’m low on supplies, so there is much to do tomorrow… in town… *sigh.*

Currently, I am out of birth control potions, so I needed to pay Zecora a visit. Low on honey lemon oil (my favorite,) so I have to stop by the spa. While I’m there I think I’ll grab some candles, something pungent… cinnamon maybe, I saw those last time I was in. I just may let the twins talk me into a massage, that would be nice. A mane-cut is way overdue, so I’ll have to stop by the barber shop. I’m fairly low on groceries as well; I have to grab some food. Oh, and have to make a payment, I can’t forget to stop by the post office.

I think that about covers it, so I’m off to sleep.

First, however, I would like to write something.

Though today ended poorly, I would have to consider it a good day.

Good friends were met, and good muffins were had.

Author's Note

CHAPTER 3!!!

I hope you guys like it. Some of you may not like my portrayal of some ponies, but get used to it. Somepony's gotta be the bad guy, and there will be more than a few in chapters to come.

Stocking up

Chapter 4

Stocking Up

Dear Journal,

It was raining when I got up, if just only a little. I don’t particularly like to go into Ponyville, but I do have to get supplies every now and then. The walk into town is pretty nice, though. Or at least it would’ve been if it weren’t muddy and cloudy... and cold. Even in jeans and a hooded sweatshirt, the cold still got to me; so I shivered my way down the lonely little path to Ponyville.

There are a couple reasons I never really enjoy going into town. First and foremost is the attention I get. Now it’s not that I don’t like attention; I just don’t like the kind I get from some of the folks in town. Lots of hushed conversations behind my back. ‘Is that him?’ ‘I wonder what his cutie mark looks like.’ ‘I can’t believe he thinks he can bring that sort of business here.’ Blah blah blah. I’ve mostly gotten used to it, but still. It’s no fun being infamous.

Another reason I don’t like going into town is clients. It’s not that I hate my clients; I don’t. I just don’t like walking into their personal lives. My mere presence can make some clients blush. Not only that, but it can get kind of hard not imagining all those mares in compromising positions. Over and under and behind, wet and sweating and... in ecstasy. Sometimes it’s enough to make me blush.

Once I made my way into town I couldn’t help but take a mental tally of my clients. ‘There’s daisy, she likes it rough. That’s Cheerilee, she’s into roleplaying. That one calls herself C, she likes it when I talk dirty.’ It’s kind of eye-opening, I suppose, seeing all my clients going about their business. Each of them has a life, a job, a family, errands, chores. It’s easy for me to forget about all that, since whenever they come to see me… they leave all of that behind them. They’re just different ponies when they’re with me.

Enlightening... that’s a good word for it.

I wasted no time making my way over to my first stop: Close Shave’s barber shop. Close is a great guy, always greets me with a smile. I think he knows how much people talk about me, so he goes out of his way to make me feel welcome. He’s from Manehattan too, actually; which is probably why he doesn’t really care about what I do.

Close is a pretty big guy for a unicorn; he used to be in the royal guard. Ponyville was something of a retirement for him. From what he’s told me, he never actually had a barber shop until he retired. He was a guard barber, cut hair for his fellow guardsman for 10 long years. Once he became an officer, he sort of missed cutting hair. After he retired, he saw it as an oppurtunity to trim again.

He was busily sweeping some leaves off of his store front when he spotted me. “Well, well, If it isn’t Guilty, lookin’ like a fuckin’ hippy,” he chuckled. I guess my mane had gotten pretty long.

“Hey at least I still got color in my mane.” I jabbed right back.

“Yeah, fuck you too…” He walked me inside his establishment. “Now, let’s see if we can’t make little Guilty look like a boy again.” He laughed again. He has a throaty laugh... a smokers laugh.

I love this guy.

“So… how are all your girlfriends doing?” He asked, leading me over to his old barber chair, cracked and worn from years of use. I shook off my saddle bags, and stuffed them nearby.

“They’re, not my girlfriends, Close… they’re clients.” I took my seat, and he levitated a smock around my neck, each button snapping into place with a little *click.*

“What’s the difference?” He asked jokingly. A spray bottle from his little counter levitated over to me, and began misting my hair.

“They pay me, Close. They pay me to be with them.” I love flaunting that little fact in front of him. It makes him jealous.

“Yeah, well, let me know when your medal comes in.”

“Oh? What medal would that be?”

“The one fer ‘Luckiest Stallion in Equestria,’ ya son of a bitch,” He snarked. He began to run a comb through my mane. It’s really calming, getting my hair cut. It’s one of the few times when I can sit back and let someone take care of me. I almost dozed off, sitting there, just letting Close comb my mane. His voiced snapped me out of my trance. “So, Guilty, how’s life?”

“I can’t complain…”

“‘Can’t complain’… geez. Listen to you! Ya got the sexiest fillies this side of Equestria knockin’ on your door, beggin’ fer some sugar, and you… ‘can’t complain.’ I oughtta fuckin’ smack you.” He let out a deep sigh, as his comb floated back into its little jar of barbicide. “Seriously though, Guilty, how are ya?”

“… Fine, I guess. I had a new client a few days ago.” I tend to tell Close a little more than I probably should. It’s usually fine, he’s not much of a blabber mouth and I keep things anonymous enough.

“Sexy girl?”

“More cute, than sexy, really,” I answered. I thought back to Twilight’s appointment. The blushing, the stammering, the worry, even the panic was cute.

“Hmm… that’s fine too, I guess.”

“Trust me, Close, she was more than fine.”

“Yeah, yeah…” By now, Close had begun snipping away at my hair, his little scissors hovering around my locks in a silvery cloud of magic. Occasionally diving in and taking a quick snip, sending moist tendrils of hair plummeting onto my smock, and the floor.

I wish I had magic. So much of what I do would be so easy with magic. Time saved getting dressed alone would shave hours off of my week. Not to mention the multitasking capabilities for cooking and... sexy things. That would be great.

That said, even if I had magic, I don’t think I’d be able to do anything with it. I had a unicorn friend try and explain magic to me once. That may have been the most confused I have ever been. I gave up on ever understanding magic, that day. Either way, from what I understand, if I was a unicorn I might lose a lot of the stamina I have now. Unicorns have to work a little harder to stay in shape, or so I’m told. I’d probably lose some of my already underwhelming ‘size,’ as well. Stereotypes are stereotypes for a reason.

“Good between the sheets? The new girl, I mean.” Close’s voice shook me from my musing.

“Hmm? Oh, no I didn’t… service… her.”

“Really, that’s a shame? Wait... do you still get paid for that?”

“Yes… yes I do.” I couldn’t help but grin.

The barber shop was silent for a while. “… I fucking hate you, Guilty.”

“I love you too, Close.”

“*Hmph…*” he grunted. “Keeping busy, then, I take it?”

“Ugh... too busy.” I was tired just thinking about yesterday.

“Oh, don’t you even dare complain about fucking too many mares!” He mock shouted.

“No, not too many mares, just… too close together.. I’m just kinda worn out today.”

“Oh, for fuck’s sake… What’sa matter? Poor little fella can’t handle all the ass being thrown at him? Let’s all shed a fuckin’ tear for poor, poor, Guilty.” Close just rolled his eyes.

“I’m serious. It’s not easy spending close to twenty-four hours with clients.”

“Fuckin’… a whole day? Stars above, Guilty, when do you find time for yourself?” Close just shook his head, as his scissors continued to click away.

“I find plenty of time to myself. It’s not always that busy.”

“I dunno, pal, I never see you just… out on the town, or anything.”

“Well, not in town… not really. Any time to myself is usually, you know… at home. Reading magazines… exercising… you know… me time,” I confessed.

“Shit, kid… You gotta get out more. Wastin’ the best years of yer life.” Close just shook his head again.

“Really… you’re calling what I do ‘wasting?’”

“No, I’m callin’ what you do between doin’ ‘wasting.’”

“How so?” I asked.

“You need a fuckin’ hobby kid… bowling, hoofball, fuckin’ stamp collecting… somethin’ to getcha outta the fuckin’ house.” The way Close said that kind of caught my attention. It wasn’t joking, abrasive, or crude. He was serious… just barely serious, but serious. Like he really thought I needed to get out more. As much as Close pries, he’s never really been one to butt into other’s business, at least not as far as I can tell.

“If you don’t mind me saying, Close… what’s it to you?” I wasn’t trying to sound offended, but I think I kind of did.

“Nothin’, nothin’, just… Look, take it from a guy who spent the better part of his best years married to the job. When I was stationed in Canterlot, I was... well… I never let myself live a little, you know? I… I dunno, for a long time I just kinda… lost sight of what was important.”

I was almost at a loss for words. “What the fuck, Close?” When had he become so… sappy.

“A: Watch your fuckin’ mouth. B: … I worry about you Guilty. You’ve been here for… what two years now? I never see you out with friends; I never see you chattin’ up some sexy piece of mare, when I know you could probably get any girl you want. I never even see you eatin’ out… shoppin’… anything. You’re not… *sigh*… You’re not, livin’ life. I like you, kid … and I hate to see a guy make the same mistakes I did.” A manedryer started blowing.

I opened my mouth to respond, only to have guilty speak up again and cut me off. “And before you make that crack about eatin’ out that I know you’re just dyin’ to make… I saw it comin’.”

‘He’s good.’ I couldn’t help but snicker. “Getting’ sentimental in your old age?” I cracked.

“Yeah, maybe so, Guilty… How’s it look?”

I hadn’t even realized he was done. My mane looked pretty good. Close has a decent sense of style for an older guy. It was short, but feathered and styled. “I look sexy,” I admitted. “Thanks again, Close.” I started to get up, ready to pull my wallet out, only to have a sturdy grey hoof push me back into my seat.

“Where the fuck do you think you’re goin’.” He chided. I’m not lettin’ you walk outta here without a proper fuckin’ shave.”

“C’mon, Close, I look fine. I shaved a couple days ago.”

“With what… a fuckin’ saw? Sit down, you look like a jackass.”

Being shaved with a straight razor is actually pretty neat. It’s the smoothest your face will ever be, even if it only really lasts half a day. Still, it’s pretty fun, for what is basically having sharp steel scraped across my throat by an ex-royal guard whom I tease on a regular basis.

Close quickly began lathering up a brush. “I am serious, just so you know. You need a damn social life.” He coated my face and neck in hot, soothing shaving cream.

“Where’s all this coming from, Close?” Close’s straight razor hovered over to my neck.

“Fuckin’ hold still, don’t wanna slit your throat... That’s a lie, by the way,” he snarked. His razor started to scrape slowly across my face, collecting little dollops of shaving cream and hair. He’d flick each dollop into the sink behind him, only to bring the razor back to my throat, and scrape it across again.

It felt heavenly… just heavenly. I had almost fallen into another trance, when Close’s voice shook me to consciousness again.

“I’ll be honest with you, kid… *sigh*… When I was in the Guard… I was a model soldier.” ‘I guess it’s story time.’ “I never did anything that wasn’t for the guard. In my free time I’d run, workout, polish my armor, run drills in my head.” His razor made its final pass down my throat, and I soon felt a hot washcloth wiping over my cleanly shaven face and neck. “And for the longest time, I never went out drinkin’ with the boys, never got myself a gal, never… relaxed… and if it wasn’t for one single person… I never would have.”

My smock’s buttons clicked open, as the cover was pulled from me. I got a good look in the mirror… I looked damn good. “And, who was that, Close?” I was only half-listening... I just wanted to be polite.

“The fuckin’ Princess herself… When she’d noticed I was working too hard, she put me on a mandatory sabbatical. It really forced me to… get out.”

I trotted over to my saddlebags and pulled out my wallet. “How much do I owe you?”

“Huh?... oh, uh… fifteen bits.”

“Fifteen!? For what?”

“A trim, a shave, and sage advice… total comes out to fifteen,” he stated very matter-of-factly.

“You charge for talking now?”

“Hey If you get to, I get to.”

I handed him ten. “Keep the change.” I made my way out of the shop.

“Ingrate!” He shouted after me, chuckling.

Close is a really great guy. Rough around the edges, sure, but he’s really nice to me. He’s like a little slice on Manehattan, right here in Ponyville. Everyone here is reserved, cordial, polite… it’s annoying. In Manehatten if somepony has a problem with you they’ll tell you to your face... shout it to your face, even. There’s never any undue kindness or courtesy; if you’ve got a problem with somepony… fuck ‘em, let them know about it. Here it’s all… fake smiles. Nopony wants to look like they’ve got a problem. Nopony wants to screw with the perfect little town’s perfect little image.

Close is crude, loud, and an enormous ass; it’s a nice little breath of fresh air for me. In all honesty I’m a little surprised the ponies here actually go to his barber shop. I’d figure he would be a little too… colorful for them. He’s the very spirit of a Manehattan, he doesn’t care what people think of him… except his wife. He doesn’t sugar coat anything, he’s vocal about his opinion no matter the circumstance. He shouts and swears and tells dirty jokes no matter who’s in the room; and, to top it all off, he just leaves porn lying around his waiting room.

I’m serious. Whenever he’s got other customers I’ll flip through a Playcolt, or something in the waiting room. They’re just sitting on a table in there. Every now and then some kids will sneak in to sneak peeks at the magazines. He pretends not to notice for the most part, and if anypony says anything he plays the ‘my eyes ain’t what they used to be’ card; I’m fairly certain his eyes are better than mine.

He’s just so... real, nothing about him is anything less than genuine, which is more than I can say for myself.

Well, anyways, I headed further into town to finish of my chores. I figured I’d stop by the market early, before it got too crowded, you know?. The rain was starting to pick up again; the drops were small so it almost felt like mist. It was really nice, actually. I’d brought a hooded coat, but honestly I didn’t feel like wearing it. The rain felt good.

The market was just being set up, all the little ponies laying out their fruits and vegetables, pies and pastries, crafts and knick knacks for ponies to buy. The Ponyville market reminds me of the Farmer’s market that they set up in Manehattan, only smaller. Smaller however does not mean worse. The produce here is… superb. Asparagus? Green and flavorful. Carrots? Crunchy and delicious. Apples? Perfection.

Nopony really paid me any notice, which was nice. Everyone was too busy setting up shop. I made my way over to my first stop: Zecora’s stall. Zecora doesn’t come to market often, but when she does, I always make sure to meet her. She sells what is possibly my most important provision: birth control potions. A necessity for escorts.

Honestly, she doesn’t have a stall so much as she has a cart, but it is a sight to behold. It’s a rickety looking thing, to be fair, but it’s covered, absolutely coated in phials, bottles, gourds, and pouches of every shape, color and size imaginable. They’re all filled with powders and potions and concoctions for every problem a pony could possibly have. Bad knee? Drink this tea. Liver trouble? Mix this with your bathwater. The medicines and potions here are amazing. The mare behind the cart however, she’s absolutely stunning. She’s just so… exotic: her mohawk, her jewelry, and of course… her stripes.

Okay, lemme just say… I totally have a thing for zebras. I’ve had a few as clients, and I just find them… exciting. Everything about them, their coats, their manes, their body movement, even their words are just so… purposeful. There’s just some intangible air about them that’s so… poised?… elegant?… disciplined? Whatever it is, it’s dead sexy.

“Aaaah, is that Guilty I see? I think I know what brings you to me.” She smiled at me as I walked up. Luckily Zecora doesn’t seem to have an reservations with my career, either. Never has a bad word to say.

“Hey there, Zecora. How’s my favorite zebra?”

“I am well, Mr. Pleasure, and it seems you are too. I believe I have some potions for you.” I love the way she talks. I don’t just mean the rhyming, either. Her voice is just so… effortlessly sexy. Every syllable is thick with that accent and just dripping with sultry goodness.

“Thanks, Zecora, I just ran out, actually.” I twisted my head around to reach into my saddle bags and pull out my bits.

“Somepony’s been a busy boy. You must bring many mares joy.” She chuckled slighty and starting pulling a case of familiar blur vials from the depths of her cart. It’s like a honeycomb, each little slot holding a corked phial in its padded cell. “A hundred phials for Mr. Pleasure, here’s your case of ‘Escort’s Treasure.’”

I counted out 25 bits and handed them over. The price is almost criminal. Four for a bit? I feel like I’m robbing her. I used to have to order these through catalogues, they cost almost five times that. But Zecora insists that it’s an easy brew and that she wouldn’t feel right if she charged any more. Sexy and a heart of gold.

“You’re a master of your craft, Zecora. I’m in your debt.” I wedged the case of potions into my saddlebags. It was a big case, but it still fit.

“Please, Guilty, I’m happy to aid. And how can you be in my debt if I’m paid?” She chuckled again, and smiled at me. Her gaze seems permanently half-lidded… eternal bedroom-eyes. Maybe it’s just me… maybe it’s just when she’s looking at me.

‘Skies above, she is HOT.’

“You say that, Zecora, but you do so much for me, I’d feel bad if I didn’t pay you back in some way. I wouldn’t be opposed to a little… barter, if you catch my meaning.” It’s not often that I actually make a point of seeking clients out; I usually just let them come to me, but like I said… I have a thing for Zebras.

She feigned shock. “Dear me, am I being seduced, or are you just trying to get prices reduced.” She chuckled a third time… Heavens, even that laugh is sexy… so throaty and rich.

“Both.” This time I chuckled.

She smiled again, but… but it wasn’t the same smile. There was something else there. Only for the briefest of moments there was a slight flash of… disappointment? Frustration, maybe?

“Perhaps, Guilty, I shall... someday. But such a time is... far away.” I’ve tried to get her to visit me a couple times before, and I got similarly cryptic responses. Nothing’s ever overt with her. I know so little about her; but honestly, it just adds to her mystique.

You know for as much as I… how shall I phrase this delicately… have a massive hard-on for Zebras, I have a limited grasp of their culture. ‘I might have to pay that Library a visit if I have the time, grab a book about zebra culture.’

“Well, the moment you get the chance… just write me, and I’ll make sure my door is open.”

“I Thank you, Guilty, you are too kind, a shining example of Ponykind.”

“Well let’s not go that far.” I laughed, and we said our goodbyes. I would have loved to stay and talk with her a while, but it just wasn’t in the cards. After all, I still had lots to do today.

Next I needed groceries, easily the most awkward chore on my list. After my little trip to Zecora’s cart, most of the other stands were set up. The thing is, most of the mares here are, or have been, clients of mine. Lots of the framing mares here are hardworking, single girls, the kind that are ‘too busy for a boyfriend.’ They tend not to, however, be too busy for me, which makes shopping in the market… pretty weird for everyone involved.

It takes a truly great escort to completely separate his personal and professional lives. To be able to see clients without thinking about all the dirty things you’ve done with them is a fantastic skill. It just happens to be one that have yet to master.

Shopping here just fills my head with sessions I’ve had. The girl who sells asparagus always blushes when I walk up, gives a meek hello if nopony’s around. Every time I see her, I can’t help but think of the time she had me in hoof cuffs, straddling me, bouncing up and down on my fleshy rod, tongue lolling out of her mouth as she came again and again. I’m not that into bondage, but that was a great session.

The radish girl on the other hand is very vanilla. We don’t even go all the way a lot of the time. She likes someone to talk to as much as she likes the sex. She’s started working the stall lately since her father decided her pretty face could draw in customers. She always has so much to say about her family, her job, her kid brother, and of course about her radishes. When I walk up to the stall though, she’s all business. Never shows any indication that she knows me, never gives anything more than a polite ‘hi,’ that’ll be 4 bits, have a nice day.

Honestly I don’t hold that against her, and I’m not upset about it. If she showed any familiarity with me, anypony could jump to the conclusion that she’s a client. Manehattan is a very different place. Sometimes it feels like you could walk the streets your whole life and never see the same person twice. Here, though, everypony around you is a friend, an acquaintance or a co-worker, so I can’t expect her to be acting all buddy-buddy with the town whore.

In some ways it’s preferable to have a client act like they’ve never met you, because that alternative can be... worrying. Sometimes clients want to be… more than just clients. Whether they’re looking for a boyfriend, a shrink, or just a fuck buddy, a client that’s looking for more is just… never a good thing.

Back on the subject of market girls, though, the most awkward by far, though, is the cucumber girl. It’s not as though she’s particularly touchy when I walk up, or treats me like I’m not there; it’s just… we’ve done things with her cucumbers. Walking up to her and buying vegetables that I’ve… used on her. I don’t know it’s just… I can’t help but think about things. For the most part we both just blush and exchange money and veggies. I always make sure to stop by her place when she’s not busy so nopony sees us turn red as tomatoes.

The stalls run by stallions are a mixed bag. I haven’t taken any male clients… at least not in Ponyville. So there’s nothing to get embarrassed over. The guys around here react to me in one of two ways. Mostly stallions in Ponyville feel threatened by me. No that’s not me being vain, a good number of husbands and boyfriends see me as a threat… a... home-wrecker if you will. They just tend to look down their nose at me, and shoo me away from their girlfriends or wives or whatever. Now I don’t blame them, at least not completely. There have been some pretty nasty rumors about me spread through town. They paint me as some kind of seducer incubus luring innocent mares away from their families, which is… whatever. I don’t pay rumors much mind anyways.

A few stallions around town however almost have a certain… adoration for me. It’s weird to think about, I know, but occasionally I get guys coming up to me and like… looking up to me. I mean… I’m flattered, but it mostly just weirds me out.

The guy who sells plums is kinda like that. His name is... Autumn Wind or something. He’s a really skinny little guy, about my age. He’s got this super nasally voice, too. He’s a nice enough guy, he always gives me a couple extra when I buy a lot of plums, but he’s still kinda creepy. He’s just always smiling at me, and always asks if I have any advice on picking up girls. I always tell him that I only know what to do with women once I get them, I don’t know how to pick them up. It’s not exactly true, but he doesn’t need to know that.

Sometimes, though, this guy gets EXTRA weird and starts asking me for advice for the bedroom. Now in and of itself that’s fine…ish, but he just gets WAY too descriptive. I mean, I’ll be buying fruit from the guy, and he’ll ask me if he’s, and I’m quoting here, “giving his girl’s clitoris enough attention during oral, because he’s not sure if he should focus on tongue insertion, or exterior stimulation.” Now, not only is it just a weird thing to ask right out of the blue, It’s just so… clinical.

I dunno… he’s weird.

My last stop today was by far the most… interesting, though. Carrots. The carrot stand is (surprise!) run by Carrot Top. I tend to wait to get my carrots till later in the day since she trades places with some other mare who I haven’t had as a client. Today however was shaping up to be a very busy day, so decided to stomach buying carrots from one of my least favorite clients.

There’s no tension in the air buying from her, just… I almost want to say anger… contempt is a better word for it. I walked up to her stand, there was no line at the time, so she saw me coming. There was a smile on her face until she noticed me; after that it just vanished... melted. She just started wrapping up a bundle of carrots... expressionless. It was clear that she just wasn’t a fan of mine, and honestly I’m not much of a fan of hers. There’s a sort of unspoken agreement between us. I don’t like her, and she doesn’t like me, but sometimes we rely on each other’s services; so we just play out roles and get it over as quickly and painlessly as possible.

Just as I was about to hoof her my bits something… unexpected happened.

“HEEEEEY… GUILTY… GOLDY!” A voice shot through the market. I turned my head around to see, even though I recognized the voice immediately. ‘Derpy?’

Sure enough that cross-eyed Pegasus was galloping over to Carrot Top and me with a big smile on her face. She came to stop beside me, breathing heavily. “Hey Guilty I… *huff*… I saw you and I just… *huff*… just wanted to say hi… *huff* *huff* *huff*… HI, GUILTY!”

I was honestly at a loss for words. My first reaction was to say ‘HI’ right back and start a conversation. But… but what was Derpy thinking? I mean… everypony could see her… hell everypony was looking at us after she shouted to me like that. I looked around, sure enough there were some ponies gawking in horror as their beloved mail mare rubbed elbows with the local boy-slut.

“Oh… *huff*… by the why, Guilty… *huff*… this is my friend… *huff*… Golden Harvest.” She pointed a hoof at the mare I knew only as Carrot Top. “She’s… *ahem*… probably my best friend in the whole world.” She looked over at the salesmare with a big smile.. “Hey, Goldy… this is Guilty… he’s that guy I’ve been seeing on Sundays.”

Terror, that was the only word for her face. Clearly for C-… Golden Harvest (and myself) worlds were colliding. At first I thought she was just horrified that Derpy visited me, but her fleeting glances toward me told the whole story. She was afraid I’d spill the beans and tell Derpy that she was a client. As if I’m that rude. It only took a single sentence to destroy any of Carr-… Golden Harvest’s fear.

“It’s a pleasure to meet you Miss Harvest.” Cue the perfect handsome smile. I’d really rather not put on an act for Carro-… Golden Harv-… No I’m just going to call her Carrot Top. Carrot Top’s quickly caught on to my act, and started one of her own.

“Nice to meet you too, Guilty.” She’s a decent actor… apparently; I almost bought it. “Derpy, when you said you were seeing someone I assumed you meant a psychiatrist, not…” She just sort of gestured toward me.

“Meh, Guilty’s just as good as a shrink… better even; shrinks don’t make me feel so good.” She punched my shoulder playfully.

“Hehe, well I do my best, I suppose.” I was still sort of in shock. ‘Derpy… friends with Carrot Top?! And not even just friends, Best friends?! I don’t… I can’t even Process this.’

“So whatch doin’ Guilty? Buyin’ carrots? Doesn’t Goldy grow the best carrots? Hers were the ones I used in my carrot cake muffins.” I remembered those muffins, not her best work but spectacular nonetheless. They had walnuts in them, I think.

Muffins aside, I just wanted out of here… I couldn’t even begin to understand how the two of them could be friends when they were so… different. “Is that so… well… I should get going; I have lots of errands to run, still.”

“I got time, I’ll go with you.” Derpy beamed at me… damn it all, I didn’t want her to be seen with me... for her sake. But... I couldn’t say no to a face like that.

“Uh… Okay, Derpy.”

“Where to?”

“Barnyard bargains.”

“Oh neat-o, I need stuff there too.”

So, the two of us left Carrot Top’s stand. She glared daggers at me as I left.

“So what’s going on, Guilty? I never see you in town.” She trotted alongside me, oblivious to the wide-eyed stares and bewildered expressions of the townsponies.

“I could say the same for you. But, uh… yeah, I don’t come into town very often… I’m just… grabbing the essentials… you know.” All the ponies staring at Derpy... i dunno, it made me nervous... i was worried I would destroy her reputation.

“Yeah, I gotcha… I just took a personal day, I’m usually busy most of the week.” For a while we walked in silence. It was... nice. It was a bit chilly, but far from uncomfortable. The ground was damp and cool, but not unpleasant underhoof. The air continued to mist.

A curiosity began to creep up into my mind. I had to know… I just HAD to know how Derpy and Carrot Top could possibly be friends. “So, Derpy… How do, uh… How did you meet Ms. Harvest?”

“Hmm? Oh, we’ve known each other since we were fillies.” ‘Go figure.’ The two of us walked through town to barnyard bargains. “It’s kind of funny… she actually used to make fun of me for my eyes.”

“Yeah… kids are like that.”

“Well anyways… one day I’d had enough and I… well I bucked her in the ribs.” ‘Like mother like daughter, I guess.’

“HA!” I whooped, drawing the eyes of ponies all around. I immediately regretted my outburst, I should have been paying more attention to my surroundings, for some reason I’d stopped altogether. Not listening for my name on the whispers around me… stopped noticing clients everywhere I went.

Ugh… what is wrong with me?

Anyways, Derpy just giggled at me and continued her story. “Well, I ended up bruising her rib; and she had to go to the hospital. My parents made me go down and apologize, so I did. When I did she… she said that she was the one that was sorry. Said she was just doing cause some of her friends were, and that she felt really bad about it. I said it was fine… which it honestly was, I’m not really one to hold a grudge.”

We reached the front doors to Barnyard Bargains; I held the door for Derpy and followed her inside. Who says chivalry’s dead? I love stepping into that air-conditioned grocery store. Even on a cold day like today, the air conditioning feels really good.

“So after that we were friendly-ish… we’d say hi… eat lunch every now and then. ‘Every now and then’ turned into ‘every week’… and, before too long, into ‘every day.’ Eventually we were just... kind of inseparable.” Derpy grabbed a cart; I didn’t. I was only there for one thing.

“We got along really good for a while... but eventually we drifted apart, you know how it goes. I got married… had a kid… she was still working on her parents farm, we just… never had time for each other.” Derpy swallowed hard. “Things uh… things changed when… well you know. I was between jobs at the moment and… and I got evicted from my place… couldn’t, uh... couldn’t afford the rent.” Derpy started weaving her way through the aisles, picking up a few things as she went: eggs, butter, flour… muffin necessities.

“Anyways, Goldy put me up for… months. Dinky and I slept in her living room. She never once asked for rent or anything. I… *sigh*… I don’t even want to think about where I’d be without her.”

It was all… very weird. It just… it wasn’t the Carrot Top I knew: the… empty mare who visits me when she’s desperate for pleasure. I didn’t… still don’t… know what to think. Maybe the side Carrot Top shows me is the side she hides from the rest of the world; maybe she uses me as an outlet. Maybe the opposite is true, maybe she’s always putting on a mask for the world, and she’s only ever herself when she’s with me. Hell, maybe Derpy’s the only pony she’s ever nice too.

In my daydreaming, I almost missed that we had made our way to the most important aisle in the store.

Breakfast cereals. Cardboard chests filled with sweet golden sugary treasure lined the shelves. Heavens, I love cereal. Anything with marshmallows or crunchy sugary morsels I’ll just devour. I’m particularly fond of these new Peanut-Choco puffs they’ve got now. I grabbed four boxes, I plan on rationing them out till my next visit into town.

Derpy took notice of my choice, and giggled. “Those are Dinky’s favorite.”

“Your daughter has taste,” I joked. Derpy laughed at that, and grabbed a box as well. We were both just about done, so we made our way to the register. That was really awkward. The cashier is a client of mine, every few months she comes in and well… she likes to dress up like a maid… likes me to discipline her when she messes up. You know that sort of thing.

Anyways that’s probably why she referred to me as “master” when she rung me up. She was mortified. She blushed more than… well more than Twilight did. Derpy broke into a fit of giggles; I think she figured out what had happened. I managed to cram the cereal into my bags alongside all my fruits and veggies, which were now full to bursting… luckily the only other things I really needed to pick up were small. Derpy finished up with the cashier, too, as I was cramming my cereal into my bags. Whatever she said made the cashier blush ever more, and smile.

I’m glad Derpy gets along with everyone.

We said our goodbyes and Derpy set off towards home, to make lunch for her daughter. I, on the other hand, was hoping to replace one of my favorite oils; so cantered over to the nearby spa.

Aloe and Lotus are a couple of really nice mares. They own and operate Ponyville’s only spa. They came to me as clients once… together. That was a fun day. Anyways, after a brief chat I picked up a fresh carafe of oil, and a dozen Nag Champa (whatever that is) candles. They weren’t really what I was looking for but they smelled awesome, so I got them anyways. I was originally opted out of a massage though. I was feeling tired; and something told me if I lay down, I’d knock out. So off I headed with my saddle bags all but full-to-bursting to my last stop. Luckily It meant I got to take something out of my bags.

Ponyville has a tiny little post office, and the guy behind the counter is kind of a jack ass. But hey, not everypony on my little tour of Ponyville can be the nicest pony in the world. He’s a persnickety little old guy, probably born here. Luckily I’ve got all his little rules memorized. He’s such a control-freak. 6-stamps for a package of my weight. Address always written just so. Brown paper and twine only. No small talk. Stand in line and wait to be asked to approach the counter, even if there’s nopony there.

And there wasn’t anypony there by the time I got there. The sun was starting to set, and the rain was falling pretty hard at this point. I was grateful for that… waiting in line at the post office is agonizing. I can always feel everyone staring at me. It’s worse than just walking around town… it’s not like I can just keep going until their out of sight. I’ve gotta wait there.

Anyways none of that tonight, I was in… out … simple. My hard earned bits would be in Manehattan soon.

I was finally done with everything. Groceries bought, oil and candles acquired, payment sent, and potions purchased. All in all, it was a fairly productive day. Productive and exhausting. Not only was I carrying a bag that must have been sixty pounds, but I’d also been walking all over town since this morning.

It was then that I made a foolish decision. I let my baser instincts win out over my logic and reason. I failed to analyze the risk involved, and my actions led me into a situation I deeply regret.

I decided to grab a snack.

Now normally I wouldn’t be making so much drama over a little bite to eat, but… well I’ll just get right to it.

It was getting dark, the sky was clinging to the last bits of the day. The rain was really starting to fall. I was cold, sore, tired, and hungry. So, I decided (being the moron that I am) that I’d stop by Ponyville’s little bakery for a quick snack, to tide me over till I got home and made dinner.

Sugarcube Corner, It’s called. It’s a neat little mom and pop shop, I like it well enough. The weird thing is, they don’t make any bread. It’s all cakes and sweets and doughnuts, tasty stuff too. Not at all like my Father’s place.

I cannot believe I just wrote that.

Ok, something is officially the matter with me, lately.

Anyways…

There wasn’t much of a line, barely any ponies at all, just like the Post Office. Everypony was home, warm and safe from the rain.

As I walked in, I was soaked… and freezing. The ovens must keep that place fairly warm, because it was nice and cozy when I stepped in. It smelled like frosting, too. It’s kind of a… rustic little place: wooden tables, wooden chairs, nice hoof-made looking stuff. It’s really nice looking. It’s got a little display case filled with cupcakes and such. All of it looked scrumptious.

The girl behind the counter was… let’s just say “lively.”

“Hi, What can I get for you? Maybe a cupcake? Or maybe a scone? OOOH, I know… a bear claw! You ever wonder why they call them bear claws? I mean they don’t really look all that much like a real bear’s. *GAASP* Maybe there’s some kind of pastry bear out there that has claws like that! Oh I’d love to meet him! I wonder if he’d like a bearclaw.” She was a pink ball of energy. Pink coat, even pinker mane, a little bit chubby… she was kind of cute.

“He would probably already have a few,” I said. I was really just trying to get a word in edge wise.

“Oh YEAH! Anyways, what can I get you, Guilty?” She had the most innocent smile on her face.

“Lemme just get a… wait did you say Guilty? You know my name?” I shouldn’t have been surprised as I was… I mean I am topic of much gossip. Either way her answer was interesting.

“Uh-huh! I know it from when you first came to Ponyville! You told me.”

“I did?”

“Yes indeedy! You came in and bought a donut and some coffee, we talked for a little bit. You told me you were opening a business in town. Which is weird because I was looking and looking and couldn’t find any new stores open in Ponyville or anything. I was so sad too, cause once I found it I was gonna invite you to a ‘Welcome to Ponyville’ party, but when I couldn’t find you I just thought you might of left town without saying goodbye and then I got even sadder. But then you walked into my shop right now and I got so happy and I asked what you wanted and then we started talking about bears!”

“Ok then.” I’m pretty sure I was just staring wide-eyed, amazed she’d managed to fit that many words into just one breath. “Wait, you were gonna throw me a party?”

She nodded “Yep, I throw everypony who comes to Ponyville a welcoming party… that’s how I’m friends with everypony in Ponyville!”

“That’s awfully nice of you. But I think it might be a little late for me to be welcomed to Ponyville, It’s been… jeez almost two years now.”

“That’s okay, there’s always a reason for partying… I can throw you an ‘Almost Two Years in Ponyville’ party!”

‘Oh please, no.’ “Oh, that’s fine, please don’t trouble yourself… besides… I’m not much of a uh… party guy.” I shuddered. Honestly the last thing I wanted was to call attention to my presence, a party would just… no.

“I getcha. But if you won’t have a party at least let me buy you something.”

“Uh, sure… how about that cannoli, there.”

“No problemo, that’ll be two bits.” She stood smiling. There was an awkward silence for a few moments.

“Uh… I thought you said you were gonna buy it for me.”

“OOPS… sorry. I forgot.” She got all embarrassed, too cute.

Anyways she rung up the purchase, and I took a seat. Most of the tables were free, just a couple other ponies dreading the wet walk home, enjoying the warmth of the bakery. I didn’t pay them any mind, and they seemed not to notice me particularly. It was a good cannoli too, even if it was a bit too sweet for me. I don’t normally have that much of a sweet tooth. (Cereal doesn’t count!)

I was thinking myself pretty lucky… here I’d met another pony in town who doesn’t mind my presence. For the most part I’ve managed to get my errand routine down to ponies who don’t HATE my guts, and here was one more. ‘But wait… does she know what I am?’

Before I had time to consider this fact any more, the doors swung open, with a loud bang. I snapped my head around instinctively.

It was her. The mare who brings the most trouble to my life. I had almost gone the whole day without seeing her. If I’d only just made my way home, I might never have had to deal with her. I must confess: I hate her more than anypony else in Ponyville; I’m sure she hates me just as much. She’s the reason I don’t live in the town proper, she pushed more than anypony to get me kicked out. She has a lot of influence in town… ponies seem to look to her in guidance. So when she started trying to get me kicked out of Ponyville, others soon joined her.

“Hey Applejack!” The cashier girl shouted at the dripping pony.

“Landsakes! Rainbow Dash an’ all them sure did a number on the weather.” She pulled the damp Stetson hat off her head and gave it a good shake, only to place it back on her head. “Hey there Pinkie… How y’all doin’?” That drawl... I’ve come to loathe that drawl.

“I’m great! The other day Pound Cake was…” I stopped really listening. At this point I was mostly concerned with finishing my Cannoli without getting spotted. I slowly moved my back to the counter, just praying that fucking mare didn’t glance my way. I was holding as still as possible, just trying to draw no undue attention.

It’s not as though my life depended on it or anything it’s just… she always… always goes out of her way to give me a hard time. What I do… bothers her, and wasn’t sure why. Whether she’s running her little stand in the market, or just sees me on the street, she just… chews me out. I usually just walk away, but recently she’s taken to following me for a bit.

Applejack and Pinkie got to chatting, but I was only vaguely aware of their conversation… one of them mention Twilight at one point, and that’s what caught my attention. “So Twah and her new bo are gettin’ along? Well that’s mighty good to hear.”

“Uh huh! The other day they were… *brrrrr*” Pinkie’s teeth started chattering audibly.

“Wha’s the matter Pinkie? Chilly? Maybe y’all should put on a coat.”

“No, I’m okay... I just got the willies right now… which is weird cause I never get the willies unless someone’s gonna start a fight.” ‘What??’ I wasn’t quite sure what to make of that.

“Don’ worry Pinkie, I don’ think any of these fine ponies are gonna go an’…”

I could hear it… I could hear her noticing me. I could feel her gaze on my back. I just tried to shrink… hoping that she would just… un-see me… that I wouldn’t have to sit through her ranting and shouting and insults.

“Ah’d recognize them fancy jeans anywhere.” ‘Damn my impeccable sense of fashion.’

She trotted up behind me… I was determined to ignore her. I didn’t turn to face her, and didn’t say a word. I just kept biting at my cannoli. “Now what I wanna know is… what makes y’all think it’s okay to come in here.” Her voice was low and calm… for now, that would change.

“A-Applejack… what are you…?” Pinkie was trying to say something, but her voice was barely above a whisper. Applejack paid her no heed. I was sure the everypony had their eyes locked on us at this point.

“This is a decent, upstanding, family-run establishment, and yer… yer just sullyin’ its good name settin’ hoof in here.”

‘You…’

“Why don’ you just go one home, back to yer little shack… OUTSIDE Ponyville.

‘Insufferable…’

“Fer that matter, why don’ y’all just go back to Manhattan where y’all belong.” Her voice was starting to pick up volume.

“Applejack, What the HELL!?” So was Pinkie’s

‘Impossible…’

“We don’t want y’all here in Ponyville.”

“Bitch.”

There was a long pause. I realized that I had said that last part out loud.

“…What did you say?

‘Well, I guess I’m committed now.’ Truth be told I’ve been wanting to tell her off for quite some time, I’ve just never… let myself get mad enough. My little slip, though, had put me in the thick of it. If I stopped then, I’d have been a coward.

I am not a coward.

I stood up, and turned to face her. She was… eight kinds of mad. She was just… seething.

“Applejack...” I shrugged, I could only think of one way I really wanted to say this. “... you’re a fucking bitch.” Her eyes went really wide.

“I haven’t done shit to you. But you… you hassle me every fucking chance you get.” I tend to swear a lot when I get riled up. “What the fuck is that about?”

I caught her off guard if nothing else. I’d never actually said anything back to her; so, for the briefest of moments she was surprised. She recovered quickly enough.

“I… I aint gonna sit here, an’ be talked to like that by… by a dang slut!” That’s one of her little pet names for me.

“Oh, real fucking original, bitch.”

“Don’t you DARE call me that agin’ you… you…”

“Are you out of insults already?”

“You… you… home-wrecker! Why don’ chyou just LEAVE?!”

“I haven’t finished my cannoli yet!” I smirked at her… mocking.

That… Okay, I’m not proud of how I acted… but she… she pushed me… had been pushing me… for months! But... but I… got pretty… pretty immature there…I... fuck… I’m an ass.

But that wasn’t even the worst of it.

I’ve been watching Applejack a lot, mostly when I’m trying to avoid her… but… I’m an observant guy. Even at the worst of times I… notice things.

“Jus’ GIT.”

The ways she says certain things. It’s always… we don’t want stallions like you here. She always calls me thing like home-wrecker, sometimes asks me if I’ve broken up any families today. As far as I know I haven’t actually destroyed any relationships to date. On top of that before she even met me, she’s been out for blood.

“We don’t want y’all here in Ponyville.”

And one thing that she never ever calls me, despite that fact that she has every reason to… is a whore. It’s like she doesn’t even want to say the word. I was… I was 90% sure she’s had a whore fuck up her parents’ relationship. I’ve never seen them, and when you spend as much time as I do listening to what everyone around you is saying, you pick up on a few things.

“We don’t any want stallions like you in Ponyville!”

And… and I just wanted to shake her up… I just wanted to rattle her. Just shut her up for a moment... to get the tiniest of breaks from her... everything.

So I just said:

“Why’s that, because your mommy left your family for a whore?”

I knew it had to be the mom. I knew because of her hat. That’s a hat she cares about. I mean, it was soaking, right then, and she was still wearing it. There’s a hat rack in the bakery, she could have hung it up if she wanted, but no. She put that wet hat right back on her head. Also, I’ve read enough fashion magazines to tell the difference between a Stallion’s hat and a Mare’s. Since I doubted she’d treasure a keepsake from a parent that abandoned her, and I figured the hat must be her father’s. That could only mean that it was her mom that… well... did whatever she did.

It was a gamble to be honest… just a cold read, a shot in the dark, but the look on her face told me I was right.

She went pale, like she’d seen a ghost. I guess it had been years since anyone had even mentioned it, knowing this town.

I’d made an educated guess and found one of the skeleton’s in applejack’s closet At first she didn’t look like she wanted to believe I’d really just said that. When she tried to speak it only came out is hoarse whispers.

“That… that ain’t true.” Her eyes started to dart around the room… she’s a pathetic liar.

“Please, It’s written all over your fucking face.” I was snarling... growling, even.

“I… I…” I could see the rage… the pent up anger… the fury brewing inside her. She was so…mad. She wanted to hurt me… I could tell. She wanted to give a black eye. She was shaking in anger, if only just. “I ain’t gonna stand here, and be talked to like that from A FUCKIN’ GOOD-FOR-NOTHIN’ STUD!”

The bakery was silent save for the ringing in everypony’s ears. All eyes on us. Half were probably waiting for my response, and the other half were most likely just surprised Applejack had exploded like she did... and used language like that.

I haven’t been called a stud in… ages.

That was crossing the line, for me… I wanted to shout back, call her… awful things. But… but when she… screamed like that I realized I’d pushed her too far… I was as much at fault as hers at this point. So I… finally… came to my senses. I just left. No parting insult, no caddy remark… I just… put up my hood and left. I even left what was left of my cannoli on the table.

As I left I could hear applejack crying, I think. That Pinkie girl was trying to calm everypony down.

I’m… I’m more mad at myself than her. I mean… she did start it, and she always does. That, and she did call me a stud. But everything she said was just… anger… just… blind rage. What I said… about her mom… it was… too personal. It was a low blow… super low.

I… I promised myself, too. I promised myself that I wouldn’t use my special talent like that anymore. I mean… I mean I can’t help but notice things… I can’t. Especially with someone who routinely makes a point of getting in my face. But…

But that doesn’t mean I had to act on them. I didn’t… I shouldn’t have said that… it was too... heavy. I… wasn’t composed… I let myself get angry… I…

I blew up, but that’s not even the worst part.

I… I was happy to. I was happy to verbal eviscerate her in front of… oh jeez, I just realized that that Pinkie girl must have been her friend. Well, looks like I can’t go back there again. But I just… I was… I guess I was just fed up. And probably not even with her, with everypony… with all the back talk, and gossip and rumors and hushed conversations.

Well… whatever.

Either way I still walked home in the dark, and in the cold, and in the rain, carrying 50 pounds of soaking wet supplies. When I did get home I just barged in the front door. I wanted to collapse, just lay down in my dark foyer and… sleep.

In the end though, I didn’t. I started putting everything away… each little sundry and grocery in its place. Until all I was left with was empty saddle bags… and soreness. The fruits and veggies seemed ok, after I dried them off. The cereal boxes were ruined, but luckily the plastic bags within kept the sweet morsels safe. What an end to a day that would have been. No cereal for Guilty.

I’ve been taking a lot of warm showers lately… I took another tonight. I didn’t bother scrubbing or cleaning or shampooing. To be honest that was partly because I was afraid I might have another episode. I just… lied down on the floor of my shower and let the warm water relax me.

It was nice.

I think… *sigh*...

I know… that something is up with me. I’ve been… out of sorts.

I keep… I keep forgetting myself. I keep letting my personal life slip, even in my writing. I lost my shit… I’ve been putting up with her harassment for a long time, and tonight I snapped? Not likely just a coincidence. And I’m not even going to get started on the scrubbing incident.

I… as I’m sitting here… writing… I can’t help but think about what Close was saying. I wasn’t really listening at the time. Well maybe it’s more like I didn’t want to hear him, but… but I think he’s right… I need a hobby or… or… something.

Maybe someday soon, I’ll stop by the library. Grab a book, not one for research or for some client… something… fun, interesting. Something for me to read just to read. I’m kind of wishing I’d taken the time to stop by there today. I probably had time for it.

Today, not unlike yesterday… had some good and bad. Unlike yesterday however, I would have to consider this overall… a bad day.

A bad fucking day, that I just want to be over. I’ve got to get up bright and early tomorrow for a client. If I recall I’ll need to prepare some restraints for myself... and some Aloe Vera. This mare likes to whip me.

When it rains it pours.

Odd Requests

Chapter 5

Odd requests

Dear Journal,

I’ve been thinking a lot about Close’s advice these past couple of weeks. I’ve decided that I need a hobby. I spend too much time working. Now, I don’t mean time I spend with clients, that usually comes down to less than a dozen hours a week. I mean all the research and grooming and tidying and exercising I do in preparation.

Not that I shouldn’t be doing all of that. I definitely need to stay in shape. My body is a temple… and my chief source of income, so it needs maintenance, and grooming. My place needs to be tidy for guests too, so I can’t exactly stop that, either. And research? Well… I might spend a bit too much time trying to have conversation topics prepared… especially when half the time I don’t even get the chance to use them.

But, no, what I mean is... I need… something else. I need something I can do that really gets my mind off of work and... honestly I dunno. But ever since I talked to Close I feel like something’s missing. I mean... right now, I really don’t have much going for me aside from my job. I’ve been trying a few things out, to be honest.

I came across an old mystery novel while I was tidying my books. It was… fine… I guess… not really all that interesting to be honest. It’s just not my thing, apparently. I have a little wooden chess set lying around. I played a few practice games against myself. I think if I want to play any sort of game I need someone to play with, because that was boring as hell. I even tried my hoof at origami… Clearly a practice designed by a species gifted with something more that hooves. Needless to say my garbage can is currently filled with a horrid mess of crumpled paper.

I guess… I guess I don’t really know what I like… I’ve never really had this much free time. I mean, not since I was a kid, and I’m sure as hell not going to start doing… well anything I used to do, really. Thinking on it I was really a horrible little urchin. I still can’t believe how much I used to do. Stealing… tagging… pranking cops… I was a little shit, quite frankly. All up until I got that job at the stable, really.

And there I fucking go writing shit down without realizing again! That shit’s only gotten worse! In Derpy’s last couple of visits I’ve mentioned both the stable, and my father. In one session with an every-now-and-then, she asked me off-hoof about that scar behind my ear. I... I almost told her. I actually considered telling her. I just… just… I don’t even know.

It’s like… it’s like I’m… unraveling. Like all the work I put into being… Guilty is just… coming undone. Like all the pomp, illusion and effort I put into my persona is just… giving way… and soon all that’s going to be left is... what? I’ve been Guilty Pleasure for a long time now. What happens if I let something big slip? What happens if everyone finds out all about me? What happens if I start breaking down in the shower more? Even worse, what happens if I break down mid-session?

Not that I actually think it’s going to get that far… I’m just… worrying.

I just… I don’t know how to be anyone else anymore. Guilty Pleasure used to be a mask… an act… an… an avatar. But now… I haven’t been that little bastard that used to steal and fuck around Manehattan just to avoid going home for, how long now?

Holy shit…

I’ve been Guilty Pleasure for ten years.

Where does the time go?

Anyways… my point is… My point is I don’t feel like I know how to have fun… I don’t even know what I find fun anymore.

That said, I got some very good advice about fun today, from someone I was not expecting. Maybe it will help.

When I got up this morning I was expecting another day free of clients. I had nopony scheduled to come in, and was… well… working out. Squats and sit-ups: building muscle mass. Now muscle mass isn’t terribly helpful in the bedroom past a certain point. I mean, it’s not like I have to bench press girls. That said, an Escort is expected to be... well... sexy; and muscles are sexy. I was a pretty lanky kid. So, I have to work to keep a good figure. I don’t go overboard... I really only work enough to keep myself from looking like a twig.

Anyways I was mid-squat when I got a knock at the door. As I mentioned I had not clients scheduled for that day… so I was thrown for a bit of a loop. ‘Is this a client? I didn’t have anything in my planner today. Did somepony come out all this way without writing first? That never happens!’

Rather than get up and answer, I opted to just call out from my spot on the floor of my foyer. “H-Hello?”

“Hi Guilty. Are you home?” The voice form the other side of the door was… so familiar. I could almost place it.

“If I wasn’t home, how could I answer?”

“Oops! Silly me,” she giggled. It was so… bubbly and cute and… lively, that voice.

“Hold on, just let me… *grunt*… get up.” I was sweating hard from my workout, no chance of making myself nice and neat this time. No time for pants, even. I grabbed towel, though... to take care of the sweat.

I dried myself off as best I could and caught my breath before I opened the door.

“Hello, how can I…. oh….” I was shocked to say the least. I honestly never thought I’d see her again. “Pinky, right?”

“Yup! And you’re Guilty!” It wasn’t a question.

“Yes… Yes I am. Can I… help you?” I was still wrapping my head about the whole situation. After my little… outburst in her shop, I figured I was the last person she’d want to see. But she was here… and clearly happy. Dear Princess was she happy.

“Uh-huh! I’m here to deliver a letter!” She produced a letter from her person. I’m… I’m honestly not sure where exactly she pulled it from, to be honest, but she hoofed it to me nonetheless. It was a pink envelope, sealed with a little yellow balloon sticker. When I opened the letter a tiny burst of confetti shot out at my face; Pinkie just giggled. I pulled out the letter itself, and unfolded it.

The letter itself read:

Dear Guilty,

I’m bringing you this letter to make an appointment for right this second!

Signed,

Pinkamena Diane Pie

I did my best to keep my jaw from dangling. “An appointment? Right now?”

“Yes indeedy!” She just stood expectantly right outside my house. Waiting for an invite inside.

To be honest I wasn’t prepared at all. I had no music playing, I was sweaty, I didn’t even have pants on. Even still, I really saw this as an opportunity. A chance to get on good terms with a potential repeat client.

And honestly... why the hell not?

“Come on in Pinkie, just… just let me shower off first.”

“Okie dokie lokie!”

I let her in, and poured her a glass of water before heading upstairs for a quick shower. I rinsed off lighting fast and met back up with pinkie downstairs. She was busy investigating every little knick-knack and whatnot in my foyer. I noticed that there were now some saddlebags lying by my front door… which is odd, because I don’t think she had them when she came in. “Sorry about that, you just caught me in the middle of a workout.”

“No pro-blemmo.” She just beamed at me as I came down the stairs.

‘This one never stops smiling does she?’

“Anyways, have a seat and we’ll begin.”

As… energetic as Pinkie was, I decided not to make tea, she hadn’t touched her water, anyways.

“So, uh… first question, is it okay if I call you Pinkie?”

“Well of course silly, what else would you call me? Pinkamena is too long, and sounds all boring.” ‘Fair enough’

“Very well. Now, secondly…” I was way out of my element… I wasn’t in character quite yet… I’d have to ease into it so she wouldn’t get suspicious. “...there is, of course, the matter of payment.”

“Oh, don’t you worry about that… I’ve got LOADS of savings and stuff.” Quick as a whip, she rushed over to her bags by the door, and came back with a handful of bits, which she swiftly hoofed to me. “Here’s forty, that’s two hours right?”

“Uh, why yes… yes it is.” This mare was more prepared than I was. I put the bits aside and continued with my inquiry. “Okay, next, how did you hear about me?”

“Oh, well that’s easy. After that whole mess in Sugar Cube Corner, which I am SO SORRY about by the way, I told my friends about what happened with Applejack… I mean not ALL my friends, that would have taken forever, I mean I know EVERYPONY in Ponyville after all. Can you imagine? But anyways, after I talked to SOME of my friends about it, just my really really really close ones, Rarity was all ’*GAAASSP*’ and asked if you were okay, and I told her you were fine, but I wasn’t sure where you lived, so I couldn’t check, but then it turned out RARITY actually knew where you live and she told me and I said ‘Oh ok I’ll go pay him a visit!’ But then Rarity was all… ‘Pinkie, Guilty might be with with client or whatever, you should make an appointment. So I said I would, and then SHE said I should write you a letter first to make an appointment, and I said ok, but what am I making an appointment for, and then she said you were an escort and I asked what that was, and SHE said it meant you go on pretend dates, and I said that was silly, and then I realized that meant I get to have SEX with you, and I asked how much is cost and she told me twenty bits an hour and then I wrote the letter and got the bits and came HERE!”

“Uh… okay then… thank you for that.... regaling. Wait a second, that whole fight was two weeks ago, what took so long?”

“I couldn’t find my stationary!” She exclaimed cheerily.

“Well I guess that explains that, then.” ‘This mare is something else.’ “So that brings me to my last and most important question… what can I do for you?”

“W-well…” For the first time since I’ve met her, she suddenly didn’t have a giant smile on her face and all the confidence in the world. She was embarrassed... slightly. “…well that’s… complicated.”

“How so?” Finally I felt like I was catching up to this girl. I finally had a little bit of a traction in the conversation.

“There’s this… thing… I want to try, and I’ve never actually… gotten to do it...” She was twiddling her hooves together, she was getting uncomfortable. “...because… I’ve never actually asked anyone if they want to.” She was beat red, staring down at the floor.

“No need to be embarrassed, Pinkie. What is it you’d like to do?”

“I want… I… Oh look at the time, I should get going, I have a thing I have to –“

“Pinkie… I’ve done just about everything you could think of. So please, just tell me what it is you’d like to do?”

She calmed down a bit, clients with odd tastes like to feel like they’re not the only ones with them… luckily they usually aren’t. “I… how about I just show you?”

“Okay.” I smiled my hunky smile… I was back in character at last… her being a little bit embarrassed put me back in my comfort zone to be honest… I’m used to comforting mares.

She trotted over to her saddlebags and brought them over to the table. She reached inside and produce a number of foodstuffs. She had whipped cream… three kinds of frosting… chocolate and caramel sauces… some strawberries… cherries… honey… and sprinkles. Once all of the food was laid out on the table she started ranting again.

“Okay, so when Rarity told me that you have sex for bits I kinda sorta hoped I might be able to try this thing I’ve always been too embarrassed to ask one of my boyfriends or girlfriends to do, even though I’ve always really liked the idea.”

“And that is?” I was fairly certain I knew, but I wanted to be sure… plus I wanted her to be the one to put the idea out there… It forces a client to get over their fears a little.

“I want… I want to eat off of you… while we do it. And I want you to eat off of me too.” She looked… unsure... shy... she’d steeled herself. She was waiting for me to call her weird, tell her it was a stupid idea, tell it was too freaky.

Honestly, the way she hyped it up I was expecting something… extreme.

“Is… is that all?” I’ve done so much freaky shit that food-play doesn’t even show up as a blip on my sonar.

“Huh?” She was flabbergasted.

“Well don’t get me wrong… I just… I thought you were so embarrassed because it was going to be something… weird.”

“Wha? Bu- that’s plenty weird!” She sounded sort of… offended?

“Don’t get me wrong, I mean… sure it’s unusual as far as kinks go, but… that’s not really that… shocking. You had me expecting something… extreme, I dunno.”

“So… so it’s really okay?”

“Of course… It sounds like fun.” Honestly it did… food-play is fun. I mean… eating is already something very… intimate… in its own way, and combining it with sex is very, well, pleasurable.

“So… I only have a couple rules before we start.” I began.

“Okie dokie lokie!” I started collecting our… toppings. She was already back to her bubbly energetic self. Practically bouncing as I led her to the bedroom.

“The first one is very important for both of us. If either one of us… at any point… says to stop… we both stop, no exceptions.” I explained.

“Gotcha!”

“And the second one is very important to me. At no point, may you ever kiss me on the lips.”

“Really? Aaaaw… smooching is so fun though!” She was disappointed, but not too much.

“It’s my only taboo… and I’m going to have to ask you to respect that.” Being clear in what is allowed and not allowed is very important as an escort. Hell, in any sexual relationship.

“Fine fine fine, I gotcha… OOOOH!”

She lit up at the sight of the bedroom, her eyes darting every which way and that. She buzzed all over the room, asking questions the whole way.

“OOOH OOOH, What in this bottle? Smells like lemons… mmmmmmm. OOOH, What in this chest?- *GASP* It’s so BIG! And Knobbly! OOOH, what are these books? OOOH, they’re full of sexy pictures. How does she bend like that? That looks like it would hurt. What scent are these candles they smell good. What in this chest? … I don’t even know what this is… it looks scary.”

“Uh… in order… That’s my favorite lubricant, honey lemon oil… that chest is filled with assorted toys... the big ones. That’s a copy of A new way every day: 365 positions for his and her pleasure. I have no idea how she bends like that. The candles are Nag Champa, I have no idea what that is, but yes… it smells good. And that…” I pointed to the twisted assortment of leather straps and metal in Pinkie’s hoof “…is a dental gag. It keeps your mouth open.”

“Neat-o! Can we try it out?” She was already trying to figure out how to put it on.

“I… think that would be a little… counter-productive.”

“Oh yeah, huh?” She tossed the gag back into its trunk and unceremoniously shut the lid.

I walked over to my potion trunk, and pulled out a blue phail.

“What’s that?”

“Birth control potion.” I downed it quickly. Not matter how many of those I drink, I will never get use to the flavor.

“Oh, so you don’t get my eggo all prego.” She nodded to herself.

“Um… yes?” I knew what she meant, I just… I’ve never heard it put that way.

I sat down on the bed. “So… how would you like to do this?”

“I have no Idea.” She was smiling when she said that. It was cute.

“Well, then do you mind if I take the lead?”

“Go for it, Guilty.”

I happily obliged. I started with the chocolate sauce. I squeezed out a generous dollop into my hoof. “Well then, why don’t we start… here.” I brought my candied hoof down between my legs, and began pleasuring myself. Each slow stroke made me harder and chocolatier. I pumped up and down my length, coating myself is the sweet syrup. Pinkie just watched me… for once, having nothing to say. Eventually my sugary stallionhood was throbbing, and Pinkie was actually drooling. “Look good enough to eat?”

“Uh-huh,” was all she could muster. She was transfixed on me. Her eyes following my hoof’s every movement.

I slid myself to the very edge of the bed, and presented myself to her. “Want a taste?”

She didn’t even answer, she just dove onto my cock. In one swift motion the entirety of my flesh was in her mouth, and she was eagerly sucking all the sauce off of it. ‘No gag reflex… holy fuck she’s good.’ She was taking me like a champ… honestly I’m not the… biggest guy out there, but still, it was impressive. She wasn’t just good, she knew what she was doing… she could’ve made me climax right then and there, but she kept me teetering on the edge, right up until she popped me out of her mouth.

Pinkie brought a hoof to my chest, pushed me back onto the bed and climbed on top of me. Her face… she was like a mare possessed. So much energy, and not her seemingly usual hyperactive energy. Just... raw intensity. This mare really got into it. She was breathing heavily… almost trembling. I could tell she was just so… excited. She quickly scooped up the foodstuffs form the floor and put them all in hoof’s reach. She grabbed the caramel sauce, and gave me a another vigorous coating. She’s great with her hooves too. Not to be rude, but I think this girl’s been around the block a few times… she must have to be this good.

Anyways after I was all candied up, she started another round of oral. Almost better than the first round. It was quickly becoming clear to me that once Pinkie got going, she liked to be in charge… which made things easy for me. After the caramel, she grabbed the honey… wanted to try my dick in every flavor apparently. (I’m sorry I wrote that.) She twirled around on the bed, and parked her hindquarters right on top of my face as she coated me once more.

Ok so… I think I’ve already written that giving head to a mare is my favorite thing in the world. But my favorite way to give head is face-sitting. I just… I really really love it when a girl sits on my face. It’s just… I can’t even explain… how much I enjoy that. And Pinkie’s ass was just so… big and… soft. So I couldn’t exactly pass up this opportunity now could I?

I reached a hoof out and grabbed the first food I found, which turned out to be the chocolate sauce again. I once more applied a large helping of liquid candy to my hoof and rubbed it all over her lady parts. She was already… sopping wet. We’d only just started but she was ready and raring to go. She didn’t say anything as I coated her either either, she was completely focused on coating me in honey.

Only after I started using my tongue did she say anything. “Oh… GUILTY… you’re… hehe … good… at that.”

‘So are you.’

She once more started sucking the delicious sweetness off of me as I licked all the chocolate out of her.

I would just like to say that I feel the sixty-nine is under rated. It’s a very simple position, yes, but it also happens to be completely amazing. Getting head is awesome… giving head is awesome… what’s not to love?

I came a while before she did. She pulled me WAY over the edge with that mouth of hers. Rarity may have some competition. “Mmmmm, Honey and come are good together.” I wasn’t exactly inclined to believe her, but hey, who was I to judge, I was busy enjoying chocolate mare.

She just straddled me while I finished her off (which honestly took a while) and boy was it loud. “OH GUIIIILTYYYYYYYYYYYYYYYYY!!” She positively shrieked.

She collapsed backwards, falling above my head. My mouth was all sweat and chocolate and mare… honestly not a bad combination, in a sort of bizarre way. I was content to just lie there, while Pinkie and I recovered. Something was bothering me though.

I was having fun.

And honestly that just pissed me off. ‘THIS is what I find fun… Sex… why can’t I find something ELSE fun? Something that isn’t my JOB? Why is it that I can’t have fun unless I’m with a mare?’ Pinkie’s pleasure soaked words pulled me out of my moping. I was just happy that she couldn’t see the scowl that had formed on my face from her position.

“That was…*huff*... you’re*huff*… I had… *huff*… awesome.”

“Having trouble with your sentences, there?” I laughed.

“Uh huh… *huff*… trouble… yeah.”

“You okay?”

“Yeah... *huff*...Pinkie… *huff*… keen.”

I rolled around to face her. She was sprawled out on her back… chest rising and falling as she gasped for air. She sat up, she looked hilarious to be honest… a face covered in all manner of sticky sweet, and a great big chocolate spot on her crotch. She bounced slightly on the mattress, testing it.

“Is this… is this bed a cloud?” she asked.

“Yeah, it is… you can tell?”

“Uh huh.”

“Normally only Pegasi know what it is.”

“Huh… well, I’ve walked on clouds before, so… I can tell.”

“You have?” That was interesting.

“Yup… my friend Twilight… she can cast a cloud-walking spell.”

‘Twilight can do that?… oh yeah, she actually mentioned that.’

“That’s cool,” I said.

“You bet it is… lie back on your back”

“Sure.” I complied. I just closed my eyes and let pinkie do as she liked. I have actually don’t have that many clients that like to take charge in bed, so it’s nice that Pinkie does. I heard the whipped cream can shake, and soon It was being used to coat my chest. I also felt a few things drizzling over me as well. “Turning me into a sundae?”

“Hehe, kinda.” For a few minutes I just waited while Pinkie decorated me like a cake. I mean really decorating me, whipped cream and strawberries and chocolate sauce, all with a cherry on top. It was… really sort of elaborate.

“Wow… you’re good at that.”

“Well I don’t work in a bakery for nothing.” Once she was done she hoisted herself above me once more, this time facing me, her hips above my already at-attention self. She eased her way down onto my shaft. The look on her face was priceless. Such a gigantic smile, her whole body quivering in pleasure. She was in heaven. I was enjoying myself but honestly not nearly as much as she clearly was. The warmth of her sex enveloped me as she bounced herself up and down on me. Soon she was licking up the toppings on my chest as she rocked back and forth on top of me, her tongue collecting up dollops of Whipped cream, scooping up strawberries, and lapping all the chocolate off of my chest.

I felt like I wasn’t really contributing, but hey, she was happy. Through all the pleasure, and sweating, and panting, and bouncing, and smacking lips, and slithering tongue, she managed to get a few words out. “This…*huff*…is so… *huff*… fun…*huff*… hehehe!” Eventually my chest was clean of any food, and pinkie was just licking at my coat. I don’t think she really noticed; she was too busy fucking herself silly on my rod.

Eventually she stopped licking me. She just clung to me as she gyrated her hips, panting into my chest, hooves wrapped around my shoulders. After several minutes she came. Her back didn’t arch and she didn’t scream this time. She just… clung to me… really tight as her hips quivered.

She just went limp after that, slumped on top of me her face buried into my chest. After a moment or two, I hazarded a question. “You, uh… you okay Pinkie?”

“Yes…*huff*… in… *huff*… deedy…” She weakly struggled to roll herself off of me. After a little help from me she managed to roll onto her back beside me.

“Do you want to keep going?” She was exhausted, but I hadn’t really done much, so… I was still fine.

“Nnnnno. I think I’m…*huff*…good…*huff*… you?”

“I’m fine, Pinkie… Did you enjoy yourself?” I turned my head to face her.

“What do… *huff*… you think?” She just stared off into the ceiling.

“I think you had a ton of fun.”

“Uh huh...*huff*…you…*huff*…you want me to…*huff*… finish you off?…*huff*…I don’t wanna…*huff*… blue ball ya.” She giggled at the phrase ‘blueball’

“No, I’m fine, Pinkie… thank you for offering though.”

“No…*huff*…prob.” At last she turned to face me. “and thank...*huff*... you Guilty.”

“It’s what I do. Besides, no thanks are necessary, it is my job afterall.”

“Okie dokie lokie.” She giggled. “Anyways… I need to get going.”

‘What? She only just got here!’ “Where are you off to so soon? You paid for two hours; it’s been… 40 minutes, tops.” I feigned a tiny bit of hurt.

“Oh, I’ve got… lots to do today. I have to write up invitations, and I need to bake three cakes by tomorrow, and I still need to buy… eight presents this week… lots of birthdays coming up. Also I need to go give Gummy a bath, and sweep upstairs, and I need to get most of this done by six tonight, because the Cakes are having dinner out, and I’m watching the kids.” She was ranting again… but not the same, cheery, hyper ranting as before. She was… annoyed… tired. She didn’t really want to do any of that. I decided, then, that I was going to try and convince her to get out of as much of that as possible.

“Well before that… Why don’t we get cleaned up, hmmm?”

“Oh…yeah… hehe… almost forgot.” She looked down at her coat, which was caked with a fair amount of cream and sauce… not to mention, she still had a chocolate crotch. I was even messier than she was, I was sticky all over. The sheets though, they were a horrid mess. Brown and white and red everywhere... I was a little worried the chocolate might not wash out. (Don’t worry it did in the end.)

“Why don’t you head, uh, past the foyer… up the stairs, and the first door on the right, is the bathroom. Hop in the shower…I’ll join you once I’m done down here.”

“Sounds good.” She smiled, scrambled off the bed and started bouncing her way out of the bedroom.

I quickly gathered up the sheets tossed them in the washing machine and ran it. I made my way upstairs after her… she was excitedly perusing my assorted soaps and shampoos when I arrived.

“Wowwie! I’ve never seen this many showery thingies except at Rarity’s!”

“Haha, yeah… well take your pick, they’re there for you after all.” I slipped into the shower, only to find the water freezing. I yelped in surprise. “HAH! Brrr… You, uh… you take cold showers?”

“Uh-huh! They’re super good for you!” She grabbed up a bottle of shower gel and started lather up her coat.

“Huh…I do that too… actually.” I helped myself to dollop of soap as well. “Soooo… was that everything you hoped it would be?”

“…Not everything…”

‘What!?’ “No? Is something wrong?”

She perked up. “What!? Oh nononono nothing’s wrong, it was amazing and awesome and super-fun, and delicious. It’s just…”

Now, instinct here told me that I’d done something wrong, and part of me wanted to question her until I’d figured out what I did. That is a habit you lose quickly as an escort. If a client wants you to do something, telling you is their job. Plus you can come off as pretty weird if you start to interrogate the client. So for the time being… I just stayed silent.

“I really wished I could’ve like… shared food with you… I mean, like kissing-eating. But since you said we couldn’t…”

“Ah… I see. Well I’m sorry to disappoint you Pinkie, but for that, you’re going to have to find yourself a boy or girl who shares your tastes… *hmph*… literally and figuratively.” I smiled at my own joke.

“Hehe… yeah”

The two of us shivered together, scrubbing ourselves.

“So do you, like, throw a party for everypony in town? Because that’s got to be a hassle.”

“No, not everypony… but I do bake everypony a cake and buy everypony a gift… I have to, I’m the party pony afterall.”

“Doesn’t that get… tiresome?”

“…sometimes….”

“Well, why don’t you take a break?”

“No time... *humph*... I’m not sure I know how to take a break, anyways.”

“Yeah?”

“Yeah it’s like… I don’t know how to not be doing something. I get wiggy if my schedule is empty.”

‘That’s like my problem backwards'
.’

“… I’m always cheery and smiley for everyone, because I love making my friends smile. But sometimes… I dunno.”

“Sometimes you just want to drop it all?”

“…sometimes…”

“So why don’t you?”

“I don’t want to let anypony down!” She was so serious about it.

“I understand… but it honestly sounds like you need a personal day.”

“I take days like that… sometimes I go swimming with Rainbow Dash, or go to the Spa with Rarity, or take care of animals with Fluttershy, or help Applej-” She stopped herself short.

“Hmmm?”

“Nothing… just… I do take personal days.”

I made no attempt to hide my doubt. “To be honest those don’t really sound like personal days.”

“How so?”

“Well I mean, those don’t really sound like days to yourself.” She just cocked her head at me. “I mean like… when’s the last time you spent a whole day relaxing?”

“Ugh… that sounds boring… even Rainbow Dash doesn’t do that… and she naps more than anypony I know. I’ve never done that.”

“Well when’s the last time you took just an afternoon to yourself… just sat down and read a book, drank a cup of tea, just… relaxed.”

“Not since… ever.”

“Well would you like to?”

“You mean right now?”

“Yeah…” I turned my spigot, and the shower died down to drips “… look Pinkie, you paid for two hours… why not take advantage of that? We can just… sit… relax… I’ll put on some music. You don’t have to worry about… anything."

“That sounds...” I’m not sure she really realized how much she actually wanted to just… relax… until I brought it up. “…really really really nice.” She looked so… relieved… is really the only word for it.

“Then, why don’t we dry off and head downstairs?”

“O-okay.” So, the two of us hopped out of the shower, rubbed ourselves dry, and trotted back to my foyer. I put on a batch of Chamomile, something to relax and soothe. Pinkie sat at my table, twiddling her hooves.

“So… how do we do this?”

“We already are… we can talk, or we can just sit… the tea will be ready soon, too.”

“What do we talk about?”

“Anything you like.”

“…I dunno... How are you doing lately, Guilty?” She offered, unsure. She was just looking for anything at all to ask. Luckily, small talk comes easily to me.

“I’ve been better, to be honest.” That’s a little trick I use when I need to get a conversation rolling… because any decent pony will want to ask what’s wrong… and then I’ve got a response to that. It works most of the time. This time was no exception.

“What’s the matter?”

“Well… I dunno… I just… I’m trying to find a hobby, actually… and… I’m just not having much luck.”

“Aaaaw, that’s no fun… have you tried water skiing? Or maybe skydiving?”

“Uuuh, I’m look for something a little more… indoorsy.”

“That’s no good,” she stated very matter-of-factly.

My face curled in confusion “Why’s that?”

“You work indoors… you need to get outdoors if you wanna have fun, duh. You should hike.” She said it like it was the most obvious thing in the world.

“Well… It’s worth a shot. Thanks Pinkie.” I was happy for any direction in my quest for fun, quite frankly.

“Yeah, it’s easy too… just grab a friend and start walking.”

“Can’t say I’ve got a friend to go with, Pinkie.” I chuckled, I was just trying to be funny.

Pinkie, however, was not pleased. “WHAT?!” She stood up immediately. “How can you have no friends? That’s just… I don’t even… I need a moment.” She cradled her head in her hooves.

“Uhhh... sorry. You okay Pinkie?”

“Yeah yeah, it’s just… you really have no friends?”

“Well…” ‘What’s the harm… it’s not telling her much…’ “I have a friend back in Manemattan… that’s about it.” ‘Does Derpy count?’ “Maybe… maybe I’ve got a friend in Ponyville.”

“Well… first of all… I’m your friend, Guilty.” She smiled at me comfortingly. ‘When did this become Guilty’s pity party?’ “and second… you need more friends.”

“And how am I supposed to make friends in town Pinkie, you’ve seen how some ponies treat me for just… going about my business. Everyone knows who I am… and with the exception of a few… they avoid me like the plague.”

“Well what about your clients?”

“They avoid me just as much, if not more so... that and… they’re just… clients… I can’t let myself get too attached.”

It was then that Pinkie asked me a question that I had never really asked myself. “Why not?”

I opened my mouth to answer… only to find I didn’t really have one. I’d been told a lot, back in the stable, that you never get personal with a client. I got told it only brings trouble, but I never really had a concrete reason why that was. After a bit of figuring, I had something that resembled an answer. “Because… I don’t want to give somepony the wrong idea I guess…”

“How do you mean?”

“Well like… if I start meeting a client regularly… how long before they start asking for freebies.”

“Okay, so maybe that does happen… but you can just say no… I don’t hand out free cake to my friends.” I opened my mouth to say something. “Birthdays don’t count.” She stuck her tongue out at me, and I promptly shut my gab.

“Okay, so maybe I say no… what if they don’t want anything to do with me after that.”

“That’s easy… if they do that, they were never your friend in the first place… you go find someone else.” ‘It can’t be that simple can it?’

My face couldn’t help but twist into a frown. “Okay… so all that aside… how am I supposed to ask someone… just in the middle of a session ask… ‘Hey do you wanna go hiking?’”

“I dunno… figure it out, silly.” She smiled… and the kettle started whistling.

“I’ll get that… wait right here.”

I quickly made for the kettle.

‘Ugh… what am I doing… desperately asking a client for advice on having fun? C’mon, you’re supposed to be helping her relax… get it together Guilty.’

After my little internal pep talk, I made my way back to Pinkie.

“Here you go… a nice hot cup of chamomile.” I put placed her mug in front of her, and took my seat once more.

“I dunno… how’s caffeine supposed to help me relax?” She sniffed her tea curiously.

“Actually chamomile isn’t really tea… no caffeine.” I grinned and took a nice big sip… it was good. Pinkie took a sip as well… she seemed satisfied enough. For a long while we just sat… and drank. Pinkie seemed pleased… not quite relaxed all the way, but… getting there. She was staring intently into her tea.

It was almost perfect… I realized I had forgotten the music once more, but something told me Pinkie wouldn’t be that wild about classical anyways… call it a hunch.

“I’m sorry… by the way.” Pinkie broke the silence.

I wasn’t quite sure what she was apologizing for, to be honest. “Uh… apology accepted, I guess… but… what do you have to apologize for?”

She looked up from her tea… her face filled with… worry... shame maybe? She felt bad about something, I just wasn’t sure what. “For… you know… the whole Applejack thing.”

‘How was that her fault?’ “How was that your fault?”

“I should’ve stopped her… she was… I’ve never seen her like that before.”

“Really? That’s the only way I see her. She always yells at me for… nothing, really.” I shrugged. “It’s no big deal. I’ve gotten used to her… I’m the one who should be sorry.”

“What? You didn’t do anything!” She was almost angry at my apology.

“I lost my cool. I contributed to that fight just as much as she did. And I verbally bitch-slapped her… pardon my language.” I’m still beating myself up for that comment about her parents. Some day... not anytime soon, mind you... I’m gonna have to apologize for that.

“Okay, yeah, you kinda really did,” she admitted.

“I am sorry about that… it can’t have looked very good for your bakery.”

“Okay, well… okay first of all it’s not mine I just work there.”

“Ah.”

“And second… Sugar Cube Corner’s fine… if anything it’s getting more business.”

“Well I’m glad something good came out of it, I guess.” I chuckled nervously… Honestly I wanted to shift the topic off of this as fast as I could. This wasn’t helping Pinkie relax either.

“So who does own that bakery?” ‘That’ll do for a topic.’

“The cakes… but anyways I had something I wanted to ask you.” I wasn’t sure who the cakes were, but it looked like that was all the answer I was getting.

“Shoot.”

“How did you… how did you do it?”

I cocked my head. “How did I do what?”

She took a long sip from her mug and set it down… she looked me dead in the eyes… she was... curious… maybe fascinated is a better term.

“How did you just… know… about Applejack I mean. Cause… I’m one of her bestest of best friends, and I had… no idea about her parents.”

“Oh that… well that’s just… I notice things… the way she says things… the way she looks when she says them. Not just her, though… anypony. Body Language, cadence, where eyes are looking, when ponies stutter, their very actions, every piece of information tells you a little bit about a pony. If you pay enough attention you can… read ponies like books.”

Pinkie just stared at me with that same curious fascination. “Is… is that your special talent?”

‘Damn…’

“What makes you say that, Pinkie?”

“Your cutie mark… I’ve been trying to figure out your special talent since I saw it. That, and the way you were talking just now… that’s how Rainbow Dash talks about flying… or Twilight talks about magic… or how I talk about parties, there’s no way it’s not your special talent after you got all… intense about it.”

‘She smarter than she seems…’

“Well, for your information Pinkie… yes… it is my special talent. Don’t tell anypony though… It’s a secret.”

“My lips are sealed!” She smiled briefly, only to have her expression sour. “Hey Guilty?”

“What’s up?”

“Can I… ask ooone more question? I promise we can go back to relaxing after that but… I’m just really curious about something.”

“Go ahead.”

She looked at her tea again… ever uncertain.

“Go on, Pinkie… it’s okay.”

Without lifting her head, she asked “What’s a stud?”

I was only slightly taken aback. “Oh.”

“Is it something bad? Cause I always hear guys call their friends that all the time. I thought it was a good thing but… the way AJ said it… and the way you reacted…” She trailed off.

“Well…” I swallowed. I’m not that much of a prude, but it’s still an unpleasant topic. “… it’s a very old word, first of all. The more, uh, ‘modern’ meaning is a guy who, you know, gets a lot of action.”

“Uh huh.”

“What a lot of ponies don’t know, though, is where the word comes from. Now… way back, way before the princess, it was legal for a pony to … you know… own another pony.”

“Y-yeah?”

“How should I put this… ok let’s say I owned a farm. Now let’s also say that I… well… owned a bunch of… well there’s no nice way to put it… slaves. Now let’s say one of those slaves was a fantastic worker. He could lift more, pull more, pick more than any other pony. But as time goes on, that pony gets old… and he can’t do as much."

“…okay…”

“Well as a… well a slave owner… any children of my slaves are also my slaves. So I get a bright idea. I’ll just have that pony… impregnate… all my mares. So they’ll give birth to strong kids… kids who can lift, pull, pick just as much as their father. And then I get an even brighter Idea. I’ll show all my other friends how much my slave can do. Then I charge my friends to let my stallion get their mares pregnant. Now that father has been what’s called… ‘put out to stud.’”

The look on Pinkie’s face… she was just… crushed. “…oh… oh my gosh…”

“… yeah… So what it really means is… ‘a pony who’s no good for anything but sex.’”

She continued to just look on in horror.

“And… well you can see why I’d be offended by that. I mean… I do get called stud every now and then; but that’s just ponies trying to compliment me. Most don’t know what the word really means. Applejack on the other hand…”

“Yeah… she knew exactly what she was saying. Oh my gosh… Guilty I’m so… SO sorry.”

“Don’t be, Pinkie. First of all you didn’t do anything wrong.” Cue the comforting smile. “Second, it takes a lot more than that to really get to me. I’ve got thick skin; you don’t get into this line of work without getting called some… pretty awful names.” I never let the smile leave my face… if Pinkie thought I was even a little upset she’d want to comfort me.

“I...okay, Guilty.”

“Can I ask you a question now?”

“Of course.”

“May I brush your mane?”

“Wait, what, why?”

“Because it’s still pretty wet, and It’ll help you relax.”

“If… If you want, I guess. It’s really hard to brush through, though.”

“I think I’ll manage. Wait right here.”

Honestly, I was just trying to keep her from jumping back into conversation, but I figured she’d like a good brush. I hopped upstairs and grabbed a brush and a comb, one with extra wide spaces.

So I got back, and I started brushing her mane. Fun fact: for extra tangled hair, start brushing at the bottom and work your way up… makes it a lot easier.

Pinkie seemed a little uncomfortable as I worked my way up. Once I got to the top, though, Pinkie was in heaven. “That feels… reeeeally gooooood.”

“I know, right?”

Eventually her damp tangles were groomed straight. “All done.”

I took a moment to appreciate my handiwork. “You look… lovely, Pinkie.”

“Yeah? Lemme see, lemme see!” She bolted upstairs without me. I heard the bathroom door open. When I made my way up, Pinkie was scrutinizing her new look. “I look all… gloomy.”

“You don’t like it?” I walked up alongside Pinkie.

She continued to stare at her reflection. “I’m not sure. I… I used to have my hair like this… when I was little.”

“Yeah?”

“Yeah… those weren’t… those weren’t really happy times.” She chuckled nervously.

“Rough childhood?”

“…kinda…”

“Me too.”

“Yeah?”

“Yeah.”

There was a long pause… we looked over each other’s reflections. I think each of us was kind of… sizing up the other. I dunno… maybe it’s just me… but I felt… something of a connection to Pinkie. Had her father beat her too? Did she have any scars? Did she know her mother? Had she gotten away from home as soon as possible, like me? Did she keep in touch with her family?

I’m not sure what was going through Pinkie’s head, but… but I kind of think. No, not think. Feel. I feel like she was thinking roughly the same thing I was. Either way she had the decency not to pry, as did I.

“… How do you think I look?”

“I think you look... sexy, quite frankly.” It was true… she looked really good with her hair down.

“Really?”

I took a second look, meeting her reflection’s gaze. “Yeah… really.”

“Huh… Do my tail too.”

I happily obliged. It was quick work, and soon Pinkie’s mane and tail were combed and brushed straight. “Do keep in mind, Pinkie, that as… voluminous as your hair is. It will have a little more body once it dries.”

“Okie dokie.” She examined herself in my mirror over and over again. “You know what? I like it.” She beamed again… a sort of… impossibly bright smile. “Anywho, let’s get downstairs, my not-tea is getting cold.”

After that, Pinkie… really mellowed out. For the remainder of her time, which was roughly an hour, we just sat… I poured her a few more mugs of chamomile… we talked a little bit about her friends. Apparently she’s really good friends with Twilight, Applejack, Derpy’s friend Rainbow Dash, and Rarity. We talked about the weather, too, about how cold it’s been getting.

We talked about smells funnily enough. I told her about the candles and oil and incense that I use; and She told me about how different sweets smell when they’re done right, and how they smell good together. It was nice.

Anyways, after two full hours, Pinkie gathered up the food she brought with her, and got ready to leave. “Well, I hope you enjoyed your session.”

“I did.” She was… really quite beautiful with her hair down. She’s a really cute mare, even if she is a little heavy. (Hey I spent the better part of a half hour under her, I notice things, okay?)

“Do you… think you’d like to have another session in the future.”

“Hmm…” She shook her head. “No… I think… I think I’m gonna try and find somepony to date again.”

“Well, good luck to you… but you know… If you ever wanna make a session… stop by… have a cup of tea… let your hair down, so to speak… we can always do that,” I offered.

“Hmm… maybe.” She turned to leave. “Oh, and stop by Sugar Cube Corner soon. Pumpkins are in season, so we’re gonna have these really good little pumpkin cupcakes… you should try it.”

“I’ll try… I am a busy boy after all.”

“Hehe, I getcha. Bye bye, Guilty.” And she left. She kept her hair down… I wonder what her friends will think.

I called after her. “And write ahead of time next time.” She laughed

All in all, today was… unexpected, though not unpleasant.

Tomorrow, I have an early session, but after that I think I’m going to try going for a hike… out by Ghastly Gorge maybe. I’ve lived here for two years, but I still haven’t really seen the sites. I’m not going to invite anyone… not quite yet. Maybe soon though… maybe I’ll ask Derpy… I mean I know she can fly, but… but maybe she’ll enjoy the walk, I dunno.

Either way… I should get to sleep.

I hope I like hiking. It’d be nice to… how did Close put it? Have something to ‘do between doing.’ I’ve never really… had a hobby before.

Might be fun.

Author's Note

Chapter 5 WEEEE!

I like how this chapter turned out. I hope you all enjoy.

P.S.

Food-play is hard to write.

Refusing Service

Chapter 6

Refusing Service

Dear Journal,

It has been quite a few days since I last wrote, and I would like to start by saying something that I didn’t think I would ever say.

Hiking is fucking awesome.

Okay, so, this all started when Pinkie put the idea in my head. I decided to pack myself a lunch and take a hike out to ghastly gorge. I’ve lived in Ponyville for a couple years now, but in all that time I’ve never really… gotten out. Never seen the sights, you know?

So hiking is good exercise and all, but mostly… nature is just gorgeous. I grew up in a concrete jungle; Manehattan was a metropolis. So in all my life I’ve never really... had a chance to appreciate nature... outside of a book, I mean.

So, as i said, my first hike was to Ghastly Gorge. The trek there was pretty on its own, just a little path through forest. Autumn is in full swing by now, so the oranges and reds and yellows… beautiful.

But the Gorge itself… it’s just so… I can’t describe it. It’s like… I’ve never been that high up without a fence or a window or something. It’s so… exhilarating being that high up. That must be what Pegasi feel like.

I walked all the way to the precipice and peeked over the edge. You can feel it… you can feel how high up you are. Your guts, just, twist in fear; it’s awesome.

But anyways, I spent… all day, just… walking along the Gorge. I didn’t get back until sunset. It… It was too cool… I wished I had packed dinner.

So next time I did.

A couple days later I had a free day, so I popped into town to grab myself a couple of heavy duty saddle bags. I was so excited I didn’t even notice the townsponies’ stares. I was grinning the whole time.

I set out just after breakfast. I got much farther the second time… all the way to where the quarray eels make their nests. You can see them stirring in their little caves in the canyon-side. Every now and then you can see a giant nose popping out for a quick moment, and sometimes if you look close you can catch one grabbing a low flying bird out of the air. I have never been so awe-struck. I’ve never seen any animal that…. massive before, at least not outside of a cage. They could easily swallow me whole.

One made eye contact with me. I could see it as the sun was just starting to dip, on my way back. Those… beautiful orange eyes. Its gaze followed me from deep in the creature’s nest. I just… stared back at it as I walked by. It was…. I don’t know, I can’t read animals like I can read ponies… hungry maybe? Maybe it was daring me to come over and dangle myself in front of its den.

Humbling… very humbling.

And fun… so very fun.

Relaxing too, is a weird sort of way… I dunno… it’s almost… meditative. I’ve got a hobby, it’s official.

So, I’ve decided I’m going to start hiking more. There are supposedly a lot of scenic locations around Ponyville. Some places are a few days away… or more… I’m going to need to learn about camping. White Tail Woods is close by, though. I may start taking walks there.

Just because.

I have to give credit to Pinkie… she really nailed it. I love hiking more than I thought I would. Hell, more than I thought I could.

I definitely… I’m definitely going to ask Derpy if she’d like to hike with me. It can only be more fun with two ponies, right?

Anyways, that’s enough about me and my newfound love.

I’m writing this entry much earlier… or later… than I’m used to writing Journal entries… It’s just about lunch time. The reason for this is that I didn’t get to sleep until the sun was up.

I’ll start at the beginning.

I received a letter a few days ago. It had been delivered by Derpy, which was unusual. Most of the letters I get are hand delivered; most ponies don’t want to suffer the indignity of being seen at the post office sending a letter to “that one cabin outside town”, but somepony had actually used the mail system to reach me. Once I got a better look at the letter I understood why… however it only raised more questions.

This letter was from Canterlot.

Now, I’ve never gotten a letter from Canterlot before, mostly because I’ve never been to Canterlot. I don’t know anypony in Canterlot… but apparently someone knew me. I wasn’t quite sure what to expect when I opened the letter.

It read:

Yo, G P

My friend said I just HAD to have a session with you… says it does wonders. I’ll be in Ponyville on the 16th. I’ll drop by at midnight.

P-3

‘P-3?... Midnight?’

Now, bizarre initials aside, I’m very used to having late clients. When you work in a stable, it usually opens at dusk and closes at dawn. I used to very much be a night owl. It was just… it had been a while, several years even, since I pulled an all-nighter, and I figured if a pony was showing up at midnight, they weren’t planning to leave till daybreak.

I made a point of sleeping in this morning… no… yesterday morning… I barely slept last night, it still feels like yesterday.

Boy, am I glad I don’t have a client today…

Wait, Do I?

No I don’t… I checked.

I’ve been all paranoid about that since that time with Rarity, Derpy and Carrot Top.

Anyways…

Like I said, I made a point of sleeping in… I tried to sleep until about five o'clock, but I got restless at about two. Caffeine was going to be my hero… caffeine and sugar. I had a breakfast-lunch of cereal and toast. Not a brunch, mind you; brunch implies melon, and there was none to be had.

I spent most of the day reading some of the articles in a new magazine I bought, Equestria Outside. (Yes, it’s a hiking magazine.) As the sun sank far past the horizon, and night took hold, I already found myself drowsy, and it was barely eleven. I brewed myself a quick pot of chai tea to keep me awake.

Midnight came and went before there was any sign of my client. I was a little upset.

‘If she doesn’t show up after all the work I put into my appearance, and the lighting, and the music and… staying up this LATE… I might just lose my freaking mind.’

Okay maybe more than a little upset.

At around 12:30 there was a knock at the door. She was late, but not inexcusably late. Either way, there’s no point in greeting a new client with anything but total hospitality. I swallowed by childish pettiness and answered the door.

“I was worried you weren’t going to make it,” I said as I opened my front door.

I was promptly pushed to the side as a white blur barreled past me, almost knocking me on my flank. “Lemme in, dude! It’s freezing!” Once I recovered I had the mental presence to shut the door. The white, somewhat rude unicorn that had just barreled past me was shaking from the cold. Her mane and tail were positively electric... like blue lightning. Spiky too. Her Cutie mark was a musical note. Her eyes were invisible behind reflective purple shades.

‘Sunglasses at night? Now that’s class.’ I stopped myself from rolling my eyes.

Once she stopped shivering, she took a quick survey of my humble home. “Nice digs, buddy. Not bad at all.” There was a sort of… beat… about her, her head endlessly bobbing to some silent song. Even the way she trotted was almost rhythmic.. each step the quake of a drum.

“Uh, thank you, I try. Would you like some tea, I’ve got a kettle on the stove right now, and quite a selec-”

“Naaaah, dude, that’s cool I got about 6 energy drinks runnin’ through me. Got any beer?”

‘Ugh.’ I did have beer, but I did not like where this was going. This girl’s whole attitude… I could tell she was a party girl… and I could tell she would not be stopping with beer. I have some harder liquor but... I really wasn’t looking to lose bits on a client by having to replace expensive booze. Especially if the odds were that she wouldn’t be a repeat.

I fetched a six pack, and we took our seats. The beer was warm; it hadn’t been in the fridge. I didn’t mind all that much, and neither did she, by the looks of things. She finished the first can immediately and immediately started on her second, her magic ripping it free from its little plastic crown. I was content just nursing mine. “Are you sure you wouldn’t like something warmer?”

She just shook her head… never stopped drinking. After three beers, and a loud belch, she finally felt like conversation. “Not bad. Domestic?”

I had no idea to be honest. “I don’t know, actually.” I shrugged. “I, uh, I have a few questions I’d like to ask you, if that’s okay.”

“Shoot.”

“If I may properly introduce myself *ahem*… My name is Guilty Pleasure. What may I call you?”

“Vinyl’s fine, dude.”

‘Vinyl? What happened to P-3?... Oh well.’

“Very well. Second, how did you hear about me?”

“Oh, that. I got a friend in town, Pinks. She said I should stop by because…” She swallowed. “…you were a blast.”

She was lying. I don’t doubt that her friend recommended she stop by, but not for the reason she said. I assumed ‘Pinks’ was Pinkie. A ‘blast’ is just not something I was for Pinkie. I was the opposite of a blast… I was a wet blanket.

“So I had a gig in town and figured… ‘What the hell? I can stay here for another day.’”

“A gig?” I cocked an eyebrow.

“Yeah, I’m a D.J…. Wait, you mean you didn’t recognize me? I’m hurt.” She smirked at me.

After that I did recognize her… I’d seen her picture in a few magazines… She was D.J. Pon-3. Now I’m not really one for… whatever that genre of music is called. But I know enough to know she’s something of a celebrity. She performed at a royal reception, I believe.

“Sorry... I only just put it together.” My hoof found the back of my head. I actually blushed a little.

She chuckled. “S’all good, bro. I’m just pulling your leg.”

I smiled. “So you had a show in Ponyville tonight?”

“Last night.” Her brow furrowed. “ It was… kind of a big deal. I was on stage in the town square and everything… some… festival or something. I dunno. You didn’t go?”

“I don’t go into town that often. I’m not really… Ponyville, if you catch my meaning.”

“I hear ya, dude, me too. It’s all too…”

“Rural?” I offered.

“HA! Exactly. City boy?”

“Mmhmm.” I smiled; it was nice to find a little common ground.

“Where from?”

“Manehattan.” I allowed myself to start throwing back the beer. She may have come off as… brash, but she was friendly enough.

“MMMM” She hummed, her voice vibrating off the aluminum on her lips. She put her empty on the table, finishing what I believe was her fourth can. She opened her fifth fairly quickly. I can’t drink beer like that… I get too full. I don’t know where she was putting it all. “I… love…Manehattan.”

“Yeah?”

I… love Manehattan too... I really do.. I won’t lie; I miss it. The bright lights. The iridescent sky. The 24-hour fast food and liquor stores and salons, even. The… anonymity of walking through the streets. The buildings. The sight of carriages filling the streets. The din of honking horns. The sirens. The rooftops. The alleys. The smell of the river. The farmer’s market. Little Bitaly. The pizza. The bagels. Even the bums. I miss it all.

“Yeah, dude. I mean… like… you can find anything there. Like there’s this little place WAY down on 82nd. It’s this little haysian-food place. They make these dumplings. They’re like filed with this weird…egg…frosting… stuff. They’re awesome. AND I got this sound system one time, for like… half of what it should have cost.”

I chuckled. “Lemme guess… some guy sold it to you off the back of his cart?”

“Yeah… why?” She raised an eyebrow.

“You do know it was probably stolen, right?”

She just shrugged. “Oh well… mine now.”

“HA!” ‘Classy.’ I finished off my beer… leaving me now one drink to her five. “So tell me about Canterlot; I’ve never been.”

“Canterlot’s cool. Nice shops… beautiful city. And shit, the view from the mountaintop: fucking sick. The ponies though… ugh.”

“Bad?”

“No, they’re… okay. It’s just… *sigh*… everypony’s so stuck UP. Ya know?”

“Yeah, I get you… It’s the… ‘Bed of Nobility’ and all.”

“Exactly. Everything is all… status… and… image. It’s a snore fest sometimes. S’got a sick underground though. Some ponies who actually know how to enjoy life.”

“That’s good.” I wasn’t a hundred percent sure what she was talking about, but I assumed it had something to do with loud bassy music in abandoned warehouses or something equally ridiculous. “Well, I’ve just got one more question.” Hunky smile, activate. “What can I do for you?”

A mischievous grin spread across her face. “Oh, you know… I’m just… looking for a good time.” She stood herself up… and began strutting around the table towards me. “Just trying to… enjoy life.” Her voice was suddenly sultry. “Wanna have a little… fun… Guilty?”

If I may be totally honest… she wasn’t very good at the sexy voice. She sounded a little… silly. But hey… I’m a professional; I was just being overly critical.

I could already see my next move, though. She wanted to seduce me. And If she wanted to seduce me… I was going to be seduced. I did my best to appear a bit flustered. If I could blush on cue, I would, but I don’t think anypony can pull that off. But even so, I can stutter a little, shift uncomfortably, swallow visibly.

“I would… uh, I would like that very much.”

“I bet.” Her grin grew even wider. She was standing behind me now. “But first thing’s first… I’m gonna need something a little…” Her mouth can down to my ear… just hovering. “…stronger.” she whispered.

“I’ve, uh… got a liquor cabinet… it’s, uh, pretty…” Visible swallow. “…expensive.” I’d like to stress how easy this is to overdo… play the part too hard and you just look like your acting… the trick here is to undersell it.

It’s like this. Someone who is being seduced doesn’t want to look it… they want to act casual, like nothing’s really getting to them. So if I want to appear like I’m being seduced, I want to appear like I want to appear casual. I have to be… subtle.

She chuckled, her breath gently tickling my ear. “Trust me Guilty, I can afford it.” Her muzzle grazed me ever so slightly. “Now why don’t you go pour me something, hmm?”

“O-okay.” I made my way over to my liquor cabinet. I keep it decently well stocked. Not nearly as much of what I’d like is available in Ponyville. Still, I’ve got enough to whip up a few cocktails. I’ve got a sort of a little counter between my kitchen and foyer; I think it makes for a good bar. Vinyl seemed to think so too, since she stood opposite me. “What’ll ya have?”

“Mmmmmmm… something sexy.” She licked her lips. Again, my inner escort was getting fed up at how much she was overdoing it… she didn’t appear… genuine. But still… that’s just… me being too hard on somepony who isn’t a professional. Regardless, I did some quick booze math in my head.

“That… can be arranged.” At first I was afraid I didn’t have enough cranberry juice, but I did. Now, I’ve had a little practice, and a little training, in the fine art of mixology. (That’s a technical term, by the way. I swear.) So when a client asks for ‘something sexy’ the first thing I think of is a Sex on the Beach. It’s a strong drink, but when it’s done right it doesn’t really taste like it. I popped a couple ice cubes into a highball, and poured in my liquors and juices. It came out looking… perfect. The orange juice settled at the bottom, the cranberry juice on top… just like a Sunset.

I placed the glass delicately in front of Vinyl. She actually slid her shades down her nose to get a better look. Her eyes… they were beautiful. Royal Purple. Almost the same color as her ridiculous shades. “Wow… you really went all out.” ‘Not really.’ “What’s this called?”

“It’s a, um… Sex on the Beach.” Nervous shifting of eyes.

She took a sip. “Whoa, dude, I said something stronger. Does this even have anything in it?” Her act was completely forgotten… she was distracted by her drink.

“It’s almost half liquor. Is it good?”

She took another sip… then a longer one… then a gulp… then the drink was gone. “Dude…dude… You’re awesome.”

I wasn’t sure if I should go back to my act of being seduced, or if I should just accept the praise. I decided on the latter. “Thank you.” I smiled.

“Make something else!” She was so excited… it was kind of cute, to be honest. She was practically bouncing on her hooves.

I decided to make her a Painkiller… I didn’t have any coconut syrup; I don’t think anywhere in Ponyville would even have it. But I did have a little bit of coconut rum, so I made do. I pulled a tumbler out of a cupboard and began mixing my drink. “Whoa, dude, I don’t need a fresh glass, this one’s fine.”

“What I’m making doesn’t go in a highball.”

She cocked her head to the side. “What’s a highball?”

I began measuring out my dark rum. “That glass you just drank from… that’s a highball glass.”

“Yeah?… What’s that one?”

Next was pineapple juice. “This is a tumbler.”

“Why’s it called that?”

Orange juice. “I have no idea.”

She laughed. “You’re funny, dude.”

Coconut rum. “Thank you.” Pour over ice… serve. “Here you go.” Now, you’re supposed to sprinkle nutmeg on top… but she didn’t need to know that.

She took a long sip. “Mmmmm… that’s fucking radical. What’s it called?”

“That’s a Painkiller.”

“…huh…” She went back to guzzling down her drink. There was something on her face for a moment. When I told her what it was called. It was… hard to put my hoof on. Almost like a snicker, like she was in on some joke that I wasn’t.

“Something wrong?”

“Huh? Nah, dude, I’m good.” She was lying again. “So, uh… where’d you learn to make drinks like this?”

“Just… something you pick up in my line of work.”

“That’s cool.” Her magic lifted her glass once more, but not to her lips. She was inspecting it… carefully analyzing the glass’s surface. “So, like… each drink only goes into a specific glass?”

“Mmhmm.” I decided to make myself something as well. I started pouring myself Manehattan. It’s a damn shame I didn’t have any cherries. It’s just not the same without a cherry.

“Why?”

“Well, some drinks are too big for a small glass, or vice versa.” I took a sip; it was still a perfectly good Manehattan. “Like your drink for example. It’s meant to be drunk like soda almost. Big gulps. It goes down smooth. Now this is a Manehattan… it’s meant to be sipped. Cocktail glasses are for sipping. I thought you might know a little about booze, you don't exactly seem like a stranger to liquor.

She shrugged. “I’ve always been more of a ‘straight from the bottle’ girl.”

“Then why’d you ask me to pour you something?”

She shrugged again. “Meh, I was just trying to be sexy.”

‘I love it when they softball them in for me.’

Okay now, it isn’t uncommon that a mare feels she needs to… romance me. Some like the act, like Rarity, but others kind of tend to treat me like a date just out of habit. I always try to remind a client that they don’t have to do anything for my benefit. Sometimes, I have the chance to remind them in a cheesy way.

Vinyl had just happened to set me up for one of my favorite cheesy lines.

“Vinyl, You don’t have to try to be sexy… you are sexy...” There was suddenly a little bit of red in her cheeks… and it wasn’t from the booze. Corny though it may be, that line works almost every time. “…aaaaand you don’t have to go out of your way for me. Tonight is all about you.”

“F-fine…” She pulled her shades back over her eyes. She was a little flustered… right where I liked her. She spent a couple minutes finish off her drink in silence. I ended up finishing my Manehattan, so I poured myself another. I was beginning to feel the alcohol, which is usually something I like to avoid if I can, but… I got the feeling it was appropriate tonight.

Vinyl was getting a little bit tipsy as well. After all, she’d had probably a dozen drinks worth of liquor at this point. Not drowsy though… just tipsy… and more than a little silly. “You know what we should do, dude?”

“Enlighten me.”

“We should start a club together! It would be awesome!” She was enthusiastic, at least.

I kind… snort-laughed. “How would we start a club?”

“Well, like… you be the bartender.”

“Uh huh...” I was cracking up inside… I may have been a little more intoxicated than I realized.

“And, like… I’ll be the music.”

“Okay…”

“And we’ll pay ponies to do everything else.”

I laughed out loud. “How are we gonna afford that.”

“With the money we make from the club, DUH!” She rolled her eyes at me.

“Of course… and how, pray tell, do you propose we pay for a building, or liquor to start off... or for that matter the first round of paychecks?” I took a sip of my Manehattan as I rolled my eyes right back.

“Dude, I’ve got mad bits. I don’t know what to do with it all. I’ve got a seven-figure bank account!”

I nearly choked on perfectly good cocktail. “Holy shit, Vinyl!”

“Dude, you may not have recognized me, but I am a celebrity.”

“Hey! I recognized you… eventually.”

“Only after I pointed it out.”

I held up a hoof in defeat. “Fine, fine. You win.” I finished what was left of my drink. “So, were my drinks sexy enough for you?”

“Sexiest I’ve had.” She giggled.

“Well next time you may consider actually asking the bartender to mix you something, instead of just asking him to pass you the bottle. There are much better bartenders than myself out there.”

“I wouldn’t even know how to order anything, dude.”

“Well you already know three cocktails.” I decided to test something really quick. “You, know, the ‘Sex on the Beach,’ the ‘Manehattan,’ and the ‘Painkiller.” Her expression got like it did before. It was only for a split second, but when I said Painkiller her face got… it’s hard to describe… somewhere between acceptance and depression. Something about the name ‘Painkiller’ bothered her. I made a mental note of it.

“So Vinyl… are you having fun?” I walked back around my little makeshift bar.

“You bet!”

This time I was standing behind her. I whispered into her ear, “Wanna have a little more?”

Her ears perked up. “Mmmmm… which way’s the bedroom?”

“Right this way, Vinyl.” I led her across my foyer.

She was seemed more than ready… a big grin plastered on her face… plastered being the operative word. I joke, she seemed a little more sober than me, to be honest. ‘She sure can hold her liquor.’

“I’ll be honest, it’s been a while since I’ve had a stallion.”

“Bit of a dry spell?”

She snickered. “I didn’t say that.” I immediately caught her meaning.

‘She goes both ways… neat.’ I giggled.

I opened the door, my bedroom still looked, and smelled, enchanting. Candlelight and incense and music. It was quite the set-up.

“You’ve got a cloud bed, nice. I’ve got one too.”

“Hmm… can’t say I hear that a lot.” I quickly fished a birth control potion out of my trunk, and downed it. Normally a client asks what I’m doing at this point but.... she seemed oddly occupied.

“Something the matter?”

Her ears were flared out. She was listening to the music. When she spoke her voice was sort of… off. “I know who this is.” It wasn’t like she’d made a pleasant little discovery or anything. She seemed… upset that she knew who it was.

I listened for a moment. It was just some light strings, but it was a song I knew. “It’s, uh, Half Measure. Just some of her early stuff… I can change it if you like.” I was a little thrown, to be honest. She was full of life and energy seconds ago. Either way, I did my best to remain calm and collected.

“No, I… never mind, it’s not important.”

I raised an eyebrow. “If you say so. Before we begin, though… two rules.”

“Shoot.”

“No kissing on the lips.” I drew a little ‘X’ in the air over my mouth. “And if either one of us says stop… we both stop.”

“No prob dude.”

I smiled. “Good.”

She hopped up onto the bed and plopped onto her back. She looked tired, to be honest. ‘Maybe those energy drinks are wearing off.’ I quickly wriggled out of my jeans and slid myself next to her. Her body was warm from the liquor. Mine was too.

I started slow, peppering her withers with tiny kisses. She smiled again. “Mmmm That feels good.” Her body pressed against my chest. We’d only just begun, but she seemed to be quivering in pleasure. She let loose tiny little gasps. Little *ahs* and *mmms* as I pecked. My hooves traced gently along her flank as I spooned her.

I teased her until I felt myself grow hard, prodding it gently against her rear end. “Wow… it’s… it’s really been a while *hehe.*” She lifted one leg high into the air.

“Ready?” I asked… she seemed eager to get right to it.

“Yeah...” She was panting in anticipation. I brought myself between her spread hocks.

What happened next was… very awkward. Let me see if I can put this delicately. Have you ever tried to go down a waterslide that didn’t have any water on it?

Yeah… that.

“Uh…*hmm*…uh… hold on… *unf*… if you could just… yeah… okay no, wait… *rrgh*… Ok lemme just… *nnf* sunnova.” I tried and failed to… penetrate... several times.

“You, uh, want me to move, dude.”

“Yeah, actually, why don’t you-“

“On all fours?”

“Yeah.”

She rolled out of our admittedly awkward position, and crept up onto her hooves. I did the same, and…well... for lack of a more eloquent term… mounted her.

“Ok now if I can just… *huff*… oh come on… you want me to lick you first.”

She was not pleased to say the least. “Come on, dude, just fuck me already.”

“Well… *sigh*… I’m trying, I just… I’m not exactly ‘cleared for landing’ if you know what I mean.”

“What are you trying to say?” She was getting pretty upset.

“Dry as a bone, Vinyl,” I said flatly.

“What are you...?” She reached a hoof down. “Oh, come on!” I just stayed propped awkwardly on top of her as she spent a few moments rubbing herself. “Lemme just… do you… have any… lube... or something?” I trotted off the bed and over to my oils chest. I grabbed a simple oil, unscented, unflavored, nice and slippery.

Her magic pulled the bottle out of my hand before I could even hoof it to her. She immediately coated her hoof which proceeded to coat her loins. “Ok, try now.” I obliged, but… no go. It was plenty moist now, but… far too tight.

“Try and relax.” I offered.

“I am relaxed,” she fumed.

I let out a long sigh. “Spread a little wider.”

She begrudgingly spread her legs out. She groaned loudly. She was… just fed up with this. She was getting a little mad.

“I just… *nnf*… sorry Vinyl, it’s just… it won’t fit.”

“Yeah like that has trouble fitting into anything,” she scoffed

“Excuse me?” I honestly wasn’t sure I’d just heard that. Sure, maybe I haven’t got the biggest dick, but… you just don’t go there.

“Come ON, dude. It’s not that hard. Just stick it in me!”

I took a step back to examine the situation. I had a mare….yelling at me to fuck her. Now this is a situation I’ve been in many times before. Starting off as a prostitute, you’re never very good right away. Every whore has their share of unsatisfied customers. But I mean… stage fright… not being able to get it up… all that stuff… it goes away. Here, I was doing everything right, and a Mare was yelling at me to fuck her, when she was closed up like a vault.

And then I remembered something. I work for myself. I’m not just another whore in the stable. There’s no threat of punishment. There’s no one telling me to ‘suck it up, it’s the job.’ I can’t get fired if I’m my own boss. I’m self-employed now, which gave me a power I had yet to exercise. Honestly, I hadn’t had the need.

I had the power to say no. I’d honestly forgotten that.

“No…” I made a point of sounding as offended as possible.

“Wha?” Her ears perked up.

“No I’m not going to ‘stick it in you.’” I dismounted her and hurried off the bed. “I’m not going to fuck you. I’m not going to do a single thing more for you.” I began to put my jeans on as quickly as I could… which was not very quickly at all. “I’d like you to leave.”

The look on her face was just priceless. Her jaw was literally hanging open. Her shades almost dropped off of her face. “I… I don’t… but you’re… I… I want my money back!”

I was struggling with my left leg as I answered. “You haven’t…*nnf*… actually paid me yet, you know. And for that matter, you’re not owed sex.”

She was baffled. “But… but you can’t do that, you’re a whor-”

“Escort!” I cut her off. “I am an *ngh* Independent escort. You are paying for my time, not my body. Yes, I do have sex with a number of my clients but not simply because they want to. I enjoy pleasing mares… every time I pleasure a mare, every time… it’s my choice. And I’m *nnf* …fuckin’ zipper… I’m choosing not to fuck you.” It was honestly very… cleansing… to remind myself of this. Remind myself that I’m not here just to please mares, and make them feel loved for a few hours. That I don’t have anypony to answer to. That if I choose not a fuck a mare it doesn’t get docked from my pay. That nopony is going to tell me I messed up. That…

That the job isn’t everything… not anymore.

“I’ll… I’ll tell everypony you’re terrible! Nopony will hire you!” There was a slight flutter in her voice… I noticed it too late.

“Two things. I already have a healthy clientele, full of clients who know, respect, and trust me. Even still, I’m situated here in Ponyville, not Canterlot. You may have a few friends here, but I’ve got dozens of clients. Secondly… You… a celebrity… Are going to come out and say ‘I went to this whore, he’s awful?’ Yeah… I don’t think so.” I was being snarky… again. I was so focused on winning the little argument that I didn’t notice something important.

“What… what the fuck is wrong with you? Why the fuck won’t you just fuck me?” There were tears forming in her eyes… I missed those too. Honestly, maybe I didn’t… I dunno. If I did see them I chose to ignore them.

“Because, you’ve got a bad attitude. I was doing my best and you start… insulting my equipment. That’s… that’s just not right. I don’t have to put up with that.” To my credit I wasn’t vicious or anything… I kept a very collected tone.

“Then…*sniff*…then…*sob*… then I’ll leave. I’ll l-leave and I’ll *sob* n-never come back… I’ll just… g-g-go!” I snapped out of my little… tizzy, I suppose is the word. There were tears just pouring down her face. I was ready to try and calm her down once I realized how upset she was. It sort of came out of nowhere… well maybe not the tears, but the attitude. Up until right then she was… mad, livid even. But she just sort of… broke down.

‘Guilty, you fucked up again didn’t you?’

She collapsed onto the bed. She curled herself into a ball and just started bawling.

‘Yup… you fucked up, Guilty.’

Honestly, I only fucked up a little. I may have been a little harsh, but not out of line. I had every right to refuse service to a mare who was being disrespectful. I didn’t actually do anything to make her cry. At least, I don’t think I did. More than anything I messed up by not catching her in time for her breakdown. Then again I may not have been able to do much if I had. Sometimes… you’ve just got to cry.

I know that all too well.

After a bit, I hazarded putting a comforting hoof on her shoulder, but she shook me off. I decided the best thing I could do was give her a little bit of space. I let her know I was going to make some tea, and stepped out of the bedroom.

I’ve had mares break down crying before. If they don’t want comfort, I usually find that a little time to cool off is the best thing for them. So I put another kettle and waited in the foyer. She would come out when she was ready.

After twenty minutes, she did. She slunk out of the bedroom. Mane a mess, eyes red and puffy, glasses forgotten, head hanging. She was a wreck. She sat down opposite me… not a word. Didn’t touch her tea.

“…sorry…” She muttered. She was so… forlorn.

“It’s okay.” I tried not to sounds too somber. I don’t think I did a very good job.

“N-no… I mean it… I’m sorry I was…” She rubbed her eyes. “...makin’ fun of yer dick.”

“Oh… that… well, uh… apology accepted.”

“And… and sorry I-”

“Don’t be... nothing wrong with crying. This is a safe place Vinyl.”

“O-okay.” She started to tear up again. She brought her elbows to the table and buried her face in her hooves. I was going to move to comfort her, but a muffled question came through her limbs.

“Hey Guilty?”

“Hmm?”

“Can…can you make me another Painkiller, dude?” She was on the verge of crying again. She sounded like a little kid, like she was asking for ice cream because she scraped her knee. She was… and I mean no offense here… pathetic. Truly and utterly pathetic.

“Of course.”

Normally I wouldn’t want to give that much liquor to a mare… but honestly couldn’t fucking say no to her right now. Besides, I was sure she could handle another drink. So, I mixed her up a fruity batch of feel-good juice.

“Thanks.” She started nursing her tropical sedative.

“No prob.”

A few silent moments passed. She just sat there… lost in her glass. I decided to take a risk.

“You want to talk about it?”

She looked up from the bottom of her glass. “Talk about what?”

“Talk about what’s go you hurting so bad you need two full glasses of painkiller.”

“… I dunno…” She swallowed hard. “…I kinda… just had a pretty nasty breakup… is all.”

“… a mare?” I asked. It had to be.

“…yeah…” She admitted.

I got up. I decided I didn’t want her to drink alone, so I grabbed my whiskey, my vermouth, my bitters, and a cocktail glass out of my kitchen and joined her once more.

“So what happened?” I asked as I poured myself yet another Manhattan.

“Well, like… *sob*… ok…” She took a deep breath. “… we’d been seeing each other for a long time…”

“How long is a long time?” Everypony has a different idea of a 'long time' in a relationship.

“I dunno like two months.”

‘That’s… that’s not very long at all.’ I took a swig of my cocktail, and further regretted my lack of cherries.

“Okay, go on.” I said. I didn’t even really realize I started playing 'Psychiatrist Guilty,' but sure enough, I had.

“Well like… okay… things were going pretty well. We were having lots of fun… lots of sex.” She smiled almost lecherously. “She’s a wild one… whether she admits it or not. But after a while it just sort of… fell apart.”

“How so?”

“We… I dunno. We were fighting... a lot. There was a while where we didn’t get to see each other, just… very different schedules, ya know?” I nodded. “I dunno… after a while it just sort of… *sigh*... we didn’t… it wasn’t the same.”

“How so?” The key to helping somepony through their problems is actually very simple. Say as little as possible unless asked. Listen listen listen, and get them to figure it out on their own, If you can. And if you do say something... wait until you’re fairly certain what the problem is.

“It was… I dunno… like… when I’m dating somepony… it’s like… exciting. Like there’s so much energy and fun and… it’s awesome.”

“And this mare wasn’t like that?”

“No she totally was… I mean… different, but still. There was so much… life… in her.”

“Different how?”

“Well like… well for one she’s probably the first pony I dated who couldn’t stand my music.”

“Yeah?”

“She’s a big classical girl... heh... you’d like her, I bet.” Her face. It was amazing. Even through all the tears and puffy eyes and sobbing her face was… radiant. She was so, so happy just talking about this mare. “She’s a Cellist actually.”

I realized something… when vinyl said ‘I know who this is,’ she wasn’t talking about the composer… she was talking about the performer. “Was she the one playing on my Half Measure album?”

“…yeah…”

“*Hmph*… it’s actually pretty impressive you could pick her out like that.”

She giggled. “She was so proud of that album… she listened to it all the time… said it was her best performance ever…”

“You really liked this girl, huh?”

“Yeah, I did… I do.”

“So what happened?”

“Well it was just… it wasn’t right.” She looked down into her glass.

“You keep saying that, what do you mean?”

“I mean… It started out fine. Fun. Sex. Music. But after a while we just sort of… fell into a routine. It wasn’t… *sigh*… it wasn’t exciting anymore. You know?”

“I get you… Lemme ask you a question, Vinyl.”

“Shoot.”

“What’s the longest relationship you’ve ever had?”

“Uh… that one, I guess. I mean mostly they only last a couple weeks at the most. You know?”

“Mmhmm. So why did you stay with this mare for so long?”

“I dunno… I was never very serious about relationships… Mostly I’d just pick up a pony, fuck them silly for a while, and… I dunno… get bored I guess... Jeez, I sound awful, don’t I?” She found comfort in her cocktail once more.

I gave a slight shake of my head, and started making another Manehattan. There were no doubts in my mind I was going to regret this tomorrow… but hey a hangover builds character.

“Anyways… with her… I dunno, she sort of… walked into my life. She didn’t know who I was at first… so she just sat down and started talking to me. I was in this... terrible little bar... just hanging out.” She was grinning like a fool. “We ended up arguing for hours about music... we were really going at it.

“We fought and yelled and swore and it actually came to blows. But somehow... I ended up sleeping with her that night. I was blackout drunk, I’m *hehe* I'm still not sure how it happened, to be honest. We got along better after that... for a while...

“We had… we had a lot of fun, the two of us.” She swallowed hard. “I didn’t… I didn’t want to just… leave… I wanted to stay.”

“So she ended it?”

“…no… I did…”

“Why?”

“Because… because… I don’t know. It wasn’t the same… I mean it lasted for a while, that… that high of being with somepony… but… but it wore off. There was… there was nothing left for me.”

“Can I ask another question?

“Yeah, dude… go for it.”

“Do you get this broken up over everypony you date?”

She shook her head.

“So why her?”

She was quiet for a time. When she finally did speak she was… so timid…so fragile; her voice was shaking. “…I… I don’t… know. I don’t know why… why I keep noticing that she isn’t there… why I keep expecting to wake up next to her… why I keep going to bars hoping she walks in… why I…*sniff*… why I… why I miss her…*sob* … so so much.” She was weeping like a kid again. “I miss her, Guilty…*sniff*… I really really miss her!” She hid her face behind her hooves once more.

“So… you ended it… even though you didn’t want to.” It wasn’t a question.

Her face nodded from beyond its veil of limbs.

“…why?...”

“I don’t know, okay?! It was going to end anyways, so I may as well have gotten it over with right?!” Such… desperation.

“So you were sure it was going to end, huh?…Vinyl, I have a theory, would you like to hear it?”

“*sniff*… go ahead, dude.”

I cleared my throat. “I think, Vinyl, that you’ve never really gotten the real experience of a relationship. Yes, at first relationships are very exciting, but that’s just… a honeymoon. It’s the very beginning; you’re still having fun learning about each other, exploring each other... in every sense of the word. It’s an adventure.

“But… eventually you’ve done all the exploring there is to do. Eventually there’s no more excitement… no more… high, as you put it. But… that doesn’t mean a relationship is dying. It’s just… changing. You may have felt like the relationship was ending, but… I’m not so sure it was.”

Admittedly, I got most of that little speech from a self-help book.

“*sniff*… Don’t tell me that. Don’t tell me th-that I… that I walked away for nothing." She was about to break out into tears again.

“I don’t think you walked away for nothing, Vinyl. I think you walked away because you were scared. Scared of being hurt. It’s easier to break up, than to be broken up with, right?” She nodded. “You were protecting yourself… it’s just natural.” That I came up with on the spot. I just didn’t want her to break down again.

“*sniff*… you know a lot about relationships, huh?”

I don’t know why I did what I did next. I sort of… opened up. I don’t know why I’ve been so… so forthcoming lately. I keep… I keep talking about things… thinking about things, things that haven’t been on my mind in… years. Tonight though, I was especially vocal.

It must have been the liquor.

“…not as much as I’d like.”

“*sniff* No?”

“No. When I was starting off... doing this, I mean... I… I worked in a stable.”

“Manehattan, right?” I nodded. “That big one on sixth?”

I shook my head. “It’s a smaller place on twelfth.”

She smiled... just a bit. “Heh, I’ll have to stop by sometime. If they’ve got guys like you, that is.”

“Yeah, it’s a good place… they treat everypony right. Clients and escorts. But, anyways… when you work there… personal relationships with clients are absolutely against the rules. I saw more than a few ponies lose their jobs for meeting up with clients outside the stable. But… I worked there from the time I was… hell, thirteen, until I was a man. Never… never had the chance to really meet anypony.”

Vinyl looked appalled. “You were a thirteen year old Prostitute?”

“What? Oh... no no no. I wasn’t… I wasn’t an escort there till I was eighteen. They do everything above board, there. No I was like… an errand boy. Restocking liquor cabinets. Picking up shipments of… condoms… birth control potions… new oils, whatever. Fetching whatever needed fetching. Fixing whatever needed fixing. Just a go-fer.”

“Oh… so you never… you never had a girlfriend?”

I swallowed hard. “…I came… I came close… once… she… she didn’t feel the same way. That’s uh… that’s just the way it goes, though. You know?” This time mine was the voice that was wavering. I wasn’t anywhere close to tears but… but it still hurt to think about.

I honestly hadn’t thought about her in a while. It felt... weird.

I dunno.

Vinyl stood up and walked over to me. I was about to ask what she was doing when she wrapped her hooves around me. After a couple of baffled seconds I returned her hug. We just held each other, nothing sexy. She wept quietly onto my shoulder. I got the feeling she thought I was going to cry, but… I didn’t have any tears.

“Hey, Guilty?”

“Yeah?”

“My drink’s empty…”

I broke out snickering. “Sorry, Vinyl, No more painkillers tonight… that was the last of the coconut rum.”

She broke our hug and looked at me inquisitively. “There was rum in that?”

I nodded. “Two kinds, even.”

“Wow… I could barely tell.”

“I can get you something else.” I offered.

She was starting to cheer up… I think that hug was something she really needed. “Make me one of those things you were having,” she said.

“Sure. You, uh… you may not like it. It’s not very sweet.”

“C’mon, dude, make me a… what was it called again?”

“A Manehattan.” I began mixing. I was quite the little bartender tonight.

“Right… right.”

“Now normally… there’s a cherry in this, but I’m fresh out.”

“S’all good, man.” She was already back to her old self… her eyes were still puffy, and her mane was still a mess, but… she was smiling again. I placed the drink in front of her, and she took a sip. “GLAGH! What’s in this, dude?”

I giggled. “That’s the bitters you’re tasting. Strong stuff.”

She was scraping her hoof across her tongue. “Gimme that.” She grabbed the bottle of whiskey off the table and proceeded to gargle with it. “HOO… much better.”

'Straight from the bottle, indeed.'

“That bad?”

“Dude… so bad. How do you drink that?”

I shrugged. “I dunno… I like it.”

“Hmm… *sigh*… what do you think I should do, Guilty?”

“About your girl?” She nodded. “Can you still get in touch with her?”

“…Yeah, I… I could.” She sounded unsure.

“Well why don’t you just… I dunno… ask her if she wants to talk.”

“What do I talk about?”

“I dunno… tell her what you told me… about how you miss her.” I offered.

“You think that’ll work?”

“I don’t know… but it’s worth a shot. Don’t you think?”

After a moment of contemplation she nodded.

“Dude… Pinks was right. You’re... you’re just what a pony needs.”

“I’m glad you think so. And be sure to thank ‘Pinks’ for me. For the business, I mean.”

“No prob.” She stood up. “So I, uh… I think I’m gonna head out.”

“Yeah?”

“Yeah… what do I owe ya?”

“Well it’s… 3:15? Wow… that flew by.”

“Yeah, I’ll say.”

“So that comes out to 60 bits for three hours. You know, if I wasn’t so kind, I might charge you my overnight fee.” I was only joking.

“What would it be with the overnight fee?”

“An extra fifty, so 110”

“And what about the liquor?”

“Oh, uh, I dunno… 15 bits to replace everything maybe?”

“No way, dude, you made me three awesome drinks… good ones. Those were like… twelve bit drinks in a bar I bet…”

“Maybe ten.”

“Ok so call it thirty, throw in another 5 for that six pack… that’s, what, 145?”

“I’m not going to make you pay the overnight fee, Vinyl… it’s fine.”

“Dude… you were so beyond worth it. Plus don’t forget… I’m a fuckin’ millionaire. I can afford it.”

I wasn’t about to turn away more money. “If you insist.” I smiled like a jackass… I couldn’t help it.

“Damn straight… oh shit, where are my glasses?”

“Uh, in the bedroom, I think… I’ll go and get them for you.”

“Thanks.”

As I walked back into the bedroom, I noticed something had changed. There was now a record sleeve lying on my bed, under Vinyl’s shades. I picked it up. It was my Half Measure. The sleeve I’d laid next to my phonograph. Vinyl must have found it. I took a moment to look over the sleeve. I found something interesting in tiny font on the back. There was a blurb that read: “Half Measure’s Fiddlers Green, as performed by Octavia Philharmonic.”

Octavia… That’s a pretty name.

Either way, I brought Vinyl her sunglasses. She said good bye. I said thanks for stopping by. She told me I’d get a check in the mail, and off she went. I’m a ‘cash up front guy’ but… I trusted Vinyl. I didn’t doubt I’d get that check.

Oh… I just realized that cashing that is going to be awkward… I don’t really have a bank account. I’ve never had a bank account now that I think about it. I’m not even sure how to cash a check.

Oh well, I’ll figure it out.

Anyways, I headed off to bed. I didn’t actually fall asleep until the sun was up, though. Kept tossing and turning. I was… I kept thinking about the stable… about my fellow escorts. How were they doing? Were they still in the business? A lot can happen in two years, and I haven’t had contact with anypony from the city since I left.

I wonder how Crook is. When I left he wasn’t doing so hot. I should write him a letter. He should still be working at the stable.

When I finally did get to sleep… I had… dreams… vivid dreams. I…

This is hard.

I dreamt about….

C,mon Guilty, you can do this.

I dreamt about Sunny. About the time when we were together… if you can even call it that. And I dreamt… I dreamt about how much I used to miss her. I honestly… I honestly don’t anymore. That shipped sailed a long time ago, and I got over it. But I dreamt about all the things I used to do. I used to be like vinyl, missing her… looking around places we would hang out, seeing if she was there… wishing she’d be there when I woke up

And then I did wake up. And I was in my bedroom, alone. And honestly, I’m okay with that.

I hope Vinyl and her girlfriend… Octavia… I hope they end up happy… together. Ponies deserve to have somepony.

I hope Derpy does too… she deserves to be happy.

Speaking of Derpy, I have an appointment with her later this week, and I think… I think I’m going to ask her if she’d like to hike with me. I’m not exactly sure how I’m going to do that yet... but I am.

Anyways, I woke up an hour ago, hungover and vomiting, and I need to put food in me now.

Author's Note

Well another chapter down, and another glimpse into Guilty's past. I hope you all enjoyed it. As always, tell your friends (if they're into this sort of thing.) Llike and fave, too, it helps me out.

Days Off

Chapter 7

Days off

Dear Journal,

Well I had something of a little adventure today. My first hike with Derpy was interesting to say the least. I asked her to go with me last Sunday. I’ll admit I could have been a bit more… tactful in my asking.

“So… *huff*… would you wanna… *huff*… go for a hike?” I inquired.

“A… *huff* … hike?” Derpy asked, panting.

“Yeah… *pant*… I’ve been… *huff*… hiking lately, and I… *ngh*… I was wondering if… *pant*… maybe you’d want to… *huff*… join me.” I proposed as I slammed myself into her. Derpy had come by for her weekly visit, and I had finally worked up the nerve to ask her.

“Sure… *huff*… sounds like fuuUUUUUUUUUUUUUUUUUUUUNNNNNN!” She shook with orgasm for the twentieth time in as many minutes, and collapsed onto the bed in a heap, rear end twitching in pleasure.

“Yeah?” I was excited, grinning like foal.

“Yeah…*huff*… sure.” She tiredly rolled onto her back. “Hey Guilty… *huff*… go turn on the shower… *huff*… I’ll join you once… *huff*… once I can walk again, hehehe.”

“Of course.” Once I was out of the bedroom I couldn’t help but dance a little victory jig.

‘She said yes! She wants to go hiking with me! This is going to be so much fun!’ I can’t remember the last time I’d been so… giddy. I was just so excited. After several seconds I remembered I was supposed to be running a shower, and hurried upstairs, most likely blushing.

Once the water was flowing and the bathroom was steamy, Derpy made her way inside. “Geez, Guilty, what had you so enthusiastic today?” Asked a Derpy blurred through the glass of the shower door.

“How do you mean?” The shower door slid open, and an in-focus Derpy stepped into the warm shower.

“I mean you don’t usually have so much… I dunno… energy. You were working so hard the whole time.” She shook her head and sat down under her nozzle’s spray. She always does that. She never really showers when she’s over; she just sort of sits under the showerhead and closes her eyes. It’s like she meditating.

For whatever reason I decided I’d try that out. I’d already really scrubbed myself off after all, no harm in enjoying the spray. Honestly, it felt nice. The water was warm and the weather was cold. It was relaxing, just letting the water heat my tired body.

“I dunno, Derpy. Maybe it’s all the hiking I’ve been doing. It’s really good cardio.”

‘Or maybe I just got a little too excited at the prospect of having a friend to go hiking with.’

“Yeah, apparently. Hehehe. That was a great big one at the end there. I thought my hips were gonna fall off.”

I laughed. “So far, I’ve yet to actually fuck a mare in half, so you should be safe.”

“HAHA! You’re so funny, Guilty.”

We enjoyed our shower for several minutes after that, in our normal quiet peace. There was something calming about sitting in the shower in quiet contemplation. My mind wandered for a while… to good places… to bad places... all over. I thought about home. When I say home, I mean Manehattan not… not home home. I thought about Crook, and the time he kicked a cop in the balls. I thought about the day I learned I was no good in a fight… the hard way. I thought about the day Crook told me he’d found a way for us to make some money… the day we went to the stable together.

Honestly I almost fell asleep, which would’ve been embarrassing. The sound of Derpy opening the shower door snapped me out of my sleepy trance. We stepped out and dried off and whatnot. It wasn’t until we were downstairs that I remembered something important.

‘Muffins! How could I forget?!’

I quickly put a kettle on the stove. What was a muffin without tea?

We sat at the table and… as ever… I asked her the usual question. “So… any luck?”

She stared deeply into the table, a sour expression on her face. She just shook her head.

‘That’s not normal. She’s not usually so upset. She usually gives me a casual ‘meh’ and regales me with her latest attempt at romance. Something’s wrong. Something happened. Did someone hurt her?’

“Is something wrong?” I tried and failed to sound nonchalant. “Did something happen?”

“Nothing happened, Guilty.” She wasn’t lying, but… but something had her upset.

“Then what has you so gloomy?” I was honestly asking myself more than her.

She sighed deeply. “Well, that’s just it, Guilty. Nothing happened. I’m… I dunno… I just don’t feel like putting myself out there all that much anymore.”

Derpy? Giving up? I didn’t know what to say. “No way,” was all I could manage.

“It’s just… after 3 years of being single I’m… *sigh*... I’m tired of it Guilty.” She sank onto the table, lying face down on the cool surface. “I’m tired of putting myself through rejection after rejection after rejection. AND I’m tired of putting Dinky through that too.”

“Dinky?” I was confused. How did Derpy’s love life affecting her daughter?

It took a moment for me to get a response. “She told me the other day… about that fight she got into.”

“Yeah?” I was looking for a connection, but I wasn’t seeing it.

“So this kid… I thought he was making fun of her or something, you know? Well it turns out he wasn’t. He was… he was making fun of me, Guilty.”

“Of you?” Still lost.

“Well apparently…” She cleared her throat. “One of the stallions I asked out was… was this kid’s dad.”

“Ooooooh…” There it was.

“Yeah… I… I don’t even know who to be honest. I didn’t think anypony I asked out had kids.” She buried her face in her hooves. “I feel so bad, Guilty. Dinky was just trying to stick up for her mom. It’s all my fault she got into that fight.”

“Oh that’s bullshit.” I didn’t even realize I’d said it out loud.

“Wh-wha?” Derpy was flabbergasted, and rightfully so. I usually try to be delicate with this sort of thing. But that? That was something Close would say.

“Well I mean…”

‘Okay, Guilty, rein it in. Your Manehattan is showing.’

“Ok sure… if you hadn’t asked out that guy then Dinky may not have gotten into a fight. But I mean… That same is true of that guy telling his kid… or that kid teasing Dinky… or even dinky clocking him with a lunch pail. All you did was ask a guy out. You didn’t do anything wrong.”

Derpy wasn’t so sure. “I… I dunno, Guilty, I just… I feel like a failure.”

Her self-pity was actually starting to make me a little mad. I don’t like people talking smack about people I like… even if it’s them. “Oh, come on… why? Cause you can’t get a date?”

“Cause I can’t find a daddy for my little girl.” She looked me dead in the eye. She wasn’t sobbing or tearing up. More than anything she was… frustrated. “A girl needs dad, Guilty. Right now all she’s got is… one unfit mother.”

I got a little… heated, to say the least. “Oh, please. Quit feelin’ sorry for yourself. You’re a fantastic parent.”

“I dunno, Guilty.” She groaned. “I just feel like between my job, and errands and everything, I never have time to be there for her.”

“Oh please you’re-!” I stopped myself, took a deep breath, and continued. No sense in starting a fight over this. “Look… Derpy. I’m not saying your situation is ideal. And I’m not saying that Dinky doesn’t deserve two loving parents like any kid. I’m just saying, you’re far from being an unfit parent. And so what if you can’t find a stallion. All she needs is one good parent for her to turn out halfway decent.”

“You say that but… but she’s the only kid I know at school who only has one parent. I don’t want her to get picked on for it.”

I could only scoff. “I think she’s already proven she can kick the flank of anypony who looks at her sideways.”

That made Derpy giggle. “Hehehe. That’s true.” She let out a long sigh. “I guess it’s just… I feel like so much of the time I don’t know what I’m doing.” It was at that point that the kettle started to whistle.

“Hang on… lemme just…*sigh*… we’ll finish after muffins.”

And what muffins they were. Corn muffins. Golden sunshine given solid form. Still warm and soft, crunchy exterior. Little kernels of corn adding bursts of flavor in each bite. Perfect with a nice green tea. And with butter. My Heavens! The butter soaked into the spongy muffins making each bite a luscious delicacy. Surely they are meant only for the elitist of nobles. NAY! Only for royalty!

I’m sorry I got a bit carried away there.

And I have an erection, apparently.

Anyways… uh… yeah… after muffins we kept talking.

“Ok so… where were we?” I asked, brushing tasty morsels from my lips.

“I was a… just saying that I don’t feel like I know what I’m doing.”

“Right right. Well look, honestly I can’t help you there. I don’t know a damn thing about raising kids. But I know enough about bad parents to be able to spot one.” I took one last sip from my teacup, emptying it. “You, Derpy, are not a bad parent. You care about your kid. You make time for her.”

“Meh, what do you know?” She smiled at me. She was back to her old self.

It was then that an idea popped into my head. It was a foolish idea, one of those ideas that I’m chalking up to whatever weird funk has been running through my head lately. It was one of those, ‘I’m gonna tell a client waaaay too much about my personal life’ ideas.

“You wanna know what I know?” I asked her.

“Huh?”

“About bad parents… you wanna know what I know?” It wasn’t because I thought it would help give her some perspective or… whatever. I just… I wanted to tell her. Not cause I wanted pity, mind you. I hate throwing a pity party. I just... I just wanted her to know. Like I said, I’m blaming it on whatever weird mood I’ve been having lately.

Derpy was just confused. “Uh… I guess so.” She just shrugged. I don’t think she really knew where I was going with this. Honestly, neither did I.

“Well… I’m not sure how much you’ve gathered, but I was raised by a single parent. I... I never knew my mother. I don’t know if she passed or… skipped town… I dunno. My father owned a bakery. He, uh… he was a pretty heavy drinker. He’d come home late… drunk… angry about something or another. When he was like that I… I knew to stay out of his way. Anything would set him off… hell sometimes even nothing at all. He… he, uh… well there’s… there’s no nice way to put it. He used to hit me.”

Derpy’s face was hard to read. Not the shock or horror I was expecting. No tears or sadness of any kind. She was… serene, like she is in the shower minus a smile. She was listening, though, that much was certain. I think… I think she knew that I just needed to talk. I think she understood that. Maybe. I dunno. I was a little too distracted to … read her. I reached up into my mane and pulled it to one side. I bent my head low, so Derpy could see.

My scar. I mean I’ve got a few, and not all from my father; but that’s the big one. The one up behind my ear. “You see that there?”

“Mmhmm” No change in expression.

“Ok so… one night, my father comes home. Drunk, as usual. It was late… waaay past midnight, Probably around three. I was lying in bed, and I… I just heard him shout. He called me to the kitchen. He was… he was so loud. Needless to say I already knew what I had in store. So I pulled my gangly little self out of bed and made my way over to him. He just… reeked of booze. Whiskey and beer. Well it turned out I’d left the kitchen light on, and he was furious. I just sat there listening to him rant about money and how I didn’t appreciate what he did for me.

“Now, mind you, I must’ve been… eleven… tops. And it was… it was snowing that night… yeah.” Details made themselves clearer in my mind. A night I had tried to forget was creeping its way back into my mind. “I was cold and tired and after I don’t know how many minutes of listening to him shout, I started to get drowsy. I yawned. And that’s all it took. He hit me… hard… and he kept hitting me. Now normally he’d smack me around a few times, and tell me to fuck off. But that night… I can’t tell you why but that night he didn’t let up. He just kept… hitting me and hitting me until… until I blacked out.

“I woke up in the Hospital. My dad had told the doctor that I was out late or something… got beat up by a kid from school. I had a concussion and…” I swallowed. “…and my ear had damn near been beaten off my head. Luckily I got there quick enough that some unicorn could heal it back. I still don’t hear perfectly out of it, to be honest, but… it’s a lot better than it used to be. So... yeah.”

I was fairly proud of myself, actually. I hadn’t exactly planned to tell Derpy anything but I managed not to tear up or break my act at all. I was just… talking about it. It felt… really good to tell somepony who would listen.

Well whatever the case, I needed to bring this back around somehow to help my favorite client. “So my point is, Derpy. That man… that… poison stallion was my only parent… and my only real role model until I was thirteen.” I gestured to myself. “I turned out alright. At least I think I did. Derpy you’ve told me just about everything you do with Dinky. You make time to be there for her, you work hard to provide for her, you play with her, you administer reasonable punishments when she acts up. You love her… and she knows you love her… and she loves you. I mean she goes around defending your honor for Celestia’s sake.”

She smiled at me. That warm shower smile. “You always know just what to say Guilty.” Her face fell slightly, and she grappled with a question for a bit. “Nopony ever called protective services or anything… nopony noticed your bruises or... or called the cops when your dad would shout at you?”

“I got into a lot of fights and...” I laughed nervously. “...I don’t think I ever won a single one. I had bruises all the time, so… anypony who did noticed must have figured I just got the snot kicked out of me by somepony. That, and it was a pretty bad neighborhood. Half the kids at my school had parents just like mine. It wasn’t exactly uncommon.” I gave her a reassuring grin. “But hey, that’s all in the past. I’m in a much better place now. And I don’t just mean Ponyville.”

She nodded her head. “Hey Guilty?”

“Hmm?”

“I used to think I had it bad… I mean with my eyes and all.” She pointed a hoof at her mismatched orbs. “But that… geez… I don’t know if I could’ve come out of that as well as you did.”

“Oh it wasn’t all bad. I was just trying to make a point.”

“But still… in spite of all that… in spite of everything that could’ve crushed you… You’re still you, Guilty. You managed to come out of that without… without… without turning out really fucked up. You’re…. you’re strong, Guilty.”

“I’d never really thought of myself as being strong.” It was true. Smart? Absolutely. Handsome? Better believe it. Observant? Disgustingly so. But Strong? Not so much.

“Well… you are, Guilty… you are.”

I wasn’t really sure what to say to that. “Thanks, I guess.”

“Well, anyways Guilty… I gotta get home.”

“Of course. OH wait… uh, when’s a good time for you… for the hike I mean.”

“Ummm… Friday’s a Holiday… sound good?”

“Sounds great. Stop by around… ten?” I was so excited… hiking… with Derpy. With my friend.

She gathered up her things and walked out the front door. “No problem. Bye Guilty.”

“Bye Derpy.” She left. Twenty paces out she turned around and waved… just like always. I waved back… just like always. I was done for the day, but I still had much to do. After all I had a hike to plan! But where were we going to go?

“Smoky Mountain? Are you serious, kid?” Close asked as he double-checked my sideburns for evenness.

“Yeah.” I explained. “I figure if we take the 9:30 train we’ll get there by noon, we can eat lunch at the base, and then take the ridge trail. It’s not that bad just 10 miles or so, so I mean-”

“Okay, first of all: shut up, you’re a moron. Second of all: hold fucking still or you’re gonna end up with a fuckin’ bald spot.” Close chastened, as his scissors continued to click through my mane.

I sat quietly, waiting for some elaboration. I received none. I let out a defeated sigh. “Why am I a moron, Close?”

His scissors paused. “Oh, I see how it is. Now you want my advice. Advice that, I might add, you opted to take, after you so unceremoniously refused to pay for it last time. Well aren’t you just a real Piece o’ work, Guilty.” I could see him shaking his head in the mirror. He was just playing around, which meant I was going to have to play along with him.

I groaned. “Fine, there’s a nice big tip in it for you if you properly explain to me why I am a moron, Close.”

“Oh, how very gracious of you, Guilty. Aren’t you just the fucking picture of charity. How truly kind of you, your fuckin’ majes-”

“Close. Sometime today?”

He grumbled bitterly. “Fine… ya fuckin’ ingrate.” He muttered not quite under his breath. “Anyways, the reason you’re a complete and utter moron is simple. If you think you’re gonna take a newcomer on a ten mile hike you’re fuckin’ delusional. She’s gonna get tired, and then you’re both gonna turn back, and then she’s gonna feel bad about making you turn back, and she’s not gonna wanna go hiking again and then BAM… no more girlfriend.”

“She’s not my girlfriend Close… it’s not a date.”

Close looked skeptical. “So what, she’s client then?”

“Yeah, she’s a client.” I explained.

“So she’s paying to go hiking with you?”

“N-no, we’re just… going for a hike... for fun, you know.”

“Guess what, Guilty?” He sounded so smug.

“What?”

“That’s a date.”

“Oh, shut up y'old bastard! I don’t have feelings for her. At least not like that.”

“And yet, you lead her on like this. For shame, setting up a quiet secluded rendezvous with a girl you aren’t invested in. No heart, kid. No heart at all.” Close teased.

“It’s not a date, Close.” I practically snorted. I knew he was just messing with me, but it was sort of pissing me off. “She’s just a platonic female friend.”

“No such thing.” He said very matter-of-factly. “Watch, by year’s end you two will be bumping uglies.”

I rolled my eyes. “Close, you relic, she’s a client. We’re already doing that.”

“See? What’d I tell ya? Never doubt me, kid. I got decades of wisdom on you kid.” He laughed, I walked right into that one.

At that point I just wanted to change the subject. “Anyways… What do you think I should do then? About the hike I mean.”

“Take her somewhere easy… somewhere you know real well. That way you can show her the ropes. You know… impress her. Mares love that stuff.” He wiggled an eyebrow suggestively

“I’m not trying to impress her, Close. I’m just trying to spend a little time with a friend, doing something I really enjoy.”

“Which reminds me, where did this ridiculous little love affair with fuckin’ hiking come from?”

“How do you mean?” I asked.

He floated his scissors back onto his counter, and pulled a comb out of his little glass of barbicide. “I’m just saying… a few weeks ago you didn’t have a fuckin’… extracurricular activity to speak of, and all of a sudden you’re all bright eyed and bushy tailed over hiking of all things. S’fuckin’ weird, kid.”

I would have done a double take if I didn’t have to keep my head still. “Close, you were the one who said I needed a hobby. I got one. So, what, it’s ‘fucking weird’ that I followed your advice?”

“Hey, watch yer fuckin’ mouth.” I swear, there’s just no way Close hears himself talk. “And what’s fuckin’ weird, Guilty, is that you seem to have just taken up the weirdest fuckin’ hobby for a manehattan pony.”

“Well, that’s kind of why I like it, Close. I’ve lived my whole life in a city. Until Ponyville, I never knew anypony with a front yard. I’ve never really had the chance to appreciate nature. Now I have that chance, it’s really nice Close. Just… getting away from... everything. Nopony for miles in any direction. It’s great.”

“Hmmm.” He grunted. “I guess I can understand that. I spent a few months stationed in a little town called dodge junction once upon a time. Going out on patrol in the desert every now and then, yeah, it’s pretty nice.” He admitted. “What put hiking into your head anyways?”

“Do you know Pinkie Pie?” I asked

“Everyone knows Pinkie Pie… is she a client?”

“I’ll never tell. But she told me that somepony who works indoors needs to get out to relax.”

Close just nodded his head. “Makes sense…” He began to brush the wispy bunches of my hair off of my smock, which floated daintily to the floor. “Oh and thank you for coming in before you looked like a fuckin’ asshole this time. It makes this much more fuckin’ bearable.”

“Some girls like long hair, Close.” I teased.

He let out a heavy sigh. “Poor girls… chasin’ a bunch a’ hippies around. It’s a damn shame.”

“Well… whatever, Close. Here’s… 16 bits.” I produced a small pile of gold.

Close glared at me.

“That’s generous as hell and you know it. Plus, it’s all I got on me.”

Close continued to glare before until he ultimately snatched up the coins. “It’ll do. Ya fuckin’ tightwad.” He pocketed his bits. “And if I gotta remind you to watch your mouth one more time, Your money’s not gonna be any good here anymore.”

“Yeah yeah… sorry, Close.” He says that every third visit. “Anyways, thanks for the advice… I think I know where we’re gonna head.

“Oh yeah, where to?”

“Ghastly Gorge. I know the Route pretty well, and there’s some cool stuff to see.”

“There ya go, nice and flat, plenty of shade… that’ll sweep her off her hooves.”

I facehooved. “Again… not a date.”

Close Scoffed as he began sweeping up what remained of my haircut. “Whatever you say, Guilty.”

The day arrived. I had almost been too nervous to sleep. Out… hiking… with a friend. It was so exciting. I got up early to prepare. I made myself a trail mix. Nuts… berries… some mini pretzels. Tasty stuff. I made sure I had plenty of water, a map and a compass (just in case) and a few granola bars. I also made a big lunch for Derpy and myself: Some nice hearty sunflower sandwiches.

There was a knock at the door. I almost ran to the door. I felt so… foalish. Here I was getting so eager over a little hike. I knew how I should have felt. I knew I needed to be casual about this. If I acted so excited over a little hike with a friend I was going to come off like a weirdo. It’s just… I never really done this before. I’ve never had a casual friend before. Certainly not one who was also a client.

Anyways I made a point of calming down before I opened the door.

‘Ok, Guilty, relax… just going to be a nice hike with Derpy…’

I opened the door. The practiced casual smile just melted off my face.

‘… and Carrot Top.’

There she was that fuzzy orange ball of bitch, a fake grin plastered on her face. ‘What is she doing here?’

I almost just sat there staring at her before I remembered myself. “Hi Derpy. Hi…uh… Ms. Harvest, right?”

“Yes, that’s right, Mister… Pleasure, was it?” She said somewhat stiffly. I may have mentioned this before, but she’s not a terrific actor. I could tell she was nervous. She was sweating; she couldn’t make eye contact; her smile was slowly cracking.

“Mmhmm.” I smiled. I didn’t want to smile. I really didn’t want to smile. But I did… for Derpy’s sake.

“Goldy was free, so I invited her along. I hope you don’t mind.” Derpy was so cute, smiling like the sun. I… I couldn’t be mad at her.

“No trouble at all. Come on in.” I ushered the two into my home when I realized something. This was the first time either of them was here not as a client. I was suddenly nervous. These weren’t clients… these were guests.

“So, uh, I packed lunch. I wasn’t planning on three ponies, but there are plenty of sandwiches. I also packed snacks and water.”

“Geez, Guilty. You really do love hiking. You’re all prepared and everything.” Derpy said with a slight giggle.

Carrot top tentatively spoke up. “All that sounds… heavy. Will you be carrying it?” Something told me it wasn’t so much a question as a request. And while I wasn’t on the clock for Carrot Top, I actually had been planning to carry it all.

“Yeah, I got it.”

Derpy looked over to me, worried. “Are you sure, Guilty? That’s a lot of stuff.”

“Yeah, it’s no big… plus it’s a fairly flat trail anyways.”

Carrot top spoke again. “So where are we going, hmm?” She managed not to sound too bitchy.

“Just along the north side of Ghastly Gorge.”

Derpy clicked her hooves together. “Oh, I love Ghastly Gorge. I haven’t been there in forever, either. This is gonna be fun.”

“Yeah… fun.” Carrot Top scoffed. “Just lemme use the bathroom and we’ll do this.” She started towards the stairs. That was a mistake.

“Upstairs, first door on the right!” I called out very pointedly. Carrot Top had forgotten that she wasn’t supposed to know where the bathroom was.

She stopped briefly in her tracks. “Thank you, Guilty.” She said, before continuing along her way. She wasn’t doing a very good job hiding her malice. If she didn’t rein it is Derpy was going to notice.

“Sorry she’s in such a bad mood.” Derpy said. Apparently she already had noticed. “And sorry I brought her without asking. She just really needed to get out of her house for a while.”

“Oh?” This was interesting… a glimpse into the home life of Carrot Top. Maybe there would be any clues as to her shitty mood around me, anything that might help shed some light on the semi-regular migraine in my life.

“Yeah, she and her girlfriend are fighting again.”

Mind… BLOWN!

Carrot Top had a girlfriend? The cock hungry indifferent shell of a client that came to me with nothing but a need for raw hetero coitus… had a girlfriend? This was too much.

“So *ahem* is this a… recent relationship or…?” I asked somewhat awkwardly.

“Nah, they’ve been dating since before you moved to Ponyville. They fight like this every month or so. They just need some space.” Derpy waved a hoof dismissively.

“Huh…” I was dumbfounded. I wondered if Carrot Top’s girlfriend knew she came to me. I wondered in maybe Carrot Top wasn’t really straight. I had always assumed I was being used as a substitute to some stallion, but maybe she just came to me to get away from her relationship.

“Something wrong?” Derpy asked. I had just been staring at the staircase, apparently.

“Hmm? No nothing wrong.” I shook the idle thoughts from my head. “Can I get you anything before we head out?” Derpy just shook her head.

Eventually Carrot Top finished up and the three of us set out towards the Gorge. The walk there was mostly quiet. Carrot Top was completely silent, and Derpy only hummed some tune. It was almost comedic, the difference between their expressions.

Derpy was so… bright and happy. Walking along in her normal bubbly manner, her head bobbed in time to her private song.

Carrot Top was anything but bubbly. Hunched over, staring at the ground, pretending desperately she was anywhere else, she was… trudging. That’s the only word for it.

When we got to the Gorge Derpy was practically dancing. “It’s just as big as I remember.” She started running full tilt towards the edge.

I started to call after her. “Careful, Derpy, that’s a long way-”

That was as far as I got before she tripped over her own hooves and tumbled over the edge.

“DERPY!” Someone shouted. I’m not sure if it was me or Carrot Top.

Before I realized it I was running full tilt towards the edge. I think Carrot Top must’ve been running with me. I barely had time to skid to a halt at the cliff face. My body nearly reeled over the edge as well.

I was already preparing myself for the worst. My eyes shot every which way down to the canyon floor, looking for any blotch of grey and blond amongst the stones and foliage.

Next to me carrot top breathed a sigh of relief. “Damnit, Derpy! Don’t scare me like that!” She yelled. I quickly looked to her, then followed her gaze to a spot several yards down and away from the cliff’s edge.

There was Derpy, hovering in the air, safe and sound, wings keeping her aloft… upside down.

“I’M OKAY!” She shouted.

It was only then that I realized how much adrenaline was flowing through me at that moment. It all hit me at once: how hard my heart was pumping, how fast my lungs were breathing, how much I was shaking. I collapsed onto my rear end just staring at Derpy. I had honestly thought she was hurt… or worse.

“Right…” I panted. “… Wings…*huff*”

“yeah…” Carrot Top said, somewhat begrudgingly.

“*huff*… Hey, Derpy!” I yelled.

“What?” she called back as she struggled to right herself in the air.

“You really are clumsy!”

“Hee hee… Told Ya!”

After several flips Derpy finally got right-side-up. She was actually kind of hilarious. She kept trying to get upright, but every time she did she went full circle and wound up upside down again. I did my best not to laugh, while Carrot Top just shook her head.

When she finally landed, she was staggering hard. “Woooah… dizzy.”

That’s when I lost it. I just exploded into giggles. It was too much.

Once she got her bearings Derpy threw me a mock glare, while Carrot Top threw me a very real one.

“Sorry, but you have to admit that was pretty funny, right Miss Harvest?”

She was taken aback. I never really engage her during my sessions. She doesn’t want me to. But here I was, openly asking her a question. I could tell she was upset. I could tell she was furious with me. She just wanted to get through this hike without making Derpy suspicious.

But I didn’t care. I wasn’t on her clock. I wasn't on anypony’s clock. This was Guilty time. I could do whatever the hell I wanted. If Carrot Top didn’t want to answer my questions, fine. If she didn’t want to talk to me, that was fine to. But she couldn’t stop me from asking those questions. She couldn’t stop me from trying to talk to her.

This was my hike I and was going to enjoy it, Damnit!

“R-right.” She muttered, downtrodden.

“So anyways, Guilty. Where’re we headed?”

“I just figured we’d head south along the trail, there’s some cool caves on the Eastern face, old Eel nests, I think, so we’ll get a good view of them if we head along the west side.”

“Wow, Guilty, you really did put a lot of thought into this.”

“What can I say? I wanted it to be fun.” I may or may not have spent a few… hours comparing the pros and cons of the trails on either side of the canyon.

After our little scare we started the real part of the hike. It was heaven. Nature everywhere, a fantastic view the whole time, the light pouring over the rock face, the mystery of the dark empty caves, pleasant conversation with Derpy, the occasional snack, it was just perfect. Carrot Top even got into the conversation a little bit, if only when prompted. We talked about all kinds of stuff. Derpy was talking about Dinky, about her mail route, about her and Carrot Top as kids. Apparently after the two of them became friends, they really became inseparable.

Getting into fights together, studying together for tests, their families even planned joint vacations for them so they never had to be apart.

They reminded me of Crook and myself.

All their stories about when they were kids kind of got to me though. I mean so much of what brought them together was school. I never finished school. Once I had a job, I never bothered with school… and that was when I was 13. I mean, I still learned plenty. And I don’t just mean street smarts, I mean I’ve got at least a decent amount of book learning. As an escort you need to be able to keep your client mentally stimulated if necessary. As I’ve said before, you need to seem like an expert in everything.

And hey, if your client doesn’t want a smart stallion, you can always play dumb. It’s a lot harder to play smart.

Eventually it was lunchtime, so I laid down a blanket and the three of us ate the sandwiches I prepared. They were good. The sunflowers were perfect. Luckily I’d made more than enough for two ponies, so we all ate well. Carrot Top seemed upset about something… well more than she had been already, and Derpy took notice.

“Whatsa matter Goldy?” she said, voice full of sincere worry.

“Nothing, Derpy, don’t worry about it.” She smiled, but something was definitely bothering her. Taking a bite of my sandwich, I opted to take a closer look at her.

‘She’s slouching a little, but that’s probably just because she’s tired. She’s sighing a lot, not breathing heavy but sighing (there’s a subtle difference,) so she’s upset about something. Her eyes are downcast, so she’s probably think about something else entir- wait a second. She’s not just staring down; she’s staring at her sandwich.’

“Is the food okay?” I asked her.

Derpy, however, was the one to respond first. “Yeah, Guilty, It’s awesome… they’re just as good as last time you made them.” She happily bit into what I believe at that point was her second sandwich. Her head happily bobbed as she chewed.

“He makes food for you?” Carrot top asked Derpy, a befuddled look on her face. I can understand why she’d be confused, I’ve never done anything with Carrot Top aside from her usual routine.

“Uh-huh… Guilty’s really good at cooking.”

Such praise. “I’m okay at cooking, Derpy. You’re the muffin virtuoso.”

Derpy blushed a tad. “Don’t say it like that… it’s embarrassing. But I’m serious, Guilty. You’re a super good cook, right Goldy?” I honestly think that’s the first time I’d seen Derpy embarrassed. Flushed, sure, but that was for… other reasons.

Carrot Top’s response was cold, almost mechanical. “Yes, Derpy, it’s… delicious.” She sounded… pissed… pissed that my sandwich was so good. That’s what it was… she didn’t like that I was a good cook. What exactly was she mad about, though? Was she jealous of Derpy? Jealous that Derpy got “better” sessions than her? Was she angry at me for not giving her the same treatment? I tried and failed to wrap my head around it.

My special talent may be reading ponies; but when I’m working with a mare as… unexpressive as this one was, I can only do so much.

“Then what’s got you all bummed, Goldy? Is it Lily?”

Carrot Top clicked her tongue. “Damn it, Derpy! Can we not…!” For the briefest of instants her eyes met mine. “can we not do this right now.”

Derpy looked hurt. Lip quivering, tears in her eyes, the whole shebang. “Sorry, Goldy, I was just trying to help.”

‘She yelled at Derpy… for just trying to help… what a bitch!’

“It’s…*sigh* It’s alright, Derpy. I just… I didn’t want to bother Mr. Pleasure, here, with my… domestic issues.”

‘You mean you don’t want me to know anything at all about you… what a bitch.’

“Aw, but he’s really good at that stuff. He’s the one who always cheers me up after a bad date, or I get shot down, or whatever.” Derpy put a hoof on Goldy’s shoulder. “He’s also really good at keeping secrets and stuff, you can trust Guilty. I’m sure he coul-“

“Derpy, just drop it...!” Her gaze met mine again… for longer this time. “…please.”

“Okay, Goldy… sorry.” Commence sulking.

‘She snapped at Derpy! Again! What a bitch!’

After a brief pout, Derpy looked up at her sandwich once more and began eating. After a single bite, she was happy and bubbly again.

‘I can’t believe this bitch. She’s supposed to be Derpy’s best friend? Is she always this short with her? If Derpy wasn’t here, I might have half a mind to give her a stern talking to. Then again, she could probably kick my ass. Then again, she might not call my bluff, and if she does, I might have the element of surprise. If I get her in a headlock-’

“Guilty, How come you’re staring at Goldy like that?”

“Huh?” I didn’t realize it, but I guess I had been staring at Carrot Top sort of... intensely. That was sort of embarrassing. “Sorry I was…” Carrot Top was now glaring at me. “…elsewhere.”

“I’m sure.” Said Carrot Top, rather cattily.

Derpy polished off what remained of her sandwich and stood up. “I’m gonna give my wings a stretch… look around a little.”

“Mmmkay, take care.” I offered.

“Be careful.” Chided Carrot Top.

“Geez… you and Dinky.” Said Derpy, dismissively, before taking to the air and flying off down the trail, leaving me… all alone… with Carrot Top… *sigh.* Once Derpy was out of sight, my remaining companion made a very barefaced point of turning completely around to ignore me.

So this was the game, was it? Just sit quietly and wait for Derpy to get back, so the two of us can get back to pretending we don’t hate each other. Sounded like looooads of fun.

‘This blows… all alone with Carrot Top. I can’t think of a worse way to spend an afternoon. Scratch that… replace Carrot Top with Applejack… that’s worse. Man I just have to sit here and keep quiet because…’

It was then that I had a moment of realization. So soon was I to forget that I was not on the clock. This provided me with a rare opportunity. I could say whatever I wanted to Carrot Top. She could shush me all she wanted, but I was free to ignore her just as much as she usually ignored me. I could say anything to her. I could tell her off. Let her know how much her sessions take out of me. Yell at her about how she treats Derpy. I could say anything, and it wouldn’t infringe upon my professionalism. She may have been my client, but I was not a whore today.

‘But where to begin. I could tell her that fucking her makes me cry, which is technically true. I could list off any number of reasons she’s less than enjoyable company. OOOH! I could-’

My mind came to a screeching halt. What was I doing? I was imagining creative ways to berate a slightly less than polite mare. No, a slightly less than polite client. Where was all this even coming from. Okay, maybe I’m not a huge fan of Carrot Top, but I don’t hate her… that much.

So what do I do? Have a heart to heart with Carrot Top that changes the face of our relationship for the better via some sort of emotional rollercoaster wherein Carrot Top and I Laugh, cry, and learn the true meaning of friendship? Fat fucking chance. So what then? If nothing else this was a chance to get to know Carrot Top.

It always sucks to be the first person to talk after an awkward silence. No matter how suave you are… breaking the ice is never fun.

“So… Lily?” I hazarded.

“Not. A. Word.”

I shook my head (even if she couldn’t see it.) “Mm-mm. Not today, Carrot Top. I’m not ‘on duty’ right now.”

No response.

“I just ask because… well… I didn’t exactly peg you as, you know… having a girlfriend. What with all the sex we have and everything.”

“Would you shut up!”

“I would if maybe you’d fill the resulting silence with your own words. You know, almost like a conversation. In fact… exactly like a conversation, like… I talk, and then you talk, and then I talk, and so on.” ‘Just because I’m trying to be decent doesn’t mean I can’t be snarky.’

No response.

“So anyways, back on topic… Does this ‘Lily’ know that you come to the town whore every few weeks? Because I don’t want some crazy heartbroken mare showing up on my doorstep with a knife claiming I destroyed her relationship.”

No response.

“You know, for somepony who comes to me more often than most of my clients, you probably make the least use of the services I have to offer. If you tried actually talking to me you might enjoy it. I’m quite good at conversation. I get lots of practice, after all. All my other clients talk to me. They get to know me a little. Well… that’s not entirely true… they get to know my persona… They get to know Guilty Pleasure. Only a few actually get to know me. Like Derpy… she actually thinks of me as a friend. At least I think she does.”

No response.

“Look, Carrot Top… if nothing else…then for Derpy’s sake, could you at least try to get to know me. Since Derpy doesn’t seem to mind being seen in public with me, I’m actually making a point of being her friend. You see that’s a very rare thing here in Ponyville. Most clients… even the ones who are actually nice to me… don’t want anything to do with me. I value having a friend I can go places with and have fun with, and I intend to do it a lot more. You’re her best friend, so I imagine our paths are going to cross. It would behoove you to at least be able to pretend you don’t despise me.”

No response.

“I’m not saying we have to talk about anything personal; just forget I mentioned your girlfriend. Just… just treat me like a fucking pony, would you? Be able to have a polite conversation with me for Celestia’s sake. We can talk about anything: your business, current events, the fucking weather.

No response.

“However you feel about me… you really need to do a better job hiding it, or Derpy is going to notice. And I think you know better than I that if she notices something, she’s going to ask questions, and she’s going to try to help, and that is the last thing you want. At least… as far as I can tell. So maybe humor me. Rather than trying to hide how you feel about me… why don’t you give changing how you feel about me a shot. I mean, Derpy likes me so why-”

“That’s because she’s too trusting.” She stated.

“See… just like that! Now this is a conversation!” Snark snark snark.

“What is your problem?” Her head whipped around to face me, livid.

“My problem is that I am trying, very hard I might add, to get along with a friend of a friend, if only to try and make that friend happy. And despite the fact that this friend of a friend is supposedly my friend’s best friend, she is not even making a goddamn effort to get along with me.”

“Why are you even hanging around Derpy anyways? What’s your angle here? Is it money you’re after? Trying to get her to pay for more time with you? How much are you charging her for this little hike, huh? You know, she has enough trouble getting by without you squeezing her for bits.” She was practically interrogating me.

“…What?” Apparently Carrot Top had gotten the impression that this little adventure was costing Derpy a small fortune. “She’s… she’s not paying me a single bit. I on the other hand must’ve spent twenty bits of sandwich makins and snacks and water. I’m not going to charge a pony to just... relax. And my ‘angle’? I like talking to Derpy, she’s cheery and a blast to hang out with. My ‘angle’ is I’m trying to spend time with her.”

She snorted and actually stood up. “Yeah sure. You say that now, but in a month, you’ll just be another stallion trying to take advantage of her trusting nature, just reaching into her wallet.” She turned around and slowly started making her way over to me. “I’m not going to watch another stallion hurt Derpy like that… hurt Dinky like that.” She stuck a hoof in my chest. “So why don’t you just back off.”

I stood up to meet her burning gaze with my own... lukewarm gaze. “*sigh*…Ok, you’re whole little ‘I used to make fun of Derpy as a kid and now i feel bad about it so I take it upon myself to protect her from all the dangers of the world since I can never truly pay her back…’ THING is adorable and all. But in all seriousness you need to chill out.”

“You… what do you…? Just… shut up… okay?” Suddenly the bat out of hell was on the defensive. That struck a nerve. She’s heard that little speech before.

Epiphany.

A hint of a grin started creeping onto my face. “Oh I get it… that’s what you’re fighting about with this Lily character.” She swallowed hard. I was right. “That’s it isn’t it? She feels like she’s playing second fiddle to Derpy.” I could feel a big fat stupid smile just splattered all over my face. I was enjoying this a little too much.

“How… how did you…?” The color was draining from her face.

“HA! Oh that’s just too rich.”

“Please… you… you can’t tell Derpy.”

I snorted in laughter. “*sssnrrk* No fucking shit. It would break her heart. Plus it’s frankly none of her business.”

“It’s none of yours either!”

“Well then maybe you shouldn’t have had such an obvious tell.”

“You’re unbelievable.” She groused.

I coughed to try and kill my case of the giggles. “Okay okay, serious now. *ahem* Do you two fight about this a lot?”

“Oh, I am not talking about this with you.”

“Oh, but you should. I’m good at this. You can ask any of my clients. Or rather, you could if I ever told you who they were... which I won’t.”

“Yeah, real helpful.”

“Fine be that way… but don’t say I never offered.”

“Oh don’t worry I won’t be telling anypony anything about this little conversation.”

“Luna, you are just so determined to not be cool with me.”

“I still think you’re not to be trusted… and I will be keeping an eye on you. I swear if you hurt Derpy at all, I’ll-.”

“Oh give it a break. Derpy’s a grown mare, she can handle herself. You best learn that for your sake and Lily’s.”

It was at this moment… of all moments… that a noise from the distance began to make itself known. Carrot Top and I paused out conversation to listen. It was an odd noise… almost like the sound of leaves blowing in the breeze but… off. “You hear that?” I asked. She nodded. Our ears began searching for the source of the noise.

“I think… I think it’s coming from the Gorge.” She said. We both walked up to the edge to get a look. Sure enough there was… something in the Gorge.

“What the hell am I looking at?” I asked no one in particular. It was the strangest thing. It was almost like the gorge was… flowing. It started in the distance but it soon got very close. No the gorge wasn’t flowing, it was filled with something. Somethings to be precise. There were thousands of them… they were flying along the bottom of the gorge. Little grey specks on a grey background. A literal river of… whatever the hell they were. “Geez, look at them all.”

“Is that…? Oh hell.” Carrot Top groaned. For the second time that day I followed Carrot Top’s gaze only to find Derpy. She was at the very front of the flock of somethings.

“DERPY!” I called out to her. I wasn’t sure if she was okay, but she didn’t appear injured or anything. Her course suddenly changed and she made a beeline right for the two of us. The flock followed suit and that odd flapping noise got louder and louder.

“Guilty! They won’t stop chasing me!” She yelled. I tried to get a better look at what exactly ‘they’ were.

They were manta rays. Little horn doodads and all. They looked exactly like any picture of a manta ray I’d ever seen, except they were gliding through the air. They were pretty cool looking too. The just sort of glided along; they didn’t flap or anything. I took several moments to appreciate how fascinating they were, until I realized that they were about to get a lot closer.

Derpy whizzed past us followed by a literal wave of flying fishes, each one at least the size of a pony, some bigger than two. None of them hit us mind you, each one deftly dodged both Carrot Top and myself. It was surreal. Like being in the middle of an aquarium… err aviary. I’m not sure where those things belonged, quite frankly. Giant grey flippers whizzed past us on all sides.

We were hit by a wall of that strange rustling noise. The sound of unflapping wings surrounded us. Once the wave passed and the din of the flippers died down we caught sight of Derpy making wide circles overhead. “Guys what do I do!?”

“Just land!” I offered. It made sense to me. They didn’t exactly look like there were chasing her. Just… following.

“Nuh-uh, They’ll eat me!” She called back.

Carrot Top facehoofed. “Derpy, they don’t even have teeth!”

Derpy threw a glance back at the pursuing mob gaping toothless mouths.

“Maybe they’ll just swallow me whole!” Poor Derpy, she sounded so scared.

“Derpy! If they were hungry, they would’ve eaten us!” I reasoned.

“...That’s true.” That seemed to satisfy her. “Okay I’m gonna land! Get Ready!”

Carrot Top tried to call out. “No, don’t do it here Der-”

Derpy landed smack dab between the two of us. The trailing school veered upwards just in time to avoid colliding with us. For several seconds we were eclipsed by thousands of fins each ray steered itself back into the gorge. Once the chaos subsided we watched the tail end of the school settle into the bottom of the gorge, disappearing against the canyon floor. Camouflaged.

Panting, Derpy spoke. “What the hay…*huff*… were those things?”

“I dunno. We should ask Twilight.” Carrot Top said.

“Good idea. *huff*... Just lemme, catch…. *huff*… my breath and we’ll… *huff*… go.”

“You Okay Derpy?” I asked.

“Oh I’m good…*huff*… you?”

I chuckled. “I’m just fine Derpy… c’mon… let’s get you home.”

The three of us headed back. Derpy recounted us with the story of how she found herself being chased by a legion of hovering sea-life. Apparently, while flying through the canyon a bit she decided to take a break on the canyon floor. When she touched down, she noticed that the floor was a lot softer than it should be. Then she noticed that the floor was dotted with thousands of little eyes. After that she decided to speed off… and the entire canyon floor decided to follow her.

Wacky stuff.

Well anyways Once we made it back to town we all headed off on our own path. I didn’t say another word to Carrot Top on the way back. That mare is just dead set on not liking me. Either way… it felt good to at least try and reach out. It’s something I guess.

Once I got home I unpacked and threw away the granola bar wrappers I’d saved. (Littering is a crime.) I cleaned out my Tupperware and threw away leftover sandwiches. I also began prep for an early client tomorrow. I dusted off my riding crop and hoof cuffs. I have to be a dominator tomorrow.

Also I’m going to start that letter to Crook. All of Derpy and Carrot Top’s Stories have me missing him. It’ll be nice to write him a letter.

Basics

Chapter 8

Basics

Dear Journal,

Today proved to be very refreshing. After all the drama that’s been floating through my bedroom and my life, it was very nice to have session with a client go swimmingly. Also it was nice talking with a mare from my hometown.

This morning however was well… less than spectacular.

When I got up this morning I checked my ledger. I only had one session and it wasn’t until late in the evening, so I decided to run an errand I’d been putting off. I had been meaning to stop by the library and grab a book about zebra culture. I was curious about it, but admittedly I was just hoping to find some way to get Zecora to pay me a visit. I would just love to get that sexy zebra into all sorts of compromising positions.

However if that was going to happen, I would need a better understanding of her culture. Quite frankly, considering how much I enjoy the company of Zebras, it seemed like something I should have done ages ago anyways. So, I took a quick walk down to the library after lunch. Incidentally, since I’ve started hiking, the trip to town has become rather pleasant. Not only does it feel like a much shorter walk, but I have a newfound appreciation for the walk itself. The town itself isn’t necessarily more enjoyable, but hey, you can’t have it all.

I’ve always found the library to be quite a fascinating building. I mean, it’s a tree. I’m not kidding. The building itself is a living, growing tree with doors and windows and balconies. It’s kind of trippy. I wonder if it’s magic. It must be, otherwise a hollowed out tree would die, right?

Well whatever the case, once I got near the front door I could hear shouting. There were two voices. One was a mare… an uncannily familiar mare. The other was a stallion, and a rather livid one at that. I couldn’t make out what they were saying, but they were definitely arguing about something.

When I actually got to the front door I wasn’t sure if I should knock. I reasoned that if anyone was screaming in a library and wasn’t being shushed by the librarian, it was probably the librarian doing the yelling. Surely that meant it was a bad time to visit. I should have just walked away right then, but against my better judgment, I hazarded a knock. I mean normally I’d just walk into a library, but this place as pretty small… maybe the rules were different. The yelling didn’t stop, but the door still opened.

Now, one fact I was not aware of was that there was a dragon living in Ponyville. Now had I been prepared for the possibility of encountering said dragon, I probably would have had a more eloquent response ready for such an event. “Holy shit, a dragon.” I didn’t shout it or anything; it just sort of... slipped out. What can I say, I was surprised. I wasn’t expecting two and a half feet of purple scales to answer the door.

He brought a hoof… claw over his mouth and gasped. “You said a bad word.”

I blanched. ‘Oh, fuck, he’s just a kid.’ I’m so bad with kids. I’m always worried I’ll blurt out something inappropriate. A fear that is not entirely unfounded given I’d just said ‘shit’ in front of one. That and I just don’t get kids. I’ve spent a lot of time examining the behavior of fully grown mares, but I just don’t know how to read kids. I never know what they want.

“*Ahem*… sorry.” I scratched the back of my head ashamedly. “Is… is now a good time?” The open door had added volumes to the heated argument in the background. It was definitely coming from the library.

The little dragon kid shrugged, having seemingly already forgotten my verbal faux pas. “Twilight and her boyfriend are fighting, but, it’s cool.” He motioned for me to enter. “I’m Spike, by the way.”

“Thanks, kid.” I responded absently. I vaguely remember him saying something about not being a kid, but I was otherwise occupied. ‘Twilight….Twilight… why do I know that name?’ Then it clicked. ‘The cute purple wordy girl! Hmmm… she never came back for another session.’

There was a loud masculine “CELESTIA DAMNIT!” from upstairs, followed by an equally loud and chastising “Spike is right down stairs!” Yup, that was Twilight’s voice. It was so angry I didn’t recognize it at first.

“Do they fight a lot?” I asked Spike.

He shrugged again. “Kinda.”

I wanted to pry a little more, but I decided not to: none of my business. I learned pretty early not to get involved in a client’s domestic disputes. One of several lessons I did not learn the hard way, mind you. I just had a front row seat to somepony else learning it the hard way.

Long Story.

Anyways, I decided to get what I had come for and then make myself scarce. No need to get caught up in anything. “So, kid, can you help me find something?”

“I told you, I’m not a kid!” he huffed.

‘Yes you are.’ I wanted to respond. When I was a kid, people called me ‘kid’ all the time. It didn’t bother me. Why was it so wrong to call a kid what he was… just a kid? Nothing wrong with being a kid.

“Sorry, kid, err… Spike. It’s Spike, right?”

He eyed me for a moment before nodding. “Yeah... and it’s no biggie. What can I help you find? We just re-shelved everything so I still remember where most of the books are.” He seemed proud of that fact.

I held back a snicker as the little reptile puffed out his chest proudly. “I’m looking for a book on zebra culture, do you have anything like that?”

He mulled over my question for a moment. “Yyyyyyyes… I think.”

“You think?” I deadpanned.

“I mean, I know we have something, but I don’t know if it’s really what you want. Right over here.” He led me over to a nearby shelf. He scanned it for a second before plucking a small rather faded looking tome. Life Among the Zebra by Great Venture. “Some guy wrote this after living with a zebra tribe for a year or something. Twilight says it’s kind of ‘racist,’ whatever that means. It helped her learn about this zebra we know named Zecora.”

Honestly it sounded perfect. I was about to thank the little guy before another burst of screaming came from upstairs.

“You are UN… BELIEVABLE!” the stallion shouted.

“Why is this such a big DEAL to you?!” Twilight half-yelled back.

Spike shook his head at their display. “I wish they wouldn’t fight in the library.”

“Yeah, they’re really going at it.” I noted.

“Yeah they are… which is... kind of a problem.” He sighed heavily. “This book is really old… Only the head librarian can check out the old books.”

“Which is Twilight, I take it.” ‘Fuck me.’

“You got it, pal.” He walked over to a large table in the middle of the library and placed the book gently on the table. “You can read it here if you want, but… well… kinda noisy, you know?”

“I’ve slept through worse,” I responded. “Thanks, kid.”

He glared at me.

“Thanks, Spike.”

He grinned. “No problem. Just let me know when you’re done.”

He started putting several books into the shelves while I read my little dusty book.

Twilight had been right, the book was very… I’m not going to say racist, just… judgemental. There were lots of “criticisms” of the Zebra society. I’m not sure who Great Venture was, but he seemed to take issue with every law and custom the zebra have. Regardless, the book was pretty informative. There were lots of neat little tidbits about tribal structure, cultural ceremonies, and all kinds of stuff. After about fifteen minutes, I’d found a passage that mentioned a Zebra that spoke only in Rhyme. I was about to continue reading when the fight I had been tuning out suddenly caught my attention.

“What do you mean you MASTURBATED in front of him?!” Roared the voice of the stallion.

I cannot remember a time in my life when I stood up faster. In fact, I rose so quickly that Spike took notice. “Is something wrong?” he asked, as he walked over to me.

If I had answered him right away he may have believed me. However, several seconds of stunned silence made my lie fairly transparent. “No, I’m fine, Spike.” He eyed me suspiciously. I was sweating bullets. After all, they weren’t just arguing. They were arguing about me! Before Spike had a chance to say anything else, I made a break for the door. “Geez, I really should get going. Bye, Spike. Nice meeting you.”

“W-what?”

“I have an appointment. Very urgent. I have to go. See you next time. Bye now.”

“Dude, wait!” I felt a tugging at my rear end and tripped forward on my hooves. He’d grabbed my tail, and I’d slipped. I climbed to my hooves and… I really glared at him. I… geez… I lost my temper… just a little bit.

“What the fuck, kid!?” I admit it, I shouted at him. I really shouldn’t have. It’s just that I… fuck… I dunno.

The worst part was how much it had scared him. The poor kid looked terrified. His eyes were wide, and he started to back away from me slowly. He started muttering something timidly. “I… y-you… the b-b-b-book.” He pointed a shaky claw to the yellow faded text tucked under my foreleg. In my haste I’d grabbed the tome about zebra culture.

‘Oh, fuck me. Kid was just doing his job. Son of a bitch. I feel like an ass now.’

“Sorry kid. I… I didn’t mean to yell.” I passed him the book. “Uh… here… here ya go.”

He quickly snatched up the book and held it to his chest. “I… I gotta go shelve this… um… you… you can go now… and sorry…. sorry I grabbed your tail.” He was about to cry. I may not be able to read kids that well, and he may not have even been looking at me, but even I could figure that out.

I was gonna try and… I dunno… apologize again, I suppose... but, just as I was about to, I noticed something. It was quiet. It was quiet. The fighting had stopped. ‘Oh fuck,' I quickly realized. 'They must’ve heard me shout.’

Time kind of slowed down on me. Part of me wanted to stay and explain myself, and make sure I didn’t damage my barely existent escort-client relationship with Twilight. The other, larger, part of me was singing a different tune. ‘Get the FUCK out of here, Guilty! This is going to be a clusterfuck! Between Twilight’s boyfriend and shouting at Spike, this can only go really South really quick.’

Needless to say, survival instinct won out over common decency. I returned to my home in a brisk jog. The whole way back I was cursing myself. I knew this was going to come back to bite me in the ass. I’d basically run away from a crying little kid. Okay, maybe he wasn’t actually crying, but still. I was already running through several apology scenarios in my head.

The fact that I had only just found a passage that might have told me about Zecora was just insult to injury. Two more minutes and I might’ve had what I needed. Odds were if I hadn’t screamed Twilight and her boyfriend wouldn’t have come down soon, anyways.

Fuck… I fucked up. I shouldn’t have tried to rush out of there. I shouldn’t have yelled at the kid. I shouldn’t have bolted after I did.

Fuck.

‘Oh well… I’ on my way home anyways. No harm in setting up early.’

I had a new client today. According to her letter, she was from Manehattan, which was good. It’s always nice to know you have some common ground before going into a session, and I could talk about Manehattan for hours. Since my act was all set, and I had an hour or two to blow, I did a thorough cleaning of my foyer and bedroom. Dusted off my candles and knick knacks. Made sure all of my chests were organized properly. Made the bed (twice.) Cleaned out the kitchen. Reorganized my liquor cabinet. Mopped the floors. Did all my laundry. Alphabetized my bookshelf…

Okay so maybe I was just looking for anything to keep my mind off of my colossal fuck-up.

Okay Maybe colossal is a bit harsh.

Huge fuck-up. Yeah, that sounds right.

So I was washing my teacups… again… when the knock came. It was your average, timid first-timers knock. A bit more confident than most, actually. I quickly set down my teacup and dishrag and hurried over to the front door.

‘Roguish grin, check. Hair, Perfect. House, utterly pristine. Good to go.’

I opened my door, and the session began.

She was blushing. Clearly embarrassed, but not… wilting.

“Guilty Pleasure?” Came a careful voice.

I nodded. “Hi, you must be Plume.”

She smiled, and nodded. She was a cute little thing. A unicorn. Brown coat, and a rather darling blue bob-cut. Her cutie-mark was a quill. She was wearing a scarf, and with good cause, the weather had been getting fairly chilly. I think snow is scheduled soon.

“Well, come in, come in… it’s freezing outside.”

“Thanks.” She stepped inside and hung up her scarf. “It took a little while to track you down, you know?” She laughed nervously.

“Oh?” I asked. She was trying to break the ice, but she was still nervous. This was looking to be a good session already.

“Yeah… I have a customer. She told me that she used to be a regular when you worked in that stable on twelfth.”

I slowly guided her to table in my foyer. And we took our seats. “And when I wasn’t there anymore you did some digging?” I guessed.

“Pretty much. No one really knew where you went. Eventually I got in touch with the Madame; she gave me your address.”

I didn’t really want to think about her. I quickly changed the subject. “I’m going to put a kettle on, do you have a preference?” I asked.

“Umm… jasmine?”

“No problem.” I trotted to the stove.

“So, you came all the way out here to visit little ol’ me?” I called from the kitchen.

“Actually at first, I wasn’t going to bother, but there’s a book fair in Tall Tale in a few days. Ponyville wasn’t that far out of my way, so I figured… ‘what the heck?’ you know?”

“Well I’m certainly glad you made your way out here.” I returned from the kitchen. “One thing we must discuss is of course… *ahem*… the matter of payment.”

“Oh, uh, yeah.” She produced a small purse. “Fifteen bits an hour, right?”

I smiled warmly. It helps break bad news. “Actually it’s twenty, now.” Fake nervous chuckle. “I’m independent.”

“…oh… well I brought sixty, hehe. I, uh… I thought that was gonna get me four hours.” She looked a little disappointed. Honestly I wouldn’t have minded throwing her a free hour, but… price is price. You never ever ever make exceptions for price; that’s the first rule of the business.

“Well, I hate to disappoint. But don’t worry… three hours will be…” husky bedroom voice “…plenty of time.” I circled slowly behind her as I made my way into the seat across from her. That’s a classic move, by the way. The stallion who taught me that used to call it “the predator.”

She was trying to contain her excitement. She smiled goofily for just a second, she shifted slightly in her seat. She seemed ready to start right away.

Which was exactly why I was going to take my time.

“So tell me. How’s Manehattan? I haven’t been back home in a couple years now.”

“Huh? Oh. You know Manehattan, it never changes.”

“Yeah?” I was trying to make small talk, but honestly I wanted to know about my hometown, too. “Last year was an election year, right? Do we have a new mayor?”

“I wish… I swear, Blossom’s gonna croak before she retires.” She joked.

“Don’t I know it.” I laughed, politely. “So tell me a little about yourself.”

“Oh… uh… not much to tell, really. I’m a writer. I own a little bookstore on maple.”

“Oh yeah? That’s fun. What do you write?”

“Oh, you know… a bit o’ this, a bit o’ that. I take commissions.”

“Cool. Anything I might have read?”

“Uh… probably not… ever heard of Just Like Honey?”

I had not. I shook my head.

She looked... disappointed. She was hoping that I had, clearly.

“That was my most popular work. It did… okay.” ‘Tough subject. Change the topic, quick.’

“Well, don’t worry. You’ll get your moment.” Reassuring smile. “So tell me-” The kettle whistled “Let me get that.” I tended the kettle. So far the session was going splendidly. She was eager, yet apprehensive. Not stuck behind a veil of shyness, not looking to fulfill some particular fetish, it seemed. She was just a mare looking for a good time. In a way it was sort of refreshing; she was just the sort of client I was used to. In more ways than one she was… a little piece of Manehattan.

I returned with jasmine tea. “Here you are.” I placed a teacup gingerly in front of her. “I hope it’s to your liking.”

A blue shroud of magic grasped the cup and brought it to her lips. She smiled. “It’s really good.”

“Well, thank you, I do try.” I sat down, and took my own sip. It was good. “So tell me, Plume, what’s it like running a bookstore? That has to be fun.” ‘Hopefully this’ll prove a cheerier subject.’

Plume shrugged. “Oh, you know. People come in, chat, I ring them up. It’s all pretty straight forward.”

“Oh, come on. That’s gotta be fun. Opening up in the morning, chatting up customers, taking home a nice stack of bits in the evening, that sounds pretty nice.” Classic small talk: compliment what the person does, display a small amount of jealousy, it makes a pony feel good, and that’s what I’m all about.

“I guess it is kinda nice.” She smiled. “What about you? You must love your job. I mean you’re… you know.”

I suppose I do love my job. Sure I’ve got good day and bad days, but ultimately my job is to make ponies happy. What’s not to love about that?

“Yeah… I like what I do. Especially now. It’s nice being your own boss.”

“Hehe, I know the feeling.” We had a little moment after that. We were just sort of looking at each other, each with a smile on our face. It wasn’t too long before she blushed and suddenly found her tea to be very interesting. She didn’t stop smiling though.

Time for my favorite question. “So tell me, Plume. What can I do for you?” My hoof twirled from myself to my client.

Her blush deepened. “Oh, geez.” Another nervous laugh. “You sure know how to ask ‘em don’t you?”

“What? It’s a simple question. We can’t really have any fun, if I don’t know what you want, now can we?” I teased.

“Oh come on, Guilty.” She had a sort of frank look on her face. She appreciated my little game, but didn’t really feel like playing. She had other things on her mind. “You know what I want.”

“I suppose I do, don’t I?” I placed my tea on the table and stood up. “Follow me.” Off to the bedroom we went. “Two rules…” I began as we stepped into the bedroom. “… no kissing on the lips...”

“No problem.” She responded. Honestly that’s very rarely a problem for ponies.

I walked over to my potion trunk and grabbed a Blue phial from within. “…and if either one of us says stop, we both stop.” I downed the dreadful brew.

“Of course.”

“Fantastic.” I slid off my jeans. “Shall we?”

She blushed and nodded.

After that there were no words. She slid onto the bed onto her back. She spread her legs wide. I climbed on top of her. She was breathing heavily. So eager. I rubbed myself against her entrance. She gasped in pleasure. She was soaking. I could’ve slid in right then, but I wanted to tease her.

I poked and prodded at her entrance. She squirmed in pleasure, gyrating her hips, pressing herself onto my flesh. Each time she tried to get me inside of her I pulled away teasingly. It wasn’t until she was practically begging for it that I let her have me.

I’ve had a hundred clients like this. This was the kind of mare that was right in my comfort zone. She was pleasure-hungry, not totally ashamed, and a bit submissive. It really let me stretch my escort muscles.

Literal and figurative.

The sex itself was very enjoyable. I love a mare who’s… vocal about climax. Her eyes would roll back in her head. Her back would arch. She’d scream in pleasure. Clearly she was a mare who hadn’t had that kind of pleasure before.

Not a virgin, though. That much was obvious. She was just… inexperienced.

I helped rectify that.

Again there were no words, just… thrusting and grunting and screaming and moaning and twitching and quivering and spreading and plunging and panting and sweating and humping and fucking.

After several position swaps and many climaxes, I ended up behind her. She liked that the best, clearly. Each breath was labored (in a good way.) As I gave her pleasure and nibbled and teased at her neck and back. She liked that too. Every few minutes she’d have a brief cluster of orgasms, and after some more fucking she’d start all over again.

Eventually, I felt myself near my limit. “Where do you want it?” The first real words spoken between us in quite some time.

“Not yet! *huff* Oh please don’t stop! *huff* I’m so close!” I managed to hold out for a few more minutes. It paid off. As I neared my own rapidly approaching climax, I felt her ride her biggest pleasure wave yet. Her back arched and her walls clenched tight. Her eyes rolled back and her tongue lolled out of her gaping mouth, which was stuck in a silent scream. She literally quaked with climax. So hard, in fact that she fell off of my now squirting stallionhood. My seed spilled all over her coat as she collapsed onto the sheeted cloud beneath her. She barely seemed to notice.

“That… *huff*… you… *huff*… I… *huff*… I have… *huff*… no words…” She writhed about on the sheets, soaking them in sweat. Her coat was matted in jism, giving her a rather “calico” look, and her mane was a frazzled mess of blue.

“Looks like somepony enjoyed themselves.” I traced a hoof across the quill on her rump, evoking a yelp.

“Hehehe… yeah… hehehe.”

‘Oh, good, I’ve fucked her silly.’

“You ready for some more fun?” Odds were she was gonna be sore for a while. So I decided I’d do something nice and relaxing for her.

“I dunno… I’m… pretty sensitive right now… hehehe!” She wriggled her way onto her back and grinned up at me. “What did you have in mind?”

I licked my lips. “Just lie back.” I gently spread her legs apart. She was still red and dripping wet. I dove in.

“What are you- OH!” Her voice fluttered in pleasure as I began to… polish her pearl. “Oh… oh my.” For mares and stallions alike, post-coital head feels amazing. The taste of recently plowed mare is something too. “Oh… oh geez… a-again?” she asked as I brought her to yet another orgasm. Her hind legs locked around my head as I licked up all of her lovely juices.

She tasted heavenly.

After several more climaxes she was spent, and I decided to lie down beside her. I was exhausted. It was a good exhaustion though, the kind of exhaustion that reeks of a job well done.

“So… *huff*… how do we feel?”

“Oh you know… ecstatic. I mean like… drowning in ecstasy… that kind of ecstatic.” She turned to face me. She had rather beautiful eyes. Pale green, like key lime pie. “I’ve… I’ve never had anypony… do that for me before, ya know?”

“No?... *huff*… Well what did you… *huff*… think?”

“It was… fantaaaastic.” The word melted out of her mouth. “Should I, uh… return the favor?” there was that nervous chuckle again.

“Only if you want to.” I responded. I wasn’t quite hard again yet, but I could change that easily enough if I needed to.

I got the feeling that if she could blush any more she would have. “I… I do… want to, that is.” she managed.

“No problem. Give me a few minutes to… reload, if you’ll forgive the metaphor.”

“O-okay.” She grinned. We cuddled for a bit while my flesh renewed itself. She relished the physical contact. She was very happy to be held. I got the feeling it had been a while since she’d been intimate with anypony. We stayed embracing until I felt myself prodding her again.

“I’m ready if you are.” I said to the mare who had her face buried in my chest.

“Okay.” She said softly… excitedly. The two of us rolled around until she was “face to face” with my erect member. She looked… unsure.

“Is something the matter?” I asked.

“Huh? Oh… no, s’fine” She parted her lips and took me into her mouth. The warmth of her flesh, and the soft supple texture of her tongue caressed me. Unfortunately there was only one thing I was really paying attention to.

“Teeth”

“hhhhmmm?” she… inquired through a mouthful of stallion.

“Teeth, Plume, watch the teeth.”

“mmmhhhhmmmm.” She proceed to bob her head up and down on me. It felt rather nice… until her mouth began to close.

“*ahem* teeth, Plume… that hurts.”

“hhhorrmmm” she apologized. She started up again after opening her mouth to its widest. After that it felt good again, but before too long, I found myself getting… sanded again.

“Okay stop… stop.” I hate putting a halt to a client’s fun, but I wasn’t about to sit there getting my cock scraped off.

Plume pulled her lips off me with a wet pop. “Sorry sorry sorry.” She looked fairly distraught.

“It’s okay. It’s okay. Geez… that smarts.”

“Sorry.” Her head fell.

“It’s no problem, I’m okay.” I reassured her.

“I’m not too great at that, huh?” She sighed heavily.

“Well hey now, don’t get all… dejected.”

“I’m not dejected. Just… bit off more than I could chew I guess.” She said wistfully.

“You… may want to phrase that differently.” I joked. She snickered at that. “Tell me, have you ever given head before?”

She shook her head. “I hope it wasn’t too obvious.”

“It… kind really was.” I couldn’t help but chuckle.

“Yeah, well… only one way to learn, right?” She joked.

Idea.

“Well, I am a staunch believer hitting the ground running… but that doesn’t mean you can’t… start off in the kiddie pool.”

“You’re getting your metaphors crossed.” She laughed at me. That was a good sign; it meant she wasn’t too depressed to hear me out.

I rolled my eyes. “Ha ha. My point is… well why don’t I just show you.” I walked over to one of my many trunks. “What’s a good size?” I asked myself aloud.

“What’s a good size for what?” She asked, half-worried.

“For practice.” I answered. I decided on a medium-size silver vibrator. “I don’t have to explain what this is, do I?” I asked, trotting back to the bed.

Her blush returned in full. “N-no, I… I know what that is.”

“Well, here.” I hoofed the toy to her, and her magic took it from me. “Why don’t you practice on that.”

“Uh… okay, I don’t see why not.” She started to open her mouth, when I stopped her.

“Hold on… turn it on first.” I instructed.

Her brow furrowed. “That seems… a little weird.”

“Trust me.”

She obliged, and the toy’s little magical motor sprang to life. The then proceeded to hover the slender toy into her mouth. Soon after she began to fellate the fake stallion, a rattling sounded from within her head. She quickly popped the dildo out of her mouth. “Ow! Damn!”

I chuckled. “See this way, if your teeth touch the surface… you know it.”

“Yeah, I’ll say.” She rubbed her jaw slowly. “You coulda warned me, you know?”

“Only one way to learn.” I teased.

She threw me a look, which quickly melted. Ultimately she decided to take my advice. For several minutes she practiced. Every so often I’d hear a rattling inside her mouth, and she’d wince in pain. I’d offer small bits of advice: what to do with her tongue, how her lips should be puckered, remind her not to take it deeper than she could stand. Just some basic stuff.

Eventually she got kind of a handle on it. She managed to keep it up for a while without rattling her brain.

“Not bad at all, Plume. Looks like you’re getting the hang of it.” I gave her a literal pat on the back.

She smiled timidly up at me. “Thanks.” Her brow then furrowed. “How do you know so much about this?”

“What, fellatio?”

“Yeah I mean, you’ve never… have you?” Her implication was clear.

“What? Sucked a guy off?”

She nodded.

“Oh sure, lots of times. That vibrator trick is actually how I learned to keep my teeth off the pole.” I said.

“You’ve… been with stallions?” She didn’t seem put off by it, just... curious.

“Yeah, I have… I used to have a few male clients.”

“I… I guess I never realized, you know? That you were like… bisexual.”

I scoffed. “I’m not bi, sweety. I’m a hundred percent hetero. Couldn’t you tell?” I was just trying to be funny, but something was… troubling her.

She looked at me... baffled. “But wait… then why have you…?” She trailed off, but it was obvious what she was asking.

“Well… that’s the job. Or…was the job… I don’t really take stallions as clients anymore.”

She looked… disgusted isn’t the word… shocked maybe. “How… how do you make yourself do that?” she asked.

I paused for a moment. I didn’t know how to answer that. Back in the stable, you went to bed with whoever liked you: stallion, mare, zebra, griffin, whatever. Sure, I never took any particular pleasure from being with stallions but... that never stopped me. Actually, back then nothing stopped me. I’d do anything anypony asked, no matter who ‘anypony’ was. I was sort of… devoted to the job, I guess.

“I… I dunno… It was just… what everypony did. I knew gay guys who would take mares… I knew straight girls who would too. It’s just… you take who wants you. It’s no big deal really. You grit your teeth and… do what you do best.”

She shook her head. “I dunno… I don’t think I could ever just… make myself be with another mare.”

I shrugged my shoulders. “Meh… it’s not so bad. As long as you think of it as work it doesn’t…” ‘hurt that bad.’ “… bother you that much.” I smiled a big fake smile.

‘Where did that come from?’

“I guess. You know, you’re kind of weird, Guilty.” She rolled onto her back, lazily floating the vibrator above her.

“Oh yeah, how so?” Honestly, my mind was elsewhere. Where had that thought come from? That silly little rogue thought? Being with stallions never… hurt. Well I mean, the first few times I… received, I was a bit sore but… It never felt… wrong, or anything.

Did it?

I swear it’s that weird mood I’ve been in rearing its ugly head again. Whatever the case, I didn’t have the time right then to properly contemplate.

“Well it’s just… you’re like… the polar opposite of what I like in a stallion.”

“Harsh,” I deadpanned.

She shook her head. “No, not like that… I mean like… okay hear me out. I like big tough guys who… who like to hide their emotions, ‘cause... they’re big tough guys. But then, once you get to know ‘em it turns out they’re just big softies.” She was very happy with her little explanation. She definitely had someone in mind.

“But you, you’re… so gentle… so very caring and kind. But… it’s like… there’s secretly a tough little pony in there.” she stated.

I forced a chuckle. “I’m… not sure if that’s meant to be a compliment or…”

“I… sorry… I didn’t mean anything by it…” She held up her hooves defensively. “It was just an observation.”

“Right… hey, no worries.” It kind of bothered me, but my act kept that from her. “So… do you wanna give it another go?”

Her brow furrowed. “Give what another go?”

I indicated my member.

“Oh… is… is it okay?”

“Only one way to find out.” I grinned seductively.

So she sucked me off. That little bit or practice did wonders; it was very pleasurable. Things sort of wound down after that. She complained about the flavor of semen. We took a shower. We chatted more about Manehattan. I made more tea. She told about this boy she had her eye on. I encouraged her to make a move. She said goodbye, and that she might see me on her way back. I bid her adieu, and wished her well.

Which left me plenty of time to think.

I’d never really given it too much thought, my time with stallions. Sure, I took more than a few male clients, but… I never really cared for them. I mean they were really nice guys for the most part, but… I dunno. I was never really… present for sex. It was just sort of… going through the motions.

It didn’t hurt though. I never felt… dirty… I mean, no more than normal for the time.

Shit.

My head’s all fucked up right now.

I did notice something, though, something about my behavior. When I got out of the stable I promised myself no more stallions. I never... never really thought anything of it, but it’s very telling. I think I just realized that I did that back then,
because I don’t like having sex with other stallions. Like… actively dislike it.

Back before I went independent, the job was the job… but now? I decide what the job is. I pick what jobs I do and don’t take. I’m in charge of me. And some small part of me decided that that meant no more stallions.

But at the same time, there’s tons of shit I do that I don’t like. I whip mares. I get whipped by mares. Hot wax play. Pegging. Felching. Being tied up. Rim-jobs.

The list goes on.

What about being with stallions made me say ‘no?’ Why am I willing to put up with all manner of unsavory act, but won’t so much as take a stallion as a client?

I... I honestly don’t have an answer. Maybe I just enjoy the company of mares more than stallions. I’m not talking about sexually; I mean in general. Derpy and Pinkie are my only real ‘friends’ in Ponyville. When I go to a market, I usually stop by the stalls with girls at the register. I mostly got along with the girls more than the boys when I worked in the stable.

I... I honestly don’t know what to think right now.

I’ll... figure this out eventually.

Ah fuck, I just remembered what happened with Spike.

More stress.

Hooray.

*sigh*

Well either way... I had a nice time tonight.

I’ll sleep well; I’m pretty tuckered.

Author's Note

Thanks to everyone for reading. A special thanks to my big fan Black_Skulls, Creator of today's OC client.

Threesomes

Chapter 9

Threesomes

Dear Journal,

It snowed today. Snow out in the city is different than here. It’s always getting trampled underhoof... turned into slush by carriages and pedestrians. You never really see really fluffy snow, unless you’re on a roof. Here especially, since I’m so far out of the way, it’s totally undisturbed. Just a big field of virgin white.

It’s rather beautiful.

My first Winter out here I got so excited that I made snow-ponies, something I’d never done. They turned out kind of crap, but I had fun. I also learned that I actually had to shovel snow. Shoveling snow was markedly less fun. Fortunately, it was only a couple of inches deep this morning, so I didn’t have to worry about that just yet.

Ever since that Plume girl, I’ve been thinking about... well… stallions. Specifically I’ve been trying to figure out…I dunno… how I felt about being with them. When I think on it, I genuinely don’t think it ever bothered me. I’m having trouble accepting that though, because there are a lot of things that I don’t think used to bother me, but maybe they did.

Life in the stable was… chaotic. I mean… I imagine in most professions you clock in, go to work, go home, have dinner, hang out with friends or whatever, and then go to sleep. As an escort, you work when you work. Sometimes you’ve got a few days between appointments, sometimes you have ten minutes. Sometimes you work all night, sometimes you spend all day trying to pull in a customer to no avail.

I guess that lifestyle kind of puts you into a certain mindset. Work is work, and you take what you can get.

Maybe that’s the only reason I used to take male clients. Maybe it did bother me, but I didn’t let it because… you know… it was bits in my pocket.

I don’t know what to think right now.

Whatever the case, I had an appointment this morning.

I need to clarify: I went to the spa.

As it so happens I had an appointment with two mares this evening. Not with Aloe and Lotus, unfortunately. I’m still waiting for the two of them to come back to my bedroom. But, I decided it would be a good idea to have their masseuse work out all my knots before I potentially got tag-teamed.

I marched into town through the ice and snow. I think I may need to invest is a pair of snowshoes, the snow is supposed to get pretty deep this year, and I can’t exactly shovel the entire path to town, now can I? Either way, the walk into town was beautiful, if fairly exhausting.

The winter has its advantages when it comes to being inconspicuous. Ponies tend to stay indoors, so there are fewer gawkers. A lot of ponies wear pants when it gets cold, so I don’t stand out as much. Also, I can wear a big heavy coat with a hood that covers most of my face.

So I made my way to the spa. Once there, I was greeted with a nice wave of warmth. They were really cranking the heat; It felt almost oven-like. A smiling pink pony greeted to me from behind the counter. “‘Ello again, Meester Guilty.”

“Hi there…” ‘Shit. Is that Aloe or Lotus?’ “… you.” I blushed when I couldn’t remember which was which. I attempted to mask my embarrassment my hanging my coat up on the wall. I don’t think she noticed, honestly. “Is, uh… *ahem*… is Quake ready for me?”

“Not yet, Meester Guilty. I weell let you know.”

“Thank you.” I said. With nothing else to do,I grabbed a magazine and took a seat in their little reception area. Of course, all they had were those ridiculous celebrity gossip rags, which I’ve never really cared about. But hey, anything to pass the time, right?

Not long after I started reading about some nonsensical scandal involving some drug-addled actress, the door chimed. “Oh, meess Rarity, meess Flootershy. So good to see you again.” My ears perked up at the mention of Rarity. I peeked over the edge of my gossip rag. Sure enough Rarity had just stepped in to the Spa, along with some butter-yellow pegasus companion.

“Aloe, darling, it’s a pleasure to see you too. Fluttershy and I will have the usual.”

‘Oh hey, she said Aloe! Okay, so pink is Aloe. I should commit that to memory. Pink is Aloe. Pink is Aloe. Pink is Aloe...’

“Pardon me. Sir?”

‘…Pink is Aloe. Pink is… wait, what?’

Apparently as I sat there, trying to memorize a name, Rarity had been trying to get my attention from behind my little barrier.

“Terribly sorry, but would you mind letting me read that magazine. I’m afraid I’ve read all of the other ones. I come here a lot you see, so if you wouldn’t mind-”

“Here.” I did my best not to look at her. I was sure she wouldn’t want a surprise like running into me right that second.

“Oh, thank you so much, dear. I… oh.” She stopped dead. I only caught a glimpse her face. She looked mortified.

‘Shit… she saw me.’

Her little yellow friend took notice of her sudden silence. “Rarity is everything okay?” Her voice came little more than a whisper. She sounded fragile… dainty. “Oh, I’m so sorry. Is this your friend? I’m interrupting aren’t I?” She began to back away.

Rarity snapped out of her trance. “Fluttershy, dear, everything is fine. You’re not interrupting anything.”

“Oh, sorry. I just assumed… you were acting like you knew him. I must have been mistaken.”

“I-I’m afraid not, Fluttershy, dear.” Rarity shot me an apologetic glance. “W-we’ve only just met.”

I don’t mind that she lied. I mean I know she's sent a few clients my way, but she has a certain image to maintain, especially in front of her friends. I know that there's a difference between telling somepony something in confidence, and telling the whole town, especially considering the fact that I think one of her friends is Applejack. If it got out that she was seeing me... I don't even want to think about it.

Honestly, it doesn't bother me.

“Meester Guilty, Quake will see you now.” Aloe called from the counter.

“Welp, that’s me.” I hoofed the magazine over to Rarity as I stood up. “All yours. Nice meeting you two.” I smiled at the pair. Rarity managed a nod and a fake smile, and her friend just blushed. I gave them a quick goodbye and made my way to the masseuse’s room.

It’s a nice little room. A few shelves lined with sheets, a couple little desks covered in balms and creams and oils, and of course, there was a large cushioned table in the middle on the room, its surface made smooth from rubdown upon rubdown. In many ways it was similar to the bedroom in my cottage.

Quake was rubbing her hooves together and cracking her neck when I stepped in. She’s a big girl, not exactly muscle-bound just… thick… and large. She stands easily a full head above me. She's got a pale tan coat, a shoulder-length blonde mane. She’s actually quite attractive in a warrior princess sort of way.

She turned around as I stepped in. She had a look of pure business. “Pants off. Lie on table.”

I love the way she speaks; it’s very… direct. Her accent is also pretty interesting. I think she’s from the Frozen North.

I started wriggling out of my jeans. “How’s it going, Quake?”

She scoffed. “Same. Business good.”

“Yeah, for me too. What’s that stuff?” I pointed to her hooves, which were still vigorously coating themselves in some sort of lotion.

“Is new. Haysian. Called ‘tiger balm.’ Good for muscles.”

“Smells strong.” I noted as I climbed up onto the massage table.

“Yes.” She stated simply.

I laid myself down flat, and stuck my face through the… I don’t know what you call it. The face-hole-thing at the end of the massage bed. “You know, I’ve got this knot in my lower back that really… ooooooooooooh.” Bliss. Her heavy hooves quite suddenly began kneading away at my flesh.

“Relax. I fix.”

“Ooooooooooooh.” I felt so good in that moment when she first laid hooves on me. “Quake, marry me.” I was melting; the words just sort of dripped out my mouth. Massages really are something else. When you've got a masseuse or a masseur who really know what they're doing, there's nothing better.

“Heh. My husband will not be so short.” Her hooves worked deep and slow. The balm on her hooves began to heat up. It was a sort of... it's really hard to decribe... it was like a cold burn. She worked it deep into my coat and into my skin. It loosened up all my muscles.

“I’m not sh- ooooooooooooooh.” I tried to protest, but I my capacity to form words was quickly becoming impaired. If my eyes were opened they probably would've crossed. She started working my neck and shoulders, expertly locating all of my stress points. I keep a lot of stress in my shoulders.

“Shorter than me.” She laughed.

I tried to giggle, but it came out sort of slowly. “He… he… he… so’s everypony in town.”

“Hmmmmm, not everypony…”

My response was delayed. It was becoming very hard for my brain to turn absrtact concepts and ideas into words. “Who-? Oh… right… Big Macintosh.” Big Mac is a nice guy. I think he’s Applejack’s brother, but he either doesn’t know or doesn’t care how his sister thinks of me. He sells me apples like he would anypony. He’s a quiet guy, and fairly enormous.

“Mmmmmm, Big Macintosh… he’s sexy, yes?” Her voice became somewhat wistful, and she sigh breathily.

‘Great, just what I don’t want to think about.’

“I suppose… objectively… he’s certainly… attractive.” I was trying and failing to block unwanted images from my mind.

“Yes… and big.” If I had seen her eyes, I’m sure they would have been full of stars.

“Mmmmhmmmmm,” I absently agreed. She continued to wring all the stress out of my back, with intense kneading and pressing and squeezing. Minutes passed. My eyes rolled back in my head and I went limp. I felt like a wet noodle. Well most of me did. That much time and physical contact with a woman… hell, it was bound to happen.

“Uncomfortable?” She asked

What she was saying only barely registered. “Hmm?... mmhmm.” came my best attempt at a reply.

“Flip.” She instructed.

After much work on my part I managed to get onto my back. It was only then that I noticed my situation. My stallionhood was at full attention. “Oh hey…*huff*... look at that." My breath was coming in pants. I was getting fatigued just getting rubbed down. I suppose that's a sign of a good masseuse.

“Excited to be alone with mare?” Quake joked as she began to massage my chest lightly.

I chuckled. “I uh… *huff*... I usually charge... *huff*... for the privilege.”

She seemed to think i was joking, and laughed a little. “Oh? How much you charge, Guilty?”

“Twenty...*huff*... For an hour” She grabbed one of my forelegs and her hooves ran firmly down the limp appendage. Whenever one of her hooves met mine, it quickly found its way to my joint, and began again. It was like she was scraping all of the wear and tear out of me.

Her brow furrowed. “You are serious?”

I nodded, wincing at the glorious pain of my massage.

I sound like an M, don't I? I swear, this mare does things to me.

“You are whore?” She asked. It wasn't really an accusation, she just seemed surprised.

I cleared my throat. “I prefer escort, but… yes.” She trotted around me, and began work on my other foreleg.

“Hmmm…” She briefly ran her gaze up and down my body. “Too small for whore, no?” She was literally sizing me up.

I laughed aloud at that. “Do you mean me or my…”

“Both.” She brushed my cock with the back of her hoof, eliciting a gasp from me. “Ponies pay so much for this?”

“That and more.” I would've used my sexy not-quite-baritone, if I could've.

“Hmmm…” Quake shrugged, and for several more minutes continued to massage my front, carefully avoiding touching my stallionhood. She worked her magic over both of my hind legs as well.

Truth be told, I came very close to climax. She never even touched my naughty bits. If the massage gig ever falls through, this mare may have a future as an excellent escort. There's always a market for big girls, especially forceful ones. There's no shortage of submissive stallions in the world.

And this mare has something of a gift for giving orders. “Okay. Flip again. I finish back.”

I struggled to lay face down again. Eventually Quake just spun me herself, and finished up her massage. As she continued to work the knots in my muscles and absolutely obliterate my stress, my erection slowly subsided.

She continued in silence, and save for a few blissful ‘mmms’ and ‘oooohs,’ so did I.

“Done.” She eventually said. “Feel good?”

What she had done for me really couldn't be put into words. Still I gave it my best shot. “Oooooooooooohhhhh yeeeeeeaaaaaaah.” I sounded like I had just come. I was weightless. My shoulders and hips and legs and everything felt amazing… amazing and sore. “Oh my Celestia, I feel like a ragdoll right now.” I honestly thought I would collapse if I tried to get up.

She laughed jovially. “You sound like mare.”

“It seems appropriate. You are the stallion in our relationship.”

“HA! I like you Guilty. You make me laugh.”

I stretched and shifted on the table. “Geez… this must be what it feels like… well, what it feels like to be with me.”

Quake laughed at that too. “Little pony sounds confident.”

“I’ll have you know, quite a few mares have had more trouble walking than this after I was done with them.” My mind immediately jumped to Derpy. I could remember quite a few times when she had to lie down after a good session.

“Hmph… maybe you make up for size with... something else.” She was trying to size me up again. Her mind, surely abuzz with several possible lascivious acts bewtween her and myself.

“Well… maybe you can find out for yourself sometime, hmm?” I joked lewdly.

She grinned at me. “Maybe sometime." Her voice was so husky. "For now… go to desk, pay sisters. I have appointments.”

“Until next time, Quake. And maybe ‘next time’ will be at my cottage?” I offered suggestively. I was really hammering the point home; I might've overdone it, looking back. Oh well, I don't think I hurt my chances too much.

“All right, enough. Go. I must get ready.” I may be mistaken but I swear she was blushing a tiny bit.

I didn’t bump into Rarity or her friend on the way out. I just paid Aloe for my massage, grabbed my coat and made my way home.

I kept trying to plan out a session with Quake in my head. What music to put on, what kind of food to make, how to actually go about fucking that mountain of a mare, that sort of thing. Never too early to be prepared.

However, try as I might-

This hurts to even write down.

Quake… kept turning into Big Macintosh.

I just can’t get stallions out of my head. I wish I knew why I was thinking so much about it. It’s really starting to fuck with me.

The bitch of it, is that I planned a fucking amazing session.

Light acoustic guitar on the gramophone, something badlandsy. A dinner of something classic, like a veggie loaf, with a side of beans and some homemade applesauce. Hard cider to drink. We’d retire to the bedroom. I’d-

Whoa there! That’s about enough of that! I’ve got a fucking threesome to write about!

So uh… yeah… anyways…

When I got home I shook the snow out of my jacket and hung it up to dry. I had about an hour to get ready, but, honestly, there wasn’t much to do. The bed was made, I’d just dusted, the shower had been scrubbed down last week, I’d organized all my chests not long ago. The place was pristine. I did need to start a fire, though. I also needed to clean myself up. I’d been walking around in the wind and snow; my mane was a mess. A quick shower and shave took care of my appearance, and I was ready to go.

So, I lounged by the fire are browsed through an outdoor living catalogue while I awaited my appointment.

Now that I think about it I think about there might be some snowshoes in that catalogue.

I should order those.

Anywho, a while later there was a knock, and I hopped up to answer it. I gave myself a quick glance-over, and finding not a hair out of place I put on a dashing smile and opened my cottage door..

The snow had stopped by now, but the wind had really picked up. My eyes began to squint as the cold dry air blasted my face. I could scarcely make out two huddled forms on my doormat.

“Wooo! Inside, ladies.” I ushered the shivering ponies into the warmth of my foyer. Closing the door was actually kind of hard; it was pretty fucking windy. They shuffled inside, tracking in trails of snow. Their teeth were chattering, and their knees were knocking together. “You alright? It’s freezing out there.”

One of the ponies spoke up from under a padded hood. “Brrrrrrrr. What is Rainbow Dash thinking?” Her voice was somewhat tomcoltish.

“She said something about pushing a blizzard away,” said the other, in a somewhat mature cadence. “This is just as bad, though.”

The first pony nodded in agreement.

It seemed like they’d scarcely noticed me. Something I’m not very used to when it comes to a client. Still, it’s easy enough to remedy.

“I can take your coats.” I offered with a smile.

The two turned to face me.

“Thanks” said the first pony. Her magic lifted the coats off of the pair, and placed them onto my outstretched hoof.

With their hoods off, I could actually get a good look at the two. The first was a unicorn; she had a lovely… I want to call it cyan… coat, and striped, somewhat feathered, mane and tail. Her cutie mark was a harp of some kind. Even shivering, she was hot.

See what I did there?

I promptly hung the fluffy jackets and led both ponies to my table, where they each took a seat.

“Can I get either of you some tea… or cocoa maybe? Something warm?”

“I’m good,” the unicorn happily responded. Her companion just shook her head. This one was an earth pony; she had a lovely beige coat, and a rather vibrant mane of blue and pink. Her cutie mark was little candies in wrappers. She seemed a bit twitchy, clearly nervous.

“Well I’m just going to put a kettle on, real quick. If you change your minds, let me know.” I walked to the kitchen and began preparing myself some hot water.

Okay, now with couples, a session is, of course, drastically more complicated. Not only do you have to figure out what each mare wants from yourself, but also what they want from each other. Understanding the dynamic of a couple is crucial to process. As such, I like to take a moment to...

Well I won’t say eavesdrop but...

No I will say it. I eavesdrop on them.

As I slowly filled my little steel kettle, I watched and listened.

“You okay, Bonny?” said the unicorn.

The earth pony whined a response. “Why did I agree to this?” I could see her cradle her head in her hooves.

The unicorn scooted closer to her. “Becaaaauuse you love me. And becaaaauuse you promised. And becaaaauuse you’re at least a little curious.” The earth pony just groaned, and her companion wrapped a comforting hoof around her. “We can still go home.”

In response the earth pony sunk into the half-embrace of her minty companion. “No… I promised.” The two nuzzled affectionately.

‘Okay, that’s enough spying, Guilty.’ I returned to my guests, my hoofsteps, causing the two to quickly scoot out of their hug.

“Sorry about that.” I took my seat. “Anyways, I have a few questions before we start... if you don’t mind.”

The unicorn just gestured for me to continue.

“What should I call you? You don’t have to tell me your names, but I have to call you something.”

The couple exchanged a quick glance. “I’m Lyra,” replied the minty mare. “and this is Bon Bon.”

“Nice to meet you, Lyra and Bon Bon. I’m Guilty Pleasure.” Hunky smile. “Second question: We of course must discuss the matter of…” Fake nervousness. “… payment.” Pretending to get awkward seemed to make Bon Bon open up a bit; she began to smile.

“Oh Derpy told us all about it. Twenty an hour, right?”

‘Clients from Derpy? Interesting.’

“That’s right, and two of you makes for forty an hour.” More fake nervousness.

“Yeah I figured. I’ve got… hang on.” Her magic hummed, and a pouch of bits floated of her coat on the wall. “I’ve got a hundred and forty, that’s enough for four hours, right?”

Bon Bon facehooved. “Lyra… sometimes I wonder about you.”

“What?” asked Lyra, oblivious.

I chuckled. “Sorry, but that’ll get you three hours… with twenty bits to spare.”

“Oh.” She just looked angrily at her pouch and clicked her tongue. “Damnit.”

Bon Bon snickered. “It’s okay, sweety. I’ll do aaaaall of your math for you.”

“Sh-shut up! I can do math!” Lyra insisted.

They were very cute together; their antics were positively precious. They also gave me an idea. Lyra already seemed to have no problem warming up to me, but Bon Bon was still a bit stiff. She also seemed to enjoy teasing Lyra, which would be a quick way to establish a rapport.

So I would gang up on Lyra with her.

It would be tricky. If I took it too far, I’d not only offend Lyra, but I’d be in hot water with Bon Bon for poking fun at her girlfriend. It would take a light touch. I decided to start small, by allowing myself to laugh at Lyra’s expense.

I have a fairly good fake laugh, but I didn’t need it for this. It was actually pretty funny.

So I chuckled at Lyra, which seemed to make Bon Bon happy.

Lyra on the other hand seemed unamused. “Oh, you guys are dicks.” She began to count her extra bits out of the pouch. Once all her bits were out she slid the pouch across the table, with a frown.

I gave the pouch an exaggerated skeptical glance. “You sure you got that right?” I jabbed.

“You know what-?!” Lyra was determined to be upset, but was smiling despite herself. Bon Bon began to chuckle, and so, begrudgingly, did Lyra. I let the two of them have a good laugh before I asked my next question.

“Hehe, so anyways, next question: How did you hear about me?”

Bon Bon answered, after a long post-laugh sigh. “Oh, uh… our friend Derpy told us about you. We asked her why she was always busy on Sundays.”

“First time she’s sent clients my way. I wonder why it took so long to refer somepony to me.” I didn’t really need to say that. I was just thinking aloud, to be honest.

Lyra responded this time. “Oh this was a while ago. I’ve been trying to get Bonny to come visit you for ages.” Bon Bon looked somewhat ashamed.

“So what changed?” I asked the Earth Pony.

Lyra again. “My birthday was last week.”

“Ah, so this was your present, I take it?”

“You got it!”

Her enthusiasm made me grin. “So then, last question: What can I… do for you?” Seductive almost-baritone.

Bon Bon swallowed hard, and Lyra placed a comforting hoof on her shoulder. She cleared her throat and looked me dead in the eye. “I want you to fuck my girlfriend.” she explained.

I would’ve laughed at her delivery if Bon Bon hadn’t looked so grim. “That’s certainly doable. May I ask why?”

“Bonny’s… never had a stallion.” Lyra explained.

I furrowed my brow a little. “Okay… and she wants to try it ou-?”

“She wants me to try it.” Bon Bon interrupted, obviously not at all pleased with the situation.

“I see.” I turned to Lyra. “So you have had stallions, then?”

She nodded. “Yeah… up until Bonny I never really dated mares.”

“And up until Lyra, I… never dated.” Bon Bon admitted.

“So we were thinking-” Lyra began.

“She was thinking…” Bon Bon interupted.

“That Bon Bon really oughtta-” Lyra continued.

“I believe your words were ‘need to.’” Bon Bon deadpanned.

Lyra shot her a look. “-try out a stallion. Just in case she likes it.”

Bon Bon shook her head. “You make him sound like a sandwich.”

Lyra smirked. “What’s wrong with that? I bet he’s delicious.”

”Lyra…” Bon Bon frowned in disapproval.

“What? I’m just saying: I liked sandwiches... until I tried a taco.”

I couldn’t help but giggle at that one.

“For Luna’s sake, Lyra, have some decency.” chided Bon Bon.

At this point I butted in. “Okay, I think I understand the situation.” I was beginning to get a feel for the couple’s dynamic. Lyra obviously put more stock in sex than Bon Bon, who was seemingly more of a romantic. Lyra was clearly the top, and at least somewhat absent-minded. Given her cutie mark, she was probably a musician. If I had to guess, she didn’t care much for school.

I had some hunches about Bon Bon as well, but I needed more information.

“Lyra, if it’s not too much trouble, would you mind letting me speak with Bon Bon privately?” I asked.

“Uhh… I guess so.” She shrugged.

“Great, why don’t you-” The kettle began to whistle. “Why don’t you wait in the bedroom. It’s that door right behind me.”

“Okay, sure. Uhh… what should I do?” she asked, curiously.

This is always an issue with threesomes. Sometimes in order to get to know one pony, you have to ignore the other. When that time comes, you better make sure that other pony has something to entertain themselves. “You can poke around the chests in there, if you like. I’ve got all kinds of fun stuff to look at.” I directed my attention to Bon Bon. “Is that okay?”

Bon just shrugged, and turned her eyes table-word. Clearly without the safe presence of her lover, she wasn’t exactly ready to talk to me one on one. It was a bit of a gamble, but with any luck I’d be able to get her to open up. Lyra gave her mare a quick peck and trotted off to the bedroom. “Dude… this bed is HUGE!” She said as she closed the door behind her.

“Sorry, let me just get the kettle.” I quickly walked to the kitchen to quell the shrill whistle. “You sure you don’t want some cocoa or something?” I called back.

She reluctantly accepted. “I- *sigh* - I’ll have some cocoa.” It’s always a good sign to have a pony accept an offer. Even small things like cocoa show that a pony trusts you, if only just a little.

So I brought her a mug of cocoa. She thanked me and stared into her drink, as clients often do. So I took my seat once more, and took a nice long sip of the rich brew. The cocoa was much better than I was expecting; I have to remember to buy that brand again.

“So be honest with me Bon Bon.” She looked up at me half scared, unsure what to expect. “You’ve never really had any interest in stallions, correct?”

She nodded, though I didn’t really need to ask. It was fairly obvious.

“You don’t really want to be here do you?”

She twisted her mouth into a confused grimace and shrugged. “I don’t… not want to be here.”

I hadn’t been expecting that. I’d assumed that stallions simply put her off completely, but maybe there was a bit of morbid curiosity in the back of her mind somewhere. I needed more information. But first, I needed to make her feel more comfortable, so give her a chance to alleviate some of her stress. “So, Bon Bon, do you have any questions you’d like to ask me? I’ve been asking questions since you two got here.”

“I guess so.” She took a quick sip. “How exactly… does this work? How do I… do this?” She struggled give words to her thoughts.

I cleared my throat. “Well… that depends. How this works, and what I do, depends entirely on what you want, Bon Bon.” I scooted over to her a little bit. “We can go as fast, or a slow as you like. We can go as far as you like. We can do it where you like. We can do it when you like. We can do it how you like. And above all…” Comforting smile, and gentle hoof on top of hoof. “We can do it if you like. Nothing has to happen today, Bon Bon. There’s nothing wrong with taking your leftover bits and going home.” I removed my hoof from hers before it overstayed its welcome.

Bon Bon visibly loosened up. A sigh escaped her lips as a proverbial weight seemingly lifted itself from her shoulders. “That… that makes me feel better.” A smile crept onto her lips.

“Well, I’m glad. Any other questions?”

“… just one.” She looked pensive.

“And that is?”

“…Do you… do you want to… you know… have sex with me?” There was a sort of eagerness in her voice. No that’s not quite it. She was… hopeful. She wanted to be wanted. They always do.

Hunky smile. “If I were to tell you that I did not… I would be lying through my teeth. You’re sexy, Bon Bon. I would love to have sex with you.” I may have laid it on a little too thick, but she didn’t seem to mind; she smiled and blushed.

I do love making a mare blush.

“Now… I have one more question, if you don’t mind. And then we can join your lovely lady in the bedroom.”

She simply nodded.

“Do you know why your girlfriend is so insistent that you bed a stallion?”

She let out a pained sigh. “I don’t know. She gets these ideas and… there’s just no talking her out of something once she gets it in her head.” She was sneering, but it soon melted into a smile.

“You love that about her, don’t you?” Her happiness in turn made me grin.

She giggled merrily. “Yeah… I kinda do.” The way she looked at me right then, it was so full of… warmth. It was… it was a loving gaze. A truly loving gaze. But, it wasn’t really me she was looking at. Still… it was…

nice.

“So… shall we?” I offered.

“Yes.” She said with only a modicum of nervousness.

And with that, I led her to the bedroom. Now at this point, Lyra had only been alone for a few short minutes, which is why what I saw next sort of shocked me.

Vibrators and dildos strewn across the bed. Most of them clearly used. Smack in the middle of them was Lyra, spread-eagled, with a replacement stallion filling both of her holes. Each one thrusting away under the golden hue of her magic. Bon Bon and I each stared dumbly as the mare furiously rubbed her erect little nub with a hoof, tongue lolling out of her mouth, whole body shaking violently with orgasm, howling like a wolf, juices leaking onto the sheets.

I may have gotten an erection.

When the mare spoke, her words came as a drunken slur. “Bon Bon you haaaaave to try these!” The two toys slid out of the mare, and floated haphazardly over to Bon Bon. They were still glistening from use.

“I…I… I have no words.” Bon Bon continued to stare dumbstruck at the toys being held aloft before her.

I somehow managed not to burst out in laughter, and I somehow managed to get a few sensible words out of my mouth. “I see you managed to... occupy yourself.” My own pun was lost on me, but looking back it was a rather brilliant thing to say.

“*huff*…*huff*… Guilty!” called, Lyra. “Can I like… *huff*… buy those. They’re amazing.” She collapsed onto the bed. Her remaining words were muffled by sheets and clouds. “M fmml sm gmmd rmmmt nmm.”

Bon Bon was still staring at the vibrators. “I’m…I’m just gonna put these down.” She daintily picked them out of the air, and placed them on the ground. “Lyra… did you use… all of these?”

The mare in question flopped onto her back. “Not those.” She lazily indicated a tangle of small bullet vibrators on the edge of the bed. “Seriously, though… Bonny… *huff*… those two… *huff*… I need those.” Her body squirmed and her hooves found their way between her hind legs. “My pussy… *huff*… oh Celestia, my pussy…” As she lay panting, she began to pleasure herself once more.

Bon Bon sighed. “Lyra, you are, without a doubt, the horniest person I’ve ever met.”

“Yeah…*huff*… *huff*… and you love it.” Lyra’s hooves clopped away, lending soft, slippery noises to the air. The whole affair was dead sexy. I could already feel my jeans beginning to stretch. Bon Bon was feeling the same, if the slight twitching of her legs was any indication.

Lyra continued to stroke herself. With her nethers hidden behind her busy hooves, she brought herself to her second climax in as many minutes.

Well… at least that I saw.

“*huff*… *huff*… Okay… *huff*… bed’s… *huff*… all yours.” Lyra dragged herself off of the bed, and tumbled herself gently onto the floor.

Well… gently is a relative term.

Not to self: Consider getting a carpet. Hardwood floors and sexytimes clearly do not mix.

“Lyra!” Bon Bon yelled, as she rushed to her girlfriend’s side.

“I’m okay… *huff*… landed on… *huff*… my ass.” The two engaged in a nuzzle.

Bon Bon sighed with relief. “You big dummy.” She helped Lyra to her hooves.

“Aaaw, you love me.” Lyra began to nuzzle her lover with renewed, and somewhat obnoxious vigor.

“Aaah! Lyra! Cut it out! Geez… it’s like you’re drunk.” Bon Bon pushed the nuzzler away.

“Heeheehee… I feel a little drunk.” Lyra looked somewhat seriously at Bon Bon. “So… you gonna fuck ‘im?”

She took a deep breath. “Yeah… I am… for you.”

Lyra chuckled. “Awesome.”

And then Lyra swallowed. Lyra, who had been as gung ho about this as almost any mare I’ve ever seen, swallowed. She was dreading something. ‘What the fuck? What does she have to be nervous about? She’s not the one, who’s… losing her virginity, so to speak.‘

If I had caught any signs of apprehension earlier, I would’ve steered the whole session in a different direction. However, Bon Bon verbally agreeing to... do me had been a very big step for her. Taking it back now would do more harm than good. I was sort of committed at this point.

“Let me just, do one thing, and then we can start.” I said. I noticed that the chest with my potions was already open, so I quickly grabbed one and choked it down.

“What’s that?” inquired Bon Bon.

“Birth control potion.” Lyra and I answered in unison.

It’s not often that clients actually know what those are. I raised an eyebrow at the unicorn.

“I used to date a zebra.” she explained.

Fair enough.

“So, how should we… do this?” Bon Bon inquired.

“Well, would you like to… see me, first.” I gestured vaguely toward my lower half.

“Ummm… o-okay.” Her face was an awkward blend of curiosity and apprehension..

“OOH! I wanna see that too!” Lyra chimed in.

“Alright then,” I said, as I slipped out of my constraining pants. Free of its confines my erection dangled happily below me. I sat upon my bed and presented myself.

Now that I think about it I take that pose a lot. Whether I’m just showing off, or getting head, or a mare likes to be on top, I often find myself legs spread, cock in the air. It’s a very natural position for me.

“I thought it would be more… intimidating.” Bon Bon admitted.

“Derpy said it wasn’t too big.” Lyra gave me a testing prod, and grinned. “Nice and hard, though.”

I frowned. ‘Derpy said that?’

Well… it is true, to be fair.

Anyways, Bon Bon’s reaction to my dick was rather encouraging. She giggled and blushed, eventually she worked up the courage to touch it. She poked and tested it, before gripping it in her hoof. She started to stroke me, and I let out a satisfied moan. “Does that… feel good?” she asked.

“Mmmhmmm.” I hummed, letting my eyes close. Her hoofwork was clumsy, but pleasurable nonetheless.

“Go Bon Bon!” Lyra mock-cheered. “Pump that meat!”

I snorted in laughter. “Lyra, you are incorrigible.”

“Right?” voiced Bon Bon in agreement.

Lyra clicked her tongue. “Whatever… Get that thing inside you already, Bonny.”

Ever nervous, Bon Bon nodded. “So... should I just…” She trailed off as she rested her upper half on the bed. Her hind legs spread, and her tail lifted. Whether or not she’d been with a stallion before, she understood how to accept one.

As I took my place behind the mare, her lover climbed back onto the bed. She lay face to face with Bon Bon. “Don’t worry, Bonny. It’s no big deal.” There was that loving gaze again, on Lyra’s face this time. The two kissed passionately.

Now, here is a fun fact about threesome. If you are “manning the aft end” you don’t thrust suddenly. If I were to have started fucking right then, I’d have knocked their teeth together. Also, If another guy had been “occupying” her mouth, he might find some nice new teeth marks on his stallionhood.

So I waited patiently for the two to finish smooching.

I am such a gentlecolt.

Lyra looked up at me. “Go for it, dude.”

So go for it, I did. I brought myself to her entrance and I gently penetrated her.

She was as warm and wet as any mare who came to me. Not that it was any surprise. She wasn’t exactly tight, but that wasn’t really a surprise. I’m sure her and Lyra have toys twice my size. The sex was, well… uneventful. I fucked her gently. I slowly increased my pace. I fucked her quickly. She came. I came. There’s not much to be said for it. It may have been her first time with a stallion, but that doesn’t mean that it was amazing or wonderful or mind blowing. I’m sure she’s had better orgasms, and I know that I have.

Not that it was bad, for the record.

Sex is like pizza. When it’s good it’s really good; when it’s bad it’s still pretty good.

She never really got into it, though. She didn’t thrust to match my thrusts, she didn’t scream or pant or moan. She felt good, and I’m fairly sure she enjoyed herself, but she wasn’t really… invested in it.

Regardless, I performed my duty, as it were. After finishing, I removed myself from her as gently as I entered. Lyra was looking intently at Bon Bon. “Well?” she inquired. I hadn’t really had a proper view of Bon Bon’s face during the deed, so I climbed onto the bed alongside Lyra.

Bon Bon’s face was, as I had hoped, one of bliss. “Mmmmmmm. That felt good.”

Lyra swallowed again. “S-so you liked it?” So much hesitation in her voice.

Bon Bon grinned at her lover. “Mmhmm, it was nice.” She rubbed her snout against Lyra’s.

“Not better than me, right?!” Lyra blurted.

I literally rolled my eyes. It all made sense… her remark about liking sandwiches till she had a taco… saying that Bon Bon should try a stallion ‘in case’ she liked it. She wasn’t trying to broaden Bon Bon’s horizons. She was trying to make sure she didn’t prefer cock.

What a moron.

Bon Bon glared at Lyra with a look of pure business. “Lyra…” Her tone of voice was somehow even more serious than her look. “…the entire reason for this trip was that you wanted to make sure that I liked fucking you?”

There were several seconds before she uttered a response. “… Maybe!” It somehow sounded like an accusation.

Bon Bon huffed. “Lyra… you are… the stupidest mare-!”

“What?! Nu-uh!” She pointed a hoof at Bon Bon. “What about Pinkie Pi-?”

“Shut up a second,” the livid earth pony insisted. “First of all: I’ve told you I’ve only ever had an eye for mares. And second: It doesn’t matter if I like having sex with stallions, Lyra. I like having sex with you.” She bopped her in the horn, eliciting a small ouch. “You big dummy.”

“… You’re sure?” she asked.

“Oh just… come here.” Bon Bon climbed onto the bed and wrapped her hooves around her lover. A passionate kiss… and loving embrace... these two were in love. There was that warmth again. The same warmth that was in Bon Bon’s gaze. I can’t describe it. It sort of… emanated off of them. It made me…

Sad.

At the time, I didn’t understand it, but it’s obvious to me now. I was jealous. I was so very jealous of the two of them. I wanted what they had. I wanted somepony to hold like that. I wanted somepony to kiss like that. I wanted somepony to… to look at me like they looked at each other.

Listen to me… Close would say I sound like a girl right now.

I needed to get out of the room. I needed a drink. This wasn’t any place for me right now.

“Ladies, something tells me you’d like a moment to yourselves?”

“MMHMMM!” Lyra hummed through her lover’s lips, as she rolled around the bed. (Which was still laden with erotic paraphernalia, by the way.)

I fought back a sob. “Well, should you need me I’ll be right outside.” I wasted no more time. I cantered out of the room, and left the two to their lovemaking.

I made a beeline for the kitchen. ‘Something strong. Something with whiskey. Manehattan? No, too complicated. Straight whiskey? Too simple, need a distraction. A Better than Sex? No, I don’t have any orange liqueur… or cream liqueur… or... fuck.. any hazelnut liqueur, either. Oh, I know… a boilermaker, easy, fun, perfect. Just what I need.’

I hastily prepared my beverage. I spilled a good amount of whiskey onto my counter trying to get it into a shot glass. I poured my beer into its mug so fast it was mostly head, but I didn’t really care. I took a deep breath, as I dropped the shot glass into the mug. With a clink and a splash, the dark whiskey mingled with the yellow beer… and then I chugged the fucking thing.

I felt tears as I choked down the bitter brew. As I reached the bottom of my mug, I realized that I had made it a tad too strong. In my haste I had used a rocks glass, instead of a shot. That didn’t stop me from finishing it, however; I polished off my cocktail and slammed the glass within a glass down onto my counter with a thud.

I began to breathe normally again. Now that I had had something to take the edge off, I had a new goal: clean myself up before my clients needed anything from me. Odds were that I had some time, but better safe than sorry. I went to the bathroom to get a look at myself.

I looked… fine. My eyes were a bit puffy and I had some tearstains on my coat, but nothing else. I don’t know why I was expecting to look so haggard. Maybe I felt haggard.

So I wiped my eyes, and put on some makeup to hide my redness.

…

Yes, I use makeup.

…

Only occasionally.

…

Anyways…

I cleaned myself up and I returned to my foyer. I made myself another drink, something a little more elaborate, a Manehattan. It was a good one too. My nerves began to settle, and I allowed myself to relax. I’ve had worse breakdowns truth be told. After my little tantrum I took a moment to take stock of how great my current situation was. My drink was good… the fire was warm… the music was calming… and I was getting paid to just sit there. Honestly, what did I have to cry about?

I thought about a few things while I sat there. I thought about stallions, unfortunately. I thought about mares, too. I thought about the stable. I thought about Crook. I thought about expanding upon my liquor cabinet. I thought about Sunny, and I thought about love.

I still miss her… sometimes.

As I sat and thought, I almost failed to notice a unicorn exit the bedroom.

Well, not ‘almost.’ She sort of barged out of the room, stumbling like a madmare. She panted as she half-jogged over to me. “Hey Guilty… *huff*… you got any like… *huff*… water? Cause I need like… *huff*… all the water.” She reeked of sweat and sex, a fragrance I’m quite fond of.

“There’s a pitcher in the fridge.” I offered.

“Awesome… *huff.*” She jogged over to the kitchen. I heard the fridge open and close. Lyra returned, water in magical tow, drinking the liquid in great gulps straight from the pitcher. She was so tired, but it was a good kind of tired. She managed to spill more than she drank onto her coat. “You wanna… *huff*… you wanna get your dick in there?” she asked with a tired grin.

I chuckled. “Is Bon Bon okay with that?”

She shook her head. “Not for her… *huff*… for me… *huff*… haven’t had cock in…*huff*… years.”

“Again, I ask. Is Bon Bon okay with that?”

She waved a hoof dismissively. “Yeah… *huff*… as long as she’s… *huff*… involved.”

That was all I needed to hear. I eagerly followed Lyra back into the bedroom. She made no attempts to conceal her soaking nethers from me. They were positively dripping.

When I entered I was also greeted with Bon Bon’s dripping nethers, as she lay spread-eagled on the bed, spent and satisfied.

“H-hey G-guilty.” Her entire frame was quivering. “Y-you gonna f-fuck Lyra?”

“Only if you don’t mind.” I explained. The Lyra and I joined her on the bed. “You two look tired, are you sure you don’t want a break?”

Lyra gave me a punch on the shoulder. “I look tired. All she’s been doing…* huff*… is cumming.”

“I… I f-feel too good to argue,” came a shaky reply.

“So how do you want to do this?” I inquired.

“You in my ass. *huff* My horn inside her. *huff* Fuck me into her.” She said very matter-of-factly.

It was a sound position

“You’ve thought about this.” It wasn’t a question.

Lyra laughed. “Maybe a lot.” Lyra assumed the postion. Oh her back, her horn inside her lover, her magic fondling her own marehood, she was the picture of insatiable lust.

I quickly fetched a condom. That’s a personal rule; I never go bare-back for anal. It’s a lot more… messy than porn would have one believe.

That said, it was very fun. Lyra’s back door was… how can I put this politely… accommodating, and made for a very comfortable fuck. Bon Bon came like mad, the tingle of magic can have that effect. I’ve never cared for it myself. Mid-way through Lyra grabbed one of the toys she was using earlier, and proceeded to fuck herself crazy.

I almost managed to end it in a simultaneous orgasm for all of us. I’m good, but I’m not that good. I don’t think Bon Bon managed to crest her final wave. Regardless, everypony was thoroughly satisfied.

Eventually the three of us ended up in the shower. Unfortunately, my shower only had two heads, but the mares were more than happy to share one. We talked and laughed. Lyra teased Bon Bon. I teased Lyra, much to Bon Bon’s amusement. At some point the conversation turned to current events.

“Oh hey, did you hear what happened in the library last week?” Lyra asked excitedly.

I froze. ‘Oh, fuck no.’

“Oh my goodness, YES! Gingerbread told me!” Bon Bon responded, equally enthusiastic.

‘Oh, FUCK no.’ Fuck small towns. Fuck gossip. Fuck all of it. By the sounds of it, it was the talk of the town. ‘How am I going to handle this? If it gets out that this was my fault…’ I shook myself out of my trance. I didn’t have time to ponder, I had to act nonchalant! Any non-guilty pony would be asking what happened.

“Did something happen?” I asked totally nonchalantly.

“Yeah. Okay so… do you know Twilight Sparkle?” asked Lyra.

I hesitated, trying to remember if I’d actually met Twilight outside of my session. “I’ve heard the name… is she the librarian?”

“Yeah, yeah. Well apparently last week her and her new boyfriend were fighting.”

“Who’s her boyfriend?” I was actually just curious about that.

“Some unicorn… I don’t know his name… anyways. The two of them were fighting, which I hear is not uncommon, by the way.” I gathered as much from Spike. “Apparently it was getting pretty heated, when suddenly…” ‘Here it comes.’ “… she hurled a book at him. Broke his nose.”

‘Wait, what?’

“I heard she only broke his glasses, but still…”

“… yeah… wow…” was all I could manage. I was relieved, to be sure, but also baffled. Twilight had attacked her boyfriend? Maybe that’s why it got so quiet when I yelled. Maybe it was just a coincidence. Maybe this would be a big enough deal that no one would care about me scaring a kid half to death. Maybe I’m in the clear.

Okay… that’s a pretty shitty way of thinking.

I still need to do something about that.

So, with that revelation we finished washing and adjourned downstairs. I made everyone a quick drink, for the road. I made myself another Manehattan. I made a Three Wise Mares for Lyra, who insisted on the strongest thing I could think of. (It’s really just three shots of whiskey, and I didn’t have the right kinds, but whatever.) Bon Bon asked for something light, so I made her a mixer of rum and sarsaparilla. I don’t know if that has a name. I agreed to sell Lyra one of the toys she was interested in, in exchange for her leftover twenty bits. The two mares thanked me. Lyra said they’d be back. Bon Bon said they might not. Lyra assured me we would. Bon Bon chastised Lyra. The two began bickering. I bid them goodnight, and they got up their coats and left… bickering all the way.

So there I was. A kitchen full of empty glasses. A bed covered in sweat and cum and soiled dildos. The smell of sex permeating my home, even over the burning smell of the fire. I wanted to deal with it in the morning.

Unfortunately for me, I have a client early tomorrow. I needed to clean it right away. So I scrubbed and rinsed and washed and dried and incensed and rearranged and reorganized and aired out and folded and made neat and made tidy and made presentable my home and everything in it. By the end of it I was… I’m running out of words for tired. I was famished- no that means hungry. I was… expended- no that doesn’t sound right.

I was tired. I was fucking tired. On the bright side, I was too tired to think about stallions. Too tired to worry and fret and stress about things I’d done, or things I’d thought about doing. All I wanted to do was write. I just wanted to go upstairs in my bedroom and put all my thoughts down on paper.

Even now, I’m…

Hang on… there was a knock at the door. Maybe somepony forgot something.

Hang on… I know that knock.

Oh my Celestia.

Crook is here.

Author's Note

So I hope you enjoyed this chapter, it was a blast to write.

Thank you to BlackSkulls for editing while my usual editor is swamped, I can't thank you enough.

As always, feel free to message or comment and let me know what you think, what you liked/disliked. Input is appreciated, and I LOVE talking to you all.

The next chapter might be a long one, so be patient.

Inter-escort Relationships

Chapter 10

Inter-escort relationships

Dear Journal,

Well Crook stayed with me for a few days. His visit was... enlightening. There’s... a lot going on in my head right now. It’s sort of hard to try and deal with everything at once. There’s just so much to get down on paper. It’s taking a good amount of self-control not to start frantically scribbling everything.

I think the best thing to do would be to just start where I left off...

The exhaustion of Lyra and Bon Bon’s session had set in (a fact I believe I sufficiently hammered home), but the moment I realized who was knocking on my door I was adrenaline kicked in, and I was on full alert. I slammed my journal shut and practically sprinted to my front door. I almost tripped over myself running down the stairs.

As I approached he knocked again. It was his knock. The knock he always used. The knock that let me know it was him on the other side. Two soft knocks, and then two hard knocks. When I was a kid that sound got me more excited than anything.

I threw the door open, and there he was. I barely noticed the blast of air that accompanied him. His mane was iced over from the blizzard. His teeth were chattering. His knees were knocking together. I could see his breath.

“Fuckin’ let me in!” he insisted, glaring at me.

I had just been staring at him. I was just… blown away. I was awestruck; my mouth was agape. I mean… Crook was here. Crook was here.

I hastily ushered him in, my mind abuzz with questions. How are things? How’s the stable? Did you get my letter? Are you still seeing that accountant? How were the last two years or your life? In my haste I just sort of blurted the first thing that come to my mind.

“What the fuck are you doing here?!”

Classy, Guilty. Real Classy.

Crook quickly made his way over to the embers of the once blazing fire across the room. “Fuck... throw on another log, Guilty. I can’t feel my hooves.” He said, ignoring my question entirely.

“Crook.” I deadpanned.

“Shit, Guilty, I’m freezing my ass off over here.” He shivered as he hurried out of his frosted-over sweater. “Does this town not have a fuckin’ weather team, or what?”

“Yeah, just... I dunno... it’s a fucking mess right now apparently.” I sighed heavily. As eager as I was to get some answers out of him, I knew arguing with Crook was a waste of time. He’ll argue just to argue. “… do you want a cup of tea or something, then?”

“Whiskey would be great.” He suggested as he lay down by the fire.

“I’m…" I let out a long sigh and walked to the kitchen. "I’m gonna bring you some tea.”

“With whiskey in it?” He asked.

I ran a hoof down my face. The adrenaline shock of his presence was wearing off, and I was suddenly feeling very tired again. “Fine. Sure.” I grunted back to him.

Now, normally I’d be pissed if somepony showed up at my front door in the middle of the night, unannounced and immediately started asking for booze. But… it was Crook. Crook and I grew up together. We lived in the same neighborhood.

Back then, I used to… I used to live with my father... in the apartment above his bakery. I spent a lot of time in that bakery. Sweeping or putting things on display or whatever my father barked at me to do.

I still remember the first time I saw Crook. I was sweeping the dead leaves away from the entrance and he was sitting against the bakery window, looking hungrily at the various breads on display. I noticed him staring longingly at this big loaf of cornbread that had just come out of the oven.

I was young... and stupid. I was a little colt, and he was a big kid. I wanted to be his friend. So... I snuck a piece of it out to him. My father caught me, of course, and… whooped me good. Crook ran away, though. The moment my old man came out the front door he was practically down the street already, eating his cornbread as he ran. I remember thinking… ‘He’s so fast!’ Even as my father pulled me inside. I couldn’t help but watch him run. The next time I saw Crook was about 2 years after I started going to school.

School was… real real tough. I think I’ve explained before that I was a lanky kid. Well, that made me an easy target for ridicule. I got picked on, I got bullied, I got pushed around, and I got beat up. A lot. One day, though, while I was getting kicked around on the bathroom floor, Crook showed up. I don’t really remember what happened, I just remember him. His Ivory coat… his crow black mane… but I remember his glare most of all. I remember all the anger and fury in those dark brown eyes. The next thing I remember I was waking up in the nurse’s office. When I asked how I got there, the school nurse said that an older kid had brought me in, but she didn’t know his name.

I looked for him for a while. Tried to find him base on what little I knew. Who was this kid who saved me? I looked everywhere I could think for him. I searched every classroom, every table at lunch. He was never anywhere I checked.

Well, as it turned out he never really showed up at school. He only came in once a month or so, when the school made him. It had something to do with school funding, I don’t remember exactly how it worked.

When I did find him, he was fucking around the dumpster behind the bakery. I was throwing away some day-olds, and he breaking bottles in the alley for kicks.

The first thing I said to him was “thank you”. Ever since that day, the bullies had let up a little bit.

I still remember what he said in response. “You don’t have to thank me. I was thanking you.”

And with that I had realized who he was. He was that kid. That hungry kid that ran so fast.

Then, he asked what was wrong with the bread I was throwing out. Nothing was wrong with it, I said. It was just old. He asked if he could have it. I handed him the bag, and... we were friends.

After that, Crook started going to school, and I got picked on a lot less. Whenever some dumbass thug kid tried to shake me down for money or food or whatever, Crook was always just minutes away with a can of whoop-ass. He was like my bodyguard and my best pal all rolled into one. He didn’t always save me, mind you. I still got my shit kicked in quite a few times, but he would still always make sure I got to the nurses office.

The two of us were honestly just a couple of delinquents. When school was out we’d pull all kinds of stupid shit. We’d shoplift, we’d tag shit, we’d break windows. We were dumb-ass little kids. We barely ever got caught, though. Crook was so fast, and I was so good at lying and playing innocent that the two of us almost always got away scot-free.

One day in middle school our lives changed for the better. Crook said he’d found a way for us to make some money. That day he led me to the stable, and we both got jobs as errand boys. After that I was barely ever at the bakery. It was wonderful. During the day Crook and I would go to school or fuck around, but come sunset, the two of us were running potions and lotions and condoms and booze wherever they needed to be. We’d go home late… sleep and the cycle would begin again.

Those days… they were heaven. We could buy ourselves good food. We could sneak bottles of liquor out the stable. We had plenty of time to brew mayhem all over the streets of Manehattan. When I was fifteen, I lost my virginity to a sexy young unicorn who’d just started as an escort. She said she needed to practice sleeping with stallions she’d never met, and I was happy to oblige.

Good fucking times.

When I was sixteen Crook became a fully-fledged escort at the stable, and he became one hell of an escort. He was… and still is… just a drop dead sexy stallion. He’s never had anything short of an athletic figure. He’s a pretty tall guy; he’s always been taller than me. He’s got a perfectly chiseled jawline. His mane practically styles itself. I’ve never seen him brush it, but it always looks amazing. And, of course, he’s got an absolutely massive cock.

Now, for the record, I only know that because the two of us used to double-team mares all the time. Crook was always a fan of the spit-roast.

Two years later, I turned eighteen, and followed Crook’s hoofsteps into the world of the oldest profession. We shared a room for six years.

So yeah, he’s easily the most important stallion in my life, and I owe him a lot. I can forgive a little rudeness.

I fixed him his tea (with a kick), and brought it out to him.

“Warm enough?” I inquired.

“Yeah.” I offered him his mug and he took it. “Thanks, pal.” He took a sip. And a satisfied smirk graced his lips. “Now that’s what I’m talking about.” He chuckled slightly. “Well don’t just stand there. Get warm with me!” He motioned for me to lay down by the fire next to him.

I obliged. I curled my legs up and lay beside him as he bathed in the warmth of the fire.

“So… Crook… why are you here?” I asked delicately.

He took a gulp of his little concoction and gave a satisfied little 'aah'. “Whaddaya mean, ‘why am I here?’ You wrote me a letter.” He responded. I waited for him to finish, but he was done. He was perfectly happy with his response.

“Uh-huh… and?” Was that really all the justification he needed? “I was just checkin’ in. I wasn’t tellin’ you to come all the fuckin’ way out here.”

Talking to Crook was making my accent act up.

Crook just looked confused. “You put your fuckin’ address on the thing.” He explained, apparently convinced that that clearly indicated an open invitation.

“So you could fuckin’ write me back y’idiot!” I punched him the shoulder.

Crook snorted in laughter. “Fuck that.” He took another long sip of his swill. This time he gave it a scrutinizing glance. “For fuck’s sake Guilty, too much whiskey.”

“Oh fuck right off, Crook. I’m afraid I’m not privy to the nuances of puttin’ whiskey in fuckin’ everything.” I was acting offended, but it was just that... an act. It’s just… how we are together.

“Fuck you, Guilty.” He snarked.

“Fuck you too, Crook.” I snarked right back. Our gazes met and we just grinned at each other. “I fuckin’ missed you, Straight Arrow.” I confessed.

“I missed you too, Sour Dough.” He wrapped an affectionate hoof around my neck and pulled me in close.

I hate my real name, Crook is the only pony who calls me that. Likewise, I’m the only pony who gets to call him Straight Arrow. To his clients, he’s just… Crook. It’s a nickname he got because of his cutie mark, a bow notched with a bent arrow. (Irony!)

He’s always thrived by following his own code. Doing what he believed in. By proxy, he excelled at breaking the rules of others. After all, that’s his special talent… staying off the straight and narrow path, and learning all the crooked ones.

In his early life, it was very literal. He knew every back alley, every broken fence, every shortcut, and every hiding place in Manehattan. If he really needed to, he could get away from anypony in that city, and more than a few times he did. Of course, it helps that he could run faster than most ponies.

Later on, Crook just excelled at making a less than honest bit. Stealing, working the occasional shady job, gambling, that sort of thing. I always told him if he put his mind to it, he could probably become a criminal mastermind. He’s just that good at being bad.

We had a moment there, lying by the fire in the middle of a blizzard. We hadn’t seen each other since I left Manehattan, but in some ways it was like we hadn’t missed a beat. It just felt so right to see him again. I leaned into his embrace. “So… I really gotta get some sleep, Crook. I got a client tomorrow morning.”

“What? We gotta catch up, Guilty. I got a hundred questions!” He jostled me in the hug, attempting to shake the exhaustion from me.

“Fuck, Crook. I do too.” I was about to collapse. “But… in the morning…” I leaned into him more. “I’m fuckin' bushed.”

He chuckled at me. “Fine.... ya baby.” He pushed me off of him rather suddenly. “Off we go.”

I pulled myself onto my hooves and led my friend to the bedroom. Once inside I lit a few candles, and Crook’s eyes went wide. “Fuck me… Is that...?” His jaw dangled freely as he gaped at my mattress.

“Yup… enchanted Cumulus… King-sized.” I tiredly explained.

He shook his head in disbelief. “If business out here is this good… I might just have to join you.” He was joking, of course. Crook lives and breathes Manehattan. He could never really leave.

“It’s not.” I said tersely.

“Then where did this beauty come from?” He inquired eagerly. As much as I really didn’t want to breach that subject, I was too tired to come up with a clever lie.

“Sunny.”

“Yeah? Well, she was fuckin’ loaded.” He didn’t pause for a moment. He knows most of what went down between Sunny and I, and how hard I took it. Some ponies might’ve frozen up at the mention of something like that, but not Crook. He just carried on like it was no big deal. He knew that that’s what I would have wanted.

Sometimes I think he knows me too well.

“Arright… I’m goin’ upstairs.” I yawned once more and made for the bedroom door.

“Whoa. Whoa. Where ya goin’?”

A memory rang through my head.

‘Crook can’t sleep alone.’

“I just need to grab a pillow.” I lied.

“There’s like, eight here. We got fuckin’ plenty.” He looked at me like I was crazy.

“I’m used to mine… can’t sleep without it.” I lied again.

“*Pffft* What a wuss.” He teased.

“Yeah yeah, call your host a wuss. That’ll end well.” I warned jokingly, and then left the bedroom.

As I treaded upstairs I scolded myself.

‘How do you forget something like this, Guilty? You don’t see him for two years, and suddenly you forget shit like this? Get it together.’

When Crook was a little kid, before I even met him, some... bad stuff happened to him. He told me what happened once… only once. He was drunk, and I don’t’ even know if he remembers telling me, but suffice it to say: Crook can’t sleep when he’s alone. Back when we shared a room, if I was ever busy and he was free, he would up wait up for me so we could sleep together.

Not like that.

Anyways, I fetched my pillow and returned to find Crook practically jumping on my bed. He was so… giddy. “Guilty… this thing is awesome.” Of all the things we escorts utilize, be it potions or oils or condoms, the thing that we tend to ‘geek out’ about the most is mattresses.

“Quit prancin’ around like a fairy… it’s fuckin’ lights out.” I began to blow out the candles. Each quick breath extinguished an orange light, and added an extra shade of black to the cozy room. Once the lights were all out, save the glow of the fire from under the door, I joined Crook on the bed, and the two of us tucked ourselves beneath the sheets. I unconsciously slid to the middle of the bed, placing my back firmly against his.

This is how we always slept. We used to share a bed quite often. Sometimes we were alone and sometimes we were accompanied by a mare (or several mares), but we always… had each other’s backs.

As I drifted off to sleep, I half expected my mind to drift once again to thoughts of stallions. Surprisingly, it never happened. For whatever reason, being around Crook didn’t bring up thoughts of my old gay sessions. If anything it kept me from thinking about it.

I can’t explain it.

I slept well… very well. Something about sleeping with Crook just feels… right. It feels like… home. I’ve lived in this cottage for two years now, but it never felt more like home than it did that night.

It makes sense, I suppose. The room we shared at the stable was the first real home I had.

I don’t… I don’t count the bakery.

Anyways, the next morning I was awakened a hoof poking at my shoulder.

“Hey Guilty… get up… I’m hungry… Guilty… hey… make me something.” Crook continued to poke and prod at me, attempting to rouse me.

“Mmmmwhat time izzit?” I mumbled, before bolting upright. “Oh fuck, what time is it?” My eyes quickly darted about for a clock. Eight a.m.. Still an hour to my appointment. “Oh, thank fuck. I did... *YAAWN*... I did not want to have to rush through this morning.” I sighed with relief.

“Fantastic, you’re awake… make me breakfast.” He insisted.

I was still getting my breath under control when I responded. “Just… have a bowl of cereal.”

“I would, but all you have is that kiddy sugar-shit. Make me a fuckin’ real breakfast.”

I crawled my way off of the bed. “Fine… grilled cheese okay?” I didn’t need to ask; it’s his favorite. I just wanted to see him excited.

And excited he was. “Fuck yeah! You got any tomaotes?” His face was stuck in a huge grin.

“Mmhmm. Good ones.” I began walking to the kitchen and crook joined me.

“Good because I want some right-“ Crook began.

I finished his sentence for him. “In the sandwich with a little bit of pepper, I remember.”

He chuckled and gave me a little punch on the shoulder. We do that to each other a lot, now that I think about it.

So I made him breakfast: grilled mozzarella and tomato on rye bread, with a glass of orange juice. I made myself the same.

Crook happily chewed away at his sandwich. “Mmh. Gvilty. Yoh fandwiches rre the bvest.” He garbled through his meal.

I swallowed a mouthful of cheesy goodness. “For fuck’s sake, Crook. Don’t talk with your mouth full.” I chastised. It was sort of a reflex. Crook used to come to me when he needed help with the non-sexual aspects of escorting; I’ve given him more than a few lessons in manners.

After that, the two of us spent a long while catching up. I told him about Ponyville. I told him about my friends, Derpy and Pinkie Pie. I told him about business, and how much I make. I told him about all the fun toys I’ve acquired since I got here.

He told me about the stable, and how everypony’s doing. He told me about some ridiculous new law about the size of soda restaurants can sell, that the mayor just issued. He told me (at great length) about how difficult his journey to my cottage was. In his defense he did sort of brave a blizzard to get here.

Eventually our conversation drifted to making a plan for the day. “Okay so… I have a client soon, I’m gonna need you either outta here, or squirreled away upstairs, your call. And after that… I dunno. You feel like helping me carry groceries?”

Crook just shrugged. “Sure. You can show me around town or whatever.”

“There isn’t really much to show.” I pointed at the plates. “Now wash this shit, would you?”

“What? Just get your...” He paused with realization. “…Oh, right… no gofer.” He just shrugged, collected our dishes,and trotted to the kitchen. For a moment I just sat and enjoyed the sounds of someone else doing the dishes. It had been a long-ass time since somepony had been here who wasn’t a client.

And that somepony was Applejack. She stopped by when I first moved to town to yell at me.

That was not a good day.

Regardless, Crook finished up and opted to lock himself upstairs in my bedroom. It was a bit unorthodox, but I trusted him to keep his head down. After all, he understands the nature of the job. He knows that even the slightest thing being off can ruin a client’s experience.

So together the two of us prepared my home for a visitor. He helped me make the bed, helped me shovel the entrance. He helped me get candles and a fire lit. He even helped me pick out music. After the house was ready, he headed off upstairs, while I awaited my client, Junebug.

Junebug is an ‘every-now-and-then’ with a penchant for small talk. She’s a florist; she grows and sells flowers in the market. She’s pretty good too. I’ve walked by her stand a few times; there are some good looking bouquets there. I’ve always found flowers a little confusing… I can never decide if I wanted to eat them or put them on display. Still, they’re easy to talk about. I’ll usually bring up a few flowers and she’ll tell me a thing or two about them. Simple stuff. She’s very amiable, always happy to tell me anything I want to know.

Her knock came right when it should have. I double-checked my bedroom door, to make sure Crook was sequestered away, and I opened the door. Dressed in scarf and coat, she stood outside my little cottage. It was a chilly morning, but any traces of last night’s wind were long gone, making it somewhat… I want to say brisk is the word. It was a brisk morning.

Anyways...

I donned my dashing grin. “I hope the walk here wasn’t too nasty. We had quite the blizzard last night.” I said as I bid her entrance.

She cracked a smile as she came in. “No, it was just fine. Thank you for asking, though.” I gestured for her to hoof me her coat, which she did, and I promptly hung it.

“The snow wasn’t too deep?” Appearing concerned always makes a client feel like their needs are being catered to. It never hurts to double-check if everything is okay. After all, some ponies’ natural instinct is to forgo their own wants and desires. This can make catering to a pony’s needs… troublesome. So… always double check.

Never triple check though… then you just seem like a worry-wart.

She giggled somewhat merrily at the attention I was giving her. “The snow was just fine… I think the weather team cleared a lot of it this morning.” She made her way to the table in my foyer, and took her seat.

“Would you like some cocoa? Or tea?” I offered like a good little escort.

“No, I’m okay. It’s plenty warm in here.” She smiled. She has such a tender smile. “Thank you, though.”

“Well in that case…” I sat across from my client. “…How are you, Junebug?” I didn’t have to fake a smile, it came naturally.

“I’m well. Things are going fairly nicely right now. Business is always good in the winter.”

I cocked an eyebrow at that. “Oh? How’s that? I would’ve assumed you’d shut down for Winter.”

She shook her head. “Mmm-mmm. I have a green house. And in Winter, ponies can’t go around picking wildflowers.”

“So they have to go through you to get their precious flowers?” I joked.

“Exactly. Mwahaha!” She laughed mock-evilly.

I giggled.

“But as you know,” she continued “there are a few florists in Ponyville. I’m afraid I don’t have a monopoly like you do, Mr. ‘Ponyville’s Only Escort.’”

“It does have its perks.” I admitted. “I never have to worry about ‘healthy competition.’ Speaking of, is Roseluck still screwing with you?” I inquired. Apparently this one mare has a tendency to undercut Junebug’s prices fairly consistently.

“Ugh…” Her expression soured. “Every time I have a sale… so does she. Whenever I put up new prices… she puts up ones that are just a bit or two less. I don’t even think she’s trying to hide it anymore.”

Comforting smile. “Well… I’m sure she’s just desperate because she knows that she has an inferior product.”

Junebug snickered. “Thanks. That makes me feel better.” She quickly threw on a false ‘high society’ accent. “You should see her bouquets, though. Her use of Baby’s Breath? Just gaudy.”

I laughed, but not because I thought it was all that funny. I laughed because she sounded remarkably like Rarity. She always sounds like that whenever the topic turns to fashion.

A question occurred to me. “Okay, so… What is baby’s breath? I’ve heard ponies mention it, but I never really knew… what it was.”

“Oh, it’s the little teensy white flowers you see in bouquets sometimes. You usually use it to fill in gaps between bigger flowers.” She explained.

“Huh. Well, you learn something new every day.” I mused. I was rather enjoying myself. Junebug’s interesting, funny, witty, more than a little cute. It’s nice talking just to talk sometimes.

“So how are you, Guilty?” She asked. “Anything interesting going on?”

‘The librarian and her boyfriend got into and fight over me, and she broke his nose (maybe.) My best friend showed up unannounced at my doorstep and just barged into my life. He’s upstairs right now, hidden away. I screamed at a kid and made him cry, but it was an accident.’

“Nothing much… I’ve been thinking of ordering some snowshoes. That’s about exciting as it gets all the way out here.” I lied with a grin.

“Supposed to be lots of snow this year.” She said. “That probably means a lot of business for you, right?”

I tried to follow her logic to no avail. “What makes you think that?”

She shrugged. “I dunno. I figured ponies would all stop by to… you know… warm up a little.” She tried to be subtle about her implication. She was not. She could’ve done without the eyebrow wiggling and I still would have gotten her meaning.

“Actually, Summer sees the best business.” I explained. “When the night is so hot you can’t sleep. When you spend all day sweating. When the heat gets under your coat. That’s when ponies… need it.”

“Makes sense.” Junebug began to half-lid her eyes at me. “Well, I’m not sure about other ponies. But I think that I need it. Right now.”

Clumsy and obvious as Junebug was, she made her point. It was time for sex.

‘So soon? Oh well, it was nice while it lasted.’

“Well then… to the bedroom.” I smiled falsely. I hid any trace of disappointment from my voice. Never appear discouraged; it tends to hurt the client’s feelings.

Now… I really enjoy the small talk I usually share with Junebug, as I’ve said. But sex with her is… a chore for me. Not that there’s anything wrong with her. I’m sure there are plenty of ponies who would fully enjoy providing this service to Junebug. I’m just not one of them.

See, Junebug likes to be dominated.

I’ve never really understood the whole BDSM… thing. Honestly I’ve always found it rather silly. Now I don’t have an issue with taking a particularly active or a passive role in sex, but this is different. The whole premise of pretending one pony is at the mercy of another is just weird to me. It makes sense to the ponies who do it I imagine, and I’m sure as shit not one to judge. It just doesn’t float my boat.

As we went to the bedroom, I prepared myself for the act. It’s not easy for me to be so dominating so naturally, it takes a bit of forethought. I have to appear controlling. I have to appear merciless. I have to appear sadistic.

I am none of these things.

“So… on the bed… let’s get you tied up.” I delayed slipping into the act for as long as I could. I was still just… Guilty.

“O-okay.” She was already so hungry for it. Her whole body was shaking from excitement. I get the feeling that she doesn’t masturbate. She always seems so… backed up. She’s not seeing anypony either, as far as I know. I might just be her sole source of orgasm.

I pulled a length of rope from one of my many trunks. “Lay still.” I instructed. She instantly complied, ever eager. And with that, I began the lengthy task of binding a mare.

Now, if I may split hairs. I don’t bear any particular disdain for bondage itself. The sensation of ropes or cuffs or whatever can be very enjoyable in moderation. Bondage isn’t inherently about control. Sometimes cuffs just feel good because they do. I only take issue with the whole… mind game that comes along with sadomasochism.

I’ve actually gotten pretty darn good at tying up mares. I never had a knack for it when I was starting, but I improved with time. Knots and ropes came as second nature anymore. An intricate pattern across her torso. Her flesh bulging around each line of rope. Her tail tied into a permanent lift. He fore hooves bound to her hind hooves, and placed flat under her. Her rear end stuck high in the air. Her hind legs spread far, opening the lips of her marehood. It was all so easy now. I decided to top it all off with a blindfold. She dug it, thankfully.

Oh for the record, I use a nylon rope. Regular rope takes a lot of preparation, otherwise it just fucking hurts. Trust me.

With the deed done, I had only one thing to do before I had to begin. I guzzled a blue flask down and began my act.

“Tell me Junebug. Have you been a bad pony?” It was an obvious line, but I couldn’t help it. Honestly I feel restricted creatively when I have to do this.

“N-n-no.” She whimpered, already completely dedicated to the act.

I opened a nearby trunk, making extra sure to do so loudly. Unexplained noises can add to the tention. “Don’t lie to me Junebug. You know what happens when you lie to me.” My voice became deep and raspy. I don’t think I’m very good at sounding mean. I feel like I sound comically sinister. Still, Junebug seems to enjoy it.

“N-no! I swear! I’ve been good!” She’s actually quite the actress. She sounded genuinely distressed. I suppose that’s part of what makes this so hard for me; I don’t like hurting ponies. In the end, this whole thing is her idea but… still. On some deeper level it just feels so… wrong.

“You’re lying.” I hissed. I produced a paddle from my crate. Her favorite.

She began to plead. “No… it’s… it’s the truth. I swear, Guilt-”

*WHAP!*

Despite my every inclination I struck her on the behind, silencing her completely. My teeth dug into the grip. The wood tasted sour in my mouth.

“GUH!” She bellowed.

“That’s ‘Sir.’” Ugh… It felt so stupid. Such… needless animosity.

“S-s-s-sorry.” She whimpered.

*WHAP!*

“MMMF!” She drowned he scream into the cloud beneath her.

“Sorry, what?” I asked

“S-Sorry Sir!” She quickly responded.

“Gooooood.” I crooned as I ran a delicate hoof across her tender backside. “Now… tell the truth… you’ve been a bad pony haven’t you?” I took up my paddle once more, ready for more swings.

“No, sir. I haven’t!”

*WHAP!*

“AAAH!” She cried.

I brought my voice to just above a whisper. “You. Are. Lying.” I find that speaking softly can be just as intimidating as shouting. It’s also much easier on your throat.

“I swear, sir. I’ve been a good pony! I’ve been a-”

*WHAP! WHAP!*

I put two swift strikes across her cheeks, which were beginning to get swollen and red.

“Okay! Okay!” She was wheezing, voice shaking like a leaf. “I-I’ve been a b-b-bad p-p-p-pony! I’ve been a baAAHAAHAAD PONYYYYYYY!”

And then came the waterworks. She was bawling.

‘Why does she like this? Why does she want me to make her cry? Who wants to cry?’

If she didn’t have a safe word I would’ve ended everything right there. Normally when one of my clients breaks down into tears everything comes to a grinding fucking halt, but apparently she didn’t want me to stop yet. She wanted to keep playing.

“Sshsshsshssh, It’s okay.” I climbed up onto the bad and over to her face. I gazed at her messy face. Tears were wetting the blindfold, putting to dark eyespots in the fabric. Mucus was dripping from her nose. “Oooh… so pitiful.” I playfully flicked at her ear. “Don’t worry, dear. Your punishment won’t be too severe.” I like to always appear sympathetic. It makes me feel somehow better about the whole ordeal.

“M-m-mmmh-h-hmmmm” she whimpered. I pulled myself off the bed and took up my paddle once more. Her ass was swollen red now, and her lips glistening and pink. I bit into grip and swung my neck hard.

*WHAP!*

When spanking a mare, it’s always important to swing just hard enough to hurt, but not hard enough to harm. No client wants to end up walking around all day with scars on their ass.

*WHAP!*

A paddle works well for this. It will certainly make an ass red, but it won’t really cut them or anything. Ponies who use whips and such have to be extra careful.

*WHAP!*

There’s something else that’s important to keep in mind. Counterintuitive as it may seem, I cannot emphasize it enough. The sub is always in control.

*WHAP!*

The sub is the one putting themselves in a dangerous position. No matter what the dom wants to do, if it isn’t okay with the sub, they don’t do it. That’s why a safe word is important.

*WHAP!*

A dom has to be able to recognize when a sub is pretending to hate it, and when they actually hate it. A sub has to be able to make it clear that they want their dom to stop.

*WHAP!*

This can be difficult at times, particularly when the sub is gagged and bound. In these situations you still need a signal that can be picked up on by the dom: rapid blinking, a series of short grunts, anything.

*WHAP!*

The best thing a pony can do, however, is to always make sure they trust the pony they’re playing with. If your partner genuinely cares for you, they’ll be much less likely to go overboard.

*WHAP! WHAP! WHAP!*

After ten solid smacks her back end looked remarkably like a tomato. Her marehood was dripping onto the mattress. Her mouth was fixed in a silent scream, drool dribbling down her gaping lips. Even obscured by pain, I could still see the ecstasy on her face. She loved every second of this torment.

“Now… that wasn’t so bad, was it?” I sidled up against her again. “Are you sorry?” I petted her head affectionately.

“Y-y-y-yes.” She tried to hide the pleasure from her voice, but it was still evident in her tone.

“Say it.” I insisted.

“I-I’m sorry that I was a b-bad pony.” She said through her quivering.

I laughed. A big goofy evil chuckle. “No. Nonononono, stupid girl.” I think I hate berating her the most. The first time we did this I wasn’t degrading at all. Next time she asked me to insult her a lot more, so... it’s just part of the routine now. “That was for lying to me. I still have to punish you for being so…very…bad.”

I violently flipped her onto her back. She gasped in surprise, as she found her legs tied spread in the air. “Now… tell me Junebug.” I place a hoof sternly on her pussy. It was so very hot and wet. “Why are you a bad pony? What did you do that was so bad?”

She was still struggling with her new orientation when she answered. “I… I don’t want t-”

*Smack!* I give her crotch a delicate yet forceful little slap. “It’s not about what you want!” I seethed mock-angrily. “It’s about what you have to do!”

“N-n-n-no!” She pleaded.

*Smack!* “Tell me.” I insisted.

“I don’t wanna! I don’t waahaahaanna!” There were the tears again. Every drop and every sob ate at me. Everything about it just felt so… dirty.

An idea occurred to me. A strategy I hadn’t used in some time. “Oh… you don’t want to? Then I’ll make you want to.” I slid my face up to her crotch, letting my breath tickle her. I gave her a slow purposeful lick, relishing in her flavor. She squealed in surprise and delight. “Do you like that?”

“Y-yes…”

*Smack!*

“Yes, sir!” She quickly corrected.

“Good… then here’s what’s going to happen. You don’t get to come until you tell me alllllllll about the bad things you’ve done.” My words felt forced. My normally excellent dialogue skills were failing me.

This was fine. Good even. Delving into her moist folds, licking up her juices, I could focus on the task at hoof. Probing and tickling and sucking and kissing and lapping, it was very calming. I proceeded carefully, not to allowing her over the edge. She tasted so good. Eventually I pulled away from her, leaving an aching quivering pussy to suffer from deprivation.

“D-d-don’t stop!” She implored.

“How about now? Do you feel like talking?” I ignored her pleading entirely.

“Oh pleasepleaseplease don’t stop!” She didn’t just sound desperate, she really was. She craved release.

“Oh, but if I keep going, you’ll finish right now… and we can’t have that, now can we?” I ran a hoof across her lips delicately: just enough stimulation to keep her on the precipice.

Her whole body shook in frustration. She gyrated her hips within her bindings in a vain attempt to eke more pleasure out of my hoof.

“Well go on… tell me all the bad things you’ve been doing.” I taunted her.

She listed off a number of apparent misdeeds she’d performed over the past week or so. Lying to a friend to get out of a favor. Sneaking extra snacks from the fridge. That sort of thing. Finally, though, she said something that was rather interesting.

“I… I… I… I had naughty thoughts!” She blurted.

“Oh?” I was actually kind of curious about that. “Do tell.”

“There’s a stallion… his n-n-name is Baritone.” She shakily explained.

“And?”

“And he c-c-came by to buy some daisies for p-p-picnic… w-when he left, he s-smiled at me.”

“And?”

“And I when I got home I k-kept thinking about him…”She continued.

“About him how?”

“About him…. on me… touching me… holding me…”

“Fucking you?” I offered.

Fighting back a sob, she nodded.

I chuckled. “You know something Junebug?”

“W-w-what?” She asked nervously.

“You are a bad bad pony.” With that I dove into her legs with renewed vigor, my tongue slithering into her. Within a moment she was already screaming in pleasure. She came quickly. The ropes stretched as her muscles tensed, orgasm pulsing through her body. A splash of hot liquid hit my tongue. She came so hard she wet herself. This is a thing that happens sometimes. It’s called stre-

I’ve already explained this haven’t I?

Anyways…

I removed my head for betwixt her hips. I couldn’t help but gaze on as she continued to leak onto the bed. Her liquid flowed onto the sheets, staining them. There were tears streaming down her face, but her lips were bent into a smile.

“Oh… look at that. You made such a mess.” I observed.

“I’m sorry, sir.” She was floating on a cloud of ecstasy.

“I suppose I’ll have to punish you for that too.”

“Okay!” She said eagerly. She could no longer even pretend she was not enjoying herself.

I rolled her off of her mess and flipped her over onto her back. Her ass once more propped into the air, I mounted her. “Since you’ve been such a messy pony, I think I’m going to fuck you.” I said as I wriggled out of my jeans. I sounded so corny.

“Okay, Sir!” Her ass twitched in anticipation.

I thrust into violently. She usually asks me to be rougher, so I figured I’d go all out from the get go. She was more than ready for it. Her body accepted me quite easily. She was moist and loose and so very hot.

I’ll say this. A lot of guys will speak ill of girl who is ‘loose’ in the literal sense. Honestly it doesn’t make sex any more or less enjoyable. Tight or loose, the experience almost always feels good.

I pressed as much of my weight onto her as I could. Any sort of pressure served to heighten her experience. I fucked her hard and fast, and she enjoyed it thoroughly. Each thrust punctuated by the wet slapping noise of flesh on flesh. I rattled off insults when they occurred to me. I called her a slut and a whore and a bitch, much to her satisfaction.

Now, there’s a very important thing that one must do both as a dominator and as an escort.

One must never make it personal.

I don’t know why... but when I was fucking Junebug and insulting her and everything. My false anger… started to turn real.

Now part of the problem was Junebug herself. She didn’t do anything to make me angry it’s just…

She kind of looked like Carrot Top. Especially with that blindfold hiding her face. Her colors aren’t quite right, and her mane is styled a little differently but... the similarity is there.

For a few seconds I was… furious. I’m not even all that mad at Carrot Top, it was just… with the role-playing and that hike we had and Crook showing up and the whole Spike-Twilight incident... I had a lot of emotions all bubbling near the surface and…

I dunno.

I caught myself though. For a few moments I was as mad as I’ve ever been, but it didn’t last. I just reminded myself that I was with a client and I just… swallowed all my anger.

Once I calmed myself I proceeded to fuck my client with good, old-fashioned, fake fury. Through the insults and thrusting and sweating I managed to make her come again. She wet herself again as well, splashing my testes. It honestly didn’t bother me. It was just pee.

Her climax begat mine. I emptied myself deep inside her as her hot walls clenched me. She likes me to finish inside her. Mares often do.

For several seconds we just enjoyed the moment. I felt myself slowly soften within her as she shivered in delight. Regardless of the session itself, I can always appreciate a job well done. Eventually I dismounted her, and lay myself down beside her.

Another thing to keep in mind when being a dominator, is when it is okay to break character. Breaking character can ruin a pony’s whole experience if done too early, so try to get a feel for when the sub is finished.

She was definitely finished.

“How was that?” I asked, allow my voice back into its normal cadence.

“Amaaaaaaaaaaaaaaazing.” She responded drunkenly. I removed her blindfold to meet her gaze. Her eyes were puffy and her face was still covered in tears and mucus, but she looked… grateful. I may never understand exactly what pleasure she gets out of her session, but I’ll always be happy to provide it. “Thanks again, Guilty.” She chuckled somewhat ashamedly. “I…I think…shower…”

“Of course.” I untied her carefully, the ropes had worn into her skin a bit, but they marks they’d left would fade soon enough. Junebug likes to shower alone, so while she trotted upstairs I washed my face in the kitchen sink. I was still going to shower afterwards, but it let me wash the smell of pussy and urine off of my face.

She finished up and met me back downstairs. I’d prepared some tea, just in case she felt like some. She did not.

“So… hehe… thanks again.” She’s always embarrassed once the session is over. She was blushing hard.

“Not at all, Junebug. Your business is always appreciated.” Sexy grin.

“O-okay. Here’s *ahem* forty.” She produced a small pouch of coins from her hanging coat, which she then put on. She’d only just broken into her second hour, but she still saw fit to pay for it.

I wasn’t going to argue.

“Thank you so much, Junebug. Do come back.” I gracefully took her pouch.

She began to make for the door. “I-I will. See you then.”

“Of course. Bye now.”

She nodded, and with that she left. She often leaves rather quickly after her shower, but lots of clients are like that. Some are ashamed, some are embarrassed and some just want to go home. Either way, it’s no big deal. Honestly part of me was glad she left so quickly. I really needed a shower.

First, though, I had to let Crook out of my room. I figured he’d be going stir crazy up there all alone. He’s not the sort of stallion who can really sit still. I trotted upstairs and went to my door, and when I opened it I found him lying on my bed, taking a belt of whiskey.

“Wha- Where did you get that?” I asked, knowing full well the answer to my question.

He coughed loudly. “Liquor cabinet.”

I threw him a look.

“Oh relax, I’m not even down to the label.” He snickered and handed me the bottle. I just put it on the floor.

“Crook… it’s ten-fifteen.” I chided.

“Hair o’ the dog, Guilty. Hair o’ the dog.” He hopped out of bed. If nothing else he appeared sober. He looked me up and down. “You gonna shower?” He asked.

“Yeah”

“I’ll join you… I smell like fuck.” He ran a hoof over his face.

“You smell like whiskey.” I chided him again.

He just rolled his eyes.

“When did you even grab this?” I began to wonder if he hadn’t snuck out during my appointment. As good as escort as he is... he’s still Crook. I wouldn’t put it past him.

“I stowed it up here while you were fuckin’ with the phonograph.” He explained.

“For fuck’s sake, Crook.” Still, it was better than the alternative.

“Yeah yeah yeah...” He said. And then the little confrontation was over.

So, the two of us hopped into the shower. We used to shower together all the time. Crook eyed my collection of soaps and shampoos. “You use all of those?” He asked.

“Nah, I use this vanilla peach stuff mostly.” I pulled the bottle off of the shelf.

Crook snorted. “You’re such a wuss.”

This time I rolled my eyes.

The water in the pipes was still warm from Junebug’s shower, which was a good thing because those pipes get really cold in the winter. Crook grabbed the cheapest shampoo he could find and proceeded to wash himself sloppily. I offered him a loofa, be he declined. I opted to use one myself. The loofa felt good on my skin. It was so rough and cleansing. It felt like it was cleaning everything off of me… everything out of me. It felt so good to scrub scrub scrub get clean clean clean.

‘Oh no…’

I could feel it coming. I was going to have a fit. I was going to scrub and clean and wash and cleanse and brush and scrape until my skin was raw. I was going to freak out. I had to stop. I had to stop myself.

I violently threw the loofa on the shower floor. My breath had become labored, and Crook took notice. I tried not to look at him… I was… I was too embarrassed. I was so ashamed… perhaps as ashamed as Junebug.

He understood right away what was going on. The next thing I knew I felt the loofa on my back. “Nice and slow, Guilty.” Crooks voice came so gently. Gentle didn’t suit him, but I was grateful for it. “One scrub at a time. Deep breaths. Just like Mama taught us.”

I cringed slightly. I honestly didn’t want to think about her.

Crook continued to clean me, scrubbing my neck and beck. “This happen a lot? I haven’t seen you like this in years.”

“Ju-ust...” my voice was cracking; I cleared my throat. “Just a couple times.”

There was a long pause before he spoke again. He finished up with my back and began washing my ears and mane. “Y’alright?”

“Yeah…yeah I’m fine.” I didn’t sound entirely sure of myself. I wasn’t. It felt really good to have someone wash me. When I was starting out I used to get cleaned by other escorts every now and then. If I was freaking out in the shower and someone saw me, they’d always offer to wash me. Better than having me scrape of a layer of skin. When I got a little older and a little more jaded, I’d sometimes do the same thing for the kids starting out. It’s just sort of… a thing amongst us escorts.

As I pondered on my time in the stable Crook continued to clean me. When he was done he put down the loofa, capped my fragrant shower gel, and turned off the nozzle. The din of the shower died to a quiet trickle, as water drained from the pipes. I was feeling better, but still somehow on the verge of tears.

I felt a hoof wrap around my shoulder. “You’re okay, Guilty. You’re okay.” I looked up at my friend, to find a friendly smile looking down at me. I’m not sure why but that smile made the tears flow.

So, I cried. Soaking wet, and being held by my best friend, I cried my eyes out. I bawled until snot ran down my face and my eyes grew red and puffy. I cried like Junebug cried when I paddled her. I cried like I cried on that night not too long ago, all alone. I bawled and cried and howled and wept and wailed into Crook’s shoulder.

There was just… so much emotion in me. So much raw fucking emotion. Happiness and sadness and anger and misery and fear and hate and love and just fucking everything. So much inside me that just needed out.

It just felt… it just felt like it was okay when Crook was there. It felt okay to feel all of these emotions that had been stewing inside of me. Crook was always there for me when I needed him, and it would appear he still is. Fuck, I missed him.

As my wails began to give way to hushed sobs, he said it again. “You’re okay, Guilty.”

“Y-yeah.” I whimpered before pulling myself together. “Yeah, I’m okay.”

Crook snickered and removed his hoof from my shoulder. “What… no ‘thank you’? You’re welcome, asshole.” He punched me in the shoulder again.

I love him for that. He just, moves on and pretends like nothing happened… but in a good way.

“Thanks.”

“Damn straight. Now… what’s the plan? I’m thinkin’ lunch soon, we gonna head into town?”

“Lemme... *ahem*... lemme clean up, and we’ll get going.” I responded, removing any leftover sadness from my voice.

Wow… fuck. It’s late. There’s a lot more to write, but I have to get to bed. I’ll write more tomorrow.

Author's Note

Hope you enjoyed! Thanks again for reading. Don't forget to tell your friends about Guilty's Exploits.

Escort-client Relationships

Chapter 11

Escort-client Relationships

Dear Journal,

After sleep and breakfast, I’m feeling quite rested. I have a client this evening, but that gives me plenty of time to write. Hopefully I can get through everything else before she shows up.

I’ll pick up where I left off.

Crook and I were heading into town. I’d wriggled into my jeans and brushed my mane, threw on a nice thick jacket, grabbed some saddlebags for each of us and the two of us set out.

I already had a decent plan. I was going to show Crook around town first, show him what meager few sights Ponyville has to offer. The Library would be my first stop; it’s a pretty cool looking building. As a bonus, it would give me a chance to hopefully clear things up with Spike, maybe grab that book about Zebras this time. After that, maybe Pinkie’s Bakery. Or wait… not Pinkie’s Bakery, she just works there. Regardless, it’s also a pretty neat looking place. After that, though, I didn’t really have a plan. I figured Crook would probably find something (or more likely some mare) to entertain himself.

So, the two of us began the long march into town. The snow crunched underhoof. Junebug’s tracks leading from my cottage were still visible, a guilty little trail sneaking away in the snow. I briefly hoped no one saw her slinking back into town. That would just suck.

“Fuck, Guilty. Seriously, why do you live all the way out here?” Crook griped, shivering.

“A few unhappy citizens made a case to the mayor that the nature of my work was not appropriate within city limits.” I explained cattily. “Too many kids running around town all day; you never know when they might hear something. Celestia forbid a parent be forced to explain what sex is to their child.” I rolled my eyes. “Fuckin’ hicks.” It felt good to call them that. It really did.

“S’fucked up Guilty.”

“Yeah, well…” I let out a long sigh. I could see my breath hang in the air as I did. I love being able to see my breath, it’s so fun. Sometimes as a kid I would spend hours at a time outside just watching my breath float away, pretending I was a dragon or something.

Who am I kidding? I still do it.

I swallowed as I prepared to breach a subject I really didn’t want to. “So… how’s Ms. Smile?” I knew at some point during this visit I was going to have to ask about her. I figured I should just get it out of the way and forget about it.

“’Ms. Smile?’ Since when do you call her that?” Crook seemed somewhat taken aback, which I was kind of expecting.

“’Mama’ just doesn’t seem… appropriate anymore.” I explained.

“Shit, Guilty, the mare practically raised us.” Crook’s brow furrowed. “What the fuck happened between you two?”

“I don’ wanna fuckin’ talk about it.” For all the positive energy Crook carries around with him, he sure knows how to dig up unpleasant memories.

“Why? You fuck her?” Oh Crook. Ever Blunt.

“For fuck’s sa-… No… I didn’t fuck her, Crook.” I could hardly believe he’d actually just asked that. Cherry Smile was like a mother to us. That would just be… *shudder*

I don’t even want to imagine that.

“Then what happened? What the fuck were you doin’ for her at the end there?” If nothing else he was persistent.

“Why don’t you ask her?” I was deflecting.

“I did. She said to ask you.” That sounded like Ms. Smile, alright.

“Look, can we not do this right n-”

“Since when do you keep secrets from me, huh?” He was upset, but… not angry.

“It’s just… I don’t wanna think about it, Crook, and I want to talk about it even less. Aright?” That seemed to satisfy him for the time being. Crook might be a forceful son of a bitch, but he knows when to back off.

Sometimes.

Ponyville wasn’t too lively that morning. The winter can have that effect. Windows were closed up tight. Chimneys were spewing smoke into the sky. Most ponies were tucked away inside, relishing in the warmth of their fires, and in the company of their loved ones. The streets had been plowed, thankfully, so we were no longer trudging through snow.

Now, though they were markedly less crowded, the streets of Ponyville were not empty. Citizens still walked the streets, wrapped up tight in winter clothing, going about their daily business. I still received the occasional nervous glance from a blushing client, overheard a whisper or two. Even in Winter, Ponyville is still Ponyville it would seem. And even in coats and scarves, mares are still mares, a fact Crook was always eager to thoroughly investigate.

He spent the larger part of or little trip to the library ogling mares, throwing them suggestive glances. More than a few of them blushed. Crook has always been good at flirting. He’s sort of naturally talented at making mares want him.

“Damn, Guilty… you are a lucky lucky escort, all these pretty girls to yourself.” Crook winked at a passing mare, who giggled despite herself.

I shook my head. “They’re not all clients Crook.”

“Give it time.” He assured me. “Before long, you won’t be able to walk down the street without being recognized.”

I face-hooved.

“So where’re we headed anyway? What does your little backwater burg have to offer? Aside from all the tail, I mean.” Crook seemed to be looking around for anything interesting, only to be disappointed. Beautiful though it may be, Ponyville really isn’t… exciting.

“We’re going to the library.” I answered.

“Lame.”

I rolled my eyes. “I gotta couple things to take care of. I need this book on-”

“Lame.”

I laughed despite myself. “I’m gonna fuckin’ smack you.”

Crook snorted. “What? Books are fuckin’ lame.”

I sighed contentedly. I love his banter. “You’re such a meathead.”

He gave me a jab in the shoulder for that.

The two of us continued down the streets of the town until, at last, we reached the impossible tree-building that was Ponyville’s Library. “Well… at least it’s cool lookin’.” Crook admitted.

“Yeah, the librarian’s not bad lookin’ either.” Crook perked up. “Oh, that got your attention.”

“Books might be lame, Guilty. But booky girls?” He trailed off and gave me a knowing look.

I would say Crook has a thing for nerdy girls, but to be honest he has a thing for everything. Crook likes mares. All of them.

I knocked on the library’s little front door. ‘Hopefully this won’t be too painful. Apologize to Spike, find that book again, figure out how to bed Zecora, and hopefully avoid any discussion of Twilight’s boyfriend. All should be well.’

I heard the pitter patter of dragon… paws(?)… scampering towards the door. ‘I’m forgetting something…’ The door opened with a creak. ‘Definitely something I should’ve done…’ Behind the threshold stood Spike, ready to welcome us into the library. ‘Oh shit I didn’t warn Crook there was-’

“A fucking dragon?!” Crook stared wide-eyed at the two feet of purple scales standing before us.

An awkward moment hung in the air while Spike just stared at Crook for a moment. Eventually he directed his attention to me. “Friend of yours?”

I scratched at me neck nervously. “Yeah… sorry about that. Crook, this is Spike. He’s the librarian’s assistant.”

“Guilty... he’s a dragon.” Crook had a big dumb smile on his face. He was excited, and understandably so. Dragons are just sort of legendary. Before Spike, I’d never actually met a dragon. Thinking back, I guess I was sort of surprised myself.

“Yes yes.” I turned my attention to the baffled dragon in the doorway. "Hi… Spike, right?” I didn’t actually need to ask; I remembered his name. It just seemed appropriate.

“Yeah… I uh… I don’t think I ever got your name.” He definitely remembered me, but he didn’t seem… upset… scared… angry… ashamed… anything. I was expecting some sort of tension or awkwardness, but he was honestly acting like nothing was wrong.

‘*Sigh*… kids are never going to make sense to me.’

“Oh, I’m Guilty and my excitable friend here is Crook.” This was weird. I had come here to apologize, but it was beginning to look like he wasn’t really expecting one. I wasn’t really sure what to do with this situation. ‘Should I apologize and look like a nutjob? Or should I just finish reading the book and let my guilt slowly eat away at me. Decisions decisions.’ I placed my ludicrous inner turmoil aside. “May we come in?”

“Sure, the library’s open and all.” He stood aside for us to enter. “Twilight’s not available, though.” he said as we entered.

“Who’s Twilight?” asked Crook.

“The librarian.” I answered. Crook began to sulk. He’d been looking forward to an eye-full.

“So… you want me to grab that book again?” inquired Spike.

“Oh, uh… yeah, actually. You don’t mind?” I was kind of distracted; I was trying to figure out how to work my apology into conversation as casually as possible.

“No prob. Lemme just grab it.” Spike ran off and I decided to follow him, best to do this like a bandage, just rip it off. Crook apparently decided to follow me, as well.

“So hey… uh… Spike?” ‘Just get it out of the way, Guilty’

“Hmm?” he said, as he began to peruse one of the shelves.

‘Just DO it.’ “Sorry I yelled at you last time I was here.” ‘There. Over. Done. Apology Completed. See? That wasn’t so bad.’

“Aaaah, don’t sweat it. You were upset; I understand.” I raised a brow. I hadn’t been expecting such a mature response.

“Oh… well… I’m glad you see it that way.” ‘Seriously, it was that easy?’

“Mmhmm. Here’s your book.” He pulled a familiar weathered tome from the shelf.

“What’s that?” asked Crook.

“Just something that should help me ‘get to know’ a local Zebra.” I couldn’t help but grin at the thought of “getting to know” Zecora. Crook punched me in the shoulder and grinned wickedly while Spike, who seemingly remained oblivious of my innuendo, handed me the book.

“So just like last time, you can read it here, but you can’t check it out. Don’t try running off with it like last time. Hehehe,” said Spike before he scampered off, and returned to his duties. He was even joking about it. What was with this kid? In some ways he was so grown up, but he was still definitely a child.

Whatever the case, I hunkered down at a nearby desk and tried to find my place in the book again. Before I even began, Crook was airing complaints. “You said there was a pretty librarian, Guilty.”

I shrugged. “I didn’t know she’d be busy. Find a book, entertain yourself for Luna’s sake.”

He snorted. “Fuck that.” He sighed heavily. “How long is this shit gonna be? I thought you were showing me what this town has to offer.”

‘I kind of am, there’s not much to show.’ He was making research impossible. I needed to distract him. “Why don’t you talk to the dragon, Crook? Go find out if he can breathe fire or something.” That excitement of his reared its head again, and without a word he rushed off. After that I actually managed to find what I was looking for. It was long and wordy, so I’ll paraphrase

As it turns out, Zecora is something called a shaman, or in training to be one. What that apparently means is she has spent years mastering the arts of Zebra Magic. Now, I understand less about magic than I do about Zebra culture, but apparently this is a big deal. The book went on to say that for a shaman to complete their training they must go on some kind of ‘pilgrimage.’ The specifics were vague, but I think that maybe Everfree Forest was the destination for that pilgrimage.

Here’s the fucking kicker, though. During their training, shamans are to “Abstain from the pleasures of the flesh.” Needless to say, I was disappointed. I’d been cock-blocked by a book… kind of.

“Fucking shit.” I muttered. I slammed the book with spiteful malice.

“Hey! Careful with that; it’s an antique!” Came a chiding voice from behind me.

I spun around. Staring daggers at me was Ponyville’s lavender librarian. “…Sorry…” was all I could manage while under her barbed gaze. I swallowed. Twilight was mad at me. I sort of froze. I don’t do so well when clients are mad. I was half expecting her to smack me with that look she was giving me.

Instead she recognized me and immediately blanched. Talk about a mood swing. “O-o-oh… u-um… hello there, uh… sir.”

‘Is that her idea of non-chalant?’

I instinctively offered a comforting smile. “Relax, Twilight. Breathe.”

“Y-yeah… sorry… you just kind of… surprised me.” She began to blush. I forgot how much she could blush.

“It happens all the time. Don’t sweat it.” I unconsciously began to treat this as a session. I seamlessly fell into character. “And I’m sorry about the book. I just… didn’t agree with what I was reading.”

“I-it’s okay. I’m just… I didn’t mean to snap.” Her ears fell and she looked down ashamedly.

“Hey, I deserved it. It’s an old book and I wasn’t showing it its due respect.” I reassured her.

She looked up at me and smiled despite herself.

‘Her eyes are red and puffy. She’s been crying.’

If I hadn’t let myself fall into full on escort mode, I might have let it slide. But things being as they were, the moment I noticed I immediately said something.

In retrospect that was kind of stupid considering I’d been hoping to avoid a discussion about her boyfriend.

“Is something wrong?” Concerned expression. Earnest Voice. Comforting hoof on shoulder. I didn’t really need to ask, of course, gossip had told me enough to know what was going on.

“N-no. I’m okay. I’m just…” she trailed off. “Were you done with that?” She indicated the source of my recent disappointment.

“Uhh, yes actually. I… found what I was looking for.” Her magic scooped up the book and delicately slid it back into its shelf… all the way across the room. I let out a low whistle. “That’s some range you have. You weren’t kidding about your special talent.” I complimented.

She grinned timidly. “You remembered that?”

“Of course. Why wouldn’t I? It was only months ago.” I joked.

She laughed. It sounded strained, but only slightly.

“So how are you Twilight?” I motioned for her to sit with me, and she obliged. We may have been in public, but the place was empty so I risked a little ‘shop talk’. “It’s been a long time.”

“Yeah, I guess it kinda has.” She briefly scanned the library floor. “Did you see Spike when you came in?”

“Yeah, he let me in.” I answered.

“Do you know where he is?” She seemed nervous; probably worried that he would walk in on some unsavory conversation.

“My friend is probably talking his ear off. He seemed interested in learning a bit about dragons.” ‘To say the least.’

“Oh… good.” Her head fell, and she began to stare at the desk.

And then came the sobbing.

“Hey hey hey, what’s the matter?” I asked.

Twilight hurried to her hooves. “S-sorry *sniff*… I *ahem*… I didn’t mean to… *sniff*… I’m sorry.” She began to trot away.

“Whoa, where are you going?” I moved to follow her.

“I… *sniff*… I-I didn’t mean to…” She sounded so fragile; she was about to completely burst into tears. She began to rush toward a door at the far end of the floor.

I almost followed her. It took me a little while to realize that it wasn’t really my place to be helping her. I’m not really her friend, I’m just her Escort. If Twilight wants to talk to me she can always make an appointment.

Still, I can’t help but feel like a jerk. It sort of seems like I’m trying to turn Twilight’s woes into a quick buck. It’s like I’m ignoring her now, so that I can help her when it can profit me.

I’m not trying to take advantage of my position, it’s just that… an appointment is really the only context in which I can do help her. Scratch that; that’s the only context in which it’s appropriate to help her.

At the same time, though, it’s… tough for me. I want to help everypony I can; I’m good at helping ponies with this kind of thing.

The argument to this is age old: If I give away what I have for free, why would anypony feel like paying for it? Now, cynical as that sounds, it is a valid point. If I go around helping everypony with their stress, they’ll never need to pay me a visit.

It just makes me feel so… greedy. I feel like I’m withholding relief from ponies who need it.

I know that’s not what I’m doing, it’s just…

It’s frustrating at times.

Is this what they call a Celestia Complex?

*Sigh* I do actually hope that Twilight does stop by. I’d love to be able to help her with what’s ailing her.

Anyways…

So off Twilight ran, her shame and grief pushing her into some dark corner of her home. For a moment I just stood like a statue in the middle of the main floor, watching the door through which she escaped. “Fuck…”

Crook’s voice sounded behind me. “What happened? I heard a door slam.” He trotted in with Spike, who was, for some reason, on his back.

“Was it Twilight?” asked the dragon.

I nodded. “Is she okay?”

“Yeeeaaaaah not so much. Her and her ‘boyfriend’ had a fight or something. I think they sort of… broke up.” Spike explained. I’d figured as much. “Either way, she’s not really talking to me about it.”

“Hey, don’t take it personally ki- Spike. I don’t think she really wants to talk to anypony about it.” I almost called him kid again.

“Yeah, yeah…” He stared absently at the floor.

Crook decided to chime in. “So, you all set?” He motioned for Spike to hop off, which he promptly did.

“Pretty much. You good to go?”

“Yeah, S’get the fuck outta here.” Spike couldn’t help but to cover his ears at the word ‘fuck.’ “See you later Dragon dude.” Crook extended him a hoof.

Spike took his paws off his ears and met Crook in a hoofshake… err… Pawshake. Clawshake?

Whatever.

I bid Spike a quick farewell, and the two of us took our leave of Ponyville’s library. “You find what you were lookin’ for?” Crook asked.

“Yes… unfortunately.” I grunted.

“Unfortunately?” Mimicked Crook. “So you don’t get to fuck this Zebra?”

“Looks like no.” I took a quick look around. It was now afternoon and the streets of Ponyville were getting a little more full. “So, what did you and the kid talk about?” I spent a fair amount of time on that tome. Crook and Spike must’ve found something to talk about.

“A fuckton, actually. Oh, by the way, he can breathe fire. It’s crazy.” Said Crook giddily.

“Yeah?” I was half listening. I was trying to figure out which way to head next.

“Yeah, it’s like… mail breath.”

I stopped and turned to him as I tried to find a rational concept to put behind his words. I failed to do so. “…What?” I threw him a look like he was crazy. What the fuck could he possibly mean by that?

“His breath, it’s like… magic or… somethin’. If he burns up a scroll or anything, it gets sent to Princess Celestia.” He casually explained.

“Wait… Celestia?” I was having trouble believing that.

“Yeah, Spike said that that Twilight girl, is the Princess’s personal protégé.” Crook smirked. “Apparently he sends letters to her all the time.”

If I hadn’t already stopped in my tracks I would’ve again. My blood ran cold. ‘Well I need to get going, I have a letter to write.’ That’s what she said. That’s what Twilight said at the end of our session.

There’s… there’s no way. She wouldn’t tell the Princess of the fucking nation about a pseudo-sexual exploit with a male escort…

…right?

I sturdy hoof shook me. “Hey Guilty… y’aright?” I’d sort of spaced out. The implications of Twilight’s words were… unsettling.

I shook my head to clear it. “Yeah I’m just…” My stomach rumbled audibly. “…hungry apparently. You?”

“Fuck yeah. Starving. Good food around here?”

“I dunno; there’s a couple places. If you feel like not caring, we could just say ‘fuck it’ and have pastries for lunch.”

Crook grinned. “I’m lovin’ the hedonism, Guilty.” I laughed, and the two of us made out way to Pinkie’s Bakery.

Wait. Not Pinkie’s. She just works there. Damn it. I always do that.

As we walked Crook continued to tell me all about his talk with Spike. It sounded like Crook had asked him every question he could think of. He can’t fly yet. He eats gemstones. He’s fireproof. He has a pet phoenix chick apparently, which is pretty cool. He has a crush on Rarity, of all ponies.

Oh and here’s something. He’s sixteen. That just blew my mind. I mean, if I think about it, it makes sense. Dragons live for ages. Of course they’d be kids for a long time. It sort of explains why he’s so tough to read. He hasn’t physically matured, but he’s still had plenty of life experience. He’s in a part of his development that ponies don’t really have. Fucking trippy. It certainly makes him interesting.

Not that he has any trouble with that. He’s a fucking Dragon.

Having Crook with me in town was actually fairly nice. He’s a good distraction; his constant conversation kept my attention away from the stares and whispers. It was almost like I was back in Manehattan. Just me and Crook. Nopony else mattered. All the anxiety and stress and worry and fear of walking through the streets almost didn’t exist. We were just… hanging out. It felt good.

When we entered the bakery we were greeted by two things: the smell of freshly baked sweets, and a long-ass line.

“Fuuuuck” Crook immediately groaned.

“Don’t worry, the food’s real good here.” I assured him. “It’ll be worth the wait.”

“It better be.” He mock-threatened, before smirking and throwing me yet another punch in the shoulder.

As a matter of fact, he hit me so much while he was here, my shoulder still hurts.

Ah, friendship.

The two of us queued up. The mare right in front of us was a client: Marigold. She really likes it when I give her head. Half of her sessions don’t even end in real sex, which is just fine in my book. She didn’t seem to take notice of me.

I was keeping a wary eye out for Applejack. I’d hate to have a repeat of the last time I was in the bakery.

When I got to the front, Pinkie was at the register. She was her usual bouncy self, just a fuzzy pink ball of energy. The first thing she did at the sight of me was smile from ear to ear. “Oh my gosh, hi Guilty! I haven’t seen you in forever! How have you been? Are you hungry? What can I get you?”

Crook just stared wide eyed at Pinkie’s spirited display.

I chuckled. I’d forgotten just how hyper this mare could be. “Hi Pinkie. I’ve been well, thanks for asking. Could I get two slices of…” I quickly scanned for something good looking. “…carrot cake?”

“Two slices? Somepony must be hungry.” Pinkie giggled as she began to ring me up.

“Actually one is for my friend, here.” I indicated Crook, who offered a friendly smile.

Pinkie directed her attention to him, before letting out a positively enormous gasp. “*GAAAAAAAAAAASP* Oh my goodness! You’re Guilty’s friend! What’s your name? Are you from Manehattan? How did you meet Guilty? Are you an escort too? Do you like parties? I have so many questions!” She had practically jumped over the counter by the time she finished ranting.

Crook let out a low whistle. “Wow, Guilty. You didn’t tell me the girl who worked here was such a cutie pie.” That was just like Crook. He’ll take any opportunity to flirt.

“Don’t be silly,” said Pinkie with a wave of the hoof. “I’m not a cutie pie; I’m a Pinkie Pie.” She laughed at her own joke and extended a hoof to Crook.

“Crook.” He said simply. A sly smile crept onto his face as he took her hoof. It was a look I recognized all too well. He wanted to fuck Pinkie Pie. “Nice to meet you, Pinkie.” Crook’s smart about flirting; he knows not to lay it on too thick. He’s just attentive and interested and behaves like a gentlecolt.

“Hiya, Crook! What can I get you? A scone? A cupcake? Some fresh baked cookies? Oh I know, how about an apple fritter? An apple tart? Apple dumplings? Apple P-”

“Actually, I think my friend here already ordered for me.” He vaguely gestured in my direction.

“Oh yeah! Carrot Cake! I’m on it!” Pinkie gave a quick salute and served up the cake. “Here ya go!” She happily handed us each a big slice of carrot cake on a little paper plate. I thanked her as Crook and I headed to grab a seat, leaving her to deal with her next customers.

She’s very nice to all of her customers. She said once that she considers me a friend, but I think she considers everypony a friend. Still, I’m no less grateful for that friendship. I could use a few more friends, probably.

“So I’m definitely asking her out.” Proclaimed Crook as we sat at an available table. “Any advice? What do we know about little miss baker here?” That was just like him. Crook could just… never get enough plot. He may not have taken clients as often as I did, but he almost always had a mare to share a bed with if he really wanted. He would just… pick up mares without trying, take them home, and fuck them stupid.

I never really saw the point to it back then. If I ever particularly desired sex, (not that I ever really did) I could just grab a client. I’d get laid and paid.

That rhyme was unintentional.

Crook loved his job, but he’d rather just pick up a mare given the choice. I asked him once why he bothered, and I just replied that it was more fun.

Despite that, he never really had a serious relationship. He’d have little flings all over the place, but never really had a real girlfriend. In all honesty, I think he doesn’t really want one.

Still, I had to think about what I could share with Crook about Pinkie. I mean, Crook and I would swap notes about mutual clients all the time, but… it somehow didn’t feel appropriate, I mean… they were just clients and we were just escorts…

None of those clients were my friends.

It just didn’t… it didn’t feel right with Pinkie, especially considering how shy she was about the food-play
.

So I tried to think of something I could get away with; I decided on something fairly harmless. “Last I heard she was looking for something serious, so… make sure she knows you’re not in town that long.”

Crook clicked his tongue and furrowed his brow. “Geez, Guilty. No shit. I’m not stupid.” He huffed and bent down to take a bit of his cake. His eyes grew wide as the flavor hit his tongue. “Dis is guhd.” I took a bite myself. It was good. Damn good. Not full-on-pastry-related-erection-good, but still damn good.

Crook and I chatted briefly. I confessed that there wasn’t really much more to Ponyville aside from shopping. He inquired as to how I hadn’t killed myself yet. I told him about how I’d taken up hiking. He laughed at me. I told him to go fuck himself. He made a lewd joke at my expense. I called him a nasty name. He told me to suck his dick. I told him I didn’t want to choke to death. He laughed. I laughed. We had a good time.

Once we finished our cake Crook kept an eye on the line, looking for lull in customers, hoping to get some face time with Pinkie Pie. Without the distraction of Conversation, I once again started to notice how most of the other bakery-goers were very interested in their meals. I caught an odd stare from an older stallion. I heard somepony whisper the word ‘whore’ somewhere behind me.

Ah, Ponyville. What a charming little burg.

“Well, shit. If it ain’t Guilty Pleasure, actually out on the fuckin’ town. And look, he’s got a boyfriend. How sweet.” A familiar throaty voice mocked from behind me.

“Close Shave.” I said before spinning around to face my abusive barber. “Still alive, then?”

Close scoffed. “Don’t worry, I plan on outliving your dumb ass.” He nodded toward Crook. “So, who’s your ugly friend? He needs a haircut… so do you.” He pointed a threatening hoof at my mane. It wasn’t that long. Close is so uptight.

Crook, finally noticing that we had company, turned his attention back toward the two of us. “Who’s this asshole?” he asked in a deliberately dickish fashion.

“Watch your fuckin’ language, kid.” Warned Close.

“Make me, ya’ fuckin’ fossil.” Baited Crook.

Close scowled. “Son, you are walkin’ down a road you reeeaaally don’t want to.” He took a step towards Crook, and pushed his face right up into his.

Crook is not one to back down from a challenge. He adopted a low stance and pushed right back. “Watch where you put that horn.”

The tension was getting pretty thick. Ponies were starting to stare at the two large white stallions standing off on the bakery floor. I decided to defuse the situation.

I rolled my eyes exaggeratedly. “Oh for Celestia’s sake. Just kiss already!”

Crook immediately burst into laughter. “*Snnnrk* For fuck’s sake, Guilty… that one always gets me.” Close just looked confused as his would be opponent cast off all sign of aggression at the drop of a hat.

Introductions were in order. “Crook, this is Close Shave, he runs a barbershop in town. “Close is this is Crook, he and I came up together.” They shook hooves.

There were a lot of hoofshakes that day now that I think about it.

“Had you goin’ there, didn’t I?” Crook asked to Close.

“Boy, I’ll say.” Close released his grip. “I was about to mop the floor with you, kid.”

“As if. You woulda thrown a punch and broken a hip or some shit.”

These two were like a perfect storm of angry Manehattanite. It was sort of beautiful. The machismo was thick and the accents were thicker. It felt like home again. It’s just not Manehattan if two angry assholes aren’t yelling at eachother. The best part was that they both had great big smiles on their faces. It probably was just as nostalgic for Close as it was for me, and as for Crook… Crook just loves to fight.

While the two continued to verbally bitch slap each other, I noticed that the line had completely vanished. “Crook.” I called.

“What?” he responded, annoyed.

I just nodded toward Pinkie.

He caught my meaning. “Shit. Thanks.” He quickly trotted over to Pinkie’s register and grabbed her attention.

Close watched on as Crook began to work his magic. “You know when I walked in here and saw that asshole: the stoic expression, the white coat, the athletic build. I thought he might be a Royal Guard… and then he opened his fuckin’ mouth.” He chuckled. “Fuck me, does that kid has a mouth on him.” He was still smiling.

I nodded. “Yeah, he really does.” Crook was already making Pinkie blush. “So how’s life, Close? What brings you to the bakery?”

He sat beside, harrumphing as he did. “Life’s good. The wife wanted me to pick up some tarts. We got company over.”

“So why aren’t you in line?” I asked.

“I’ll let’cher friend talk to the girly. I can spare a little time.” He smirked as Pinkie Pie grinned happily at Crook.

“How very considerate of you. Who are you and what have you done with Close?” I jabbed.

“Cute kid… real fuckin’ cute.” He snorted at me. “So what about you? What’re you up to? How’s that girlfriend of yours?”

I immediately buried my face in a hoof. “How many times do I have to say it, Close? Not a girlfriend, just a platonic female friend.”

“And how many times do I gotta tell you there’s no such thing?” He shook his head dismissively.

I rolled my eyes. “Anyways, she’s fine I guess. It’s been almost a week since I saw her.”

He frowned at me. “Tsk Tsk, Guilty, that’s no way for a stallion to treat his mare.” He teased.

I groaned. “I hate you so much.”

“Yet you’d be lost without me.” He smirked. He was loving torturing me. “Seriously, though. How’s life kid?”

“Life’s fine. Business is good. Friend’s in town. I don’t really have the equipment to go hiking in the snow, so none of that for a while.” I explain.

“Oh yeah. I forgot all about your bullshit obsession with hiking.” He chuckled. “You’re such a fuckin-”

“Guess who has a date tonight!” Crook noisily interrupted.

Close’s expression jumped from angry to Impressed. “Geez, kid, you work fast.” He remarked.

“What can I say, I’m quite the catch.” Crook smiled. He has such a shit-eating grin at times.

“Looks who thinks he’s Celestia’s gift to mares.” Jabbed Close.

“What’s yer damage, pal? I got a way with the ladies, you don’t have to be jealous.” Taunted Crook.

“Who’s jealous? I got a smokin’ wife waitin’ fer me… Oh shit.” Close quickly left the table and made his way to the register.

“Poor old dude, forgot why he was even here. Must be gettin’ soft in the head.” He turned his attention back to me. “So, you mind if I bring her back to your place?”

I shrugged. “Well considering the fact that if I say yes, I think you’re going to do it anyways, I’m gonna go ahead and say no, I don’t mind.” I didn’t doubt that he would succeed in seducing Pinkie, he’s good at that.

Shoulder Punch. “Thanks, Guilty, You’re a pal. Mind if I use all that shit you got stashed away in those chests?”

I shrugged again. “Go for it.” I made a mental note to wash everything in my chests, just in case.

“What would I do without you?” He crooned.

Across the floor I saw Close practically running out of the Bakery. “I expect to see both your asses in my chair tomorrow!” He called.

Crook just looked befuddled. “What the fuck is he talking about?”

“Barbershop, remember?” I reminded him.

“What’s wrong with my mane?!” He ran a hoof through his locks. “This thing is beautiful.” He said in a very self-satisfied manner.

“Yes, you’re very pretty. You ready to help me carry a ton of food?” I asked

“Sure, let’s go.” So we left. Crook winked at Pinkie as we left. She blushed and giggled. Close was right, he does work fast.

So we made our way down to Barnyard Bargains to pick up some amenities. There was no market that day, unfortunately, so I couldn’t pick up any fresh produce. Still, the Grocery store would keep me alive for a while.

Crook continued to wink at every mare that passed by as we treaded down the streets of Ponyville once more. “Don’t you already have a date tonight?” I asked him. I didn’t need to do that, I suppose. I could guess what his answer would be.

“I don’t have a date for tomorrow night.” He responded.

“You’re such a shmuck, Crook.” As I insulted my oldest and dearest friend, we arrived at Barnyard Bargains. When we walked inside we were hit by a wave of freezing air. We stepped into a fucking icebox of a store. “Guilty, my balls just jumped into my lungs! What the fuck?!” It was colder in there than it was outside.

Our knees began to knock and our teeth began to chatter. “F-fuck, I dunno. Let’s just g-grab what I need and g-get out of here.” It was awful. Near as I could figure the freezers and such were still on, but the heaters were out of commission. ‘Just remember, shivering burns calories.’ I reminded myself.

So we grabbed a cart and rushed our asses through the store. We kept our pace up to stay warm. The other shoppers seemed to have the same idea, everyone was shopping at an incredible pace. Food was flying off the shelves. I grabbed what I could: some frozen vegetables, some whole-wheat bread, a few cans of daisy soup, potato chips, whatever I could get my hooves on. Crook secured quite a few bottles of liquor, which rattled as I pushed the cart. It was fine, I could afford it. There was only one thing left to grab: Heaven’s gift to ponies, cereal.

One box.

A single box of Peanut Butter Crisp sat on the shelf. Somepony was eyeing it. ‘Do I risk making a total ass of myself to grab it? I could rush past her and snag it… but I’ll look like a total fucking tool.’ I debated my actions for only a moment. It was tempting, my stash was running low, and Peanut Butter Crisp is a veritable Delicacy.

In the end, I opted not to act like an absolute shit, and let her take the box.

‘Oh well, Guilty. There will be other days, with other cereals. Many a bowl awaits you in the future, and… wait, is that Derpy?’ My subconscious caught me off guard. Sure enough the mare that had just grabbed the last box was my favorite client. She was so wrapped up in coats and scarves I barely recognized her. “Hey! Derpy!” I called as I trotted over to her.

Her head spun around. When she saw me she grinned and waved. “Hey, Guilty!” She slowed her progress down the aisle so I could catch up.

“D-do you know why it’s s-so cold in here?” I asked.

She shook her head. “Nope. Lucky I dressed extra warm, huh?” She said, cheery as always. She really was dressed up, too. She had a big puffy coat, big thick sweatpants, a warm fuzzy scarf . To top it all off she had a cute little beanie, complete with pom-pom. “So, what’s up Guilty? Just shopping?”

“Yeah just g-grabbin’ a few things to keep me fed…” I responded.

She eyed my cart. “Throwing a party?” she asked. I followed her gaze to the massive amount of liquor sitting in my cart. I chuckled nervously, though I’m not sure why. “Hehe, no, my f-friend’s in town. He’s kind of a d-drinker.”

“Oh, okay.” There was a hint of something like disappointment in her eyes. It was brief. I only caught it because… well because I’m me. “Who’s you’re friend? Is he from Manehattan?” She asked. Any sign of what I’d noticed was already gone.

“Yeah he’s…” I turned around expecting to find Crook, somewhere behind me, but he was nowhere to be seen. “… p-probably flirting with somepony at the m-moment.”

Derpy chuckled. “Your friend sounds like Lyra. Oh! That reminds me. Lyra and Bon Bon said that they visited you. How did that go?”

In a brief spell of total and utter insanity I actually almost started talking about it. I had my mouth open and everything, totally ready to spill intimate details about clients that trusted me. It was so absent-minded of me. Needless to say, I chastised myself to no end later that evening.

I didn’t say anything, thank Celestia. I caught myself, mouth agape. Derpy looked eager for a story and I hated to disappoint her, but… I knew better. “S-sorry, Derpy, I can’t really t-talk about other clients like th-that.” It was so hard to say no to that smiling face of hers.

“Aaaw, too bad.” Her expression fell for a second before bouncing right back up. “I’m sure it was fun, though. Bon Bon says Lyra’s kind of crazy in bed.” Derpy said with a giggle. “But anyways, I think Lyra had some anxiety about Bon Bon being not having been with a stallion, so I told them about you.” She began to walk down the aisle once more, and motioned for me to follow.

Derpy’s little story had made me a bit curious about something, so I hazarded a question. “What w-were… What were th-their reactions? W-when you t-told them about me, I mean.” I’d asked Rarity about a few of the clients she’d referred to me at one point, but I was still curious about Derpy.

She giggled once more. “Hee hee. When I first mentioned that I knew about you, they asked how I knew.” She grabbed a jar of jam off of a shelf. “When I said I was a regular client, Lyra couldn’t stop laughing. Bon Bon was just stunned silent. You should have seen her face.”

I allowed myself to snicker at Derpy’s story. That sounded just like the two of them. “Well that’s good.” I said. “Better than them being upset at least.”

Derpy threw me a confused look. “Why would they be upset?”

I shrugged. “Well you never know who f-frowns upon my profession. Lots of ponies in town m-might’ve had a problem with me.”

I didn’t think that this would be news to her, but she looked absolutely mortified. “What?! Why?!” She may have been a little bit too enthusiastic; she was turning a few heads.

I was sort of amazed she didn’t know about this. I’d thought it would’ve been a big enough deal when I moved in. “Lots of ponies just t-take issue with… what I do. That’s why I don’t l-live in the town proper.” I cocked my head to the side. “You d-didn’t know about that?”

She was getting all worked up. “No! That’s terrible! Why do ponies not like what you do?! What’s wrong with sex?!”

That was, however, a question I have spent much time contemplating. “I’m not a hundred p-percent sure, Derpy. Some ponies think s-sex isn’t something you should be able to b-buy or sell. Some ponies th-think that my business has a corruptive influence on ch-children. Some ponies just see me as some seedy whore, I guess.”

“But… but it’s not a crime, right? If it was wrong it would be illegal!” She asserted with a stamp of her hoof. She was actually quite adorable, arguing with ponies that weren’t even part of the conversation.

I saw some cherries that looked pretty good and tossed them into my cart. “Well, you are correct, Derpy. Prostitution is not a crime. But that doesn’t mean everypony is happy about it.”

Derpy mulled over the facts in her head for a moment. Even when concentrating her face is adorable. Eventually she came to a conclusion. “That’s dumb!” She said definitively. I snorted in laughter despite myself. Her delivery was priceless. “No, I’m serious. That’s dumb. That’s like me saying all the onion farmers have to live outside town just ‘cause I don’t like onions, and that’s dumb!” She stamped her hoof again. “I’m gonna talk to the mayor about this!”

That was the last thing I wanted. Besides, the mayor was already aware of my situation. “Derpy, please don’t. I don’t want to make trouble.” I pleaded. I took a quick look around, and we had attracted quite a crowd. Derpy’s rant had gotten rather loud. “Come on, let’s just check out. We can look for my friend, I’ll introduce you.” Derpy reluctantly accepted my offer, and the two of us went to the register.

I didn’t recognize the stallion manning the check-out, but he sure recognized me. He stammered and stared and was just sort of awkward through the whole ordeal. Derpy noticed this as well, and gave him a stink-eye. I don’t think he really deserved that, I guess Derpy felt otherwise. After I got all of my food I did a quick run down the aisles to try and find Crook, but he wasn’t there. After Derpy checked out, the two of us left the store.

As we walked out, we noticed two ponies talking. I recognized both of them.

‘Oh hey look, there’s Crook. Oh hey look, he found another mare to hit on...’

‘Oh fuck me… that’s Applejack.’

Okay, lunch time, I’ll write more after some soup or something.

Friends

Chapter 12

Friends

Fuck, it’s cold… that soup hit the spot.

Anyways, where was I?

Oh, right… Applejack.

So yeah…

Crook was hitting on Applejack. I didn’t even have to hear him to know he was flirting. His body language. Her blush. His confident smirk. Yup, definitely flirting.

I almost ran away. I almost just turned right around and hid in the store. I could’ve walked around the store for another half-hour and waited for Applejack to leave. Hell, I could’ve gone anywhere at all, and Crook would’ve found me eventually. I could’ve avoided this whole fucking awkward terrible unfortunate situation in its entirety.

Unfortunately, I just sort of... froze up. Everything happened so slowly from my point of view. I watched Crook flirt for a moment. I watched Crook notice my presence, and I watched Applejack turn her head to follow his gaze. Now, I’d never actually seen it before, but Applejack has a nice smile. I saw it right there, only for a second. For an instant she was as happy as could be.

And then her expression just turned right into a scowl. “Son of a-” she completely turned her body and started fucking marching toward me. “What in Sam Hill are you doin’ here?” she asked threateningly.

I didn’t respond. I tried to ignore it. I just wanted to walk past her and pretend she wasn’t there. I didn’t want a fight like last time. I didn’t want to be a snarky jackass. I just wanted to go, so I just started to walk past her.

“What’s going on?” Derpy’s voice asked from behind me. I wished desperately that she would not have to bear witness to this shit show. I wanted to distance myself from her as quickly as possible. I didn’t want her to be a part of this.

Applejack was the one to answer her. “Don’t y’all worry, hun. Ah’m just takin’ care a’ some business with this here stud. You can just run along.”

‘So… stud has become her default insult, has it? Lovely.’

Crook’s eyes were wide at this point. Some sort of morbid sense of humor had put a smile on his face. He could hardly believe what was happening, and it was cracking him up.

I just moved to walk away again. “Not so fast!” Applejack shifted herself right into my path. She’s never actually tried to stop me before; my little stunt at the Bakery was coming back to bite me in the ass. “Where d’yall think yer goin’?”

I sighed, defeated. This was fucking awful. Much to my dismay, I was actually going to have to engage her. “Home,” I responded tersely.

She snorted in my direction. “Good, the sooner y’all ‘re outside Ponyville the better.” She stayed parked right in my path. I just sighed and started to walk around her. Hopefully that would be the end of this little-

Once more from behind me I heard Derpy. This time, however, she was shouting. “Applejack!” I almost didn’t recognize her voice. I’d never heard it… angry before. Applejack was seemingly equally dumbfounded.

‘Holy fuck, is she… is she standing up for me?’ I couldn’t believe it. No really, I could not believe my ears. I’d long since resigned myself to the belief that nopony in Ponyville would publicly stand up for me. Defeatist as that may sound, it had been two years since I moved here, and it hadn’t happened yet. Then again, Derpy was a new factor in this particular equation. She’d never been exposed to Applejack’s bullshit before.

But at the same time I truly wished she wouldn’t. I was just so sure that this would make Derpy look bad. I wanted her to stop. I didn’t want her to be “that mare that stood up for the whore” or whatever. I didn’t want this to hurt her. There had to be a way out of this. Surely it wasn’t too late to just take everything back, right?

If only.

While my brain scrambled, Applejack was still trying to figure out what was happening. “Derpy, what’re y’all…”

She marched right up to Applejack and pointed a hoof at her. “You’re being a bully!” It was actually sort of adorable, her confronting Applejack. It brought a smile to my face… Crook’s as well. He was eating this shit up.

Applejack sighed. “Hun, I don’t think y’all understand what’s goin’ on here.” I was watching her as she said that, by which I of course mean I was reading her. I noticed something that almost made my jaw drop. Applejack showed no signs of guilt or regret. She spoke to Derpy without hesitation for her actions, and without fear. No signs that she thought that anything she was doing was taboo or to be frowned upon. She actually thought that once she explained the situation to Derpy that she’d understand.

It’s kind of scary to think about but… Applejack genuinely thinks that driving me out of town is the right thing to do. She doesn’t think she’s being vindictive or just plain selfish in her hatred of me; she’s just… following her moral compass.

I might be reaching with this one, but… I dunno… that’s what it seemed like.

It’s fucking worrying is what it is. But anyways…

“What’s not to understand?!” Derpy cried. “You’re being mean to my friend!”

I swallowed audibly. This whole ordeal was accelerating. I needed an out. I needed to calm both of these mares down and get the fuck out of here before too many ponies showed up. I needed this whole situation to end before something happened.

“Now, whadd’re y’all tryin’ ta-... Oh Derpy, don’t tell me… y’all haven’t been givin’ him yer money have you?” She sounded so concerned. She was already making out Derpy to be some sort of victim of my wicked machinations. This was about to blow up in my face.

“Of course I do. I’m not going to not pay him,” said Derpy as she shrugged. I’m sure to her it seemed like a harmless confession, but I could see the gears turning in Applejack’s head.

“You…” Her head slowly turned to me, her teeth gritting, her brow furrowed. She was the very picture of anger. “You… no good… low down… rotten…” She racked her brain trying to think of a sufficiently nasty name to call me. Failing, she continued her rant. “What gives you the right to… to swindle this here mare outta her hard-earned bits, huh?” She took a threatening step towards me. “I bet you didn’t know she had a daughter at home, didja? That she’s raisin’ that filly all by herself, and she don’t need no… no dang seducer makin’ her life any harder.” She snorted angrily in my direction. “Just ‘cause she’s a few apples short of a bushel, don’t mean you can just march on into her life… into her home and… take whatever y’all want from her!” She was seething.

I cocked an eyebrow at something she’d said. ‘Hang on… Did she just say that Derpy-?’

“Wait… what?” The question came just above a whisper, but it silenced Applejack immediately. I wasn’t even sure who had asked it. I looked to Crook, but he was still giggling to himself, silently relishing the guilty look growing on Applejack’s face. I scanned the ever-growing crowd for the culprit, only to find everyone’s gaze directed at Derpy. And then I saw why.

The level of hurt and rage on her face was just… it didn’t suit her. She looked like she was somewhere between crying and punching someone. “I… I don’t… Applejack… how could you… *sniff* How could you even say that?”

“Oh, Derpy, y’all gotta know I didn’t mean…” She sighed heavily. “Look… it ain’t… exactly a secret that y’ain’t the sharpest knife in the-” *SMACK!*

My eyes shot wide open. I could not fucking believe what had just happened. Derpy had slugged her. Derpy had flown straight at Applejack and punched her square in the face! Fucking shit! The crowd let out a collective gasp.

Applejack didn’t even react, she just stared at the hat that had been knocked from her head. For several seconds she just stood there while everybody held their breath. Eventually she took up her Stetson and began to knock the snow off of it. “Okay… Ah probably deserved th-”

“I am not stupid!” Derpy shouted. No, scratch that.. shouted isn’t a good enough word by far. Declared. That’s more like it.

Applejack was struggling to keep ground. She desperately tried to shift the subject back to me. “Dang it, Derpy, I know that. I was just… Look, this here stallion… he ain’t a good pony. He’s-”

“Guilty’s my friend!” She was having none of Applejack’s shit. “And stop talking to me like I’m stupid!” She moved to throw another punch, but this time Applejack was ready. She held a hoof square in Derpy’s chest, keeping her safely out of reach. When Derpy’s punch fell short, she continued to swing hooves that would ultimately fail to reach their target. She was so unbelievably furious. It hardly seemed like it was actually Derpy doing all of this.

“Now, girl, I ain’t gonna let you slug me again so just… *grunt*… Now calm down… *nnf*… would y’all quit that?!” She punctuated her sentence with a firm push that thrust Derpy back a few feet. Derpy just fumed as Applejack adjusted her hat.

I had that same instinct again. That one that told me to turn and run while all the attention was on these two. I stayed this time, though. I didn’t run like I did with Spike. The thought of abandoning Derpy while she was sticking up for me… that was enough to keep me from running. I could never forgive myself for something like that.

Turns out, I’m a decent pony sometimes.

Once Applejack had dusted herself off she turned back to face Derpy. “Now I’m sorry I got ya so cross, Derpy, but that don’t mean Ah’m gonna let ya smack me around, all right?... Geez… you think you know a pony…” she grumbled.

“Yeah you could say that again!” cried Derpy. There was still anger building in her, if that was even possible.

‘Shit. If somepony doesn’t do something this is gonna come to blows again… Shit. that somepony’s gonna be me isn’t it. Shiiiiiit.’ Against my every instinct I decided put myself on the spot. I swallowed. There was a very good chance that this was going to end horribly. Almost definitely. Ninety-nine percent.

I cleared my throat. “Are we done?” All eyes on me: Derpy’s, Applejack’s, the crowd’s, all of them, fucking all of them. Why was I doing this? Dear Celestia, let it be over quickly.

Against all odds Applejack actually didn’t jump down my throat. She (mind-blowingly) nodded. “Yeah… we’re done.” She moved to leave, walking right past me. Once she reached me she stopped. “We’re still gonna have words, though. I promise you that.” And with that she shoved her way past me.

Now, being the picture of grace that I am, in my attempt to stay upright I actually managed to trip over my own hooves. Now… my timing here could’ve been better, since tripping right when I did gave the illusion that Applejack had actually knocked me on my ass.

And then Crook was mad.

I felt the small quake caused by his hooves as he barreled past me. “Hey!” he shouted. There was some anger in his voice, but honestly not enough for most ponies to notice.

I was still trying to right myself, so I failed to see Applejack’s face. “Oh, hey. Sorry y’all had to see that, big guy. With all the hubbub Ah forgot Ah was talkin’ to ya… Sorry ya had to see all that… I don’t suppose you still wanna grab a bite… do ya?” She sounded almost hopeful. Maybe desperate is a better word. She must’ve really liked the look of Crook. Not that I can blame her.

‘Whatever you do, Crook, don’t start something.’

“Hey, don’t worry about it.” he answered coolly. “I’m free tomorrow.”

‘Wait, what?’

“Oh! Well, uh… good… I guess… hehe.” I heard her swallow. “So… lunch? Ah know a nice little bakery around here.” I righted myself to see the goofy blush on Applejack’s face. “Sound like a plan?”

“Sure thing, I know the one. See you tomorrow.” He gave a dashing smile and the two said their goodbyes.

What the fuck was this? This was not a Crook move. This was calm, rational. Crook doesn’t let ponies who do shit to me just walk away. Not that I mind, doing that would’ve made things much worse. But still. Crook, taking a calculated and rational course of action… freaky.

Once Applejack was far out of sight he made his way over to me. I was brushing the snow out of my mane. “Y’alright Guilty?” he asked as he began knocking snow off of my jacket.

“Yeah, I just tripped.” He proceeded to give me a quick once-over, checking for scrapes and bruises.

Ever protective.

Still, I had some questions. “So what was that shit you pulled with Applejack?”

“Whaddaya mean?” he asked innocently.

“You know what I mean…”

Instead of answering he just gazed past me. “Guilty.” He indicated the area behind me. I turned to see Derpy, standing rigidly in the snow. Head sunk… eyes closed…

Sobbing.

“Oh fuck me.” Ponies were slowly slinking away from the show that the three of us had just put on, and most of them were trying not to notice the full grown mare who was slowly breaking into tears.

Fuckers.

My actions were unconscious; I jogged over to her side and lent her a comforting hoof. I was careful with my words. Didn’t want to upset her any more. “Derpy? You okay?”

She was mumbling to herself. Just standing there shaking her head, mumbling, I felt so sorry for her. This was my fault. This was all my fault. I should’ve just run from the start. I let this happen.

‘Hey, enough self-pity. Fucking help Derpy, would you?’

I snapped myself out of my micro-funk, and got my attention back where it need to be. “Hey, Derpy? Let’s get you outta here, yeah?” I shook her a little. I had to help her quickly, she looked positively pathetic. I bet she felt just as much.

She just continued to mumble. “I-I’m not stupid. I’m not f-fucking stupid.” Her head rose up and her gaze met mine. Her eyes were so red, she was going to burst any minute. She buried her face into my chest.

“I know, Derpy. I know you aren’t stupid.” She just continued to sob into my jacket. “You wanna get outta here?” She nodded. “Okay.” I gave her mane a comforting brush of the hoof. “Crook, let’s go. Grab the booze."

He wordlessly obliged, and the three of us made our way back to my home. Luckily for me, winter clothes once more kept me camouflaged amid the crowds of Ponyville. Nopony looked twice at the three ponies huddling together down the streets. My bulk and Crook's combined kept Derpy largely out of sight, for which I’m sure she was grateful.

She remained silent, even as we entered my still warm abode. I decided to take her into the bedroom, so she could lie down. Crook decided it would be a good time to unpack the groceries I’d procured.

Derpy just sort of collapsed face down onto the bed and curled up into a ball. This mare was going to cry, no two ways about it. Odds were she didn’t want me around for that, but it never hurts to check. “Can I get you anything?” She just shook her head. “Okay Derpy, I’m right outside if you need me.” And with that I took my leave.

“Geez… everybody’s fuckin’ cryin’ today,” Crook said as he took stock of my liquor. “*Tch* I forgot to grab Kahlua.”

“What the fuck do you need Kahlua for?” I wasn’t really in the mood for Crook’s antics.

“White rushin’s,” he responded simply before rustling through some more in the paper bags. “Oh wait… here it is. You got cream, right?”

I rubbed my temple. “Probably. I dunno.” I was getting a headache. I started unpacking the untouched, non-alcoholic groceries. “Check the fridge.”

Then the whole situation started to dawn on me. I’d brought Derpy into my home. I hadn’t even thought about it; she was crying, so I took her to a safe place. It made sense, I guess, but from the outside this might look like seduction. That’s not just me, right? I’d taken an emotionally fragile mare and talked her into coming home with me. Oh geez, I’d even taken her to the bedroom. For a moment I was worried I was turning into exactly what Applejack thought I was. This was weird. This was fucking weird.

‘Okay, Guilty calm down. You’re just… being polite! This is a polite thing. You’re… taking a crying pony back to your place so they can… cry in peace… okay… not so much a polite thing. A friend thing, then. Just two buddies taking refuge in… one’s bedroom to work through… emotional suffering… Okay not so much a friend thing either…’

‘Guilty, what the fuck are you doing?’

“I found it!” Crook snapped me out of my daze. When he spoke I was I was putting away those cherries, apparently. I’d kind of been on autopilot.

“Huh?”

“The cream. Now I can make me a drink.” He pulled a rocks glass out of my cupboard.

“Could you at least wait until I’ve got all my shit put away before you start taking more out?” I pleaded. “Why don’t you do me a favor and shelf the liquor? You still know how to organize that stuff, right?”

He clicked his tongue. “Fine…” What a whiner.

It was at this point that the sound of Derpy wailing began to arise. Crook let out a big sigh. “Look I wasn’t even gonna say anything but… who is this mare? She a client or something? Because this is not a service you used to offer.”

I just sighed.

“Just sayin’.”

“She’s…” I paused. I was trying to figure out what it was safe to tell him. “… a friend.”

Crook scoffed. “Guilty Pleasure? A friend? I don’t believe it.”

“Why you gotta be like that?” I put some fake hurt into my voice.

“No, I mean I seriously don’t believe it. As far as I remember, I’m the only friend you’ve ever had, Guilty.” Bottles clinked together as he continued to place all my new spirits in the liquor cabinet. “When did you grow a social life?”

“Hey, fuck you too.” I shot him a glare. Unfortunately, I didn’t look very threatening holding two loaves of bread.

“I’m just sayin’…” Awkward silence. “You want the beer in the fridge?”

“Yeah, just put it in the door.” More silence.

“So uh… you do this a lot?” he asked less than casually.

“Do what?”

“Bring home cryin’ mares.”

“First time.”

“Hmm…” I could hear the judgement in his voice. Like he’s one to talk. He’s brought home more mares than I ever will.

So, we got everything put away while Derpy had her cry. Eventually she crept out of the bedroom and out into the living room. Her eyes still red, her pride in tatters, she slowly made her way to my table. I happened to be reading one of my outdoor living magazines. Crook was busy debating which of the three beers he’d bought looked the tastiest.

Now the aftermath of a breakdown is something I’ve dealt with a few times. There’s one very big secret to smoothing things over in a situation like this, and it’s easy to do.

Act like nothing happened. Pretend all is well. Don’t mention it. Don’t bring it up… unless they do. Even then, always play it down. They already feel bad about making a scene, no need to make things any worse.

“Hey.” She put on her best smile. “I can’t believe-” Her voice cracked. She laughed nervously about it. “I can’t believe I started crying like that.”

Friendly smile. Even calm tone. Eye contact. Shrug of the shoulders. “Eh… it happens sometimes. Everypony cries sometimes.”

“Especially this guy!” Crook called from the kitchen.

I almost slapped myself for forgetting my manners. Introductions were in order. “Oh, geez, that’s right. Derpy, this is Crook, my oldest and dearest friend. Crook, this is Derpy. She’s a local.”

Derpy smiled and waved. I love her little wave. “Hi there. Guilty was telling me he had company. *Ahem*… Thanks for walking me here.”

“Yeah, no sweat,” he responded absently.

Derpy turned her gaze back to me, and her smile fell. “I’ve… never seen Applejack act like that. She’s usually such a nice pony.”

“Really?” Crook and I asked in unison. That was a bit tough for me to believe, but I suppose it makes sense. She has something of a following, she can’t be a bitch all the time.

“Mmhmm.” Derpy took a seat across from me. “When the town hall was all busted up, she promised to use her rodeo winnings to repair it. Everypony showed up to see her off.” She sighed. “I didn’t know she could… be like that.”

I shrugged and tossed my magazine onto the table. “Well… that’s the only Applejack I’ve ever seen. She’s hated me from the get-go.”

Derpy shook her head again. “I just don’t know why.”

“Well... *gulp*… I happen to be aware of the possibility that her mother abandoned her family for an escort… or so I hear.” I did my best to look innocent. I still feel a bad about that one, though, so it wasn’t as easy as I would’ve liked to play it off.

Derpy’s ears shot up. “Really… wow… that’s terrible.” She frowned. I could already see her sympathizing with Applejack.

“I still don’t think it excuses her behavior,” I interjected.

“Yeah, she was kind of a bitch,” Crook chimed.

I perked up at that, and turned to face Crook in the kitchen. “That reminds me… what were you getting at, agreeing to go on a date with her?”

“He’s gonna date her?” Derpy asked. I just shrugged.

“I’m not getting at anything…” Crook came into the room with beers in tow. “…I’m just… keeping as many cards in my deck as I can.” He offered me a beer which, for some reason, I accepted. He offered one to Derpy as well, but she turned it down.

I twisted open my bottle and took a swig. It was a fairly pricey beer, and was actually pretty tasty. It was a nice brown ale, very smooth. As I drank I briefly tried to wrap my head around Crook’s answer. He’s never really had what one might call foresight. Him thinking about anything beyond the now… not really his style.

I suppose he’s sort of… grown up… kind of… in some small ways.

“Well whatever the case, thank you for not pounding her face into the snow.”

Derpy gasped. “Why would he do that?”

I opened my mouth to respond, but Crook beat me to it. “ ‘Cause nopony fucks with Guilty.” He threw an affectionate hoof around me and gave me a comradely little shake.

I laughed nervously at the still-mortified look on Derpy’s face. “*Ahem* well… what Crook means to say is that when we were younger, Crook liked to fight my battles for me.”

“Hey! Somepony had to fight ‘em,” Crook jabbed, taking a sip of his ale.

I nodded. “True enough. Thankfully, he seems to have developed a sense of what’s socially acceptable. Better late than never I suppose.”

Crook chuckled. “Well fuck you too, crybaby.” He punched me in the shoulder, causing me to spill some of my beer. You know, I don’t normally drink, but something about Crook being in town made me want to. I’m not sure why.

Anyways, Derpy couldn’t help but chuckle at our antics. “You guys are so funny.” She no longer seemed to be concerned with Crook’s violent temperament, which was a plus. And Crook seemed to be warming up to her as well. Not that I doubted he would. She’s a mare, after all.

“So, Derpy, do you want to stick around for a while?” I asked.

“Sure.” She smiled. “You guys are fun.”

‘Yes!’ This was awesome. My best friend was here, my best Ponyville friend was here, we were drinking. It was wonderful. Derpy and Crook got along great, which was… just fantastic. They swapped stories, they told jokes (Crook’s tended to be fairly off-color), Derpy told Crook all about the little hike we took together, which amused Crook to no end. He couldn’t get enough of those ray-things we saw. (I still need to ask Twilight about those.) Crook ended up telling a few stories that involved me getting my ass kicked. Much to my dismay, Derpy seemed to enjoy them very much. He also complimented the punch Derpy had thrown at Applejack, which caused Derpy to blush immensely.

Oh, here’s something. Derpy mentioned that she was a client. I wouldn’t have thought she’d do that. I suppose it’s really something she’s not ashamed of…

I’m… I mean I’m glad about it of course, it’s nice having someone be open about that sort of thing, but…

I dunno. I keep getting the feeling that that openness is going to get her into trouble. I’d hate to have Applejack on her case too. Or hell… if her daughter’s friends found out? Yeesh.

*Sigh*

I dunno… I worry too much.

So anyways, we had a nice little chat. Derpy eventually realized that she had to get home to make dinner, so she gathered up her groceries and got ready to leave. After she’d grabbed all her stuff, she said her goodbyes and made for the door. Right as she was about to go, however, Crook spoke up. “Guilty, walk the mare home.”

“Huh?” It was kind of an odd request, but not unlike Crook. Even if he’s needed lessons in manners, he’s never needed lessons in chivalry.

Derpy gave a dismissive wave of her hoof. “It’s okay, it’s not even dark.”

Crook looked me dead in the eye. “Guilty… walk the mare home.” Oh… well then… my mistake. This was not a request. This was an order.

I put a hoof up in defeat. “Alright, I’ll walk her home.”

Derpy seemed a tad distraught. “No really, you don’t have to-”

“It’s fine.” Calm smile. “I’ll never hear the end of it if I don’t.”

“But really, you don’t have to-”

I just grinned. “Derpy. It’s fine.” It really was. I didn’t have plans or anything; it was no trouble at all. “Shall we?”

So Derpy and Crook said their goodbyes, and out the door we went.

It was lovely outside. The sun was starting to dip, but it was by no means dark. Naked trees cast long crooked shadows across the frost and snow. There was no wind; the world was so still. Brisk, beautiful, almost delicate... It was wonderful, in the true sense of the word. There are no moments like that in Manehattan.

Such wonder, however, seemed commonplace to Derpy. She just trotted alongside me, with a great big smile on her face. “Crook seems like a fun guy. You and him go all the way back, huh?”

“Pretty much.” There was a silence there, though not a particularly awkward one. “You know, he’s the one who got me into this line of work? Maybe I should be blaming him for this whole mess with Applejack.”

Derpy sighed and just sort of deflated. “I still can’t believe her.” She buried her face into her hoof. “I still can’t believe me.”

I cocked my head. “How do you mean?”

“When I punched her,” she groaned. “And after all the stuff I tell Dinky about ‘using your words.’ I’m such a hypocrite.” Her head sank.

I gave her shoulder a light tap. “Enough with the self-pity.” She glanced up at me with her good eye. “I should buy you a drink after that. Do you have any idea how long I’ve been wanting that mare to get punched in the face?”

Derpy giggled. “Well… I’m sure you would’ve at least hit her harder.”

“Oh no. I’m worthless in a fight,” I confessed.

Her whole head turned sideways. It’s adorable how she does that. “But you’re so strong,” she protested.

“Oh trust me, Derpy. I’ve been in a lot of fights... and I’ve lost every one.” I shrugged. “I never would’ve touched Applejack. I would’ve missed my punch and tripped or something equally emasculating.”

She laughed again at that one. “Hehehe, you always make me laugh, Guilty. How are you so good at that?”

“Practice, I guess.” Another silence followed, but again, not an awkward one. “So you liked Crook, then?”

“Mmhmm.” She nodded. “He’s silly. You two gonna have some fun tonight?”

“He is, I’m sure. He has a date.”

Derpy frowned. “So he’s leaving you all alone with nothing to do?”

I chuckled. “Derpy, most nights are just me home alone.”

Her face turned to one of shock. “What? No way!”

I did my best not to make a big deal out of it. “Derpy, it’s fine. I value my quiet time.”

“Nuh-uh! I bet you’re really bored. Especially if your friend is going out without you.”

I opened my mouth to protest, but ultimately she was right. I was really bored most of the time. Sure I could pass the time with exercise or reading or chores, but that was only to stave off the emptiness of my evening. Well… unless I had a client, that tends to be very stimulating.

“That’s it. You’re coming with me to Goldy’s house tonight!”

I almost choked on nothing at all. “Wh-what?”

“You’re coming with me to girls’ night,”she insisted.

‘Girls’ night? Carrot Top? What is this? What am I being dragged into? This is destined for disaster. Get out, Guilty, while you still can!’ “Derpy, I don’t think-”

“No buts!” she insisted. “I’m not letting you be all lonely ‘cause your friend is blowing you off.” And that was fucking that, apparently. Now I had something to dread… hooray. “I can’t believe he would do that, though.”

I gave a dismissive grunt. “It’s just his way. He has to hit on everypony he sees.”

Derpy’s expression remained stony for a few moments before ultimately softening. “He really cares about you, though. I can tell.”

I could only nod. “That he does.”

She mused silently to herself for a moment. “He kinda reminds me of Goldy. She’s kinda like that with me. Always trying to protect me, always worried.”

“I’ve noticed.” ‘She’s even trying to protect you from me, as a matter of fact.’

“Well… I think your friend is a bit less… zealous than Crook.”

Derpy just shrugged. Silence once more.

“I’m glad you like Crook, though,” I said. “It’s nice knowing my two best friends get along.” ‘Guilty, you fool! You haven’t-’

“I’m your best friend?” Derpy asked quizzically. I hadn’t had this kind of conversation with Derpy yet. I’d just slipped up and went ahead and called her my best friend.

I’m not sure how long I’ve really considered Derpy something of a ‘best friend’ but she’s certainly my favorite pony in Ponyville. I dunno, the label just made sense in my head… I’d just never given my thoughts voice. “Well…”

I had to tread carefully, or I might come off as desperate. This was gonna suck. “You’re certainly my best Ponyville friend, I guess. Most ponies in town don’t even take the time to say hello, especially not my clients.” I shrugged casually. “You’re kind of… one of the only ponies who’s really decent to me.”

Derpy’s face just fucking fell. She stuck out a hoof to stop me in place, and looked me square in the eyes. “That can’t be true. It just can’t.” She wasn’t arguing. She was pleading, begging for me to be joking or exaggerating.

I think my expression told her I wasn’t.

“So you mean… most ponies are like Applejack?!”

This was not a pleasant conversation to be having. It was just crushing her. “Well… Applejack is by far the worst. In fact she’s probably the only one who’s actively mean to me. Most ponies just… gossip.”

“I hate gossip.” Derpy snorted. “It’s just dumb.”

“Yeah well… everypony is entitled to their opinion.”

“Well their opinions are wrong! You’re a good pony!” She stamped her hoof into the snow, which resounded in a satisfying crunch.

I just sighed. This no fucking fun. “Well, I don’t think anypony in town is really keen to change their mind about me. Least of all Applejack, and she’s the heart of the problem.”

“Fuck Applejack!” Derpy shouted. As glad as I was to hear those words, it wasn’t the sort of language I expected from Derpy.

“Derpy, you don’t have to go that far.”

“No! Fuck Applejack! She called me stupid, Guilty! She basically said it right to my face! Nopony calls me stupid!” She pointed a threatening hoof in my face. It wasn’t me she was angry at, but it sure as shit seemed like it for a moment. She was panting; she’d worked herself up something fierce. I’m sure as fuck glad I was not the object of Derpy’s rage. I’m sure she’d wipe the floor with me.

I’d never actually seen Derpy’s angry face before that day, and I saw it twice. She’s quite the fucking spitfire, that’s for sure. I gently pushed Derpy’s hoof out of my face, and she realized how heated she’d gotten.

So, I let her collect herself. Her breathing returned to a steady pace, her expression changing from one of fury to one of embarrassment. She began to shake ever so slightly as the adrenaline worked its way through her system.

“S-Sorry. I just… I’m still kind of upset, *haha*.” She laughed nervously.

I chuckled. “Shit, I’m just glad you’re in my corner.” That seemed to make her feel better. “Between Crook and you, I couldn’t ask for better friends.” She even smiled at that one.

“You’re a good friend too,” she responded.

Derpy’s mood seemed fairly cheery as we entered the town proper. As we walked I came to a sudden realization.

‘I’m visiting a client’s house. This is a first. It’s not like Pinkie’s bakery or buying pants from Rarity’s boutique. I’m going to a home. A proper home. A home where Derpy lives and eats and sleeps with her dau- HOLY SHIT I’M GOING TO MEET DINKY!’

I almost had a heart attack. I was going to meet Dinky. Dinky! The precious little unicorn filly whose mother I routinely plow.

‘I don’t know how to talk to kids who are complete strangers. How do I talk to a kid who I know a fuckton about? What if she asks who I am? What if she asks how I know her mom? Dear sweet Luna, what if she asks me what I do for a living?’

‘Okay, breathe Guilty. It won’t be that bad. She’s just a kid, she’ll probably be totally uninterested in you. Don’t you worry at all, she’s probably-’

“We’re here!” Derpy announced as we stepped up to her modest home. I hadn’t even realized we’d arrived. Were we walking that long? No, it was just on the close side of town. Okay then.

‘Oh fuck, I’m not ready. This is gonna be bad. I’m gonna say something inappropriate. Holy shit, this is bad.’

Derpy quickly produced a key and unlocked her front door. “Dinky?! You home?!” she called. Her voice echoed through the house, only to be met with silence. “Looks like she’s still out playing.” She stepped into her home.

The house was… I’m gonna say “quaint.” It was a one-leveled little place, probably a little smaller than the first floor of my cottage. It was a cute pale yellow color, with white window sills. A little tiled roof, a little white fence, not much by way of decorations, it was… modest.

Okay, it was small. It was fucking small. It was a tiny little place, almost an apartment. There was very little furniture. There was a couch, a coffee table, a little dining room table complete with folding chairs, and that was about it.

But at the same time, it was… a happy place. Flour on the kitchen counter (no doubt remnants of muffiny goodness), little crayon drawings hanging on the fridge, a little block castle in the corner. That’s when it all sort of… hit me.

Derpy lives here.

I mean… I knew that, of course. But… being there, seeing that little cross-section of her life laid bare, it was almost like seeing a side of Derpy I’d never seen. Derpy has a whole life, a whole great big wonderful complicated life that has nothing to do with me. Again, I'd known that, it’s just… I dunno.

There’s a difference between knowing something and knowing something.

I guess.

I don’t know how else to put that…

“So anyways, this is me,” said Derpy, shaking me out of my distraction. I looked at her with a newly discovered sense of respect. “So come by at, like, nine. We’ll go to Goldy’s house and have fun.” She clapped her hooves together excitedly.

I swallowed hard. I suddenly found myself flustered. The thought of Carrot Top was disconcerting me. “Uh, sure… what are we, uh… gonna do there?”

“We’ll play poker or somethin’. It’s always super fun.” She smiled at me. “See you later.”

“Bye… uh… see you tonight.” I offered. ‘Really? See you tonight? That’s the best I can do?’

She gave a little wave and turn to close the door. And with that she was off to unpack groceries and cook up a dinner and all that shit. Off to live her little life.

I dunno, the whole thing was a little too… real. I mean…

*sigh*

So much of my job is helping ponies escape reality. When they’re with me they’re… apart from all that. Their homes, their friends, their problems, their everything. They never really bring it with them unless they need to. To me other ponies’ lives are to be sorted out with a few key words of advice, or to be heard about via small talk from chatty clients. I help with the problems, I listen to the gossip, I play along, I do whatever I need to do.

But I’m never a part of it. I’m always on the outside looking in. An impartial observer. That’s what clients want. That’s what clients need. A stallion who will listen to everything they have to say, and have it not really mean anything.

It’s like… I never judge a client, whatever they say to me: hey no big. That’s what I’m all about. They come to me in need of somepony who will accept them for who they are, somepony who won’t think any less of them for anything. I’m good at that.

But now… it was the other way around. Somepony was letting me into their life. Not just as a passing acquaintance, or a fling or whatever. I was a friend. I was being included in plans. I was going to get together and play cards. I was gonna have spontaneous wacky fun with Derpy.

This was… a life. It was a real life and I was being invited into it. It was comprised of the things that a life ought to be comprised of. Friends and neighbors and get-togethers and walking ponies home, and kids being out playing, and messy kitchens, and block castles, and all that shit...

…AND IT FUCKING SCARED ME!

Because it wasn’t… isn’t Derpy’s job. It isn’t Derpy’s job to like me no matter what. It isn’t her job to accept and spend time with me regardless of my actions… and that means two things:

Derpy actually does enjoy my company.

I can fuck this up at any time.

So there I was. Standing outside Derpy’s cute little house, staring at the doorway where she was standing. And it was slowly dawning on me... that this was real. Not an act. Not a session. Real.

And then I walked home.

I don’t even remember the walk back, it just sort of flew by. The next thing I knew I was walking back into my great big warm cabin, and Crook was drinking a mojito. I didn’t even know where he found the mint, and I could not be fucked to ask.

“She make it home okay?” he asked, before taking a large swig.

“Yeah,” I responded thoughtfully. I immediately shed my winter clothes, paying no mind to putting them away properly, and sat down by the fire. “Hey Crook?” I called.

“Yeah?” he answered.

“What did you say you needed Kahlua for?”

“White Rushin’.”

“Make me one, would you?”

“Uh… okay.” He was perplexed, and justifiably so. My mind was still afire with thoughts of life and friendship and all that gay shit, and it showed. I was just sort of… staring into the flames.

Crook knew better than to ask what was up… he did anyways. “What the fuck happened to you? She dump you or some shit?” He put a tan looking beverage in front of me.

“We’re not dating,” I responded absently.

Crook walked around in front of me and looked me in the eyes. Scratch that, he was looking at my eyes. “Are you fucking goofy? What are you on?” He even went so far as to lift up my eyelid to see if I was bloodshot. “Can I have some?”

“I’m not high, Crook. Just... contemplating,” I explained.'

“Ah, shit. She did dump you. That’s rough. I could tell you liked her too.” He pushed his little tan concoction toward me once more. “Drink up, Guilty.”

“Still not dating,” I said before tasting Crook’s little cocktail. It wasn’t bad. Too much cream, though. I could do better. “Crook… what do you think it means to have a life?”

“Is this where you tell me you’re dying?” he quipped.

“I’m serious.” I took another sip. “What does it mean to ‘have a life’? Is it having friends?… hobbies?… a job? At what point is there enough going on for you that you actually have a life?”

“How the fuck should I know? I do work. I get dates. I talk to my fellow whores. That’s a life. S’all I really need.” He sipped his own beverage. “Why? You feelin’ like you don’t got a life, Guilty?”

“Actually for the first time, I’m feeling like I’m starting to get one,” I confessed.

“First time? Shit, you had a life in Manehattan, didn’t you?” He sounded almost offended.

I had to think on that one. I had acquaintances. I had Crook. For a time, I had Sunny. The more I thought, the more I decided that I did, in fact, have a life in Manehattan. It was just… different.

“*sigh*… I dunno...” I motioned for him to sit down beside me, which he did. I leaned into his stalwart frame as I drank deep. It had a good flavor, however imbalanced. I may keep some Kahlua handy from now on.

“So anyways, you got any clients tomorrow morning? Or can Pinkie stay overnight if I end up bringin’ her here? Oh and also, where do you keep your potions? You got like a hundred fuckin’ chests in there.” I could hear the gears turning in Crook’s head. He was already creating a strategy to seduce Pinkie Pie.

“No clients. The chest next to the door,” I answered. And so, reveling in the warmth of the fire and Crook's company, I began to doze off.

I have the strangest dreams when I take naps. They’re never… solid. Everything is so ethereal: people, places, objects. It’s all… color without substance. Just smoke and sound.

And I did dream. It was kinda fuckin’ weird, but I remember it pretty well, so here goes:

I dreamt of silver and gold in a world of red. Everything I touched was soft and the air smelled sweet. I dreamt of black and white. My mouth tasted like blood, and the world reeked of sex. I dreamt of cold. Everything was loud and my skull was pounding with pain. I dreamt of yellow, and everything made me feel stupid.

Yellow turned to orange, and that orange turned into a fire, and before I realized it, I was awake again, staring into the flames, still leaning into Crook.

There was drool on my face. I never drool. I wiped it away quickly. “Mmmmhow long was I out?”

I felt him shrug. “Like five minutes.”

I rubbed my eyes and lifted myself up. My face felt warm, but that happens to me when I nap… and drink… and stare at a fire. “Where’s my cocktail?”

“I finished it,” he replied.

I glowered at him.

“The ice was melting! It was gonna go to waste!” he said defensively.

“Fine.” I rolled my eyes. I wasn’t really upset, anyways. “What time’s your date?”

“Shit. Uhhhhh… Six I think?” he mused.

“You think?” I would’ve scolded him if I thought it would have any effect.

“I dunno. I was in the zone. I can’t remember all that shit when I’m too busy being fuckin’ sexy.” He gestured to his entire self. “See this? Takes total concentration to stay at full sexiness.”

“No one expects you to remember everything, Crook. Just, you know… a time… a place… the girl’s name. Those three’ll do ya in a pinch.” I love when I get to act superior with Crook. “You do remember her name, right?”

“Pinkie Pie. I ain’t that stupid,” He assured me.

I opened my mouth to respond.

“And I swear if you say, ‘coulda fooled me,’ I will fuckin’ pummel you.” A large white hoof poked my firmly in the chest.

“Classy,” was my only response.

So some time passed. Crook had another mojito or two. I perused a magazine, read a few articles about mountain paths in the frozen north. They sound pretty amazing. An aurora overhead. Frigid winds. Fifteen thousand feet above sea level. Must be amazing.

Now that I think about it, I’ve been neglecting my non-hiking-related reading. I don’t know what’s ‘in’ or ‘out’ in the fashion world. I don’t know what fruit’s in season. I don’t know anything about books coming out or films or hit songs. I’ve got some catch-up to do.

Anyways, after a time, Crook took off. He quickly brushed his teeth, borrowed a nice looking hat from my closet (without asking), and rushed out the door. Soon Pinkie would be blushing and giggling and having fun with the sexiest stallion Ponyville had ever seen.

So I proceeded to whittle away the hours as I waited for nine. I spent some time cleaning up the bedroom. It was already clean but… it can never be too clean. I washed and put away all the glasses and liquor that Crook had been using. I was just trying to make the place nice for Pinkie. I knew that if she came over it wouldn’t be for a session per se, but that didn’t mean I didn’t have my personal standards. By the time I finished prepping I still had an hour before I was supposed to meet Derpy.

So I… twiddled my hooves. Made myself a snack. Double checked the bedroom. I locked my bedroom, just to be safe. Sat… thought… stretched, anything to make the clock move quicker. It was sort of agony. Time moves slower when you’re waiting for something.

Then the time came for me to leave. I wrapped myself up in scarf and coat once more and stepped into the winter night. It was still nice out. The moon was full; the air was still; I could hear owls hooting. Picturesque. I trotted happily into town. I was almost giddy with excitement. I didn’t know what I was in store for and I didn’t care. Just the idea of a proper get together with a friend was making me grin from ear to ear.

So I arrived. Ponyville’s streets were all but dead. I think I saw one other pony out walking, but I wasn’t really paying attention. I made my way to Derpy’s home. The lights from beyond her shutters shone with a warm glow. Inside I could hear her humming a little song. I trotted up the little path and gave a knock.

“Coming!” she announced from beyond the threshold. It was such a happy little proclamation; normally when she says that it’s more along the lines of “c-c-COMING!”

Ha… sex humor.

The door cracked open. It’s kind of odd; for some reason I was expecting her to be dressed up. I’m not sure why. “Hey Guilty.” It was so casual. Not at all different than normal just… “Hey Guilty.”

Then again, this wasn’t any different than normal… for her. I was practically jumping out of my skin. But her? Just another night out at Carrot Top’s…

‘Oh, fuck me, I’m going to Carrot Top’s. Oh fuck me! I’m going to meet her girlfriend! One way or another this is going to be awkward.’

On the bright side, I wasn’t overly excited anymore.

Still excited, though.

Kinda.

Not much.

Okay, a lot. Still very excited.

Anyways…

“H- *ahem* Hey Derpy.” ‘Nice one.’

She turned back to her house and shouted. “Dinky! In bed by ten!”

“’Kay, Mom!” I heard from some unseen room.

She grinned. “Let’s go.”

And go, we did, through that tranquil night. The snow crunched underhoof, our breaths hung thick and white in the air. I was almost afraid to ruin the perfect scene with a question. “So, uh… who’s coming to this thing?” It seemed a pertinent question.

“Oh just the girls. Goldy, Lily, Lyra, Bon Bon.”

‘Lyra and Bon Bon will be there? Cool.’ I was beginning to feel less apprehensive about the whole thing. More ponies there that I knew and liked? Sounded good to me.

“So what, uh… what happens at these things? You said poker?”

“Poker, drinks, board games sometimes, movies sometimes. It’s just a fun night in,” she said happily.

“Sounds like a plan.” I said more than a little nervously.

As we approached…

Hang on…

My client is here. Time for a good sexing.

Author's Note

So it's been a while. I hope you all enjoy. Please throw me thumbs ups and comments and faves and such, it sustains me. 0_0 But seriously, you guys are the best fans, and I hope to keep writing for some time.

Also, just because i think it's likely to come up. I AM aware that the cocktail is called a white russian. However, seeing as there's no "Russia" in Equestria, I approximated it to something universe appropriate.

Many thanks to aquapunkchick, BlackSkulls, coandco, and Jake the Army Guy for editing.

Lovers

Chapter 13

Lovers

Well, that session proved to be longer than I anticipated. I’m pretty exhausted, so I’m gonna see how much I can write before I pass out. If nothing else, I’ll make sure I get to the important part.

Where was I?

Ah, yes.

Derpy and I approached Carrot Top’s home. It was a nice looking place. Much larger than Derpy’s little hovel. A nice tiled roof, a darling picket fence; it was a pretty nice looking place, to be honest. I could hear Lyra’s voice bellowing joyously from within. With a happy little hop up onto the porch, Derpy ran ahead and knocked on her friend’s door. I followed suit, sans adorable hop.

The door creaked open slowly, revealing the darkened silhouette of Carrot Top. I could just barely make out the look on her face, but it was fucking priceless. Her jaw actually dropped as she tried to comprehend my presence. “Goldy!” said Derpy. “Look who I brought!”

Her jaw continued to dangle beneath her mouth. Words failed her. For a few seconds she just sort of stood there, shocked still. On the hike she was at least ready for me. She knew in advance that I was going to be there. Here she was being blindsided by me, just like Rarity at the spa. And just like with Rarity, I decided to cut her a little slack. “It’s nice to see you again Ms. Harvest. Sorry for coming unannounced.” Apologetic expression. Sincere tone. Nervous scratch at mane.

“You don’t mind, right Goldy?” Derpy wore a mask of glee. Nopony could’ve said no to that face. Nopony.

“Oh…I…uhhhhhhf course not.” Innocent smile. Welcoming gesture. Obliging attitude. “Good to see you again, Mr. Pleasure. Can I take your coats?” Enter Derpy and Guilty.

“Of course. Thank you.” Friendly smile. Small bow. Wait for Carrot Top to take Derpy’s coat.

“Derpy, Bon Bon brought those chocolate pretzels. You should grab some before they’re all gone.” Take Derpy’s coat. Start on Guilty’s coat.

“Oh, yum!” Exit Derpy.

“What the hell are you doing here?!” she hissed.

Ah, there she was. That horrid angry little mare I know so well. Up until that moment we’d both been playing our parts, veiling ourselves in the happy little lie we share (I was a much better performer, by the way). But, the moment Derpy was out of earshot out came the irate whispers and snarky jackassery.

“I’m here for the promise of alcohol and gambling… and maybe a chocolate pretzel. That sounds kinda good,” I responded, dodging the question entirely, like only a master jackass can. It felt so good to just fuck with her a little. I know it wasn’t “professional,” but it was damn enjoyable.

“You know what I mean.” She prodded me with an angry hoof. “What are you doing with Derpy? Did you talk her into bringing you here? Is that it? ” she asked, leaning into my personal space quite a bit.

I gently knocked her hoof away and took a step back. “Geez, right away with the accusations. What is it with you?” I dusted off my coat in an exaggerated fashion. “Derpy invited me,” I explained. “In fact, she insisted I come to this thing. I have company over for a while, but my company made plans, so I had a free night. There. Presence explained. Happy?”

If glaring was sport, Carrot Top could be world champion. Her award winning scowl, however, was interrupted as a lovely pink mare stepped into the entryway where we’d been standing. “Honey, what’s keeping y— Oh!” she said, noticing me. “Who’s your friend?” Now, this was a mare with a winning smile. Her blond mane, the little flower behind her ear, and gorgeous figure, everything about her was just darling.

‘Is this Lily? Oh, that’s a lily in her hair… and her cutie mark is three lilies. Yeah… this is Lily.’

“Oh, uh… um…” Carrot Top stuttered.

‘Find your words. It’s not that hard.’

“Lily, this is—*ahem*—this is Guilty Pleasure. Derpy invited him.” She didn’t need to emphasize Derpy’s name like she did, but she was on the spot.

To Carrot Top’s credit, she actually said words to me that didn’t make it sound like she thought of me as dirt. “Mr. Pleasure, this is Lily. She’s my, uh… I mean she’s—”

“I’m her girlfriend,” said Lily flatly. She held back a sigh. This was clearly a thing between them.

“Y-yeah that,” replied Carrot Top sheepishly. Lily rolled her eyes.

I interjected. “Well, it’s very nice to meet you, Lily. You have a lovely home.” I may have only seen the first few yards of the place, but it was very nice: hardwood floors, a nice ceiling lamp, a very large coat closet. It was very warm too, like Derpy’s place. This home was full of life as well.

Carrot Top cringed slightly at my compliment. Lily smiled falsely. “Oh, no, no. I don’t live here.” The slightest hint of venom in her voice gave away her malice. I’d clearly stepped into yet another thing of theirs. I could sense a little tirade about how she doesn’t live with her girlfriend, and by the looks of it so could Carrot Top. She looked fully prepared to be chewed out but the charming little blonde. Luckily, Lily quickly changed the subject. “I live with my sisters Rose and Daisy. Have you met them?”

‘Rose… that’s the mare that’s always fucking with Junebug, I think. Geez… small towns.’

“Maybe. I might’ve bought sunflowers from them at some point, though.” A wicked idea occurred to me. “I make a mean sunflower sandwich. Don’t I, Ms. Harvest?”

Carrot Top gulped audibly. I think she’d been expecting me to act like we’d never met. I would have, too, if it weren’t for our little expedition to Ghastly Gorge. That was something that had happened off the clock, and that meant that it had happened. After all, Derpy could’ve brought it up as well, and it would certainly be just as awkward then. This way, it happened with as few people watching as possible.

Aren’t I such a gentlecolt?

Lily was understandably perplexed. “Oh, have you two met before?” Carrot Top was still playing catch-up so I oh-so-politely answered for both of us.

“We ended up going on a hike once. Derpy was there. It was just going to be us, but she invited Ms. Harvest along at the last minute,” I explained.

“Yeah, she does that, apparently,” griped Carrot Top. She may have put a smile on her face, and pretended like it wasn’t a gripe, but it was a gripe… aimed at me… and she snuck it right by her girlfriend.

*Sigh*

We’re like bitchy little girls when we’re together.

I just eat it up.

“Oh, I didn’t realize there’d been three of you. I thought it was just Derpy and her. She never mentioned you.” She sort of sounded… suspicious maybe? No, not quite. Something was on her mind, though. ‘Oh, they were fighting that day, weren’t they? I’d forgotten that. That’s gotta be it.’

“Well, we didn’t talk much.” ‘And when we did it was mostly yelling.’ As I stood there I became aware that the three of us had just been standing by the front door for far too long. “Should we join the others?” I offered.

Lily almost looked aghast. “Oh, of course. They’re probably waiting on us.” The three of us then made our way into something of a… den? Rumpus room? Something like that. It was a nice big carpeted room. Couches and chairs surrounded a small coffee table in front of a brick hearth, lit with a crackling fire. The quaint little table was covered with drinks and snacks. There were two-liter bottles of soda, a couple of bottles of wine, trail mix, assorted cheeses, crackers, little cookies and cakes and candies and such. It was a sizable spread.

Lyra and Bon Bon were cuddling on one of the several couches when we entered. Derpy was stuffing her face with what I assumed were chocolate pretzels. “Guilty?” Lyra grinned instantly upon seeing me. “Dude, what are you doing here?” She stood up and instantly offered me a hoof-knock, a social custom I still don’t completely understand. I obliged either way.

“I never expect to see you so soon, Guilty,” said Bon Bon, who stood up to join her lover and offer me a much more sensible hoof shake. “It’s only been a day, hasn’t it?”

“Just about,” I answered with a grin. ‘Food, friends, wine… this is awesome.’

Lily just appeared bewildered as I greeted my newest clients. “Well, now I feel left out. Am I the only pony here that hasn’t met you before?”

“Guhlty! You huff to trah the prshels!” Derpy was suddenly before me. Her mouth was totally full, and she was offering me what was clearly a chocolate pretzel. It honestly just looked like a soft pretzel covered in chocolate. I don’t have much of a sweet tooth, as I’ve said, but I wasn’t going to turn it down. I chomped down the crunchy little thing. It was actually very tasty, sweet and salty and crunchy and melty and soft. Delicious.

I swallowed the thing down. “Are these homemade?” I asked.

Bon Bon spoke up. “Mm-hmm. I sell them in my shop.” Pride lit up her face.

“They’re very tasty,” I said politely, before Lily spoke up again.

“So…wait… how do all of you know Mr. Pleasure?” she asked, desperately trying to play catch-up.

Derpy swallowed her mouthful of sweet-savory goodness before answering. “I’ve been seeing him since he came to Ponyville! He’s awesome!”

Lyra was next to answer. “Bonnie and I paid him a visit last night.” She nuzzled her partner obnoxiously. “Didn’t we, sweetie.”

Bon Bon yelped at the sudden accosting. “GAH! Lyra, quit it!”

Lily took in her friends answers before turning back to me. “So… what exactly do you do Mr. Pleasure? Are you a… therapist?” she guessed.

I looked for any signs of dread from my three clients. None of them seemed afraid of my answer. Was this okay? Could I just come out and say it? It certainly seemed safe to answer. ‘…Okay, fuck it, I’m gonna tell her.’

“Well, Lily, I’m, uh…*ahem*... I’m an escort,” I explained carefully.

“Oh, so you…” For a moment she tried to wrap her brain around my answer. “I’m sorry, how do you mean ‘escort’? You mean like a bodyguard?” Poor girl. Everyone else in the room was on the same page as me. Time to be blunt.

“Well, no. When I say ’escort’ I really mean… you know… ‘prostitute’.” I laughed nervously. It wasn’t false this time, I was actually feeling a little awkward.

Lily’s eyes practically bulged out of her head. “Oh… Oh… Ooooooh…” Realization dawned on her. “You’re him! I never thought… oh my goodness!” Her words were getting away from her. It appeared that my reputation had preceded me. “So wait, you mean… Derpy, when you said you… oh… Oh!” She turned to Lyra and Bon Bon. “And, you two? But you’re… I thought… oh dear.” She almost had to steady herself. Carrot Top just continued to look guilty through the whole affair, staring at the ground while her lover processed everything.

I decided to speak up. “I’m sorry, I wasn’t trying to surprise you or anything.” ‘I should just be polite for now. I don’t know what she’s heard about me or from whom. For all I know she could be one of Applejack’s little sheep.’

“No, no… it’s fine. It’s just… you’re so… kind. The way Applejack talks about you—”

“Fhuk Happljahk!” came a yell from Derpy’s overly stuff mouth.

“What’d you say?” asked Lyra, who was really more interesting in nuzzling Bon Bon than anything.

Derpy swallowed quickly. “Fuck Applejack!” she repeated. “She was so awful today.” Everypony could scarcely believe their ears. Lily brought a hoof over her mouth, while Carrot Top, Lyra and Bon Bon just went wide-eyed.

Lily couldn’t accept what she was hearing. She was just shaking her head. “We… can’t be talking about the same Applejack. She’s not like that,” she tried to explain. Clearly, in her mind there was a misunderstanding on Derpy’s end
.

“No,” Derpy explained. “She was awful. She was bullying Guilty. She was saying such awful things. And she called me stupid.” Derpy told it like it was. All of those things were certainly the truth.

Everypony collectively gasped with the exception of Carrot Top, who was suddenly no longer feeling sheepish. “What?!” she cried, both shocked and furious.

“She called me ‘a few apples short of a bushel’. In front of everypony!” Luckily for Derpy she’d actually calmed down about the whole affair. She didn’t appear as the fragile little mare that I took back to my cottage. She was that little spitfire again.

“This is Applejack we’re talking about, right? Country accent… blonde… always wearing a hat?” Lily was trying as hard as she could to find any explanation.

“I knocked that hat right off her head!” Derpy declared.

Lyra laughed openly, while everyone else’s jaws just dropped. “You hit her?” asked Carrot Top with concern.

Derpy blushed. She realized once again that she’d gotten a bit too passionate about things. “Y-yeah… I hit her.”

“Oh my gosh, Derpy!” exclaimed Lily.

“You got into a fight? Did she hurt you?” Carrot asked, placing a hoof in Derpy’s shoulder. She was clearly worried.

“I’m fine, Goldy. It…” Her blush grew redder. “…it wasn’t really a fight. I just sort of… hit her.” Her head fell. Poor Derpy. She already felt bad about the whole affair, and now it was being paraded around for her.

Once again, I intervened. “Look, I think I started something here that I really wasn’t aiming to… why don’t we change the subject?”

Bon Bon wholeheartedly agreed. “Guilty’s right. Why don’t we sit down. We can sort all this out some other time, right?”

Everypony agreed, even Carrot Top, after she made sure that Derpy hadn’t been hurt. Everyone took a seat around the little coffee table. Lily poured everyone a glass of wine. It was okay, not the best. I held back any comments about how Lily was clearly acting as more of a host even though she didn’t live there. I didn’t feel like opening any more cans of worms.

Even if that would’ve been hilarious.

So, we nibbled at the snacks and sipped at our drinks, some more that others (Lyra). I found Lily’s daisy cakes to be excellent. With better wine and some muffins the atmosphere might’ve been perfect. I gathered that this was a weekly event, and everypony had stories to tell about what had been going on for them. Lyra was apparently going to be making a short trip to Canterlot for a recital of some sort. Bon Bon had a nice little story about a new brownie recipe she’d been trying out; she claimed it was almost perfect. Carrot Top had a fascinatingly dull story about a broken trowel, as well a bit of gossip about some stallion named Lucky. I didn’t really pay attention. Lily and her sisters’ greenhouse apparently had a window broken, which was unfortunate. I suppose, though, that could afford Junebug a little slack in terms of keeping up with Rose.

Derpy’s story was vastly more interesting to myself.

“Okay my turn!” she began, sitting happily in her little chair. “And I was gonna tell you earlier Guilty, but I forgot.”

My ears perked up. “You were going to tell me?” I asked.

“Uh-huh! Mister Crate assigned me a new route. And you’re on it!” She bounced in her seat as she spoke.

I was genuinely pleased. “That’s... that’s awesome, Derpy.” I actually found myself smiling as well. Seeing Derpy every time I had a magazine or a letter was a pleasing prospect. As of yet, I haven’t had anything come in, but… hopefully I’ll see her soon.

I’m getting ahead of myself.

Anyways.

Derpy also had a little story about Dinky to tell. Apparently she going to be playing in some peewee hoofball league, and Derpy was having trouble with the people she was supposed to order her uniform from. It sounded like the people on the other end were being extremely unhelpful, which always sucks.

I had a similar anecdote about ordering some leather bindings that I decided wasn’t appropriate for my present company. As such, I said nothing.

Or at least I tried to. But once everypony had told their story, I noticed that they were looking at me expectantly. “Oh… is it my turn then?” I hadn’t been planning on… sharing anything. I didn’t have any sort of story prepared. Besides, anything interesting that does happen is strictly confidential. “I’m… not really sure what I should say.” I swallowed nervously.

“Oh come on, Guilty,” said Lyra. “You gotta have loads of awesome stories.” Clearly she was hoping for a raunchy tale or two.

I sighed. “I have plenty of stories, but… not many I can really tell.” Anything I could think of was about a client, and therefore off-limits.

“How do you mean?” asked Lily. Everypony else had gathered what I meant, but Lily was totally unaware of the… discrete nature of my work.

Derpy answered her question without hesitation. “Anything that happens with a client is private.” She smiled as she spoke.

Lily looked confused. “But… just a moment ago you told me about a hike you took with Derpy.”

“That wasn’t a session,” I explained. “That was just for fun, I wasn’t getting paid or anything. It’s the same for right now. This is just… hanging with friends.”

“Oh, so you’re… not being paid for this,” she clarified.

I was happy to clear up any misconceptions about my profession. Besides, Applejack had probably been feeding her lies about me for ages. “No, I’m just… here… not costing anypony anything.”

“Huh,” was all she said. She seemed to approve of my actions, which was good, I guess. “Well anyways, if you can’t tell us anything, I understand.”

“Oh! Tell a story about when you and Crook were younger!” offered Derpy.

Lyra and Bon Bon shared a look. “Who’s Crook?” asked the earth pony.

“A friend. He’s in town. Derpy met him earlier when we were grocery shopping.” I decided to skate over the whole Applejack incident and the ensuing fallout.

Lily cleared her throat. “Is he a, uh… you know… as well?” She was clearly a tad uncomfortable talking about my profession, but she was making an effort, and I appreciated that.

“Yeah, he’s an escort too. We go way back.”

“So Derpy said you have stories with this guy?” I could still see a glimmer in Lyra’s eye. She wanted a raunchy story even more now. I decided against obliging her, I was trying to get Lily to like me, not scare her away. I had a more appropriate story in mind. It was a story from way back, back before I was Guilty Pleasure.

I told them about the time Crook stole a crate of absinthe from the royal guard.

It’s a long story, and I told the entire thing. It would take forever to actually write it all out, so I’ll just skip to the ending.

“But you know what real bitch of it was? By the end of the night, every last bottle was broken. We never got to taste one sip,” I concluded with a smile.

Lyra was in tears. Her legs flailed in her raucous laughter. “Oh my gosh! *AHAHA!*” Bon Bon tried to glare at Lyra’s display, but was too busy laughing herself to commit. In fact everypony was laughing at the story. I had such a shit-eating grin on my face. I told a story and everypony loved it. It felt…

…good…

…really really good…

“Oh, Guilty… you’re so silly,” said Derpy. She smiled at me, face filled with genuine joy.

“Okay,” spoke Lily. “I think that’s all the stories anypony can handle.” She was still panting. “If I laugh any more I think I might pass out.”

“I’m so glad you liked it.” I sounded too goofy, looking back. I’d told that story a dozen times, but… never to friends… never to ponies who weren’t paying.

Well… except for Sunny… I told her.

“Of course we liked it. It was hilarious,” explained Lily.

“Well, I’m glad you think so.” I was kind of… genuinely surprised. I didn’t think it would go over well. I don’t know… maybe I was just expecting it to go wrong.

Am I a pessimist?

So after a bit, someone recommended we clear off the table for poker. Everypony helped clear away the remains of the spread. We moved all the platters and plates into the kitchen. After everypony topped off their wine glasses, and took their seats again, Lyra produced a pack of cards.

“You play poker, Guilty?” she asked.

I did my best not to smile. “Yes, Lyra, I play poker.”

“Good,” she said, as she shuffled the cards with her magic. “We’ll try not to shame you too badly,” she said with a smirk.

After that I couldn’t help it. A big shit-eating grin began to emerge on my face. “Oh, how kind of you all. Thank you for going easy on little old me.” I batted my eyelashes.

“Well, we can get pretty competitive,” explained Lily. “We just don’t want you to feel like you were at an unfair disadvantage.”

They had no idea. They couldn’t even fathom how hilarious this was.

“Don’t worry. I’m sure Guilty’ll do fine,” chimed Derpy.

“Well, I’m glad somepony has faith in me.”

“Don’t say we didn’t waaaarn yooou,” sung Lyra.

Everypony gathered around the little coffee table. Carrot Top produced a set of poker chips and began to deal them out. It was a little hilarious, to be honest. The table was far too small to accommodate six players. Everypony was huddled so close together, just to get to the table. The piles of chips had to be stacked high, so they didn’t bleed into each other.

‘Not that it matters, soon all of them will be mine, anyways.’

I was actually planning on losing originally because, well… I’m very good at poker. I didn’t want to be that guy who showed up and cleaned everypony out. Nopony likes to be that guy. That said, after Lyra and them started patronizing me, I felt it was fair game.

So we played. I started out slow, folded a few times, bet on losing hooves, just to get their guards down. I figured them all out pretty quickly. For ponies who claim to be “pretty competitive” they were all fairly easy to read.

Lyra was far the worst offender. She picked up each card as she got it, so I could always tell how strong her hoof was based on how many of the cards she smiled at. Derpy was next, whenever she had a good hoof her eyes would go wide. Lily and Bon Bon were better about it. They still couldn’t help a little smirk every now and then when they had something good. Bon Bon was better at bluffing though, Lily tried too hard to sell it. Carrot Top, interestingly, had a decent poker face. I mean I could still read her, but I doubt anypony else there could.

Geez, I really sound full of myself, don’t I?

So after an assessment of my competitors, I went all out. Well.. not all out. Just out enough to start raking in the bits… err… chips.

It didn’t take too long.

“Crap-fuckin’-Hell!” cried Lyra as the last of her bits made their way over to my pile. “Guilty… I feel like we may have underestimated you.”

I just shrugged in response. I was trying really hard not to gloat about it; it was very tempting. I may or may not still have had a shit-eating grin on my face.

“You’re really good at this, Guilty,” said Derpy, eyeing my sizable pile of chips.

“Yeah really,” agreed Lyra. “His pile’s bigger than his dick.”

“Lyraaaa…” whined Bon Bon, putting her face into her hoof. I chuckled despite myself, and so did Derpy.

“What?” asked Lyra innocently. Lily and Carrot Top appeared as though they were trying to pretend nothing had been said for the last ten seconds. I felt kind of guilty; I didn’t want either of them to be uncomfortable. Then again, I wasn’t the one who said it.

“Anyways,” said Bon Bon in a desperate attempt to change the subject to something other than my genitals. “That just leaves Derpy and Guilty. Lyra, deal the cards.”

Lyra smiled luridly. “Yes, ma’am. I like assertive Bon Bon,” she teased as she nuzzled her lover.

“Lyra. Deal.” Bon Bon was in no mood for Lyra’s shenanigans, clearly.

With a roll of her eyes, Lyra dealt out the cards. I drew two. Derpy drew four. We started betting back and forth. I could tell she was bluffing, she didn’t have much. I, on the other hoof, had three queens, and was feeling pretty good. Derpy had had a run of good luck, and had a fairly sizable pile of chips herself. Before too long, we both ended up going all in.

“Okay, ladies! Let’s see ‘em!” cheered Lyra. This was it… the final round.

“Three queens,” I said, as I laid my cards down.

“A pair of eights!” declared Derpy. She didn’t care that she was losing, she was just happy to play. She was having loads of fun. “Good game, Guilty. You’re really really good.”

So that was that, the game was finished and we—

“Hang on… Derpy, your other cards are all fours,” interjected Lyra.

“They are?” Derpy took a second glance at her cards. “Oh, Hey! Look at that! Still, three fours doesn’t beat three queens,” she said with a shrug.

“Derpy,” I explained, “that’s a full house… you won.”

Her ears shot up. “It is? I did? YAY!” She eagerly grabbed all the chips and slid them to her size of the table. “I win!”

‘Geez… she’s too cute.’ I was happy to lose, to be honest. I’d already made my poker prowess perfectly clear. Not to mention, Derpy got to win. That’s a plus.

“Hey, where did Goldy and Lily go?” asked Derpy. I looked to where the two had been sitting. Sure enough, they were absent. I hadn’t noticed them leave; I was too focused on the game.

“I think they’re upstairs,” answered Bon Bon.

“Aaaw yeah, somepony’s gettin’ bizzay!” said Lyra.

“Actually, I think they’re bickering again,” said Bon Bon, to which Lyra deflated. Bon Bon let out a sigh. “I wish they would patch up whatever’s going on. It’s been worse lately.”

Curious as I was, I didn’t want to get involved in anything as chaotic as a fighting couple. I mean, if Carrot Top and Lily wanted to come in for a session I would gladly help them to the best of my abilities, but beyond that, I was happy to stay as far away as possible.

None of my business.

“So, should we, like… go… then?” I asked. I didn’t know if there was anything else happening tonight. Was ‘girls night out’ over after poker?

“Probably,” replied Derpy, utterly downtrodden. She didn’t like that her friends were fighting, that much was obvious.

Bon Bon sighed. “Well... at least take some food before you leave. I’d hate to force Goldy to eat all these sweets by herself.”

“Dibs on the pretzels!” Derpy shouted.

“Dibs on the booze!” followed Lyra instantly.

Bon Bon’s expression soured. “Lyra... we’re not just going to take Lily’s wine.”

Lyra’s lip pouted in mock disappointment. “Aaaw, but I wanted to get you drunk tonight.”

“Lyraaaaa...” intoned Bon Bon threateningly.

“‘Cause when you’re drunk you let me do naughty things to you.” She put on a great big pair of puppy-dog eyes.

Bon Bon went beet red. “L-Lyra! Don’t just say that.” She shot a quick glance toward Derpy and I. “Th-they can hear you.”

“Aaaaaaw,” Lyra fawned. “You’re so cute when you’re embarrassed.” Lyra chuckled gleefully as she once again nuzzled her girlfriend obnoxiously.

“Lyra, I swear if you don’t— Aahn!” Bon Bon yelped in pleasure as Lyra’s nuzzle gave way to passionate kisses up and down her neck. “Lyra! D-don’t do tha— *gasp*!” Bon Bon’s body practically seized as a delicate hoof traced itself daintily across her cutie-mark.

“Whaaaaaaat? You liiiiiiiiike it,” said Lyra, almost singing. Bon Bon failed to protest. Between the wine she’d already drunk and Lyra’s advances she was definitely ‘feeling the heat’ so to speak. Lyra chuckled incorrigibly. “*HmmHmmHmm* Looks like i don’t need the wine after all.”

Derpy just giggled at the amorous couple’s display. “*hehe* You guys are silly.” Lyra continued to tease and taste her mare unabashedly. Licking and nipping and kissing all along her neck and ear, she managed to make Bon Bon Literally weak in the knees.

Lyra leered at her lover. “Can we go do naughty things now?” she asked.

Bon Bon tried... she really really tried to glare at Lyra’s grossly inappropriate behavior. Try as she might, however, she could only wear a mask of desire. “Fine...*huff*... but grab the daisy cakes.”

Lyra pumped her hoof in the air. “Aw yeah! Cake and sex!”

“Lyra! Now!” shouted Bon Bon, who was already wiggling into her coat. She sounded more desperate than angry.

“Yes ma’am,” cooed Lyra happily. “Bye guys!” she called as she chased Bon Bon out the door.

The two of them make a fairly interesting couple. Lyra seems to revel in embarrassing Bon Bon, but Bon Bon almost seems to enjoy it. Maybe Bon Bon gets off on it. Lyra sure does. They really love each other, too. I mean... really, truly love each other.

Good for them.

“Well, we should go,” said Derpy, still staring at the door through which the lovers had just left. “You gonna grab something?”

I took a glance around, trying to figure out what i could get the most use out of. “I’ll grab the crackers and cheese. Crook loves cheese.”

As I began to gather up my newly claimed hors d'oeuvres, I noticed Derpy kept glancing at the stairs. She let out a sigh and her head fell. “I should probably let them know that everypony’s leaving, huh?”

“Probably.” I found a plastic bag to carry my snacks.

She sighed again. “I’ll be right down.” She disappeared upstairs for less than a minute, and returned with a deflated look on her face. “Alright, let’s go.”

And with that, I began to walk Derpy back home. In all the time it had taken for stories and poker and boozing, the night had become even more still, if that were possible. All the fireplaces and hearths and lanterns had been snuffed, and everypony in town was fast asleep, save Derpy and I. We trotted through that chilly night, leaving wispy trails of our breath and a tiny path of hoofsteps through the snow. The frigid air, the stars above us, it was...

I don’t... I don’t have the word. There’s a word for it, I know there is, but I don’t have it.

Fuck, this is going to drive me nuts.

Well, regardless, I was enjoying myself, revelling in that wonderful icy night. Derpy, on the other hoof, seemed too preoccupied to enjoy the brilliance of the moment. Her mouth kept twisting into concerned expressions, and her gaze kept drifting into the ground. I had a pretty decent guess as to what she was thinking.

“Worried about Ms. Harvest?”

“Yeah…” She trailed off.

There was an awkward little moment of silence, that i decided to break. “Do you, uh, know what it is Lily and she fight about?”

Derpy shrugged. “I’m not sure. I think… *sigh*… I think Lily wants to move in with Goldy.”

“And Ms. Harvest doesn’t want to?”

“Maybe… I just don’t know.” Another moment of silence followed. This time Derpy was the one to break it. “So, why do you call her that?” she asked.

“You mean Ms. Harvest?”

“Mmhmm.”

I pondered briefly how I should answer that. “I don’t think she’d like me to call her ‘Goldy’.”

Derpy cocked her head to one side. “How come?”

“I dunno… just a feeling, I guess,” I lied.

“Aaaw,” lamented Derpy. “I was hoping you two would get along.” Her ears fell a little. “You had fun, though, right?”

“Yeah. It was a blast. I got to whoop everypony at poker.”

Derpy chuckled. “You were super good.” With a flap of her wings she lifted herself off the ground. What is it about pegasi in flight that’s so inherently graceful? Even Derpy, who can be a slightly clumsy flier, looks so impressively delicate. “Looks like I was even better, though,” she taunted, in a hovering show of mock-superiority. She even stuck out her tongue at me a little.

I decided to play along. “Yeah, well… I would’ve won if you knew you had a full house.” I pointed a faux-menacing hoof in her direction.

Derpy’s face twisted in confusion. “Huh?”

“I’m just saying. If you’d known how good your hoof was, I woulda had you.”

She wasn’t following me. “…Why?”

“Because I would’ve known you had a good hoof.”

Still not following. “…How?”

I was actually surprised how easy it was to tell her this. I didn’t stress about sharing my secret with her; I just sort of came out and said it. “Well… ‘cause that’s my special talent.” It came so naturally. I’d hear clients tell me theirs all the time, but it had been so long since I’d actually told anypony what mine was (Pinkie Pie doesn’t count, she figured it out on her own). I feel like it should’ve been harder to say.

I’m glad it wasn’t.

She stopped for a few moments. “…Poker? Really? I’d always thought it was sex.”

I shook my head. “It’s not poker. It’s reading ponies. I can tell when ponies are bluffing.” I squinted my eyes as I realized that Derpy had actually seen me without my jeans on. “How did you think my cutie mark meant sex?”

She shrugged casually. “I dunno. I always thought it was the Camel Sutra or something,” she said with a grin. “But that’s a pretty cool talent. No wonder you’re better than a therapist.”

“Hehehe… yeah,” I agreed. “There have actually been a few times I’ve considered becoming a legitimate therapist. College is expensive, though,” I lamented. It’s honestly not something I’ve considered very seriously. I’ve never liked school in the first place.

“Ugh… I know the feeling. I’m still trying to figure out if I’m going to be able to send Dinky to college.” Derpy took a deep breath to calm herself. I’d touched a nerve.

I decided to try and help calm her. “Meh. College isn’t everything. Hell, I didn’t graduate high school and I turned out okay… at least I think I did.”

Derpy paused. “You always know what to say, don’t you Guilty?” She was smiling again, thankfully.

I shrugged. “I’ve had lots of practice.”

“Hehe... yeah.” She landed beside me, apparently done with her little flight. “Mind-reading is an awesome talent. Much better than mine,” she said.

‘Wait... what is Derpy’s special talent?’

I scanned my memories, looking for some conversation where we’d discussed this. Sadly, I could recall nothing.

‘How...How do I not know this?!’

“Oh, my celestia, I just realized I don’t know what your special talent is,” I blurted rather mindlessly.

She just laughed at that. “Hehe. It’s kinda weird.”

“Oh?” I was curious to say the least.

“It’s... smiling... I guess,” she explained with a blush.

“How do you mean? I mean you have a great smile, of course, but I never thought that that—”

“No not like that. It’s... okay so, what I was a filly, I got picked on alot; I’ve told you that.”

“Uh-huh.”

“Well... I got my cutie mark once I figured out that I didn’t have to let all of that get me down. It’s like... keeping on smiling even when the world wants you to frown.” She blushed at her own corniness.

“...Huh,” I remarked, the picture of elegant conversation.

“I told you it was weird.”

I mulled over this information for a few moments before I responded. “Perseverance is a good talent.”

She grinned. “Thanks, Guilty.”

We didn’t speak after that, not until we made it to her place. As I approached her home I noticed that all the lights were off. “Well… looks like Dinky went to bed.”

“Yeah, she’s a good girl,” said Derpy with a face full of pride. She fucking loves her kid, that’s for sure.

“So this is you.”

“This is me.”

“See you Sunday?”

“Mmhmm. I’ll bring some banana muffins.”

“Awesome.”

“*Heeheehee*… you really like muffins, huh?”

“I guess I do.”

She smiled at me. It was such a warm smile. A smile that was happy to be in that exact moment. “Goodnight, Guilty.”

“Goodnight, Derpy,” I said back.

So, I watched her walk away. I watched her trot down that little stone path to her front door. I wasn’t watching her ass, or anything, I was just watching her. She opened up her home. She turned around. She waved with that big happy smile. She turned back around. She stepped inside. And then she was gone.

And I was alone.

Alone out in that frozen night.

Alone in the snow and the cold and the quiet and the dark.

And what happened next took me complete surprise.

As I stood there, a smile began to form on my face. As I smiled, my mouth began to form shapes, and my throat began to make noises, almost as though I were saying something. Now I was not totally in control of these actions, I swear. My body moved of its own accord. I had absolutely nothing to do with the sounds I made, and those sounds came together to form words, and those words came together to form a sentence that I was in no way ready for.

“Geez... I love that mare.”

Author's Note

Well, it's about time, right? Just so you know, this has always been the intended direction of this story, I've been planning this since the beginning.

Thanks to my editors aquapunkchick, BlackSkulls, coandco, and Jake the Army Guy.

Like, fave, comment, all that jazz. You guys are the best.

Making the Rules

Chapter 14

Making the Rules

Holy shit… it’s morning. I actually passed out while writing.

How far did I get? I need to check.

Oh… so, yeah… that…

It would appear that I have… well… developed feelings for Derpy. Real feelings. Love feelings.

Once I realized what I had said, once my brain caught up with my mouth, I was… understandably distressed.

‘Wait… wait wait wait wait wait wait… what? What?! WHAT?!’

Suddenly that still night didn’t seem so still, and that frozen moment seemed like it was moving at the speed of sound, and I noticed that I was actually sweating out in the snow, and that for the past minute I’d just been staring at a dark house, out in the wind and cold.

And then… I freaked the fuck out.

“Oh no… Oh nonononononononono,” I chanted to myself. ‘This is not happening. This is not happening again. Time to leave Guilty! Time to get out of here! You’re just staring at her house. Time to go, Guilty! Walk, damn you, walk!’

I forced myself out of my trance. I hadn’t noticed that the wind had started to pick up. I needed to get home, fast, or else I’d be caught out in another blizzard. I walked. I walked and walked and walked, chattering to myself all the way, and before I’d even thought I was out of the town proper, I was opening my front door.

I fumbled with my lock; my hooves were shivering, or maybe they were just shaking. I was planning on running upstairs and writing. I wanted to get feelings on paper right then and there. I was so far into my own head right then. I needed to write all the feelings down; I needed to take them out of my head and look at them all. I needed to assess things, badly.

However, something pulled me, rather violently, out of my head. As I rather hurriedly threw open my front door, I was greeted by the fire-lit scene of a certain pink mare’s jiggling backside being impaled by a certain white stallion’s gargantuan rod.

“SOOO BIIIIIIIIIIG!” Pinkie cried as Crook continued to ram himself into her. His chest writhed against her back as each vigorous thrust slapped flesh against flesh in a din of cacophonous sex. Whatever turbulence and confusion had been brewing inside me had been blown the fuck out of my skull by this enthusiastic display of raucous fucking. I was now far too distracted to be having a melt-down.

“Hey, Guilty,” Crook panted without missing a beat. “Is that cheese?”

‘What the fuck is he— oh yeah… the cheese… I forgot all about that.’ “Um… yeah… crackers too. Just gonna… put it in the fridge.” ‘Geez, it fucking reeks in here.’

Pinkie turned her tired face over to see me. Her mane was a frazzled mess, and she was struggling to support the weight of Crook’s massive frame. “*huff*…*gasp*… Hey there… *pant*… Guilty…*huff*… what’s… *gasp*…. shakin’?”

“Uh…” ‘Well this is awkward.’ “...not much. Just… coming back from a poker game. Hehe.” I was face to face with a mare being plowed by my best friend. I’d been in this situation before, but never had a mare tried to exchange mid-coital pleasantries. Crook hadn’t even slowed down, he was still fucking her stupid. She was even drooling a little. The whole fucking thing was impossibly surreal.

“Oh, f-fun…*pant*… I b-b-bet you’re suuuuper DUUUUUUUUUPERRRRRAAAAAAAHH!” Pinkie’s sentence got away from her as she climaxed rather suddenly. Crook neither stopped nor slowed as Pinkie came, he just kept on keeping on. Seeing as Pinkie looked like she’d forgotten what precisely she was talking about, and even that I had been talking to her at all, I opted to quickly slip away and deposit my cheese in my fridge. The kitchen, I noticed, had about a dozen empty beer bottles littered across the counters. No big deal. I’d worry about it in the morning.

“So Guilty!” Crook called from the living room. “You want in?”

“Wooo yeah!” Pinkie cried in agreement. “Let’s make a… *huff*… Pinkie Sandwich!”

I stared at them from over the little bar that separates my kitchen from my living room. I could see Crook’s massive member penetrating her blushing genitals over and over and over.

For whatever reason, something about it just seemed so… clinical.

My penis certainly seemed game, but my heart wasn’t really in it.

“I’ll… pass.”

“S’cool,” responded Crook, still fucking away. “Goin’ to bed?”

“Yeah. Pinkie staying over?”

“S-sure! Sleepover…*huff*… wooooo!” she yelled happily.

“Okay.” I yawned. I hadn’t realized how beat I was. “You guys can take the cloud. I’ll be upstairs.” I started towards my bedroom.

“A’right,” said Crook.

“Good night…*huff*… Guilty!” Pinkie called after me. The sounds of their fucking followed me all the way upstairs. Even in my room, I could hear them faintly. I briefly tried to write but… I was just too distracted. Even thinking about anything was difficult. My mind was just filled with sex. I couldn’t focus properly on the task at hoof.

After several attempts to write a paragraph or two, I gave up. The noise from downstairs was preventing me from processing anything meaningful. So, I took a swig of the whiskey Crook had left in my room, pleasured myself quickly, and went to sleep. It wasn’t even a good bate, I just needed my erection to go away.

Once I knocked out I had no dreams. I simply laid down, sat up, and found it to be morning. That was the first time that happened to me, it was pretty neat. I had the faintest trace of a hangover from the wine and whiskey, but not enough of one to bother me. I picked myself and stretched, taking a nice deep breath and discovering that the air smelled like… syrup?

I pulled myself out of bed and forced my hooves to carry me downstairs. I didn’t feel particularly rested, what with my sleep not feeling like sleep. I found Pinkie working away in the kitchen. By the looks of thing she’d made breakfast for the three of us. There were three little plates of waffles, complete with butter and maple syrup sitting on my table.

“Hey… Pinkie.” I shook my head to try and knock the weariness from it.

“Rise and shine, Guilty! Have some breakfast! I made chocolate chip waffles!” she proclaimed.

I cringed at her outburst. There was the hangover. “Thanks… *ahem*… Pinkie. I take it your date went well.”

“Yes indeedy! Oh my gosh! Crook is so big! I was a cream-filled Pinkie last night, that’s for sure!”

‘Fuck me… her voice is so loud… and high… and it’s soooo early’ “Well that’s…” I suppressed a groan. “... swell, Pinkie.”

“Yepperuni!” she responded far too cheerily. I decided to take a seat and get a good look at the breakfast in front of me. ‘Yes, those are in fact waffles. Hey look, that’s a shot glass filled with syrup, how cute. Oooh, the butter’s even been whipped. Pinkie sure went all out with this—’

My eyes shot open as something very troubling occurred to me.

‘I do not own a waffle iron.’

“Hey uh… Pinkie?”

“What’s up, Guilty? Is the waffle too hot? Is the syrup too cold? Oh, I know! I forgot the orange juice! Wait right there!” She was so full of energy. It was kind of painful.

“No Pinkie, I… well actually some orange juice would be great, but… how did you make these?” I asked.

“Well… first you take some flour, and some salt, and baking powder, and—”

“No… not that… I mean…”

“Oh, you mean the waffle iron.” She reached back into the kitchen and produced the appliance in question. “I never leave home without it.”

I blinked. “You never leave home without a waffle iron?”

She shrugged. “Well, not always never. Just sometimes never.”

I nodded so as to feign understanding. The puzzle of what she had just said was a little too complex for my tired state. Regardless, the waffles were pretty good. I’m not much of a chocolate-chip-guy, to be honest, but they were certainly palatable.

“Do you want whipped cream or jelly beans on yours?” she asked, producing both a bag of jelly beans and a can of whipped cream. I waved a hoof dismissively, trying not to gag at the thought such a flavor combination. Pinkie quickly joined me at the table. The moment she tried to sit down, however, she bolted back upright with a gasp.

“You okay?” I asked through a mouthful of waffle.

“Owie wowie. I don’t think I’m gonna be able to sit down today. Owie-ow-ow.” I noticed she was standing a little bowlegged. ‘Ah… sore pussy.’ “I’m super ouchie down there. Crook is really rough.”

“Did I hear my name?” asked Crook as he emerged from the bedroom.

“Yes, we were just calling you a sexual dynamo of unsurpassed stamina and power,” I snarked.

“Sounds about right,” he said as he made his way over to Pinkie. “Hey, you,” he crooned in a sultry voice. ‘Are they going to start kissi— yes, yes they are.’ Without a second’s hesitation, the two of them began noisily sucking on each other’s faces. They were pretty fucking obnoxious about it, too; they were almost making it hard to eat.

Crook doesn’t have the same hang-ups about kissing that I do. He’s happy to tongue wrestle mares whenever. To be honest quite a few whores don’t mind it at all, but I digress.

“So, Crook, you ready for that manecut?” I asked. Anything to get them to fucking stop.

Thankfully Crook did pry himself off of the party pony. “What?” he asked, clearly confused.

“Remember? Yesterday? Close Shave?”

He just stared blankly at me.

“The old guy?”

“Oh, him,” he said, finally taking a seat. “That guy was serious?” He stared gleefully at the breakfast in front of him.

“Yes… he was… we should go. I don’t want to deal with his shit later.”

“Oh, I love Close Shave!” interjected Pinkie. “He’s super duper nice. Whenever he cuts my mane, he gives me a lollipop!” She made a single effort to bounce on her hooves but immediately regretted it. She winced in pain again and took a bow-legged stance again. “Ow,” she stated simply.

“Nice? That guy?” Crook scoffed. I’ll admit, I was a tad doubtful as well.

Pinkie nodded. “Yes indeedy! Okay, well, he kind of acts like a meanie-pants but he’s really really really nice once you get to know him.”

“I’ll believe it when I see it,” said Crook as he brought the shot glass in front of him to his lips.

I reacted too slowly. “Crook that’s not—!” Crook began coughing as the sweet sticky liquid filled his mouth.

“Oooh! You like to drink syrup too!? I like to put on my cereal.” I just stared at her for a second.

Eventually Crook broke the silence. “Guilty, *cough* is that whiskey still upstairs?”

“As far as I know.”

Wordlessly, Crook stood up and walked toward the stairs. Pinkie and I watched him go.

“Crook drinks a lot, huh?” asked Pinkie, voice showing a hint of concern.

“Yeah, he does,” I said.

I didn’t really have anything else to add.

After that, breakfast proceeded normally. We all ate. Pinkie said goodbye. Crook and she kissed for several minutes before she actually left. I washed dishes. I cleaned up all the beer bottles from the night before. I changed the sheets on the bed. Crook decided to have a beer. I mopped the floor in front of the fireplace… thoroughly. I gave my bathroom a quick scrub. Crook started whining that he had his date with Applejack soon, which I had honestly forgotten about. I told him we still needed to go to Close’s. We decided we’d visit him later in the day. And Crook made his way off to...

Oh, wow, it just occurred to me that he was meeting Applejack at Pinkie’s bakery. That must’ve been awkward.

Wait… not Pinkie’s… she just works there.

Anyways, Crook left for his date. He promised he wouldn’t be long so I decided I’d just wait for him.

And then I was alone again.

And it came flooding back.

There was nopony to put on a face for, nopony to hide my unpleasant emotions from, no audience for my act, and that brought everything bubbling to the surface. It was as though my train of thought from the night before had been frozen in time, and Crook leaving had thawed it.

Now, to clarify, this wasn’t one of my breakdowns. I wasn’t freaking out. Okay, well, yes I was, but it was different. I wasn’t having a physical panic attack, though, I was just worrying like there was no tomorrow.

‘Am I… am I really falling for Derpy? Oh Celestia, this is Sunny all over again. I’m going to want more than her, and it’s going to drive her away.’

‘But what if she feels the same way? Maybe we could actually be together.’

‘And what if it makes her hate me? What if she starts sympathizing with Applejack.’

‘She stood up for me, she at least likes me as a friend.’

‘Or maybe she’s like Pinkie Pie. Maybe she’s just that nice to everypony.’

‘But maybe I’m special. Maybe she actually does have feelings for me.’

“And maybe I’m going to make a fool of myself, and everypony in town will hate me, and I’ll feel uncomfortable just walking the streets of Ponyville, and maybe I’ll have to MOVE ALL OVER AGAIN!” My voice rang through the halls of my empty home, reverberating a shrill echo of my impotent rage. At some point my internal struggle had found voice; apparently I’d been talking aloud to myself for at least a minute or two. My throat was raw from shouting.

“I need… *huff*… cereal,” I said to no one at all. That was just what I needed: something sweet and delicious and totally lacking in nutritional value. I poured myself a bowl of Waffle-Bitz (with a “z”).

It’s basically just little maple-flavored waffle-shaped sugar cakes and it’s amazing.

A bowl, a spoon, some ice-cold milk, and I was ready to chow down. I took a bite. It was nirvana, pure sucrose-laden bliss. “Oh, my Celestia, this is just what I needed.” Apparently talking to myself was a new hobby I had taken up.

So, I munched and crunched and chomped and chewed all the delicious tiny waffles. I daresay they were better than the actual waffles I’d just eaten. Not to discredit Pinkie, it’s just that… well… tiny crunchy waffles are amazing. Actually, in their own way, they’re kind of soul-nourishing. I felt much better after that.

As I washed the bowl from my second breakfast, I heard a knock at the door.

‘Oh, hell, Crook’s back. I really hope he didn’t do something stupid… or evil… or both.’

I answered the door, expecting to find my jackass friend with a big shit-eating grin plastered on his face. “Please tell me you didn’t do something that I’m going to regr— oh…” I found myself blindsided by the arrival of a former client. “Twilight,” I said rather dumbly. I wasn’t expecting her at all. The little lavender mare was standing nervously at my door, blushing all the way up to her ears, as per usual.

“Oh, is… is this a bad time?” she almost whispered. She looked almost ashamed to be here.

And just like that, I was completely in the act. Big friendly smile. Comforting tone. “Unfortunately, Twilight, I’m expecting somepony shortly. I don’t really have time for a session.” Sexy chuckle. “I’m free this afternoon, though. Would you like to make an appointment?”

“Oh I’m… I wasn’t really… I don’t want a… I’m just… Would it be okay if...can just come in for a minute?” she asked, finally.

An escort always has to be careful with this sort of thing. A client asking if they can “just come in” might end up trying to squeeze a session out of you. If that happens it’s best to just firmly ask the client to leave, and to come back another time.

That said, I didn’t think that’s really what Twilight was after. So, with only a tiny bit of caution, I let Twilight into my home. Luckily, thanks to my obsessive desire to clean all messes immediately, any of the mess from Crook and Pinkie’s night was already gone, and my home was perfectly presentable. Now, to be fair, Twilight wasn’t truly a client right then, but she was still a guest, and as such, deserved the same treatment. “Would you like some tea?”

She shook her head. “No, thank you. I’m fine.” She cleared her throat. “Can we… talk?” she asked cautiously.

“Of course. Here, sit.” I motioned for her to join me at my table. She took a seat, and so did I. It felt just like a session, to be honest. “So, what’s up, Twilight?”

There was that blush again. “I just… I wanted to…” She took a deep breath. “… I’m sorry.”

‘Interesting.’ I put on a confused smile. “For what?”

“For… running out on you yesterday. It was… really very rude of me, I was just…” she trailed off.

“Out of it?” I offered.

She chuckled nervously. “Kind of.” She proceeded to stare at my table with a rather dour look on her face.

I felt I had to speak up. “Something’s troubling you.” It wasn’t a question.

“… Is it that obvious?” she asked almost pathetically.

“A little bit,” I admitted.

She just sighed in response.

“If I may venture a guess… I take it this has something to do with that stallion you were talking about last time?”

She nodded sullenly.

“Would you like to talk about it?” I’m not sure why I asked that. Normally something like this would fall under the territory of an actual session but… well… I’m gonna blame it on Crook. I’m sure it was somehow his fault I was drawing the line a bit too far back. Things are usually his fault. That was it.

She sighed again. “I kind of… broke his nose.”

‘Oh shit, that wasn’t just a rumor?’ My eyes must’ve widened, since Twilight was instantly trying to play it down.

“It was a complete accident! I swear!” That wasn’t exactly reassuring, to be honest. If she can break somepony’s nose accidentally, I’d hate to see what she could do if she was trying to hurt somepony. "We were fighting and… and… and one thing led to another… we started tug-of-warring over this… stupid flower pot and then I let go of it and…”

“And he pulled it right into his face?”

“…yeah…”

I laughed slightly, which served to calm her down. Making light of a client’s worries is Escort 101. “And so… you’re in a fight right now?”

“I guess…” She cradled her head in her hooves. “I don’t know. He said he never wanted to see me again, but… he’s said that before.” And there was the sobbing again. “He just… *sniff*… he makes me so upset sometimes.” Okay, this was really something I should’ve been charging for. Stupid Crook. How dare he somehow make me not realize this fact at the time? “I don’t… *sniff*… I don’t know what to do. Part of me… *sniff*… part of me wants to break up with him.” The tears in her eyes were kind of heartbreaking.

“But, part of you wants to hold on to what you have.” She nodded. It was the age old problem: Do I stay or do I go? I’ve have helped literally dozens of mares with this conundrum before. I’ve helped mares realize that they really love their partner despite their flaws. I’ve helped mares realize that they were in a toxic relationships and given them the courage they need to walk out the door. I’ve aided more mares than I care to remember with this exact life-changing dilemma.

And then came the question that always comes.

“What…*sniff*… what do you think I should do?” she asked, eyes filled with desperation.

‘Do I go with a pep-talk approach? She might appreciate that. Do I tell her she has to figure it out for herself? She seems smart, she might just need a bit of confidence. Maybe I could just go the old listen to your heart route. It works more than it should.’ For a few moments I debated which of my many techniques I should use.

Ultimately, however, I just… couldn’t think of anything that seemed worthwhile. I racked my brain trying to come up with the best solution I could for Twilight. For whatever reason (Derpy), I just.. didn’t feel qualified to help.

I sighed heavily and just stared into the air. “I don’t know, Twilight.”

It sure as fuck was not the answer she was expecting. Hell, it wasn’t the answer I was expecting. “*Sniff*… wh-what? What do you mean… *sniff*… you don’t know?”

Now… normally this is not something I would ever do. Maybe it was because part of my brain remembered that this wasn’t a “real” session, or maybe just the whole Derpy thing was getting to me, but… I was just frank with her. Only the barest semblance of an act.

“Twilight… can I be honest?” I asked.

Considering the way she looked, I think she was expecting me to mock her or something, but she responded anyways. “I… I guess so.”

I looked her dead-on. “I don’t know a damn thing about real relationships.”

She looked, understandably, confused. “Wh-what?” She cocked a half smile. She wasn’t sure if I was joking or not.

I continued unabated. “I’m totally serious. I’ve never actually been in a real romantic relationship.”

She kind of gawked at me. Her face quickly became a mask of disbelief. “That can’t… that can’t be right. You’re so… good at this.”

“Yeah well… lots of tutelage and years of practice have made me good at helping ponies with their problems. But… I don’t actually know how to deal with any of it.” I physically relaxed. I leaned back on my fore hooves and stared at my ceiling. “I’ve never actually had to handle any of those problems. I’ve never been in a fight with a lover. I’ve never had to lose a fight on purpose just to stop somepony from shouting. I’ve never had to figure out just how much I love somepony. I’ve never had to break somepony’s heart.” I could’ve kept going since I have a literal decade of experience with other ponies’ problems. “So, I could feed you lines about finding yourself, and figuring out what you want out of a relationship and a dozen other things. But, in all honesty… I am the wrong pony to ask about love.”

Twilight was just flabbergasted. Maybe she was expecting a long winded speech about sticking things out, or a deep intellectual conversation about standing up for oneself. But, whatever she was expecting, it was not this. This was Guilty acting like kind of a dick, and maybe feeling a little sorry for himself. This was not quality escorting. I kind of realized that a moment too late.

She seemed to be at an utter loss for words, and figured that I needed to apologize for that. “Sorry.” I scratched nervously at my neck. It was real nervous, not the fake nervous I’d given her last time. “I’m just… trying to figure some stuff out right now. I didn’t mean to… rant.”

“Nonono, that’s perfectly fine, I just... I didn’t even think…” She wasn’t crying anymore; it looked like I’d distracted her from her own problems for the time being. “How can you be bad at relationships? I mean, you must’ve had plenty of them.”

I nodded. “Yeah… lots and lots of fake relationships. False lovers. Timed temporary trysts. No real girlfriends. No real love. Just… acts.”

GAH! Looking back on it now I was so annoying. I sounded like such an annoying little kid. I was throwing a fucking pity party. I hate that shit. Just the thought of it is giving me an ulcer. I can’t believe Twilight put up with me.

Hell, she actually wanted to help me.

She looked concerned. “Do you… want to talk about it?”

I scoffed. “No, I… I couldn’t.”

“Are you sure?”

I opened my mouth to respond, but… I wasn’t sure. Maybe I did want to talk about it. I was silent for a time. I racked my brain trying to find a course of action that made sense to me. I was already uncomfortable with how much I’d been talking about myself, and I’d barely said anything.

An idea occurred to me. “Tell you what, Twilight. How about we… barter?”

Her eyebrow rose.

“I’ll help you figure out your relationship, and you help me work through my dilemma. How does that sound?”

“That sounds… perfectly acceptable.” She smiled.

My mind was screaming at me that this was a bad idea. I don’t talk… to ponies. ‘Guilty, you could always just talk this over with Croo— Okay, nevermind, that’s a bad idea. Save that for an occasion where you desperately need to have my masculinity questioned.’

“Okay then…” I cleared my throat. This was wrong. It was so wrooooooong. “You’re trying to figure out if your relationship is falling apart or not, correct?”

Her ears flattened on her head. All her emotions were back. The worry, the stress, the almost-crying.

I think Twilight and I are kind of similar. We can compartmentalize. As long as something else is on our minds we can kind of push our emotions off to the side.

Seemed like it, anyways.

She wasn’t as teary this time, but equally sulky. “I… I just don’t know.”

“Well why don’t we start with what the problem is? What specifically does he do that make you upset?”

She sighed, still staring at the table. “A lot of things, actually. He picks fights sometimes. He gets upset when I talk to other stallions; he’s really jealous.” She began to scowl. “He never picks up after himself. He shouts… all the time. He wants to go out all the time, but whenever I recommend a place he shoots it down. And then when I ask him where he wants to go he just says, ‘You pick.’ And I’ll say, ‘I’ve been trying to pick, you’re just saying no to everything!’” She actually began to yell.

“Okay, Twilight, rein it in. No need to shout.” She instantly blanched. She looked mortified. I got the feeling she wasn’t terribly used to feeling this frustrated with somepony.

“S-s-sorry.” ‘Aw… she’s so cute when she’s freaking out.’

“Don’t worry about it. Now… what about some upsides? Why do you like him? What makes you want to stay with him?”

It was like I’d flipped a switch. She immediately started beaming, whether she knew it or not. “He’s…*hehe*… he’s really funny; he can always make me laugh. He’s handsome. He likes to read; I love just sitting and reading with him. He likes to stargaze; that’s actually how we met. And he’s smart, very smart.” She’d painted quite the picture.

Clearly, Twilight really cared for this stallion. Now, one might think that’s all it takes to make a relationship work, but honestly, that’s just one of many things you need. Ultimately, I could not make this decision for Twilight, only she could really know if this stallion is right for her. All I could do was help her... discover her feelings.

“How’s the sex?” I asked straightforward.

There was that heartbreakingly cute blush again, all the way up to her ears. ‘Celestia, she is precious.’ “H-he’s very… gentle.” She sounded happy about that. That might be a turn off for some mares, but clearly it was what Twilight was looking for.

“So he makes you feel good? Physically, I mean. He manages to bring you to climax?”

She nodded, eyes dead set on looking at anything but me. “M-most of the time.”

“Okay.” I cogitated for a moment. The next step is a tricky one. Getting a client to figure out precisely what it is they want can get messy. It’s all too easy to accidentally set somepony’s standards far too high. After some internal debate, I decided that with Twilight the best way to go about it was to be as objective and methodical as possible.

“Alright, Twilight… I want you to answer a simple question for me. Why do ponies date?”

She brought a hoof to her chin. “What we would consider ‘dating’ is actually a fairly recent societal development, historically speaking. Modern dating can most likely be attributed to—”

I couldn’t help but chuckle. “I’m not looking for a term paper, Twilight. I mean what motivates ponies to date? Why do we seek companionship?”

She had to think a little more about that one. Once again, she had quite a wordy answer for me. “Ponies seek companionship so they can reproduce. Every species has to produce offspring; we’re attracted to other ponies so that we can mate and have children.”

I rolled my eyes jokingly before cracking a smile. “Well if you’re just determined to be academic about this...”

“It kind of makes this easier,” she admitted.

“Fair enough. In that case, I’ll just have to debunk your theory.” I cleared my throat meaningfully. “While I agree that that is the case, Twilight, what you are describing is sexual attraction. I am asking why ponies couple themselves. Why do many of us choose to spend their lives with one single pony?”

“I…” I could see the gears turning in her head. “There’s been lots of research on the subject of love. Some theories say that love is actually ‘healthy’ it promotes all kinds of biological—”

This was getting a little silly. “So you decided to start dating because it was ‘good for you’?”

“No, I…” She blushed again. “…I did it because I thought it would be… fun. I thought it would feel good to… to have somepony.”

“Exactly,” I explained. “You dated because you thought it would make you happy.”

“I…” She began to retort, but quickly lost momentum. “…Yes. I would say that... that is correct.” So far so good.

“Okay. So then, what can we assume is the ‘goal’ of a relationship? What should a relationship logically ‘do’ for you?”

She was beginning to catch on. She could see where I was leading her. “A relationship… should make you… happy,” she concluded.

I nodded. “That’s my belief. Would you agree?”

Once again the gears turned in Twilight’s head. “I think it’s safe to conclude that yes, ideally, a relationship should serve to improve your quality of life. In other words… it should make you happy.” Now she was on board, this was working fairly well.

“Okay then, now that we’ve justified that fact to ourselves, I think the next step would be to determine if your relationship does or does not ‘improve your quality of life’.”

Twilight did her best to maintain a professional air. She still groaned a bit. “That seems like the… *sigh*… most logical course of action.” All this fancy wordplay was really just to get Twilight to accept that she had to keep her own interests at heart. Getting a mare to believe that can be more challenging than one might think. Thankfully, Twilight was more than willing to accept a logical argument. “So, how would one… you know… assess that?”

“Well,” I began. “One thing ponies do is write out a list of the pros and cons of your relationship. Whichever list is longer gives you your answer.”

Twilight squinted. “That sounds woefully inaccurate.”

I chuckled. “Well, perhaps you can come up with a more… comprehensive analysis,” I offered.

She nodded. “I’ve got something roughly in mind. Some very basic calculus should give me a better idea of precisely how much my relationship improves my day-to-day life,” she explained.

“I’ll take your word for it.” I don’t have much of a mind for math; I wasn’t ready to talk calculus or whatever.

“Okay so… if I determine that this relationship isn’t making me happy… I should end it, right? Seems simple enough.”

“Well, let’s not get ahead of ourselves, Twilight.” No need to give a guy the axe without giving him a chance at redemption first. “Just because your relationship isn’t improving your quality of life, doesn’t mean that it has to end.”

She seemed confused. “Isn’t that exactly what we were discussing, though?”

“Well, there’s still another option to consider.”

Her ears perked up at that. “And that would be?”

“Improving the relationship itself,” I explained.

She mulled that over with a slight scowl. “That sounds… challenging.”

“Who told you love was easy?” I teased.

“A fair point.” She brought a hoof to her chin. “What exactly would you suggest? How would I improve my relationship?”

“Well, I can’t really speculate on that.”

“Oh?”

I brought my hooves together pensively. “There is no universal treatment for a bad relationship. What helps you and your boyfriend get along better is going to be specific to the two of you. Without a great deal of information, I can’t begin to form a hypothesis.” I was kind of getting into the whole ‘academic discourse’ thing we had going on. It was actually kind of fun.

“Understandable. And I do get your point. Just because a relationship might be faulty now…”

“...doesn’t mean it will always be,” I finished for her.

She grinned. “I think I actually have a plan as to how I’m going to deal with this,” Twilight said.

“Feel better?” I asked.

“Yes. Just having a plan makes things… a lot less stressful, *hehe*.” That lack of stress certainly showed; she’d visibly relaxed quite a bit.

“Okay, so… your turn?”

I groaned. Talking about this shit still just felt… wrong. “*sigh*… I guess so.”

“Well then… what’s going on, Guilty?” she asked.

‘You can always stop now, Guilty. No real reason to keep this up.’

I cringed. Everything about the whole ordeal telling me that what I was doing was just wrong. Should I back out now? Should I go through with it. There was so much I shouldn’t have done already. Was I past the point of no return? Or would this be the straw that broke the camel’s back?

‘Ah, fuck it!’

“Well, lately… in fact only since last night… I’ve sort of been feeling like… I’m… falling for somepony.” It just felt gross saying that. The words were like vinegar in my mouth, just… sour.

Twilight wasn’t following. “And the problem is…?”

“It’s a client.”

She winced. “I can see that being complicated.”

I nodded solemnly. “Yeah.”

“So you only just came to this conclusion, correct?” she asked to clarify.

I nodded. “I spent the evening with her and some friends of hers. When I dropped her off back at home… I realized that… I kind of loved her. I felt like… I missed her already and she’d only just left. I… I wanted to spend more time with her.” Difficult as this was I was doing pretty okay for myself. My breathing was slightly labored, but that was just me struggling with the whole “talking about my feelings” thing. “I still want to spend more time with her. I want to go see her right now. I just want to… be near her.” These facts were becoming evident to me just as fast I was saying them. I hadn’t really had all that much time to ponder this. Not even twenty-four hours.

“You said that you’d never been in a relationship, right? So this has never happened before?” Twilight, Celestia bless her, was putting up with my bullshit in stride. She was doing her best to actually help me.

“This would be the second time I’ve fallen for a client.” That wasn’t entirely true. Strictly speaking, Sunny wasn’t a “client.”

She looked curious about that. “What happened last time?” she asked curiously.

“I moved to Ponyville,” I said tersely. I was already talking about my current problem with her; I sure as fuck was not going to talk about Sunny.

She made an “oh” face. To be clear, that is different from an O-face.

Ha… sex humor again.

Twilight cleared her throat. “So then… what is an escort supposed to do when they fall for a client.”

“Stop falling.” That was usually the routine as I understood it. If you started falling for a client you stopped seeing them, better for a stable to lose a client than lose a whore.

“That seems… harsh,” said Twilight with a scowl.

I shrugged. “It is what it is.”

“So… that’s it? You’re just going to stop feeling that way?”

For a few moments I was silent. I didn’t have anything resembling a plan yet. I didn’t know what I really wanted. I was still adjusting to all this. “Honestly… I don’t know. Part of me feels like I should just tell her that I can’t see her anymore. Part of me wants to just keep it hidden away forever. But at the same time…” I swallowed. “…I’m my own boss now. I don’t work in a stable. I could… I could actually try. I could actually try to be with her.” Is this how I really felt? Is this what I wanted? Did I want to… go for it?

“Hmmmmm...” Twilight rubbed her chin. “That’s… that’s a multivariable problem if I ever saw one.”

“Again, I will take your word for it.”

Twilight giggled. “I just mean it’s complicated.”

I nodded. “That, it is.”

“Well, if you’re unsure as to whether or not you want to actually pursue a relationship. I think your best bet would be to run a standard risk-reward analysis,” Twilight eagerly explained.

I raised an eyebrow. “You say that like I know what it is… and that it’s a thing I can do.”

Twilight laughed and waved her hoof. “Oh, don’t worry. It’s really very basic math. You just assign a hypothetical ‘level of risk’ to each potential outcome, and—”

“Twilight, I dropped out of high school.”

She seemed shocked at that prospect. Ponies often are. I’m fairly well-spoken, but most of that can be attributed to all the training my Madame gave me. Math was never really a priority in the whore house.

“How... I don’t… oh my gosh.” Utterly shocked apparently. She was clearly having trouble wrapping her head around that one.

“Do you have any laypony’s terms for me?” I asked, so as to snap her out of her befuddlement.

“What? Oh… uh… maybe… gimme a second.” I could tell she was trying to come up with a way to explain her idea to me while simultaneously trying comprehend the fact that I had not finished school. “The basic concept,” she explained, “is to weigh each potential outcome from every possible course of action and determine the “best” possible course of action.”

“That honestly just sounds like thinking about it,” I admitted.

“Weeeeelllllll… without the math… I suppose that’s kind of all it is.” Her face fell. I got the feeling she didn’t think she was helping.

To be honest, though, she was helping. Telling me to think about it was good advice. I’d been so worked up because of everything I’d forgotten that… there was nothing actually happening. I had all the time in the world to think things over. I had time to weigh my options, and more importantly she kind of helped me realize that I wanted to. This wasn’t just some problem I had to solve, this was an opportunity.

Maybe… just maybe… Derpy and I could be happy together. Maybe that was… is... a thing that could happen.

“Thank you Twilight. I think I know what I need to do.”

I caught her by surprise. “Really? You have a plan?”

“Yes. I’m going to think about it,” I stated.

Twilight looked unsure. “I’m not going to lie. That doesn’t sound like much of a plan.”

I shrugged. “It’s more of a plan than I had an hour ago.” I actually grinned. “Thank you, Twilight.”

“B-but I didn’t do anything,” she insisted.

“You sat and listened. You offered advice. That’s usually all it takes.” It’s true. Being a good listener is about sixty percent of what I do.

That’s a rough estimate.

“I guess... Well, looks like we both have some homework to do, hehe.” She suddenly blanched. “You… You do know what homework is, right?”

“Oh for fuck— Yes, Twilight, I know what homework is,” I deadpanned.

“Right, right, *hehehe*.” She chuckled nervously again before standing up. “Well, thanks for everything. I should probably go, though. You’re expecting somepony?”

“Yes, that would be best, I think.” As I moved to stand, something suddenly occurred to me. “Oh! Before you go, there was something I’ve been meaning to ask you.”

“What about?”

I was glad I’d thought to ask her about it now. I would’ve been so upset later if I’d forgotten. “A while ago, I was hiking. I came across these… hovering manta rays flying through Ghastly Gorge. Do you have any idea what those might’ve been?”

Her face twisted in confusion. “Were they big grey things?”

“Yeah, that sounds right.”

She shook her head. “That can’t be it.”

“How so?”

“That sounds like mantle rays. But, Ghastly Gorge is not where you should be seeing them,” she explained.

“Mantle rays?” What a delightfully punny name.

“They only live in active volcanoes. They’re magma divers. The only volcano in Equestria is Smoky Mountain. I’ve never heard of them being spotted anywhere else. Maybe it’s an undiscovered migration pattern. It might even potentially be a new species!” Twilight seemed giddy with excitement. “I need to investigate! This could be a major biological discovery! Oh my gosh, I need to go. I have to prepare!” She hastily began making her way out the door. “Thanks again, Guilty. For everything.”

“You too. It, uh… It helped to have somepony to bounce things off of.” I’m not used to thanking clients. It felt weird. Not bad, just weird.

We said our goodbyes and Twilight left. The worry didn’t return when she took off, which was good. Realizing that there was no real deadline, no pressure, no risk of getting caught... it really helped.

So, there I was waiting for Crook to get back. I figured there was no time like the present to try and… well… think. So I thought. I considered. I contemplated. I meditated. It was very therapeutic.

That day I just thought about Derpy in general: what I liked about her, why I liked it, why it made me happy, why it made me want to be with her. There were many muffin related thoughts; those made me hungry… and slightly aroused.

Am I developing a muffin fetish?

A worrying prospect.

Eventually, Crook got home. “Your honor has been defended!” he proclaimed as he burst through the front door.

I could feel a headache coming on. “What did you do?” I asked, feeling an awful lot like a mother about to scold her child.

“Well,” he began, “the two of us had a lovely little lunch date. We ate. We talked. She’s actually pretty nice when she isn’t a fuckin’ bitch.”

“Crook… what did you do?” I intoned.

Crook smirked. “Well, what happened next was pretty fuckin’ great. She actually invited me to her place… to her barn… to the loft… where nopony would bother us.” Crook smiled luridly.

My jaw actually dropped. “She offered?”

“She offered,” he confirmed. I could not fucking believe it. For somepony who makes a point of being the avatar of classical values, she’s apparently pretty loose. I mean, offering an honest to goodness afternoon delight after one date? What a slut!

What a hypocrite!

‘Relish it later, Guilty, you still have something to establish.’

I quickly remembered myself. “So, Crook. What. Did. You. Do?”

“Well…” He could barely contain his smile. “…when she offered me this little afternoon fuck, I casually assured her that my prices were very reasonable. You know, I think I might’ve said it kinda loud. I kinda had to, though, the bakery was just so crowded.”

I was almost in awe. “Oh, Crook. You beautiful stallion, you. Please tell me the whole bakery heard you.”

“Even the big broad behind the register,” he assured me, a self-satisfied grin on his face. “You’re welcome, Guilty.”

I won’t lie; I was pretty satisfied with him, too. All the things he could’ve done? That was about exactly as far as I would’ve liked him to take it. “So what did she do?” I asked eagerly.

“Well first she just asked me to repeat myself. The look on her face was just so… so fuckin’ perfect. Then she just turned beat fuckin’ red and stammered angrily for about a minute. And then she just stormed off. Didn’t even pay for her pie. Oh that reminds me, I forgot my bits so I started a tab for you at the bakery.”

“They let you take out a tab? At a bakery? Do bakeries even keep tabs.”

Crook just laughed. “They do now.”

I rolled my eyes. Okay, not a hundred percent perfect on his part, but fuckin’ A! This was beautiful. Considering how many ponies were there, Applejack was going to get a taste of her own petty, gossipy, small-town, medicine. I couldn’t have asked for a better play on Crook’s part.

“Well Crook, I think you’ve earned a reward for your hard work.”

“Yeah?”

“Yeah… haircut’s on me,” I teased.

Author's Note

Well, there you have it.

Thanks as always to aquapunkchick, Blackskulls, coandco, and Jake the Army Guy.

Breaking the Rules

Chapter 15

Breaking the Rules

So Crook and I went to Close Shave’s. I gotta say, I was feeling pretty good about… well… everything. Crook had pulled a little public shame show over on Applejack, and I was no longer giving myself an aneurism worrying about Derpy. Crook was seemingly distraught, and wore a frown as we made our way towards town.

“What’sa matter?” I asked, my Manehattan accent rearing its head.

Crook’s concerned visage twisted further. “I dunno, Guilty. I’m not so sure about this old guy.”

“You mean Close? Why? Not scared of him, are ya?” I teased.

Crook punched me in the shoulder. “I’m not fuckin’ scared. I’m just worried I might not have both my ears after this. Guy that age? Prob’ly senile. Prob’ly has cataracts. Prob’ly both.”

I scoffed. “Geez, Crook, the guy’s sixty-somethin’, not fuckin’ ninety. Besides, I’ve been gettin’ trims from him just about since I came here. He knows what he’s doin’.”

A wicked grin began to spread across Crook’s lips as he roped me into a half-hug. “There’s the Manehattan Guilty. I’ve been missin’ him ever since mama gave us those fuckin’ etiquette lessons.” He chuckled and smiled warmly at me. “You oughtta drop that fuckin’ ‘proper’ voice, more often; you sound better this way.” He noogied me affectionately.

I failed to suppress a smile. “Fuck off!” I almost chuckled as I managed to throw the stallion off of me. “At least the lessons even stuck for me. She gave up tryin’ ta get you to drop the accent.”

“Hey… it’s part a’ my charm,” he explained. “I’m a package deal, my friend. You take away one part a’ Crook… you lose the whole thing.”

I face-hoofed. “You’re fuckin’ stupid.”

Crook feigned offense. “Well, fuck you too, then.” He shook his head. “Geez, ya think ya know somepony.”

Soon enough we arrived at the barber shop. Crook swallowed purposefully as we stepped in the front door. He’s such an ass sometimes.

I love that about him.

Close was busy trimming some young colt as we walked inside. He snuck a glance at us and immediately scowled. “Where in fuck have you two been? I been waitin’ on you since I opened. I said first thing in the morning, ya fuckin’ mooks.” He returned his attention to the small child who now wore a wide-eyed expression of shock. Close caught sight of the mortified child and cleared his throat. “There’s a sucker in it for ya if ya don’t tell yer dad about that,” he said, tugging guiltily at his collar. The colt’s face immediately lit up as he mimed zipping his mouth closed. “That’s a good kid.” Close chuckled heartily as he continued to snip away at the child’s hair.

“Sorry, Close. I had chores to do. Somepony’s gotta clean up after Crook, here,” I explained.

“Yeah, well… don’t let it happen again. I’ll finish up with Hammer Head, here, you two go take a seat.” He swiped around the scissors in the air and pointed them at us menacingly. “And don’t fuckin’ break nothin’!”

I sighed. “Close, the only thing in your waiting room is a gumball machine and porn.” Crook perked up and the mention of smut and wordlessly left for the waiting room.

“Well, then, don’t fuckin’ break ‘em!” he called as I turned to follow Crook.

As I entered the tacky little waiting room, Crook let out a low whistle, already nose deep in a years old issue of Playcolt. He sat on the opposite side of the room from an awkward looking stallion who was almost certainly the kid’s father. He was blushing rather fiercely, and sat with his legs crossed.

See, this is why I wear pants.

“Guilty, you remember this issue?” spoke Crook.

I eyed the rag in question. A rather attractive orange mare wearing white lace adorned the front. “Can’t say I do.”

“Do you remember, uh… oh, what was his fuckin’ name…?” Crook brought a hoof to his chin as he perused the antique smut. “Salty somethin’.”

“Salty Shores?” I offered. He was an old classmate of ours.

“Yeah. Do you remember how he had that Playcolt he was so proud of?”

I scanned my memories. “Vaguely. Why? Is that the issue?”

He shook his head. “Nah, nah… he got it stolen this one time. That guy Curly took it.”

I cringed. I remembered Curly. Curly was this fucking tool of a child. He was held back two years so he was big stallion on campus, literally. He was a head taller than anyone in school. He also had this bright red curly mane that you could see a mile away. He was a bully, pure and simple. He actually knocked one of my teeth out, once. Crook tangled with him a few times. I don’t think either of them ever had a definitive victory, though. Crook was big, but Curly was bigger.

That said, I certainly had my own personal victory over Curly. After I’d started working at the stable I didn’t go to school all the time, but I did go on occasion. One day in high school, he and his girl at the time had a fight. I happened to be there for the fallout, and I managed to be her immediate rebound. She and I got frisky in a utility closet, and I managed to seal the deal. She told me that even if I was shorter, I was bigger where it counted.

I don’t often win in the size department so I was very pleased to hear that.

Thinking on it, she was actually the first mare I ever went down on.

*Sigh*… nostalgia.

Crook’s continuation of his story snapped me out of my reminiscing. “So anyways, I told Salty that I’d get it back for ‘im. So I march on over to Curly and tell him to fork it over.” He put down the magazine to focus on his story-telling. “So after some back and forth with, he tells me that his mom caught ‘im with it, and took it away. So now I’m goin’ Shit, I told Salty I’d get it back. What am I gonna do now? So get an idea.”

I chortled. “I’m sure it was stellar,” I teased.

“Fuck you, and yes it was. Now, see, I knew that just last week the principal had taken a girly-mag from that girl Primrose.”

I raised an eyebrow. After all, Primrose was a girl. “Why did she have a girly-mag?”

He waved a hoof dismissively. “She was a lesbian. S’not important. What was important was that I knew where she put the shit she confiscated. So, I figured if I couldn’t get back Salty his magazine, I’d just get him another one.”

I face-hooved again. “Why was that your first instinct? You coulda just bought him another one. Or, hell, you coulda even pulled the money outta Curly to buy it. That woulda made the most sense.” Crook is such a fucking half-wit.

He just waved his hoof again. “Doesn’t matter. So anyways… I waited ‘til the old broad left her office, snuck into her desk, opened the drawer with all the confiscated shit in it… and I strike gold.” A shit-eating grin began to spread across his face. “Not only was there the issue I knew about, but six others. There was also a pack o’ gum and an action figure or some shit, I don’t remember.”

Crook cleared his throat a little and shifted in his little folding chair. “So anyways, I nab the porn and I bolt. But, see, know I’ve got a new dilemma.”

“Which one do you give to Salty?”

He brought one hoof to his nose and pointed another one at me. “So I find a quiet spot to mull over the issue.” Read: Masturbate. “And, I’m lookin’ though the magazines and I get to…” he pulled out the magazine again and flipped through the ladies for a moment. “… this page, and what do I find? Two tickets to the Wonderbolts.”

Now I remembered. I have fond memories of that Wonderbolts air-show. I’d forgotten he’d found the tickets in a magazine. I began to nod. “Yeah, yeah, yeah… I remember now. That was this magazine?”

“Yup,” he chirped with a grin. “Right between that ass, and that ass.” He gazed fondly upon the mares in question. “I may just have to swipe this.”

“Behave,” I automatically chastised. “I’m on thin ice in Ponyville as it is; I don’t need my best friend criminalizing the town.”

Crook just clicked his tongue in response.

At about that time the colt from earlier came galloping into the room with a lollipop in his mouth. “All done. Ready to go, dad?”

The stallion in question began to sweat. The poor guy clearly still had an erection. “S-sure thing, son. I’m just going to *ahem* use the bathroom first.” Read: masturbate.

“Guilty! Get out here!” came a bellowing voice from the other room.

Crook was still content to flip through the mountain of erotica before him, so I left him to his devices.

Close was sweeping up the leftovers of his last guest’s mane as I returned. “Siddown. I got a good cut in mind for today.”

I took a seat in the sole barber chair, and the smock floated itself around my neck. “I’m sure it’ll look fine, Close. You’re not half as senile as you seem.”

“Yer such a shit, you know that?” he asked rhetorically as he began to squirt the sides of my hair with his little spray bottle. Soon he was combing and snipping away, and I just closed my eyes and let it happen. I’m never disappointed by how a haircut feels.

I’ve said this before, but it still stands, getting a haircut is like being pampered. Someone is taking the time to do exactly what you want. I suppose it’s not so dissimilar from my service.

Oh, fuck me. I just imagined Close Shave as an escort.

Now there’s an image I didn’t need.

And now I’m thinking about stallions.

Mother fuck.

*sigh*

Anyways…

So, Close systematically began removing the hair from my head. I allowed myself to relax into the trancelike state I often enjoy while being trimmed. Of course, it wasn’t long before Close knocked me out of it.

“So how’s that girlfriend a’ yours, huh? Had any nice little dates lately?” he asked, barely hiding a snicker.

I swallowed audibly as my poker face failed me.

Close began to grin. “You fuckin’ did go on a date with ‘er.” I could sense what was coming, and it was far from enjoyable.

“It wasn’t a date. I just… hung out with her and a bunch of her friends,” I explained, vainly hoping that that explanation would suffice. I knew better, but it felt good to hope.

“So she’s showin’ you off ta all her lady friends, huh? Sound like you’re in deep,Guilty,” he teased, relishing my misery. “I swear, kid. Yer actually gonna fall for this girl if y’aint careful.”

I don’t know what, exactly, but something in my face betrayed me.

And Close caught it.

His grin grew tenfold. “Oh… ohohohohoho… You. Are. Shittin’ me.” He spun my chair around violently. I reeled as I came face to face with him. He was practically gaping. “You’ve got fuckin’ feelings fer this one.” He punctuated his little revelation with a jab to my chest.

I strategically rolled my eyes. “Close, you don’t know what you—”

“The fuck I don’t,” he interjected. “You fuckin’ like this mare.” He began to chuckle loudly. “I don’t fuckin’ believe it.” His chuckles grew into full blown laughter.

I groaned. “Okay… I am… not even discussing this you.”

“Fine,” Close managed between laughs. “Don’t talk, then. Just listen. I got thirty-plus years a’ marriage experience, that your clueless ass desperately needs.”

I buried my head in my hooves through my smock. “Close, I really don’t need—”

My head rather suddenly was jerked back up by a field of magic. “Keep yer fuckin’ head straight, and yes you fuckin’ do.”

I began to plead. “Close, I’m serious. Can we please not—”

“Rule number one,” he began, ignoring my pleas. “Don’t fuckin’ cheat, or I will, personally, beat you shitless.”

“Opening with a threat. Very classy.”

“Rule number two,” he continued, still cutting away at my mane. “If she mentions that she needs something off-hoof. You go fuckin’ buy it first chance you get.”

“Are you really going to mention every conceivable piece of advice you can think of?”

“Rule number three. Learn to go down on a mare. They love that shit.”

I scoffed. “Are you fucking kidding me?” I was almost offended. “Close Shave, I am a professional bed-mate. I have forgotten more about giving head than you will ever know.”

“Language,” he chastised.

“You are so full of—”

“Rule number four: Keep yourself fuckin’ groomed. Keep your hair and beard short, or she’ll think yer a dirty fuckin’ hippy.”

“What is it with you and long hair?”

“It’s for girls. That’s what.”

“How very close-minded of you.”

“Rule number five,” he proceeded. “Shut the fuck up. I’m serious about that one. Half the time not saying anything when your girl’s fuckin’ upset is the smartest fuckin’ thing to do.”

“You’re enjoying this far more than you should.”

“Rule number six.” He put down his scissors and undid my smock. Our eyes met through the mirror. “Be yer fuckin’ self, kid. Make her fall for you, not somepony you think she wants.” His expression was… earnest. He really meant that last one.

I inspected my new haircut. I looked pretty sharp, not that I expected anything less than that from him. “Thanks, Close.” I gave a somewhat defeated sigh. “I suppose I owe you for the advice, don’t I?”

“Fuck yes, you do. That’s some triple-digit-valued advice right there. Let’s see a fuckin’ stack, Guilty.”

I handed him thirty. “That’s for me and Crook.”

He glared at me.

I stood my ground. “Don’t push your luck.”

He grunted menacingly and took the bits. “You’re such a fuckin’ ingrate it’s disgusting, Guilty.”

I ignored him. “You want me to get Crook out here?” I asked.

“Yeah, get yer boyfriend. I’m gonna make ‘im look like he fuckin’ oughtta look.” He seemed bizarrely hostile towards Crook. Then again, they’d almost come to blows the day before, so I suppose it wasn’t totally unjustified.

I found Crook in the waiting room right where I’d left him. He’d dropped his issue of Playcolt for what appeared to be a lingerie catalogue of some kind. “Crook, time to take some off the top.”

He looked up at me and his eyes shot open comically. “Woah… yer alive. I thought that old guy’d killed you for sure.”

I rolled my eyes. “Ha Ha… now get out there before he starts shouting.”

He pulled himself out of the chair. “You actually don’t look half bad, Guilty,” he remarked. “Maybe the old guy’s not totally blind.”

I rolled my eyes again. “He’s not blind at all!” I protested. “Just sit down and let him trim you, aright?”

He waved a hoof reassuringly and stepped out of the waiting room.

I had several minutes to myself, so I decided to have another little think.

I thought about Derpy, of course. I thought about what it would be like to have a relationship with her, just the technical details of the whole thing. I’d almost certainly have to stop charging her for sex. Would she move in with me? Would I move in with her? How would Dinky even come into the equation? There were a lot of loose ends to tie up with this sort of thing, and I wanted to make sure I considered everything before I made a decision about the whole thing.

I didn’t have long, otherwise I would’ve thought about quite a bit more. When Crook returned he had a big smile on his face. “Whadaya think?” he asked, clearly expecting approval. He looked pretty snazzy, I will say that. His hair was short and neatly cut, but was styled up and back with a bit of mousse or gel or something. “Not bad at all.” I gave an approving nod. “You good to go?”

Crook nodded and we took our leave, passing Close on our way out. “You think about what I told ya!” He shouted at Crook.

“Yeah, yeah…” replied Crook, uninterested.

Stepping outside, I turned to Crook. “What was that about?”

He shook his head. “Nothin’ important.” He wasn’t looking me the eyes. He was hiding something. He can never look me in the eyes when he’s hiding something

I raised an eyebrow. “Yeah?”

“Yeah,” he said rather finally. I decided to drop it.

“So what’s the plan?” he asked. “You’re free all night, right?”

“Yeah. Early one tomorrow, though, so don’t bring anypony over tonight.”

“Fine, fine. Hungry?”

I decided that I was. “I could eat.”

Truthfully the rest of the day was largely unveventful. We ate, we drank, we laughed and had fun. Crook expressed multiple times his desire to go grab Pinkie Pie so we could fuck her together. Every time, I reminded him that I had an early client.

Time flew, and soon we both found ourselves exhausted and ready for sleep. We shared the downstairs bed again, and I slept like a log. The next day morning was really no different. The two of us had years of catching up to do, we just talked for hours.

The time for my appointment grew close, and rather than hide upstairs again, Crook decided he’d get out of the house. It was one less thing for me to worry about, so I was perfectly happy with it. Once he left, I made the bed and put on music and tidied my house in peace.

So, I waited for my client, another first-timer. I’d received an anonymous message several days prior. It was written on a scroll, which was interesting. Cryptically, it didn’t have anything written on it except a date and a time, so I was rather curious to see who was showing up. Eventually, the much-anticipated knock came at my door and, act prepared, I eagerly answered it.

And for the second time in as many days I found somepony I was not expecting standing at my door. “…Zecora…” My act was shattered. I lost all semblance of professionalism as I couldn’t help but freeze up. I’d put all possibility of bedding Zecora out of my mind just days ago, so I was totally unprepared for her presence. But there she stood, golden jewelry glittering in the sun, a brown cloak draped over her back, a satchel at her side.

She smiled… uncertainly. There was a hint of worry or doubt hidden in her features. She pretended not to notice my utter lack of composure as she greeted me. “Greetings, Mister Guilty Pleasure, buyer of my escort’s treasure.”

I had to catch up. I had to get back in the act. ‘Zecora’s here, the mare who is theoretically forbidden from having sex. She’s here. She’s here, now! Say words, Guilty. Do things! Get it together and greet your fucking guest!’

I shook my head slightly. I had to snap out of my shock. I forced a smile. Ears up. Friendly voice. “Zecora. What a pleasant surprise. Come in.” Bid entrance. “May I take your cloak?” Casual physical contact as I remove her cloak. Usher to table. “Please take a seat.” After having been dropped, my act came back in force. I was on top of my game, every movement and action and word considered carefully yet quickly. I was in the zone.

“You are sure you don’t mind? You are truly too kind,” she quipped, seating herself at my table.

Reassuring tone. Calming smile. “Of course I don’t mind, Zecora. Would you like something to drink? Tea? Hot chocolate?” She simply shook her head. “Well, I’ll leave the kettle on, and if you change your mind you’re welcome to it,” I said with a grin. A real grin. The thought-lost possibility of sleeping with the drop-dead sexy Zecora was quickly becoming very real.

“I assure you, you don’t need to,” she said, her luscious verse like candy for the ears. “Please sit, if it’s not too much fuss. There’s much that I wish to discuss.”

I quickly put a kettle on the stove and obliged her request. Giddy as I was, I managed to notice the sullen look on her face. She stared heavily at the table’s grain, a scowl adorning her banded face. I opted to continue with my normal line of questioning for the time being. I would address all her worries in time. “I’m glad you came, Zecora.”

She gave a single nod, and nothing more.

I cleared my throat. “Before we get started, may I ask you a few questions?”

“I would surely be remiss, if I did not allow you this,” she responded, her head still bowed and expression still sour.

“First, is it okay if I call you Zecora?” I asked plainly.

She cocked her head to the side. “I do not see why that would not be.” The question seemed to baffle her slightly. If nothing else it replaced her sour expression with a confused one.

“Very good,” I said with a grin. “Second, there is, of course, the matter of payment. Have you prepared any bits?”

“I’ve many coins stored. I can surely afford.” She has a rhyme for everything. I love it!

With any other guest my next question would be how she had heard of me, but I already knew the answer to that. I’d told her myself, after all. So, I moved on the my final, and favorite, question. “Excellent. Well in that case, Zecora… what can I do for you?” I omitted my normal, suggestive, tone in lieu of a slightly more concerned one.

After several silent seconds, she spoke. “I am… unsure, Mister Pleasure.”

‘Well that’s… a new one.’ I’d honestly never had a client say that. When a mare comes to me she usually has at least some idea of what she wants: a lay, a date, a conversation, something. I didn’t even have a proper response to that. “Ummm… what?”

She brought a hoof into the table to rest her troubled head. “If I may be sincere… I am not sure why I’m here.” She gave a somewhat defeated sigh, and sunk her head further into her hoof.

My mind was scrambling. ‘What’s the angle, Guilty? What do we know? She’s a gorgeous zebra mare with an ass that won’t quit. Okay, that’s fun to think about but it probably isn’t relevant. She’s an apothecary. Also, probably not relevant. What do we know about her personal life? She lives in the Everfree forest. She’s a shaman—’ It hit me. I’d been so happy to have her in my home that I’d forgotten what I’d learned just two days ago. She wasn’t supposed to be in my home. She was supposed to be refraining from pleasures of the flesh.

So, I slowed down. I’d been a little too eager, as I often am, and I needed to take things at a more delicate pace. ‘Okay, Guilty, how to go about this? A direct approach? Cut to the heart of the matter?’ I swiftly decided that it was probably the best course of action to reveal what I know, at least to some extent. “Is that because you’re a shaman?”

Aside from the slight perking up of her ears she gave no indication she’d even heard me. After several seconds she spoke. “Well, you seem to know more than you look. Spending some time with Twilight’s books?”

“A bit,” I responded coolly. “You’re not meant to partake of my more… unsavory services, correct?”

“Carnal joy is, to a shaman, taboo. However, I find myself… drawn to you.” She pronounced it ‘shah-min’; I’d been saying ‘shay-min’.

“Well, in that case, Zecora, what can I do for you? We can chat, if you like. I can prepare some refreshments, as well.” I maintained an amicable atmosphere. Best not to make her feel pressured.

“A bit of company sounds nice to me. I don’t often get guests in Everfree.” A hint of a smile pulled at her lips. Progress.

I couldn’t help but smirk. “Well, shall I get some tea for my guest then?”

Zecora chuckled. “You have convinced me. Go get your tea.”

We sat and drank for a while. We chatted about the town and her customers. We talked about her homeland and her family. We spoke of the Everfree Forest, in all its terrifying wonder; I learned quite a bit more about timber wolves than I ever really wanted to.

On a side note, I only filled her glass of tea once, but it didn’t run out. It didn’t seem like she was sipping daintily or anything. I don’t know. It’s probably not important; it just seemed weird.

Eventually, the opportunity presented itself for me to ask her what, exactly, a shaman was.

She cringed. “I’m afraid my answer’s not so plain. There’s quite a bit I must explain.” She took a deep breath as she prepared her explanation:

“Not that much is known about the magic that we hone.

Zebra magic’s not so clear as the magic ponies rear.

To learn this cryptic art, in meditation we take part.

To truly master zebra magic, one must accept a fate most tragic.

A shaman, as we call these masters, must place themselves into disaster.

A pilgrimage, they undertake, to a land with much at stake.

They cleanse the chaos from the land, so that order once more stands.

Once this cleansing is complete, the shaman’s managed quite a feat.

They return to their place of birth, and are entitled ‘Guards of earth’.”

Her poem was rather moving, there was such weight and emotion in her voice it was hard not to feel… I don’t know… Impressed? Still, that didn’t stop me from analyzing it in my way. First of all, she referred to shamans (is that how you pluralize it?) in the third person. She all but admitted to being a shaman a moment ago, so there was definitely some sort of hang up there. Most likely she wasn’t feeling so shamanly(?) lately.

The second connection I made was this ‘land’ she referred to. Honestly it sounded a bit like the Everfree Forest. That place is a mess. As far as Equestria is concerned, that place is probably as chaotic as it gets.

Lastly, there was just something I noticed. She mentioned something about a ‘Guard of Earth.’ Honestly, that just sounded interesting.

So, I had a lot of new information to work with. ‘Should I ask her some more about Everfree? Should I focus on the fact that she isn’t talking about shamans in the first person? There are so many potential courses of action.’ I had to act quickly, I couldn’t just sit there and contemplate my lines forever. I opted to keep things simple. “So you’re trying to… fix the Everfree? That sounds… hard,” I said with a chuckle.

Zecora chuckled herself, and an actual smile spread on her face. Rather than respond she nodded again.

“So that’s what you’re doing out there? Trying to… bring order back to Everfree Forest? Wow, that’s… amazing.” I figured acting impressed wasn’t a bad move. Flattery seldom backfires in my line of work.

“It’s a quite tough job, to be sure. But I shall make that forest pure.” I saw a hint of a blush in her cheeks.

‘Okay, we’ve buttered her up a bit. Time to ask some tougher questions.’ “So, Zecora…” I took a sip of my tea. “… why exactly isn’t a shaman supposed to… you know… have sex?”

She winced. I expected her to. “The elders say: lewd acts, a shaman’s mind, distracts.”

I mulled that over. “That seems… I dunno… odd.”

She cocked her head, expecting elaboration.

I fed her some lines I thought she might want to hear. “Well I mean. I would think that not being able to… you know… would be more distracting than anything. It would for me, at least.” I shrugged. Hopefully I’d taken a stance that would ingratiate me a little more. Every bit helps.

Zecora scoffed angrily. “Exactly.” I was expecting a second verse, but there almost wasn’t one. She caught herself and threw together a rhyme. “That’s as I see.”

A bit forced, in my opinion.

“So, do you find yourself distracted, Zecora?” Raised eyebrow. Suggestive smile.

“There are times, I find, that it fills my mind.” No embarrassment, no blush. She wasn’t ashamed of her needs at all. It’s somewhat admirable to admit that you’re horny.

Well… at least in her circumstances.

I cleared my throat. It’s good to do before asking a delicate question. “If I may ask, Zecora, why don’t you just… do it? What’s stopping you from just finding a handsome young townpony and doing what comes natural? You’re more than attractive enough to grab any stallion you want.”

She blushed again. “N-no matter how tempting that prospect may be. Such actions are truly forbidden to me.” I think she was blushing at the compliment more than my hypothetical.

I cocked my head. “If you get laid are you going to suddenly stop trying to fix the forest?”

“Why would I stop? Such a task, I won’t drop!” She actually shouted at the prospect.

I instinctively scooted back a bit at her outburst. She promptly apologized.

“I’m serious, though,” I explained. “If it’s not going to stop you from completing your quest, why does it matter if you find yourself a little companionship?”

She frowned. “If the elders were to discover—”

“How would they?” I asserted. “They’re a nation away. Would they really send some poor zebra all this way just to find out if Zecora got a little amorous?” It was time to press her; I could feel it.

She was starting to get flustered. “Th-though, unlikely this seems—”

“Even if they did, they’d have to find the exact stallion with whom you’d done anything.” I wasn’t going to let up. These were doubts she already had, I was just giving them a voice.

“N-not impossible, this would be, c-considering…” She racked her brain to find a rhyme. It wasn’t even a particularly hard one, but she was a bit shaken.

“And if, of course, this stallion’s job were to keep the secrets of those who came to him, it would be literally impossible, wouldn’t it?” I teased suggestively. She wanted to respond. She opened her mouth but no words came. I continued to grin like a bastard. “Hypothetically, of course.”

Her mouth closed. She stared at me for a second before her lips curled into a wicked smile. “You make quite an argument, Mister Pleasure.”

I didn’t break my expression. “That didn’t rhyme,” I said, playfully.

“That did not rhyme,” she mirrored almost darkly. This was suddenly taking a pretty bizarre turn. Her gaze was low. Her breath was slow and deliberate. Her mouth was scrunched into a… I dunno, it’s hard to describe. She seemed almost disappointed at something.

I was at something of a loss. I had the feeling I’d stumbled into something that was a bit larger than anticipated. I’d been playing the role of the tempter, giving her every reason to give in to her urges. It’s a bit of a risky strategy, but a valid one in given the situation. When a mare wants it, and she knows she wants it, sometimes all it takes is to convince her that nothing will go horribly wrong if she gives in a little. I was worried I’d overplayed my role, come on too strong and made my seduction obvious. Perhaps I’d made her upset. “I’m sorry, I haven’t offended you, have I?” I asked in a concerned tone.

She sighed. “No, Guilty. I think I have been offended for some time now; you simply helped me to realize it.” ‘Oh… well… sounds like I did good. Works for me.’ Thinking on it, she had probably all but made her little revelation (whatever it was) without me. I threw a bit of doubt onto her long held beliefs, but I’m sure there was already plenty to be had.

Still, I decided to air on the side of caution. “Are you okay, Zecora?”

She let out a sizable sigh of relief. “Apparently,” she said, almost surprised.

“Are you okay?” I asked again, trying to get on the same page. She’d clearly had some sort of breakthrough while I was trying to break the ice, and I wasn’t exactly sure what it was.

She looked me in the eyes. “Guilty, I have been speaking in rhyme for over eight years now. I was expecting breaking that practice to be a bit more… climactic.” She looked somewhat disappointed.

“Would you have preferred to… I don’t know… explode?” I joked.

She laughed. “Nothing so drastic, I just… I did not expect prose to come so naturally,” she admitted.

“So… feeling good then?” Things honestly seemed to be going too well. I was torn between my teachings as an escort and my baser instincts. I learned that when things are going well, roll with them. Still, some part of me was suspicious that she was going to completely lose her shit at the drop of a hat.

You inevitably service some crazies in my line of work. I’ve had some bad experiences.

“Good? Yes, I suppose I am,” she decided. “I feel… relaxed. For the first time, in a long time, I do not have to plan everything I say. It is… nice.” She smiled widely. I reciprocated.

It was then that I noticed a wicked gleam in her eye. “Do you know what I would like to do?” she asked, almost hopping in her seat. “I would like to drink some beer. Do you have any?”

I chuckled. She sounded so innocent. “Yes, I have some beer. Let me go bring you some.” I left my seat and made for the kitchen, as Zecora gave a gleeful little click of her hooves. I took a quick inventory. I’d forgotten how much Crook had drank, but he stuck to the cans. Thankfully, I still had some brown ale in bottles.

I returned with two open bottles of ‘Trottingham’s Finest’ and placed a bottle in front of each of us. “I take it you haven’t had a drink in some time. Was that another rule for you? No alcohol?”

She nodded, but her attention was on the brew in front of her. “I have not had beer in some time. I used to partake quite often.” She tittered. “I was quite the rabble-rouser.”

“You’re not going to start a riot in my home are you?” It wasn’t a great joke but she laughed anyways.

Zecora grinned. “No, Guilty, I suppose I just feel like breaking some rules.”

I had a bit of a flashback. Crook’s said that to me quite a few times, and almost every one of those times has a story tied to it.

Zecora took a hearty swig of her beer. “Not so strong as I would like… but good flavor.”

I took a sip myself. I actually find myself loving this beer. I bought another case after Crook left.

I digress.

For several minutes Zecora took happy sips, savoring every drop. I found myself thinking about some of my adventures with Crook. We used to break the law all the damn time. Crook shoplifted a lot. He never really did it for the thrill, he always stole stuff that he wanted: booze, porn… that’s actually about it. He also had a bit of a knack for dice. He made quite a few bits back in the day.

I wasn’t much better. I was always his little accomplice. I’d be a distraction or a look-out or whatever he needed.

I actually started thinking about this brief period of time where Crook was an… well… there’s no other word for it: enforcer. After about a year of working in the stable, Crook was approached by some old schoolmates who wanted him to “put the hooves to somepony,” as it were. He actually did it a couple times before the madame found out and chewed him out. He stopped after that.

I think the two of us are probably lucky as hell to have it as good as we do. As odd as things are now between Cherry Smile and me, I do have to thank her. She was good to me… to us. If it wasn’t for her Crook would almost certainly be a career criminal. And me?

I don’t even know.

I take that back, I know exactly what I’d be.

Geez…

So, anyways…

Fuck me. Where was I?

Right. The beer.

Zecora finally finished off her drink. With a contented smile, she brought a hoof to her chest. “I have missed this warmth.” Her face began to redden as the booze flowed through her. “I enjoy this drink. It’s much smoother than that of my home.”

I nodded in agreement. “It’s good beer. Can I get you some more?”

She looked unsure.

“Perhaps… something a little stronger?” I offered.

Her devilish little grin was priceless.

I stood to move. “I’ll make you something.”

I took a quick stock of my liquor cabinet. I had a lot more to work with after Crook’s recent purchases. Looking, I wasn’t sure exactly what to make her. ‘Okay, what did she think of the beer? It was weak, but smooth. So maybe something a bit stronger but no less smooth. A stronger beer would be perfect. Hmm… even with Crook’s purchases I don’t think I have anything like that. Maybe something sweet? No, she seems to like the taste of liquor, no point it covering it up. This is tough. A cocktail with beer is propably my best bet. What do a have? Tomato juice. Nah, a red-eye’s pretty out there. I’ve got plenty of hard liquor. I could do a boilermaker or a dog’s nose. Hmm… not feeling it. I’ve got… wait, is that fucking champagne?’

I almost did a double take. I still do not know where that came from. I must’ve had it for a while since it was pretty dusty. I guessed it got moved in the cabinet’s recent re-organization. Now, I should probably note that I feel champagne is a celebratory drink, something for special occasions. That said, it was just what I was looking for. A black velvet would be sweet, yet savory, and a bit stronger than the beer.

I poured a bottle of beer into two glasses, and topped them off with champagne. Bubbly, flavorful, exotic… splendid.

I returned to Zecora, who’d been taking the time to admire my home. “I think you’ll enjoy this. It has a unique flavor.” I placed the glass in front of her. She carefully examined the golden brown liquid, before ultimately giving it a testing sip. Her face positively lit up when it hit her tongue.

“It is sweeter than I expected.” She licked her lips and took a large swig. “What is this brew? Do I detect grapes?”

“It’s the beer from before with some champagne,” I explained, taking a sip myself. “Do you like it?”

She nodded. “I have heard of champagne, though never tasted it before. There are no grapes in my homeland.” She took another sip, as the liquor started to make its way to her face.

We drank for a while. We ended up finishing the champagne, which Zecora took quite the liking to. She told me some stories about her homeland. Her stories sort of reminded me of my own. She seemed to have raised some hell in her hometown. It also sounded like she’d left behind a whole lot of friends when she came here, which I can also relate to.

She ended up talking to me about Applejack, oddly enough. Apparently she took issue with Zecora when she first came to town as well. Also she was apparently shrunken down to a diminutive size thanks to some magical plant. This amused me.

So after a few back-and-forths and we ran out of stories, Zecora was seemingly elated. The way she was smiling told me she hadn’t had this much fun in years. She was laughing to the point of tears. “Whoo… I think… I am glad that I came here, Guilty.”

“I should hope so.” For a moment my gaze met hers, and I could see it. That special mix of hunger and a tiny bit of shame that tells me a mare is ready. ‘Time to move.’ “So, Zecora… you said you missed the warmth of liquor, yes?”

She nodded, cocking her head to the side. She seemed unsure as to where I was going with this.

Little did she know, I’d had a brilliantly corny line prepared for the past half-hour.

“Are there any other… warmths… you’ve missed? Is there any way at all I can… warm you up?” Shit-eating grin. Exaggerated raising of eyebrows. Sometimes a bit of humor is just the tail-raiser you need.

Zecora tried, and failed, to contain her laughter. She unwillingly fell back in shrieking mirth. It was more of a reaction than I’d expected, but by no means a bad sign. She managed to squeeze out a few words in the midst of her hilarity. “I…I have been waiting for quite some time. And when… and when you finally ask… you ask…” the rest of her thought was lost as the giggles returned.

When her mirth subsided, she let out a long relaxed sigh. “I think the time has come for you to rut me. I’m worried if we keep talking you may send me into another fit.” She seemed determined.

‘How very forward. Not going complain. Makes my job easier.’ I stood, adjusting my newly style mane for a bit of flair. I grinned knowingly at her. “Come,” I instructed. I love when I get to say that. It’s a single word, but it holds so much promise.

She obliged, almost rushing to her hooves, as I trotted off with no small amount of swagger in my hips. I led the eager zebra onward, swishing my tail and flaunting my goods. By this point she wanted me. Everything was coming together. All that remained was the best part.

I won’t lie; I was just as eager as Zecora. The idea of digging into that gorgeous zebra was just so appealing. The moment I led her through the bedroom door she swiftly began to shed her jewelry. “Someone’s very eager,” I teased.

She laughed in response. “It has been eight years, Guilty.”

‘A fair point.’ “Well, before we begin, some rules,” I half-insisted. It’s important to never skip the rules. “Rule one: no kissing on the lips.”

Zecora’s mouth twisted into a worried little frown. “A shame,” she lamented. Her features softened slightly. “But… acceptable.”

“Excellent. Rule two: If either one of us says ‘stop,’ we both stop. No exceptions.”

“Of course.” She nodded.

“Very good,” I smiled just as she got the last of her jewelry off. “Then, let us begin.” I moved swiftly. In my experience zebras appreciate it when you make the first move. I hate to stereotype but it’s served me well. Before she could even make it to the bed I attacked her neck with a series of kisses.

“AH!” she cried as pleasure rocketed through her. Each kiss elicited gasps and shudders and exclamations of “Oh, Guilty!” I gently guided her towards the bed as my assault continued. The two of us clamored up onto the cloud, Zecora practically tripping over herself. I embraced her as we did, but as soon we as hit the bed Zecora spoke up. “Guilty… I… I think I’m going to fi—” she trailed off as her body literally shook with orgasm. Her muscles trembled as her whole system reacquainted itself with climax. Her face was a mix of surprise and delight as she shivered and squirmed and writhed in what I assumed to be her first climax in nearly a decade. I couldn’t help but smile. I love when a mare comes so soon. It usually means she’s going to come a lot.

She spoke as drool began to trail down her lips. “I am… *huff*… sorry, Guilty. I have finished *huff* already.”

I giggled. Her blushing, drooling, post-O-face was cute. It made me wish I’d actually seen it while she was coming. “Zecora, trust me. You’re going to ‘finish’ a lot more, before we finish. After all, I’m a professional.”

“Truly?” she asked, apparently non-believing.

With a delicate guiding hoof I rolled her onto her back. “Truly,” I said, parting her hind legs and catching an eyeful of her gorgeous marehood.

If I may be candid, Zebra pussy is a beautiful thing.

And Zecora’s was no exception. Cute, little black lips, dripping with desire, parting ever-so slightly, giving a peek of her tight pink entrance. All smack in the middle of her supple, round, banded ass.

I’d hang that pussy on my wall.

Wow, that actually sounded like something a deranged serial killer would say.

Uh…

I’d hang a photo of that pussy on my wall.

Yes that’s much less terrifying.

Zecora cocked an eyebrow as I licked my lips. “Are you—?” Her question was cut off as I dove in. I gave a long, firm lick along the length of her sex, giving a purposeful flick across her stiff little clit. She was in heaven, and so was I. Her eyes rolled back and her back arched as another orgasm claimed her. She was insanely sensitive; I suppose eight years will do that to a mare.

Rather than give her a chance to catch her breath, I decided to make good on my promise to help her ‘finish’ a lot more. I licked, and slurped, and kissed, sucked, and lapped over and over, her wanting flavor attacking my senses, as my tongue attacked hers. I felt her legs cross behind my neck as a pair of hooves gripped my head, pulling my hungry muzzle into her equally hungry entrance.

Her words came ragged and forced. “Do not… *huff*… stop!” she commanded, desperate for more.

This was… perfect. My client was a gorgeous, interesting, friendly, and incredibly sensitive zebra mare. I was on the most comfortable bed I’ve ever known, with my tongue inside her. She was wet and wanting and delicious. This was a great session. This was one of those sessions that reminded me why I do what I do. I was making somepony feel good just for the sake of making her feel good, and that’s what I’m all about.

And I was enjoying myself just as much as she was. I was practically bursting out of my jeans, just reveling in the flavor of a wanting mare. I began to trace my hooves long the insides of her legs as I proceeded to eat her out to my heart’s content. It drove her wild. Her hips spasmed and gyrated; her muscles twitched beneath her striped skin.

“My g-goodness, Guilty. Wh…where did you *nnf* learn this.” I looked up at her face. She was chewing her lip furiously as wave after wave of carnal joy engulfed her. A thing of beauty. Mares are most beautiful when in the grips of passion, I feel.

I allowed her a brief break from my tongue as I took a moment to speak. “Have you never had a stallion go down on you before?” I asked. Rather than keep her dripping pussy wanting, I slid a hoove up to clop her gently.

She shook her head. “I h-have not.” She threw her head back as every muscle in her feverish body twitched. “I have n-never known pleasure like this.” She let out a long and contented sigh.

I smiled as I toyed with her still-warm sex. “Well, have you ever been with a stallion as… experienced as myself?” I asked.

She shook her head again. “No… For some, I was their first mare.”

“So, you were just a filly, playing with colts?”

She nodded.

“Well, today, you are a mare, and I would like to show you how a stallion does things.”

She grinned devilishly. “I can not waaaaiiiit!” I kissed my way down the inside of one leg, placing a peck on each stripe as I made my way back to her needy lips. “M-More?” she sputtered.

“If you like,” I answered, my mouth hovering just above her sex.

“I…” I tried to read her, but her face betrayed little emotion beyond her understandable ecstasy. “… I would like to join you,” she said, finally.

“Alright,” I slid myself to the edge of the bed. “I’ll grab a potion real quick, and then you can… reciprocate.”

She nodded tiredly before collapsing backwards into the sheets.

I was loving this. I practically skipped to my little chest. Hell, I barely noticed how bad the blue little phial tasted. I was In bed with Zecora. Zecora! I’d had a boner for this mare since the moment I’d seen her, and two years of waiting had paid off. There wasn’t a thing in the world that could ruin this moment.

‘Would Derpy be okay with this?’

I stopped in my tracks. ‘Where did that come from?’

Still, I could stop myself from considering it. I mean of course Derpy wouldn’t mind. She knows what I do. She even stood up to Applejack in defense of my profession. Why would I think that she would have a problem with me being with Zecora.

I waited for half a moment, partially expecting some inner voice to make a counterpoint, or something.

It never came.

“Is something the matter?” came Zecora’s voice from her lying position.

I inverted a frown I didn’t realize I was wearing. “Nothing at all.” I wriggled out of my jeans and returned to the bed, my erection bobbing slightly beneath me. I positioned myself beside Zecora. She barely took notice of me. She was too busy letting her long-unstimulated nerve-endings reawaken to the sensations of sex. “How are we feeling?” I asked.

Her eyes opened, and she briefly racked her mind for the appropriate word. “Euphoric.”

She started as I nuzzled her cheek gently. “Care to go on?”

“Yes.” She glanced around nervously. “May I… reciprocate?”

I wordlessly swung myself around, that she might get acquainted with my cock. (Incidentally, it put me face-to-pussy, for continued tasting.)

Lightning shot up my spine as I felt a gentle hoof brush lightly along my shaft. “Not so large as I remember.”

My heart broke, just a little, but I chuckled in spite of it. “I’m certainly not the largest of stallions,” I admitted. “But don’t worry; I can get the job done.”

I felt a warm muzzle caress my member softly. “I am sure.”

I continued my work between her hocks as she warmed herself up to my lower half. She started slow, with gentle pecks and probing licks. Soon she was wrapping her puffy lips around me, eliciting low moans from myself.

Bliss. A sideways sixty-nine with a zebra on a cloud with silk sheets, the smell of sweat and sex filling the room. My idea of a perfect afternoon. Zecora wasn’t too great at fellatio, but still… a blowjob’s a blowjob.

I continued to exercise my vast arsenal of oral techniques, and the two of us remained in position for quite some time. I’m fairly certain I managed to bring her to peak half a dozen times before the tenacious zebra’s novice tongue brought me over the edge.

My muscles clenched as I emptied myself into her mouth. Normally I like to give a mare a bit of a warning, but… the mood wasn’t right.

It’s hard to put into words. Sometimes I just know when not to speak up.

Once I unloaded myself, so to speak, the two of us flopped away from each other, exhausted from orgasm.

“Mmm,” Zecora hummed with a slight sense of urgency. I propped myself to find her pointing a hoof at her mouth. ‘Ah, she doesn’t swallow. Well… a chest for everything.’ I nodded and hastily scooted off the bed. I opened one of my many toy boxes and fetched a box of tissues.

Once I hoofed it to her she speedily pulled out several sheets and emptied her mouth into a crumpled ball. “Thank you.” It took the cum-ball and tossed into the trash pail in the corner.

Swish.

She then sprawled out on the bed, smiling like a fool. The smile was just priceless, too. True, genuine elation was just emanating off of her, and it was sort of contagious. It often is.

“So,” I asked, “have you ever done that for a stallion before?” I was just curious.

Her smile vanished.

‘Shit.’

She huffed. “Once.”

‘Do I press the issue, or glance over it?’ I debated internally. ‘If she sulks again, I’ll say something,’ I decided almost instantly.

As such, I changed the subject.

Or, rather… I didn’t change it.

“Not bad for your second time.”

“You enjoyed it, then?” she asked, hopefully.

I didn’t have to lie. “Of course.”

Her smile was back. “I am glad.” She seem relieved, for some reason. There was a story somewhere in there, I was sure of it.

“Well, I’m glad you’re glad,” I said to her with a charming smile. She was really quite stunning, just lying there. Her rustled mohawk. That sweaty coat. That fasciniating runic Cutie mark. Those hips. Celestia those hips. I couldn’t help but comment. “You know, you are a remarkably beautiful mare.”

She giggled. “I am already seduced, Guilty. Why do you flatter me so?”

“Simple. I say it because it’s true.” I traced my eyes over her reposed frame. “Your body excites me. Entices me. It makes me want to do all sorts of naughty things to it.” I grabbed a forehoof and kissed it gently, staring right into her eyes. A classic move. “Zecora, may I fuck you?”

She didn’t miss a beat. Normally mares are a bit surprised when I use an overly blunt line like that, but Zecora was unfazed. “I was beginning to think you would never ask.”

We both grinned as Zecora spread her legs. A well-executed spread eagle.

‘Face to face? It’s been a while. Fun.’ Face to face sex isn’t the easiest thing in the world, but it can certainly be worth it. Especially for making out during sex. Even if you don’t do that, you can nuzzle.

I placed my forelegs on either side of her head as I brought my hips into position. She was glowing. She was so happy to want and be wanted. Happy to give and receive pleasure. Happy to have allowed herself this warmth. She had needed this.

I proceeded gently. Softly rubbing myself up and down her entrance. Kissing at her neck. She shuddered with anticipation. I didn’t keep her waiting long.

I entered her slowly. She was so warm, so wet, so inviting. Her eyes lost focus and her mouth hung open. She said nothing as I began to gently gyrate my lower half. She was certainly feeling it, though; she was biting her lip again.

It felt… it felt so good.

All the gasping and moaning and sweating and fucking. It was just what I needed too.

I love my job.

Soft fucking became steady fucking, and Zecora became very vocal.

“Oh!” she cried. “It f-feels…. Don’t stop. Don’t stop. Don’t stop. Don’t staaaAAAAAAHP!” Her legs wrapped around me. In fact, everything about her clenched violently as orgasm claimed her… including her jaw… which somehow found its way to my shoulder.

I hate my job.

I managed not to scream, but I did stop moving entirely. It was right as I was finishing up as well, so I came right as she bit me.

You take the good with the bad.

After what felt like hours Zecora’s body relaxed.

“Ow,” I said perfectly calmly, in a voice that was in no way, a pathetic little squeak.

Zecora gave me a tired, perplexed look, before realizing what she had done. “Oh my goodness!”

“Don’t worry it’s not that ba— oof!” In a panic she threw me off and out of her and scrambled for the living room, my jism dripping out of her.

“Wait wait wait wait, I have a salve!” she yelled as she disappeared beyond the door. A moment later she returned with her satchel. She hefted the heavy thing up onto the bed and began rummaging around inside. She was on automatic.

“Zecora, relax, I’m perfectly fine.” She continued unabated, producing a small wooden container. “Really, I barely even—”

She shushed me as she rubbed some sort of cream onto her hooves.

“I’m serious, you don’t have t— oooooooooohh,” I crooned as a hoof hit my throbbing shoulder, and all my pain vanished.

“Better?” she asked.

“Oooh, yeah.” I could barely believe how good it felt. Each stroke of her hoof washed away a layer of pain, until it was nothing but a memory. “What is this stuff?”

“My own blend. I make it from a moss that grows in the Everfree,” she explained. “I, uh… I feel I have killed the mood, no?”

“Hmm? Maybe a little.” I couldn’t help but chuckle. The moment she saw me hurt she was all business. It was rather sweet, all things considered.

“I am sorry.” She sounded very remorseful. “It is a rather unfortunate habit.”

“Biting when you come? Well, at least you didn’t do it when I was in your mouth.” She blanched. ‘Oh… that’s what happened.’ Again, I didn’t say anything. She was already mortified. “We can continue, if you like. I honestly feel great after that salve.”

Her head dipped tiredly, and she responded in an enervated tone. “I have been more than satisfied, Guilty. I would fear for my ability to walk home, should we continue.”

“Well, it was certainly enjoyable, wasn’t it?”

“Yes… exceedingly so.” She huffed furiously as her panic died. “I think I would like to lie down.”

‘Sounds awesome.’

So the two of us ended up spooning on the bed. I’m always happy to have my junk next to zebra ass, so I was pleased. We chatted again. Zecora actually ended up telling me about the time she accidentally bit a stallion’s cock. It sounded awful. Apparently he screamed, and a group of zebras came running. Half a dozen of members of her village saw her chomping on his member.

Thankfully she hadn’t bitten as hard as she could have, so he was fine.

Still, pretty traumatic. She confessed that blowing me had helped her conquer her fear that she’d do it every time. Actual sex, apparently, proved too much for her. All told, she was very candid about… well everything. She might get embarrassed about things, but she never shies away from them. It was nice, having on truly honest conversation.

I actually… ended up telling her about me thinking I have feelings for Derpy.

I didn’t use her name of course, I just called her ‘a client,’ but… it was nice talking about it. I only mentioned it briefly, and Zecora just gave me a ‘good luck,’ but even so, it felt good. It was nice knowing that it was… well…

Allowed.

The session was clearly winding down, and Zecora eventually decided it was time to take her leave. After all, she had to brave the Everfree to get home, and better to do so during the day.

“I think it’s time I left, Mr. Pleasure. Truly my gratitude knows no measure,” she said as she pried herself from the engrossing comfort of the bed.

“Back to couplets, are we?” I teased.

“Truth be told, a vacation was nice. But now I must leave this prose-paradise.” She smiled at the cleverness of her own rhyme.

“Well that’s just fine, Zecora. But remember, this little oasis of Pleasure will be waiting for you.” I smiled at my own clever wordplay.

“I owe you more than you know. And shall repay you so. Please take the coin you’ve earned. But to give you more, I yearn. A greater gift I must give to you. Something to convey my thanks to you.”

“You rhymed ‘you’ with ‘you,’” I pointed out, to which Zecora clicked her tongue. “And thank you, but you don’t have to give me anything beyond the cost of the session.” Ever professional.

“See the gift, and then judge. On this I will not budge,” she replied.

“If you insist.”

She nodded.

“Very well,” I relented. Well… relented makes it sound like I actually put up a fight… I really didn’t.

It’s probably just gonna be some potion or salve or something, I haven’t gotten it yet.

“Goodbye, kind escort, and good afternoon. I hope to be see you again sometime soon.”

“I sure hope so.”

She left. I waved goodbye. And she was gone.

Okay I have a tongue cramp. I’m gonna eat something cold and come back to this. I think I have some ice cream.

Author's Note

WOO! FIFTEEN CHAPTERS!

Thank y'all for reading. I heart my fans. Don't forget to like and comment and favorite and all that jazz.

Thanks as always to aquapunkchick, BlackSkulls, Jake the Army Guy, and coandco. They make my story shine the way it does.

Oh, and don't forget! Be sure to check out my blog for some sick fan art!

Confessions

Chapter 16

Confessions

Okay, I should be able to finish up tonight, which is good because I have to get up early tomorrow. Geez, tomorrow’s already Sunday. Sunday means Derpy. That’s gonna be interesting.

Fuck me.

Anyways… Zecora… right.

Or no… I finished that.

So… Crook, then.

Okay.

So, yeah. Zecora took her leave and I cleaned the house, waiting for Crook’s return. Took shower. Washed glasses. Cleaned sheets. Mopped floor. It didn’t take long.

When Crook returned, the sun was beginning to set.

*BANG BANG BANG* “Guilty, is the coast clear?! Open up!” he shouted from beyond the front door.

Rather than chastise him about making a racket when I potentially had a client, I decided to just let him in. Once again, he was not alone.

Radiant. I could use a thousand words to describe this mare, but this one does her the most justice. Her mane and tail a vibrant rainbow, her coat a glorious sky blue, there was no doubt in my mind that this was the Rainbow Dash I’d heard so much about. She was as athletic-looking as Crook, if not more so. Everything about her was just so…powerful. Her frame, her coloring, her expression, her eyes, it was all so… strong. “Guilty, you have to meet this chick. She is, without a doubt, the fastest pony I’ve ever seen.”

I realized that I’d kind of been staring. “Uh…” I shook the rainbows from my head. “…Wow, that… means a lot coming from you.”

The mare spoke up. “Yeah, well, I’m just that awesome. I’m Rainbow Dash. I’m sure you’ve heard of me.”

So humble.

In her defense, she was right. I had heard of her.

“Well, come in. I was about to make dinner for Crook and I. Will you be joining us?” I asked as I led them inside.

She shrugged, her eyes half-lidding themselves. “I dunno. I wasn’t planning on sticking around that long.” She seemed almost… unimpressed, I suppose.

“Don’t worry ‘bout dinner Guilty. You gotta settle a bet,” interjected Crook.

I was intrigued, truth be told. “Oh?”

“Well, she claims to be the fastest pony in Equestria—”

“Which I totally proved!” she reminded.

Crook nodded. “Yeah yeah, you beat me in a race.”

I was taken aback. I didn’t know Crook could lose a race. “She did?”

Crook shrugged. “By a mile… but nevermind that. She thinks she can get somepony to bust a nut faster than anypony, and I think we both know that title goes to you.”

I threw him a look. “Crook, I think Pocket Rocket holds that honor.”

“Details,” he responded simply.

“Pocket Rocket?” inquired the confident young mare.

“Just a whorefriend.” Crook responded. I’m not sure where he picked that up, but I like it.

Whorefriend. It’s cute.

“So what am I doing? Just an orgasm race?”

Crook shrugged. “I guess. Unless you wannna take turns and time it.”

“Alright, dude, let’s do this. Where’s the bed?” she asked. She was certainly ready and raring to go. She was working fast, too. She’d been in the house all of two minutes and she was already searching for my bedroom and had wrangled me into a carnal competition.

“This way,” I responded. I was becoming swept up in her pace. It was something about her. She just… she moved so quickly with her snap decisions and energetic air, but… it wasn’t a sort of speed that made me feel left behind.

It made me want to keep up. I wanted to follow her. She was just so… radiant, again, is the only word that comes to mind.

Once in the room, she made her way straight for the bed. No distractions, no glances around the room. She simply flew up onto the mattress and lay down with her legs spread. “Come on; show me what you got.” She had a glorious figure. Front hooves wrapped around her hind legs, holding them spread wide. She had a darling little pink slit, too. She wasn’t anywhere near wet at the moment, but her lips peeked out a bit. Quite cute.

Something occurred to me, however. “Yeah, hang on. I’ve already gotten off once today. It’ll take you longer to pump out number two.”

“Oh come on, let’s just do this. What’s the hold up?”

“I just don’t want you crying that I had a handicap when you lose.” Her arrogance was rubbing off on me a little. “Why don’t you do Crook, and I’ll do you?”

“Sure. Whatever. I’ve got a race to win.” Ever prideful.

“Always thinking a’ me, aren’tcha?” He gave me a little punch.

“What are friends for?”

“Bond later. Sex now,” insisted Rainbow Dash. Prideful and impatient.

“I like this one,” stated Crook.

“You like them all,” I countered.

So, I unzipped my pants and removed them. Crook and I climbed onto the bed with her. It felt almost primal. Two stallions, closing in on a helpless mare. Not that Rainbow Dash was helpless. She’s probably one of the least helpless mares I’ve ever met.

“Oh. My. Celestia. That’s bigger than Big Mac’s,” she said, eyes locked onto Crook’s already-hard appendage.

I cracked my neck as I situated myself near Rainbow’s rear end. “So you’ve sampled Ponyville’s favorite farmer, I take it.”

“Don’t tell Applejack.” She snickered to herself. “She’d kill me.”

‘Not something you have to worry about.’ “So… shall we?” I asked, partially out of a desire to change the subject.

She nodded, flashing a confident smirk. “Prepare to get blown away… literally.” Even Crook rolled his eyes.

Getting everypony into position turned out to be kind of an ordeal. Crook’s so fucking big that Rainbow Dash decided she needed to be upright to blow him properly. As such, she decided get on top of me and take him from the front. A logical choice, but it put me right where I do my best work. Eventually we got everyone into position, awkward though it was. “Give us a countdown, big guy,” said Rainbow to Crook. He had such a shit-eating grin on his face. He was still hung up on the novelty of the situation. To be fair, I was too, I just wanted to win. I’m not sure why I got so competitive, actually. I think I’m going to chalk it up to Rainbow Dash’s infectious nature.

Crook shook his head. “Alright… three… two… one… go,” he counted off half-heartily. I dove in, and judging by the sound of Crook’s breathing, Rainbow Dash did too.

She was tight, shockingly so. Fit girls can be like that. Regardless, I began to work my magic without difficulty. Once I was actually in the act I began to get a feel for just how fit she was. I let my hooves wander a bit, and everything was pure muscle. Not bulging muscle, just… she was so lithe. I understood why Crook said she was fast. With a body like that, she would have to be. It’s weird, though, she’s a weather pony. It’s a tough job, but not that tough. She must train like mad for that body.

I didn’t hold back. I was still a little fired up from my session with Zecora, and I didn’t have to warm myself up. My tongue slid into her narrow entrance with ease. The sour taste. The musty smell. Her cock-muffled moans. Her weight on my face, her legs on either side of my head, her hot flavor dripping into my mouth. It was just what I needed. Mindless head. Every one of my senses was eager to partake of Rainbow Dash’s incredible body.

I drowned in it. I let the entire sensation wash over me. It was just like old times. Crook prowls the town while I keep the homeplace clean and tidy. He brings home a nice girl. We fuck her stupid. It was exactly what we used to do all the time. I miss it sometimes.

It would appear I’m feeling nostalgic.

As things often do in sexual situations, things escalated. Rainbow’s moans got louder and her hips began to gyrate wildly, which kind of made things difficult on my end. Her head began to speed up too. Crook didn’t seem to have any problem keeping his shit together. He wasn’t going to finish any time soon.

I would’ve noticed, he pants when he’s getting close.

I think that counts as knowing too much about somepony.

Well, the whole affair didn’t last long, which is to be expected of a race. I managed to bring her to the edge rather quickly, but she fought for that last inch for a while. Every inch of her body clenched as she valiantly fought off her climax. I didn’t let up. I flicked at her sensitive nub with my tongue. I tenderly nibbled at her lips. I did everything in my power to give her pleasure.

It paid off (naturally). Regardless of how experienced Rainbow Dash may or may not be, I’m a professional. She came. Hard. Her back arched and with an audible pop, her mouth removed itself from Crook’s member. I wish I could’ve seen her face. Her frame shuddered for what seemed like at least a minute. I never ceased in my efforts; I just kept at it while she came.

“Oh… my… gosh,” she finally spoke as her body begin to relax. “That was… wow.” She awkwardly rolled off of me and collapsed onto the bed. “Okay… I think I’m … I’m just gonna nap for a while.” She curled herself into a comfortable position as her eyelids began to droop.

Feeling a tad boastful, I decided to tease her a bit. “So… that means I win, right.”

Her eyes shot open. Suddenly all her fatigue and relaxation had vanished. “This round,” she said as righted herself. “No way I’ll lose next time.” She thrust an adamant hoof toward me. Well, at least she wasn’t too sore of a loser.

Slightly unconvinced, I turned to Crook. “How’d she do?”

Crook rocked his head back and forth. “Not bad. She can take it pretty deep.” He took a moment to admire his glistening cock. Still hard, of course. “Either way, I still gotta take care a’ this. You good to keep goin’?” he asked the sweaty mare.

“You know it!”

‘Weren’t you just about to take a nap?’

“Lay down,” she instructed Crook, a wicked glint in her eyes.

Crook chuckled. “Yes, ma’am,” he replied, happily obliging. I would liken his genitals some sort of glimmering beacon of sex as it towered upright, but it’s emasculating enough without additional esteem.

Rainbow let out a low whistle. “I’m not sure I can take it all in,” she admitted. Without a moment’s pause she began to climb atop the stallion. It appeared I was sort of an afterthought at this point, so I just resigned myself to enjoy the show.

Narrow as her pussy was, Rainbow Dash actually managed to take Crook’s member decently. She slowly lowered her hips, bringing her still-soaking marehood to his head. In one motion she dropped herself down onto him and swallowed most of his rod.

“Tight!” was Crook’s immediate reaction. Rainbow swiftly began bouncing gently. She bit her lip as she tried to work her way lower and lower down Crook’s shaft. Crook let out a low whistle as she made her way lower and lower.

“Oh my gosh…” she squeaked. “I don’t think I can… *nnph*... get it all.” Willing, though her spirit was, Rainbow’s capacity stopped an inch or so short of the whole thing. She whined at her own failure to go balls deep. “So close.”

Crook chuckled. He’s used to mares not being able to take all of him. “Don’t worry about it,” he said casually. He smiled at her in his usual sexy way as he slowly began to rock his hips. Rainbow’s expression was… intense. Her eyes were closed tight and her brow was furrowed. It was sort of a…. determined look. It took me a while to place that expression. It was odd, I couldn’t quite put an emotion to it, but then I figured it out.

She was exercising. This was just (well maybe not just) more training to her. She was focused on the dirty deed, because it was another way to work out. It was pretty…

What’s the word?

Resourceful?

Innovative?

Clever. Clever works.

It was pretty clever. I mean, I don’t think she was enjoying it any less. And, it’s a good way to motivate yourself to last longer. The sex becomes the end, rather than the means.

Pretty soon, Rainbow’s “workout” kicked it up a notch. She licked her lips and began to doubletime her previous pace.

“That’s good,” blurted Crook somewhat mindlessly. He let his head roll back as he stopped gyrating and let Rainbow take full control. It was really quite the show. Rainbow was giving it her all, and Crook could barely handle it. All the sweat and slapping and juices and moaning.

I may have pleasured myself.

Okay, I did, and it was really nice. Sometimes it’s nice to not have to worry about everypony else and focus on my own pleasure. It doesn’t happen all that much, so I take it where I can get it. Also, live action porn makes for good masturbation.

My hooves may be adept at pleasuring all manner of mare, but I am a grandmasturbator.

I’m proud of that one.

Slow strokes, fast strokes, long strokes, short strokes, working the head, working the shaft, two hooves, one hoof. Back when I was still a gofer, I used to whack it all the time. Surrounded by all that sex at that age, it’s hard not to. I’ve always been fairly tantric about it, just like with sex. I can go for a long time without finishing.

Finishing was not something that I did, however. Well… at least not on my own. “Wanna let Guilty grab the backdoor?” asked Crook to the barely-listening athlete on top of him. He was so casual about it. I complied without really thinking about it.

“Huh? Sure,” she replied, never dropping her pace. The transition was seamless; Crook hoisted his body upward and, sitting up, held it against Rainbow Dash. I grabbed a rubber and positioned myself opposite Crook against Rainbow’s back. I moved quickly; I didn’t want to leave either of them hanging. I placed my hooves on her taut shoulders as I slid my hips under hers. We formed a nice little vertical sandwich.

Yes, my balls were touching Crook’s.

No, it’s not gay.

Almost without disturbing their beat I managed to work my way into Crook and Rainbow’s activities. Rainbow forced herself down onto my rod, just like with Crook’s. My genitals, however, proved far less of a challenge for her. In a single bounce I was inside her. I didn’t think it could be, but her rear end was even tighter than the front. It felt amazing.

It probably looked amazing too. A perfect ten of a mare sandwiched between two handsome stallions on a bed of clouds in a candle-lit den of pleasure, it was the sort of scene worthy of an audience.

Do I sound vain, just assuming I’m handsome?

Fuck it. I’m handsome.

Rainbow Dash’s face began to lose its focus. Her once determined demeanor began to shatter, and a face of ecstasy began to emerge. Her tongue lolled out, her eyes rolled back. Her tight holes squeezed the rods that penetrated her. The wet, fleshy sounds of our sex filled the air. Rainbow Dash began to moan wildly, taking deep breaths in time with the rhythm.

I would’ve like to do more in the whole affair, truth be told, but I wasn’t really in a position to do anything other than sit there and… well… be a penis. Not that I didn’t enjoy myself; I absolutely did. I just… I’m a do-er. I like to do. there wasn’t much doing to be done.

Rainbow Dash began to increase her pace. Her humping got… really freaking fast. Her walls clenched and her juices flowed. She began to chant manically as everything came to its inevitable conclusion. “Ohmygosh! Ohmygosh! Ohmygosh! Ohmygooooooooooooooo—” She grabbed blindly onto the stallion in front of her as orgasm rocked through her nethers. I emptied myself inside her as she came, before collapsing backward onto the bed. Crook came too, much to Rainbow Dash’s delight.

Crook comes a lot when he comes. Semen for days.

For several seconds we all bathed in our pleasure, tremors occasionally coursing through our one collective frame. Eventually Rainbow saw fit to climb off of us, spilling many fluids over the sheets. It was a nice view, her blushing, spunk-filled hole oozing and twitching in pleasure. She lazily rolled onto her back. “Omigosh!” panted Rainbow as she writhed. “That was… awesome!” She threw her hooves up before letting them fall back down to the bed. “This cloud is awesome.” She donned a satisfied smile before her eyes shot open. “Wait… cloud?” She sat up and started staring at the two of us sitting on my mattress, baffled. “How are you—?”

“It’s enchanted.” Crook responded through heavy breaths. “Pretty snazzy, right?”

“Yeah…” she said, giving the cloud a testing prod. “… way cool. It feels just like normal. What’s this kinda thing cost?”

“More than you would be willing to pay,” I said flatly.

“That bad?” she inquired.

And then I said something stupid. “I’ve been paying it off for two years. And I only owe for half of it.”

Crook’s ear twitched almost imperceptibly. He hadn’t missed that. I’d told Crook the mattress was a gift, and while technically that’s true…

… it’s a lot more complicated than that.

Rainbow’s hoof shied away from the cloud’s silken surface. “Wow… talk about an investment.”

Crook shrugged. “Nice things have their price apparently.” He shot me a look. Smug fuck. “So, you, uh… you ready for round two, hot stuff?” The look was gone and that dashing smile was back on his face.

“Nah… I gotta clear the sky about town hall by sunset, and I wanna take a nap first.”

I couldn’t help but scoff. A quick look out the window told me that the sun was literally setting. “Think you’re gonna be late on that one.”

It was Rainbow’s turn to scoff. “It won’t take me thirty seconds to clear those clouds.” There was that radiance again. Something about her told me she wasn’t boasting. I just… I couldn’t not believe her. She’s very intriguing, Rainbow Dash. She’s just so… big. She’s like Crook, larger than life. I can see why Derpy talks about her so much; there’s a lot to talk about.

“So, yeah, I’m gonna take off.” She gently fluttered over to the window. “It’s been fun. I’ll stop by again sometime.”

My eyebrow raised as she opened the window. “Yeah, okay. Next time is going to cost you, though. I don’t normally do this for free.”

She cracked her wings and shoulders with several loud pops. “Yeah, that’s what I hear.” In an instant she gave one solid flap of her wings and jettisoned herself through the portal. She appeared to have vanished. All that remained was a rainbow colored streak and a distant voice calling “Later gators.”

Crook smiled shit-eatingly (that’s a word) at the shock on my face. Rainbow Dash wasn’t just fast, she was electric. Like a… rainbow lightning bolt.

Oh shit, that’s her cutie mark isn’t it?

A little on the nose, I guess.

“Now imagine trying to outrun that,” Crook said, shaking me out of my awe. “I gave up after 10 feet.” He sighed as he collapsed backwards.

“I can see why.” I stood up and moved to close the window. The freezing air was creeping in, and that needed to stop.

“Yeah, it was crazy. She can do all kinds of tricks too.” He propped himself up and smiled at me. “Guilty, what the fuck is up with the bed?”

*Gulp*

I froze. I knew he’d noticed but I didn’t think he was going to bring it up, at least not this soon. It was too quick. Hell, I was still panting from our three-way, and he was dropping a bomb on me. Instincts kicked in, and I began to lie my ass off. I threw on a puzzled face. “I’m not sure what you mean. Is it uncomfortable or something?”

He pushed himself upright and stepped off the bed. “You told me Sunny gave it to you. You told our little Wonderbolt-to-be you were paying it off.”

I saw an out and I grabbed it. “Oh, so Rainbow Dash is training to be a Wonderbolt?”

He didn’t fall for it. “Fuck off, Guilty. Don’t change the subject.” He took a step toward me.

This was quickly becoming a full blown interrogation. I could feel myself begin to sweat. I could feel my heart beating in my chest. I was panicking, though I’m not entirely sure why. “Crook, it’s complicated. I don’t wanna bore you with—”

“Well un-fuckin’-complicate it, Guilty.” He was right next to me now. Towering over my like he always has. Those big brown eyes watching me, watching me like I watch everypony else. “I wanna clear fuckin’ cut answer. I’m sick of all these secrets you’re keepin’ from me. Since when do we keep secrets, huh?” He wrapped a hoof around me. Not an angry hoof, just… forceful. “We’re fuckin’ brothers, Guilty.”

I pressed my head into his chest. Intimidating though he may be, I can’t really be afraid of Crook. “Straight, I really don’t wanna—” My protest died in my throat. I could feel tears in my eyes, and I knew what was coming. I was about to tell Crook everything. I was going to spill my guts all over his big warm sturdy chest.

You know, as much as I write about Crook, it doesn’t bring up images of stallions in my mind. I guess I really just can’t think of him in that way.

I’m rather thankful for that.

I pulled myself away. Crook’s firm grip melted away the moment I began to resist it, and I took a big step back. He must’ve been able to tell how I was feeling because he looked… so concerned. Upset and maybe even hurt, yes, but mostly just worried about me.

“Sour… talk to me. What’s the deal with this fuckin’ bed? What’s the deal with you an’ mama? Fuckin’… talk to me. You know I won’t think any fuckin’ less a’ you. Shit, I don’t care if you killed somepony.” He put his hoof on my shoulder. “Just tell me why my best friend left.”

A powerful blow. I couldn’t keep it up. I couldn’t not tell Crook. I had to tell him.

So, I did. Standing awkwardly in that chamber of pleasure I call a workplace, I began to tell him.

I told how Ms. Smile…

I told him how mama…

I told him about how she was having me sleep with ponies outside the stable...

And about how she was paying somepony to take pictures of the sex...

And about how she was… blackmailing them.

I didn’t really explain about the mattress, it wasn’t what he wanted to hear, anyways. What I didn’t know, was how he was going to react to everything. I expected him to be disappointed, upset, angry, disbelieving… something.

But, he just smiled… and patted me on the back… and told me “I guess you’re not such a goodie-goodie after all.”

It…

It wasn’t really what I wanted to hear.

I…

I wanted him to be mad at me… I think.

I dunno…

I just don’t know…

“Hey, I’m gettin’ hungry. Make me somethin’, will ya?” said Crook, as though nothing had just happened. I guess as far as he was concerned there was nothing more to say.

Maybe he was right.

So, I made stir-fry. Peppers, onions, some carrots…

Why am I writing about this?

It doesn’t matter.

Crook liked dinner. We talked, and then we went to bed. I never brought it up again.

I didn’t fall asleep. I kept thinking about… everything. I couldn’t turn my brain off; it was like it was on fire. Not in pain, just… too on. Thoughts rocketed around my head and there was nothing I could to do stop them. All the things I’d done and the ponies I’d wronged. I wondered what Derpy would think if she knew. Logic kept telling me she would hate me, but… she’s surprised me before. I’ve been thinking about that a lot lately.

Shit… this is just a whole bunch of emotions all at once. It’s a bit difficult to write down, honestly.

Ugh… I need a shower.

So… so morning came… slowly. Eventually Crook woke up, hungry as always. I made breakfast. Crook had a drink or two.

And then he blind-sided me with something. “So, anyways, I should probably be gettin’ outta yer hair. I’m gonna grab an early train.”

I whipped around, nearly dropping the dishes I’d been washing. “You’re leaving?!” I practically shouted it.

“Yeah… I been away too long. Everypony’s probably wondering where I am.” He grinned that shit-eating grin. “I didn’t tell nopony I was leavin’.”

It was too sudden. I was only just getting used to having him here. “I… but… You just got here!” I protested, my voice utterly devoid of confidence.

“C’mon, it’s been a few days, Guilty. Besides, I’ve already made enough trouble for you.” He was proud of that statement, I could tell.

My mouth was dry. I didn’t want him to go. “Come on, Crook, I’ve got a client later. I may be able to talk her into a spit-roast.” I pleaded without shame. I was being such a baby.

Crook smirked and shook his head before mussing with my hair. “Well, Celestia knows I’d love to stick around, but I gotta get fuckin’ goin’.”

I sighed. It was tough to admit, but Crook did have to get going. He had a job and a home to get back to. “I know…”

“So don’t be a pussy about it, aright?” He pulled me close and planted a big kiss on top of my head. “I love you, Sour Dough.”

I pushed him off of me and gave him a firm punch in the arm. “Yer such a dork,” I teased.

“Yeah, well, fuck you!” he retorted automatically. He punched me right back. “And next time we get together, yer comin’ back home to visit. Bring that dopey broad yer crazy for.”

“Maybe I will.”

He raised an eyebrow. “You really do like this girl, don’t you?”

I laughed it off. “Maybe.”

“That’s a yes,” he proclaimed confidently. However, his smirk faded, and he went from cocky to sincere in a heartbeat. “Treat ‘er fuckin’ right, yeah?”

I snickered at that. “Who are you, Close Shave?”

There was a hint of… something on his face. Fear, maybe? Anxiety? Something sour. “Yeah, well…” he said as though the life had been sucked out of him.

“What’s wrong?” Something I’d said had depressed him. Crook doesn’t depress easily.

For a moment he considered brushing it off. I think my little episode last night made him reconsider. I’d confessed my troubles to him, it was only fair if he did the same.

That’s not my thought process, for the record. It’s Crook’s.

“I’m… I’m thirty years old, Guilty.”

“So… mid-life crisis?” I teased.

“Hey, fuck off.” He sighed tiredly. “I’m just… my good looks ain’t gonna hold out forever, Guilty. I’m not sure what I’m gonna do once I’m that guy’s age.”

It hadn’t even occurred to me. I mean… to be fair he’s got quite a few years left of being drop dead sexy, but… that’s gotta be scary.

Of course, it applies to me, too. No one’s young forever. However, not to toot my own horn, but I’ve got more going for me than Crook. Okay well… more is the wrong word. I’ve got different things going for me. My skills, my charm, my mannerisms and practiced lines. Those stand to the test of time a bit better than Crook’s raw magnetism.

I searched the recesses of my mind for something to say. I searched for some proper perfect comforting thing to help my friend. When I came up empty I opted to change the topic of conversation instead. “So, hey, what were you talking about with Close the other day?”

“Uh…” His eyes darted around as he tried to remember. “Oh! He was sayin’ if I wanted to do some royal work he’d put in a good word for me.”

“Royal work?” I asked unbelieving. “You mean like… joining the guard?” That seemed like the last thing he’d do.

“No… just… park ranger… Night watchpony at royal institutions… stuff like that.” he explained.

I tried not to twist my face. Those didn’t sound much better than joining the Guard. “Can you… see yourself doing that kind of thing?”

He shrugged. “I dunno. Gotta have somethin’ to fall back on, though, right?”

“I… guess.” It still just seemed odd. Trying to think of Crook as an authority figure of any kind just doesn’t… work. I can’t imagine it properly. “Can you even do that stuff with your record?”

“Juvenile records are sealed, Guilty.” He winked at me.

“Oh yeah.” I just shook my head. The whole thing was just so silly to me. “So, uh… takin’ off then?”

“Yeah. Take care, Sour Dough.”

“You too, Straight Arrow.”

He gave a nod and left. Just as suddenly as he had come into my life, he exited it.

So, there. That’s all I wanted to say about Crook.

I have to get to bed, I’ve got Derpy tomorrow.

Let’s see how that goes.

Author's Note

Thanks once again to my lovely editors:

BlackSkulls
aquapunkchick
coandco
JaketheArmyGuy

I'm sorry this took so long; I had a hectic October. Hope you all enjoy it.

Clients that aren't Clients

Chapter 17

Clients that aren’t Clients

I had an interesting day today; it was sort of full of surprises. Derpy’s session was today and… well, I’ll just get into it.

This morning was hectic, and I’m still not exactly sure why. I’d had the whole night before to clean and tidy and yadda yadda yadda, and I’d gotten everything done, but that morning nothing seemed… done. The dishes had water spots. The bed sheets weren’t quite straight. The floor had gotten dusty. The downstairs clock was running fast. The fireplace needed cleaning out.

Oh, and note to self, that plastic ivy on the fireplace is starting to show its age; it’s a bit melted and frayed, so I took it down. I need to buy some more, soon.

To sum up, though, it just felt like nothing had been done quite right. I fretted about for a couple hours, just… fussing... perfecting.

When the knock came I had a miniature heart attack. I wasn’t done. Nothing was ready. Everything wasn’t up to par. My whole house was…

...fine. My home was immaculate. Dumbfounded, I searched my surroundings for all the errors I had been convinced existed only a moment ago, only to find my little cottage as clean as it had ever been.

As I stood there, somewhat stunned, the knock came again, followed by Derpy’s voice. “Guiltyyyyy! I’m heeeeeere!” In that moment I realized what had been happening. I was panicking. I was panicking because It was the first time I’d seen Derpy since…well… since I figured out how I feel. “Helloooo?! Guilty?!”

‘Derpy’s still waiting for you, buddy.’

I almost slapped myself as I immediately stepped to my front door. I opened it, admittedly, a bit too fast. Derpy recoiled in surprise. “Sorry, I was in the bathroom,” I lied, reflexively. Why did I do that? Why did I feel the need to make an excuse?

Ugh… I’m second guessing everything right now.

Derpy didn’t mention anything about my obvious haste. I’m not sure if she was being polite, or just didn’t think anything of it.

Right there. Second guessing everything.

“That’s okay!” sung Derpy with a warm smile. “Come on, it’s time for sex!” She marched happily inside, picnic basket of heavenly baked goods in tow. She almost forgot to put down the muffins as she eagerly trotted to the bedroom. She stopped short, though, when she realized I was still standing at the front door. She smiled at me with a cocked head. “Come on, Guilty.”

I snapped out of my… daze, I suppose, and made a quick recovery. “Sorry, I just got distracted by that brilliant rear-end of yours.”

Not my best work, but she giggled, nonetheless. “You’re so silly, Guilty. It’s not that great.”

I scoffed. “I think you’re underestimating just how lovely it is.” She blushed at my compliment. I don’t normally bother with flattery when it comes to Derpy. She may not have been expecting it. I usually use it with newcomers or mares who need a little buttering up, and Derpy is anything but.

Still, I think she appreciated it. “Thanks, I guess. Now, come on! Let’s put this butt to good use!” She wiggled her ass at me. I couldn’t help but smile.

I was kind of expecting to… get nervous. Part of me thought I wouldn’t be able to go through with our session with all of my… inner turmoil. I didn’t, though. Things were going… smooth… like they always do. Muffins on the table, Derpy in the bedroom… everything was going swimmingly.

She propped herself on the bed as I quickly grabbed a potion and wriggled out of my jeans. Legs spread, tail up, already raring to go. It was enough to get any healthy stallion fired up. She’s really very sexy, and I’m not just saying that.

Well, I’m writing it… but I’m not just writing it, either.

I moved to mount her. “So how are things? Dinky okay and all that?”

She giggled. “Oh, I think Dinky’s got a little bit of a CRUSH!” She almost lost control of her speech as I made a gentle tap on her entrance. She was just as sensitive as always.

“Oh? That’s quite the development.” I made gentle motions up and down her lips. Here hips hungrily tried to press themselves onto me, but I teased away from her. “Your first love is an important part of growing up.”

“Oh, it’s just puppy love. She’s still a little… girl.” She was getting heated, but I continued to deny her pleasure as we conversed. Her body writhed under mine, quivering in anticipation.

“So, who’s the lucky colt? Not that I’d know, I guess. Not a lot of kids come out here, as you’d imagine.”

She giggled again. “You’re not gonna… believe it. I think it’s the boy whose… mmmmm… tooth she broke.” She was having trouble getting through her sentences. That meant it was time to take the proverbial (and literal) plunge. “OOOOoooooh, that’s nice,” she commented as I entered her. What can be said about Derpy’s cunt that I haven’t said already: warm, wet, soft. It’s everything a mare’s entrance ought to be. I suppose it’s a little loose, but she’s given birth, so…

Wow, that’s kinda trippy now that I think about it. Dinky came out of that fucking thing. Pussy is just so… very different in my line of work. At least, it feels that way.

Tangents aside, Derpy and I were just getting into the swing of things. “Didn’t you say that kid was making fun of you?” I began to gyrate my hips ever so slowly as I spoke. I fell back into our usual routine: casual conversation and standard sex. Derpy’s pretty vanilla, all told. Just… sex… a little oral… that’s all. I kind of appreciate it, it makes the session… easy. It gives me a chance to enjoy it a little.

“Yeah, but he… he apologiiiiiiiiiized!” Wings splayed and muscles clenched in climax. I’d barely started, but she was already beginning to have her orgasms. She’s so very sensitive.

“Well, that was nice of him.” Thrust. Plant kiss between wings. Thrust. Run hooves along flank.

“Yeah, he was really sorrryyyyyyyy!” Increase speed. Kisses along the wings.

“Oh, he apologized to you face-to-face?” Thrust. Nibble at ears.

“Y-yeah! Dinky apo… apologized t-tooooooooooooo!”

“On her own?” Increase speed.

“Yeah,” she gasped. “I… I didn’t… *huff*... maaaaaaaaake her!”

“Well that’s good.” Lay body firmly into hers. “So, when’s the wedding?”

She giggled. “Guilty, you’re so sillllllyyyyyyyyyyy!” The bedroom was beginning to reek of sex. I really do love that smell: the sour stench of sweat and pussy. It’s something I grew up with and it really… makes me comfortable, if that makes sense. “Oooh, by the way, e-everypony really liked you at… at… giiiiiiiiirl’s…” She took a few breaths before she could finish her sentence. “ … night.”

Kisses between the wings again. “Yeah?” Prop self up and thrust deeply. “I’m glad I made a good impression.” Increase pace. Make balls slap clit. “If I’m welcome, I’d love to come again.” Nuzzle from behind. “I’d hate to intrude on girl’s night too much, though.”

“It’s… hah… no prooooooblem!” She began to lose strength in her legs. She was bowing under my weight. It was time to guide us onto the bed. Lift her onto the mattress. Guide her onto her knees. Follow suit. Never let member exit her.

“Maybe I should sit poker out, though. I wouldn’t want to be ‘that guy.’”

She laughed out loud. “May… maybe.” Continue thrusting from upright position. Push her legs together. Place knees outside her legs. “Oh, and… and… I th-think you were riiiiiiiiiiiiight!”

I cocked my head. “About what?” Grip ass tightly. Pull vigorously onto member.

“G-G-Goldy. I think you make her... uncomfortable.” She was becoming incredibly warm and wet. The cold feeling of her juices ever so gently splashing on me was becoming immensely pleasurable.

I slowed down, and continued my movements at a steady pace. “Yeah? She say something?”

“N-n-no, when I… when I was taaaaaalking about that night, she said you were nice and she had fun, but… but she—” she failed to finish her sentence as her tongue lolled out of her mouth. She threw her head back in pleasure as she crested another wave.

“She just seemed uncomfortable?” I offered.

“Un-hun,” she grunted in affirmation. I stopped my thrusting, allowing her and myself to relish in her climax. Her walls clenched me as her wings flapped in spasm and every inch of her shivered. “That was a big one,” she commented with a tired laugh.

“Need to take a break?” I asked.

“Just a little one,” she replied. I removed myself from betwixt Derpy’s lovely legs and lay down next to her. The brisk air hit my member as I slid out of her.

I briefly pondered what to say next. I mean, I knew why Derpy talking about me would make Carrot Top uncomfortable, she doesn’t want to get found out. However, I wasn’t supposed to know that. I thought that the least conspicuous thing to do would be to spitball ideas off of Derpy. “Do you think she has a problem with what I do?”

Derpy pulled a hoof out from under herself and brought it to her chin. “Maybe. She did seem kind of upset when I told her I was seeing you. Remember? That day at the market?”

I did remember. “I guess… I dunno, maybe I just rub her the wrong way.”

“Well, don’t worry. I’m sure you two will be friends eventually.” ‘Heaven forbid.’ “Lily seemed to like you a lot though. She said you were awesome.”

Even in repose, an escort’s job is not done. Trace hoof delicately along side. Nuzzle affectionately. “Yeah?”

“Yeah, she said you were ‘such a gentlecolt.’” She responded to my cuddling in kind, allowing herself to sink into me. “I told her if she liked you so much she should make an appointment.”

My stomach churned at the notion. I honestly don’t think I can imagine a more awkward situation. “Does Lily even go for stallions?” I asked.

Realization seemed to dawn on her. “Oh, probably not, huh? I didn’t think about that.” She shrugged. “Oh, well. Her loss.”

I snickered. “Well, I’m sure she would say the same about you and mares. Or, do you go for mares too?” I’d never taken the time to ask her that. I was curious.

She shook her head. “Nah.” She pressed herself into me with renewed vigor. “This is all I need.” She proceded to press her behind onto my still erect stallionhood. “Well… maybe this too.”

“Ready for round two?” Whenever I ask Derpy that question , it’s… different. It’s not a sly suggestion. It’s not a seductive maneuver. It’s not a tactic. It’s just a question. I’m curious if she’s ready for more. It’s just simpler with her.

“Uh-huh!” she replied in that warm, mirthful voice of her. She raised a leg high. “Like this okay?”

“Of course,” I responded. I slid myself into posiiton. The Sensual Spoon, as it was introduced to me, is fun position. It’s sort of a sideways half-mount. It’s not very easy, but worth it, in my experience. It’s more of a position for the mare’s benefit, to be fair, but that’s all that matters in a session.

And in general, in my opinion.

I thrust into her again, her insides as welcoming as ever. “I like this one, it’s fun,” said Derpy as she did her best to hold her leg high. “It’s kinda hard, though.”

“Well, it never takes very long to make you feel good, so it shouldn’t be an issue,” I teased as I began to pump slowly.

“Hey, shut uuuuuuuuuup!” she said in ecstasy, proving my point perfectly.

“I’m not even gonna say ‘I told you so.’” Increase pace.

“You… you just diiiiiiiiiid!” Orgasm upon orgasm took hold of her body. Juices spilled out of her and breath became labored. Sweat soaked her coat, and and she struggled to keep her form.

“I suppose I did.” Assault the spot between the wings with tender kisses.

“You’re... so… silly.” He words were coming in sputters and and grunts and my further attempts at conversation were met only with vague moans of pleasure. After several minutes of raucous fucking I blew my load inside her, and the two of us collapsed in a heap. As I pulled myself out of her, my jism dripped from her lips, staining my sheets. “That was fun,” she said. “Wanna lick me now?”

‘Yes, please.’ “Sure thing.” Before I could grab hold of Derpy’s hips and dive into her sweet folds, she stopped me.

“Hang on. Lie on your back, I want to try a thing Lyra told me about.” I eagerly obliged, fairly sure I knew where this was going. Sure enough, Derpy climbed on top of me and thrust her hips into my face. Just as I began to lick with vigor, I felt Derpy lean forward and wrap her lips around my firm stallionhood.

Bliss.

She’s gotten so good at that since she started coming to me. When she started out her technique was… well… not bad, but… lacking. Over the course of two years she’s gotten pretty good at working the pole, so to speak. I’ve never coached her, or told her ways to improve, she just… learned. I like to think that means I’m having a positive influence of sorts.

I let out a low moan. Derpy had apparently never heard of a sixty-nine before. Needless to say, I could not be more pleased. Her mouth enveloped my member. My tongue plunged into her depths. I reached up and grabbed her haunches. I pulled her firmly onto my face as I vigorously licked at her with fervent intensity.

I indulged deeply of her flavor and her scent and her movements, and she delighted herself with my rod and my tongue. There’s a reason it’s called “eating” somepony; you are partaking of their very body for your own pleasure and gain.

But it’s also called “giving head”, because you give just as much pleasure as you take. Truthfully, I like to think I give more than my fair share. This was evidenced by Derpy’s biggest climax yet.

Her legs fought against the bed, wrenching her from my grasp. Without so much as thinking, my muzzle chased after Derpy’s delicious slit . As I connected with her once again, I could feel myself reaching my own climax. I basked in pleasure as I continued to eat my way through Derpy’s uncountable orgasms.

All at once Derpy’s back arched and her wings flared. She stopped her eager sucking just in time for me to spill myself all over her face as she withdrew. She clambered off of me, and crawled onto the sheets, writhing. Her limbs pressed into the sheets, as she scrambled about in what appeared to be panic.

I was suddenly rather concerned. “Are you okay!?” Okay, perhaps very concerned.

“C-c-coming! So m-much comiiiiiiiiiing!” she cried. Several seconds passed as I debated taking some course of action. Unfortunately, all I could really think to do was ask if she was okay again. Thankfully, Derpy’s…well… fit subsided in due time. Eventually all her flailing and spasming died down, and Derpy melted into a puddle of very exhausted mare. “I… that… tired,” she groaned.

I managed to swallow my worry, and put a semblance of an act back onto my face. “Need a nap?” Smile.

She nodded and proceeded to curl herself into a ball. “Nap,” she parroted with a yawn. Positively adorable. Within moments she was snoring quietly. This wasn’t the first time this has happened. Sometimes Derpy needs to knock out after a mind-shattering orgasm.

So, I decided I’d do what I always do when Derpy sleeps. I’d shower quickly and cook her something to eat. Yes, we had muffins, but I could turn a midday snack into a meal with relative ease. Derpy thinks I’m a good cook, apparently. She told Carrot Top as much.

I cleaned up quickly, and took stock of my kitchen. I had a rather poor selection of fruits and veggies, actually, which was unfortunate. I did, however, have quite a few flowers, so I decided to make a nice little bouquet salad.

I steamed some tulips and what remained of my carnations. I figured something light would help to balance out the heavy banana muffins Derpy had promised. That and the savory carnations would nicely compliment the sweetness of the banana.

I tend to overthink things, don’t I?

I really like cooking for Derpy. She’s always so appreciative of whatever I make. She tells me how delicious it is with a great big smile and she means every word. I wonder if Dinky would like my cooking.

Why am I thinking about Dinky?

Anyways...

I was looking through my cabinets for plates when Derpy stumbled out of the bedroom. Her face was still caked in seed; her hair was a turbulent mess. “Morning,” she mumbled, eyes still closed.

I chuckled. “It’s not really morning, Derpy. It’s almost noon.”

She brought a hoof up to rub her eyelids, which really only served to smear the semen into her coat. “Noon?” Her eyes shot open. “Ohmigosh, I’m late!” she cried. Before I knew what was happening, she was running full tilt for the front door.

Derpy’s lucky my reflexes are as good as they are, otherwise she might have flown through town with a face covered in… well… me. “Sunday! Derpy, it’s Sunday!”

She tried to stop when I shouted, but momentum carried her forward into my door.

Head first.

*THUNK!*

“Derpy!” I almost dropped the plates as I rushed to her aid. “Are you okay?!” She hadn’t fallen, or anything, but her head made a pretty nasty noise against that hard wood. I just wanted to make sure she was okay.

She held a hoof firmly on the top of her skull. “Ow…” she groaned, before voicing a cheery “I’m okay.” She smiled up at me. Truthfully, she was sort of a mess: wincing in pain, hair like a homeless person, a face coated in juices. If anyone were to walk in right then, things might not look so great for me.

“Are you sure?” I was really worried about her. She might have been bleeding, after all.

“Yeah, I run into stuff all the time. It’s no big.” She casually waved a hoof as she sniffed the air. “Oooh, what smells good?” she asked hungrily.

I was mentally debating if I should insist that I examine her head, so my response was a bit delayed. “Just steaming some flowers. I figured they’d be good with the muffins.” Not this time, she seemed fine, at least.

“Smells delicious,” she hummed with a lick of her lips. She paused before licking again, seemingly confused. “Do I have semen on my face?” she asked, totally candid.

I couldn’t help but giggle. “Yes, Derpy. You have semen on your face. You may want to take a quick shower.”

She nodded in agreement. “Okay, but don’t eat without me.”

“I won’t,” I assured her as she trotted up the stairs.

I poured us some tea and finished the flowers while she was showering. I made everything look nice pretty, as an escort should: set the table, arranged the dish everything nicely, cut the stems off...

Yes, I cut the stems off of my flowers. No, I am not a child. I know it’s kind of like cutting the crusts off of sandwiches, but…

… fuck stems.

Everything looked lovely by the time Derpy came down the stairs. Her transformation was astounding; she was glowing compared to before. Her dripping wet mane, her powerful smile, it was enough to put me at attention again.

And, that fucking smile; her glee is almost infectious.

Oh, who am I kidding? It is infectious.

“Wow! That looks really good, Guilty” ‘Not half as good as you do.’ I actually thought that. When did I become so corny?

I shook the kernels from my head (Ha.) “Well, dig in. There’s plenty to go around.”

We both took our seats and feasted. The flowers with nice and tender; they all but fell apart in my mouth. The tea was perfect and piping hot. It was a wonderful little hot meal on such a cold day.

I am going to make a point of not describing Derpy’s muffins.

It does things to me. When all was said and done, the two of us were thoroughly satisfied. “How were the flowers?”

“They were yummy! I love steamed carnations! You’re such a good cook, Guilty.”

It felt… really good to hear that. It sort of perked me up just hearing her say it. She says that every time, but… I dunno… it seemed different. Logic denotes that it’s because I’ve discovered feelings for her. Such feelings would surely make a compliment such as hers especially moving. Yes. Quite.

Ugh… feelings.

I started thinking again. I still haven’t decided whether or not I’m going to attempt to pursue a relationship with Derpy and I was wondering if… if this is what our days would just be like. Waking up to casual sex and a hot meal, smiling at each other from across the dinner table? Would I cook for her every day? Is that what a relationship would be like? Of course, it would be more than that, and not all good. What would our fights be like? Would she just slug me like she had Applejack? That was a terrifying thought. I’d fall like a house of cards. Oh, geez, would I be a battered stallion? No, that was ridiculous. Derpy’s not like that. Would the sex change? I imagine not, it already pleases both of us quite wonderfully.

“So, Guilty, I was wondering if you’d want to go on a date with me.”

Would…

Wait, what?

If I was holding something I would’ve dropped it. I just sort of… stared at her. She had the same innocent smile she always does. That same gleeful expression adorned her face, as though what she’d said was perfectly normal.

‘But then again, isn’t it? I mean it makes sense. I’ve been seeing her for a while now; we’re pretty close. I mean if she’s asked her hairdresser out, asking me out isn’t too far removed from that, right? This is happening. This is actually happening. I guess it’s my turn to—’ I stopped. I stopped my train of thought before my little fantasy got any bigger. I kept my hopes from rising any higher as one very simple fact occurred to me.

‘My luck’s not this good.’

I kept my smile from cracking as I asked her to clarify. “How do you mean?”

She blushed a little, clearly embarrassed for some reason. “Well, it’s been a while since I’ve actually succeeded in asking somepony out. I figured I could use the practice. Would that be okay?” Big happy smile. Ears up and full of joy. Darling mismatched eyes.

A smile that pretty should not have been making me feel so... empty. ‘Answer the question, Guilty. You can’t just leave her hanging.’

I tried to answer. I really did, but the words literally died in my throat.

‘Just… just answer okay? It’s not gonna be fun, but you gotta fuckin’ do it.’

I found my tongue a bit later than I would’ve liked, but not so late as to arouse suspicion. I almost gave my default answer of “that falls outside the purview of our relationship,” but… but where would that get me? I gave her a half-baked excuse.

“Well, I’m not opposed to the idea, Derpy, but I’d hate to cause that much trouble for you.”

‘Nice try, but that’s not gonna satisfy her and you know it.’

She cocked her head. “Trouble?”

“Well…” I was still constructing my excuse. “… I mean if it was in a public place, it might look bad.”

She scoffed. “I don’t care who sees me with you, Guilty. You’re my friend.”

I was sweating. I’m not sure why I was so desperate to get out of this, I just was. “Well, I mean with Applejack and all that—”

“Fuck Applejack!” ‘She’s been saying that a lot lately.’ “I don’t care what she thinks.”

“Well, I guess….” ‘I’ve got nothin’. You’re gonna have to go. Sorry, buddy.’ “…how’s tomorrow night?”

“Works for me! Pick me up at seven?”

“Sure thing.” ‘Don’t let that smile fall, Guilty. That’s lesson one.’ “How should I dress?”

She shrugged as she searched through her little picnic basket for her bits. “I dunno. Something handsome.” Out came the bits, and onto the table they went. “I should get going, though. See you tomorrow, Guilty!”

‘Only a few more seconds, keep smiling.’ “See you tomorrow, Derpy.” Out my door she went. Twenty paces. Turned back. Waved. Kept walking.

I closed my door. I needed to clean. I needed to keep my mind occupied, anything to keep myself from thinking. I wasn’t totally successful. Even with all the dishwashing and bed-making and dusting I managed to do I couldn’t help but come to two very annoying realizations.

First, going on this date knowing that it won’t actually mean anything is going to suck.

Second, the fact that it’s going to suck so much probably meant I’d fallen for Derpy pretty hard.

‘Ugh… why do I do this?

‘Why do I just fall for ponies like this? Granted, it’s only really happened twice, but that doesn’t make it any less…

‘Annoying? Troublesome? Stressful?

‘I don’t know. Maybe I just… over-worry things. Maybe I don’t actually fall for ponies, maybe I worry that I’m falling and that makes me think about the pony in question and that makes me think I’m falling because I can’t get them off my mind.

‘Does that count as a vicious cycle?

‘I think too much, don’t I?’

A knock at my door ended my internal monologue.

As a side note: why does that keep happening? Is this normal in a small town? Do ponies just come and knock on your door? Is that a neighborly thing? Well… I don’t really have any neighbors I don’t think. Townmates, then? Is it townmately?

Regardless, I answered the door with a smile. Appearances, appearances.

Corded red muscles bulged under a thick red coat. If not for the color I would’ve thought Crook had come back to town already. I swallowed as Big Macintosh’s frame cast a literal shadow over me. “Um…” ‘Don’t think about him. Don’t think about his powerful weight on your back. Don’t think about his fat, thick member penetrating you. Don’t think about his hot breath on the nape of your neck. Don’t think about the taste of his cock. Don’t think about the smell of his sweat. Don’t think about it.’ Images assaulted my mind. In panic I said the safest words I could think to. “… I don’t… I don’t take stallions.”

The giant of pony blushed furiously, which, honestly, served to calm me down a little. “A-Ah Ain’t…” he stammered, his voice a bit higher than what I’d normally heard at his little apple stand. ‘Good. Nervous is good. Keep him in your pace.’ “Mah… Mah sister…” He stopped and shook his head. I began to notice him shivering. Escorting instinct told me invite him in out of the cold, but I decided against it. “Ah’m lookin’ fer yer friend,” he said finally.

“He’s gone,” I responded tersely. I had a good idea roughly what this was about, already: retribution in some form or another. “Back in Manehattan, he caught the train a few days ago.”

He sighed almost imperceptibly. “That so?” I could already see him beating himself up. He clicked his tongue. “Dangit.” His eyes spoke much more than his mouth. I could see that he did not want to be here. Was he here at Applejack’s behest? No, if she was going to send him to… do whatever he’s here to do, she would’ve done it right away. It had been almost a week at this point. So, he was here on his own. Against his better judgement, maybe. What did he want, then?

I pondered. I wanted to dismiss him, honestly. I was being so rude to him, looking back. I think I just wanted him and the graphic mental images the followed him to leave. I just wanted this little encounter to be over.

But then I realized how big of an opportunity this was. Presumably, Applejack’s brother was someone close to her. If I could… well… if I could get him on my side, that would be a powerful play.

Conniving won out over uncomfortable, and I changed my tactic as well as my attitude. “Well, come in. It’s fifty below out here.” I suppressed a swallow. Something about being all alone, so far away from anypony that could help. When I’m with a mare I worry less, I suppose. It’s just… if he wanted to kill me… he fucking could. No clients. No Crook. Nopony for a literal mile.

Back in the stable, we had ponies for that. Security. There was a bell in every room. We only rang them when we were in trouble. I never had to use one, but the knowledge of their existence was comforting.

I kept it together, though. I put on a friendly smile, adopted a positive demeanor. “Take a seat. You want something warm?”

“Coffee,” he responded after a moment’s hesitation. This was good. He clearly had qualms about accepting my hospitality. Having him out of his comfort zone put me at an advantage.

Well, I guess I was out of my comfort zone as well, but whatever.

“I hope instant’s okay!” I called from my kitchen.

“S’fine,” he called back. I put the kettle on and fetched the (frankly wretched) instant coffee out of my freezer, as well as some black tea for myself. I peeked in on Big Mac briefly before I walked back. He was taking in the surroundings, looking at my quaint little living room.

“Not what you were expecting?” I made a very pointed effort not to use any voice that could in any way be construed as sexy or seductive. “Kettle’s on, it’ll be a bit.” Big Mac was very out of his element. He was stoic, to be sure, but the telltale signs of discomfort couldn’t hide from me. Poor eye contact. A subtle swallow. The silent stallion spoke volumes.

His gaze shot away defensively. “Ah weren’t expectin’ nothin’.” Nervous shifting. He was as bad a liar as his sister.

“I’m sure.” Cocky smile. I decided to go on the offensive. Any conversation can benefit from my training, really. So long as I kept Big Mac, I could all but dictate the outcome of this encounter. I took my seat. “So, Mister Apple… or do you prefer Big Macintosh?”

He shrugged. “Anything’s fahn.” His accent was a bit thicker than his sister’s.

“Big Mac, then. I don’t think it takes a genius to know what this is about.”

Just a nod.

I rested my chin on my hooves, dissecting his every twitch and movement. ‘What’s the play, Guilty? Ambivalent? Apologetic? Flat-out ingratiatory? Play the victim?’ I cracked my neck as a dozen strategic conversational techniques occured to me. ‘ Hmm… let’s just feel it out for now.’ “So what was your plan, Big Mac? What were you going to do once you confronted Crook?”

Eyes downcast. “Ah ain’t exactly sure.” A pang of guilt.

“Hmm…” This was turning out to be a little more difficult than I would’ve liked. Big Mac was proving a hard read. Emotions are easy, but motives? Those are tricky. For the moment, he seemed content to answer my questions, so I took advantage of the opportunity. “Where do you even stand on this issue, Big Mac?”

He snorted, clearly irked. “Tweren’t raht, what yer friend did.”

“Agreed,” I lied. I felt that what Crook did was a textbook example of giving somepony a taste of her own medicine, but Big Mac didn’t need to know that.

I’m a bit of a bastard, aren’t I?

Big Mac’s eyes went wide for a moment; he wasn’t expecting that response. “But not what I meant,” I continued. “I meant on the issue of me. I don’t think it’s a secret that Applejack wants me out of Ponyville entirely. She hassles me in the streets. She refuses to sell me anything on market day. She tells everypony what an evil, wicked stallion I am.” He showed only the faintest trace of surprise. “You, on the other hoof, are decent to me. You’ve never turned me away from your cart, you’ve never said a single word against me. So where do you stand?”

Visible swallow. Twitch of the ear. Evasion of eye contact. “Ah ain’t thought much about it.” A lie.

“Well, you’ve at least decided that my bits are still good,” I joked. I wasn’t going to press him on this. It wasn’t getting me anywhere.

Before I could explore another avenue, he spoke up. “Look, ah didn’t come here to talk about all that. I was just… thinkin’ maybe Ah could talk some sense into yer friend. But he ain’t here, so—”

“I am sorry about that,” I interjected. I had to keep him talking. He could leave at any moment. “Crook can be a bit… overzealous.”

“Overzealous in tryin’ ta sully mah sister’s good name in front everypony?” Anger crept into his voice.

‘Calm, Guilty. Keep calm. He’s not mad at you, he’s mad at Crook.’ “Overzealous in trying to protect my name. While I disagree with his means, his ends are not as sinister as you make them out to be.”

Big Mac just narrowed his eyes a bit. Truthfully, it was incredibly menacing. “How’sat?” he asked.

Easy enough to explain. “Your sister has pull with the townsponies. Crook was trying to make her appear… more reproachable, so that Ponyville wouldn’t take her outcries against myself as gospel.” I actually think that I sugar-coated that quite nicely.

That said, his reaction was even better than I was expecting. “Ah suppose ah can see where he’s comin’ from,” he admitted. ‘He can?’ Where was this coming from? Prior to that explanation he was ready to rumble. What about that had made Crook seem—

Epiphany. “He’s a lot like you, you know?” I had an angle.

Mac’s ears raised.

“Crook, I mean. I’m like a little brother to him. We’re family. He likes to fight my battles for me.” This was my best play. Big Mac is clearly a family pony. After all he was out here looking out for his sister. When he’d heard that Crook was looking out for me, it suddenly seemed okay. He’s protective of his family, and I was going to use that to win some points with the big guy.

He squinted. Big Mac was having trouble making sense of what I was getting at. “Ah don’t see how—”

“Just like you are right now.” A tiny flash of panic told me I was right. “Applejack doesn’t know you’re here.” He tried desperately to find something to look at. His guilt came back in force. “How would she react if she knew you were here right now?”

“That… that ain’t…”

“I bet she’d be upset that you were butting into her business.”

Big purposeful deep breath. “A’right, what’s yer point?”

“My point is that I have just as much control over Crook’s actions as Applejack has over yours.” Time for a slight pity play. “I just don’t want anypony thinking I ‘sicced’ Crook on Applejack.”

“Ah never thought—”

“You didn’t. But what does Applejack think?” I asked.

“Ah don’t know.” Scratch at back of neck. “She’s been all worked up lately.” This was good. This was very good.

“Just lately?” I teased.

He laughed at that before catching himself. “Maybe she’s been a mite upset for a time now,” he admitted with a trace of a smirk remaining. ‘Okay, so he’s starting to warm up to me. This is good.’

“And again, I’m sorry about that. I’m not going to sit here and pretend I didn’t have a hoof in that. I’ve done a few things I regret in the course of this… little feud.” That one wasn’t a lie. I did feel shitty about that rainy night at Sugarcube Corner where I verbally eviscerated her.

Big Mac nodded solemnly. “I heard all about that one.” Meaning he hadn’t heard about this one from Applejack. Every bit of information helps.

‘Maybe Applejack feels partly to blame for what happened with Crook. Still, it’s tough to say. Too many unknowns.’

“Look, ah’m… ah’m sorry,” he said. Unexpected, but not unwelcome.

“What for?” I inquired.

“I… I assumed ya’ll were… well… ya’ll were just what mah sister was sayin’.” ‘Oh, this is very VERY good.’ “But ya’ll ain’t half bad, uh… Ah’m sorry, I didn’t catch yer name.”

“Guilty… Guilty Pleasure,” I responded, extending a hoof.

“That so?” he asked, disbelieving, as he took my hoof and shook it.

“Well, no,” I admitted. “But it’s the only name I use anymore.”

“Huh… Y’all are a character ain’t ya?” As the hoofshake ended the kettle began to whistle.

“That’s the kettle. I’ll be right back.” Off to the kitchen I went once more. So far so good. Big Mac was being amiable and, so long as I was working on winning him over, his presence wasn’t niggling at me that much. I returned to living room with our beverages as well as a small dish of crudités. Exceeding expectations is never a bad move, and it’s not hard to put cucumber and celery on a plate.

Big Mac cleared his throat as I hoofed him the mug. “Thank you,” he said, still hesitant.

“Careful, it’s hot.” As I returned to my seat, I took stock of my… well he wasn’t a client. Mark? No. Don’t want to think about that. Hmm… guest. He was my guest. Yes, that’s it.

He cleared his throat. “Thank you,” he said purposefully. Taking a sip, his body visibly relaxed. His shoulders drooped ever so slightly, and his lips curled into a hint of a smile. “S’good.”

“Thank you.” I took a sip of my tea, even though it hadn’t properly steeped yet. Hot and caffeinated, it was all I really wanted. The warmth spread through my chest as I swallowed my swill. Just the thing for a day like this. We enjoyed our drinks in relative silence. Big Mac’s not a very talkative pony, and he seemed to appreciate the quiet. He never partook of the spread I’d laid out, but the sentiment was what really mattered anyways.

When our mugs were empty, I decided to make another play. “So, Big Mac, I hope you won’t think less of me for… asking you a favor.” Feign anxiety. Fiddle with hooves.

“That all depends…” he responded. Even incomplete his statement was clear.

“I’d like you to let your sister know… that I’m sorry… for Crook, and for all the things I’ve said.” Act sincere, but also uncomfortable. Make eye contact, but blink a lot.. The more it appears it’s hard for you to ask, the more genuine your plea appears. That and the more pathetic you appear the more likely people are to take pity.

Big Mac took a deep breath. “Ah’ll do what Ah can. Not sure what good it’ll do, though.” I really didn’t care how Applejack took it; this little show was all for Big Mac. I was making myself look like an honest pony with good morals.

Not that I’m all that dishonest or immoral it’s just… well…

You have to defy expectation if you want ponies to think differently about you. The more you defy, the more different ponies think.

Hmmm… that sounds a lot like an excuse, doesn’t it.

Somtimes, I really think I might be a bastard.

Best not to dwell on it.

I don’t know. I really am sorry about what I said. That’s the truth. Crook’s little play, though? I rather enjoyed that. Maybe I don’t sympathize in the classic sense of the word. Maybe I just feel like I’m not responsible, so it’s okay. Maybe I’m not actually sorry, maybe I just feel guilty. Maybe I actually do delight in Applejack’s suffering.

Hmmmmmm…

I need a therapist.

Where was I? Ah, yes…

After his coffee Big Mac looked like he was ready to leave. I would’ve loved to try and grill him for information, but I’d rather win points than risk any with reconnaissance. “You should head out while that coffee is still keeping you warm.” I gathered up the mugs.

“Yup,” he responded, standing to his full height again. He’s pretty freaking enormous.

“Take care, now, Big Mac. Stay warm.”

He nodded, and left without a word.

Once the door was closed I couldn’t help but pump my hoof in triumph. ‘Score! That couldn’t have gone better! The brother thinks I’m an okay guy!’ I may have indulged in not-so-brief victory dance.

Could things actually be taking a turn for the better? I suppose only time will tell, to use a cliché.

That evening was one of introspection and drinking. After he was gone, the unpleasant mental images of Big Mac seemingly left with him. Interestingly enough, they sort of weren’t present once I had gotten into the swing of things. Again, I think I’m compartmentalizing. I had hopeful thoughts of a peaceful relationship with Applejack in the future. It’s a longshot, but hey, a stallion can dream.

And then came the inevitable. I began to worry about my upcoming… meeting.

Okay, date. It was a date.

I was doing what I always do when I have free time: preparing. I was running through possible conversations, debating wardrobe options, mentally prepping for possible faux-pas, running through magazines to brush up on anything I could think of topic-wise.

When the brain-racking worry became a little more than I could stand, I decided to exercise. Sit-ups and squats. The burn in my muscles was very cleansing. I’ve been slacking a little on my workout, so I was feeling more pain than usual. I need to go on a hike again soon, too. Gotta work on my cardio.

After exercise came a shower. After a teeth-chattering scrub down of the utmost thoroughness, I decided to pull a Derpy and just… meditate. Warm water is like a liquid blanket. Sitting there in the warm shower was almost enough to make me fall asleep. I didn’t, but I almost conked out. I don’t know why it’s so peaceful in the shower. I don’t think. I don’t worry. I just sort of… sit. Cheesy as it sounds, it sort of washes everything away. Maybe it’s the white noise. I need to test this theory somehow.

I almost shaved, but I decided I’d do it again before my… date.

So I wrote… well… all of this.

I…

I think I’m feeling pretty sad right now. It’s not like a… a tangible sadness, there’s no tears, no wrenching gut. It’s a sort of… low hum in the background. A song of woe playing in my life. Or, maybe it’s more like the sound of a fuse. A fizzle of depression building up to some greater unknown sadness. Further still, it might be more of a warning alarm. An internal alert of upcoming…

Heartbreak

That’s the word, isn’t it?

I… I don’t want to feel like that again. I don’t want to feel that… unwanted.

When I… I told Sunny how I felt, it was… it was instantly awful. I didn’t have to wait for her response to know what it was. The moment I’d opened my fat mouth, her face just…

Pity. It was the epitome of pity. She was looking down at me as I laid myself truly bare before her and… and she felt sorry for me. She was sorry for the feelings I had for her because she knew that they weren’t reciprocated. She pitied me…

… and I felt pitiful. I felt so small and weak and ineffectual and…

There must be a word. There must be word that means what I felt, because I felt like I was… nothing… like I didn’t exist. At that point in my life, I was aiming to capture the attention of one pony, and I had failed. It was as though the whole world couldn’t even see me.

She was so polite about it.

“I’m sorry, but I’m married. You know that, Guilty. This is fun, but… it’s not real.”

That’s all I was. Not real. I was imaginary.

She continued to see me after that. She gave me many a gift in that time. It pleased her to do so. Clothes, watches, expensive liquors, even gemstones, she gave me whatever she thought I might enjoy. She didn’t know that any gifts she gave me were sold off and the profits split between my madame and I. She didn’t know that every meeting, every date, every rendezvous was being captured on film.

I… I wanted to hurt her. I wanted her wits to fail her when the fateful letter was sent off. I wanted her to have to carry the fear that one day her unsuspecting husband to find out about her and my little tryst. I wanted her… to feel sad.

When I look back at that Guilty, I see… such a sad craven pony. I see a pony who just didn’t want to feel like he was suffering all alone, and was willing to hurt others, just to feel like he had some company at the bottom.

I don’t want to be that pony again. I don’t want to hurt Derpy the way I tried to hurt Sunny. I don’t want to hate her. I don’t want to be that small again. I don’t want…

...to write anymore.

I’m going to go to sleep.

Author's Note

Thanks to all the usual helpers. Aquapunkchick, JakeTheArmyGuy, coandco, and Blackskulls.

So, what did you think? There's more an the horizon, too, so get ready!

Throw me a fave and a thumb and a comment and all that jazz! It fuels and sustains me.

Dating a Client

Chapter 18

Dating a Client

Today was a day. Events happened and things took place. I saw ponies and said things and engaged in conversation.

There. I’m done. Time for sleep.

*sigh*

I’m not going to get away with that, am I?

Honestly, I’m just… still kind of in shock. I’m letting everything sink in. Today was...

Well, I’ll start with last night.

After I dozed off, I had an incredibly vivid dream. I was back in the stable, in one of the upstairs bedrooms. The red drapes on the windows, the faux-gold bedframes, it was just like it always was. The air was thick with sex and perfumes. Candles adorned every corner of the room, illuminating it with an orange glow. It so was warm. It was always warm in the stable, there was a hearth in every room and a dozen fires kept this building glowing with heat even in the dead of winter.

I was in ecstasy. Derpy was on top of me, riding me with passionate vigor. Her mane was ragged from our combined fervor and, for some reason, her eyes weren’t crooked. Her gaze bore into mine. I couldn’t stop staring into those sunset colored eyes. Entranced, I reached up,wrapped my hooves around her, and pulled her soft body into mine. She was so hot and sweaty and hungry. Her hips continued to gyrate tirelessly, engulfing my member. As our bodies thrashed in satisfaction, she leaned in…

… and she kissed me…

...on the lips.

Our tongues wrestled and our lips clashed in soft, wet passion. She tasted so salty.

It lasted… seemingly hours.

It was… nice… incredibly, amazingly, impossibly nice.

My climax was… peerless. Emptying my testes into her filled every inch of my body with pleasure. When my climax began to fade, so did the dream. I never got to see Derpy come.

Not that I haven’t seen that plenty of times.

When I woke up it was almost noon, and my sheets were absolutely coated in spunk. The remains of my fantastic (literally) orgasm. It made me feel… kind of childish, honestly, and maybe a little ashamed. I hadn’t done that in my sleep for years, not since before I was an escort. That said, waking up with a crusty coat and dirty sheets isn’t the worst thing in the world. It’s easy enough to fix: laundry and a shower. They solve so many of life’s problems.

Anyways, it was a pretty empty day until the date. I spent the better part of my morning deciding on an outfit. I briefly considered going in a dress shirt before coming to my senses and realizing how absolutely ridiculous of an idea that was. A dress shirt and jeans is just… awful. So I went with a polo shirt. I’ve got a pink one. It goes well with my mane, I feel. Jeans, as usual. I really wouldn’t feel right leaving home without them. And a nice warm overcoat. Not remotely fancy, but wonderously warm. I figured I could get away with it, since we’d almost certainly be eating inside. If there were any outdoor events, I would go with a dress coat, but I knew I’d be able to take it off once the date got going.

Having decided my outfit a full six hours in advance, I was left with little to do other than dither. My magazines were all read, my house was pristine, and my walk was appropriately shoveled. There was nothing for me to do… until the mail came.

There was a loud knock at the door. “Guilty! You have so many magazines!” shouted Derpy from beyond the confines of my home.

‘Derpy’s here. Derpy’s here now. I’m not mentally prepared for this. I forgot she delivers my mail now. Oh, my gosh. Why didn’t I plan for this?’ I didn’t lose my beat, like the day before. I answered the door properly. ‘Be calm, be natural, smile.’ “Hey, Derpy.”

There she was. The same mare I’d been literally dreaming about. “How do you read all these?” she asked as she hoofed me a sizable stack of print and paper.

I almost lost my balance as she hoofed me my subscriptions to Equestria Outside and Fashion Now and Cosmarepolitan and everything I read for the sake of clients. (Well, not EO, that one’s for me.) “*Unf* I don’t. I just read the ones I need to.” I placed my magazines on the table. I would deal with them later. “So, this is your new route?”

“Uh-huh! You’re my last stop, too.” She was panting. She must’ve been flying around for hours with my fat stack of mail. Part of me wanted to apologize. I mean, it was sort of my fault. But, I mean that’s her job, right? She glanced at the pile I’d placed on the table. “So how do you know which ones you have to read?” she inquired.

“It depends on the client. Some clients like to talk and I need to know a lot about what they like.”

She nodded. “That makes sense. Well, I’m gonna get going. See you tonight, Guilty!” Off she flew.

“Y-yeah! See you!” I called after her. The encounter was sort of surreal. I’d been preparing to see her on a date all day long, and when she shows up it’s unannounced and totally casual. Not only that but it lasted all of thirty seconds. If it weren’t for the sudden appearance of my monthly delivery, I would’ve almost believed that she’d never stopped by at all. It was as though she were only a dream.

No, the humor of that statement is not lost on me.

The anticipation was excruciating. I waited for hours with nothing to do. I mean, I have a lot of days like that. But when I know there’s something that I have to go and do later, it just makes the idle time so much more… idle.

Okay, that sounded kind of dumb, but my point is in there somewhere.

I tried to flip through some of the magazines, but my head wasn’t doing its job. Eventually, I just gave up.

The hours passed and passed, until finally it was time to go.

So, ready or not, I made my way to Derpy’s place. The majority of the trip was easy; there was snow on the ground but the sun was out, and it wasn’t too chilly. The last few steps though… they were kinda hard. When I got to Derpy’s home the sun had just set. There was smoke billowing out of the chimney, firelight in the windows. It was a happy, warm, little cottage.

‘Okay, Guilty, relax. It’s just a date. Not even a real date, it’s just practice. You’re good at dates. You’ve been on plenty of dates, and most of those were fake, too. Besides, all you’re trying to do is help Derpy. You like helping Derpy. Just relax, let it happen, and enjoy it.’

“Fuck it,” I whispered to myself, opening the front gate and rushing to the door. I swallowed all my anxiety. I reached out and knocked before I lost my spine. It opened with a creak, putting face-to-face with… no one?

I looked down. ‘A tiny unicorn…’ I’d been so concerned with what I was going to say to Derpy, I hadn’t considered the possibility of someone else answering. I blinked as realization dawned on me. ‘Holy balls, this must be Dinky!’ She was a darling little thing, the spitting image of her mother, messy blond mane and all. ‘Say something, Guilty. It’s first impression time.’ “Hi, there.” Gentle smile. Eye contact. “You must be Dinky.”

Her reaction wasn’t what I was expecting, but wasn’t to be unexpected. (That made sense, shut up.) She frowned and rolled her eyes at me. “Mooooom!” she called in a half-annoyed tone before retreating inside. It made sense; I’m sure she’s had to meet plenty of the stallions that Derpy’s tried to date. Anypony could get fed up with that. As she retreated into her home, she left the door open, which I took as an invitation to, at the very least, shelter myself from the cold.

“Hang on, I’m getting dressed!” came a familiar voice from beyond a closed door. Derpy’s home was pretty much the same as the last time I’d seen it. It was cluttered, cramped and a tad messy, but still very warm and cozy. Dinky was lying on the floor, making a crayon drawing that would no doubt wind up pinned on the refrigerator.

Terror began to dawn on me, as the nature of my situation became clear. ‘Okay, Guilty, don’t freak out, but you’re all alone with Dinky for an unknown amount of time. You can risk saying nothing and hope that Derpy comes downstairs before things get unbearably awkward, or you can attempt to hold a conversation with a child until her mother comes downstairs. You don’t have the greatest track record with kids, but at the same time, the stakes are pretty high. If you don’t get Dinky to like you, things are going to be rough.’

I decided not to be a total pussy about my situation and attempted casual conversation with a grade-schooler.

The most dangerous game!

“So… what’s that you’re drawing?” Nice and simple. A very safe play.

“Tank,” she responded, still slightly annoyed.

I wasn’t going to be rude, but her drawing didn’t really look at all like a tank. It was more like a helicopter, to be honest. “Well… alright then.” ‘Nice job. You got one word out of her. Try something a little more engaging.’ “So, um… how are you?” ‘Really? That’s engaging?’

“Fine,” she said as she grabbed a green crayon. Well, at least the color was right. ‘Well, we’re up to two words now. Another five minutes and you might have yourself a sentence.’

I rubbed my temple. Fucking kids. “So, you like art?” I asked, determined to get more than a single word in response.

“I guess.” Two words at once! Victory! Conversation achieved… sort of.

“I never liked art,” I admitted. “Never had a knack for it.”

She just hummed in response. My head fell. I am so bad with kids. It’s pathetic.

A savior came in the form of a bundled-up Derpy. “Hi, Guilty! Sorry I took so long.” She looked adorable. I was half-expecting makeup and a dress, but a giant puffy coat was fine too. “You ready?”

I smiled. Not a calculated polite smile, not an artificial hunky smile, not a practiced seductive smile, just a smile. All that dread that I’d had, all that fear and anxiety of how much it was going to hurt being on a fake date was just... gone. Out of mind. I was just excited.

“I’m ready when you are,” I responded a tad energetically.

She smiled back. “Alright!” She turned to her daughter. “I shouldn’t be gone too long. Dinner’s in the fridge.” She gave her a big noisy kiss on the head. “Say goodbye, Dinky.”

“Byyyye,” she droned, solely out of obligation.

Derpy looked up at me with eyes full of anticipation and a smile that was ready for anything. “Let’s go.”

We took our leave. Thankfully, it wasn’t snowing that night. The air was cold, but not in a “chill you to your bones” sort of way. The two of us walked side by side down the dark streets of Ponyville under an ever-dimming sky. “It’s not too bad out tonight,” I commented. Conversation rule number one: you can always talk about the weather.

“Yeah, it could be a lot worse,” she responded with a nod. “So how’ve you been, Guilty?”

I chuckled. “You saw me just yesterday, Derpy, and this morning. Not a whole lot has happened.”

“Yeah, well, I gotta brush up on my date questions. Just pretend you’ve got something to say,” she said, sticking out her tongue a bit.

“But what if he really doesn’t have anything to say?” I teased.

“Well… uh… I hadn’t planned that far ahead.” Her head sank. “Ugh… I’m so bad at this.” So hard on herself.

I felt kind of bad. Here I was, already enjoying myself, and Derpy was a ball of stress. This was the exact opposite of how I pictured this going. “Hey, relax. Just focus on having fun. Don’t sweat the small stuff.”

“Easy for you to say,” she whined. “I’m trying to get better at this. Go easy on me.”

“Alright, alright. Start over.”

“Okay… *ahem*… So how are you, Guilty?”

“I’m okay, Derpy. Business is okay. What about you?”

“I’m doing good. Mister Crate hasn’t yelled at me in a while.”

I scoffed. “Wow, that’s a downer.”

“Huh?” She looked up at me, perplexed.

“When you say it like that, you make it sound like he yells at you a lot,” I explained.

“But, he does.”

“And that’s a downer,” I pointed out.

Derpy brought a hoof to her chin and hummed. “I guess so. Thanks, Guilty.”

“Any time.” I took a moment to examine our surroundings. It occurred to me I didn’t know where Derpy was taking me. “So, where are we headed?” I asked.

“Huh?” Her eyes bulged slightly. “But, I was following you!”

I blinked. “Whoa whoa whoa, you asked me out. You gotta have a date prepared,” I teased her once more.

“Oh… uh… okay… um…” Her gaze shot around for a moment as she searched the streets for a proper venue. “Okay… I know a restaurant. It’s, um…” she spun around once before determining a direction. “… this way.”

I chuckled. “My gosh, you are too cute,” I said, entranced by her adorable little confused twirl.

She blushed. “W-why are you saying that?” She hid her reddening cheeks behind a foreleg.

To be clear, those were the cheeks on her face…
.

… Okay no more sex humor, I’m getting bored of it.

I giggled. “I’m complimenting my date. You did something cute, and I commented.”

“But… I didn’t… I’m not cute!” she insisted with a stamp.

“Yes, you are.” My words were equal parts sincerity and whimsy. “Learn to take a compliment. Dates tend to try and flatter you.”

Her face scrunched angrily, but she nodded.

I continued to follow her down Ponyville’s streets until we reached a small restaurant. It was a cute little place; a few snow-covered tables sat outside, but the inside was pretty packed.

I love the din of a full restaurant. Clacking silverware, low conversations, it all forms a very comforting background. When we stepped inside, the air was warm and inviting. It was no wonder it was so crowded; it was the perfect respite from the weather outside. “Table for two,” said Derpy to the hostess.

We were crammed into a little couple’s booth. I tried not to focus on everypony else as I read the menu, but it wasn’t exactly easy. More than a few townsfolk couldn’t help but gape at the whore out in public… with a mare… on a date.

“That poor dear,” somepony whispered. “Is she paying for this?” another voice inquired.

Ugh… gossip gossip gossip. Derpy didn’t seem to notice; the menu had her full attention. I felt so bad. Even if Derpy was determined not to let it get to her, this date was affecting her public image. ‘Just leave, Guilty. Excuse yourself. You’re making her look bad. Just see her in private, at your place or together with her friends. This is too open. Too exposed.’

“Whatcha gonna get, Guilty?” I hadn’t actually taken a look at the menu; I’d just been using it to shield myself from the judging gaze of others.

“Uh…” There was a decent selection. Sandwiches, pastas, soups salads, all the staples were there. “That second spaghetti dish looks pretty good.”

Derpy glanced back at her menu. “Bleh… eggplant. I’ll pass. I think I’m just gonna get some soup. The tomato soup’s really good here.”

“Yeah, it’s soup weather, all right.” I folded up my menu and put it down. I needed to come up with some “date things” to say to Derpy if I was going to help her out. “So, what do you do?” I asked her.

“Huh? I’m a mailmare, you know that,” she said, slightly confused.

“Practice, Derpy. It’s for practice.”

“Oh, right… um… ask me again.”

I nodded. “So, what do you do, Derpy?”

“I’m a mailmare here in town. What about you?” Not at all bad. A fairly natural delivery. She’s not as rusty as she thinks.

“I repair watches. I have a little shop in town,” I lied.

“Buh?” Flabbergasted.

“You never know what your date will say. You have to be ready for anything.” I stuck a tongue out at her.

Derpy’s eye’s narrowed. “You’re having fun with this aren’t you?”

I smirked. “Maybe a little.”

Her stern gaze vanished as she giggled at my playfulness. “You’re so silly, Guilty.”

When the waitress came to the table, she did her best not to stare. She wasn’t a client, but she knew who I was. “M-may I take your order?” She tried her damnedest to be polite, and she succeeded for the most part. She failed to make eye-contact, but hey, no big.

“I’ll have the House Pomodoro and a glass of red. Derpy?”

“Can I get a bowl of tomato soup?” she asked eagerly.

“Of course.” She swallowed nervously. “Anything to drink?”

“Oh, just water,” she responded.

“Great.” She turned to leave before doubling back. “Oh! Let me just get those, uh… those menus for you.”

I almost shook my head as I hoofed them to her. ‘Don’t stress yourself, we’re barely paying attention to you.’

“So, what’s it like being a watch-repair pony?” Derpy asked with a roll of her eyes. I guess she decided to play along.

“Well, it’s kind of nice. I make my own hours, work from home. There’s not a lot of time outdoors, though. I spend a lot of time at home… alone.” Exaggerated sigh.

“Now who’s being a downer?” she accused. “Lemme guess… ‘you never know when your date is going to be a downer?’”

“Something along those lines,” I admitted with a giggle. “That, and it’s fun to role-play.”

“I guess.”

“So what about being a mailmare? That’s got to be tough.”

She shrugged. “It’s not so tough. Mostly it’s fun, ‘cause I get to say hi to everypony all day long.” Her features all lit up. She really does love her work.

“You’re just too darling, aren’t you?”

She blushed again. “Stop complimenting me, it’s embarrassing.” Protest as she might, she still smiled at my flattery.

“Get used to it. It’s not gonna end any time soon.” I cradled my chin on my hooves. I was taking such delight in my own impishness.

She groaned in response. “You just like watching me suffer, don’t you?”

“I’m not going to lie, it’s actually kind of fun. You look so cute when you’re embarrassed.”

“Oh… cram it.” She laughed despite herself. “It’s actually kind of nice… I don’t get that a whole lot.”

“Downer,” I chided.

She just glared at me. “Anyways, thanks again for this, Guilty. Practice or no, it’s nice to get out of the house.”

“Agreed. It’s been a while since I had dinner at a proper restaurant.” I pondered briefly. “Actually, I didn’t know Ponyville had any proper restaurants.”

Derpy emitted a charming giggle. “Only a couple. They’re just some family run places. The food’s super good, though. I bring Dinky here all the time.”

“Who’s Dinky?” I asked pointedly.

“Ah.” Derpy caught on to my meaning. At some point in her date she is going to have to explain that she’s a single mother. “But I mean, everypony in town knows about me anyways, it’s not like I’m going to have to tell them.”

“That’s true. I forget how small towns work, sometimes. Everypony knows everypony.”

“Yeah, well...” Derpy just shrugged. “... it’s not all good.”

I chuckled. “I never said that that was good, Derpy.”

She waved a hoof at me. “Oh you… but I’m serious, everypony knows all about… well everything.” Her meaning was clear.

“I don’t.” I spoke before I realized what I was saying. I’d caught bits and pieces about it from Derpy, but she never really talked about him. I caught myself. “I’m sorry, I didn’t mean to—”

Derpy shook her head. “It’s fine. I mean, it’s kind of…”

“A downer?”

She nodded. “But, it’s not like it’s a secret or anything. Everypony knows.”

“I’m sure, but that’s not why we’re here. You don’t have to—”

“I don’t mind,” she interjected. “Really, I don’t. If you’re curious…”

“Well…” I mean… it’s something that would’ve come up eventually, right? She already tells me just about everything. And if everypony already knows, there’s nothing weird about talking about it public, I guess. “... sure. Tell me about him.” I’d always wondered, honestly, about Dinky’s father. I’d just thought it wasn’t appropriate conversation for, well, Derpy’s and my relationship. But if she was offering, so… why not?

“Well,” she began. “His name was Dusty. He was from Canterlot, and he was an archaeologist for the Royal Historical Society. He came to Ponyville to study the old castle in the Everfree Forest.”

I didn’t know there was a castle in that forest, but I wasn’t really paying attention to that at the time. I am curious about that though. I’ll have to ask somepony about that at some point.

“I was just out of school, and had started working as a mailmare. I was making a delivery to the hotel he was staying at and we met in the lobby, and… four months later we were married. Ten months after that, Dinky came along.”

‘Only ten?’ I would’ve joked about a shotgun wedding if I could’ve brought myself to speak. I was just in awe, this story it was just so… real. I’ve said before, I primarily deal in the artificial, so when a story this… true was being told to me, I couldn’t do anything but absorb it.

“For a while I was a stay-at-home mom. I lived with my parents and raised my little girl. Dusty would disappear for weeks to go investigate some new ruin or another. He always came back, though… until he didn’t. This was years later, I’d moved out of my Parent’s place and they’d moved down South and we had a nice little house that we lived in. I got a knock at my door and some very bad news. There… there had been a cave-in, and Dusty…” she swallowed hard. “... didn’t make it.” She fought back her tears with ease, but there were certainly tears to be fought. “Sorry, I *sniff* told you it was a downer.” She looked up at me and her face became one of concern. “Oh, don’t cry, Guilty.”

‘Am I crying?’ I reach a hoof to my face in shock, and sure enough it was moist. I’ve heard plenty of sob stories in my day, but I’d never really been moved to tears. This, though… apparently it was too much. “I-I’m not…” I wiped furiously. “Okay, yes I am.” Ponies were staring. I was emoting. I needed to leave.

“I’m sorry, Guilty. I wasn’t trying to…” Her head fell once more. “I’m a terrible date,” she lamented.

“N-no, Derpy. It’s fine, it was just…” ‘Get out. Collect yourself.’ “...a lot to take in.” I grabbed a napkin and wiped away my tears. “I’m just going to use the bathroom.” I swiftly retreated, doing my best to hide my face from the eyes of the townsponies.

I needed a mirror. I had to assess the damage. I found the bathroom and, with a nervous spring in my step, trotted to the mirror.

‘Yup! That’s the face of a grown-ass stallion crying, alright.’ I took deep breaths. ‘I just need a moment. I need to breath. In. Out. In. Out.’ Even steady breaths didn’t come as easy as I would’ve liked. My lungs wavered as tears were denied existence. I tried not to think about Derpy. I didn’t want to think about that… that sadness she must carry with her every day. I’d seen her a bawling mess of tears, but this was a heavier sadness, and engulfing sadness. I hoped… I prayed, that I’d never have to see what her face looked like when she got that news. I hoped she’d never have to wear an expression like that again. I just… couldn’t comprehend a Derpy that was that sad.

Smiling is her special talent. A face like that wouldn’t suit her.

Fuck, I’m crying again.

So, I proceeded to clean myself up. I’d managed to swallow most of my tears, but my eyes still showed a the telltale signs of crying. I silently cursed myself for not bringing any makeup. When I returned from the bathroom, our food had arrived. Derpy was already happily slurping away at her soup.

‘Well, time to be charming again.’ “Sorry about that.” ‘That was charming?’

Derpy put down her spoon and twiddled her hooves. “No, I’m sorry. I didn’t mean to make you cry.”

“You didn’t, you just…” ‘Change the subject.’ “...started eating without me.” I managed to smirk, as I forced myself to be playful. “How rude.” I stuck my tongue out a tiny bit.

Derpy’s brow furrowed. “Oh, right.” She shrugged and continued to… eat… drink… whichever… her soup. “That one’s not so bad, right?”

“Indeed it’s not.” I took my seat and sized up the meal before me. It was a positively massive portion, easily two meals. I would be taking some home for certain. It was a nice looking dish, too. The veggies and the pasta and the sauce, it all looked simply scrumptious. I took a bite. It was good, very good. With all of Ponyville’s quality ingredients it’s to be expected, but still, I was impressed.

The wine was okay, less than stellar.

Soon my tears were forgotten and our date continued. As we ate I continued to tease and flatter Derpy in equal measure. Whether or not she would admit, I think she enjoyed both. The meal carried on splendidly. We ate, we laughed, Iended up drinking a couple glasses of wine. It was…

Heaven…

…and then it ended.

When the check came and I could feel the evening coming to a close, the high began to wear off. I was becoming painfully aware that this was all just… pretend… again. After our meals were gone, and the check came… I suddenly found myself not enjoying the evening.

I paid, of course, and we took our leave. As I escorted Derpy back home, snowflakes began to fall ever so gently onto Ponyville’s streets and rooftops. Derpy must’ve thanked me a dozen times on the way back. She said that she had fun, and felt much less worried about going on proper dates again.

I just smiled as best I could, and assured her I was happy to help.

When we got back to her place, I could feel… I could feel my heart breaking. Another session was coming to an end, and I didn’t want it to. The little fantasy Derpy and I had indulged in was coming to a close, and it was time for us to return to our respective realities. The fun was... expended… used up… consumed, and Derpy had gotten everything out of me that she needed, as she always does.

Downer.

“Well, thanks again, Guilty. I really appreciate it.”

‘Be strong.’ “Yeah, it was no trouble. I had a blast.”

“Me too. See you Sunday?”

‘Be Strong.’ “Of course”

She nodded. “Mmkay!” We arrived at her front gate. “Here we are!” she announced proudly.

‘Be strong. It’s almost over. You can go home and have yourself a good cry.’ “That’s right… well, uh… I’m looking forward to your next visit.” It was truer than she knew.

She smiled warmly. “Okay. Good night, Guilty.”

“Right…”

I was about to say goodnight. I was about to march home with my head hung low, crawl into my shower, and weep until passed out. I was about to go throw my own private pity party as the pain of unrequited love coursed through me; It’s a pain I’m not a stranger to. I was about to go and let my metaphorical dam burst. I was about to let my feelings continue on, unrequited, as Derpy went out to date stallions and have a whole life of her own. I was about to do a hundred hundred cowardly, lonely, safe things all alone in my big, chilly cabin on the edge of the woods.

But then I did something fucking crazy.

‘Ah, fuck it!’ some voice within me chimed.

I swallowed hard. “So, Derpy, do you want to do this again sometime?”

I could’ve sworn my heart had stopped. ‘Did I just say that? I just said that. Am I doing this? I’m doing this.’

Derpy seemed rather confused. “Why? Think I need more practice?”

I shook my head. The rest of me was shaking as well, and it had nothing to do with the cold. My hooves trembled, my chest literally shuddered, my mouth was dry and my tongue was paper. “No, I… I mean…”

‘Make something up, you’re not committed yet.’

“…I mean…”

‘You don’t have the guts!’

“I mean for real.”

That had just happened. That had actually just happened! I had gone balls deep on the first thrust. I had gone from accepting that a love could never be to pursuing it!

I honestly cannot say… why I did that. It was just so very… not me. It wasn’t self preservation, it wasn’t the path of least resistance, it wasn’t… Guilty.

Which I guess means that Sour Dough was the one that spoke up.

Maybe I’ve got balls I don’t know about out.

Regardless, at that moment I wasn’t pondering any of this. All I was doing was waiting for response. I’m not sure how long I was actually waiting, but it felt like minutes. Derpy’s face was stone still in a bewildered visage. When she finally spoke her voice was quiet. “Are… are you serious?”

‘Say no. You weren’t serious, you were just messing around. You can still get out of this.’ “Y-yeah.” My voice was wavering. “W-why not?”

Something new began to creep into her expression. Her lips curled and her brow furrowed. I did not like what I was seeing; a slow burning anger was building up in her. ‘Well, you’ve done it now.’ I was ready for her to shout at me. To scream and rant about… something. I’m not sure. I closed my eyes and waited for some inevitable tirade.

Instead she just punched me in the chest.

“Oof!” I reeled back from the blow. It hurt, but was by no means meant to harm me for real.

As I regained my composure, I found an accusing hoof thrust at my face. “You lied to me!”

“I…” I let her statement knock around my head as I tried to make sense of it. When my brain came back with nothing, I responded rather dumbly. “Huh?”

“You said…” She tapped me in the chest again. “… that escorts. Can’t. Date. Clients.” Each word was punctuated with another angry jab.

“Ow!” I rubbed what would surely be a bruise later. “I… I did? When?”

“Forever ago! You said it was a rule or something!” She was almost screaming at this point. I didn’t remember ever telling Derpy that, but apparently it had come up.

“W-well it is.” I could feel my heart beating in my chest. I mean really feel it. ‘I-I just—”

“That’s the only reason I didn’t ask you out, like, a year and a half ago!”

I took a moment for her words so sink in. “Hang on. What?”

Derpy shrugged angrily, if that’s possible. “I mean…” She stared at the ground, looking for her next words. “...I was kind of asking out everypony at the time. I would’ve asked you too if you hadn’t said that!” Jab.

“Ow!” I rubbed my chest. “You keep hitting me in the same spot.” Definitely gonna be a bruise. “And… um… okay, I’m not sure where that puts us.”

“Neither do I!” I’d failed to notice that Derpy appeared just as embarrassed as she was angry. Her anger, however, began to subside as she physically relaxed. A blushed filled her face as she realized how heated she’d gotten.

“Um… w-would… would it be okay?” Her voice was almost a whisper again.

“Y-yeah,” I replied weakly. My face felt hot. I’m sure the two of us must’ve been quite the sight. Just a couple of ponies, standing out in the snow, blushing up to our ears. Neither of us were making eye contact or speaking anymore I don’t think I’ve known a more awkward moment. So, we stood, neither of us knowing what to say.

I said something anyways. “I… I think I really like you.”

“O-okay.”

Silence again.

Everything was sort of up in the air. On the one hoof she seemed at least okay with the idea, but on the other hoof she wasn’t saying anything. ‘This is weird. This is so weird. What am I supposed to do?’

“I’ve made this very awkward, haven’t I?”

“Heh, maybe a little.” Our eyes met. “Actually, now that the shock’s wearing off, I feel a little better.”

“Well, that’s good. Um… so… do you wanna…” I swallowed. “...do this?” I asked, trying not to sound desperate.

“Well, yeah.” She chuckled nervously. “I mean, it’s worth a shot, right?” She smiled, before clearing her throat. “Sorry I punched you.”

“It’s okay. I was just worried that I’d made you upset,” I admitted.

“No, you… well… yeah, a little.” She giggled. Apparently she was giggling again. “More than anything I just wasn’t expecting it.”

“Sorry, it was... kind of a surprise to me, too.” My frantic heart rate was dropping, I’d stopped sweating, my breathing returned to normal. All the adrenaline was wearing off. “I can’t believe I actually said something.”

“You can’t believe it?! I thought that this could never happen!”

“Well, me too, a little.” We both giggled at that.

“So, um… you wanna talk about this tomorrow?”

“What’s to talk about?” she asked innocently.

I had a thousand responses. There were details to attend, wrinkles that needed ironing out. What gets told to Dinky and who tells her? How often do we go on dates right now? Do we even go on dates, is that a thing? I mean we’re dating now, right? Or trying to? Or starting to? Or… something? Do I keep charging you for sex? Do we still even have sex? Can we go hiking more? Can hiking be a date? I’d like hiking to be a date occasionally. Where is all of this going? What’s our endgame plan? Marriage? Children? There was so so much to talk about.

“Nothing, I guess. So um… just until Sunday?”

“Yeah sure, unless you get a letter.”

“O-okay, yeah… um… you could just stop by whenever, if you like. If I’m not with a client, you can come in. I can cook you something, or something.” I must’ve sounded so desperate, but Derpy smiled regardless.

“If I’ve got time.” She smiled.

“Okay.” She seemed… eager? ‘That’s good, right?’

“Um… Guilty?”

“Hmm?”

She shifted uncomfortably. “Do you wanna…? Can I…?” She took a breath. “Can we kiss?”

‘Oh…’ “Oh…”

“I mean… if not that’s fine, it’s just… never mind, it’s not—”

“Nonono, it’s… fine.” ‘Is it?’

“You don’t seem so sure.” She put a hoof on my shoulder. “Don’t push yourself, Guilty.”

“It’s not… no it’s fine, it’s just... um… I never… I’m not very—”

“It’s fine, Guilty, really. Don’t worry about it.”

“N-no, let’s do it. I’m just… not very good at it.” And there was all that nervousness again.

“If you’re sure.”

“I am.” I actually think I was.

So we… kissed… for about a minute. It wasn’t… quite what I was expecting. The kiss in my dream was just… perfect, a fusion of flesh and fluids. The reality, though? Our teeth kept knocking together. My tongue was kind of all over the place. I bit her a little bit too hard at one point. At the end of it, we were both feeling sufficiently awkward again. Derpy was the first to speak this time. “Guilty?”

“Yeah?”

“You’re a really bad kisser,” she said with a laugh.

“Sorry.” My head sank.

“It’s okay. It’s kinda cute actually,” she teased.

‘Cute?’ “I-I’m not cute,” I stammered.

She stuck her tongue out at me. “Now you know how I feel.” She opened her front gate and began to walk away. “Goodnight, Guilty.”

‘She’s leaving?’ “G-goodnight.” I watched her as she walked back into her home. Her hips seemed to sway a little more than usual as she strode. When she got to her door she turned, she waved, and she disappeared inside.

And I sprinted home.

I had to write right away. I couldn’t believe it. I couldn’t believe it! Nothing was a hundred percent certain yet, but we were going to give it a shot.

A shot, I have a shot!

I still can’t wipe the smile off my face.

And on that note, I’m going to go to sleep. I don’t think I can feel any better than I do right now, and I want to try and carry that into tomorrow.

Author's Note

So here's a chapter that I'm sure half of you have been waiting for since Chapter 3.

Once again, like, comment, follow, fave, all that jazz. It fuels my glorious golden ego!

Thanks to all my editors: BlackSkulls, aquapunkchick, coandco, and Jake The Army Guy.

Now listen here guys. Go ahead and check my blog for the potential to have your own OC appear in my story! I've done it once before and I've been considering doing it again. Check the link below for details!

http://www.fimfiction.net/blog/274985/new-chapter-and-news

Charity

Chapter 19

Charity

Today started as well as it could have. I slept like a baby. Actually, I’ve been sleeping well since my date with Derpy. It’s nice, I’ve had a lot more energy lately. On top of that, each of my sessions has gone swimmingly: a perfect vanilla session with Ambrosia, a surprisingly rough afternoon with Bottlecap, a lovely romantic night with Rarity.

Actually, Rarity’s session was pretty fun. She spent a large portion of the evening trying to get the inside scoop on Derpy and me. She’d heard a dozen different things from a dozen different ponies and just had to know what was going on. I teased her all night long, and gave her nothing solid; it was very enjoyable.

So yes, the business side of my life is going well and the bits are coming in. As a matter of fact, I’ve been even busier than normal. My evening out with Derpy got ponies talking, it seems. When ponies talk, ponies walk. That’s really just a cute way of saying that some new gossipy mares have become clients. They’re mostly harmless.

Today, however, was Saturday, and my first free day all week. I didn’t have a client until Derpy tomorrow and I was looking forward to a day of relaxing indoors. The snow was deep, my fire was warm, and nothing in the world sounded better than a double helping of Waffle-Bitz. Cakes of maple wonder floated atop a sea of white gold. A bowl filled doubly high with sugar treasure sat before me. It was heaven… until half-way through when it got soggy. I always forget about the downside to a double helping: you have to eat it twice as fast. You can’t savor it nearly as much. Still, I downed the maple slurry of cereal mush.

Doesn’t matter; had breakfast.

So, stomach full, I set about to loaf about. My house was clean, my schedule was clear, and I was ready to laze around the house all day. I put my bowl in the sink and promptly parked myself in front of the fire.

‘Ah, this is perfect. A warm fire, a perfect afternoon, I can do anything I want.’

An empty moment passed, nothing but the crackle of the fire.

‘I want to go hiking.’

It was snowing out and my snowshoes still hadn’t come in.

‘I want to go see Derpy. I can do that now, right?’

Maybe I could’ve, if I had any idea of what her work schedule was like, or if I had made any plans.

‘I want to go hiking with Derpy.’

I wasn’t getting anywhere.

I rubbed my temples. I had my first free day all week and had absolutely nothing to do. ‘I could… reorganize my house.’ That didn’t exactly sound like the thing to do on a self-proclaimed day off. ‘I could… read my magazines.’ That sounded like a chore more than anything; I’d already read EO, and that’s the only one I really enjoy. ‘I could… go into town.’ Did I really want to risk ruining an otherwise perfect day?

I pondered that question for a moment. On one hoof, without anything to do, this day was going to one great big nothing. On the other hoof, I didn’t want to risk running into Applejack unless I absolutely had to. This was a toughie. There was snow on the ground, but the sun was shining. No market today, but that meant fewer ponies out and about. I had a pretty full wallet at the moment and the shops were open, but there wasn’t anything I actually needed. Applejack continued to exist…

‘… but, I might run into Derpy.’

I sighed. So, I was this guy now? The guy who was always thinking about the girl? I groaned aloud and, silently accepting my fate, got my coat.

It was a nice day out, for winter: coat-worthy, but not freezing. The streets were mostly empty, save the small fraction of the population as bored as I was. I decided my first stop would be Sugarcube Corner. It’s close and I was in the mood for a post-breakfast desert. Plus, Pinkie Pie is a friend. I was sure I’d enjoy her company for a bit.

Or at least I would have, if she’d been there.

“Well, hello there. Can I get you anything, Dearie?” She was big, whoever she was. Big, and loud, and frankly a little garish. She was bright blue, with an equally bright pink mane, and was pretty thick in the hips. ‘Oh, this must be the owner,’ I realized. “Oh, a new face! Well, welcome to Sugarcube Corner. Let me know if anything looks good.”

“Yeah, hi,” I responded absently. I wasn’t exactly in the mood for an introduction. I figured I’d just buy something and get out. ‘Ooh, those tarts look good.’

“So… are you new in town?” asked the large lady. She was just trying to be friendly, but I really didn’t want to do this.

However, etiquette lessons kicked in, and so, I acquiesced. “No, I’ve been here for two years now.”

Her eyes bulged slightly. “Oh, is that right? I’m sorry, we just… must not have crossed paths.” She seemed embarrassed. Maybe she realized who I was. “Well, I’m Cup Cake, my husband and I own this little place.”

And there she went making it clear that she’s married, as though I were trying to seduce her. Yup, she definitely realized who I was.

‘Relax, Guilty, she didn’t mean anything by it.’

Deep breath. “Nice to meet you, Mrs. Cake,” I said with a forced smile. That’s a little trick. People tend find you less threatening if you call them Mister or Missus; it comes in handy on occasion. “Guilty Pleasure,” I said with a slight bow.

She looked mortified. “I beg your pardon.” It appeared she thought I was propositioning her.

Impish chuckle. “My name, it’s Guilty Pleasure.”

She blushed. “Oh, I… of course. It’s a pleasure to meet you Mister… Pleasure.” She laughed at her own faux pas. “Oh my, people must say that all the time.”

‘This is agony.’

“It does happen from time to time.” I decided to just pick something and cut this little encounter as short as possible. “Can I get a couple of those plum tarts?”

“Of course, Dearie. Though, you should try them in the summer when they’re in season.” She scooped the pastries into a paper bag. “This time of year we make just make them with canned plums. It’s really not the same, you know?”

“Sure thing. I’ll be sure to do that.” I moved to grab my wallet.

She lifted a hoof. “Ah-ah! On the house, I insist.”

Surprising. “Really?”

“Oh, it’s the least I can do after I didn’t so much as say hello for two years.”

I wasn’t going to argue any more. “Well, thank you very much. Again, it was nice to meet you.”

“You too. Have a good day, now!” she called as I took my leave.

Once outside, I ran a hoof down my face. Why must every interaction take an hour and a half? In Manehattan, I wouldn’t have been in that bakery for thirty seconds. In. Out. Done. I definitely miss that.

Hmm…

Maybe I should take a trip back, soon. I could afford a couple days at a hotel, and Crook would love to see me. Maybe I could take Derpy.

There I go again. I’m like a love-struck little colt.

A hopeless romantic, I suppose the expression is.

Anyways, I decided to walk and eat. I ambled down the streets, nibbling at one of the tarts. It was all right. As I walked, I began to realize I didn’t really know where I was going.

I took a moment and tried and decide on a destination for myself, when I sort of realized… why bother? I could just wander, couldn’t I? I didn’t think I had to worry about being mugged in Ponyville.

‘Alright, I’m going to do it. I’m just going to wander aimlessly for a while.’

And so, for the first time in the two years I’d lived there, I walked around and really got to know Ponyville. It really is true, that everypony knows everypony, and I suppose it’s even begun to apply to myself. It’s not just my clients, either. I’m beginning to recognize other ponies as well.

‘There’s that stallion that’s always with Shoeshine. Her boyfriend, I think. Hmm, I’ve seen this mare around. She has a kid, right? Oh hey, there’s the guy who pulls the rickshaw.’

I suppose it can’t be helped, Ponyville is rubbing off on me.

‘That’s the creepy plum stall guy, he weirds me out. Okay, I see her coming out of town hall, a lot. She must work there. Now, that’s… oh, it’s Lily and Carrot Top.’

Sure enough, Golden Harvest and her lovely girlfriend were making their way right towards me. As the two of them walked, I saw something I’d never seen before. Carrot Top was smiling. Now, this wasn’t the fake smile she put for Derpy and her friends. This was a real smile, full of life and mirth and real happiness.

When she saw me it cracked.

It didn’t vanish or fall; it just went straight from a real smile to a fake one.

At this point Lily hadn’t yet noticed her partner’s reaction or my presence. We shared a look in that moment, Carrot Top and I. And in that look there was a mutual understanding. We were both going to pretend we hadn’t seen each other, and pray that Lily didn’t see me.

Now, I found myself with a rather curious dilemma. I had to figure out how to be as inconspicuous as possible as I walked past Lily, while simultaneously doing as much as possible to make myself unrecognizable.

‘Okay, thirty seconds tops. What’s the plan? I could just go eyes forward, and make as few movements as possible. I don’t know, on the off chance she turns she would recognize me. I need an excuse to hide my face. I could rummage around in my saddlebags, but that might draw her eye too, and I may get recognized regardless. Is there a middle ground?’

I was running out of time. If I was going to do anything, I needed to do it quickly.

‘I’ll just glance away if she turns her head, that’ll be sure to—’

“Oh, hey! It’s Mr. Pleasure.”

‘Fuck my life.’

I mustered a grin and feigned surprise as I turned to the couple. Carrot Top tensed as I responded. “Hello, Lily. Hello, Ms. Harvest.” I gave a small nod. “How are you two doing today?” It was time for another mandatory exchange of pleasantries. I prepared myself for the inevitable inanity.

Lily was, of course, the one to respond. “Oh, we’re fine. Just out for a little walk, getting out of the house, you know.” She tried to share a fond look with her lover. Carrot Top just feigned one. “What about you?”

Friendly smile. “Oh, pretty much the same, just strolling. I grabbed a couple tarts from the bakery and felt liking walking them off.” Yes, the three of us are simply out for the sake of being out. Without this exchange we might never have known for what purpose we had left our respective domiciles. Thank the sun we took this time to check in on each other’s schedules and motives, or else we might have wondered about it for years to come.

Small towns… I’ll never truly get it.

“You know, you should really get the tarts in the summer; they’re just not the same around this time of year,” Lily assured me.

“So I’m told.” Smile. Nod. Angle shoulders to indicate a desire to keep walking. “Sorry to stop you up and all, I’ll let you two get back to your—”

“Nonsense, Guilty. I stopped you. Anyways, there was something I wanted to ask you.” Carrot Top’s ears perked up, and her face betrayed her concern. I could see the gears turning, she was expecting Lily’s question to be about her. She didn’t wait to see if her fears were correct.

She grabbed Lily’s shoulder. “Come on, Lily, we don’t need to bother—”

Lily glared. “I’m not bothering, him. It’s just a question.”

She turned back to me only to be tugged away by a firm hoof. “He seems busy. Come on, Lily.”

Lily brushed said hoof off. “What has gotten into you?” she asked in a tone that reminded me a little too much of my father.

Carrot Top’s pupils shrank, as she backed away. “I… I’m sorry, I didn’t mean—” Poor, poor mare. She’d let baser instincts get the better of her, and fear made her act irrationally. Poor, sad Carrot Top.

As much as I would’ve enjoyed watching Lily torment my least favorite client, I decided to clear the air. It seemed the like the least messy option, at the moment.

I harrumphed. “I’m sorry, I think I’ve set you two off again.”

Lily looked mortified. “Oh, oh nonono, Guilty. You didn’t… I’m…” She sighed. “I’ve made a scene again, haven’t I?”

I shook my head. “It’s fine.”

She didn’t seem so sure. She turned to her partner with a frown. “I’m sorry, dear.”

Carrot Top just seemed happy she wasn’t being chewed out. “I-it’s fine.”

‘Okay, let’s expedite this ordeal.’ “What was it you wanted to ask me?”

Lily’s ear twitched. “Oh, I was just wondering if you and Derpy are dating now.”

Carrot appeared shocked. “Why would he be? Why would you ask that?” was her automatic response.

Lily ignored Carrot Top’s rather rude outburst. “Well, Derpy brought him to girl’s night and Primrose said she saw the two of them on a date. Not that I’m one to gossip.” She turned back to me with an eager expression. “Well?”

I opened my mouth to respond, but it took me a few seconds to realize I didn’t actually have an answer. As I stood there, slack-jawed, I tried to figure out what, exactly, I should say. Or rather, what I could say.

‘Can I… talk about this? Is this fair game? I mean… she said we’d give it a shot, but does that mean we’re… dating? Are we still in some sort of pre-date limbo? If we are, am I even allowed to talk about it? I mean it wasn’t a session, but… does that mean that it’s not private?”

These questions were rather new to me. In the past, clients were clients, and that meant everything was a secret. It was an ironclad rule. Derpy was a client, but she was… more than a client. She was a friend, maybe even a girlfriend.

Girlfriend… it still seems so surreal to think that I might have a girlfriend.

Surely we weren’t that far along, though, right?

I realized Lily was still waiting for an answer. Feeling a tad on the spot, I threw some words together. “I’m… not… sure.” I wasn’t sure how she was going to take that.

She grinned, oddly enough. “Say no more, I know how complicated things can be. You have a good day, now.” And with that, she continued on her merry way.

Carrot Top, on the other hoof, was clearly nonplussed. She’d scarcely taken notice that Lily had left, and just stared at me, mouth agape. “What?” she breathed, shock quickly turning to anger. Her scowl could strip the bark from a tree.

I took Lily’s absence as an opportunity to be a bitch. I smirked. “I know, I can hardly believe it, myself.”

The mare was livid. “What in the name of Celestia are you—?”

“Ah ah ah, Carrot Top. Don’t want to keep your girlfriend waiting. She might come back and hear us.” I stuck my tongue out at her. “Better skedaddle.”

She took a quick look at Lily. Back to me. Back to Lily. Back to me. “This isn’t over,” she huffed before chasing after her escaping lover.

I couldn’t help but give a contented sigh. ‘Who doesn’t love fuckin’ with ponies?’ I’m sure there would be hell to pay at my next session with her, but that’s alright. That confrontation was inevitable, anyways. I’d rather it be on my home turf.

So, that was that. A “fine-little-how-do-you-do”, or so the expression goes. I guess they’re a real thing after all. A truly baffling practice, but not all that unpleasant, I suppose.

Still, I had another (apparently inferior) plum tart to eat and a whole day to kill. Lacking any real direction, I decided to take a seat on a bench. So, I sat, and ate, and pony-watched, which is a polite way of saying I eavesdropped on passers-by.

That turned out to be sort of a mistake; lots of ponies were talking about me. I’d almost forgotten the effect my presence has, even after all this time.

“Oh my, is that him?”

“Oh my gosh, don’t look now, but that’s…”

“Look, it’s that stallion, the one who lives on the edge of Everfree.”

“What is he doing? Is he meeting somepony?”

“I thought his business was supposed to stay outside the town.”

“Hey, did you hear Silverspeed got chewed out by Rainbow Dash?”

‘Hang on, that one’s not about me.’ My ears perked at the mention of Rainbow Dash’s name. My little rendezvous with her had left me pretty eager to see more of that mare, and information about a potential client is never unwanted. I turned my ears to the two mares gossiping across the street. Sisters, by the look of them. Nopony I knew.

“No. What happened?” said the one with the bow.

“She skipped out on snow duty. Whitetail Woods is totally bare,” replied the one with gelled spikes.

“Shut up! She just bailed on it?”

“I dunno, but RD gave her a tongue lashing.”

“Yeah, her and every stallion in town.” The two shared a laugh at Rainbow’s expense. “But no, for real, Whitetail Woods just looks so gross right now. It’s all brown and junk.”

“I hope we don’t end up having to cover it. I hate snow duty.”

“Ugh, I know. Oh hey, speaking of snow, we should get over to Snowdrift’s. He said he wanted us to…”

The mares began to walk away, but I’d already stopped paying attention. Devious wheels were turning in my head, and I began to form a wicked smile. Apparently, lazy pegasus meant no snow. And no snow meant hiking.

I crammed what remained of my tart into my mouth and began walking. I could hardly wait. I had only just discovered my newfound hobby before the winter snowed over all my fun. I desperately needed to get a hike out of my system. The skip in my step carried me straight to the trail in Whitetail Woods. I’d been through there once or twice. It’s a nice flat walk, barely a hike, really, but still appreciated.

However, the lovely reds and oranges of my autumn walks were replaced with a dry brown palette of dead grass and skeletal trees. No birds sung, and no critters ran along the forest floor, they were either gone or asleep. The sun shone freely through the empty branches, covering the ground in the gnarly shadows of the trees’ dead limbs. The ground was dusty, mottled in patches of dying vegetation and loose twigs. It was like an old apartment building, unattended and unloved.

Still, a hike was a hike. And, truthfully, there was something eerily enchanting about the silent forest. If it weren’t in the daytime, it might’ve been jeans-shittingly spooky, but in the light of day, it was just sort of… bizarre. Everything was either gone south for winter or hibernating, so the only sounds were the shuffling of my hooves and the occasional snap of a twig. It didn’t take me long before I began to float into the usual trance of the hike.

It was a perfect little release. My muscles had been itching for a good long walk. I couldn’t help but grin as I made my way further and further into the forest. Nopony around. No eyes. No whispers. Not even the pitter-pat of animal feet. It was just the getaway I needed. I allowed my mind to wander.

‘This is lovely. I wonder what Derpy’s up to. Probably working. She works so hard. Maybe I should help her out financially, things have been good to me lately. No, that’s not my place. She’s not a charity case or anything. I should set up another date with her. I’m going to see her tomorrow, after all. Maybe we could go for a hike. Oh, wait, by then they’ll probably have snowed this back over. It’s a shame really.’

I kicked an errant stone from the path into a tree. It collided with a satisfying clack.

‘I wonder how far this is going to go. I mean, I really like this mare, but… Where does she see us in a year? In ten years? At one point she said she was trying to find a daddy for Dinky. Is that… is that me?’

I suddenly felt very nervous. My slow walk turned into a nervous trot.

‘Oh, my gosh. Am I actually going to be a father to Dinky? I’m an awful role model, it would be horribly inappropriate for me to teach her anything I know. I mean, imagine me…’

“Okay Dinky, remember. You wanna griiiiind your hips…”

“Now, a proper Mojito consists of…”

“… and always, always, always, agree on a safe word.”

‘Guh, I don’t even want to think about that. I’m sure I have some other pearls of wisdom to impart to a small child. Let me see… Oh! I’m pretty good at managing finances, I haven’t gone broke yet. I could teach her how to… hike?!’

“Okay now, you want to put one foot in front of the other. Continue ad infinitum.”

‘Okay, so there’s not much to teachon that front. What am I going to teach Dinky, I have to teach her something!’

I stopped mid-stride to take a breath.

‘Wait, who said I was becoming Dinky’s father out of nowhere?’

I silently cursed my nervous nature. I’d gone and started trying to find the solution to a problem that didn’t yet exist. I was such a ball of stress I was actually inventing things to panic about.

‘Okay, so my own personal insanities aside, there still are a lot of details to actually iron out. Are we… dating? Are we doing that? It’s been one date, does that count? Definitely something to ask. Should I charge her for sessions? I’ll… have to think on that. I’ll ask how she feels about it. Okay, this is great. Making progress. Let’s keep it up.’

A fork in the path. I went left, deeper into the woods, where the trees are thick and sturdy.

‘What else? Okay, my relationship with Dinky. I’m not gonna freak out, but what actually am I to her? I’m dating her mother, obviously, but… what does that mean? I imagine it entails little to no responsibility, but I can’t be sure. How often do Derpy and I see each other? Do we do dates during the week, or do we just have the sessions. I mean… of course we do more than that, right? Our relationship is changing. Wait, do I even call it that? What is it if it’s not a relationship? Okay, that’s a minor detail. Don’t sweat it.’

A clearing, a little sunlight plain in the midst of the woods. Perfect for a picnic; I’ll have to remember it for summer. I began to walk around the edge.

‘Okay, so, what else do I need to figure out? Do I call her Honey, or some shit? Do we have pet names now? What…’

I sighed as I realized what the big question really was. ‘What changes and what stays the same?’ That was the crux of my every worry.

I had exhausted my brain. My legs were tired, and I was sick of thinking. ‘I’ll figure all this out later.’

I decided to take a seat under a decently comfortable-looking tree. ‘Ten minutes, then I walk back.’ I took deep, calming breaths. Despite my slightly neurotic nature, it’s hard to worry about things when you’re out in the great outdoors. I laid into the rough bark and let my worries drift way for the time being. It was my own little paradise. I was almost hot in my coat, despite the season. The lack of snow had really let this place warm up.

‘This is perfect. I needed to get away. Away from Carrot Top and Applejack and even Derpy.’

I leaned my head back. The bark felt good against my scalp.

‘I can just put everything out of my mind for a bit.’

I stared into the cold grey sky above. I realize that’s a tad cliché, but it was a rather nice view. Like the forest below, it was just so perfectly still. It was nice, just a lovely, unmoving moment in time that was all mine.

And that’s when something landed on my head.

“Gah!” I shrieked, as my sight was suddenly stripped from me, and a cold, almost damp feeling splashed across my snout. A heavy blanket of some sort draped over me. I floundered, honestly. I’d been in such an awkward position that I flopped onto my chest trying to stand. I threw up panicked hooves in an attempt to free myself from some perceived threat, flailing ineffectually on the forest floor. Eventually I managed to release myself from my torment, as one of my erratic swipes removed the offending object.

It flopped pitifully onto the ground. ‘What the fuck is it? It felt like a wet towel.’ I moved to inspect the face-attacker. It was rather large and flat and… had a tail? ‘Is that what I think it is?’ Then it moved. It gave a single lazy flap of its fin. It was a mantle ray, a smaller one, only about four feet across. ‘Fuck me, it’s one of those rays. What is it doing out here?’ Another pathetic flap. It tried and failed to get off the ground. ‘Oh shit, is it just a baby?’ The ones I’d seen before had been positively massive, this was big, but not big big. I glanced into branches above me, looking for a… nest, or something. ‘It’s all alone? Where are the rest of them? There were a ton of those things.’ Derpy and I—and Carrot Top, I guess—had seen a thousand of those rays at Ghastly Gorge.

‘Should I…’ I stared for a moment at the pitiable thing. It was clearly not well. By all rights it should’ve been flying around in the air. ‘… help it?’ Was I really going to do this? Helping a poor little critter seemed like the right thing to do, but… was I really going to? ‘Okay, Guilty, if you do this it’s probably going to be a whole thing. Are you ready for that?’

I bit my lip. ‘I probably hurt it when I smacked it off my face, too.’ I groaned. That meant I was responsible.

I ponied up. “All right, little dude. It’s your lucky day. I feel sufficiently obligated to rescue you...” I took another look at the blanket of a creature. “… as soon as I figure out how to move you.” It wasn’t exactly going to fit into my saddle bag. ‘Okay, then, do I just…’ I reached over to grab it.

The ray flailed to the touch. I recoiled instinctively as the poor creature tried to flee. “Shit! Don’t freak out!” It scraped itself against the rough forest floor as it clumsily slithered away. “Ah, geez! Hold *unf* still!” I tripped over myself as I gave chase. “Yer scrapin’ yerself up, buddy!”

I caught the fleeing creature, doing my very best to be gentle. “Just… hold fuckin’ still!” I threw it onto my back, like a poncho, it was all I could think to do. “Stay put you fuckin’—” It threw itself off of me, landing heavily back on the ground. “Fuck, buddy, I’m just tryin’ to help.” Something occurred to me. ‘Maybe it doesn’t need help. Maybe it’s doing just fine.’ I shook the thought from my head. ‘No, it’s flailing helplessly. It’s just scared. I need to calm it down.’ I took a cautious step towards it. It didn’t seem to be watching me, but it was hard to tell with those eyes. Like big black pearls. “Don’t worry, guy, I’m just gonna put you on my back and take you to a vet,” I said in as calm a tone as I could manage. To be honest, I wasn’t even sure the thing had ears.

I inched closer, eventually daring to try and put a gentle hoof on it. It flinched, but didn’t flee. “Okay, I’m gonna help you. I’m just gonna hoist you up over my back, now.” It struggled, of course. I wrestled to get the thing onto my back, but it wouldn’t stay put. It kept sliding off one way or another.

Eventually, I had an idea that worked. I took of my coat and placed him directly on my back. Then, I quickly put my coat back on. It took a few tries, but eventually, I had the guy tied down. Thankfully, he didn’t struggle, once I had him. ‘Maybe he’s like a bird, cover his head, and he thinks it’s nighttime.’ Everything finally seemed to be working, except for one thing. He was freezing! ‘Oh, gross, he’s all cold and slimy!’ Okay, maybe he wasn’t slimy, but he kind of felt like it. His skin was like velvet, soft and supple. The real issue was how fucking cold he was. It was like filling my coat with snow.

Still, now I had the poor guy secured. I hurriedly marched into town with a giant fish in my coat. I may have been shivering the whole time, but I was being a good pony. I was earning positive Karma, which I would almost certainly piss away on booze and cereal for dinner.

As I returned, I began to realize that I didn’t know where to go. I didn’t know where to find a vet, or even a hospital.

Holy shit, I better figure out where a hospital is. That’s important info.

Anyways, I debated where exactly I would head. ‘To Derpy? She’d know where a vet is, right? Wait, she might not, she doesn’t have a pet or anything. Who has a pet?’ I pondered. ‘Twilight? Is Spike a pet? Wait, she said she was going to do some research on these things, right? Maybe she’d be the pony to go to, anyways.’ The town came into view. Twilight’s was close. ‘Okay, time to visit my favorite librarian.’

*Knock-knock*

Spike opened the door, again. His reptilian (are dragons reptiles?) eyes blinked at me. “Oh, hey again. Uh… you okay? You look like you’ve seen better days.”

“Hey, ki- Spike.” I struggled to catch my breath. “Twilight home?”

“Yeah, but she’s studying something upstairs. She didn’t want to be interrupted.” His eyes gave me a once-over. “Is it important?”

I tiredly nodded.

“Well, come in. I’ll get her down in a sec.” He seemed sympathetic, if nothing else. I’m getting a bit better at reading him, I think. I stepped inside, incredibly thankful for the existence of fire in the universe, as I gratefully eyed a fireplace across the room. The warmth in the air began to push the cold from the tips of my ears and hooves. The ray under my coat had kind of warmed up during the journey, but it still wasn’t exactly pleasant. The sooner I was free, the better.

I heard muffled footsteps and voices from upstairs. “Who is it, Spike?”

“I forget his name. It starts with a ‘G’ I think. He’s an earth pony.”

“Goldengrape?” guessed Twilight, as she came down the stairs.

“Guilty, actually,” I said coolly. I laid on a little charm. I just wanted to see her blush. “Sorry to show up like this.”

“M-mister Pleasure! Oh my goodness.” There it was. All the way up to the ears. Spike just looked confused at Twilight’s sudden lack of composure. “Y-y-you can come any time.” Mortified expression. “I mean… you can come over any time, not…” She bit her lip. I love how awkward she can be. “It’s a library!” she sputtered. “It’s open to the public, and—”

“Twilight, could you be flustered later? This is kind of urgent.”

She promptly silenced herself as I undid my coat.

Her eyes shot wide. “Oh my gosh! You’re bleeding!” she shouted.

I inspected myself, perplexed. Sure enough, blood was dripping out of my coat. Not mine, though. “Oh, hell.” I quickly threw the coat off, revealing the creature beneath.

Twilight’s eyes grew even wider. “Oh my gosh.”

“He was floundering around on the ground in Whitetail Woods, I think he’s sick.” I took another glance at it. There wasn’t a lot of blood trickling out from under the beast, but it sure was there. “I didn’t know he was bleeding.” I cursed myself for not noticing. I wouldn’t have wasted time teasing Twilight if I’d known.

Without a moment’s hesitation, Twilight was moving. “Spike! Go get Fluttershy!” He just stared at the tableau before him. If scales could pale, I imagine Spike’s would’ve. “Spike, now!”

He jumped at the shout, and quickly gathered himself. “I’m on it!” And with that, he grabbed himself a coat and rushed out the door, a determined look on his face.

Twilight’s horn began to glow, and suddenly shit was getting done. Somewhere a closet opened and a big tarp flew out, rolling itself out in front of the fireplace. A first aid kit soon followed, as well as several old-looking rags, which folded themselves across the tarp. The ray was lifted off my back in a tingly cloud of lavender energy and placed atop the makeshift doctor’s table.

All this happened in about five seconds, for the record.

I was impressed. “Wow, that was—”

“Quick,” she interrupted me. “There’s a shower through the kitchen. Go wash that blood off you.”

I checked my coat again, there were dozens of little red stains all along my back and barrel. “Oh, uh… right.” So, off I went, while Twilight tended to the Ray.

I took as hot of a shower as I could stand. I figured if there was even the slightest chance of him having some sort of infectious disease, I wanted to get as clean as possible. I scrubbed hard, and quick, along every inch of myself. It was strange, though, this wasn’t a shower shower. This was like… an emergency shower, a shower with real purpose. A fact made even more evident but the pinkish hue of the run-off. It sort of made me feel young again.

Covered in scrapes and dirt and tears, I would wash away whatever remained from my most recent beating. It seemed like the water was always a little pink back then.

I probably shouldn’t dwell on this.

When I returned to Twilight, she was busily casting some kind of spell on the creature. She didn’t seem to notice my return, as ribbons of light flowed from her horn into the ray. “What are you casting?” I asked.

Her eyes never left the creature. “A healing spell. His underside is covered in cuts and scrapes. I’m doing what I can to close the small ones.” Purple eyes darted over the ray, as tiny slits in the creature’s surfaces glowed with a white light, only to vanish.

“And the big ones?” I wasn’t actually sure I wanted to know.

“There’s one big one I think I’m going to gauze over,” she explained.

I stepped closer to her. She looked pretty intense. “Anything I can do to help?”

She swallowed. “There’s two books with information on Mantle Rays in the library. They’re in the biology section: Creatures and Features by Manic Monday, and The Complete Monster Manual by Natural Twenty. Get them for me.” Sweat was beginning to form on her brow.

I didn’t dawdle. Twilight had this authority about her that made me move quickly. The books were easy to find, if annoying to procure. Both of them were fat fucking tomes. When I returned, Twilight had finished channeling her sorcery and had applied a styptic along one fin. The manta still wasn’t really moving, but it wasn’t scraped up anymore. “Hey, he’s not bleeding,” I said gleefully. I was genuinely happy to see the thing getting better.

“Yeah, I closed all the little cuts; and the big one wasn’t too deep,” she explained. A glass of water floated to her lips and she took a sizable gulp. She was breathing heavily, and sweating more than before. Her brow was glistening. It was kind of sexy, honestly. “That spell’s not exactly easy, though.” She smiled at me with tired eyes. “Oh good, you got the books.”

“Oh, uh, yeah.” In my admiration of sexy-sweaty-Twilight, I’d actually forgotten about the giant books I was carrying. “Big enough for you?”

She giggled. “Yeah, they’re going to be really helpful once Fluttershy gets here.” Twilight took a seat next to the ray

“Fluttershy?”

Another gulp of water. “Oh, she’s a friend. She takes care of animals. She actually lives over by Everfree, like you.”

I knew the house she was talking about. It’s the only other house as far out of town as mine is. “Oh, okay.” I put down the books and sat beside her. The ray was beginning to show telltale signs of movement, a twitch of its long skinny tail, a shift of the fin. “It looks like whatever you did helped.”

She nodded exasperatedly. The spell had taken more out of her than she let on.

I suddenly felt guilty. I’d sort of barged into her home with a wounded critter, and expected her to help. “Sorry for all this, by the way.” I bit my lip a bit. “I didn’t mean to just drop this on you. I just… didn’t know where else to go.”

Twilight tucked her legs under herself. “You made the right call. The vets in town don’t know what to do with anything that isn’t a regular pet.” She stared into the crackling fire, and sighed heavily. “I had a hard time trying to get Spike treated a while ago.”

I scowled. “But still, I was just going ask you where a vet was or something. I didn’t mean for you to go to all this trouble.”

She shook her head. “It’s no trouble, I just—”

“Just exhausted yourself,” I insisted. “You didn’t have to do that.”

“Who else would’ve helped this poor guy?” She laid a hoof on the ray’s velvety skin. “I was glad to help. Especially since I’ve been trying to find one of these things since you told me about them.”

I felt my brow wrinkle. “You never found any? There were more of those things than I could count over at Ghastly Gorge.”

She shook her head. “I went there the day after you told me about them, but they were gone.”

“Huh, weird,” I remarked.

“It gets weirder,” Twilight explained. “I got in contact with a research station on Smoky Mountain. I was trying to find out if they had any research material on Mantle Rays in particular, nothing special. But when they wrote back, they said the rays disappeared from the mountain months ago. Since their disappearance , they’ve been spotted all over western Equestria.” Twilight looked around. “I have a map, somewhere, of all the sightings. It’s like a… mass exodus of some kind.”

“I take it that’s not normal.”

“Not as far as anypony knows. It might be something that comes once a generation or it might be something else entirely.” Her gaze fell back to the creature in question. “This guy might give us a little bit of insight.”

“Trippy,” was all I could really say. I needed to change the subject; I wasn’t really interested in the migration patterns of lava fish. “So, we’re just uh… waiting on this Fluttershy girl?”

“Mmhmm,” Twilight hummed. “I patched him up, but you’re right, there’s definitely something wrong with him. Fluttershy’s great with animals; I want her opinion before I do anything else.”

Another awkward silence. Part of me considered leaving. Twilight seemed to have a handle on the situation. She had an expert coming over, there wasn’t really anything left for me to do. I… I kind of wanted to stick around, though. I wanted to make sure that the mantle ray was going to be okay.

That said, I needed some kind of conversation to keep myself from getting awkwarded to death. “So, uh… how have you been, Twilight?”

Instant sulk. She smiled through it, but her brow betrayed her. “I’ve been good, you?”

“Twilight,” I intoned. “It’s me. Guilty. You don’t have to lie.”

There was the frown. She sighed, and buried her face in her hooves. “How do you do that?”

“Years of practice.” Compassionate smile. “Things not going so well with your guy?”

“Not mine anymore,” she said fighting a tear.

“You break it off?” I asked.

She just shook her head solemnly.

Calculated sigh. Pat on the shoulder. “That sucks.”

She chuckled darkly. “Yeah, it does.” She glanced back over to me. “How about you? Pinkie Pie said that you were out on a date with my mail mare.”

‘Uh-oh… Twilight knows Derpy. I hadn’t anticipated that. What do I say?’ I took a moment to curse small towns before responding. “K-kinda.” My face felt hot, and it wasn’t from the fire. “Sh-she needed some practice dating, was all. She’s a… friend, and I wanted to help.”

Twilight raised an eyebrow. “What’s got you all worked up then?” It was such an innocent question. She wasn’t trying to pry, she just… was.

‘Do I tell her? Is that okay to talk about? Is that just between me and Derpy?’ Twilight sensed my discomfort. I’m getting sloppy, I shouldn’t have had any tells. ‘Twilight and I seem to have developed an interesting relationship. We sort of seem to serve as confidants. Hmm… okay, let’s do this.’ “This is between us, right?”

“Oh, uh… of course.”

“I asked her… if she wanted to try again… for real… and she said yes.”

“Oh, my gosh! Congratualtions!”

“Yeah, no, it’s great. It’s just…”

“Scary?”

“Yes!” I shouted. I didn’t mean to shout, it was just… nice to have someone to talk to about this, someone who understood me, no less. “Sorry, I just—”

“Don’t worry, I understand.” Twilight chuckled. “And yeah, I had a few freak-outs early on.”

I nodded. “It just… feels like a lot of pressure.”

I felt a hoof on my shoulder. “It is, and it isn’t. Any pressure you’re feeling you’re manufacturing for yourself. It’s just anxiety getting to you.”

“Maybe so, but that doesn’t make it any less…”

“Suffocating?”

I shrugged. “It’s not that bad. It’s just…” I searched for a word. “… annoying. I’m not used to worrying about this… I have so many questions and no answers. I just…”

“Want to figure out exactly how it works? A relationship I mean.”

“…yeah…” It felt a little weird, getting advice from a girl so much younger than me. I must have five years on Twilight, at least. And yet, she has more experience than me in this area.

“Well… that part gets easier. You’ll fall into a rhythm.” She gave me a little shake. “Just think about it like this: whatever happens, it won’t kill you.”

I couldn’t help but smile. It was decent advice. “Thanks.”

“Well, what are friends for?” she asked innocently. ‘Friends, huh? When did I get so many of those?’

At this point the door burst open. “I brought Fluttershy!” Spike cried. A yellow mare stepped into Twilight’s home. I knew I had seen her before, but I couldn’t place her.

“Twilight, Spike said you had an injured manta ray?” she almost whispered. ‘Oh, now I recognize her. She was that mare with Rarity at the spa. Quiet as ever, it would seem.’

“Not exactly. It’s something a little more… exotic.” Twilight turned to me. “Do you mind giving Fluttershy and I some space? We’re gonna try to figure out what’s wrong with him.”

“Oh, uh… no problem.” ‘I guess I really don’t have much to contribute.’ “I think I’ll keep Spike company or something.”

My words were lost as Twilight and her friend went to work on the creature. ‘I’m not going to be much help anyways.’ Part of me considered going home again, but… I decided to stick it out. ‘Hell of a way to spend a day off, though.’ It really wasn’t how I had seen my evening turning out.

I flipped through some books and chatted with Spike. He talked about some comic books he’d been reading lately, but I wasn’t really paying attention. Nopony else really stopped by the library while it was being used as a makeshift veterinary clinic, which was good. It meant that no one got interrupted.

Eventually Twilight and Fluttershy had something of an answer. “We’re going to throw him into the fireplace,” Twilight explained calmly.

I blinked as I looked up from the cheesy horror novel I’d been forcing myself to read. “Fuckin’ seriously?”

Twilight’s glared at my use of fuck, and indicated Spike a short distance away. I guess the 16-year-old’s precious ears were too pure. I shouldn’t judge, I’m sure Spike is like a brother to her. Whatever the case, I was more concerned about throwing the beast into the fire.

“So, the fire’s going to make him… better?” I asked. That seemed to be what she was saying, but I wanted to be sure I wasn’t going crazy.

“I think I mentioned it once before. Mantle rays are magma divers. After a little research and… a little guess work, admittedly, we’ve come to the conclusion that he’s too cold. He’s got hypothermia.”

“So, we’re sure this is a good idea?”

Her ears went down. “Let’s say eighty percent sure.”

I stood up from the comfortable little corner I’d made for myself in the next room. “All right, I wanna be there for this.”

Twilight had pulled out some sort of little grill thing and placed it over the roaring flames. It looked like they had thrown a few logs onto the fire since I’d brought him in. We all watched as Twilight lifted up the monstrous thing and placed him onto the grill. I knew it was going to happen, but that didn’t stop the scene from being surreal as hell. He didn’t quite fit, actually. His back end drooped off the end of the grill thing, and Twilight had to force him in a little more. His face ended up scrunched against the back of the hearth. We all waited for something to happen. A minute passed. Then five. Then twenty. I was about to call it a day, I was tired, it was dark, and I wanted to get some rest before my appointment tomorrow.

And then it stirred. Fluttershy noticed it first, but it was beginning to wiggle the end of its fins. Its tail then began to twitch. A few moments later, the thing actually lifted itself off the grill, and floated out of the fireplace.

It was… serene. No one said a word as it soundlessly drifted upward toward the ceiling. It circled impossibly slowly through the air above our heads. When I’d seen them before they were all moving so quickly, but this one was so slow it seemed to defy all physics. It was like the air was water, and the ray was swimming along, ever-so gently.

Spike was the first to break our silence. “Woooooaaaaah…” A truer word was never spoken.

Several more minutes passed, as the four of us stared at its white underbelly. “What now?” I asked, remembering myself.

“Oh, um…” Fluttershy, forced herself to speak. “I-I’ll take him home. I’ll keep an eye on him and make sure that he makes a full recovery.”

“Oh, awesome,” I said with a foalish grin. This was turning out great. I’d rescued a thing! It may have just been some poor little creature I found by chance, but if it weren’t for me, it might’ve frozen to death. That felt…

… kind of awesome.

As I sat there, feeling good about myself, completely ignoring my surroundings, the ray saw fit to gracefully land on my back. I shrieked rather girlishly. I hadn’t been expecting it, but the ray was so warm this time. It wasn’t the cold, slimy thing it was on the trip over. It was a hot velvety sheet of warm goodness. It was almost weightless, too. It was kind of… I’m running out of words for weird.

Fluttershy giggled at my expense. “It looks like he likes you.”

I smiled a big shit-eating grin, the kind Crook would have. “Why shouldn’t he? I rescued his floaty butt.” I would’ve said “ass” if I didn’t think Twilight would glare at me again for it.

Fluttershy managed to coerce the ray off of me and tried to get it to follow her home. It didn’t seem too keen on the prospect of going outside into the snowy winter air, but eventually was made to go. It clung desperately to Fluttershy, though. The poor guy did not like the cold.

I took my leave, too. Actually, Fluttershy’s and my house were in the same direction, so when we headed out I got to know her a little.

“So… you take care of people’s pets?”

“Oh, um… yes…” She looked away, terribly nervous.

Dealing with shy people is really tricky. You can’t force a conversation, even though your instincts will tell you too. The real trick is to get them to start one.

“Hmph… it’s funny,” I said. This is a technique that’s served me well. If you say something to make the other pony curious, there’s a good chance they’ll have no choice but to ask about it. It’s not perfect, but it works a good amount of the time.

This time included. “Um… what’s funny?”

Friendly grin. “Nothing, just… it was sort of on a whim that I decided to take the ray to Twilight. It’s just funny that she knew the perfect pony for the job.”

She blushed. “Oh… I-I wouldn’t say I was perfect for the job. I’d never even seen a mantle ray before.”

“But you fixed what ailed him. He’s like a new ray.” Compliments are good, too. Sometimes a shy pony will try to play them down, but if you’re persistent, they’ll eventually accept it.

“Well, I was the one who figured out that he was too cold. But if Twilight wasn’t there, I wouldn’t have known he could be put in the fire like that.”

“Maybe. But, without you we wouldn’t have gotten even that far.”

“I guess so…” she whimpered. Poor girl, I was making her so uncomfortable. ‘Wait, is she friends with Applejack? Maybe she’s uncomfortable because she knows who I am.’ I snuck a glance at her. She was staring into the ground, avoiding eye-contact. ‘That might be it.’

“Um… d-do you remember when we met before?”

I raised an eyebrow. I was kind of surprised she remembered me. “Yeah. At the spa, right?” She was proving hard to read. Every signal she was sending was just “nervous.”

“Um… I didn’t know who you were, then. B-but… the spa twins told me about you.” Her blush was beginning to rival Twilight’s.

‘Iiiiinteresting. Where is this going?’ “You mean about my work?”

She nodded. “A-applejack told me about you, too. She talks about you. A-a lot, sometimes.”

Begrudging smile. “Does she, now?”

Another nod. “And I… wasn’t sure who to believe. B-but... after you saved this poor helpless critter… I think I can make my own decision.”

“I’ll… take that as a compliment.”

She swallowed. “I-it is… you’re a very kind pony.”

“Hey, thanks.” Now I was the one blushing. She was just so sincere about it, it was hard not to.

“S-so… um…” Her nerves skyrocketed. Her face was a tomato, her legs were shaking to the point where she almost stopped walking. I already knew what she was going to ask. “I-if… somepony wanted to… t-to… m-make an ap-p-p-p-p-pointment with you… h-how would they…” she trailed off, unable to fight her embarrassment any more.

“Well, most of the time they write a letter. Ask for a date and a time, and just show up.”

“B-but what if you already have an appointment?”

‘She’s thinking ahead.’ “I have a little ‘do not disturb’ sign. I don’t really have to use it very often, honestly. I usually only have three or four appointments a week.”

“Oh… okay...”

‘Why do you ask?’ I almost teased her. I thought better of it, though. It took a lot of courage for her to even ask me that, and I didn’t want to make her feel judged.

So, the two of us chatted a little more as we made our way outside town. She and the ray went her way, and I went mine. My house was freezing, when I got home, but hey… Winter.

I feel… really good about today. I… saved a life. That’s just kind of awesome. Fluttershy invited me to come over and check on the thing every now and then, which I may do. So yeah, even if today was… exhausting, I’m going to call it a plus.

Anyways, my house is nice and warm now, and I’m gonna head to bed.

Author's Note

Once again, thanks to my editing team, aquapunkchick, coandco, BlackSkulls, Jake the army guy, and newcomer Unimpressive Vagaries.

It's been a little while, but I finally pumped out a chapter. Guilty gets to be a good pony, and I get to write more Twilight (who is best pony). So I'm pleased with it.

So comment and fave and like and all that junk. I'll love you for it.

Couples

Chapter 20

Couples

The hiss of the showerhead rang in my ears. Once again, I sat beside Derpy as the water washed away our sweat and fatigue, cleansing us of our shared pleasure. The sex had been as enjoyable as it ever was. We’d done what we always do; we fucked like rabbits from the moment she walked in the door until we could no longer continue. It was great… honestly. It always is.

I was somehow… disappointed, though.

I guess… I was expecting it to be… different?

I ran a hoof over my face. ‘I’m such a colt, expecting everything to change just because I’m… seeing somepony… kind of.’

“What’s wrong, Guilty?” Derpy asked. I hadn’t been expecting her to say anything to me. She’s usually deep inside her head when we’re in the shower.

“Nothing,” I responded without thinking. “I was just...” I swallowed. “Why do you ask?”

She shrugged. “I dunno. You just looked kinda upset.” She placed a gentle hoof on my shoulder and leaned into me. “What’s up?”

I had been planning to try and clear some stuff up. I guessed this was as good a moment as any. I took a breath. “What…” I’d been planning on asking her about this for some time and I’d scripted dozens of potential scenarios. I had spent a good part of my morning cementing a casual, yet direct, means of addressing my concerns.

“What are we?” I asked, sounding more than a little panicked.

‘I astound myself.’

She cocked her head. “What do you mean?”

“Well I just…” I scrambled for words. “I don’t know what to tell people if they ask what's going on with us. Are we ‘dating’? Are we ‘seeing each other’? I just—” A warm nuzzle both calmed my nerves and silenced my rambling.

“Does it matter?” she asked.

She allowed the question to stew for a moment. I don’t know if she was waiting for a response, but I didn’t quite have one.

“We’re still figuring it out, I think. We haven’t even gone on a date yet. I mean, not a real one.” Her brow furrowed. “Why do you ask? Did somepony say something?”

I sighed. “No… well, yes… I ran into Lily. She was just curious, but I… I don’t know. I felt bad when I didn’t have an answer.”

She shrugged. “It’s okay.” She pressed herself firmly into me. Her body was so warm, even warmer than the water running down her skin. This was new. She never cuddles me in the shower. “Like I said, we’re still figuring it out.”

I didn’t let her see me frown. I appreciated her effort, but it didn’t make my life any easier. I wanted to know what we were. If I knew what we were I’d have a better idea of what steps to take. I needed a role.

“What are you doing on Wednesday night?” she asked without warning.

“Oh, uh…” I checked my mental calendar: no appointments. “Nothing, I think. Why? Have something in mind?”

“No, nothing in particular, just… I want to see you. We should do something.” Her delivery was forced. In that moment I realized that she must’ve been feeling a little awkward about this too.

When she said that, though, it… it felt amazing. My frown vanished, and I couldn’t have stopped smiling if I wanted to. “Yeah, um… you could come over,” I offered. “I could cook dinner or… we could go out again or…”

“Your place sounds good. You wouldn’t mind?” She smiled.

“No, that…” I could feel my grin growing. “That sounds really nice.”

“Great.” Suddenly she took her weight off of me and opened the shower door. “Come on, Guilty. I brought corn muffins today.”

I almost tripped over myself while getting out of the shower. Derpy’s corn muffins are amazing.

So we got dried off and I prepared the tea. There were no words as small yellow food-stuffs were consumed with prejudice. Moist as ever. Strong in flavor. Laden with delicious butter. The world melted away into a muffiny haze, as explosive flavor overwhelmed my senses. I was lost… lost in an endless sky of pastry. Fields of golden corn lay before me as I flew through the buttery sky.

Muffins… what would the world be without them?

Derpy’s voice plucked me from my flavor-induced daydream. We hadn't spoken since muffins were mentioned. “These came out pretty good, huh?”

I swallowed my last bite, sad to see it go. “They always do.” I wiped the crumbs from my face. “Your muffins are fit for royalty, Derpy.”

She rolled her eyes at my flattery. “They’re just muffins, Guilty.”

‘Sacrilege!’

“So anyways…” Derpy wiped crumbs from her mouth. “How is everything, Guilty? Applejack hasn’t given you any trouble lately, has she?” Such concern.

“No, I haven’t seen her since that day.” I groaned aloud. “I’m not going to enjoy that inevitable encounter.”

“Aw… I’m sure it’ll be okay.”

I shot her a look. “Really?”

She shrugged sheepishly and her ears drooped. “Maybe…”

“Meh, it doesn’t matter.” I could feel myself beginning to sulk.

‘Change the subject.’

“How are the girls? Ms. Harvest and them, I mean.”

Derpy perked up. “Everypony’s doing good. Lily’s sister’s birthday was the other day. We had a party. Lyra got drunk. It was silly.”

‘Sounds like Lyra.’

“So, you guys had fun?”

“Yeah, it was nice.” She rested her head in her hooves.

I grinned, as ponies often do during pleasant conversation. I was enjoying our little chatter over muffins. It was exactly like it had always been. Which is likely why a slightly uncomfortable thought occurred to me once again.

‘Should things be different now?’

It weighed on my mind, evidently. Our relationship was changing. Wasn't everything else supposed to change with it? I decided that this wasn't the best time to fret, however, and I continued enjoying her company. I guess I've just… got a lot of stress in regards to this whole thing. Twilight and I talked about it, but… it’s still kinda… scary. I’m just in uncharted territory and in desperate need of a map.

I came back to reality, realizing it was my turn to speak again. “So how’s Dinky? School going okay?”

She nodded. “Yeah. She’s doing really well. She hasn't gotten into any more fights, either.” She took a deep breath. “It’s been nice. One less thing to worry over.”

'I could use one less thing to worry over right now.' “That’s good.”

And then, the conversation stopped. Nothing had happened, for the record. We weren’t interrupted and it wasn’t some awkward silence. We were just sort of... smiling at each other. I caught myself staring but… I didn’t stop. I allowed myself to stare at her, to take in every detail I could. The shape of her chin, the crook of her eyes, the way her mane moved just so. She did the same. I followed her gaze as best I could: my eyes, my shoulders, my jawline, I think. She was just as eager to drink in my features as I was hers.

I changed my mind. Things were definitely a little different.

“So I should probably get going.”

“Tragedy.”

She giggled. “You’re so silly, Guilty.”

“Well, it’s just that the rest of my day is downhill from here.”

She rolled her eyes and laughed. “You’re such a dork sometimes.”

“Well aren't you rude,” I teased.

“Not listening!” she joked. “Anyways, I stayed a little late today so I’ll pay for the third hour.”

‘Has it really been that long?’ I checked the clock. ‘Ten past one, I’ll be damned. Sessions with Derpy fly by faster than ever these days.’

I cleared my throat. “Don’t sweat the extra hour, Derpy. It’s not a big deal.”

“No, you’ve got your rule. I’ll pay for it,” she insisted.

“Derpy, I’m serious. You don’t need to pay for three hours. I probably shouldn’t even be charging you for any.” I hadn’t meant to say that. It just sort of came out.

Derpy cocked her head. “Why?”

“Well because… you know.” I waited for her to catch on. She didn’t. “Because of… us.”

She shook her head, determined. “Mm-mmm. No way. I’m not going to stop paying for sessions, Guilty. I pay Goldy for carrots. I pay Bon Bon for candy. And I’m going to pay Guilty for sex...” She gathered up her basket and saddlebags. “…on Sundays.”

She smirked, and her meaning became clear.

I smirked back.

She removed three hours’ worth of bits from her bags and made for the door. She was paying for that hour regardless of my opinion. “So… Wednesday?”

I nodded. “Wednesday. Seven?”

She nodded back. “Seven.”

“Bye, Derpy.”

“Bye, Guilty.”

Exit.

Twenty paces.

Turn.

Wave.

Leave.

With a click, the latch on my door snapped into place, and once again I had my house to myself. With more than twenty four hours till my next appointment, I wasn’t exactly sure what to do with my time. ‘I’m just sort of living from one Derpy encounter to another. Aren’t I?’

I rubbed tiredness from my eyes. I was already dreading the inevitable emptiness of my evening.

So, I tidied. Sheets. Dishes. I reorganized my music collection. Threw out some old magazines. After that, I just sort of… waited. Okay, that’s not entirely true.

I masturbated… a couple times.

Probably not the smartest thing to do, given the circumstances. I was going to need full testes tomorrow. Still, I kept thinking about that dream I had, the one with Derpy in the stable. It’s been making for good masturbation fodder lately. It was such a warm dream. I sort of keep hoping I have it again.

Sadly, I didn't.

The next morning I journeyed into town again. After all, I’d just agreed to cook dinner for Derpy, I was going to need something to cook. I’d been thinking about stir-fry, but that idea died once I got into town. There was no market that day; the weather had gotten cold enough to keep most sane ponies indoors. As such, I’d have to see what was available at the local grocery store.

I made it to Barnyard Bargains without incident. No unfortunate encounters, no glares, not even so much as a whisper behind my back. I’d even remembered how cold it got inside, and packed an extra coat accordingly. Things were going well. I meandered a bit, hoping to be inspired by the selection.

Bags of frozen veggies, instant noodles of all kinds, less than appetizing “fresh” produce, it wasn’t much to work with.

‘There’s pasta. No, not feeling it. Brownie mix? Nah, I don’t think I want to make dessert. Ugh, that bread looks as stale as anything.' The crusty little loaves caught my attention. Wait a second… ‘

I got a wicked idea. Stale bread, frozen vegetables, they had eggs, too. I have everything I needed to make a nice veggieloaf.

‘What do I need... onion, celery, some ketchup? I have milk at home, and plenty of spices. I need a good base, though… Oh, they have oats, perfect. Yeah, I’m doing this.’

I gathered up everything I needed. I hadn’t made veggieloaf in quite some time, not since I moved to Ponyville. Crook always loved my veggieloaf, I used to make it for him pretty often. Cooking lessons were part of my escort training, and I always enjoyed them. This was probably because I got to eat something after every lesson. It wasn’t always good, but an extra meal was an extra meal.

‘What else, though? I need a side dish or two. Potatoes of some kind wouldn’t be bad. Maybe in a salad? I think I saw some decent looking spuds back over fuck my life, Applejack!’

She noticed me only a fraction of a second before I saw her. She had stopped mid reach, her hoof wrapping around a large bag of brown sugar. I was equally frozen, still just holding my cart of vegetables.

I waited for the inevitable. The encounter I’d been dreading was coming to pass. Here she was, my tormentor, no Derpy to defend me, no Crook to protect me, just Applejack. I swallowed as her eyebrows slowly turned down. Her lips twisted into a frown. This was it, this was my comeuppance.

And then she walked away. She grabbed her sugar, tossed it over her back, and walked straight past me.

I was dumbfounded. This was Applejack. The Applejack. She never needed a reason to hassle me, and today she had a good one. But here she was, pretending nothing had ever happened.

My next move was, admittedly, stupid. In my disbelief I swung around to confirm she was, in fact, just going to walk on by. “Is that it?” I blurted.

On she walked. Clearly choosing not to hear me. Stunned, I watched her trot off, and ultimately disappear around a corner.

“Okay then,” I said to no one in particular. I turned back around and grabbed my cart. It still took me a few moments to get my bearings. Once I convinced myself that that had actually just happened I continued with my chores.

Eventually I had my whole meal planned. Veggieloaf, mashed potatoes, and some asparagus. I also grabbed a bottle of cheap wine, and some more of that brown ale for myself. Once again, my submissive client rang me up. She managed to do so without an embarrassing faux pas, this time.

I took my leave, still trying to comprehend Applejack’s actions. ‘Am I… being ignored?’ I considered that maybe this was all some elaborate ruse. She was lulling me into a false sense of security. That theory didn’t hold a lot of water, though. Applejack wasn’t a schemer, she was a confronter. She wasn’t a delicate tool, she was a sledgehammer. A Crook, not a Guilty.

I think it’s the next evolution of her harassment: the cold shoulder. She’s going to act like I don’t exist to my face. Shunning, I think it’s called. Truthfully, I’m perfectly fine with that; I don’t need any interaction from her. I’m used to being ignored, being just a face in the crowd. In her mind it must be more of an insult, but to me it’s just about the most I could’ve asked for.

I got home swiftly; the weather looked like it was taking a turn. I hadn’t checked the weather schedule that morning, but It looked like there was going to be snow today. Once I got my groceries away, I began to… steel myself for upcoming appointment.

I had taken an appointment that… well… I wouldn’t normally take.

So, I got a reference from a client of mine, Berry. She’s a drinker. Luckily she brings her own wine, so I’m never paying for it, but that’s neither here nor there. Apparently a friend of hers owns a bar, and was looking for a good time with me. I was more than happy than happy to oblige. From Berry’s Description she seemed like a fun client. I was eager as ever get a new client until…

… Berry mentioned the husband.

Now, I’m no stranger to a Devil’s Threesome. I just… wasn’t sure I wanted to take a male client. Still, I humored her. I asked some questions. I acted like I was a little bit interested. They sounded like a nice enough couple: Earth Pony mare, Unicorn stallion, business owners. They moved here from some town called Caerfilly. In the end, I told Berry that my schedule was pretty full. She understood, and took her leave.

A few months later, Berry brought it up again in, wondering if my schedule was free. Once again, I managed to get myself out of it fairly easily.

Now, however, I was intrigued. Call it idle curiosity, but I decided to pay the two of them a visit.

The Ebol Bychan is a pub in town. I’d never been, but apparently it was owned by the couple in question. Truthfully it was a great little place. It had a nice stock, and looked like a lovely little pub. It wasn’t crowded, but hey, it was the middle of the day: just myself, a few regulars, and the mare behind the bar.

And what a mare she was. She was easily Quake’s height, though not quite as stocky. A slate grey coat. A navy blue mane. She was a massive sexy beast. The lovely lady made conversation with regulars in a thick Trottingham accent, pouring drinks and cracking jokes. I’ll admit it; I wanted her as a client.

I lurked in the background for a while, observing. Keeping to yourself is perfectly acceptable in a bar or pub, and no one made a point of pestering me. Nopony had really recognized me yet. I was just another weary patron, drinking away his time. I waited, hoping to catch a glimpse of the mare’s lesser half.

And lesser, he surely was. He stepped in the front door and promptly made his way behind the bar, standing a full head below his beloved. “Hello, wife,” he said. His voice was high and joyous.

“There you are.” She gave him a quick peck on the forehead. “Take over, I need teh set for a spell.”

“Yes love,” he replied, perhaps a tad whipped.

He was a yellow fellow. (Heh heh.) A dirty blonde mane with a little goatee and a bit on the thin side, he deftly filled the role that his wife was playing. A friendly smile, a jovial attitude, he was very… non-threatening. I suppose that’s why I was here, really. I was trying to… make myself okay with this.

I mean… I don’t want to turn down a client just because a stallion will be there, I just… I don’t know.

I mean… I do know. I’m not gay, or even bi. That’s what it really comes down to. I just don’t… enjoy being with stallions. It isn’tpleasant to me. When I was working the stable it was kind of like… eating your vegetables. Sure, it wasn’t fun, but it was necessary.

Now, though, it isn’t. I don’t have to take male clients. I don’t have to pretend I enjoy it. I don’t have to buckle down and take jobs that I don’t want to take. I’m in charge now, and I don’t have to do that. I don’t want to do that.

Lost in my head, I failed to notice that I’d made eye contact with the object of my worry. He smiled and waved, unaware of the alarms ringing in my head.

‘What have you done, Guilty? What have you done?! He’s walking over here! Quick, prepare an act!’ I had to think fast. No time to create a character, I would just have to keep my identity vague. ‘Be surly, be reserved, you’re his customer, you make the rules.’

“I ‘Aven’t seen ‘ou round ‘ere before.” I hadn’t noticed from afar, but his accent was hard to pin down. Almost like Trottingham, but… off.

I bowed my head and sighed heavily. “Just… looking for a quiet corner to drink.” ‘Appear annoyed, best thing you can do to make him leave.’

“Well, let me get ch’ou another one, yeh?” ‘Thick bastard.’

“You’ve got other customers. Get them a drink.” ‘Okay Guilty, don’t take it too far, you want to be forgotten. Be dismissive, not rude.’

“Well, I juss filled up Rusty, and I’ve got ‘alf a mind to cut off the Colonel. Juss leaves you.” He smiled. It was a genuine smile, no ill intent. He hadn’t been fazed by my overt lack of manners. I inspected my glass, it was getting pretty empty.

I acquiesced. I slid my mug to him. His magic lifted it off the table, and he made for the bar. ‘Now hang on, Guilty. Let’s not let this opportunity pass by. This stallion is your present obstacle. Get a feel for him, try and figure out what kind of pony he is. The more you know, the less you have to fear.’

When the Barkeep returned, I put on an apologetic mask. He my placed my beer back in front of me. “Thanks, um…” Scratch at back of head. “Sorry for being short with you. Just… having a rough day.”

He frowned. “Iss barely noon. Far too airly to be ‘avin’ a bad day.” His accent was so thick, it was almost hard to follow. I’ve known foreigners who spoke clearer Equestrian.

‘Keep things vague. Don’t commit to a story when you don’t have to.’ “Yeah, well…” I trailed off and took a sip of my beer. “… shit happens.”

“Sorry to hear. ‘Ou want somethin’ a little stronger?” he offered.

I just shook my head.

“You shoe-er?” It took me several seconds to figure out that he was asking if I was sure.

“Yeah, I’m fine.” I thrust an open hoof to the stallion. “Pumpkin Bread,” I stated, my default pseudonym.

He took my hoof and shook it hard as he could… which honestly wasn’t very hard. “Dai Thunderhoof, that’s D-A-I.” he offered back. “But I mostly go by Greenhoof.”

My brow furrowed a bit. “I can see why. That’s an interesting name.” He grabbed the back of the chair opposite me, waiting for my approval. I nodded, and he sat.

“Yeh, well… It’s not Equestrian.” He said no more on the subject.

‘Have I touched a nerve? Change the subject.’ “Why Greenhoof, though? I mean you’re… so very yellow,” I laughed a little.

“Yes, well… comes with the territory, I suppose.”

“As a barkeep?” I asked.

“As a gardener,” he replied. “I grow the veggies and such for the food on the menu. What about ch’ourself.”

“Baker.” The response was automatic. Pumpkin Bread is an old character of mine. I know his history front and back.

“Oh, thass gotta be tough, bein’ in the same town as Sugarcube Corner.”

I found a quick response. “Well, that place is more about pastries. I mostly do breads.”

“Oh, well thass nice. Everypony needs bread.” His face was plastered with a big friendly smile.

“That they do.” ‘Okay Guilty, start probing. What kind of pony is he?’ I pondered my first maneuver. ‘A jealousy test,’ I decided.

See, sometimes in my line of work, a couple will come in to see me, it’s far from unheard of. However, once we’re in the act, the guy might decide that he’s not okay with the whole “threesome” thing. Ofttimes the stallion will just explain that he’s uncomfortable, and everything comes to a close. Other times however, these stallions can get… confrontational. It’s no fun having a livid boyfriend literally pry you off of his significant other.

“So working here must be nice, huh? Get to stare at that big grey ass all day, right?” Chuckle luridly. “I would not mind a piece of her pie.” Sleazy smile.

His reaction was not to be expected; he grinned. “Yeah? I’ll let her know you said so.”

For a moment I doubted myself. ‘Do I have the wrong stallion?’ No, he fit Berry’s description to a T. ‘This is his wife I’m talking about, and he didn’t even blink at that. He all but offered her up on a platter. His face betrayed no ill intent, or anything disingenuous. He meant what he said, at least.’ Remembering myself, I responded. “Thanks.” ‘Okay, I am intrigued.’

“So, no girlfriend, I take it?” he asked. He was on the offensive.

“I’ve… got a girl… kind of.” I am hating this question more and more.

His grin grew wider. “And here ‘ou are, talkin’ aboat the barmaid. Naughty Naughty.”

I grinned back. “Just about as naughty as the stallion who just agreed to help me court his wife.”

His gaze narrowed. “How’d ‘ou know she was my wife?”

I couldn’t help but roll my eyes. “Well, you did call her ‘wife’ when you walked in. Kind of a giveaway.”

“Oh, I suppose I did. Wait, ‘ang on. That means ‘ou knew she was my wife when you were hittin’ on her.”

“I suppose I did.” I took a long sip of beer, waiting for some reaction from him. None came. “You really don’t mind if I fuck your wife?”

“No,” he said simply. Not a lie. No hesitation. He was even a little bit excited at the prospect. ‘Okay, he passes the jealousy test. What’s your next move?’

I cradled my chin in my hooves, trying my hardest not to stare. ‘Does he have a temper?’ A risky strategy occurred to me. ‘Okay, you can do this, but it’s not going to be fun.’

I curled my lips into a sadistic smile and prepared myself for an unpleasant act. “Well, that makes sense I guess.”

His brow furrowed. He’d been trying to get a reaction out of me, and I hadn’t given one. “Oh yeah? How’sat?”

I tried not to wince at the foul flavor of my words. “Well she’s like a nine, and you’re like a… six. You’ve got some kind of arrangement, right? Just the price of dating above yourself, I guess.”

His eyes bulged. He could not believe his ears, just as intended. How somepony reacts an insult is very telling. The thing is, some ponies will just take the high road if they feel themselves being called out. Disguise an insult as something else, and you tend to get a better read on them.

“Wow,” was all he could muster. ‘Scan his features for signs of anger. They can be subtle, but you’re good at this. This is what your special talent was made for.’ A slight tensing of the jaw muscles, he was angry, but not immensely so. His brow seemed normal, nothing going on there. His eyes… they were just shocked, couldn’t do much with that. I waited for the anger to build, searched for some buildup of emotion in his body.

And then nothing happened. The tensing in his jaw relaxed, his eyes returned to normal, and his lips even returned to a smile. “Enjoy your drink,” was all he said as he removed himself from his seat. It was a perfectly mature reaction, choosing to ignore somepony so venomous. He didn’t even get all that mad at me, just decided I wasn’t worth talking to.

In that moment I decided I’d learned all I needed to. “What’s a good day for you?” I called after him.

He turned around, uncomprehending. “Sorry, wot?”

I smiled. “I figure a weekday would be best. The bar’s probably busy at night, so during the day would be best, right? How’s Tuesday for you?”

The poor stallion was desperately trying to catch up. “What are you on about?”

I grinned and motioned for him to sit again. I love when I get to do this. “Allow me to explain. My name is not, in fact, Pumpkin Bread. My name is Guilty Pleasure and I am, to be blunt, the town whore.”

Once again, the poor stallion could not believe his ears. Before he could inquire further I continued. “I came here today to determine whether or not I would take you on as clients. In light of your mature reaction to my brazen behavior and your genuine willingness to share your wife with another stallion, I have decided that a session with the three of us would be perfectly acceptable.”

He opened his mouth to interject but I pressed on, smirking all the while.

“See normally, I don’t take stallions on as clients, not even ones with lovely wives. I had to make sure that you weren’t a short tempered, jealous husband who might ruin an otherwise lovely session. Since I’ve determined that you’re a decent fellow, I’ll ask again: Are you free Tuesday afternoon?”

The poor stallion looked dumbstruck. “Wot… juss ‘appened?”

A few minutes later I was sitting down with the couple, ironing out a time and a session. Coaldust, the wife, seemed pleased with the situation. Apparently she’d practically given up on becoming a client. I was happy to defy her expectations.

Tuesday morning, there was a heavy knock at my door. They were three minutes late. We’d spent a good amount of time discussing what a session would entail, and I had a decent script for the whole evening. Still, things rarely go according to plan, so I was prepared for anything.

‘Alright, Guilty. Music on, kettle boiling, bedroom arranged, conversation prepared. You are ready for this.’ I reach for the doorknob, only slightly hesitating. “Coaldust, Greenhoof, come on in.”

Their eyes were already scanning my home. “This is a lovely place ‘ou’ve got here,” spoke the giantess. I exaggerate, but she’s pretty fucking huge. For the record, that’s a plus in my book. Big mares have big assets.

“Well, thank you. Let me take your coats, have a seat.” The eager couple obliged, and the two of them sat at my table. There was an excited energy about them. The two of them were clearly ready and raring to go. However, I didn’t want this session to come to a climax too quickly. I had to cool them off before I could heat things up.

I joined them at the table. “So, I have the kettle on. Let’s just wait for that tea.”

The two of them were almost panting. “Sorry if we’re a little… worked up. This is all juss ‘appening so fast,” said Greenhoof.

“I’ll say. It ‘asn’t even been a day.” Coaldust’s voice was low, almost husky. “I juss mentioned it teh Berry off hoof, and then the next day me husband tells me that the Escort’s come to see us. And now, ‘ere we are!”

Amused chuckle. “Oh please, it’s hardly the royal palace.” Cradle chin in hooves. “It does serve its purpose, though.” Warm smile. Deliberate stare. “It’s just a little… business-cum-residence. There seems to be a lot of those in Ponyville.”

And just like that, conversation had begun. “The Bychan’s the same. Downstairs is the pub, and upstairs is home,” spoke Greenhoof.

“So how long have you lived there?” Friendly smile. These two were clearly not Ponyville natives. Any tiny sliver of something in common is grounds for bonding.

“Oh, we both moved ‘ere from Caerfilly some five years ago,” said Coaldust.

“Yeah? Friends in town, or…?”

“Family for me,” answered Greenhoof. “A relative owned a farm in town. That farm is now the Bychan.”

“Mmhmm. When I met him, I helped him fix it up,” explained the mare.

“Oh, so you two met here?”

Coaldust nodded. “When I’d heard the new pony in town was from Caerfilly, I had to meet him. Turned out to be the best day of my life. Months later we were married with a pub.”

Cute story. “Well, it’s a lovely little place,” I complimented.

Coaldust smiled proudly. “Thank you, I designed it meself. Built it, too.”

Impressed expression. “Well, you’re quite the architect.”

“Aye, that she is.” The couple shared a look. It one of those… weirdly alienating looks, like Lyra and Bon Bon shared. I felt like I was intruding on their moment. I wanted to say something and move the conversation forward, but it seemed like I would’ve been interrupting.

Thankfully, I was rescued by a whistling kettle. “I’ll just get that.” ‘Okay Guilty, let’s see what the lovely couple has to say when you’re out of the room.’ As I made my way to the kitchen, I kept an ear pointed toward my clients.

“So… excited?” asked Greenhoof.

“O’ course, I am. Are you?”

“O’ course. Been a while since we got you in bed with another stallion.”

‘Well, they’re no strangers to guests in the bedroom. That’s a good sign.’

“Far too long, if you ask me,” teased the wife.

“Careful now, I may juss get jealous,” joked the husband. The two of them chuckled.

There was a moment of silence as I turned the stove off.

The stallion broke the silence. “So, what do you think of him?”

‘Oh hey, they’re talking about me.’

“He’s very handsome. Reminds me o’ you.”

He laughed. “I’m serious.”

“I’m bein’ serious. He’s small for an earth pony. Reminds me of my frail little unicorn husband,” she teased again.

“Alright, alright. That’s enough o’ that.”

‘It’s been long enough. Time to return.’

I entered the living room once more, placing my tea tray onto the table. “I prepared some lovely green tea. I hope that’s okay.” I took my seat again. “We’ll just give it a bit.” I started a mental countdown for two and a half minutes. “So, Caerfilly’s near Trottingham, right? How’s the tea there?” Trottingham ponies can always talk about tea.

“Oh, we get great tea back home,” explained Greenhoof. He went on to explain about teas, and then the conversation just began to flow. We talked about tea, then liquor, then their pub. At one point we even started talking about where we grew up.

As our chat proceeded, I began to… notice something. The way the two of them carried on was… intriguing. They talked and spoke and behaved in a way that, at times, made them appear as a single being. They would tell a story and each one would know just where to pick up when the other left off. They would even speak in unison at times. They were so familiar with each other that they could… function for each other.

It’s not as though they were of one mind, though. They were just… so intimately familiar that they could anticipate one another’s actions with impeccable accuracy. ‘Is this what being a couple is like? The only pony in the world I’m that familiar with is Crook, and he’s basically a brother. Is it like gaining a sibling? That can’t possibly be right.’

After our tea was finished and our small talk began to lull, I decided to ask my all important question. “So, what exactly can I do for you today?”

The two of them perked up. It seemed they’d almost forgotten about the crux of the visit. “Well…” Coaldust began. “… I just wanted to put on a show for my naughty little husband.”

“Oh so I’m the naughty one?” asked Greenhoof in mock anger.

She tapped him on the nose. “Yes.”

He rolled his eyes.

“Sounds like fun,” I responded. Rising, I turned to the bedroom. “Shall we?

Truthfully, that made me feel a little better. If Greenhoof was just going to watch, I wouldn’t feel too put off. Then again, nothing was exactly set in stone. If Greenhoof wanted to join in at some point… things were going to get complicated.

We entered the bedroom, which I had rearranged slightly. I’d anticipated Coaldust’s request for a show and brought an extra floor cushion for the husband.

“So, a couple rules before we begin,” I said as I downed my potion. Receiving no reply, I continued. “If at any point anyone, myself included, says stop, everything stops. No exceptions.” I may have hammered that rule a tad harder than normal. “Second, no kissing on the lips. Well… you two can, just not with me, I mean.”

“Sounds good,” said the mare. Excitement was apparent in her voice.

And with that, I dove into my act. Sexy smile. Seductive Tenor. “Excellent.” Slow purposeful removal of jeans. “Let’s begin.” I offered her a hoof, which she took, and I led her to the bed. Without instruction Greenhoof found the cushion and took a seat. A little planning goes a long way.

Practiced hooves guided the large lady onto her back. She yelped as I placed myself on top of her. “I’ve been looking forward to this,” I admitted.

“You’re not the only one,” she said with a hungry grin.

I traced a hoof along her side, eliciting a small gasp and a blush. I worked my way down, kissing her neck and barrel, running my hooves along her hips and legs. She twitched and moaned in delight as I worked my magic. My lips came closer and closer to where she needed the most attention. I could feel her need. Her muscles tensed as I teased her, approaching her lips with painstaking patience. She was in no mood. “Juss’ do it fer fuck’s sake!” she begged, equal parts desperation and annoyance.

Not wet yet, but we’d moved pretty quickly. I remedied that. “Oooooooooh, yes yes yes yes yes,” she crooned as my tongue began to travel along her marehood. “Oh my goodness, yes.” There’s something about dark coats that makes a mare’s lips seem so much more pink. Her little slit peeked proudly through the fuzz.

As her pleasure began to build, so did her movements. I dove deep, clinging to her thick corded haunches as her hips began to gyrate.

Not an uncommon reaction to head, but a troublesome one. You just have to stick to your guns and follow the pussy where it goes.

Her flavor began emerge, and I eagerly licked it up. By now her lips were blushing and soaked. Wet flesh. Mingling fluids. Pumping hormones. This is my happy place.

Quite suddenly my happy place got… smaller. My world shrank as Coaldust’s hind legs wrapped themselves around my skull. “Oh my goodness don’t stop.”

‘I wasn’t planning on it.’ A little cramped, but not uncomfortably so. My muzzle was forced firmly into her lips, and my tongue began to explore deeper into her entrance. I let her scent wash over me as she inched closer and closer to climax. ‘Any minute now…’

Moments later she cried out. “Oh my goodness, I’m gonna come. I’m gonna come!” She gasped deeply as I pushed her over the peak into orgasm. In that moment, my world shrank again. Her legs squeezed hard on my head. ‘Holy shit, she’s strong. That is pain.’

I tapped furiously at any part of her, cries muffled by her flesh. “Oh gosh. Sorry.” Her legs spread wide, and I was set free. “I didn’t hurt you did I?”

‘Yeah, kinda.’ “Not at all, Just got a little cramped down there.”

“Don’t kill ‘im, it was just getting good,” teased the husband. I’d almost forgotten he was there.

“Hey now,” warned the wife.

The husband just chuckled. “How was he?” he asked.

She just let out a low whistle in response. She ran her hooves through her sweaty mane and turned her attention back to me. “My turn!” she declared with a devilish grin.

Before I realized it I was on my back, my hooves pinned at my sides. Her weight was impressive. She licked her lips as her eyes traveled over my body, feasting on the sight of me. Ever downward her gaze fell, until it reached its inevitable destination. She chuckled.

That never feels very good, but it does happen.

“He’s your size,” she said to Dai. A large smile began to emerge on her face.

“Yeah?” he asked, amused.

“Yeah.” The weight on top of me was removed as she slid her body down to nuzzle my erection. She placed a small peck on my shaft as a hoof brushed gently against my testes. I was surprised at how gentle she could be. “It’s wonderful,” she said.

Okay, that felt good.

Without pause, she wrapped her lips around me. Her gentleness left as soon as it arrived. I was completely enveloped in an instant. “Ho geez,” I sputtered. Her head bobbed vigorously on my member. “You sure don’t waste time do you?”

“She sure doesn’t,” agreed Dai.

The great mare’s hooves found their way between her legs, and soft wet noises began to pervade the room. She lifted her tail high, giving her husband an excellent view of her self-pleasure. She was clearly no stranger to putting on a show. I ran a hoof through her mane, and placed it firmly at the back of her head, guiding her bobs a little deeper.

The familiar *Glk Glk Glk* of a deep-throating mare began to ring out. I kept her pace slow and even, no need to finish so quickly. She moaned in pleasure, dining on the flavor and scent of my cock.

I couldn’t see Dai from my position, but I could hear him. He’d begun pleasuring himself, and he was not really a quiet masturbator. Heavy breaths and some small, frankly girlish, moans. It was kind of adorable, to be honest. A rugged mare and a dainty stallion, they made a cute couple.

“I’m close,” I managed to say after several minutes. She popped me out of her mouth and wrapped a hoof around me. She pumped with vigor as my climax came. Pangs of pleasure shook my body and my testes clenched. Ribbons of warm cum spilled onto my chest, each pump of her hoof adding another strand of white to my coat. I sat up, and smile tiredly at Coaldust.

“Having fun?” she inquired.

“You have to ask?”

She chuckled before giving my now-soft member a tender nuzzle. “How about you, husband? Having fun?”

“Yes, wife,” came a tired reply. His chest sweaty, his hoof cum-drenched, he was having fun. Coaldust rolled off me, giving Dai a proper view of my equipment. “Oh, lookit that. He is my size.” I, admittedly, took a glance myself. Our sizes certainly were certainly comparable. I wasn’t exactly going to break out a ruler, but we both shared a smaller than average fate.

“Ready for more?” asked the eager mare, eyes half-lidded.

“I think I… we…” I indicated her husband. “… might need to take five.”

“Hmm, too bad,” she whined. “I’ll just have to finish myself off.” Ever eager, she decided to give the two of us a show. She rolled onto her back and spread her legs wide. A delicate hoof reached down and began to rub her glistening lips. Her head rolled back and a moan escaped her throat.

“She always knows how to get my blood flowin’ again.” Dai sighed contentedly.

“Well, if I didn’t, ‘ou’d just stop after one,” she said, increasing her pace.

He laughed at that. “Maybe so.”

I decided to chime in. “I was actually going to say something. She must do this a lot; she’s good at it.”

“Yes she is,” Dai agreed.

She giggled through her ecstasy. “Well, thank you.”

Her legs went stiff, and lifted her hips of the bed. Her hoof shook like mad across her stiff little clit. “Almost… almost…” Without realizing it, I’d begun to run my hoof across my sensitive member. It was already at half-mast. She let out a long yell as she came. Her powerful legs buckled, and she collapsed back onto the bed. She brought her slimy hoof up to her face, and without hesitating began to hungrily lap up her juices.

That was all it took. Something about a mare delighting that much in her own body, devouring her own pleasure like that, it was… for lack of a better word… hot. So very, very hot.

Wordlessly, I crawled over to the mare. She ran a hoof across my cheek as I guided her onto her stomach. She yelped slightly as my hooves lifted her hips off the mattress. “Yes… oh yes,” she panted. Her legs opened wide, lowering her entrance . She knew how to fuck a stallion shorter than herself. That much was clear. I lifted her tail, taking in the view of her shining, juicy entrance.

I thrust myself into her. She was so warm, almost hot, and absolutely dripping. I didn’t bother starting slow, she was so ready. I started at a quick pace. Each thrust of my own was met with a powerful, almost hip-crushing thrust from Coaldust.

The stallion, apparently, had the same renewed vigor as myself. I could see him furiously pleasuring himself out of the corner of my eye. Looking back, I feel like it was the kind of thing that should’ve made me start think about stallions, but in the moment it didn’t bother me.

As the pace of things increased, Coaldust’s thrusts became more forceful. She lifted her chest off the bed, angling her body downward. I leaned back to compensate, putting us into a fun position for which I never really learned a name. It’s really just doggy style at an angle, so the mare is slightly on top. If I extended my legs beneath her, we’d be in reverse cowgirl.

But, I digress.

Coaldust’s powerful body bounced onto me, faster and faster. I’d given up trying to thrust myself; I was just throwing off her pace. She came with force. As climax gripped her, her hips fell onto mine. She collapsed forward, just in time for me to spill myself all over her backside. She relished her orgasm, her entrance still gaping, her muscles still twitching.

“Mmmmmmmm...” She toppled onto her side, contented. “It’s so warm,” she said. I wished I could see her expression, but a seed-covered ass was a fine view too.

“I hate to interrupt…” came the husband’s voice. I turned, and immediately had to stifle a laugh.

One spunk-covered eye squinted on his face. “… do you have a towel, or…” one large splatter of jism coated half his face. Despite my sense of professionalism, I actually chuckled a little.

Misfires are always funny.

“Sure, let me just get a few.” I climbed off the bed, my stallionhood dangling limply beneath me.

I decided we could all use a towel, so I sauntered over to a chest and pulled out three medium ones. I tossed one to my blinded client, and threw another onto the bed, which was mostly ignored. Coaldust leisurely rolled to face her husband. “Had fun?” she inquired sweetly.

“Yes,” he said, removing the towel from his now-clean(ish) face. “I don’t have to ask if you did.” He lifted himself from the cushion, trotted over to his wife. She stretched herself upward, and the two shared a small peck.

And there was that gaze again, that gaze that made me feel out of place. It felt so intimate, more intimate than the sex we’d just had. And then something peculiar happened.

“I love you,” they said. They. In perfect unison. Without any indication or signal, the two of them shared a perfect moment of mutual understanding. Then, I knew. I knew that I was looking at what it meant to be a couple.

Just because I was looking at it, though, didn’t mean I understood it. It seemed… impossible. They knew more about each other than they should be able to. It was… daunting.

The two shared a kiss and a quick nuzzle. I had to say something, anything before this moment dragged on any further. I’d frozen up before, but this time I refused to writhe in this again. “Look at you lovebirds.” Not my best work.

They blushed. “Aye, look at us, indeed,” said Greenhoof.

I’m not sure why I said what I said next. “I hope I have that with somepony someday.” Maybe it wasn’t just some random line to fill the conversation. Maybe it was true.

“Oh, I’m shoe-er there’s somepony out there for you,” said Coaldust in a tone that made me feel slightly pitied. “Especially bein’ as good as you are in bed.” Her husband chuckled as her took her hoof and helped her off the bed. “I meant to ask earlier, what is this bed made of? Is it floating?”

“It’s cloud. And yes, it’s floating.”

“It’s heavenly. Husband, buy me one of these,” she said jokingly.

“Yes wife,” he responded lovingly. I felt bad for the poor stallion. He was in for a nasty surprise should he ever look up a price.

“I have a shower if you’d like. Big enough for two ponies,” I tempted.

They took my offer, leaving me time to clean while they bathed. I had just begun loading my washing machine, when I heard... further activities from upstairs. Apparently, five orgasms between them wasn’t enough. Still, that’s what my big shower is for, really. Plus, it’s fun to get paid for other people having sex.

I was able to get everything cleaned up while the couple enjoyed my facilities. When they came downstairs, they were hanging off each other. Manes still damp, nuzzling like teenagers, they were quite darling.

“I trust you enjoyed the shower,” I said with a smirk.

The couple just giggled to themselves.

“Well, I’ve prepared some more tea if you care to join me for another drink.”

The couple shared a look. “Maybe just one, but after that, we better go. We're about to hit our third hour,” said Coaldust.

I nodded in understanding. "Please, sit." I poured three final cups as we all took out seats again. "So, I hope you enjoyed our session. If you did, you're always welcome back."

Greenhoof blew on his levitating teacup while his wife answered. "Oh, we'll definitely be back at some point." She took a sip before resting her elbow on the table. "That was so much fun."

"Aye, it was," agreed Dai. He leaned in to rest his head on her shoulder, and she placed her head on top of his.

I couldn't help but chuckle. "You two are so cute," I said.

They both laughed. "What makes you say that?" asked Coaldust.

"We'll you're both... so suited to your roles. You compliment each other so well. It's just sort of...darling."

Greenhoof raised an eyebrow. "How do you mean?"

"I just mean... all the things you do. You finish sentences for each other. You rest your heads together like that. You even share a desire for extra-marital intimacy. You just seem... to perfect together." As I spoke, I began to hear a hint of envy leak into my voice. "It's... just nice to see."

"Oh, well... thank you," he responded, turning slightly red. "It... just comes natural anymore."

"Aye it does," agreed the wife. "Over time, we just sort of... molded to fit together."

'How much time?' I wanted to inquire more. I wanted to ask them how their relationship got to this point. I wanted to ask them more about all the cute little things they do. I wanted to find out what I needed to do to get to that point. I wanted to know how to get what they had that made them so perfect for eachother.

"So how about you? Got a girl o' your own?" asked Dai.

I could feel myself blanch. "Well, it's... complicated. We're still figuring things out" 'Careful not to drop your act. You don't want to start gushing to brand new clients.'

Coaldust nodded before finishing a sip of tea. "I can imagine."

The husband polished of his cup and placed it gently onto the table. "That was lovely tea."

"Almost done, love," said the wife.

"Take your time, dear," he said with a grin.

Coaldust grinned back, and took another sip. "If you don't mind me sayin', Guilty, you're little lady is a lucky mare." With a loud clack, she set her cup onto the table. "I wish Dai could make tea this good."

Greenhoof feigned offense as the two rose. "We should get going, now."

I nodded. I would’ve loved to spend more time with them, but they were clients. I didn’t want them paying more than they intended. From his hanging coat, Greenhoof produced a medium sac of bits, and hoofed it to me.

I placed the sack onto my table. “Well, unless there’s anything else I can do…”

Coaldust laughed luridly. “Oh, you did plenty.”

“Well then… next time?”

“Next time,” they said. They again.

With a small farewell, they took their leave, neck-in-neck.

I was left with… a lot to think about.

Was that… was that the eventual path I would take with Derpy? Was I, in fact, getting a glimpse of my own relationship further down the line? Would I really have what those two have some day? Would I have to be that connected with Derpy? That trusting? That close? In some ways, the prospect is sort of... scary.

I suppose it’s not a good habit to compare yourself to others.

Not an easy habit to break, though. I can’t help but feel like… I’m failing somehow. I’m failing to be as loving as those two are.

I should probably get ready for bed. I have to bake a veggieloaf tomorrow.

Author's Note

FINALLY!

So much has been happening, I've been missing writing. Hopefully the next chapter won't take this long.

Once again thanks to my lovely editing staff: aquapunkchick, Blackskulls, coandco, Jake the Army Guy, and Unimpressive Vagaries.

And a special thanks to coaldust, for providing the OC couple for this chapter.

Letting Loose

Chapter 21

Letting Loose

“So what is veggieloaf?” Derpy asked, brow raised, voice thick with trepidation.

“Don’t sound so nervous. It’s good. I promise.” I carefully removed the searing pan from my oven. The delectable scent of cooked veggies pervaded the room. “Smells tasty, right?”

“It does,” Derpy admitted. “But it looks so weird.” Her eyes scrutinized the steaming meal. “What’s in it?” She had no trust for the dish before her.

“I can’t believe you’ve never had veggieloaf,” I said, placing it onto the stove. “It’s really just oats, breadcrumbs, and veggies. Eggs keep it together. The crust is ketchup. There’s also salt and spices and stuff. Pretty easy to make, too.”

“I mean… I’ve heard of veggieloaf.”

“Oh, I grew up eating this stuff.” I moved to leave the kitchen.

“Oh, did your—” She cut herself off violently.

“Yeah, my dad used to make it for me. He was actually a pretty decent cook. Good baker, too.”

“Huh… I thought you… and your dad…” I could hear her mentally tiptoe through the minefield of a subject she’d just broached.

“Well… he could cook.”

‘Change the subject. Now.’

“Anyways, let’s get these potatoes out of the water. They’re probably done.”

Derpy offered to set the table, while I prepared the rest of the meal. I had to remind myself that this was not a session, and that it wouldn’t be inappropriate to let Derpy help out. I mashed the potatoes with a little bit of butter and took the asparagus out of the steamer.

After our little meal was set, I uncorked a bottle of red wine. I fetched two glasses and returned to the table. “I hope you don’t mind some two-bit wine. It was the best I could find at Barnyard Bargains.”

Derpy paled. “Oh… Oh Guilty, I can’t drink.” Her voice came out carefully. She was worried she would offend me.

“Oh, I… I didn’t realize.” ‘Can she not drink? Did I know this?’ I couldn’t recall her ever saying anything about it. I suppose we’d never really discussed alcohol. “Do you… just not drink, or…?”

“No no, it’s just…” her hooves gestured frantically, attempting to explain what her mouth couldn’t. So nervous. “… my mornings start way early. I get up at five and—”

“Derpy,” I interrupted. “It’s fine. It’s not an interrogation.” My smile seemed to calm her down. “I'll get you some water.” ‘Good, date’s back on track.’

Even after my trip to the kitchen, her nervousness had not yet left, but now her attention was on the meal. She did not trust my veggieloaf, it seemed. Her little worried face was just precious.

I offered a bit of encouragement. “Try it, Derpy. It’s good, I swear.” I took a bite myself. It had turned out alright. A little burnt on the bottom, maybe. “If it helps, you can just slather it in ketchup. That’s what Crook always does.”

“No, no… I’ll try it.” She hesitantly forked herself a small piece. Her expression became strained. She slowly and purposefully chewed. “It’s not… bad. It’s just…” she looked for an appropriate word before swallowing. “…weird.”

“Weird how?” Too bad. If she liked it, I would’ve had something new to cook for her.

“I mean it tastes good. But, the texture is just… I dunno. I don’t have a word for it.” She didn’t want to upset me. Truthfully I wasn’t upset, just a tad disappointed.

“Well, don’t force yourself. There’s still plenty else to eat.” Reassuring smile. I continued to eat my own meal. ‘Talk about something. This is a date, Guilty.’ “So how is everything? Dinky? The girls?”

Derpy had started on the asparagus. “Good and bad. Dinky’s been behaving in school, but her grades haven’t been too great.”

“I know what that’s like,” I remarked. “I was never a good student.”

“You’ve said.” She smiled warmly. “That actually makes me feel a little better.”

“Well, good. A few Fs never killed anypony. I like to think I turned out just fine. I’m sure Dinky will to.”

Her smile grew. “You always know just what to say, Guilty.”

“You’ve said.” I took a bite of the potatoes.

“I wish I could do that.” She prodded at her veggieloaf absently. “Hey, would you mind maybe talking to Dinky for me.”

Now, I would’ve liked to maintain a good pokerface and politely decline. However, the hoof of fate saw fit to make me choke on my meal in surprise. I began coughing violently.

“Are you okay?” Derpy asked.

I managed to swallow with a bit of effort. “Y-yeah. Fine.” I took a large gulp from my glass.

“So? What do you think?” she inquired again.

“I…”

‘Okay think, Guilty. How do you get out of this? Say it’s not your place to counsel Dinky? Well, she’s asking for help; that would kind of be a slap in the face. Play the fool? Act like you wouldn’t know what to say? She wouldn’t believe it, she’d just reassure you.’

Derpy was waiting for a response. With each second that passed, her expression fell more and more.

‘I could tell her the truth.’ I looked into those sunset-colored eyes. Surely they wouldn’t judge me for it. ‘Besides, that’s what I should do, isn’t it? Be honest with my… girlfriendish pony of uncertain title. It’s not some grand secret, either. It’s just… embarrassing.’

“Derpy, I’m… kinda awkward around kids,” I admitted. My face felt warm.

“Really?” No frown. No subtle recoil. No disbelief, even. Surprise, yes, curiosity, as well, but… no judgement.

“Yeah… I just… don’t know how to talk to them.”

‘Crap, I’m blushing.’

“Dinky seemed to like you. She said you were nice.” Derpy took another hesitant bite of her loaf.

“Sh-she did?” I’d thought that was a miserable little interaction. She barely spoke to me. Too busy drawing her helicopter.

“Yeah.”

“What did she say?” I asked, perhaps a tad desperately.

“Just that you were nice. Nothing else, really.” Derpy took another bite of her loaf. “Spongey,” she said as she chewed.

“I’m sorry?”

“The veggieloaf, it’s spongey. That’s the word I was looking for.” Her expression was beginning to brighten. Was the meal growing on her?

“It is kinda spongey. I think it’s the bread crumbs,” I said with a grin.

She swallowed again. “You know, it’s not bad.”

“Well, I’m glad you don’t hate it.” I stared at my plate for a second. “How’s everything else, though? Are the potatoes good?”

“Really good. I looooove mashed potatoes,” she crooned.

“Who doesn’t?”

Derpy just giggled and continued to eat her meal.

I actually poured myself a glass of wine. I’d opened the bottle after all.

“So how are the girls? Lyra and them?”

A frown. A big one. “Goldy’s… kind of having a rough time,” Derpy admitted.

‘Fuck. I do not want to hear about this.’ I resisted the urge to run a hoof across my face. ‘But I brought it up. I can’t change the subject.’ I steeled myself. I would just have to endure.

“Lily’s not talking to her. She’s been mad before, but I think this time is serious.”

‘Offer a platitude. Comfort her.’

“I’m sure they’ll work it out. They seemed fine together the other day.”

“Yeah?” she asked, a trickle of hope in her voice.

“Yeah. They were just out walking. They said hi to me. It didn’t look like they were fighting or anything.”

“Hmm.” Derpy once again began poking her meal, rolling a stalk of asparagus back and forth. “When was that?”

“A… week-ish, I guess.” I took a quick sip of wine. “Do you know what happened?”

Derpy took a long breath, staring at her meal. She was wrestling with herself. Debating whether or not she should tell me what she knew. After that heavy moment, Derpy opened her mouth to speak.

I really wish she hadn’t.

“Lily… made it sound like Goldy was cheating on her.”

I think my heart actually stopped.

“But that… just doesn’t sound like Goldy to me. She loves Lily so much… even if she has trouble showing it all the time.”

I was barely listening at this point. My brain was already twenty steps ahead. I could foresee a dozen ways this could play out: Carrot Top murders me out of spite. Lily murders me out of jealous rage. Applejack murders me for being a homewrecker. Applejack murders me for trying to talk to her in the grocery store the other day. Applejack murders me because she’s a bitch.

“I asked Goldy, but… she wouldn’t talk about it.” She gave a heavy, tired sigh. “I dunno, maybe… maybe she did.” She rested her head in her hooves. “I just don’t know what to think.” She groaned tiredly. “Geez…”

I knew what Derpy was going through. She suspected her friend was making stupid decisions, and there was nothing she could really do about it. It’s a stifling experience.

I feel that way about Crook a lot. I watch Crook do stupid shit, and there’s this impulse. ‘If you would just let me live your life for you, you’d be so much happier. I love you, but you’re an idiot.’

Still, it’s not my job to fix his every little miss-step.

Even if it feels like it.

‘Okay, I need information. I need to know what everypony knows; that way, I can increase my chances of survival. Okay, Guilty, nonchalant. You’re just curious. You’re definitely not the stallion that Carrot Top’s been coming to for over a year to rut her stupid. You have no idea who that could possibly be.’

“So… wait, what exactly did Lily say?” I asked, totally innocently.

“She said… ‘I just can’t handle her stepping out on me anymore.’” Her eyes pleaded with me, begged me to offer her some other reasonable explanation that her mind had not considered.

‘Shit, that sounds bad.’ Scratch at back of head. Frown. Shake head. Gaze down. Appear to think hard on it. “I dunno, Derpy, I think that’s pretty… clear.” Apologetic face. “I… I don’t know what else she could mean.”

Derpy swallowed. “M-maybe she’s wrong, though. It… it could all be a misunderstanding, right?”

“It certainly could. No guarantee it’s not all a big mix-up.” The response was automatic, and the pangs of guilt were immediate. ‘I should not have said that.’

Desperate eyes looked up at me. “You think so?”

‘Lie… lie, you bastard! You are absolutely, one-hundred percent, completely forbidden from telling her the truth. It breaks your cardinal rule.’

I knew I couldn’t tell her the truth, but… it just felt so dirty to give her… false hope. I knew Carrot Top was stepping out on Lily. She was doing it with me.

Sadly, that did not stop me from lying.

“I do.” Serious Expression. “And if… something did happen... I’m sure they’ll work it out.”

Derpy managed to crack a smile. “I… I think so too.”

‘Bravo, Guilty. You’ve successfully made this easier for her to swallow now, at the cost of making it harder for her later.’

I knew right away that I’d made a mistake. Eventually word was going to get out that Carrot Top was a client of Guilty Pleasure. And the moment that news came out Derpy was going to remember this exact moment.

And I was not going to be the good guy in that little story.

“So anyways… um… can we change the subject?” She laughed nervously.

“Dear Celestia, please… something less awkward. I’m so sorry I brought it up.” Equally nervous laugh.

My apparent nervousness diminished hers. She giggled with a bit more joy as the stress flowed out of her. “So, um… anything interesting happen to you lately?”

‘Okay, Guilty. The rough patch is over, back to our regularly scheduled programming. You had a rather exciting story planned, did you not?’

“Actually something did happen to me.” Derpy’s raised an eyebrow, curious. “I saved a life.”

“Wait… what?”

“Do you remember those things that chased you when we went hiking?”

I spent the next few minutes regaling Derpy with my heroic tale of the mantle ray’s rescue. Derpy didn’t have a great experience with those rays, so in the beginning she wasn’t exactly sympathetic. By the time I finished though she was glad that it was okay.

“So, wait. Where is the ray now?” she asked.

“That Fluttershy girl took it. She takes care of animals or something.” I could feel my face getting warm from the wine.

“Oh! We should go visit!” Derpy bounced excitedly in her chair. “I wanna go see it.”

“You sure? Not afraid it’s going to eat you?” I teased.

She shot me a look. “Hey, shut up. They were chasing me. What would you have done different, huh?” she asked in mock anger.

“Nothing, probably.” I noticed that Derpy hadn’t touched what remained of her meal in a few minutes. “All done?”

“Yeah.”

I grabbed her plate and mine. “I’ll just get these.”

“I’ll get the glasses,” she offered, rising from her seat.

“I got it.”

“No, I’ll help.”

“…Alright.”

Old habits.

Dinnerware in tow, we returned to the kitchen. “So, what next? Dessert?”

“Hmmm… I have some ice cream. I dunno, I’m not really a dessert guy.” We deposited our dishes in the sink. “I think I might have, like, a frozen cobbler or something, want me to check?”

Instead of an answer I received a very soft and warm sensation from behind. It took me a moment to realize that Derpy had sidled up to me and wrapped her hooves gently around me.

A big grin was spread across her face. Her eyes were half-lidded. “What are you—?” I was cut off, as Derpy’s lips connect with mine. ‘Oh right… kissing... this is a thing.’

It was different than last time. She gave me no tongue, nor I her. It was simply a long, firm peck. I liked it. It was nice, I wasn’t flailing my tongue about, smacking my lips like a moron, I was just… smooching. I began to push back a little. I liked this a lot.

When Derpy pulled back, I lurched forward, chasing the warm feeling with eager momentum. When I caught myself and opened my eyes, Derpy was still smiling? ‘When did my eyes close?’

“Was that okay?” she asked.

“Y-yeah… that was… great.” I could still feel it on my lips. It tingled.

“Good,” she smiled proudly. “We’ll start slow, and you’ll work your way up.”

I smirked at her. “So what, you’re teaching me kissing now?”

“A little, I guess. I just…” a blush touched her cheeks. “…I want to kiss you. I like kissing.”

I felt myself blush in turn. “Well, uh… I like kissing you, too.” ‘Guilty, you’ve had your tongue inside this mare. Why are you blushing over a little kiss?’ I hastily thought of something to say. “Why don’t we take a seat by the fire?”

“Sure,” she replied.

Moments later we were parked in front of my roaring fire, leaning into each other. I sipped what remained of my wine, as the two of us stared into the flames. We didn’t speak, just enjoyed the moment. I love being able to do that with somepony. To be able to just truly just experience a moment together. It’s not an awkward silence, it’s different, it’s like... both of you realize that nothing needs to be said, and that’s okay.

I felt feathers on my back as Derpy draped her wing over me. She decided to break the silence. “I love your fireplace. It’s much bigger than mine.”

I smiled. “Yes, it’s very nice. I made sure they put it in.”

“Oh, that’s right. You had this place built. I forgot about that.”

“Yeah… Blew through a lot of my savings. Worth it, though. This place is almost perfect.”

“I remember when it was being built. I helped deliver some of the lumber.”

“Really? I was never really around for the construction.” I briefly wondered if Coaldust had helped build my house. I imagine she would’ve mentioned it if she had. “Was it a big deal? The house being built on the edge of town?”

“Kinda. More than that, the fact that you were an escort was what people talked about. We didn’t have an escort before you got here.”

“That’s actually part of why I moved here. I mean, it’s fantastic not having competition, but more than that, I just wanted to get away from… the business side of the business.”

I could feel Derpy hesitate. She wanted to ask me about it. About what made me move away. The words were on the tip of her tongue.

She lost her nerve at the last second, and said something else. “Well… at least you own some land now. Goldy says owning a home is a smart thing to do. I wish I owned my home. I just rent it.”

“I actually own quite a bit of land. I had to buy the whole acre.”

“Really? Wow. An acre’s a lot, huh?” she asked.

“More than I need.” I took a sip of my wine. “I really am starting to like it here. There’s a lot of things I miss, but… Ponyville’s growing on me… slowly.”

“What do you miss?”

“Oh geez, where to start. I miss places being open late. If you want food after ten here, you’re out of luck. I miss the smell of pavement, everything’s dirt roads out here. The neverending din of carriages and hoofsteps and horns that lulls you to sleep. I miss a lot about Manehattan.”

“You should take me there,” Derpy declared.

“What?”

“You should take me there. To Manehattan. You sound like you love it so much… I want to see it.”

My head was alive with Ideas. ‘Central park. The museum of fine arts. We’d have to get pizza somewhere. I should take her to a ball game. Oh, and we definitely need to get some noodles at that place on 8th. I need to make a schedule.’

“Yeah, we could…” I felt myself smiling. “We could do that. An overnight trip or something.”

“That would be nice.”

“Yeah, I haven’t been back since… since I moved here.” I began to realize just how long I’d been away.

Before I could begin sulking, Derpy spoke again. “Hey, Guilty?”

“Yeah?”

She placed her hoof onto mine. “Let’s have sex.”

The way she that… I don’t know… it filled me with energy. She rose, and I followed, eager as ever to dive into Derpy. Once we got into the bedroom, I quite literally did. When I stepped into the room I tackled her onto the bed.

She laughed mirthfully as we rolled onto my cloud. “Guilty, what are y—?” She gasped loudly as I kissed her between her wings. My attack was so furious. I kissed and nipped at her sensitive spots with vigor. My focus began to wander, and Derpy’s body slowly turned to putty in my hooves. “G-guilty! Why are you… t-t-teasing me so hard?”

I didn’t answer. I was busy, nipping at her sides. Tickling her haunches. Kissing her. Smelling her. Tasting her. Partaking of her. Indulging in her.

“Y-you’re not normally like this!”

Was that unease in her voice? My momentum came to a halt. “Is that bad?” Never hurts to check.

She was panting, grateful for a brief respite. “No, I… I like it. It’s just… different.”

She was right. These were not Guilty’s practiced maneuvers. This was not the art of the oldest profession. This was just… playful. Self-indulgent. Almost masturbatory. I was not performing one of my many many acts; I was doing this because I wanted to. I wanted to tease her. I wanted to poke her and prod her and watch her writhe. I wanted to feel her squirm beneath me. As I stared down at her twitching body, I realized something.

This wasn’t very Guilty Pleasure. This is what I used to do before I learned how to fuck. This was just… fun. It was so fun. It was more fun than I’d had fucking a mare in forever, and we’d barely begun. Our session on Sunday may not have been all that different, but this… this was a new breed of pleasure for me.

“Do you mind…?” I began to ask. “Do you mind if I’m a little selfish tonight?”

I think she may have been a bit taken aback with the earnestness of my question. I’d been sincere. Perhaps overly so. Regardless, she simply smiled and shook her head. “I don’t mind.”

So, I did something that I hadn’t done in a long time: I had sex with a mare outside of the familiar territory of “a session.” Only the faintest hint of unease resonated in the back of my mind as continued my assault. I slowed down, letting my hooves truly explore Derpy. I knew her body well, but it never hurts to reacquaint oneself with something familiar. Her round ass. Her delicate wings. The slight sway in her back. The stretch marks on her barrel. The cellulite on her ass.

It was… sort of hypnotizing. I knew these features. I knew just about everything about this mare’s body, but that didn’t stop me from being entranced by it. Something about her that night just… pulled me in.

And it kept pulling until I could bear it no longer. After Derpy had become putty in my hooves, I thrust my face into her sopping entrance. Her back arched as pleasure shot through her. “Oh…” she moaned. Her legs spread wide as I ran my tongue along her lips. I wasn’t tickling or probing or thrusting, like I normally would. I was just tasting, hungrily slurping away, trying to get as much flavor as possible out of her sour nethers.

Regardless of my intent, Derpy climaxed. Her breath became heavy as her body clenched in spasm and her wings outstretched as every muscle tensed within her. As pleasure subsided, she went limp, melting into the bed, more liquid than mare. “You really like that, huh?” she mumbled through the mattress.

“Like what? Licking you?” I never stopped my caresses; I reveled in the feeling of her coat against my hooves.

She nodded weakly. “Uh-huh. You always do it… but you really got into it right now.”

“I didn’t… really feel like I was trying harder than usual.” I wiped the juices from my lips.

“I dunno… you just seemed really… hungry for it, I guess.” She rolled over onto her back. Her blushing lips glistened, and a warm smile gazed up at me.

“Well, I… I like eating pussy.” She tucked in a wing to make room as I laid down next to her. “It’s warm and it tastes good and… it’s fun.” ‘Am I defending cunnilingus as a concept?’

Depry chuckled a bit. “Geez, Guilty, don’t get so serious on me.” She rose, sliding herself downwards. “My turn,” she said gleefully. I closed my eyes as Derpy’s performance began. She likes to start slow. A gentle hoof caressed my shaft. Hot breath tickled my sensitive loins. A small peck was placed on the head of my cock. “I like it too, actually. It does taste good. And, it is fun. I like making you cum.” Pleasure enveloped me as Derpy took me into her mouth.

In my moment of rest (and fellatio) I had a small realization. ‘I suppose this is what I like about Derpy. Sex is fun to her. She’s very casual about it. It’s not the deep dark desire she buries within herself, it’s just… another thing to do. I guess that’s kind of how I feel about sex.’

I’ve considered that maybe that’s because I have so much sex. When I was young, getting laid was like a challenge. An obstacle to be overcome. A quest to be completed. But becoming an escort changed sex. Sex wasn’t something I had to try for; sex was routine. I suppose in some ways that took the magic out of it. But at the same time, it didn’t stop being fun. I still liked (most) of the sex I was having, It just wasn’t as… important.

It was just sex.

And with Derpy sex is “just sex.” She never needs any special treatment, never hard to please, doesn’t need it like some ponies. She just likes the feeling of being with a stallion, just like I like the feeling of being with a mare.

It’s good to have common interests.

The oh-so-familiar feeling of climax began to creep up on me. “I’m getting close.”

“Mmhmm,” came Derpy’s cock-muffled acknowledgement. She increased her pace. Her tongue swirled around my head between gulps. I came quicker than I thought I would, and my jism shot directly down into Derpy’s throat.

Derpy gagged and pulled her herself off of me. A few wet coughs sent little droplets of semen and spittle all over the sheets. “Wrong pipe,” she managed squeeze out in a ragged voice.

“Y’alright?” I asked.

She nodded, still coughing. After a few moments, the coughing died down. She took a few good deep breaths before raising her head. “I’m okay,” she assured me.

I smiled. “Good. Do you wanna stop, or…?”

She giggled. “The mood’s kind of dead, huh?”

“Just a little, but I don’t mind. We can keep going.” I ran my hoof across her cheek. “I’m just happy to be with you.”

She blushed hard. But, rather than shy away, she leaned into my caress, nuzzling my hoof. “I’m happy to be with you, too.”

“Well, aren’t we fucking sappy,” I joked.

“Apparently,” responded Derpy. She stretched her limbs and flopped back onto the bed once more. “I love this bed.”

“Me too.” I flopped down beside her. “Especially when you’re in it.”

“You’re such a dork.” I felt the tickle of feathers as a wing was draped over me and Derpy’s body leaned into mine.

I leaned back, enjoying the warmth of her.

The next thing I knew I was dreaming again. Another half-dream without shape. Red and gold and silver smoke. I waded through color for what felt like ages.

“Mmmwhat time izzit?” I heard a tired pegasus ask. Just like that, my dreamscape vanished, disappeared like the smoke that it was.

I looked for my clock, eyes bleary. “Seven-thirty. We weren’t even out for ten.” I let loose a yawn. “Felt like longer.”

“It did… I can’t believe we just fell asleep like that.” She stretched every limb and lifted herself from the mattress. “I need to… wake up,” she yawned.

“Shower?” I offered.

She nodded tiredly. “Sounds good.”

So, we went upstairs. Once in the shower, Derpy began her usual meditative trance, while I began to scrub myself. I was in the middle of scrubbing behind my ears when she spoke.

“Hey, Guilty?” Her tone was hesitant, cautious even.

“What’s up?”

“I, uh… I think I realized something today.”

“Oh?”

“You… you’re normally always catering to me when we have sex, aren’t you?”

“Of course I am.” I let the warm stream wash the suds from my head. “That’s what you pay me for.”

“I mean, I guess I knew that. But… I never appreciated… how much you actually cater to me.” She was beginning to blush. “You always make me feel so good. You knew where to lick me, and you know how I like to be mounted. You know just how to get me off.” There was a pause. “Today was different, though. It wasn’t as… good. I mean, we didn’t go all the way, but… even the parts we did get to, were so… different.”

I couldn’t help but frown. “Sorry, I guess I kinda… didn’t have my head in the game.” A niggling feeling of guilt began to build up in me. I shouldn’t have been so selfish. Should’ve spent more time giving head. I should’ve pulled out so she didn’t choke. Should’ve been more gentle, she likes gentle.

Derpy interrupted my mental tirade. “But… you seemed more… present for it… if that makes sense.”

“How do you mean?”

She shrugged. “I don’t know. You seemed to… enjoy today… more than usual. I guess.”

“I… I guess I did. It was refreshing… not being… in the act.”

“In the act?” Derpy asked.

I swallowed. I hadn’t meant to “talk shop,” as it were. The concept of “the act” is something I’d never discussed with somepony who wasn’t also a whore. Part of me felt as though I was about to break some long-held taboo.

“I mean… when I’m… in a session. I have to be… ready… horny… attentive. I need to be a perfect bedmate… sometimes more. It can be… tiring.”

“Is it… like that with me?” Same nervous tone.

I hesitated. Part of me wanted to tell her not to worry, that it was different with her. I wanted to comfort her, and tell her not to worry.

But… I’d already told a white lie to her today. I didn’t want to do it again. “It is. Not as much as with some clients, but… You are always my top priority in a session. I come second… literally.”

My joke fell on deaf ears. Derpy’s expression began to betray feelings of guilt as well. We were two peas in an awkward little pod. “Geez, now I feel… kinda bad.”

Reassuring smile. “Don’t, Derpy. You’re just getting what you pay for.”

She took a few moments to respond. “I mean… I guess. I just… never really… thought about it all that much.” She looked up at me. “You must have a really weird… relationship with sex.”

I nodded as I looked for a response to that. “I mean… yeah… I do. It’s not a bad relationship, but it is… a bit complicated, I guess.”

It’s not exactly a secret that whores have to treat sex differently than other ponies, but it wasn’t exactly a conversation I’d planned on having today. “I have… professional standards. Sometimes they keep me from enjoying sex as much as I’d like. Sometimes it means I have to have sex that I don’t necessarily enjoy.”

“How do you mean? Standards?”

“Well, I mean… I’ll almost never turn down a client, no matter what they want to do with me, what they want to do to me, what they want me to do to them. Some ponies just want to be fucked a certain way, but others want to… be tied up… tie me up… hurt me… want me to hurt them. But… just because I don’t necessarily like it, doesn’t mean that I won’t do it for a client. That’s… just business. That’s the service I offer.”

“So… you don’t like that? Being tied up and stuff?”

I shook my head. “Not really.”

“I’ve never tried it.”

I just shrugged my shoulders. “It can be fun,” I admitted.

Derpy just looked pensive for a moment. “Hey Guilty?”

“Hmm?”

“If I asked you… to fuck me like you did today... from now on… would you? I mean… you didn’t actually fuck me, but… you know what I mean.”

I cocked my head to the side. “Is that what you want?”

“I… I think so. It might not have felt as good, but… it feels like it made you happier. I… I like that you’re happy about it. I get the feeling you don’t get to do that very often.”

‘She’s not wrong.’ “Derpy, you don’t need to do that on my account. I’m perfectly happy with our usual routine. Besides, my pride as an escort wouldn’t allow it: nothing but the best for my clients.”

She thought for another moment. “What about… when I’m not a client? When it’s like tonight, just a date.” Her face still looked a bit sad. She was almost pleading with me.

“I mean… that… that would be fine, I guess. Honestly, I’d feel a little… weird about it.”

“But… you did it right now.”

“And I feel a little weird about it,” I confessed. “I feel kinda bad about being so selfish.”

A hoof quickly found my shoulder. “Please don’t, Guilty!” Such earnestness. “It may not have been as… mind-blowing as normal, but… but it was still really nice.”

“I mean… if you like it—”

“Guilty, I like it. And, I want you to like it, too. Okay?” She leaned in and nuzzled me.

“O-okay.” I nuzzled back, but I felt kind of awkward. This felt like pity. I don’t really like being pitied. I considered saying something… reassuring her… convincing her that everything was fine, but… I decided against it. I could always address it later. No need to start something when we’d just finished. “We should get out, now. I think I’m starting to wrinkle.”

We exited the shower and began to dry ourselves. “You have the best towels, Guilty.” She buried her face into my (admittedly pricey) cotton towels. “thrrrr so svvvvt.”

“You are too cute.”

She removed her towel, revealing her blushing face. “Don’t say that… it’s embarrassing.”

“Then stop acting cute,” I responded whimsically as I bopped her on the nose.

She glared daggers at me. Luckily, her ire was temporary. “Anyways… thanks for having me over. This was really nice.”

“Well, I’m glad you’re having fun. We can do this again… anytime.”

“Sure!” There was genuine excitement in her voice.

After we dried off, and headed downstairs, Derpy took her leave. As she left she… she gave me another kiss.

It might sound a bit silly, but… I’m glad that that makes me as happy as it does. I’m glad that I… I kept myself from kissing clients. I’m glad I have something like that’s still… intimate. If I’d allowed myelf to kiss clients, this might not feel as… great as it does. I’d be desensitized.

I mean… I am a bit desensitized when it comes to sex. No way around it, I’ve had… a lot of it. It’s not as though I’m… physically desensitized, it’s just… There’s this feeling you get. The first time you get into bed with someone, the first time you’re intimate, you feel lighter than air. Your pulse raises and ecstasy builds within you. It’s… it’s great.

But over time that feeling gets weaker and weaker with each new partner. That thrill… begins to die. For me it basically is dead, tragic as that may sound.

But, when Derpy kisses me… I… I feel it again. I feel like I did when I was barely a stallion, getting laid for the first time.

I’m just… so glad I didn’t… spoil myself completely.

The kiss ended, and she gave me a quick nuzzle. “So we should go visit that ray soon,” she said. “I’ll ask Fluttershy tomorrow when a good time is.”

“Sounds fun.” A small part of me died, as I realized she was leaving now.

“So… see you Sunday?”

“See you Sunday.”

She walked out the door, took twenty paces, turned, waved, and left.

Derpy’s departure was not met with the same… emptiness as last time. Leaving, and knowing that she was coming back filled me with a sort of… anticipation. I can’t wait to go see that ray with her.

There was, however, a niggling feeling in the back of my mind. ‘What’s going to happen at Carrot Top’s next visit?’ At the risk of spoiling my good mood, I decided to check my ledger. ‘I think she has an appointment booked.’ Sure enough she did.

Her next appointment is the day after tomorrow. I’m not sure what to expect. Will she even show up?

Whatever the case… I’m not looking forward to it.

Author's Note

FINALLY!

This was a pain to get out, honestly. I'm on this TERRIBLE SCHEDULE where I have a mid-term exam every two weeks. Don't get me started.

That said, I like how this one turned out.

Thanks to the crew: Jake The Army Guy, unimpressive vagaries, coandco, aquapunkchick, and BlackSkulls.

Angry Spouses

Chapter 22

Angry Spouses

My head throbbed. I resisted the urge to rub my temples. I fought hard to keep a pleasant smile on my face. “Tea, anypony?” I managed to say in a friendly tone. Carrot Top and Lily had already been here for quite a while, and my patience was beginning to wear thin.

Carrot Top said nothing as her gaze burned into my table. She paid me no mind. She was too busy desperately wishing she was somewhere else.

Lily on the other hoof… well. “Oh, I’d just love a glass, Mr. Pleasure,” she practically sang. “Such a fine host you are.” Her tone was nothing but joyous, and a lesser stallion might’ve thought all was well, but there was not truly a trace of glee in her mind. Behind false mirth lay casks of venom. “No wonder Goldy visits so often.” Her sickly smile unnerved me greatly.

Still, I was no stranger to the “everything’s fine” game. I’m actually quite good at it. “Well, I’ll just put the kettle on, then. Be right back.” Courteous smile.

As I picked out a tea, and set the kettle to boil, I ran over the past few minutes in my head. Lily had arrived with Carrot Top. Honestly, I’d half-expected that. Lily was happy. That I hadn’t expected. Not real happy, though. Fake-happy. Playing nice just to spite us. Yes, us. I actually seemed to find myself in a situation where Carrot Top was something of an ally. Unfortunate alliance aside, I needed a game plan.

I’d been in this situation before. Angry significant others are just a part of the job. If the worst Lily had to offer was a poison attitude, I knew I’d be fine. ‘Okay, so how do we approach this? We’ve already begun to play her little game; now we need to win.’ I took a deep breath as I prepared myself. I would be biting my tongue a lot. ‘Ultimately though, I should try and figure out exactly what’s going on between them. Play along and pry when possible. It’s as good a plan as any right now.’

I returned to my living room and my forced smile returned with me. “Well, that will just be a minute.” I sat across from the divided couple once again. “So, Lily, I wasn’t expecting you here. Not that it’s unwelcome, I just would’ve preferred a bit more time to prepare.”

“Well, it was a spur of the moment thing. Right, dear?” She gave Carrot Top a little shake.

Mildly surprised, the mare looked up for the first time since she arrived. “Lily… what are we doing here?” She was clearly in no mood for Lily’s little act. “Let’s go home. We can talk about this.”

“But we only just got here. We can’t leave now. Besides, Guilty just put on tea for us.”

“Lily… please… don’t be like this.”

I spoke up before Lily could give a cheery retort. “I assure you, Ms. Harvest. It’s fine.”

Her gaze narrowed, and I could practically see the gears turning behind her eyes. ‘Is he on my side?’ they seemed to ask.

“See, sweetie? It’s fine. Mister Pleasure doesn’t mind that I’m here.” Her disdain for Carrot Top bled through her act for only a moment. A single sour note in an otherwise joyous tune. “So, what’s on for tonight? I’d love to see what goes on in these little… appointments. Is that what they’re called? Appointments?” Her smile looked as though it could cut glass.

I was getting into the swing of things. My baser instincts screamed at me to just diffuse the situation, but my baser instincts are kind of pussies. Swallowing my irrational fear of conflict, I managed to keep a smile on my face, and cheer in my voice. “I prefer ‘session’, but call it whatever you like. Either way, I’m sure tonight is going to take several interesting turns. For now, though, let’s just talk. How’s everything going for you two?”

“Oh, everything’s just super!” Her voice hit an octave I didn’t know existed. “Goldy and I were planning on going down to Los Pegasus for our anniversary. Oh, but that’s probably cancelled at this point, isn’t it dear?” She gave her lover another shake, this time with a bit more vigor.

She was not pleased. “Lily, stop!” protested Carrot Top.

“Oh, sorry, honey. I’m just so excited to be here at one of your little rendezvous.” She turned to me. “So what does happen at these little meets? Goldy’s been ever-so-shy about it.”

My smile grew smug. “I’m sorry, Lily, but I am forbidden from divulging the nature of a session to anypony but those present at the time, nor can I confirm that any such session has ever even occurred. I will neither confirm nor deny that either of you has not visited me before this very night.” My practiced line cracked her mask, if only slightly. A brief, but noticeable scowl flashed across her features.

“Well, aren’t you... professional?” she responded, repairing her act in an instant. “But, Goldy’s already confessed to me that she’s been seeing you almost since you came to town. Certainly it’s okay now, right?”

“I’m quite sure I can’t comment on that.”

She beat back a sour expression. “Oh, is that so? Such a shame. There’s still tonight, though. Oooh, I can’t wait to see what fun little things you two will get up to.”

I moved to strike. “Just us two? Does that mean you won’t be joining us? The bed is quite large, there’s more than enough room.”

Lily blushed up to her ears and Carrot Top gaped at me in shock and anger. Truth be told, I wasn’t really planning on bedding either of them tonight; I was just trying to rattle Lily out of her act. Carrot Top may not have liked it, but I could suffer through her ire for the time being.

So, just like a normal session, really.

Lily stammered her way through a response. “Oh, I… I couldn’t… I’d never…” She shuddered in disgust. Not a straight bone in her body, it seems.

“Then again, you’ll have a front row seat to anything that does happen. Would you like that?” She opened her mouth to respond, but I pressed on. “Would that please you… to watch us? It’s a fairly common request, as far as couples go. A private little show. Just for you. And you’ll have a seat right there by the bed, where you can see… everything.” I made use of my seldom seen diabolical smirk.

Lily’s face began to lose composure as unwelcome images assaulted her mind. I was trying to remind her of what had made her upset in the first place. With any luck, it would be enough to get her to lash out… get upset. Anything to get her to abandon her little game.

“That’s enough!” cried Carrot Top, to both my Lily’s and my surprise. “Both of you!” A moment of silence confirmed that we had both, indeed, stopped. “Look… that’s enough of this… whatever it is you two are playing at. Lily… let’s just go. We’ll talk about this on our own. We don’t have to do this here.”

Now, what Carrot Top had just done, whether she’d intended to or not, was give me an out. She gifted me with an opportunity to distance myself from this situation. I could just send them back into the night with an “I’m sure you two will work it out.”

However, I’d like to think I’m a better pony that that. This was a session, and It would only be professional to help them while they were here. Even then, I like helping ponies… even bitchy ones like Carrot Top. And for once, the context was such that I could help these two.

Lily’s true voice was finally heard, and the game was over. The hurt, angry, betrayed mare spoke in a bitter tone. “I just… I just don’t get it.” Gone was the giddy little creature that I’d been sparring with, replaced with a sad, fragile mare. “I just don’t get… why. What does this… does he… do for you that I can’t.” Out came the tears. “I... I just want to know… w-why I’m n-not good enough.”

Exasperation coursed through Carrot Top. This was the continuation of a conversation, clearly, for her to be tired of it already. “Lily, that’s not—”

“I-I’m never good enough. Y-you won’t… you won’t let me move in with you. You w-won’t kiss me in public. You—” she heaved heavily as more tears came. “You n-never tell me you love me anymore.” She brought face out of her hooves and leveled her eyes with Carrot Tops. Carrot Top, to her credit, did not flee the gaze of her openly crying lover. “It’s like we’re n-not even d-dating anymohooohooooore.” Her face hid once again behind her hooves as she began to bawl like a child. Pent-up emotions were spilling all over my table.

My kettle took this exact moment to be the best possible time to start boiling.

My kettle is an asshole.

“Hang on… I’ll get that.” I rose hurriedly to address my shrieking appliance. “Does, uh, anypony still want tea?” Lily nodded pathetically from behind her hooves. Carrot Top gave a slight nod as well, too busy with Lily to remember that she hated me. I returned with a few cups of black tea on a small tray. “Here.” I slid a cup in front of each of them. Things were moving a bit faster than I expected. Lily must’ve been on the edge of tears since she got here.

For a time everypony was silent, save the quiet sobs of the pink mare with a flower in her hair. Carrot Top and I exchanged glances every now and then, but we mostly tended to our drinks. After a few minutes Lily had worked up the fortitude to raise her head. “I’m… I’m so sorry, Guilty.”

“Don’t be. You—”

“No… I… I just wanted to make a scene.” She finally picked up her now-cold tea. “I… I didn’t need to involve you in this.”

“Think nothing of it. I think of you as friends, you don’t even have to ask.” She smiled at that.

She put down her teacup. “We should really be going, then.”

“Stay,” I interjected. Both mares gave me a disbelieving look. “You’re already paying for an hour; you may as well use all of it. Am I right?”

Lily sighed tiredly. “You really are being too kind now, Guilty.”

“Lily. If I may… weigh in.” She gestured for me to continue. “This… is a safe place. Nothing that is said here will be repeated outside. It will never leave the confines of these four walls. And, you two, if I may make an assumption, desperately need a proper forum to communicate. Right now the both of you are my clients. I… urge you to make use of this opportunity. I urge you to make use of me, while I am yours. I’m a good moderator. I’ve done this sort of thing plenty of times.” I gave them my most earnest look. “You’re my friends, and I want to help. So, please… allow me to. I know that’s selfish, but—”

“Selfish!?” Lily exclaimed. “Oh, Guilty, you are just too… and after the way I was acting…”

Carrot Top did not share her girlfriend’s grateful attitude. I could feel her apprehension. It practically permeated the air. “I don’t… like this,” she admitted.

“Oh, for Luna’s sake.” Lily whined. “Why not?”

“I just…” Carrot Top desperately looked for an excuse. “I’d rather get through this on our own.”

“Well, news flash, Goldy. We’ve been trying to… for a while now. It hasn’t exactly been working!” Lily was shocked at her own outburst. “I just… I think we should try this.”

The nervous orange mare continued to squirm desperately, trying to escape from my home and my session. “Lily I just—”

Lily exploded. “Fucking… work with me here!” That was the first time I’d heard her swear. Sweet, kind, gentle Lily was suddenly a creature of fury. “Will you do this one thing for me? Will you please just fucking try this?” She ran a hoof down her face, her visage manic. “I’m at my wit’s end here, Goldy. Because, I want us… to work, and I am tired of… fighting you to make it so. So please… let’s try this… because without Guilty… I am out of fucking ideas.”

Carrot Top swallowed deeply, before once again staring at the floor. “O-okay,” she relented. Perhaps she had underestimated just how much hot water she was in, or perhaps she was simply shocked to hear Lily shout like that. Whatever the case, any further objections were not voiced.

I cleared my throat. “Well, if that’s settled… some ground rules.” They nodded. “First and foremost: no shouting. We’re not going to make any sort of progress is this turns into a screaming match.” Lily nodded in agreement. “Second: no interrupting. Both of your thoughts and opinions are valid, and deserve to be heard.” Once again, Lily nodded. “And, finally: don’t antagonize. I understand that both of you are upset, and that’s fine, you’re allowed to be upset, you can give voice to that anger here. But don’t be hostile or confrontational. Once again, that’s not going to solve anything. Does that sound okay?”

“Yes, of course,” replied Lily. Carrot Top remained silent.

Before Lily could snap at her, I spoke. “Ms. Harvest… You’re going to have to make an effort here. I understand that you’re uncomfortable, but I need you to meet me half-way. So, please, do yourself the courtesy of being present in this conversation.”

Carrot Top raised her head slightly. “That sounds fine,” she said laconically.

“See what it’s like trying to talk to her?” Lily said.

“Lily, please… don’t antagonize. I’m not taking a side here. You don’t need to try to convince me of anything.”

“Oh… I’m sorry, I… I’m sorry.” Lily’s gaze now drifted downwards, as shame began to grow on her face.

“Don’t be. Now, before we proceed. May I speak with Ms. Harvest privately?”

Lily looked surprised. “Oh, um… of course.” She looked around my home. “Should I—?”

I pointed off to my right. “The bedroom’s right through there. This will only take a moment. I’ll let you know when we’re done.”

“Uh… okay.” Lily made her way through the door, and Carrot Top’s spiteful gaze rose to meet mine.

“What are you playing at?” she asked darkly. “What are you even trying to do?”

With Lily out of the room, I no longer felt the need to hide my annoyance. My brow furrowed and my hooves found their way to my temples. I rubbed slowly to ease my splitting migraine. “You wanna know what I’m tryin’ ta do, Carrot Top? I’m tryin’ to help Lily.” No proper accent. No act. No nothing. This was just truth.

I gave her an unamused look. “I don’t like you. You don’t like me. That’s fuckin’ fine. I don’t give a shit.” It felt good not to filter myself. “But I think Lily is a sweet, darling mare. She’s a friend. An’ that fuckin’ means something to me.”

Carrot Top remained silent, still baffled at my accent, I think. “I’m not gonna pretend to understand why exactly she likes you, but she does. And, being the decent fucking pony I am, I’m going to try to help her patch things up with you. Because that’s what friends fuckin’ do. Now I don’t know if you two can actually patch things up. Seems like you’re in a pretty bad place right now. But I am gonna fuckin’ try to help. And to do that properly, I need two things from you.”

She rolled her eyes at me. “And what would that be?”

“First. I need you to cooperate with me. I need you to actually fuckin’ try. Because you have been spending the better part of this appointment starin’ at the fuckin’ woodwork. Second…” I returned the act. This was a proper request, and as such, should be asked in a proper way. “I need your explicit permission to discuss both the existence of, and the nature of your previous sessions with Lily.”

She looked aghast. “W-why would you need to do that?”

“Because I can almost guarantee it’s going to come up. Without your permission, I must remain silent on all such matters. That silence will bring this conversation to a screeching halt.”

She groaned audibly. “Why do you even need my permission?”

“Two reasons. I need your permission because it is my most cardinal rule. Discretion is the very nature of my business. It is sacrosanct. More importantly however… I need you to trust me.”

She scoffed. “Trust you?”

“Yes. When you came to me so many months back, you trusted me to keep your sessions a secret. I cannot betray that trust now. If this conversation is to be fruitful, you must have trust in me. For these reasons, I ask your permission. May I discuss your sessions with Lily?”

She stared at me once more. It wasn’t a glare this time, though. It was more like she was sizing me up, trying to figure out if she could trust me.

In the end, I guess she decided she could. “Fine. You can… talk about it.” She swallowed visibly, already dreading the conversation that was about to occur.

“Thank you.” Our conversation completed, I rose to fetch Lily. “Lily?” I asked, peeking into the bedroom. I found her staring at my cloud bed. ‘Shit, that was an oversight.’

“Is this… where you two…?” She raised a hoof to wipe tears from her eyes.

I took a deep breath. “We’ll… get to that.”

“Okay…” She showed no signs of moving from the bedroom. “You know… I agreed to this… little therapy session you’re giving us, but… I’m still mad… at both of you.” She looked up at me, her expression matter-of-fact. “I know… that it’s your job to keep things secret. I know that, but…” She looked through her mind for the right words. “… But that doesn’t make me feel any less betrayed, Guilty. I considered you a friend, and you kept this from me. And even though you didn’t know me when this started… and even though it’s your job to be discreet… and even though I recognize that this was an impossible situation for you, none of that keeps me from being mad at you. I just… want you to know that. I’m going to do my best to stay level-headed, but…” She forced a smile. “Well… I’m going to do my best.”

“That’s okay. I’m not going to pretend that my profession makes me somehow exempt from that anger. You have every right to be upset.” ‘Now, let’s hope she can be angry and civil at the same time.’

She nodded. “Shall we, then?”

“Yes, it’s about time we begin.”

So the two of us sat down with Carrot Top, and couple’s therapy was in session. “So without further ado, let’s start. The first thing I want you both to do is simple. I just want you to honestly tell each other how you feel. Just remember the rules. Would either of you like to go first?”

“I would,” said Lily. “I just feel like—”

“Don’t tell me, Lily. Tell Ms. Harvest. Again, I’m just here to make sure you to communicate effectively.”

“R-right” She turned to her lover, and continued. “I just feel like… lately you’ve been very… cold to me. I mean, we’ve never been a perfect couple. We would have our fair share of arguments, but that’s normal. Couples fight. Lately, though… it’s like we barely have conversations that aren’t arguments. It used to be that we’d have a bad day every now and again, but now… it’s like the good days are a… a commodity… a rarity. It’s like the days when we aren’t fighting are breaks from my otherwise … miserable… life.” She began to cry. “I’m s-sad, Goldy. I’m just… sad so m-much of the time. I’ve been trying and t-trying and trying to be happy, and to make you happy, but… I’m kind of ready to… give up. It’s like… It’s like I don’t even want to try anymore.”

She took a deep breath. “And this was before you told me about you and Guilty. When I found out that you were being… intimate… with somepony else I… I just about lost it.” She swallowed hard. “Because I had been trying so hard to make… us… work, and you had just… found somepony else already. I mean… it made sense… the distance, the silence, the… everything. Of course you had found somepony else to… to share yourself. It explained everything.”

“Lily, that’s not—”

“Ms. Harvest, let her finish,” I chastised, earning myself a glare.

Lily once again dove into her hooves. “It just felt like… you’d… given up on me.”

“Lily, I never—”

“Ms. Harvest…” I intoned once again.

“No, I’m… I’m done. I need a moment.” Lily wiped tears from her eyes and looked up at Carrot Top. “Your turn, I guess.”

Carrot Top looked to me, half out of confirmation, and half out of desperation. She just needed a little push. “Ms. Harvest, is there anything you’d like to say in response? Or anything you’d like to bring up?”

“I…” She swallowed. “I…” she repeated. She opened her mouth a third time, but no sound came. The poor mare had stage fright.

“Don’t you have anything to say?” pleaded Lily.

“Lily, please. She’s trying.”

Carrot Top’s hooves rapped nervously against my table. “I… It’s really hard.”

I raised an eyebrow. “What’s hard?”

“To… to just talk like this. To talk about… this kind of thing. It’s… It’s really hard for me.”

“‘This kind of thing?’”

“Like… Like… emotions.” She turned back to Lily. “I don’t… I don’t know how to talk about it like you do. You’ve… You’ve got all these words for emotions. Betrayed. Devastated. Morose. Ennui. You use them all the time. But I… I don’t know how to do that. I don’t know how to turn a feeling into a word. I can figure out ‘good’ and ‘bad’ but… beyond that… I don’t know how to explain it. I feel shitty about a lot of what I’ve done. I feel… really really awkward right now.” She shrugged. “That’s about the best I can do.”

Carrot Top was beginning to shake. This was visibly difficult for her. “So… I’m sorry, if sometimes it feels like I’m not… communicating. But it’s never because… because I don’t want to. It’s because I don’t know how. And… and I know we’ve been fighting a lot, and… and I’m sorry. I can tell it’s my fault, I… I’ve been… out of it lately.”

Lily wanted to speak up, but restrained herself.

“And as for… Guilty…” she bit her lip. “I’m… I’m really sorry about that, too.”

“You think you can just apologize—!?”

“Lily, please. Yelling.”

Lily begrudgingly silenced herself. She was beginning to lose her cool.

“I… I don’t know what else you want me to say, Lily. I don’t know what else to do beyond say I’m sorry. I don’t know how else I can… fix this situation. You want something from me, I know that much, but… but I don’t know what that is.” Now Carrot Top was beginning to sob. “What am I supposed to say?”

Lily sighed. “I don’t know either.”

Before silence could set in, I kept the conversation moving. “Okay. That was very honest of both of you. Now, there’s a few important things I’d like to address, if that’s alright. Now, the first is something you two mentioned. Now, Ms. Harvest, you said you’ve been ‘out of it’ and Lily said that you’ve been in a bad mood lately. How long has this been going on? Did… something happen?” ‘Pick your battles carefully, Guilty. You’ve only got so long before the both of them are fed up with each other. Are you sure this is worth talking about? I pondered. If nothing else, I might be able to get Carrot Top to admit something personal again. The more she does it the easier it will become.

Lily was, of course, the one to respond. “I… must’ve asked her a hundred times what was wrong. I never got a straight answer.”

‘Let’s give it a shot.’ “Well, Ms. Harvest, I think now would be a good chance to talk about that, if you like.” ‘Careful, don’t push too hard.’

“I can’t,” she quickly responded. It was interesting. It wasn’t a nervous “I can’t.” It was direct… matter of fact. Not a “please don’t make me.” More of a “Circumstances prevent me from discussing it.”

“Why can’t you?” I inquired.

“I just... I just don’t want to,” she explained.

“That’s a lie.” Both Lily and Carrot Top gave a surprised look. “I mean, it’s true, but it’s not all true. There’s another reason you can’t talk about it.” This time they shot confused looks at each other. “I’m not wrong. You are lying. That is a fact.”

Carrot Top began to protest. “You… you can’t just know—”

“I can and do. You’re a good liar, don’t get me wrong, but you have a tell. It’s in your brow. Don’t worry about it. The fact remains, that was a lie. Or a half-truth, I suppose.” I did not break eye-contact for a moment. They could tell I was being perfectly serious. “So please… once again. Why can’t you talk about it?” ‘Dangerous territory, Guilty. Very dangerous. Don’t let your own curiosity ruin this session. I hope you know what you’re doing.’

Lily remained speechless while Carrot Top wrestled with her tongue. “Y-you… How do you...? RRRRGH!” She shook her hooves in anger. “Isn’t this breaking your own rule? Aren’t you antagonizing me right now?”

‘She’s right. Quick! Evade the question!’ “Ms. Harvest… I can’t make you talk about it. I won’t make you talk about this. But… you really should. You need to be open about this kind of thing.” I sighed. “I think it’s painfully obvious that while you two have many many small problems… you also have one big one. And that is a lack of communication.” Lily nodded in agreement. “You might not want to hear this, but no relationship lasts long without it. If you don’t start communicating…” I trailed off, nothing more needed to be said.

“No… no I can’t… I just can’t.” She shook her head

‘Probe. Delicately.’ “But, why? Is it about Lily?”

She shook her head.

“Is… it about me?”

She did nothing.

“So it’s about me.” Searched my memory. It didn’t take long to figure out what had occurred to put Carrot Top in a sour mood. “This is because Derpy introduced us?” The times seemed to match up.

She nodded.

“Wait,” Lily interjected. “What do you mean she introduced you. You’d said you’d been doing this for over a year, right? How did you get ‘introduced’? You’ve only been… out of it… for a couple months at the most.”

“That… will require some explanation.” I cleared my throat. “I have asked Ms. Harvest if I may… discuss everything that has occurred between us, and she agreed.” I could see Carrot Top bracing herself. “Do you… still want to hear about it?”

Lily looked unsure. “Oh, um...” Her brashness earlier was coming back to bite her. “… I mean… I know earlier I was saying… but…”

“We don’t have to discuss the… session itself. But… the context might be necessary.” I worried if I was overstepping my bounds. Was I forcing the direction of the conversation? ‘In the end, this needs to be discussed. Doesn’t it?’

Lily gave a conflicted nod. “O… okay.”

I took a breath. “So… Ms. Harvest first approached me, like you said, over a year ago.” I could see the mare in question writhe in torment. She wanted to curl into a ball and disappear. “She… never gave her name. She offered only a pseudonym. ‘Carrot Top,’ I was to call her. We never really spoke, she would arrive, get what she came for, and leave. So for the better part of our… acquaintanceship… we’d never truly… met.”

“That changed one day during market. I was buying carrots from… some client whose name I didn’t know… and Derpy spotted me. She ran up, said hello, and introduced me to her best friend… my client… Golden Harvest.”

Lily turned to Carrot Top. “You… you had him call you that? Why?”

“I… I don’t know,” she responded.

“Is there some significance to that name?”

“It’s… it’s a name some girls used to tease her with. She hates that name.”

“Well, regardless, I believe we have found the source of your foul mood. My… inclusion in your life has been stressful for you, it seems.” I put on a frown. “I’m so sorry. I guess, I’m even more to blame than before.” A false apology. Carrot Top’s actions were her own; I did not force her to react as she did. Either way, I was still the villain in Lily’s eyes, and little bits of sympathy add up.

It occurs to me that that might be considered a shitty way of thinking about this situation.

Well… old habits die hard.

“It’s… It’s okay, Guilty. That’s not on you,” Lily said.

See? That shit works.

Carrot Top finally spoke up. She managed to force herself through a proper apology. “I’m… I’m sorry Lily. I’m so sorry. I just kept… worrying that you were going to find out and… and it kept bringing up memories and… and I’m sorry.”

There was a pause. The silence was almost tangible as Lily and I shared a look. I could see the same thought behind her eyes that was behind mine.

‘Memories?’

Lily tentatively asked the question that was on both of our minds. I was happy she did; I’d dictated the flow of this conversation far too much already.

“Goldy? What do you mean… memories?”

In an instant her apologetic visage was gone, replaced by a nearly perfect poker face. “Nothing.” It was that same tone. That direct, matter of fact tone. It came so natural to her. It was a lie she was used to telling. An old secret. Some fundamental secret that’s been a part of her life for a very long time.

“No, you said it brought up memories, what did you mean?” Lily persisted. I’d mostly stopped paying attention. My mind was racing. ‘I bring up old memories for Carrot Top. No. Not just me, it happened after she found out that Derpy was a client.’

Carrot Top began to panic. “I… I didn’t mean anything. Can we drop this?” ‘Something about the fact that Derpy was a client. Has Derpy even been strung along by somepony before? Am I reminding her about that? She mentioned something like that I think.’

“Goldy… you were trying to communicate right? I know you say it’s hard for you, so… so I’m trying to be more receptive, here.” ‘It’s plausible. But why would that be a secret for Goldy? Come on, Guilty. You’re missing something.’

“I… I wasn’t. I don’t… I don’t want to… Can we please not do this?” ‘It involves Derpy. It’s a secret. Maybe it’s a secret from Derpy. What do we know about their relationship? If there’s a secret between two friends, it will somehow affect their dynamic. Carrot Top’s overprotective of Derpy. Says she’s too trusting. That would make sense, if Carrot Top herself was keeping something from her. Too trusting would include Carrot Top.’

“I’m… I’m sorry, dear. I’m just… trying to help.” ‘Okay, we’ve got a working theory. Now, how do I factor into this? How does me being with Derpy bring up memories? It must somehow involve somepony else that Derpy’s been… with… oh…’

“No you weren’t, Lily. You were just trying to pry… you always do this!” I didn’t even notice that Carrot Top was beginning to yell. I was too busy being shocked by my own revelation.

“She slept with Dusty,” I said to myself. ‘You fool! That was out loud!’

Carrot Top’s head spun around with nearly violent force. Her mouth was agape, her pupils pinpricks. “Y-y-you…” ‘Bullseye, it would seem.’

There’s this moment when a pony’s secret is discovered. It’s a moment of pure and incomparable terror. It happens right after their secret comes to light, and right before they know how everypony is going to react. In that moment, their brain is assuming the worst. They’re imagining every possible bad scenario that possibly occur, and it’s terrifying.

That pure and unfiltered terror was evident on Carrot Top’s face. She was petrified. Frozen with fear. This moment was physically affecting her. She was about to start hyperventilating. Were this not a session, I might have allowed her to suffer for a bit.

“Really?” I made sure to keep anger or judgment out of my tone. After all, I was certainly in no place to judge her. I mean, it made sense but it was still… kind of shocking.

“I… I…” She was still waiting for the other hoof to drop.

“Goldy… I… I don’t believe it.” Lily could only place a hoof in front of her mouth in shock. “I just don’t believe it. When? How?” To her credit, Lily didn’t seem mad either. She was, however, completely flabbergasted.

“It…” She took a deep breath. “Years ago…” she trembled as she spoke. It’s curious, but in the end, ponies want to tell their secrets. They want freedom from the weight in their stomach that comes with keeping something hidden inside of them. Carrot Top had probably envisioned this moment a hundred times. Practiced it. Dwelled on it.

I was probably never present in her simulations.

“It was at a… a Hearth’s Warming p-party I threw. Dinky was still just a b-baby. Derpy h-had to leave early to let the sitter go home and… and we were drunk and… Dusty and I kept talking and… and before I realized it e-everypony had left except for him, and…” Carrot Top began to hyperventilate. “And… and… and… it just kind of… happened!”

‘Sympathize. She needs to calm down.’ “That… must’ve been a very painful secret to keep.” ‘Not your best work.’

“How… how could you keep that from Derpy?” Lily was still trying to wrap her head around the situation. Still, the shock was beginning to wear off.

Carrot Top rubbed the tears from her eyes. “W-w-we were going to tell her. We really were. W-we both decided to just come clean, but then… then…” Her voice squeaked in anguish. “… he died.” She paused as the situation began to sink in. “And I couldn’t… I just... I couldn’t let Derpy remember him like that. I couldn’t… I couldn’t do that to her.” She swallowed. “So… so I didn’t say anything. I just… I couldn’t. I still can’t.” She gave us both a desperate look. “She can’t find out about this, you two. It would just… it would destroy her.”

My response was automatic. “I won’t be saying anything. This is a session. Your privacy is guaranteed.”

Lily, on the other hoof, had a less… favorable response. “Oh my gosh, Goldy… I’m having lunch with her tomorrow. How… how do you expect me to look at her?” She gagged briefly. “I think I might be sick.”

“I know… I know… It’s just… I’m so awful.” Carrot Top was now openly bawling. “I’m… I’m just such a bad friend.” She buried her face deeper into her hooves than ever before as long overdue tears were finally let loose.

I pondered. ‘Do I comfort her or do I let her cry?’ As I wrestled with my dilemma, Lily found her own answer.

A gentle pink hoof found its way into Carrot Top’s mane. “It’s… it’s okay, dear.”

In an instant Carrot Top threw herself at Lily, wrapping her arms around her. After a moment of shock, Lily returned her hug as she wept into her lover’s shoulder. “I’m… I’m sorry . I’m so sorry! I kept so much from you and I’m sorry!”

Several minutes passed while Carrot Top bawled and screamed and cried into Lily’s welcoming shoulder. She needed this cry, and I wasn’t about to interrupt it. Lily’s anger was seemingly forgotten as she stroked the puffy orange mane. Perhaps she’d realized just how much stress Carrot Top was under, or perhaps a nurturing instinct simply kicked in. Regardless, if only for the moment, the fighting had stopped. I took the opportunity to fetch the mares a glass of water. Carrot Top was going to have a ragged throat.

Carrot Top finally released Lily as I placed the water in front of her. “Thank you, Guilty. Thank you so much.” She quickly grasped at the glass with both hooves. “And I’m sorry to you too. I’m always so mean when I come here. I’m sorry I throw the money on the floor, and I’m sorry I’m always just so cold, and I’m sorry I don’t let you talk and—”

“Okay. Okay, let’s rein it in, Goldy. I think the floodgates are a little bit open, and you’re a getting overwhelmed by your own emotions.” I used my “extra-comforting” tone, for only the most dire of situations. “I want you to take a deep breath and drink some water.” I smirked. “Just not at the same time; we don’t want you choking.”

She laughed at that. “You… you called me Goldy,” she observed.

I paused for a moment. “Is… that okay?”

She nodded, before obliging my request. She inhaled long and hard before taking a deep drink of cold water. “I… I do mean it, Guilty. I… I really am sorry. It just… it made it… easier somehow. It made it easier to—”

I raised a hoof, cutting her off. “Please, Goldy, no need to explain. It’s a mentality I’m intimately familiar with. Not to mention, we should probably spare Lily. I don’t think she wants to hear about the, erm… details.”

“I… I do have one question… actually,” spoke Lily.

“Oh, um…” Carrot To— Goldy looked at me and nodded. “I think you probably deserve that.”

She turned to her lover. “Goldy… what I’m about to ask… might sound stupid. It’s something I’ve… I’ve been worrying about. With everything that’s happened here, I… I find myself actually worrying more than before.”

My brow furrowed. ‘Well, that’s the opposite of the desired result.’

“Goldy… do you… do you wish I was a stallion?”

‘Okay… that’s a valid concern given what’s come to light.’

“I mean… when you told me about Guilty… that’s the first place my mind went. I mean… it’s not as though we’d never…” A blush crept onto her face. “… you know. But… some part of me always felt like… like you didn’t enjoy… that… with me. You always said you did, but… but some part of me didn’t believe you. I always chalked it up to my own paranoia, but now Guilty… and Dusty… I just.. I have to ask this stupid stupid question.” She fiddled with her hooves as she mustered her courage. “Golden Harvest, are you… straight?”

“What?” I scanned Goldy’s features. Minor traces of worry, but no guilt. This was not one of Goldy’s many secrets, it seemed. “No… Lily, I love you.”

“I know you love me, Goldy. I just worry that… you don’t love being with me.” Her head fell.

That latent worry I’d spotted came back threefold. “W-well…” It seemed that Goldy had been telling so much truth, she’d briefly forgotten how to lie.

Lily just shook her head. “I knew it. I knew it.” She stood up and began to pace. “The signs have always been there. Derpy always said you never really showed interest in girls.” Lily had apparently taken it upon herself to make sure that drama could not leave the conversation.

“Lily, it’s not that. It’s…” She cast a worried glance in my direction. I forced myself not to roll my eyes. Of all the ponies to be shy around, I am not one of them. “It’s… well… don’t be mad?”

Lily stood firm. “I make no promises.”

Goldy’s Ears shot back. “Well… I… I like being… f-f-filled. And when we’re… you know… you never… you never use the… the… thing I bought.”

Lily’s head cocked to the side. “What thing?”

“The… the v…. vibrator. Remember?” Goldy was now a bright tomato red. “I bought it for you to… to … use… on me. But… you never do.” She steeled herself. A sort of courage began to build within her. “And… and while we’re on the subject, you… you never do much of anything for me in bed. You’re kind of… selfish. You let me get you off, and then you just kind of… stop. You never really... reciprocate.”

Can’t say I was expecting that.

Lily looked positively mortified. “I…”

“And… and I didn’t want to say anything, because… because whenever I asked for something in bed, you always seemed to… take it personally. And… and Lily, I needed… release. And so…” Her gaze fell. “… so I started visiting Guilty.”

Silence hung.

Goldy was the one to break it. “I… I think you’re right, Guilty… I think my… floodgates are kind of open.” She laughed nervously. “… I’m sorry, Lily.”

Lily looked as though she’d seen a ghost. “I… I just… I never.” Her face began to turn red. “I never thought... I guess I never thought that… that you were anything but satisfied.”

“How could I be satisfied, Lily? You never touch me. I’m the only one doing anything.” She pounded her hoof against the table.

Calming tone. “Okay, Goldy. You’ve made your point. Lily feels bad already, no need to rub salt in the wound.” ‘Not to mention, you’re beginning to lose your temper.’

Lily struggled in vain to find her voice. “I… I’m… I…”

‘Help her, she’s drowning. How to handle? Private conversation? No, we already did one of those today. What’s a good angle? Generic sympathy will have to do.’

Comforting tone. “That’s… not an easy thing to hear, is it?”

Lily simply shook her head.

“As you might suspect… I’ve heard this a lot from couples that come in.”

“What do you tell them?” she asked, half out of desperation.

“That… trouble is the bedroom is just another obstacle to overcome. That there are worse problems to have. That sex is by no means the most important part of a relationship. And most importantly that… it’s never too late to start learning how to please your partner.”

“Mm-hmm…” Lily nodded.

‘Do we opt for confidence boost? Maybe we try to bring her in for sexual coaching. Hmmm… too many moves, I need to feel this out.’ “So, let me ask you something, Lily. Now that Goldy’s said that, how do you feel about your… performance in the bedroom?”

“I… I’m not sure. I always felt like she enjoyed it, but… but maybe… maybe I have been selfish. I’m trying to think of the last time, I… I actually did something… proactive, and… and I… can’t.” She looked Goldy in the eyes. “I… I guess I feel... ashamed that I’ve been… neglecting you. But at the same time… I suppose I just think about… you know… sex… differently than you.”

Goldy furrowed her brow. “How do you mean?”

“Well I guess… I guess it’s hard to explain. I mean to me… the most important part about… about being with you is just that. It’s the closeness, the... intimacy. I mean… it’s fun to… you know…” Shyness continued to hinder her speech. “… orgasm, but that comes second to… just feeling like you’re close to me. I mean, sometimes I don’t… finish, and… and I honestly don’t mind. I guess… I never thought that you would mind either.”

Goldy was confused. She seemed not to understand the concept of ‘not needing to climax.’ “Well… well now I feel bad.”

“You don’t have to feel bad about your desires, Goldy. Neither do you, Lily.” The mares both looked at me. By now they were ragged with fatigue. Emoting so much takes a toll on a pony. They, and I, were ready to end this session. “You both have very different needs. Physically. Emotionally. There’s nothing wrong with that. However, you both really need to work on —as I’ve said — communication. Goldy… you need to be more vocal about… well a lot.”

She nodded solemnly.

“Lily… I feel you need to be a bit more patient with Goldy. I think we’ve established that being open is a challenge for her.”

Lily nodded in turn.

“So… how are we feeling?”

“Overwhelmed,” responded Lily. Goldy nodded in agreement. “I mean I guess… I guess I’m not as mad as I was. I don’t know if I forgive either of you yet.” She looked me dead in the eye. “That said… I really have to thank you, Guilty. When I came here I was… I was ready to… to leave Goldy. Now I… I feel like I’ve got a… better understanding of… well of myself… of Goldy… of a lot of things.” She looked at Goldy. “I… I love you, Golden Harvest. No matter how mad I was this morning, I was never so mad that I stopped loving you. I… I want to work on our relationship. I don’t want to lose you.”

“I don’t want to lose you, either.”

“But… I need to lay down some ground rules. You’re not exactly out of the dog house yet.”

Goldy gulped. “O-okay.”

“No secrets. No lies. No matter how small, no matter how innocent, none whatsoever. I.. I can’t deal with it anymore. Also…” She glanced at my apologetically. “… no more seeing Guilty. I mean… you can still see him in town and stuff, but… but you can’t keep having sex with him. I just… I need that from you.”

No hesitation from Goldy. “Of course.”

“Promise me!” Lily insisted.

“I promise.”

“…Okay.”

“Can I ask for something then?”

“I… suppose.”

“Can you… can you try to give me… a little more slack in a conversation? I… I try really hard to… to share, to be open. When you keep… hounding me for a response… it makes it hard to… to talk to you. I want to be open, Lily, but… but you have to let me.”

“I will… make an effort.”

“And Guilty? I’m… I’m sorry you got caught up in this. And… and thank you. I… I don’t really deserve what you did for us today, not after the way I treated you, so… so thank you. You really… really didn’t have to do this.”

I could only smile. “You’re welcome. Both of you.” ‘Thank Luna, this is finally coming to an end.’

“So, I suppose we should go,” said Lily.

I looked at the clock. It was about that time. “Well… if the two of you ever want to come in… together I mean… my door is open.”

They nodded, and rose to leave. ‘Oh shit, do I have to be this guy right now?’ “Um… Ms. Harvest?”

Goldy sensed the unease in my tone. She looked confused.

I sighed, and held out an empty hoof. A poor sad hoof, with no money in it, just begging to be filled.

“Oh… right… right.” She produced a small bag of bits and hoofed it to me… like a decent pony.

“This will be fine today, but just so you know… I normally double the price for two mares. That’s forty an hour.”

“Good Heavens!” cried Lily, as she brought a hoof to her chest.

I chuckled. “I don’t come cheap, Lily.”

“Clearly.” She turned to Goldy. “Shall we?”

Goldy nodded. With a quick goodbye, the two left my home. I considered the session a success; the couple left on speaking terms, willing to work on their relationship. Sometimes all it takes is one calm conversation to prevent a potential breakup.

It would also appear that I’ve lost a client. No great loss, I never cared for her sessions all that much, anyways. Still… it will be nice to not have to cringe whenever Carrot Top walks by. Because, there is no Carrot Top, only Goldy.

*sigh*

I really hope they work it out. Their mood affects Derpy’s, which in turn affects mine. My life is made easier by their improved relationship. That hour of work will doubtlessly pay for itself… not to mention it was actually paid for. Overall, a very successful afternoon.

It would appear that I am determined to be a pragmatist.

Who am I kidding? I like helping ponies. I just also like making money.

Still, after they left, I was left with plenty of time to contemplate my latest plight. I had a secret to keep from Derpy… a big one. There was no ambiguity with this situation. I cannot tell Derpy about Dusty, much as I may want to. It was protected by the iron-clad rule of the session.

But… this will be harder than other secrets. This is something I truly wish I didn’t know.

I don’t want to think about this right now. I should get to bed.

Author's Note

This has been a planned turn of events since I wrote Chapter 7. I've been trying very hard to get to this point, but there was so much set-up to do.

I'm quite pleased with this chapter, and I do hope you enjoyed the antics of the angry couple. It was very fun to write.

Once again, thanks to coandco, aquapunkchick, Jake the Army Guy, and Blackskulls for sanding down the edges of my fic.

Changes of Role

Chapter 23

Changes of Role

I’ve noticed that my schedule has been undergoing a slow change over the past few weeks. I find myself spending more and more time with Derpy. Any free evening, any day off, any time we can find, we seem to spend together. We do all kinds of stuff: dinner, shopping, Lyra’s Hearth’s Warming Party.

On a side note, Goldy and Lily were there. I hadn’t seen them since that session; they appeared to be doing better. Derpy’s also been saying that they’re on better terms. If nothing else, they seem to have stabilized. At the party Lily told me that she’d be moving in soon. Truth be told, I feel like things are going a little too well on that front. My inner skeptic is still worried that that’s going to blow up in my face somehow.

Three days ago, however, I was not concerned with the inner workings of lesbian relationships. I was concerned with something else entirely.

“Are you sure this is okay?” I asked Derpy for what was likely the third time. We continued along the dirt path out of town.

She rolled her eyes. “Yes, Guilty. I asked her at market yesterday; she said to stop by any time. Besides, I wanna see this thing.”

“But are you sure it’s okay if I go with you? Did you mention that you were bringing ‘the whore’ with you?”

She gave an annoyed sigh. I was worrying too much again. This has become part of our dynamic. I worry, she reassures. “Fluttershy’s not like that. Besides, didn’t you say that you were on her good side after you rescued this thing?”

I took a breath to calm myself. “Well, yes, but... I don’t like to show up unannounced like this. Ponies don’t react well when I… jump up on them.”

“Relax, Guilty, you’re not ‘jumping up’ on her. I said I’d be bringing a friend,” she attempted to reassure me.

“But did you say that it was me?” Clarification is important.

She shrugged. “I don’t think I had to. Everypony pretty much knows we’re dating at this point. She probably knew I meant you.”

“I’d feel a lot better if that last sentence didn’t have a ‘probably’ in it. Just saying.”

She sighed and placed a wing over me. “Guilty, relax. If it’s an issue, we’ll deal with it.”

I leaned into her. “Okay.” I didn’t really feel better, but I felt I’d bothered Derpy enough. I was mostly worried that Fluttershy, fragile creature that she is, might not be able to handle the shock of seeing the escort she halfway-propositioned. She might blush herself to death.

In all seriousness, I was worried she’d have a panic attack at the sight of me.

As we approached the cottage, my eyes went wide. Fluttershy’s home was damn near alive. There were birds and critters everywhere. Beavers and doves and lizards and just... fucking every animal. All the creatures were darting around the cottage in the center of the plot. It had an actual grass roof. It’s not a small place, either. I think it’s a little bigger than my place.

We walked across an actual moat and Derpy knocked on the door.

“Just a second,” came Fluttershy’s delicate voice. Moments later, the door opened to reveal the lovely young Pegasus. “Oh, hello Derpy. Hello… G—” Her eyes shot wide as she realized who I was. Called it. “Oh, my… h-hello M-Mister Pleasure. Um… h-how are you this fine day?” I could sense Derpy fighting back a groan. This wasn’t the first time somepony had been awkward around me, and Derpy was beginning to get sick of it.

“I’m fine, Fluttershy. Derpy said we could see the ray today?” A good way to deal with awkward is just to keep the conversation moving.

“Oh… of course, right… that’s why you’re here.” She seemed relieved. “Just let me put on a coat.” She disappeared briefly once again.

“Okay, you were right, Fluttershy kinda panicked,” admitted Derpy. “But it wasn’t that big a deal.” She leaned into me once more.

“Yeah, you’re right. Just a hiccup.” I leaned back.

Fluttershy reemerged, donning a coat and scarf. “He’s just around back. Follow me.” The back of Fluttershy’s house was even more impressive than the front. Chicken coops, pig pens, houses for every kind of animal conceivable— life littered this place.

We, however, were led to a strange looking structure. A dome made of tarpaulin and wooden beams. “What is that thing?” asked Derpy. “He lives in here?”

“Oh… yes… Twilight helped me build it. It’s based on something called a ‘sweat lodge’ that the Buffalo build. It keeps it very warm in there.” She gently knocked on the… tarp. “Poncho? You have some visitors. That nice pony that saved you is here.”

A massive body of grey burst through the flap before swerving into the sky. Derpy jumped back about a yard, wings ready to take flight. The ray began to circle overhead, analyzing his guests, or so it seemed.

“You named it Poncho?” I asked.

Fluttershy giggled. “Actually, Pinkie Pie named him.” The ray began to descend slowly, floating impossibly in the air. He delicately landed on my back. Even through my thick jacket, I could feel his warmth. Derpy watched in amazement as the beast levitated daintily. “I think he remembers you. He never really warms up to new ponies,” said Fluttershy.

“I think he’s a bit bigger, too.”

“Yes, he’s still a growing boy.” She sauntered over and petted him. “My, aren’t you affectionate today?” I could feel his little horn doo-dads kind of wrap around my neck.

“HE’S SO COOL!” shouted Derpy as she ran towards me. “He hovers, Guilty! He HOVERS!”

“Oh? Last time you saw them you were afraid of them.”

“That’s not fair, there were a thousand of them, and I didn’t know what they were. AND, I thought they were gonna eat me.” She eagerly reached out and petted the ray. “What does he eat anyways?” she asked Fluttershy.

“Oh… he’s a filter feeder, he eats ash and dust in the air. He doesn’t go hungry, as long as there’s a burning fire.” Fluttershy blushed. Even if all eyes were on Poncho, Fluttershy felt on the spot. Still, she smiled, happy to talk about the ray.

“I wonder if he’ll fly with me,” said Derpy. “Lemme see. If I…” With a single flap Derpy shot into the air. The ray quickly shot off my back to follow. “Woo-hoo!” Derpy called from above.

Fluttershy smiled as she watched Derpy and the ray soar off. “Rainbow Dash did that, too. It’s because Mantle Rays swim in schools. His instincts tell him to follow what’s moving.”

“You really like animals, huh?” I gave her a charming smile. One can always take the time to plant a seed of seduction.

Fluttershy blushed up to her ears. “Oh… I… um… yes.” She stared down at the snow beneath us. Her hooves absently twirling through the slush. She looked as though she was about to say something.

‘Is she trying to work up the courage to ask for a session?’ I examined her movements. Twice she almost moved to speak. She evaded eye contact. Whatever it was, she had something to say. ‘If I don’t make a move she never will. Ask her? No she’ll deny it. Tell her.’

“Fluttershy?”

She looked up in surprise. “Y-yes?” She was so nervous, scared even. Afraid of judgment. She needn’t worry about that from me.

“There’s something you want to ask me, isn’t there?”

Her eyes shot wide. “Oh, umm… no no… nothing at all.” A hoof nervously shot to her pocket. I heard the crinkle of paper.

‘She talked about letters last time you talked to her.’

“Is that a letter for me?”

“Oh, um…” Reluctantly, she revealed a letter. “…Umm… I…”

‘Help her, Guilty, she’s drowning.’ I raised a hoof. No words, just an open hoof. Taking my invitation, she quickly placed the envelope into my grasp. It was a worn thing. Written ages ago. It even had a stamp. She never worked up the nerve to send it.

I just smiled and pocketed it. ‘Hopefully the letter isn’t for a specific date. Oh, this is going to be awkward if it’s addressed for the past. Oh well, I can always write her back if that’s the case. At least now the conversation has been started.’

“S-sorry,” she mumbled.

Reassuring grin. “Don’t apologize. You’ve done nothing wrong.”

She peeked out from behind her mane. “O-okay.”

Above our head, Derpy enjoyed her flight with the majestic creature. It followed close behind her, matching her every move. “That thing’s gotten much healthier.”

“Oh yes, he’s come a long way since you found him. Still, he can’t get very far in this cold. He’ll have to wait till summer before he can go anywhere. Not to mention, Twilight says no one knows where all the Mantle Rays went. They’ve dropped off the face of Equestria.” A sad look graced her face. “I hope he finds his family again.”

Reassuring smile. “I’m sure he will.”

She smiled back shyly. Moments later, a streak of grey rocketed past us back into the tarp structure. “Oh dear, looks like he’s cold again. He doesn’t last too long outside in this weather.” And like that the ray had vanished, back inside his little dome.

Derpy landed beside us. “Yeah, he started slowing down after a bit. Still it was super fun. He’s so fast, Guilty.”

“Yeah, I remember from that day they were chasing you.” I stuck my tongue out at her.

“Ugh… I’m never gonna live that down, am I?”

“Nope.”

“Jerk.”

“That’s me.”

Derpy smiled and gave me a punch in the arm.

Fluttershy laughed at our antics, before stifling herself. “S-sorry, I didn’t mean to laugh.”

I shook my head. “It’s fine. We should probably get out of your hair. Thanks for having us.”

Derpy agreed. “Yeah, it was awesome. Thanks again, Fluttershy.”

“Of course. No problem.”

We waved goodbye and made our way back to town. I find that now, we walk so close together, usually with me under a wing. We’ve become so… coupley.

And wouldn’t you know it, just as we were leaving Fluttershy’s, somepony was there to bear witness to our coupley shenanigans.

Or rather, somezebra.

“Guilty and the mail mare, I almost didn’t see you there,” Zecora sang. She walked up the path along with her cart.

“Oh… Hi Zecora! You know Guilty?” asked Derpy.

“You are surprised at such a notion? Where did you think he got his potions?”

“Oooooooh,” responded Derpy.

“And that reminds me, Mr. Pleasure. I have for you quite a treasure.” From her cart she quickly produced a small white vial wrapped in a scroll. “I did promise you a gift, for my… burden you did lift.” She hoofed me the phial.

“Oh… thank you… I’d forgotten all about that.”

“It was not an easy brew, it took some time to make for you. There are instructions on the scroll. Now please, continue with your stroll. I have potions to sell to the mare that here dwells.”

“Oh… okay then…” I stared confused at the potion that had been thrust into my hoof.

“Bye, Zecora!” cried Derpy.

She waved goodbye as we walked past.

“Well, that was a fun little encounter.”

“Yeah, I haven’t talked to her in forever. I bought a cream from her a long time ago for a rash I got. It helped so much. I made her muffins as thanks.”

“Sounds like you,” I snarked.

“Shut up!” she shouted in mock hurt. “That was so much fun, Guilty! The ray was pretty cute up close, even if you can kinda see his ribs through his mouth. That part was actually pretty creepy.”

I nuzzled her slightly. “Well, it’s certainly an upgrade from before. When I found him he was covered in blood and dirt.”

“Aaaw,” Derpy responded. “He seems pretty healthy now. I mean, I’m not an expert or anything, but he was pretty lively.”

“Yeah, he was.”

“Well, I’m glad we did this. I’ve been wanting to see that thing forever.”

“Me, too. I kinda wanted to check in... see how the little guy was doing.”

Derpy nuzzled me aggressively. “Aaaww, Guilty cares about the little ray he saved.”

“Yeah well… I kinda feel responsible.” I leaned into her affectionate nuzzle. Our dynamic has changed… well... a lot in these past few weeks. We’re always so… close. I mean physically. We just sort of hang off of each other without even meaning to. It just sort of… comes naturally. We’ve been friends for so long. Now that we’re something more it’s… weird that it’s so easy.

Maybe… we’ve both wanted this for a long time. Maybe below the surface this is something we’ve wanted for longer than we knew. Then again, maybe it’s just because we know each other so well. It might just be that our relationship as it was wasn’t so far off from a romantic one. Further still, there’s always the notion that we’re just good for each other. Maybe we’re… just a perfect fit.

Whatever the case it’s still a little... scary, being in a relationship. This is all new territory for me, and I’m constantly worried I’m going to screw it up. So much of it comes so natural, but even more is so foreign. I’ve never had any trouble treating mares right. I know how to go out on a date, I know how to keep a mare entertained and interested. I know how to be a good partner… in bed or otherwise.

But I’ve never had a relationship that was… give and take. I find myself trying too hard, trying to always be the good boyfriend. However, in doing so, I deprive Derpy of the opportunity to be a good girlfriend.

We fight about that sometimes.

And fighting is new. I never fought with Derpy before; our relationship was too simple for it. But now… we fight sometimes… and it honestly freaks me out. I didn’t know I could get so mad at Derpy. Hell, I didn’t know I could get so mad at anyone.

But still, for all the weirdness and all the fighting... I really love being with Derpy. Now that I’m with her, the time we spend together is… so much more special than it was before. She was always my favorite client, but now… now It’s almost like I have… a whole new level of happiness that I didn’t know existed. A heretofore unknown elation.

I’m beginning to appreciate Crook’s attitude towards dating. He always had a girlfriend or two, and I always used to wonder why he bothered.

But now I get it. I get how it feels to be… well… loved.

At least, I assume I am.

We haven’t… said it or anything.

Not… not that we have to just yet. It hasn’t even been a month yet.

Now I’m worrying again.

Moving on!

Derpy had promised to take Dinky to a movie and I had a client, so we knew it was going to be a short date. I walked her back to town, said goodbye, and made my way home. Honestly, I was eager to get home. I wanted to tear open Fluttershy’s letter. There is often fun to be had with a new client.

The letter was positively covered in eraser marks. The nervous mare must’ve spent hours poring over this letter, because she seems to have second guessed every word on this paper alone. No telling how many sheets she went through attempting to get something she found acceptable.

It was… well… it was rather pathetic, full of “I’m sorrys” and “If it isn’t too much troubles”. Ultimately though, there was a date set. Friday. Not a particular Friday, just Friday. Thankfully, a free day for me. I just had to hope she would actually show up.

Fortunately for me, she did. Her quiet, first-timer knock was impressively soft. I actually almost missed it. I thought it was just my house settling.

When I opened the door, I was met with a mare hidden entirely behind her own mane. Her legs were shaking as she desperately tried to stand on her own four hooves. She seemed ready to flee at a moment’s notice. “H-hello,” she said in a voice as fragile as crystal.

‘Okay, Guilty, you are in full blown comfort-mode. This mare is about to pass out from fright.’

“My goodness, you’re shivering like crazy. Come in, come in. It’s warm inside.” I knew it wasn’t the cold making her shake, but better to seem ignorant than make her more uncomfortable.

“Th-th-thank you,” she spoke softly as she came inside.

“Have a seat. I was just about to put on some tea. Do you have a preference?”

As I took her coat I noticed she’d brought with her a small saddle bag. “No no, whatever you’re having will be fine.” She was determined not to be a bother.

‘Hmm. What’s the play? Insist she pick a tea? No that will just put her on the spot. Go with Chamomile, she doesn’t need anything else making her jittery. Just keep a level head, and an even tone. We just need to focus on not scaring her off.’ I put the kettle on, and returned to my nervous wreck of a client. ‘Reassuring speech time.’

Fluttershy’s face remained concealed behind her mane, avoiding eye contact at all cost. Yes, this was definitely the time to act. “You know Fluttershy… I can tell you’re nervous.”

“I’m sorry.” Her response was a swift as it was pathetic.

“No, Fluttershy, listen.” A single eye peeked through her part. “You don’t have anything to be nervous about.” Warm smile. Gentle tone. “The moment you walked in the door you began paying me for my time. This house, the tea… even me. It’s all yours until time is up. There’s nothing you can say or do that will make me upset. You can do whatever you like, and I won’t think any less of you for it. You’re worried something might go wrong, but… nothing can.”

“I… I guess…” Still unconvinced. Still shy.

‘This isn’t working. We need her to open up.’ I pondered for a moment. I was running through standard techniques of mine, when I realized I already had an in. ‘She likes animals. Just use that.’

“So, I was really happy to see the Ray the other day. Or, wait, I guess he has a name now.”

“Oh… yes… Pinkie named him. Oh dear, I already said that, didn’t I?” This mare couldn’t calm down if her life depended on it.

“So, I like the name. Is it because you can sort of wear him like big poncho?” I decided to just keep talking. If the conversation was dead in the middle of her comfort zone, she’d relax eventually.

She nodded. “Pinkie kept trying to put him on, but he would just fly away. I think she’s a little too energetic for him.”

“I know the feeling. I can barely keep up with her,” I said with a calculated chuckle.

“Y-yeah.” Her visage disappeared behind her mane once more.

‘Keep in animal centric, she’s too shy for anything else.’

“So, it must be interesting taking care of a magical creature like that. Do you have any other magical animals you take care of?”

“Oh, yes. There’s a Cockatrice who stops by every now and then…”

After that, Fluttershy managed to relax a little. We chatted over tea, I even got her to laugh a few times. She really is a passionate pony once you get to know her; she’s just got trouble speaking up about it. I spent a good 15 minutes getting the mare to warm up to me, more than I would’ve liked. But it was worth it. She actually answered when I asked my important question.

“So, Fluttershy. What can I do for you today?” I opted to skip the sultry I-wish-it-was-baritone.

“Oh, well… it’s… it’s kind of embarrassing.” She twiddled her hooves. “See… there’s this… what I mean is… I brought…” She took a deep breath. “One moment,” she rose, and walked to her saddle bag by the door. She returned carrying a large piece of equipment that I recognized as a polaroid camera. “G-guilty, W-w-would you t-take p-p-p-p-ictures of me.”

‘Interesting. Are they a gift for somepony special? A confidence booster of sorts? I mean, it’s certainly doable. But, what’s the motive?’

I’d done this sort of thing a couple times before. One mare wanted to give her husband a birthday present. Another just got off on having photos taken. Regardless of her reasons, I moved forward with the session. Gentle smile. Friendly tone. “Sure thing.”

She looked surprised. “R-really? That’s okay?”

“Of course.” Take camera. “But before we move forward, what kind of pictures did you have in mind?” Betray nothing. No innuendo. She’s too shy for it.

“Um… you know… p-porny pictures.” Her blush could make a tomato jealous.

I wanted to laugh at the word ‘porny’ but I stopped myself. “No problem.” Nothing but supportive and reassuring. “Do you want to start right away?”

“Oh… um… I guess so.” Her eyes searched the room. “Just right here?”

“No, we’ll use the bedroom.” Friendly smile. “Follow me.” I led Fluttershy into the “studio” as it were.

She seemed intrigued at the myriad chests and phials and bric-a-brac. “What a lovely room,” she said weakly.

“Yes, it’ll make a good studio don’t you think?”

“Oh… um… yes…” She dragged a hoof absently across my floor.

‘It’s like, the moment you make a move, she’s back to square one shyness.’ She was proving a tough nut to crack. ‘Maybe you should just take charge. She may respond well to instruction.’ I briefly considered this course of action before deciding against it. She may well comply, but she might not get what she wants. She might just acquiesce because it’s easier for her. I would have to stay gentle.

“So, how did you want to do this? I was thinking of just having you on the bed, but what do you think?” Appear eager for input, make sure she knows I want her to talk.

“Oh, um… that’s what I was thinking, too.” Not a lie. Good.

“Okay, hop on up, and we’ll get started.”

Fluttershy, now more anxious than ever, flew onto the bed with a couple beats of her wings. That said, it was a good anxious. An excited anxious. She wasn’t scared or worried; she just couldn’t believe this moment was finally happening. I’m sure she’d spent hours—perhaps even days—dwelling on this exact moment. How long had it been since she’d written that letter? How much time had she spent wanting this to happen? It was my duty to make sure that this little photo-shoot lived up to what had been built up in her head.

“So, first of all, how far… do you want these pictures to go?”

She didn’t seem sure how to answer that. “I, um… I’m not sure.”

Stay gentle. “Well… do you want them to be of… you know… your pussy?”

She blushed. “Uh-ummmm…” She swallowed hard. “M-maybe?”

“Okay, well, we can cross that bridge when we come to it, okay? If you're ever uncomfortable let me know, we’ll stop right away. Don’t let me do anything you don’t want.”

She relaxed slightly. “O-okay.”

My rules taken care of, I decided to begin our little photo shoot. “So to start, why don’t you just lie down? We’ll get a few shots of you in repose. Sound good?”

She seemed happy that I’d decided to start slow. Obliging, she lowered herself onto the bed.

As I looked through the viewfinder, I couldn’t help but frown. Her legs were curled next to her, almost desperately. Her mane once again obscured her face. I was going to have to gently pry her out of that shell. If I didn’t, she’d hardly be satisfied with the end result. These were not sexy pictures.

I took a breath. This was excruciating work. “Fluttershy, your mane is in your face.” I took a few deliberate steps toward her. “Can I get that for you?” The touch barrier is a big step for some ponies. The moment when you allow someone new to come in physical contact can be quite frightening. It’s especially true for mares, if you’ll pardon the stereotyping. As an escort, I’m something of an expert of making that transition almost seamless.

She nodded, of course, I’d asked in such an innocent way: “Let me fix your hair.” See, the question needs to be hidden inside something else. You can’t just come out and say “Hey, can I touch you?” It’s fucking creepy and weird. But, “Would you like a back rub?” That’s perfectly alright.

I moved my hoof forward slowly. I was literally avoiding sudden movements at this point. With a small brush, I revealed the mare’s frightened face. Amused smile. “Smile, Fluttershy. You’ve got a lovely smile, I’ve seen it. Now let’s show it to the camera.”

She gave a sour smile. “That’s awfully nice of you to say…”

Lo, a mare who does not realize that she’s attractive. What else is new? Thankfully, I have plenty of experience with this sort of thing. I may not be able to change her mind about herself, but I’ll at least be able to get her to open up long enough for a session. “Fluttershy, you’re a beautiful mare. I’m saying these things because they’re true. I won’t have you passing off my compliments as courtesy. I compliment you, because you’re worth complimenting.”

A small grin appeared on her face, and she nodded again. Her entire body began to relax. I stepped back again, and when I looked through the viewfinder, I found a picture worth taking.

A sultry-eyed, curvaceous, confident vixen, lounging on a cloud, stared hungrily into the camera. Where had this come from? I was just trying to get her to smile, but suddenly she took to the camera like a duck to water.

I took the shot. The photo paper slid out of the camera and onto the floor. “Wow, you’re… marvelously photogenic.”

“Oh um… thank you.” She blushed. “I actually… used to model… for a little while.”

“I believe it,” I replied instantly. She just showed up well on film, I couldn’t have been the first pony to notice. “Let’s get a few like this. It’s a good position for you.”

I snapped away at the feminine paragon in front of me. Her pose was impeccable. Her curves were accentuated, her gaze was smoldering. She was blushing, but that only made it sexy. I could not begin to fathom why she stopped modeling. After a few exposures I opted for a change of pose. “Let’s get a few from behind if that’s alright.”

Her blush amped up once more. “O-o-okay,” she said. She shifted her position, putting her rear end in center frame. She has a slim figure, but her ass is so toned. I couldn’t help but admire it. However, above that sexy well-toned ass, was a nervous face staring back at me. ‘Is she going to need a confidence boost after every shot? Well for now, let’s just get that nervous face out of frame.’

Confident smile. “Why don’t you stare off into the distance? It adds to the mystique.”

“Um… sure...” she turned her head. “Like this?” Suddenly that goddess of photography returned.

“Perfect. Don’t move.” I clicked as quickly as the Polaroid would allow.

It was exquisite. Her back-turned gaze was barely visible. It provided just a fleeting recognition of the viewer. “Yes, I know you’re there. What of it?” she seemed to say. She was an icy temptress: Cold and distant, but powerfully attractive.

I could feel myself getting worked up. I was excited. I could feel my face getting warm and my pants getting tight. I wanted her. She was an exceptional mare, and I wanted to pleasure her. To serve her. To know her physically.

I pushed my desires down. Now was not the time.

I took a deep breath to calm myself. “Let’s switch it up again. Something a little more… playful.”

“H-how do you mean?”

“Here… try this.” Breaking the touch barrier early was already bearing fruit. My hooves guided her body into a new position. I delicately moved her onto her back, hind legs up in the air. I then guided her front hooves downward, concealing her marehood.

“Oh… oh my,” she said.

“Is this okay?” Ever gentle. Ever caring. “It’s very sexy, you know?”

“O-okay,” despite her nerves, she seemed to be enjoying herself.

“Now, stick your tongue out at me.”

She wordlessly obliged. Once again, she was stunning. A naughty little mare, teasing the camera, her wonderful prize hidden cattily. Her playful grin, her dainty hooves, she was breathtakingly cute.

I took four shots of the impish Fluttershy before coming to a realization.

I had no idea how many pictures I would be able to take. “Fluttershy, how many exposures were loaded into this camera?”

She perked up. She’d sort of fallen into a trance as I’d been taking pictures. “Oh, um… thirty, I think.”

I looked down and counted the photos I’d taken, strewn across the floor. Some were beginning to develop. Ten in total. That left twenty pictures to get more and more of Fluttershy on film. I decided to accelerate my progress. “Ready to take it a step further? This will be a big one.”

“Y-yes,” she said with determination.

“Can you… move your hooves for me?”

She looked shocked. “Oh… oh, my…”

Too far. Backpedal. “You absolutely don’t have to. We can keep things a little more tame.”

“I… um… I…” She was internally debating it. I could tell she wanted to take things further, but she was scared to.

I decided to play it safe and simply waited for her to decide.

After several tense seconds, she moved the hooves covering herself. She was still being covered, but the bottoms of her lips were peeking out. She was wet, impressively so. Her juices were glistening at her entrance. She was loving this. “I-is this enough?”

“That’s fine.” I lifted the camera once again. Her face now a mask of pure desire, a perfect “come-hither.” Her whole body was screaming to be taken. She was a veritable queen of desire. I took three shots. Her nethers pulsed with each shutter snap, her lips grew redder and wetter with each picture taken. Even as her arousal began to build, her exquisite expression never faltered.

“Was… that okay?” I didn’t really need to ask, this was bliss for her.

She nodded. “What next?” Now she was eager. Too hot and bothered to be shy, it would seem.

‘Well, she’s asking. Time to get creative.’

“Why don’t we do this? Sit up and spread your hind legs, and bring your forehooves down In front of you.” She shifted her position. For an instant between poses I had an unobstructed view of her sopping pussy.

Excellence.

Once she was in position, she instinctively stuck out her tongue again. She’d gone back to her impish little character, a playful little mare wanting to tease the viewer. Two more pictures. ‘She manages to change character to match the pose without effort. Sex Goddess. Playful tease. Icy queen. She’s a natural.’

“Okay, how about this? Why don’t we get a few of you standing?”

“O-okay.” She slid off the bed. “How… how should I stand?”

“Okay so, turn away from me. Okay now… bend your… well, your ass a little more toward me. Now, turn almost away, just keep one eye on the camera. Perfect, now make a serious face. Stupendous.” She followed my instruction to the letter. Her pose was perfect, statuesque. “Now… if you’re okay with it… why don’t you… raise your tail?”

Only a moment’s hesitation. She raised her tail high, glorious marehood in full unobstructed view. It was perfect. Chubby wet little lips on display. Her icy visage. I took three pictures. She shifted slightly, and her lips parted a little bit, revealing her pink moist entrance. I took two more.

‘Ten left. Make them count.’

“So… are there any particular poses you wanted to do? Anything strike your fancy?”

“I kinda wanna… do one thing,” she admitted. She moved back to the bed. Before I could ask what she meant, she laid on her back, and reached down between her legs. Rather than covering herself, though, she spread herself wide, exposing the deepest parts of herself. Her breath grew labored. Her blush reached new heights. "I-i-is this okay?” she managed to ask.

“It’s exquisite,” I replied. ‘Fuck making them count. Just take ten of these.’

I snapped and snapped away. With each click of the shutter, Fluttershy’s back arched more and more. After three she actually began to drip onto the sheets. After seven I could see her inner walls beginning to pulse. Her model’s gaze began to falter. At ten she actually came. Her entire body shook for a single moment. It wasn’t a grand or glorious climax, just a tiny little orgasm.

“Having fun there?” I asked, hoping for a positive response. I did not get one. In retrospect it was a bad move. I should’ve played dumb.

“Oh… Oh my goodness.” She looked mortified. “I’m… I’m… eep.” She dove behind her mane. She grabbed a nearby pillow in an attempt to hide herself. She was in full blown panic mode.

‘Your client is freaking out. Engage emergency protocol! Extra gentle? No, it hasn’t produced results as good as I would’ve liked, she’s still nervous after a while of that. Downplay it.’

Casual tone. “Don’t sweat it… that ends up happening a lot of the time.”

“W-w-what do you mean?” she peeked out from behind her pillow.

“Fluttershy, I’m a whore. People usually come here to get off. That’s what I do.” I started gathering up the pictures that were taken. Acting like nothing happened was also a valid strategy. “Come on. Let’s have a look at these. I think there are some really good ones in here.”

She, cautiously, followed me out of the bedroom, and joined me at the table.

We spent the next few minutes looking over the photos. A distraction was the perfect thing to get Fluttershy to stop panicking. “These came out pretty good, don’t you think?”

She nodded. “I… I look sexy.” The smiled, blushing.

“You do. And I’m glad you like them, I was worried you would think they went too far.”

“N-no… they’re perfect… well, most of them.” She did her best to avoid looking at all the pictures where she was drunk with pleasure.

“What are they for, if you don’t mind me asking?”

“I… I was going to give them to somepony,” she admitted.

“Oh yeah? Your special somepony?”

“He’s… well, not yet… I mean… I hope he will be someday.”

Red flag.

“Fluttershy, are you going to use these to… profess your love for somepony?” Such a bold move struck me as being beyond Fluttershy.

“I… I wanted to at one point. Rarity talked me out of it. She said it would send the wrong message.” She admired the photos again. “She was right, I think. But, I always wanted to… to do it. To take… naughty pictures. I could always give them to him some other time. They would make a good Hearts and Hooves Day gift, wouldn’t they?”

I felt relieved. If Fluttershy embarrassed herself like that, I might’ve taken some flak. “I think they would.”

She smiled. “More than anything though… I… I wanted to know that… that I could… could do it.”

“Do what?”

“Be… be sexy for somepony.” She smiled. “I… I really can, can’t I?” She admired the pictures further.

“Well you weren’t a model for nothing.” I met her gaze. “Why did you quit? You’re very photogenic.”

She let out a heavy sigh. “It was… scary. So many eyes staring at me. I was… always so nervous. I hated it.”

A waste of talent, in my humble opinion. You get over that sort of thing if you try hard enough. I know I got used to something like that. Something even harder, I would deign to say. Still, I chose my path, and Fluttershy chose hers.

She regarded the photos once more. “I hope he likes them… if I ever get give them to him, that is.” She began to pout. “I don’t know the first thing about relationships.”

“Me neither,” I almost said. It was my de facto response. My old, practiced “I know what you mean” line.

But… but that wasn’t true anymore. I had a little over a month of relationship experience under my belt. Derpy and I were… dating. I understood infinitely more about relationships than I had a month ago. I’m no longer the unable to help in this department. There’s… some wisdom I can offer.

“I don’t know much… but I do know some.”

She looked up at me. “You… you’re dating Mrs. Hooves aren’t you?”

I hesitated, but ultimately nodded. “For about a month now.” This was okay right? Derpy told me I could tell ponies. She said people mostly already knew about us. “It’s my first real relationship.”

“Wow... I thought I was the only one who hadn’t been with anypony for this long.”

“Yeah, I felt kinda the same.”

She worked up the courage to ask a question. “How… How did it happen?”

“You mean, how did we end up together?”

She nodded. “How does that sort of thing just… happen?”

“Well…” I hadn’t told anypony this yet. “… It’s actually kind of silly.” I cleared my throat. “My first date with Derpy… wasn’t a real date. It was a practice date, Derpy felt like she was a little rusty, so we went out to dinner.” I smiled as a reminisced. “At the end of the evening I asked if she wanted to try again for real.”

Fluttershy tittered. “That’s really sweet.”

“She punched me in the chest,” I stated, much to my client’s surprise.

“W-what?!”

“When I asked. She punched me square in the chest… like, a lot.” I rubbed the long healed bruise. “Apparently somewhere down the line, I’d mentioned that escorts aren’t supposed to date clients. She got mad that I’d lied to her.”

“You… you aren’t supposed to date clients?” she inquired.

“Well… that was an old rule. Back from when I worked in a stable. But… well… I fell for Derpy. Some part of me decided that that rule wasn’t going to stand in my way.”

“That’s still kinda sweet… even if she did hit you. What happened after that, though?”

“Well, after she calmed down, she said she’d be willing to try a real date. So we did… and things just kind of went from there.” Fluttershy hung on my every word. “We make an effort. Our schedules don’t always match up. We fight sometimes. But we’re still together. It’s only been a month, but… I dunno… It’s…”

I realized I didn’t have a word for how I felt. There’s been so much change since I started dating Derpy. Changes with us. Changes with me. I find myself always thinking about her, and not just in the day-dreamy sort of way. Every move I make, every decision, it now all takes Derpy into account. I’m forever planning around her, it’s exhausting, but I somehow love it. It’s like we’re on a team, Derpy and Guilty against the world. And I’ve learned so much about her. Not her hobbies or her past or anything like that, but… how she looks when she’s mad, what sets her off, what pet names she likes to be called. Things that nopony else really knows about her. Things I don’t really know about anypony else.

There’s so so so much to know about somepony and the scariest part of it is that Derpy has probably started noticing the same things about me. I never thought one could know this much about somepony else. And now, there’s somepony who knows that much about me. I’ve never been this close to anypony before. Not to Close. Not to Ms. Smile. Not to Sunny. This is… love. Real romantic love, and it’s…

“… a trip,” I finally said.

“Is… is that a good thing?” Fluttershy asked.

“Yeah… it’s a good thing.” I glanced at the clock. “Well, your hour is almost up. Were you… planning on staying longer?”

“N-no, I... I think I should get home.” She gathered up her photos. “Um… thank you, G-g-guilty. It was… it was very… nice… today.” She reached into her bags and produced my fee. “M-m-m-maybe I-I’ll finally be able to… to a-ask him out. After what you told me, I… I kind of feel like I can.”

“Well… I hope things work out.”

“Thank you Guilty... Umm… Bye.”

“Bye,” I replied. And with that she left. Leaving only a wrinkled bedspread and the scent of her arousal. I hope things work out well for her and her mystery stallion.

It’s probably Big Macintosh.

Oh, I forgot to write about that potion Zecora gave me. It actually sounds pretty awesome. According to the label it’s called “Thunder’s kiss.” I’m supposed to apply a single drop to… wherever… and the affected skin should “provide pleasure unmatched.” I’m gonna try it out with Derpy at some point. It should be fun.

Author's Note

Thanks as always to Blackskulls, aquapunkchick, JakeTheArmyGuy, and coandco. WIthout them this fic would be far less amazing.

I'm fairly pleased with this chapter, I feel pretty good about Fluttershy's characterization.

it was kinda rough pumping this chapter out, my vacation was a little busier than I was expecting, and I barely got the first draft done before school started. Time kind of flies when you're running around doing paperwork.

Still, hopefully the next chapter won't be as long. It's going to be a big one. :rainbowwild:

Home

Chapter 24

Home

It started rather innocently: a simple Sunday morning lounging in bed with Derpy, post-coital bliss and the promise of muffins. It’s pretty much the same routine as it’s always been. “We should go,” Derpy said.

I looked for a clock. “That late already?

She laughed. “No, silly. Manehattan.”

I’d mentioned Manehattan off-hoof this morning, and Derpy was once again expressing her desire to visit. It’s something that had come up a few times at this point.

“I keep telling you: get a sitter for a weekend, and we’ll go. It’s just a train ride away.” I nuzzled her, too busy enjoying her presence to really pay attention to the conversation. Her warmth against me, the feeling of her coat brushing against mine, this has become my new happy place.

She returned my nuzzle. “Maybe I can do it this weekend. I might be able to set up a sleepover or something. I really want to go.”

“Well, just let me know.” Again, half-listening, just keeping the conversation moving.

As much as I was enjoying the moment, my muscles began to twitch restlessly. “I think it’s time for a shower.”

“Yeah,” she responded, righting herself. She rolled herself off the bed with some effort, and staggered onto the floor. “You coming?”

“Mm-hmm.” I dragged myself off the cloud after her. After some shower cuddles and appropriate amounts of scrubbing, the two of us enjoyed another lovely meal of tea and muffins. We said our goodbyes, made plans to meet for dinner on Wednesday, nothing out of the ordinary.

Perfectly normal.

There was one client on my schedule between then and our dinner date. Bottlecap’s sessions are usually easy. She talks a lot, so I just have to listen. She likes to complain about co-workers and gossip, pretty standard stuff. She’s very passive in bed, I end up doing all the work, but I wouldn’t have it any other way.

I realize, I’ve been writing less and less about my normal sessions, and more and more about my interactions with Derpy. This relationship has become… the forefront of my life. Derpy has become the thing I think about the most, the thing in my life that warrants the most concentration. It’s a challenge, and, honestly, it’s a little scary that she’s on my mind so much. At times I feel like I’m thinking so much about her that I’m becoming… dependent on her.

However, at the same time it’s the most thrilling and exciting thing I’ve done in years. I’ve had higher highs and lower lows than I’ve ever had in my entire escort career thanks to this relationship. We’re officially dating; that’s what we’re calling it. It’s nice to have a label.

Wednesday was pleasant as well. Dinner at a restaurant. At this point, the whole town knew we were together. It was nice, in a way. It meant fewer confused stares. The waitress at the little pasta place was even used to me at this point. Overall, things were going fairly well.

“Hi there. What can I get for you?” I was appreciative of the familiar over-enthusiasm from the wait-staff. It felt sort of like home.

“The spinach ravioli for me. Water to drink.” I’ve taken to forgoing wine, seeing as Derpy can’t drink during the week.

“Sure thing,” she responded cheerily.

“I want theeeee…” Derpy browsed the menu. “… split pea soup.”

“And what would you like to drink?”

“Oh, just water.” She always forgets to ask for water. It’s adorable.

“Okie Dokie. We’ll have that right out for you.” She grabbed our menus and took her leave.

Derpy happily grabbed a breadstick from the middle of the table. “So, you seem pretty relaxed tonight, Guilty. Had a good week?”

“Yeah, I did. Very relaxed.” I grabbed my own breadstick and tore it in half. “Things have been very low-stress, lately.”

“Dhaass ghud,” she replied through a mouthful of food.

“Yeah,” I replied as I tore my breadstick, dipping it into some olive oil. I just smiled at her; I’ve come to cherish moments like this one. Not a care in the world, just quality time with the mare I love.

“MMMM, bvvfr M fvrgvt.”

“Run that one by me again.”

She swallowed. “Before I forget… I set up sitter for Dinky this weekend and I took the weekend off of work. We can go to Manehattan!”

My eyes bulged. “Wait, what? Really? ”

“Yep! What should I pack?” Her eager expression could light up a room.

“I… uh… warm clothes and a camera, I guess.” This was happening so quickly. I hadn’t been home in over two years, and suddenly I was going this weekend. “I… wow… that was fast.”

Derpy’s brow furrowed. “I told you I might be able to do it this weekend.” Her face betrayed concern. “Is... now a bad time?”

I shook my head. “No no, I do. It’s just… I dunno… so sudden.”

“Are you sure? We don’t have to go.” Her hoof found its way to mine. “It’s okay, really. We can just spend the weekend together here, if you want.”

I smiled at her. “No, we should go. It’ll be fun, an overnight trip. I know a good hotel.” As the shock wore off, the trip was sounding more and more exciting. No reason not to go. Nothing to be afraid of. “So, what do you want to do when you’re there?”

“I wanna go see the Statue of Harmony!”

I rolled my eyes.

“What?” she laughed at my apparent misery.

“It’s so… tourist,” I groaned.

“Guilty, I am a tourist.” She smiled triumphantly, as though that were some manner of accomplishment.

“Yeah but…” That smile… it had power over me. I didn’t dare disappoint it. “… fine… but that’s the only touristy thing we’re doing.”

“This trip,” she insisted. “There’s still a bunch of stuff I want to do.”

I stifled another groan. “To be discussed.”

It was Derpy’s turn to roll her eyes. “Okay then, what do you wanna do, Mister Manehattanite.”

Ideas exploded into my head. Good bars. Good dance clubs. Art Galleries. Plays. Culture. “Pizza,” I finally decided.

“Pizza?”

“Pizza! At Hardy’s on 36th. Best in the city. It is an absolute must.”

Derpy giggled. “Guilty, you’re adorable.”

I felt myself blush. “What? Why?” She’s called be that before, but I couldn’t figure out why she was saying it now.

“You’re so enthusiastic about pizza. It’s cute.”

“Don’t tell that to a Manehattanite. Pizza is serious business.” I stuck a tongue out at her. ‘Good, embrace the embarrassment. If you own it, it can’t hurt you. Classic Guilty.’

Derpy just smiled at me. “You really miss it, huh?” A single pang of worry. Just a flash in her eyes. Fear of some kind.

My brain was firing on all cylinders. ‘Identify the worry. Comfort your girlfriend. About me missing Manehattan what could— Actually this one’s easy.’

“Derpy, you know I’m here to stay, right? I’m not going to move back to Manehattan.” Flawless execution. Comfort complete.

Rather than the warm smile I was expecting, I received a stern glare. “Guilty, you’re doing it again.”

I blinked. “Doing what again?”

“You’re trying to fix problems that aren’t there.” She reached across the table to give me a soft punch in the shoulder. “Guilty, you don’t need to try comfort every time you think I’m just a little bit upset. I wasn’t even thinking about that.”

“But you...”

“I was just thinking how hard it must be on you to be so far from a place you love so much. I wasn’t worried, I was just…”

I lashed back, foolishly. “Feeling sorry for me?” I intoned.

She gave me a look. “Don’t turn this into that. We are not having the pity conversation right now,” she hissed.

I stopped myself. We fight a lot about that. I don’t like feeling pitied, and at times I perceive pity where there is none. But, Derpy was right, this was not that fight. My ears dropped in shame. “Sorry, you’re right. I just…”

“It’s okay,” she said, half-angry. She checked her surroundings, making sure no one had heard her minor outburst. She tore off another piece of breadstick. “Just… stop trying to fix everything… and stop thinking you can read my mind.” She took a large bite.

I wasn’t wrong, though. She was worried about that. I know that. I don’t suspect or think, I know.

See, this has become… a problem for us. I’ve come to know Derpy better than I ever have. As such, I’m getting even better at learning her tells, and knowing what she’s thinking. That’s just my special talent at work.

However, I… I sort of can’t help but try to act on those tells. It’s stimuli I can’t ignore. I see an upset Derpy, and I want to make her not upset. Call it training, or instinct, or conditioning it’s just… hard for me to let it go.

But the thing is it’s not my job to fix Derpy’s problems; she’s a fully grown mare. I just have trouble remembering that because… well because I care about her so much. Even harder though is the fact that I’m right! I’m not wrong about these tells, these stimuli, these problems that I can see. I know what she’s thinking a lot of the time!

But maybe that’s the problem. I can know what’s on her mind when… well… maybe she doesn’t want me to.

And that’s more than fair; everypony is entitled to privacy.

Maybe I can’t just be in a relationship. Maybe I’m literally incapable of leaving a person alone. I’m too perceptive to give a pony any real privacy.

Okay, now I’m just being silly, back to the dinner at hoof.

“Anyways…” I needed to change the subject. What were we talking about before? Right, Manehattan. “Would you want to go out drinking? There’s some good clubs. There’s really nice restaurants, if you feel like something fancy. We could see a play. What sounds fun?”

Derpy did her best to push off the foul mood I’d put her in. “I dunno, Guilty… drinking would be fun. I don’t get to do that a lot.”

A plan instantly formed in my head. “Perfect. I know a good dance club by a hotel. We can go, drink, dance, and just walk back to our rooms. Sound fun?” I added a layer of enthusiasm to my spiel. Anything to help lighten her mood.

She smiled, thankfully. “That sounds perfect, Guilty.”

The waitress returned at that moment. “Okay, that’s one spinach ravioli, one split pea soup, and two waters.”

Warm smile. “Thank you so much. Everything looks wonderful.”

“You’re very welcome. Let me know if you need anything else.” She gave a quick bow, and left us to our meals. It felt good, almost like I was nobody again. Like I wasn’t “the whore”.

Derpy and I spent the course of the meal planning the trip, and we came up with something of a schedule: the statue, then pizza, the museum of art, dinner, and then dancing. It sounded kind of like a perfect day.

“One thing, though.” I wiped my mouth, ravioli now devoured. “I have to stop by the old stable and say hi to Crook. If he finds out I was in Manehattan and didn’t stop by, he’d beat me. You don’t have to come; I’ll just stop in and say hi.”

Derpy’s eyes went wide. “No no no, you have to take me. I really wanna see where you used to work. I bet it’s awesome!” She had a giant grin.

“Sure thing. Of course you can come.” I smiled back. It would be fun seeing the old place…

…so long as I could keep under the radar.

“And, here you are!” the waitress cheerfully chimed. She placed the bill on the table. “Whenever you’re ready.”

“Thanks.” I looked at the bill. Not a big expense, but not cheap. ‘I should pay. Derpy’s got enough on her plate.’

“How much?” she asked.

“I got it.”

“You sure?”

“Yeah, I got it.” Not wanting to leave further room for dispute, I pulled out my wallet.

Derpy frowned. “You don’t always have to pay, you know?”

Tactical smile. “Oh, come on. Let me be a gentlecolt.”

She laughed at that, and relented. I couldn’t help but feel a little shitty about that, honestly. I give her such a hard time about pitying me, but this was clearly me pitying her. I don’t know… is it pity if it’s what society expects?

I’m such a hypocrite.

I walked her home, like always. We talked about Manehattan, got ourselves excited. Everything was happening so fast. But even so, I was beyond ready. I suppose I’d been ready to take a trip home for a while. At her doorstep, I had a bit of a flash back. It was snowing, the town was asleep. It was just like the night of our fake date.

“What are you smiling at?” she asked.

I blushed. “You.”

“Aaaw. You’re sweet.” She leaned in for a kiss, which she received. As I broke away, her hoof found its way around my neck. “More.” she insisted, eyes still closed. I was pulled into a deep kiss, tongue and everything.

I’m getting better at kissing. No longer do our teeth knock together… most of the time. And, I’ve managed to learn what an appropriate amount of tongue, is… kind of. Hey, at least I haven’t drawn blood since that one time.

Yeah, I’m awesome.

As the kiss broke for the second time, I couldn’t help but smile. Neither could she apparently. We were both grinning like idiots. “Goodnight, Guilty.”

“Goodnight, Derpy.”

She disappeared into her house, and I made my long walk home. I didn’t get any sleep that night. I was way too excited. I kept thinking about pizza and dancing and a thousand other things.

That Saturday, I hurried over to Derpy’s early. We were going to take the 7am East to Manehattan. We’d arrive before ten.

I knocked on her front door, bright and early. “All packed?” I asked as she opened the door.

“Yup! Just gotta take Dinky over to Goldy’s place.” She turned back into the house and shouted to her daughter. “Sweety, you ready to go to Aunt Harvest’s?!”

“Yeeeeees!” she called back from within. Moments later a tiny unicorn with bright yellow saddlebags emerged from the home. “Hi, Mister Guilty.” she said with a yawn. “Why do I have to get up so early? It’s Saturday.”

I tensed. Kids. Awkward. I will say: I rather like the name Dinky uses for me. Mister Pleasure would sound weird from a foal’s mouth. Guilty, is a little to casual. Mister Guilty, on the other hoof, strikes an appropriate level of respect without being racy.

“Because. Mommy’s getting on a train, and she’s not going to leave you all by yourself.” She kissed her child on the top of her head with an audible “Mwa!” This, of course, cause Dinky to groan tiredly.

Derpy eventually noticed my awkward silence. “Tell you what. Why don’t you tell Guilty about your new friend at school?” Equal parts “wake up Dinky” and “Force Guilty to interact with Dinky.” Well played, Derpy.

As we walked Dinky regaled me with stories of young filly named Firelock. She was apparently quite the little unicorn athlete. Dinky and she had taken to playing hoofball. Truthfully I was only barely listening, but Dinky was content to simply talk about her friend. It kept me from having to actually talk to her, which worked just fine for me.

We arrived at Goldy’s house, or rather Goldy and Lily’s house now, and Derpy knocked on the door. I’ve seen the pair several times since they came to visit me that once. Things seem better between them. They have officially moved in together. They don’t seem to bicker as much. Things are at least more… stable… between them. I’m cautiously optimistic.

Lily answered, looking chipper and energetic. “Morning, morning, morning!” So much energy. She is clearly a morning pony. “And how is my favorite little foal?” she asked to Dinky, who was now marginally awake.

“I’m fine.” Insert adorable tiny yawn. “Where’s Aunty Harvest?” she asked tiredly.

“Well, sweety, she’s still sleeping. Why don’t you help me finish breakfast, and then we wake her up?”

Dinky smiled, and nodded in approval, before disappearing into the house.

Depry smiled at Lily. “Thanks so much for this. I know you guys are still getting settled and everything—”

Lily cut her off. “No problem at all. I love watching Dinky. We both do. Besides, I love that you two are visiting Manehattan. It sounds like a nice getaway.”

“Uh-huh! Guilty’s gonna take me to do touristy stuff, even though he hates it,” Derpy teased.

“I am, and I do. But tourists will be tourists,” I teased back.

“You’re lucky I like you.”

Lily laughed at our expense. “You two are always so funny, the way you play off each other like that.”

Derpy and I shared a look. She smiled warmly at me. “We’re just weird that way, huh, Guilty?”

“I guess.” I stuck my tongue out at her.

Lily chuckled at us. “Well, I won’t keep you. Go catch your train.”

With a friendly “goodbye” Derpy and I made our way to the train station.

It felt good to be on a train again. I hadn’t ridden one since I took my trip here. Bright and early, not a soul in sight, and we were headed to the greatest city in Equestria. All in all, it was a damn good morning. For a time, we just enjoyed each other’s company, alone on a train. As ponies began to filter in, our conversation lulled. After a time, we stopped talking altogether. We were just leaning into one another, allowing ourselves to simply share the moment. The shaking of the train, the din of other ponies’ conversations, it was pleasant.

As the city grew closer, more and more ponies stepped onto the train. Ponies catching the morning commute. Ponies heading into the city for a day trip, not unlike ourselves. A Griffin couple, giving everypony the stink-eye. It was already feeling like home.

Then we hit the bridge. Manehattan is only accessible by boat or train, and all trains go over the Hocklyn Bridge. We were close. I was almost home. I felt the hairs on the back of my neck stand up. I was excited. Beyond excited. Home. I was home. Even now. Even after two years in Ponyville, Manehattan is still really home.

Once we were in the city proper, ponies started to come and go more frequently. The train car got really crowded, and Derpy and I were squished together, as seats filled up. Derpy had clearly never been on the train when it was this crowded before, she was getting a little uncomfortable. Bully for me; I got to play the role of protective boyfriend. I gave her hoof a firm squeeze, and shot her a comforting smile. She smiled back, and calmed down. She was going to have to get used to the crowds pretty quickly.

Our station arrived, and we made our way off the train. Squeezing ourselves by other passengers, and hurrying for the doors before they closed, bags held tight. You never forget how to get around in Manehattan.

And then we were outside. The tall buildings, the crowds of ponies, the din of the city.

Heaven.

“Guilty! Help!” My head shot around. Derpy was trapped behind a wall of ponies walking away from me, carried away by a current of indifferent Manehattanites.

“Make a gap, ya fuckin’ animals,” I shouted, catching up to the wave and physically parting them.

“Hey, watch it!” one of them yelled.

“Shove it, Hairpiece!” I took Derpy’s hoof and pulled her through. The sidewalks were busy as always. I was going to have to play escort for Derpy. “Stay close,” I said, leading her to the street. “Taxi!”

A pony pulled up, drawing with him one of Manehattan’s many many taxis. “Where to, mack?”

“Tiara Plaza,” I said, as I stepped onto the cart. Derpy quickly followed suit. “If you wanna wait, we’re goin’ to Harmony Island after we check in.”

The cabby just nodded, and off we went.

It felt good. The pace of the city. We went from train, to station to street to taxi in just over a minute. Things didn’t take forever here. I didn’t need to stop and say hi to everypony I came across. It was great… and Derpy is frowning.

“I’m so sorry Guilty. I got caught up looking at the buildings and, I just kind of got swept away.” Her frown deepened. “I can’t believe they wouldn’t let me by,”

“Don’t worry, Derpy. It’s Manehattan; it’s weird if you’re polite. You’ll get used to it. Everything moves a little quickly here, but don’t be afraid to push and shove.” That seemed to cheer her up. “Just don’t punch anypony. The cops will get involved, and it will be a whole… thing,” I teased.

She groaned. I think I reminded her about slugging Applejack. She punched me in the arm.

After some heavy traffic, a snooty concierge, a quick elevator trip to drop off our bags, and a steep fare, we arrived at the ferry station. Derpy’s mood shifted when the statue came into view.

Crook always had a joke about the statue. “Finally a broad big enough to take me in, am I right Guilty?” Always made me roll my eyes.

It is a pretty impressive statue, stories tall and rusted green with age. A gift from Prance, I think. I dunno. History blows. I sucked at history.

I’m actually not a stereotypical Manehattanite. I’ve actually been to many of the tourist attractions around the city. When Crook and I were kids we’d blow of school and sneak into tour groups. It was decent camouflage. Everypony assumed we were somepony else’s problem children.

So across the water we went. The ride was rockier than I remembered. I started to get a little bit sick. Derpy got a kick out of it. She gave her full attention to the tour guide as he rattled off facts about the statue and such. I didn’t really have any interest in what he had to say, but this was for Derpy.

All the hiking has been serving me well, as the walk up the steps didn’t even faze me. Derpy was a bit winded, but she wasn’t dying or anything. They let us into the head in small groups. It’s pretty cramped up there. Derpy and I got stuck with a family with four obnoxious kids. Derpy was too excited to care.

The view was what really got Derpy excited. “Ohmygosh Guilty, look! It’s the city!” Derpy really is rather adorable when she’s jumpy. Always shouting and pointing at what’s got her excited. I love her for it. She took a picture of the city, and asked the stallion to take a snapshot of the two of us. She got her film developed once we got back, those pics ended up looking really good.

“That was so much fun, Guilty!” She was still full of energy, giddy the entire ferry ride back.

I wrapped a hoof around her. “I actually managed to have a little fun. Even if it was mostly having fun watching you.”

We disembarked and made our way to another taxi. I didn’t want to subject Derpy to more train rides.

Then came that most sacred of acts: the consumption of pizza. Every Manehattanite has a “best in the city,” a pizza place that, to them, surpasses all others. It just so happens that my best happens to be the best. Anypony who doesn’t think that it’s Hardy’s on 36th is a fucking moron.

“So this is Hardy’s,” I excitedly explained to Derpy. It was clearly my turn to be giddy. “I used to get pizza here so often with Crook. Oh my gosh, it still smells the same.” My mouth was actually watering as I spoke.

Derpy giggled. “Guilty, you’re adorable.” She must’ve felt like I had minutes before. I’m sure I was just as giddy and excited about Hardy’s as she was about the statue. “Just cheese on mine.”

“Sure.” I walked up to the counter, and there he was: Hardy. He was an older Earth Pony, hefty guy, nasally voice. He’s been making pizza here for as long as I can remember.

“What’ll ya have.” I love his demeanor. He’s not friendly, he’s not trying to please you. Hell, he actually sounds a little bit annoyed, but I missed it. Everypony in Ponyville is such a pleaser; it’s nice to have someone in the service industry who doesn’t give a shit about me.

“One with mushrooms, one with nothin’.”

“Comin’ right up, that’ll be 6 bits.”

I hoofed him the bits and made my way to the table where Derpy was sitting. She was inspecting the restaurant, and not in an impressed way. It wasn’t a… a fancy place. It was… okay it was kind of falling apart. Fraying hoofball pennants on the walls, ripped wallpaper, the stuffing was starting to come out of the chairs, the tables were stained and scraped, and there were initials carved into them, but this was Manehattan. It’s not the idyllic, island city that everypony thinks it is. It’s more than the skyline, and pictures of busy brightly lit streets. It’s small local places, and the apartments on top of them. It’s traffic and loud abrasive people. I didn’t want Derpy to see just the pretty side of Manehattan. I wanted here to see all of it. And Hardy’s was a good little piece of my less-than-pretty city.

“Not what you were expecting?” I asked.

“Not… really,” she was trying to avoid insulting the pizzeria.

“It’s a dump, right?”

Her eyes widened at my bluntness.

“This might not be the Manehattan that you wanted to come see today: the shabby little pizza place that’s far away from any of the famous landmarks. But... this is the Manehattan I grew up in. I lived in a shitty apartment in a shitty neighborhood, and I went to a shitty school.” I looked fondly upon my surroundings. “Where I grew up wasn’t anywhere near as nice as Ponyville. But honestly, this is where I’m… the most comfortable.” I leaned back in my rickety chair. “Feels good to be home.”

Her face betrayed that pang of worry again. ‘Ignore it, Guilty. No need to start another fight.’

“I just wanted you to see my Manehattan, too. I love this city, all of it.”

She offered a smile. It seemed forced, but I wasn’t sure. Perhaps I was reading too much into it.

“Here ya go, kids,” said the pizza pony. “Bon appetit.” He placed two slices of pizza on our table. Fat and wide, thin and greasy, they stained the paper plates that barely held them.

“It’s huge,” commented Derpy.

“Dig in,” I said, wasting no time with my own pizza.

Fucking bliss. One bite and I was thirteen years old again, sharing slices with Crook, hard bought with our earnings from the Stable. Food has that power, I feel, to just kick your nostalgia into overdrive. Make you remember things you’d forgotten, just put you back in a perfect moment in time. “Guilty, it’s really good! Are you crying?”

I wiped at my eyes. Yep… yep I was. “I ‘aven’t had a decent fuckin’ pizza in two years. You bettah believe I’m cryin’.”

She giggled. “Your accent’s back.” She clapped her hooves a couple times. “I love it when you talk like that, it’s adorable.” As she snickered, she picked up her pizza and took another bite. An expression of ecstasy emerged on her face. “This is the best pizza I’ve ever had. I’m not joking.”

“Because Ponyville has no real pizza. I tried every pizza in town, and not one of them compares.” I quickly hid my accent again. Derpy likes to tease me about it. I get so comfortable around her… sometimes I forget to be proper. “Oh my gosh, I’m so happy right now.”

“I’m glad,” Derpy said. Just like I’d enjoyed her reactions to the statue, she was enjoying mine to the pizza
.

As we ate, I noticed that the owner was listening to the radio, hoofball by the sounds of it. “Who’s playin’?” I shouted to him.

“The Clubs and The Dashers. We’re down by two.” He removed his hat to rub his bald head. “Clubs’ve had a shit fuckin’ season.”

“Tough time to be a Clubs fan,” I responded. I didn’t actually know the current state of the hoofball world, it’s hard to keep up in Ponyville.

He chuckled. “I hear that.”

Derpy chuckled at our interaction. We quickly devoured the slices of golden goodness. Derpy more than enjoyed her first taste of real pizza. “So… museum?”

“Yeah! Let’s go!”

The rest of that day was bliss. We went to the art museum, which was a blast. I don’t know much about art, but I could spend days just looking at the exhibits in that place. Derpy and I spent our afternoon stumbling from painting to painting, sculpture to sculpture. We wandered from hall to hall just taking in everything we could. I offered to pay for an audio tour, but Derpy didn’t seem to want to know anything about the exhibits; she just wanted to look at them.

I’ve always had an appreciation for portraits. During my training, I always saw them as challenges. Obviously, I couldn’t read a portrait like I could read a pony. Ponies spoke and moved. Tells revealed themselves through time, with observation. But portraits were frozen, without movement. A perfect poker face. None of the subtle clues about emotion or attitude made it past the filter of the artist’s vision. The only emotions on the canvas were the ones that the artist wanted there. I could stare at a portrait for hours, searching for clues that weren’t there.

Derpy, on the other hand, had a love for paintings of action: battles between the three tribes, battalions of soldiers charging a hill, the princesses fighting on Nightmare’s Advent. They were all exciting events frozen in time. The dynamic made static.

Our next stop was dinner. After a quick trip back the hotel to change into something fancy, we headed to a nice restaurant nearby. The museum turned out to be a great idea; we talked about art over our meal. I splurged a little on a nice restaurant. Candle lit table, a bottle of wine (which Derpy actually got to drink), fried roses, the atmosphere was sublime. Derpy talked about Lily and Goldy. She also seemed to think that things were much better between them. She had, however, noticed that there was a period of time when Lily was very awkward around her.

I simply nodded.

She talked about Dinky and muffins. She mentioned that we should go visit the mantle ray again. I told her what I could about clients that had visited. Never used names, never left anything that could lead back to an identity. It made small talk difficult, but Derpy understood.

After dinner we took a cab to The Cricket Club. It’s a night club about half a block from our hotel. It’s a real night club too; live big band music, a well-stocked bar, no obnoxious bassy noise or neon lights or fog machines.

This was something that they didn’t have in Ponyville. I thought Derpy would appreciate it, she always says she wants to go dancing. After a couple drinks, we hit the dance floor. I might’ve been a little bit buzzed, but not so buzzed I couldn’t cut a rug.

I always enjoyed dancing, but it was never something that my training emphasized. I was taught just enough to seem like a good dancer, like so many other things. Furthermore, it’s a skill that seldom comes up in a session. Few mares want the whole “dashing prince” experience. Still, I’ve always been happy to have the training.

We danced in the crowd, everypony was well dressed, the air was thick with cigar smoke and heavy perfume. This was a proper club. As the night began to wind down, the fast-paced dancing music began to turn slow. Derpy and I gladly took the opportunity to lean into each other and enjoy a good slow-dance.

I felt... so close to her. The rest of the world melted away. All worries, all problems, all fears were just... elsewhere. All that niggled at me was somewhere far away, and all that I could see or even feel was Derpy, my cross-eyed little girlfriend.

It seemed to last forever, but it was still over too soon. So much had been happening, and we were having so much fun that the day just sort of flew by. Before I knew it, the bright lights were coming on, and everypony was leaving. It was sort of hard to believe. We’d had a wonderful amazing day in the city I love, and… and it was over.

As we left the club, Derpy leaned hard into me. “That was so much fun!” She stumbled a bit as she walked. Her drinks were catching up to her. “Guilty, this was the best!”

“I had fun, too.” I felt her wing drape over me. “I’m glad you liked it.”

“This was great. We have to do this again.” She stumbled into me a bit more as we made our way down the street. It was only a block to our hotel. I didn’t mind shouldering her weight.

As we approached the hotel I felt a tug at my shoulder. Before I could react, Derpy yanked me into an alley. “Whu—”

I was pulled into a hard kiss. “Mmmph—” I began to protest. My objection dissolved as Derpy broke the kiss, and began to pepper my neck with small pecks.

“What’s… unf… up with you?” I felt myself getting hard. Derpy’s arousal was palpable. Wine, Long Island Iced tea, and dancing had put her in an awesome mood. I felt a hoof begin to fumble with my zipper. “Here?”

I received no response. Rather than wait for an explanation, I decided to expedite whatever Derpy had in mind. I wriggled out of jeans. My erection began to bob beneath me. Derpy’s hoof caressed my length.

Before I made a move, Derpy repositioned herself in front of me. Tail swept to the side, begging for me to mount her. I wasted no time with foreplay; she wanted cock, and she was getting it. I hoisted myself onto her, and easily slid inside. Derpy whimpered with pleasure.

I started slow. The cold air accosted my moist member with each slow retraction. I kept my eyes and ears fixed on the entrance of the alley. I wanted to be ready to dismount and play it cool at the first sign of anypony.

Derpy began to get vocal, whimpers becoming moans. I shushed her, and she promptly muffled herself. Still, she fought back her moans of arousal, and her body began to move in rhythm with mine. We matched each other’s thrusts. They weren’t mighty slapping thrusts of flesh on flesh, they were careful, nervous, shaky thrusts. Eager but cautious, each one sent the squelching noises of our loins into the air. Ever watchful of the street, we continued our slow, rhythmic, intoxicating, mind-blowing sex. Every few dozen thrusts Derpy would moan and tighten and quiver. Her orgasms were powerful, magnified by the thrill.

Snow began to fall.

After being banished to the acre outside of Ponyville, I decided that trying to do anything with a client outside of my home would be a bad idea. As such I haven’t had sex anywhere other than my cabin in two years. Sex outdoors was even further taboo, I decided. One or two clients were disappointed I wouldn’t come outside to play, but it was just something I couldn’t risk.

But I wasn’t in that little backwards burg right now. I could enjoy a little bit of sex outdoors, and the worst that would happen was a fine for indecent exposure… and maybe becoming a registered sex offender. Okay, it was still pretty stupid, but there was no threat of reprisal from Applejack. No fear of being banished from Ponyville entirely. That was a plus.

It felt amazing. My skin tingled with anticipation. My chest felt light. The fear of getting caught does good things to sexy-times.

Minutes passed. It couldn’t have been more than ten. Once the sheer excitement began to wear off, I remembered something exceedingly important. “Potion!” I whispered somewhat frantically to Derpy. I pulled out of her.

For a moment, Derpy panicked. The way I pulled out so quickly, she must’ve thought we’d been spotted. “What? What is it?” she whispered back.

“Birth control potions. They’re in my case in the hotel room.”

Derpy’s eyes went wide. She’d also forgotten completely. She squirmed out from under me and immediately began to help me into my jeans. We raced into the Lobby and into an elevator. Twenty-seven floors of waiting, it was agony. We were hanging off each other. Kisses down the neck, nips at the ear. We almost didn’t see the doors open.

At what was almost a sprint we raced to our door. My drunken hooves fumbled with the key. Derpy whined impatiently. Once inside, I made a beeline for my suitcase. Potion found. Cork popped. Brew swallowed. As I once again removed my jeans, I spun my head around. Derpy was already on the bed, legs in the air, hooves frantically rubbing her aching sex. “Hurryyyyyy,” she whined.

Hurry, I did. I was on top of and inside her before she could whine again. The sheets were cold when I climbed on, but they didn’t stay that way for long. Free to moan as loudly as she pleased, Derpy began to give off deep, throaty grunts of pleasure. “Oh… fuck!”

My mind was gone. I was drunk and horny and tired and all I could think was to thrust. I fucked hard, plunging into Derpy’s warm and oh-so-wet entrance with abandon. I don’t think it lasted five minutes, but it really didn’t need to last any longer.

Derpy came hard. Her marehood clenched down onto me with near violent force. I was almost pushed out of her with how much she squeezed me. “Oh… Guilty!”

My climax was next. Lightning in my spine. My entire body clenched around Derpy’s frame. I came… so much. Volume-wise, I mean. There was just… so much of it. It just kept coming and coming. After several seconds of bliss, we both went limp. It took nearly a minute to pull myself off of, and out of, her. I just… felt too good to move.

“Oh, holy shit,” I said dumbly. I rolled to the side, hips still twitching.

“Y-yeah,” Derpy responded. “Th-that was… the best. Like the best… ever.”

I nodded, though she couldn’t have seen me do so in the dark of the room. We hadn’t even turned on the lights. “It was…” I swallowed. My throat was dry and my breaths came in great heaves. “It was something, alright.” I could feel my heartbeat in stallionhood. My skin tingled. “Fuck…” I sighed. I couldn’t think. My mind was fried.

“Oh, my gosh,” Derpy said tiredly. “I… I can’t even think.”

“Me neither,” I responded. “I love you.”

Time stopped.

‘I… I did not just say that.’

A second passed. Then another. Derpy didn’t say anything. She didn’t move.

‘I fucked up… I fucked up, I fucked up. It’s happening again.’

I was shaking. Fear was beginning to take hold. I could think again. I couldn’t not think. Was this all it took? Was this what it took to ruin such a great relationship? Did saying that just make it too real?

‘I’m stupid stupid stu—’

“Wow,” she said. “That’s… wow.”

“I-I… I’m sorry. I shouldn’t have—”

“I-I just… I didn’t… I’m not…”

“I-I’m sorry. I...” My throat was closing up. I couldn’t breathe.

Derpy could see me panic. “Guilty, it’s okay.”

“I… I…” It was that fear. That absolute unfiltered fear. That fear when your secret is discovered. Did this count as a secret? I didn’t care; I couldn’t think. I just felt like… like the world was imploding. “I didn’t mean…” I was starting to cry. I didn’t want to cry. Why was I crying?

“Guilty. It’s okay, really it is.” Her hoof found my shoulder.

“I just…” Tears and panic. “I don’t want to screw this up. I know that we’re in kind of a fragile position and… and…”

“Guilty!” she shouted. “It’s okay!” I began relax. I could breathe again. “It’s okay.” She stroked my mane. “It’s okay.”

“I’m… I’m sorry.”

“It’s okay…”

“I just… I’ve felt this way for a while, I just… I didn’t want to make it too real.”

Derpy took a deep breath. “I-I know what you mean.” She chuckled nervously.

“Did… did I? Make it too real, I mean.”

She didn’t respond.

“I’m sorry.”

“I-it’s okay.”

“Did I…” I laughed nervously. “Did I fuck up our weekend?”

She thrust her face into my shoulder and shook her head. “No way. This… is awesome.”

“Good… good.” I swallowed. My panic had subsided. “I think…” I yawned. “I think I’m tired.”

“Me too.” Her head found my chest.

We fell asleep like that, with me as her pillow, trying not to think about what had just happened.

Before I passed out, I couldn’t help but lament the fact that she did not say it back.

I'm such a putz.

Author's Note

Thank you all so much for being patient. Writing this story has been an absolute trip, and I'm always happy to give you all a brand new chapter.

The rest of Guilty's Manehattan adventure will be coming as soon as i find the time.

Thanks once again to coandco, Blackskulls, aquapunkchick, and Jake the Army Guy for polishing my fic to a mirror sheen.

Family

Chapter 25

Family

I awoke to the shrill sound of rushing water. I rolled out of the haphazard sheets and pried my eyes open. Lights too bright. Sounds too loud. Hangover. I groaned and stumbled into the hotel’s rather cramped bathroom.

“Morning, Guilty,” Derpy managed to say through her own suffering. “Oh, my head.” She rubbed one of her temples in agony. She waved a hoof beyond the shower curtain to test the temperature of the running faucet.

“Yeah, we kinda went a little overboard, didn’t we? I lost track of my drinks after my second scotch.” I rubbed my own aching head.

Derpy nodded tiredly. “I don’t know how many of those big tall drinks I had. A lot, I think.” She laughed. It was a guilty sort of laugh. Did she feel bad about last night?

“You okay?” I asked.

She smiled and placed a hoof on my shoulder. “Yeah, I just… it’s been so long since I… cut loose like that.” She winced, and recoiled from the shower. Too hot, it would seem. “I think I kind of overdid it. I… I think I’m still a little bit drunk.” She belched. “I’m kinda queasy.”

“Well, we’ll get some breakfast. Something starchy and absorbe—” It hit me like a truck. The memory of what I’d said. The panic, the tears, the worry.

“Mind if I go first?” Derpy asked.

“Huh?”

“The shower.”

“Oh…” Of course. Not at home, shower only big enough for one, we couldn’t take it together like usual. My mind was working slowly. “… sure, yeah. I’ll… I’ll go grab us some food downstairs or something.”

‘Oh, geez… what did I do? What did I DO? Did I fuck this up? Did I fuck up the best thing to ever happen to me?’ I paused. I realized that I was right. Derpy was… the best thing that had ever happened to me… in my life. ‘I… I need to lie down…’ I was already on my way downstairs. I couldn’t come back empty-hoofed. ‘Okay… let’s just… get some breakfast, then.’

I dragged myself into the elevator, suddenly finding myself weary. ‘Okay, Guilty, just calm down. You haven’t ruined this… necessarily.’ I pressed the lobby button. ‘You just… you need to backpedal. You can do that, you were drunk, you can blame the alcohol and dancing and outdoor sex. Just say that you were caught up in the moment.’

The elevator was agonizingly slow. I just… I wanted something to distract me, and the tiny elevator offered little in terms of mental stimulation. ‘Then again… I was pretty heartfelt. I said that I’d felt this way for a while. I cried. I might not be able to play this one off. Oh my Celestia what have I done? What am I going to do? This is… this is bad, Guilty. You’ve lost her. She’s gone. Hoof in the door. Never going to see her again.’

I was being ridiculous. I knew I was, but that didn’t stop me from doing it. I took a breath. ‘Okay, don’t be stupid. Derpy said I hadn’t ruined… this.’ I thought about her exact words. “This… is awesome.”

But… what was “this.” Our relationship? This trip? That sex? I mean… she didn’t sound like she was going to leave me. ‘Listen to yourself, assuming the worst. She was perfectly happy this morning… okay, a bit hungover, but still happy.’ But maybe she was just waiting ‘till we got back to Ponyville. Maybe she didn’t want to ruin the trip. ‘Calm the fuck down. You’re freaking out. Don’t get worked up.’ I needed to talk to her. We could clear all this up if we just… sat down and parsed things out. ‘Don’t be stupid, Guilty, let sleeping dogs lie. Things are at a passable status quo, don’t fuck that up.’

The door opened. I stepped out into the large lobby. Lucky me, there was a little breakfast buffet. Bagels, melon, muffins (or what passed for muffins in the world outside Derpy) all sat out in neat little piles. I grabbed a couple small white plates and started stocking up. ‘Okay, so don’t go mucking things up by bringing up last night again. It will accomplish nothing. It will make negative progress. It will spoil this perfectly good trip.’ I paid for our meals and made my way back upstairs. Another long trip in a tiny box.

‘Okay, so what’s the plan for today? Probably gonna visit the old stable. That’ll be an interesting challenge.’ Despite my best attempts to shift my focus, I couldn’t help but think about last night. ‘It was the alcohol. I had too much to drink.’ My head pounded as if in agreement. ‘ I just hope I haven’t… scared her off or anything.’

Back to my floor. Back to my room. “Derpy?” I yelled. “I brought breakfast!”

“Okay!” she called over the shower’s spray.

I began to lay out breakfast on the room’s tiny table. ‘Crap. I didn’t grab anything to drink.’ I sighed; tap water would have to do.

Derpy emerged from the shower, a towel wrapped atop her head. “What’d you grab? Oooh, Muffins.” She sounded very far from chipper. Her voice was gravelly and hoarse. Derpy immediately grabbed a stale blueberry muffin and nibbled on it. They may have been vastly inferior to her own, but Derpy was still happy to have muffins.

“Feeling better?”

“A little. A shower helped. I feel kinda queasy, still.”

I nodded. “Well, have a bagel or two. It’ll help settle your stomach. Won’t do a whole lot for your hangover, though.”

Derpy rubbed her temples. “It’s like my head’s being pinched by a giant crab.”

“Yeah, you had quite a bit more to drink than me. I think I got off a little easier.”

She groaned tiredly. “I think I want to stay in bed for a few hours.”

“Well, I was going to go to the Stable. Once Crook gets his hooks in me, he’s gonna want to talk for a few hours. Want me to do that while you rest?”

Derpy’s eyes shot wide. “Nonono, you have to take me. I’ll sleep on the train when we go back. I don’t want to miss seeing Crook.”

“Are you sure? You seem pretty… haggard from last night.”

She collapsed onto the table and whined pitifully. “Ugh, I know… but I still want to go.”

“Okay, just don’t push yourself too hard.” I took a big bite of an onion bagel. Bland, and unsatisfying.

“Okay, mom.” She shot me a false look. It quickly dissolved into a smile. “I had so much fun last night, Guilty. This was a great idea.”

‘Last night.’ “Well, I’m… glad you had fun.” ‘Don’t bring it up.’

“I’ve never done anything as crazy as that before.” She blushed.

“You mean… outside?”

Her blush intensified. “Yeah… it was really scary… but kinda really fun, too.”

‘Don’t bring it up.’

“Yeah, and I’m…”

‘Don’t bring it up, Guilty’

“I’m really sorry… about… about…”

‘Make something up, you fucking putz. Backpedal!’

“… about what I said. I was drunk, and…”

‘Oh, fucking bra-vo. You mook.’

She smiled.

And it burned. Her sad eyes, her calm attitude, there was a glaring emotion in her actions.

“It’s okay, Guilty. Don’t worry about it.”

It was pity in her eyes. Acid pity. I was weak. I was a weak tiny thing that had attached myself to her, and she would sweep me aside with pity in her eyes, for I was pitiable.

“It’s just… I mean…”

She was looking for the words that would hurt me the least. The words that would make the act of letting me down as gentle as possible. Time was slowing down. I could feel my heartbeat. The hairs on the back of my neck stood on end. For some impossible inconceivable reason, my body was on full alert. I was hyperaware of my surroundings, as though my body wanted me to hang on every wicked painful, razor syllable of Derpy’s inevitable “let’s just be friends.”

“I’ve never said that to a pony other than… well, you know.”

Drowning on dry land. All my false ideas of what this relationship was and fictional hope for a stable relationship were suffocating me. I could breathe, but it was almost like I didn’t want to. I couldn’t look at her anymore. I just stared into my bagel. Why had I brought it up? Why had I even said it in the first place? Why had I brought Derpy to Manehattan? Why had I ever tried to date her? Why had I ever even left Manehattan?

“And I just…”

I left to get away from this. I left to get away from this exact feeling. I left to escape this caustic, scalding pity that had burned me so very badly. I left so that I wouldn’t have to feel so small and weak and… nothing. I left to be free of this.

And it had followed me. It had followed me to my little backwater burg. It had followed me to my little cabin where I could pretend that heartbreak didn’t exist and it waited. It waited for me to get my hopes up again so that it could crush me while I was standing happy and tall.

“I think it’s going to be a while before I can… say those words.”

‘Wait…’

‘That’s… that’s different.’

‘That’s not like last time.’

“I mean I know it’s… it’s something that’s really big in a relationship, but…” She had tears in her eyes. “But it’s just...”

Gear change.

That hyper-awareness had paid off. I’d caught something that changed the context of the whole situation. Derpy wasn’t casting me aside. I hadn’t gotten too close. I hadn’t made things too real. This was something else.

“It was the last thing that…” She sobbed hard. “It was the last thing I ever s-said to him.” Tears rolled down her face. “Sorry, I… I didn’t mean to cry.” She hid her face behind her hooves. “I… I was trying r-really hard not to cry last night, I’m sorry.”

I stood there dumbfounded. It wasn’t pity that I’d seen in Derpy’s eyes, it was… something else, something much more complicated. Shame and nostalgia and melancholy and even a little pride were all rolled into Derpy’s own personal little private pain.

This… wasn’t about me at all, at least not in Derpy’s eyes. To her, her inability to reciprocate was her own shortcoming. I’d had it all backwards. I didn’t need to be apologizing; I needed to comfort Derpy. She had thought that she’d said something wrong.

‘Full throttle comfort. Break out your absolute best. Go go go!’

I stood up, and immediately moved to her side. “Don’t worry. Don’t you worry at all.” I nuzzled her hard, and wrapped a hoof around her.

“I’m s-sorry, Guilty, I just… I was w-worried I’d ruined the trip.”

“That’s what I was worried about. I thought you were upset about what I said.”

“No, it’s fine! I j-just…”

“You don’t have to say anything!”

“O-okay!”

Derpy broke down, crying into my shoulder. Derpy had already cried countless tears over Dusty, but that morning on the twenty-seventh floor of the tiara plaza she cried a few more.

That cry provided me with some much needed perspective on my relationship. I am dating a mare who lost her husband. Derpy has made it clear that I am not a replacement for Dusty, it’s a natural thing to worry about. And while that does make me feel a bit more… appreciated, it also has a fairly simple downside. Dusty is still missed. I am not filling the hole in Derpy’s heart, but that means that the hole is still there.

I will have to consider this fact in future relationship tactics.

Crying eventually stopped and conversation eventually resumed. Derpy was once again very excited to see the stable, and the moment we finished eating, she was ready to go. Derpy cleaned herself up, I took my own shower, and made our way to a place I hadn’t been in two years. Another taxi ride got us there quick enough. We made our way past crowds of busy ponies to The Cherry Smile, my old home.

The Cherry Smile occupies the bottom two floors of a thirteen story building. It has an unassuming entrance, not unlike a traditional pub. No sign or awning, just a simple wooden door.

“Here we are,” I said, opening the door for my girlfriend, like a good little stallion.

“This is it?” Derpy asked, unbelieving. Surely this simple wooden door couldn’t lead to a house of pleasure.

“This is it,” I assured her.

Once inside, one is promptly met with a second, much sturdier door, accompanied by an equally sturdy stallion. I recognized the stallion on duty, and he me. “Holy shit…”

“Hey, Deadbolt.” Pure and unfiltered nonchalance. I am a dick.

“Fuck you and your ‘hey.’ I didn’t think I was evah gonna see you again.” The burly pegasus offered me a large stallion-hug. “Holy shit, Guilty.”

Deadbolt has been working as a bouncer and general security guard since about when Crook started working as an Escort. We were never that close, but he’s always been a friend. “Deadbolt, this is Derpy.”

“Hi!” Derpy eagerly grabbed his hoof and shook it. “I’m his girlfriend!” she announced cheerily.

He shot me a surprised look. He knew I was never one to date. “Well, it’s a pleasure to meet you. You two can head on in.”

“C’mon, Guilty, I wanna say hi to Crook!” She was giddy again, her hangover apparently waning. She strolled into the stable ahead of me.

“She knows Crook?” Deadbolt asked.

“Yeah, he came down to visit me a while back.”

“Ah, so that’s where he vanished to,” he said, rubbing his beard.

I swallowed. “So uh… is she home?”

Deadbolt shook his head. “Nah, she’s out today. Should be back around business time. Try not to stick around too long, aight?”

I nodded, and gave him a friendly pat on the shoulder. “You’re a real good friend.”

“Hey, it’s my job to keep things quiet around here.” He gave me a pat back. “Good to see you, Guilty.”

“You too.” I followed Derpy into the stable’s main room.

The first room in the stable is really a showroom. It’s where all the sexy stallions and mares of the stable can “display their wares,” as it were. Most of the interior is red velvet and leather and gold trim. Across from the entrance sits a very well-stocked bar. Drinks aren’t cheap, but that’s the price of even being in the showroom. In one corner there’s a small stage with two stripper poles on it. There’s lots of room in the middle to mingle, and some big, high-walled booths along the edges of the room. I spent many nights working this floor. Flirting and dancing and seducing. Bringing in the bits. Earning my keep.

I’m actually quite an accomplished pole dancer. I should get one for my cabin; I don’t want to get rusty.

However, mid-morning was not when downstairs was alive with hormones and sweat and promises of pleasure. A janitor I didn’t recognize was sweeping in a far corner. A gofer behind the bar was wiping the dust off of the liquor bottles. The jukebox played some light jazz. It was a very quiet morning for the stable.

“Oh my gosh, this place is so fancy,” Derpy commented, drinking in the scenery. Even in its off-hours, it was quite a room.

“Well, it has to impress, Derpy.” It felt… somehow good to stand in that room again. It was just so… easy to be… home. Part of me thought it would be awkward to stand here and remember everything that happened, but it just felt… familiar.

“My my my, is that who I think it is?” I turned to the far end of the bar and noticed an old acquaintance. “Guilty Pleasure, the prodigal son.” Spectacle was a reserved pony. He had a collected demeanor that betrayed his intelligence. A rather tall, thin stallion, Spectacle had been a professor at Celestia’s School for Gifted Unicorns. Years ago he’d been forced to resign after a plagiarism scandal. One way or another he found his way to The Cherry Smile, years later.

Spectacle is a sort of specialty stallion. He doesn’t have many clients, but the ones he has are fairly loyal. See, Spectacle is smart… like really really smart. Not the sort of quick and clever that lets an average escort appear to be a master of everything. No, spectacle is truly a brilliant stallion and scientist. Before his untimely retirement, Spectacle made a number of breakthroughs in the field of Applied Magical Theory. He’s written three books, and dozens of articles over a long career. He caters to the clients that are actually too intelligent for a normal escort to keep up with.

I should introduce him to Twilight.

“What does prodigal even mean?” I asked, knowing he would have an answer for me. He knows all the words.

“Lavish to the point of wasteful. Colloquially, though, people simply use it to mean absent.”

“I missed having someone who can actually answer questions like that.” I sat down on the stool next to him. He was drinking a martini. “How’s life, Specks?”

“Now now, Guilty,” he chided. “I’m doing you the common decency of using your pseudonym, which I know you prefer.” He took a delicate, yet purposeful sip of his drink. “It’s not too much to ask that you do the same, I should think. And while you’re minding your manners, would you do me the honor of introducing me to this lovely mare?”

“Sorry Professor.” He tended to insist that everyone call him that whenever he was on the ground floor, whether customers were present or not. “I’d forgotten… decorum,” I said with no small amount of snark. “Professor, this is my lovely girlfriend Derpy.”

“Hi!” Derpy grabbed his hoof and shook vigorously.

“Derpy, this the Professor. He’s an old friend.”

“Charmed,” he said politely. “And thank you, Guilty.” He caught the attention of the gofer behind the counter. “Marble, you’ve been learning to mix, lately, right?”

The gofer turned and wordlessly nodded. He was a young Earth Pony, maybe fifteen.

“Make my friend here a manehattan.” Lucky for Spectacle, only clients had to pay for drinks. He noticed that his own drink was very close to empty. “And make me another martini as well.” His attention turned to Derpy. “Can I get the lady anything?”

Derpy’s face showed a hint of a frown. She was still feeling her hangover, the idea of more to drink didn’t exactly sit well with her. In fact, I think she wasn’t all too keen on the idea of having a drink this early in the first place. “No thanks.”

The young boy obliged, and began to prepare our libations. “So tell me, Professor, how have things been around here since my departure?”

Spectacle swirled the last vestiges of his martini in the bottom of the glass. “Well, you leaving left quite the client vacuum. I didn’t personally wind up shouldering any of your load, but several of your regulars were snatched up by the others. We’ve had quite a few revolvers. Two new more permanent escorts. In fact, one of them—”

“What’s a revolver?” Derpy asked abruptly.

I answered for Spectacle. “Somepony who doesn’t work for very long. Just a month or two at the most. Usually it’s somepony who’s escorting as a last resort.”

“Why do you call them revolvers?”

This time, Spectacle answered for me. “Because it’s like a revolving door. Ponies come in, ponies go out.”

Derpy cocked her head. “But… can’t you go in and out of a regular door?”

Spectacle merely squinted at her. “I suppose you can.”

Derpy just giggled. “Guilty, I’m gonna go look at the jukebox. I wanna see what songs it has.” And with that, she happily trotted across the room, and began investigating the giant appliance. She was so cute, eager to learn everything she could about my old home.

“Not too bright, is she?” Spectacle commented the moment she was out of earshot. Spectacle’s always had some deep-seeded prejudice towards ponies whom he deems “unintelligent.” It’s gotten him into trouble more than once.

I felt my temper flare for a moment. A flash of white hot fury. “Careful,” was my only response.

I must’ve sounded quite threatening, because his ears shot up and his eyes went wide. I’ve never really known myself to be intimidating, but his reaction was very satisfying.

“Yes. Of course. So sorry.” He cleared his throat. “Ah, here we are.” The gofer served us our drinks. Spectacle seemed happy for a change in subject. He raised his glass and I followed suit. “To homecomings.” We clinked our glasses and drank. It was a good manehattan. I smiled to the gofer.

“So, do tell me, Guilty, where in Celestia’s Equestria did you disappear to?”

“Somewhere you’ve never even heard of. Way out in the boonies.”

Spectacle seemed to accept my non-answer. “Never pictured Guilty Pleasure in a small town. Are you still in the business, or are you a farmer now, or something?” He laughed at the thought.

“Yes, I’m still an escort. In fact, I’m the only game in town.”

He chuckled. “Well well, good for you.”

An awkward silence filled the air. I decided to break it. “So… how has Ms. Smile been.”

An eyebrow raised. “Ms. Smile, he says. And I thought you were one of her little adopted children. When did you stop calling her ‘mama’.” He chuckled devilishly. “Forgive me, I never cease to find entertainment in other ponies’ drama.”

“I guess I grew up,” I responded. It wasn’t a practiced line, it just sort of came out.

“Indeed so.” Another sip for Spectacle. “She’s been fine. In fact, she insisted nothing at all was wrong when you left, but I think everyone knew better. Your leaving hurt her, Guilty. You were like a son to her.”

I found myself hanging on his words. I’d had no real news of Ms. Smile since I left. This was old hat to him, but I was eager for the ancient update.

“For a time, the name ‘Guilty’ was somewhat taboo. Anyone who said it would magically receive punishment for some unrelated slight.” He snickered. “Oh, poor Nightcap was stuck on gofer duty for a week, one time.” He released a relaxed sigh. “But… time went on. Things went back to normal. Crook hasn’t been quite the same, but I’m sure you noticed that when he came down to visit. So morose.”

I kept myself from cocking my head. I hadn’t noticed a single thing different with Crook when he’d come to visit. He was exactly the same. It was as though time had stopped when I left. He’d been the same loud, inappropriate, shameless Don Juan of a stallion I’d always known.

“Things are largely the same, by now. She’s stern, but caring to the whores, and flirtatious with the guests. Same old, same old.”

I was… underwhelmed. I’m not sure what I was expecting to hear, but there was just so… little news. Perhaps it’s just ego, but I thought my leaving would’ve left a bigger sort of impact, but… it looked like everypony had already recovered.

Is it bad that I almost wish they hadn’t? Whores come and go all the time, even the more permanent ones, but… I suppose I’d always thought that it would’ve been… different with me. I suppose I just felt like I should’ve been more… missed.

But, I wasn’t. Everypony had just... adapted to my absence.

I mean, it made sense. It had been two whole years. But… but for me I guess it sort of felt like my old life would be waiting for me. Ponyville was a… separate life. I had gone to start fresh. I guess in doing so I sort of never realized that my old life would… leave me behind.

Spectacle’s eyes caught sight of something across the room, and in an instant, he grew an impish smile. “Oh-ho-ho… this will be splendid.”

“What?” I followed his gaze to a young stallion across the room. An Escort for sure, I recognized his swagger. He was making his way over to the bar; he’d caught sight of me and Specks. He was a young thing, maybe twenty… twenty-one at the most. A greyish mane, a red coat, he sort of clashed, but he wasn’t too bad looking. A bit on the small end, for an Earth Pony, but who am I to judge?

It was his mistake, honestly. He should’ve gone and talked to Derpy. She was an apparent client, and was currently not being entertained. Had I still worked there, I might’ve chided him.

“Professor, who’s your friend?” the young escort asked. He had a high voice, sort of nasally. He was rather feminine, truth be told.

The Professor smiled widely. “Just an old friend who happened to be in town.” He very purposefully turned his attention to me. “Allow me to introduce you to my co-worker.” He once again made a very purposeful gesture and indicated the young stallion.

“This is Guilty Pleasure.”

I paused. “Hello…” I said absently.

He extended a hoof. “Hi, it’s nice to meet you.” He was jovial, friendly, a perfect gentlecolt.

I absently shook his hoof. I was still in shock.

“And you are?”

“Pumpkin Bread.” My pseudonym was an automatic response. Ultimately, it was for the best. It put me in the act. The act allowed me to focus. “It’s a… pleasure.”

‘Did I… did I just do that?’

The stallion… uh… Guilty, waved off my obvious faux pas. “Don’t worry about that, it happens all the time.”

‘I know that! You don’t tell me that I tell you that. That’s my line!’

“So, Mister Bread… or can I call you Pumpkin?”

A textbook approach. Appear overly polite to put your target at ease. Amateur.

I wanted to… needed to keep him talking. I had to know… everything about… my…

… replacement.

“Pumpkin’s fine. So tell me about yourself. Work here long?”

“About two years now.” ‘Fool, you could’ve easily withheld that information to find out more about me. You know nothing of sleuthing.’ “I love it here, you meet all sorts of interesting ponies.” He smiled warmly. “So, are you here meeting someone, or…?” His hoof casually found the back of mine. When had that happened? I missed his movement. I missed his movement. It must’ve been a flawless physical approach. Maybe he wasn’t a complete scrub.

His touch was like… slime on my skin. Masculine imagery assaulted my mind. My response was less than favorable. I recoiled violently. “Nooooo… no-no-no-no…” I was visibly frazzled.

His expression turned to one of shock. “Oh… oh I’m so sorry.” He recoiled in kind, purposefully put distance between us. “You were talking to The Professor, so I just assumed…”

I took a breath. “It’s okay… I just…” I swallowed hard. Harder than I really intended. Spectacle took notice of my behavior. “I wasn’t expecting it.”

A concerned voice came from somewhere behind me. “Guilty, are you okay?” Derpy had finally returned from the jukebox, just barely in time to see my miniature freakout.

I did not have the opportunity to respond. “I’m fine but I think my friend here might need another drink.” The new Guilty turned to the gofer behind the bar. “Marble, get him some water, would you.”

“That won’t be necessary, thank you.”

Derpy looked back and forth between the two of us, a quizzical look on her face. After a moment of silence, she finally responded. “Huh?”

“That said, it’s so good to see you again,” he said almost nervously. A poor play on the New-Guilty’s part. He’d assumed Derpy was a client he didn’t remember.

She obviously recognized him. Or at least, that was his perception. He didn’t even follow it up with a “How long has it been?” in an attempt to determine when they had met, to try and jog his memory. I am twice the escort this stallion is.

I could hear Spectacle giggling under his breath. He was loving the farce playing out before him.

Derpy spent another moment in baffled silence. I myself was looking for a way out of this terribly awkward situation. Derpy looked to me for help. “What… what is happening?”

‘What is my play. Try and play it cool and hope Derpy catches on? She probably won’t. Damnit. Come clean? Okay if I can’t think of a better option in ten seconds we’ll go with that. Stall? Maybe. Let Spectacle deal with it? Ooh, I like that one.’

“Sorry, Derpy, I’ll be right back. Professor, be a dear and introduce this charming man to my lovely girlfriend, hmm?” I shot him a disingenuous smile, which he mirrored with his own satisfied smirk.

“Anything to keep this conversation rolling, Pumpkin.” He waved playfully as I hurried to the bathroom.

I didn’t actually need to do anything, I just needed a moment to collect myself. Assess this… situation.

‘Okay so… I have been… replaced. There is a new Guilty Pleasure in the stable.’

I splashed some water on my face. This felt weird. This was all wrong. I just wanted to sneak in, show Derpy around, say hi to Crook and vamoose.

‘It’s not a big deal. Guilty Pleasure is a kick-ass name. It’s obvious it would make it back into the mix eventually. He’s not even really your replacement. The stable sees a dozen new employees a year. People come and go, no one’s getting replaced. He’s just using your old name.’

But that was the thing. It wasn’t my old name. That was still my name. I was still Guilty Pleasure. Not him.

‘Two ponies can have the same name. In middle school there were two stallions named Brickhouse.’

That… sort of helped. Okay my identity crisis was postponed. Now I had to deal with the immediate awkwardness of New-Guilty.

‘My best bet is to shoo him away. Spectacle isn’t going to make that easy. He lives for this drama. He’s like a proactive gossip, making juicy situations himself so that he can talk about them to everypony. This is going to have to be elaborate.’

I shook my head. I was thinking too hard. This was actually catastrophically simple. I just had to take my leave and go say hi to Crook.

I returned from the bathroom to Spectacle smiling like a jackal, New-Guilty attempting to tell Derpy some amusing anecdote, and Derpy looking profoundly uncomfortable. Time for a rescue.

“Heeeeeeey,” the classic extended hey is a great way to stop someone else from talking. “Sorry to interrupt, but, Derpy and I should really be visiting with our friend Crook right now. That’s kind of why we’re here today.”

Spectacle began to pout, but New-Guilty maintained his ever friendly aura. “Hey, no problem. You know Crook?”

“Yeah, Crook and I grew up together, actually. We go way—”

“Guilty.”

I froze as ice shot into my ears and down my spine. Instinct kicked in and I snapped to attention. I turned to greet the matron of the fine establishment where I once worked.

Mama was home.

“Stop talking to yourself and meet me in my office. Now.” Quick and sharp as ever. She stood tall and proud and powerful. She was dressed in fur and long boots. Voluminous red hair, rich full red lips, she was a mature and refined beauty.

That’s really just a nice way of saying that she’s still sexy even if she’s getting on in years.

Ms. Smile, as I’ve sort of explained, is essentially the closest thing I ever had to a mother. When I was very young, Crook and I got jobs as gofers, and effectively became two of Ms. Smile’s children. Ms. Smile takes in wayward youths like other ponies purchase hats, but that’s not to say she doesn’t care for every one of them… of us.

Ms. Smile taught me more about the world than school or my father ever did. She taught me to dance, taught me to mix drinks, taught me the fine art of conversation. Etiquette, seduction, even basic mathematics. She is a master of many trades.

Or at least she appears to be. A true escort’s escort.

I’ll admit, I was always something of a… teacher’s pet. And I like to believe that I was something of a favorite. The bond that I share… shared with Ms. Smile is one that most ponies don’t get to experience in their lifetime.

“Don’t dawdle, Guilty,” she said as she quickly stepped towards her office on the far end of the stage floor. Her cutie mark stared at me as she passed. A big eye with a heart instead of a pupil.

New-Guilty instantly responded. “Y-yes ma’am.”

“Not you!” she called back.

New-Guilty was understandably confused. Spectacle was trying and failing not to appear ecstatic. And Derpy looked as confused and concerned as ever.

“I… I should go. Spectacle, please watch after Derpy for me.” He just nodded as he tried not to laugh at my misery. He really is a sadistic son of a bitch.

I solemnly marched off towards mama’s… Ms. Smile’s office. ‘Damnit, Deadbolt. You told me I had some time.’ I stopped when I reached her door. This was not going to be pleasant. ‘Just get this over with. All you have to do is NOT get thrown out so that you can still go say hi to Crook. Very doable.’

I hesitated as I reached for the knob. This was too weird. Why was I even listening to her? It was instinct, I suppose.

I turned the knob. The whole thing was so surreal. I wasn’t even planning on seeing her today. In the end it just came so… naturally. An almost primal instinct. Listen to mother.

I mentally prepared myself for the upcoming battle.

I turned the knob and stepped into her office. She sat in her high-backed chair counting out bits on her desk. Her expression was… unreadable. It always is. She has a near-perfect pokerface. “Guilty, you’re looking well.” She didn’t look up from her task. Her attention stayed fixed on her coins.

“Hello….” I paused. That was a mistake.

“Still not sure what to call me? Poor thing. What an awful internal struggle that must be for you.” Her tone was biting.

I didn’t have a response. Rather, dozens occurred to me, but silence still seemed like the best option.

Conversations with Mama…

…with Ms. Smile….

… are like chess. Every line, every word, every gesture must be carefully considered. She taught me everything I know about conversation, and when it comes to words, she is a grandmaster.

I had to get myself in the zone. Had to psych up for the mental sparring I was about to perform.

“Sit,” she commanded.

I tactically obliged. No point in just outright appearing defiant. An easy first move.

She finally looked up from her task. “It’s good to see you again, Guilty.” She appeared earnest, not that that meant much. She’s an excellent actor.

Again, I played along for now. “It’s good to see you, too.”

She smiled. Was that actual relief? Best assume it’s calculated. “So, tell me… how is… Ponyville? That’s where you moved, yes?”

“Yeah— yes,” I correct myself instinctually. She abhorred improper speech. I mentally chastised myself for being so… conditioned. “It was really just… somewhere out of the way.”

“Hmmmmm…” she continued counting out bits. “So what brings you back… with a girlfriend, no less? Her eyes are interesting. I imagine she’s sensitive about them. Did she start out as a client? She must’ve, the way you are.” She smiled to herself. “There’s more than a small amount of irony in that, isn’t there.”

I was flabbergasted at how quickly she’d taken control of the conversation. She’d gathered so much information in the seconds she’d seen Derpy and I at the bar. Her powers of observation never cease to amaze me.

See, Mama and I… Ms. Smile and I… actually share a unique bond.

She and I have the same special talent, or very nearly. Hers has always felt a bit… stronger than mine, for lack of a better expression. At times it seems like she can just see… everything. Everything within you that should be yours and yours alone is laid out before her. She sees the core of you… what you want… what you need…. who you are at your very center. It can be… frightening.

She’s always described as “being able to figure out what ponies want”, but I swear it’s so much more than that.

I swallowed. She’d already rattled me. “I… yes… she was… still is… a client.” I needed to gain traction before she said something else. “Things have been going well. Business is good.”

“I’ve noticed.” Once again she returned to counting her bits. I was sort of curious what she was even doing.

“I’ve got a nice little clientele. No competition.” Just keep things moving until you can develop a strategy, Guilty.

“You didn’t answer my question,” she stated with a hint of smug satisfaction. “You should never leave a lady waiting, Guilty. Has everything I taught you already fallen out of your head?”

I fought back a snarl. This is how she acts when she’s upset. Pleasant, but backhanded. She changes gears and makes it hard to keep up with her emotional and mental pace.

“What question was that, again? I must’ve missed it.” Rather than excuse my error, I’d just cop to it. Take away the power of her statement, by appearing not to care.

“What brings you back to Manehattan?”

“Derpy wanted to see the city. I wanted to see Crook, and get some decent pizza.”

She stopped in her tracks and looked me dead in the eye. “Is her name really Derpy? And I thought your father was a cruel parent.”

“Don’t…” I intoned. I’m not sure I wanted to talk about less, Derpy or my father. Either way, I was putting a pin in this line of questioning.

She looked apologetic for just a moment. “I’m sorry, Guilty. I know he’s off limits.” I wasn’t expecting her to respect my boundaries, given that we were sort of at odds at the moment. That said, I’m happy she did. “In any case… it is good to see you again. I mean that.”

It was the truth. I knew it was.

“I…” I fumbled. I couldn’t decide whether or not to respond in kind. This was weird. The things she said when we’d last spoke. The things I said. How was she happy to see me.

“And you’re… not… happy to see me, it would seem.” She steeled herself. No emotion, no witty retort, no nothing. Was she really hurt? Surely this was an elaborate act.

“No, it is—”

“Don’t lie to me, Guilty. You know you can’t anyways.”

It was true. Both Mama and I could absolutely perceive each other’s lies.

… Ms. Smile and I…

“I… I’m sorry I just…”

“No need to excuse yourself. I was rather horrid to you when last we spoke.” She proceeded to gather up the bits she’d counted out and place them into a small bag. There were quite a few of them. Easily a small fortune. “Either way. This belongs to you.” She pushed the bag across her desk. She was acting strange. Almost like she was in a rush. It wasn’t like her. She never rushes. The world moves at precisely her pace at all times.

I sat bewildered for a moment. “I’m sorry, what?”

“Guilty... you never were very good at math.”

“I’m aware.”

“Well, when you walked away from me with a bed that was half mine we agreed you’d be paying back that other half with interest, correct?”

“Correct.”

“Well, it would appear that, while you managed to learn your times-tables and how to add and subtract. The finer points of mathematics, such as the concept of compound interest, continue to elude you.”

“Okay…” I was trying hard to keep up.

“The point is… interest accrues on the current balance… not the principle amount.”

“…okay…”

“You overpaid.”

“I… overpaid?”

“Your debt to me… it’s been paid off for two months and you’ve continued to send me bits.”

“Oh… so you mean…”

“You are no longer beholden to me, Guilty.”

“Okay… wait… ”

“Anyways I should be leaving… I’ve kept a handsome stallion waiting on me for far longer than he anticipated.” She rose to leave. “If you please…” she motioned toward the door.

I was still playing catch up. I was done? Done? I’d paid everything off? Surely not. I’d done those calculations a dozen times to make sure I paid her back.

“Guilty… out!” She was mad. She never liked to appear mad. She was always in control.

I obliged. A mad Madame was a scary prospect. The moment I left her office she walked briskly past me. Derpy, New-Guilty, and Spectacle watched her go, the latter two with mouths agape. Her mood was not lost on them, either.

I rejoined them at the table. Derpy immediately put a comforting hoof over my shoulder. “Guilty… what on Earth happened.”

New-Guilty was next to speak. “They filled me in. Sorry to… spring your own name on you… that’s gotta throw you for a loop.”

“It’s fine,” I responded, still not entirely present.

Spectacle had a wicked look in his eye. “Guilty… tell me everything… I’ve never seen that woman so flustered.”

“I… I think I hurt her feelings…”

“Details, Guilty, details.”

“I think Derpy and I should go see Crook now.”

“Oh Guilty, you’re no fun anymore,” he pouted.

“Let’s go,” I said to Derpy. She nodded and followed me to the stairs.

So, the Cherry Smile more or less has three sections. There’s the front, the showroom with all the nice furnishings, the face of the business. Then there’s the back, all the private rooms where the real juicy parts of the business happen. It’s just as pristine and extravagant as the front, if not more so. Then there’s the way-back. The way-back is far less nice than the rest of the establishment. No nice carpet, no fancy wallpaper. It’s where the escorts live and sleep. Fairly modest accommodations: cheap bunks, painted floors, a shared bathroom.

On the plus side, as long as you were working you got to stay in the fancy rooms.

“Guilty… what’s going on? What’s that bag?” Derpy caught up to me on the stairs.

“It’s uh… a ton of bits.” I kept walking.

“Guilty… hold… hold on a minute!” She grabbed me by the shoulder, stopping me in my tracks. “Guilty what just happened? Who was that mare? Why did she give you… Luna, how much money is that?”

“I… I dunno, I didn’t have the chance to count it.” I rubbed a hoof down my face. “I’m… I’m still playing emotional catch-up.”

She wrapped a tender hoof around me, and pulled me into a nuzzle. My nervous panic evaporated. “Guilty, talk to me. What’s going on?”

‘Where to start? Obviously not with the whole accessory-to-blackmail thing.’

“Okay so… that was Cherry Smile… as in the owner and proprietor of the Cherry Smile, Cherry Smile.”

“Professor filled me in on that much. He said that the two of you go way back.”

“Yeah she… she’s sort of the closest thing I ever had to a m-mother.” I swallowed. Was I starting to choke up? I steadied my breathing. “I’ve, uh… been paying off a debt to her since I left Manehattan. Apparently I… miscalculated my debt. She paid me back what I overpaid.”

“Oh… was… was that all?”

“… I don’t know…”

“What?”

“I just… I said something… or rather didn’t… and it really got to her.”

“What did you say? Or… didn’t say?”

“She said it was good to see me and I… I didn’t respond in kind.”

Derpy paused. “…wow…” Dripping with judgement.

“What?”

“I just… you said she was like a mother to you.”

“I know… it’s just… complicated.”

“How?”

I couldn’t really tell her about why I left the stable… about everything that happened between the two of us. “It… It’s just that… we didn’t part on the best of terms… and I was hoping not to bump into her today. She still holds a grudge for my leaving Manehattan.”

“I… Okay.” I was about to continue walking when Derpy interjected again. “But she said she was happy to see you. She can’t hold that much of a grudge right?”

“I…” I didn’t have a response to that. It was pretty sound logic. “I guess,” was all I could manage.

“You could’ve just said it was nice to see her.”

“She would’ve known it was a lie.” I grimaced. “Do we have to do this right now?”

“I’m just trying to…” She stopped herself. She’d gotten a little heated. Derpy puts a lot of emphasis on family, and apparently she didn’t like what I had to say about my adoptive mother. “Okay, you’re right; we’re here to have fun.”

We continued into the depths of the Stable. More than the pizza, more than the crowds, more than anything else so far, this felt familiar. This felt like home. I spent close to thirteen years of my life in these hallways, working and earning and just… living. I came to our room, the room that Crook and I shared ever since I turned eighteen. I pushed open the door; the lock has been broken forever, and still hasn’t been fixed, it would appear.

The room hadn’t changed at all. Sure, the mess was a different mess, and the stains on the counter were different stains, but the place was still the little hovel I knew and loved. The only difference I could see was that the two twin beds weren’t pushed together anymore. I could see Crook asleep in one of the beds at the far end of the room.

Derpy almost tripped over what appeared to be a discarded pizza box. “Watch your step,” I absently warned.

“Oh my goodness, it’s a pig sty.”

“Yeah, there’s not a soul alive that can clean faster than Crook can mess.”

“Can I help you?” came an accusing voice from within. I hadn’t noticed the pegasus on the other bed under all the covers. Some newbie. Crook’s current roomie, it would seem.

“Sorry, I’m here to see Crook.”

He rolled his eyes. “He’s sleeping. I’ll take a message.” Good old Manehattan charm.

Time to fight rude Manehattanite with rude Manehattanite. “Yeah, I’m coming in.” False bravado. Play the tough guy. That’s what this city is all about. I shouted at Crook’s massive sleeping frame. “Crook! Wake up ya fuckin’ animal.”

“You asshole. They just went to sleep. Don’t poke the bear.”

“They?” I asked before immediately receiving an answer.

“Who’s yelling…?” whined a mare’s voice. A cute blue bob-cut, and a tan coat peaked up over the massive heap that was Crook. “Guilty? Oh my gosh, is that you?”

It took a moment for recognition to kick in. “Plume?” My manehattanite client from a while back. “How… how do you know Crook?”

“Oh… I… I’m a client… sometimes. Sometimes just a… friend. What… what are you doing here?” She rubbed the tiredness from her eyes.

Crook’s roommate responded before I could. “Apparently ruining my quiet morning.”

I rolled my eyes. “Came to visit Crook. He’s an old friend.”

Plume grinned. “Yeah, he talks about you a lot.”

I smiled back. “Does he now?”

“Yeah…” Still such an awkward creature.

“Well, it’s really nice to see you. This is my girlfriend, Derpy.”

“Oh… I didn’t realize you were dating. That must be… weird. No offense, I’m just saying… nevermind.”

Derpy smiled. “It’s nice to meet more of Guilty’s friends. He doesn’t have nearly enough.”

I gasped so as to feign hurt.

Derpy stuck her tongue out at me. “What? It’s true.”

Plume tittered at us. “You guys are goofy.”

“Thank you,” I responded, which earned me another giggle. “Anyways, I’d like to wake up the big lug.”

“Oh sure.” She shook the massive stallion’s shoulder. “Hey babe. Wake up. You’ve got a visitor.”

Crook groaned in response. “Too early.”

I couldn't help but take pleasure in his torment. “I know any time before noon counts as ‘too early’, but wake your ass up, Crook."

His head turned to face me and his eye pried itself open. “Guilty? What the fuck?” came his tired response.

“Stand up and give me a hug, you fuck.”

Crook twisted himself upwards and managed to pull himself off of his bed. “The fuck you doing here?” He stumbled over to me and gave me a hearty squeeze. I returned the affection in kind.

“Now you know how I feel. Let’s go get pizza.”

Crook pulled away to look at me. Still bleary-eyed and half-asleep, he responded. “Yeah, okay.”

“You coming, Plume?” I asked reflexively. It was only polite, I had interrupted her slumber.

“Oh, um… sure. I’m just about awake at this point. Barely slept.” She followed Crook off of the bed, and sidled up next to him, offering him a swift nuzzle.

I turned to Crook’s roommate who had wrapped himself tightly in his sheets. “What about you, sunshine? Hungry?”

“Get fucked,” he kindly responded.

Down the stairs and out the front door we went. Deadbolt offered an apology as we left. He had no way of knowing that she was going to be back in the middle of the day for a quick check-in. I forgave him; it was hardly his fault.

Only once we were outside did Crook really start to wake up.

“Okay so… this ain’t a dream, right?”

I chuckled. “No this ain’t a fuckin’ dream. I’m here, ya big moron.”

Derpy laughed. “I love your accent.” I hadn’t realized I’d slipped back into it.

“Okay then, you’re here. Why are you here?” Crook had some serious mental catchup to do.

“I came to show Derpy the sights of my hometown. Not to mention say hello to my fuckin’ brother.”

“How is that mare?”

“Why don’t you ask her yourself? She’s standing right next to you.”

“Hi Crook. Awake yet?” She had such a shit-eating grin in that moment.

“Not awake enough I guess. Good to see you, gorgeous.” He rubbed his eyes. “Ah shit. Where’s Plume? I didn't leave her with fuckin’ Hurricane, did I?”

“She is standing right here. Next to me.”

She waved while trying not to laugh. “Hey, babe. You okay?”

Crook waved his hoof back. “I’m fine, I’m fine… just too early for this shit. You said somethin' about pizza, right? I’m assuming you’re buying. Cause I’m assuming I’m broke.”

Plume responded. “Yes, you’re broke. You spent what you had on drinks with me last night.”

Crook nodded. “Sounds like me.”

Crook has never been one to save money. He spends what he has the moment he has it.

“Yes, I intend to pay. There’s enough of us I can just get a full pizza.”

“Mushroom on half for Guilty and me,” said Crook.

“Just cheese for me,” said Plume.

“ME TOO!” screamed Derpy. We’d settled on an order, apparently.

Unfortunately, Hardy’s was a bit of a walk, so we just went to a little place called the Brickfire Pizza Company. It’s great but not Hardy’s-great. Still better than anything Ponyville has to offer.

So a little double date ensued. Nothing particularly remarkable happened. Crook and I caught up. He told me about his new roommate, some of the goings on in the stable. I asked about the new Guilty, to which Crook responded. “Meh, he’s okay.”

Plume was a treat. Eager to talk to me. Very happy to see me. It would seem I’d left quite the impression on her. She asked me how I was, if business was good. I asked her about her writing and how she came to meet Crook. A client-turned-friend, it would seem. Sometimes she pays, sometimes she doesn’t.

Derpy was also happy to see Crook. When she told Crook that we were dating now, he just laughed. Plume and Derpy got along pretty well, too. They liked to chat about Crook and me.

The pizza came and I once more experienced pizza nirvana. Derpy mentioned that she liked the Pizza at Hardy’s a little more because she is a rational pony with a functioning mouth and any sane pony would agree with her.

“So, you two spending the night here? I can kick out Hurricane and you can share his bed,” Crook said through a mouthful of pizza.

“We’re actually headed home soon. Gotta get to Ponyville in time to pick up Derpy’s daughter from the sitters.”

“You got a kid?” he asked in shock. “Did I know that?”

“I think so,” Derpy replied. “I probably mentioned her at some point.”

“Well, next time you come down, you’re both spending the night. No argument. I won’t have my brother spending the night in the hotel when he’s got family right here.”

I could sense Derpy’s hesitation.

“We’ll talk when I come back. Next time it’s your turn to visit, right? Announce yourself before you come.”

Crook had a lewd response. “Meh, I’ve always had trouble figuring out when I’m gonna come. That’s why it’s inside so much of the time. Right babe?” He gave Plume a nudge.

She blushed hard.

Derpy couldn’t help but laugh. “Crook, you’re a riot, you know that?”

“That’s what the cops always say. ‘Incite’ one thing, and suddenly you’re a rabble rouser,” he joked.

“Like you’ve ever been caught,” I responded.

He just smirked at me.

“Well, we oughtta get going. Good seeing you, bro.” Big stallion-hug.

“You too… stay longer, next time.”

“Next time,” I assured him.

And with that Derpy and I bade farewell to Crook and Plume. We caught the train back to Ponyville and made it home in time for dinner. We actually ended up having supper with Lily and Goldy. Carrot soup and grilled daisy sandwiches.

Somewhat... predictable.

Derpy thanked me for a wonderful time, and gave me a big kiss before I left. Dinky made a retching noise to mock our display of affection, as children are wont to do.

It was a nice trip, all told.

A bit… uncomfortable at times, but… it was nice. We’ll probably go again in a month or two.

I’ve… been thinking a lot on… Ms. Smile. I’m not sure… what to think.

Not to mention my liberation from debt. I… I sort of… wasn’t ready to be done with that.

Does that make sense?

I don’t know.

I feel like… I’m still somehow… in her debt.

I don’t know.

I’m going to stop thinking about this now.

Author's Note

It's been so loooooong. I missed writing it was good to finally get all of this written.

Thanks to aquapunkchick, coandco, BlackSkulls, and Jake the Army Guy for editing.

Thanks to all my patient fans for your support and comments. :twilightsmile:

Unpredictable Ponies

My head’s been a mess since Manehattan. I keep feeling like I’ve done something wrong. After my meeting with Ms. Smile, I’ve been feeling sort of guilty about how I treated her. Well, that’s not quite accurate. It was after Derpy asked me about it. She seemed upset at how I’d handled it; about how I wasn’t being happy to see her. Her reaction has me feeling like I was supposed to just be fine with her, after everything that happened.

That’s the thing, though, there’s a long history between me and Ms. Smile. Things Derpy doesn’t know about. Things Derpy can’t know about. Things I don’t want anypony to know about. Because of that, Derpy has no context for my actions. She doesn’t understand… a lot about Ms. Smile and me. I find myself wishing I could tell her about it. Tell her about the whole Sunny Day incident. It would help her understand my relationship with Mama.

With Ms. Smile.

But in doing so, it would open a whole new can of worms. She might understand things, but she’d have a lot more on her plate to digest. A lot more questions. Questions I don’t want asked. Things I’d rather forget.

I say this, but things have actually been fine between Derpy and me. We’re not fighting; there are no awkward silences. It doesn’t seem like she’s even thought about it once since we’ve returned to Ponyville. It’s just a thought that I can’t, for the life of me, shake.

My own paranoia aside, I had a very... interesting Wednesday. Twilight came back. As a client. Her letter was a welcome surprise; I enjoy her company. However, I wasn’t exactly sure what to expect. Her first session was pretty hands-off, but a lot has happened for her since then: a boyfriend, some fights, a nasty breakup. The session could’ve been anything.

I was excited. Twilight was something of a friend. I was happy spend time with her, erotic or otherwise. We just sort of seem to “get” each other, I feel.

It was dusk when she arrived. She was smiling, warm eyes just under her cute bangs. In spite of her cordial demeanor, she had an awkward aura about her. Tense shoulders. Overly purposeful. Nervous.

I began my act. “It’s been a while. Come in.” Warm smile. Smooth movements. “How have you been?”

“Okay.” She sighed, if only just.

‘Non-commital response. Something is obviously on her mind. Wait for her to bring it up?’

I opted to stay in her rhythm. She would talk when she was ready. I matched her pace, her tone, her body language, anything to ingratiate myself. “So, have a seat. Can I get you anything? Tea? Something stronger?”

“What did you have in mind?”

“I have some white wine. It’s not very nice wine, but it’s wine.”

She paused. “Sure. Why not?”

‘Down to drink? That’s a good sign. We may get lucky yet.’

“Besides, I’ve never really been able to tell good wine from bad wine.” She giggled. Her prior anxiousness was gone.

“So, Twilight,” I called from the kitchen. “What brings you? I know you didn’t come all this way for some cheap wine.”

“Well…” she mused. “I’m not one hundred percent sure yet. I was just feeling a little stressed and… you came to mind.” She was very matter of fact. I like that about her.

I feigned a gasp. “So stress and I go hand in hand? Is that truly how you see me, Twilight?” Words dripping with mock pain.

She laughed at that. “You know what I meant. I was just thinking that you’re… a calming presence.”

“That’s good! That’s what I’m all about.” I returned, bottle and glasses in tow. She was sitting happily at my table, eyes glancing around my room. Searching. Learning. Scanning.

She was as cute as ever. It was something about her smile, the way she spoke. She put me in a good mood. “Here we go. Bottom shelf white wine, courtesy of barnyard bargains.”

I was about to pop the cork, when the bottle began to glow with a magenta shine. “Allow me,” she offered. I released my grip on the bottle. It floated away in the glow of her magic.

“Why, thank you.”

“No trouble at all.” The cork made a satisfying pop and the wine began to pour. “What are friends for?”

“Apparently, serving wine.”

She giggled again. “You’re so quick with witty comebacks. How do you do that?”

“Practice. I’ve been doing this for years,” I answered.

“Being witty?” She hovered a half-full glass to me as she poured her own.

“Conversing. An escort does a lot more than… the obvious. I’ve spent what must be years of my life talking to strangers. You get good at that sort of thing after that long.”

She took a sip. With a satisfied nod, the bottle found its way to the center of my table. “I guess I never considered your… tenure as an escort. How long have you been doing… this.”

I took a sip of my own. Yup… it was wine. “Since the day I turned eighteen. Just about ten years ago.”

Her eyes went wide. “I wasn’t expecting that. You were… young.”

I shrugged. “Not so young. It was a job I’d been preparing for for years before that.” I took a deeper sip. “I worked in the stable with my closest friend for quite a while before then. We looked up to escorts. As a teenager they were my role models. Strong, smart ponies who could get along with anyone.”

She frowned. “Your life is so… different from mine.”

I cocked my head. “How so?”

“At that age… I couldn’t even have conceived of doing that. I wasn’t even thinking about a relationship, much less sex. I mean I was thinking about sex, just not thinking about having it with anypony. I was just so focused on my studies.”

“Well, for me it was less about sex, and more about work. I needed to get out of my house, and being an escort came with room and board. I made good money too.”

Hesitation on Twilight’s part. She was about to say something she wasn’t sure of. “Why… did you need to get out of your house so bad?”

‘Shit! Overshare! Quick, evade!’

I couldn’t find a subtle way to get away. I opted to be un-subtle. “Let’s change the subject. You said you were stressed? Did something happen?”

“Huh? Oh… I…” She blushed. “Sorry.”

“Don’t worry about it. I’d just rather talk about you than me.” I smiled a comforting smile. Calming tone. Relaxed posture. “So don’t fret.”

She got the hint. “Oh… I, uh… I don’t know.” She took a moment to compose herself before responding. “I’ve just been… not myself.”

“How so?” I took another sip.

“I’ve been… Irritable. Lethargic. Moody. On and off.”

“You want to talk about that?” I offered.

She shook her head. “No, I just… want some me-time.” She smiled again. It didn’t seem forced; she was genuinely in a good mood.

I didn’t want to risk upsetting her by prying. Besides, it was almost certainly due to her breakup, not much insight to be gained from a barrage of cleverly disguised questions. She’s probably too smart for that, anyways. “So, Twilight, did you have anything particular in mind?” I raised a suggestive eyebrow.

She smiled knowingly. Score. “Maaaaaaybe,” she teased. She was far from the nervous filly she was a few months ago. “I was hoping to… read some of your… books.” There was that cute blush. I’d been waiting for that. “I’ve been… curious. I don’t keep anything… like that… in my library.”

“And by ‘like that’ you mean smut, I assume.”

“I do.” She cleared her throat. “I’ve done a lot of reading over the years, but I never really delved into… erotica.” She twiddled her hooves nervously. Adorable. “I want to buy some for myself but…” Another shade of red on her cheeks. “I’m far too embarrassed to go through with it.”

“Well, I’ve got a small collection of raunchy books. Want to go rummage through them? We could have a little ‘reading date’.”

Her ears perked up at that. She was liking the idea already. “That sounds perfect!” she exclaimed. “We should get some snacks. Don’t worry. I won’t get any crumbs on the pages. I’m very careful about these things.”

“Good to know. Follow me, I’ll show you what I’ve got, literature-wise.” I led Twilight over to my book-chest. I have 50 or so erotic novels in many different flavors of sexy. Maid/master. Supernatural romance. Sexy historical fiction. I even have an erotic mystery. It’s more comedic than arousing, but I decided to keep it for the pure novelty.

“What’s this one? Royal rendezvous? Oh… it’s about Princess Celestia… I’m not touching that one,” she said, clearly grossed out.

“Oh, you know her personally, don’t you?”

She nodded, still scowling. “Yes. She personally taught me everything I know about magic.”

Holy shit, what? “Well… you’ve got connections.”

She giggled. “I suppose I do.”

“Not that you need any more convincing, but that book is about the princess seducing her personal protégé.”

She shuddered. “Okay, this book gets put in the veeeeeery bottom of the chest.”

I couldn’t help but laugh a little.

“What? She’s like my mom. It’s weird.” She laughed despite her discomfort.

“No no, I totally get you. I can’t read anything that takes place in a stable. It’s usually both incorrect and too close to home at the same time.” I looked through the books some more.

“What strikes your fancy?”

A pensive Twilight continued to shuffle through the books. “I dunno. Nothing’s really jumping out at me.”

“Well, what excites you? Being whisked away by a dashing prince or a burly jungle-hunk? Vampire ponies seducing helpless mortals?”

“That’s just it, Guilty. I don’t know what excites me.” She sighed heavily. “I haven’t been really exploring the sexual side of myself until recently.”

‘How do I address this? Do I just pick something vanilla?”

Most of my collection appealed to some kind of fetish, but I did have some really sappy love stories sprinkled with some heated chapters.

‘It would take too long to get to the sexy parts. Pick something with a mild kink that gets sexy within a few chapters.’

One came to mind. “How about… Love of the Enemy. It’s about a Pegasus soldier and a Unicorn guard during a battle between the three tribes.”

Twilight levitated the book over to herself. “What makes you think I’ll like this one?” she asked, examining the cover diligently.

“Well, it’s less about the content, and more about the pacing. I’d hate for you to get bored before anything… fun… happened. It’s also got decent writing compared to some smut, not that that’s a high bar.” I cleared my throat. “I will warn you it has a bit of a thing for chains. Nothing… rapey… but it does like its bondage.”

Twilight seemed satisfied. “I guess I’ll be experimenting with two things today,” she said almost excitedly. “What about you?”

“Me?”

“Of course. It’s more fun to read together! You pick something too.” Without prompting she climbed into the bed and got comfy.

I never really liked reading porn all that much, truth be told. I like pictures more. Trying to read a story has always felt… fuzzy. Out of focus. Like the sexy is there but I can’t see all the good bits. Still, there’s a few stories in the chest that I do like. It’s about an explorer who stumbles into a tribe of exiled female zebra warriors.

I like zebras and I like big mares, sue me.

I placed my book on the bed. “I’ll go get some chips. And some more wine. That’s an acceptable pairing, right?”

My hilarious joke about wine was lost on Twilight, who was already reading intently.

When I returned with the snacks, Twilight was already curled up comfortably with her book. Apparently she’s a fast reader, because she was already blushing. I made a point of making a little noise when I entered, so she noticed my presence; I didn’t want to startle her. Little details like that make the difference between a good escort and a great one.
“Having fun?”

She nodded. “It’s very… explicit.”

“That’s the point, isn’t it?” I asked, climbing onto the bed. I put the bowl of munchies between us. “Want me to top you off?”

“Mmmhmm,” she hummed. Her glass floated to me.

I filled her glass and my own, and the two of us began reading. Truthfully I was paying more attention to Twilight’s body language than the book. It didn’t take her long to get relaxed. A casual sip of wine every now and then, a chip every other page or so. She was entranced.

Couldn’t take her eyes of the book.

After a bit, Twilight seemed to hit the second sex scene. Her breathing got heavy, she shifted her legs a little, her tail twitched ever so faintly. She liked it. “This is really… something,” she said, swallowing.

“Something good? Or something bad?” I already knew the answer, but part of me wanted to hear her say it.

“Good… definitely good. It’s uh… getting to me.” She giggled nervously.

‘Do I torment her? Yes, I think I will.’

“Getting to you? How do you mean?” I smiled, knowingly.

“It um… you… you know what I mean. I’m… aroused,” she admitted.

I couldn’t stop myself from laughing. “You’re so clinical about it!”

She half-scowled at me. “Well, you’re the expert. What would you say?”

I pondered for a moment. “I’d probably said ‘turned on’. It strikes an appropriate balance between reserved and crude.”

She pouted falsely. “Well then… I’m ‘turned on’.” She smiled despite herself. “You continue to be quick on your hooves in a conversation, Guilty.”

“Thank you, I try. So, arousal aside, how’s the book?”

“It’s okay. There’s definitely not much depth to the characters. Just a stallion and a mare who really want to have sex.”

I nodded. “That’s erotica for you. It’s all about the sex.”

“It definitely seems that way. It seems like every event is in some way facilitating the eventual sexual situation. Like when the Unicorn’s robes get torn and expose her flanks. It’s just so that the Pegasus will get an erection and the Unicorn will notice. It’s kind of silly. Still it… does its job.” Her tail twitched. She was trying to keep it from rising.

Knowing how much Twilight was feeling it was doing wonders for my own arousal. I could feel my member pressing into the sheets.

“So,” Twilight began. “What about you? How’s your book?”

I absently flipped through the pages. “Oh, I’ve read it before. There are a few scenes in it that are pretty exciting.”

“What’s it about?” She scooted closer to look over my shoulder. In the process, she inadvertently pressed her side against mine. Breaking the touch barrier is a big step, so this was a very good sign.

I turned my attention to the book. “An Earth pony explorer stumbles into a wandering tribe of all-female zebra warriors. They are all, of course, attracted to him. He follows them around while simultaneously trying to find an ancient artifact. He also has sex with them a whole bunch.”

“One would assume.” She furrowed her brow. “How is a tribe all females? How do they reproduce?”

“They were apparently mares who were exiled from another tribe for… something. It’s hardly important compared to all the group sex,” I explained.

“Ah of course,” responded a sarcastic Twilight. “I wonder what that’s like.” She rolled onto her back.

“What, sex with multiple partners?” I asked.

“Yeah. Well, not just that, all kinds of sex. Sex while chained up. Sex outside. I’m just finding myself thinking about all the different kinds of sex there are. It’s a lot of very creative ways to orgasm.”

I thought for a moment before responding. “I’m not sure it’s all about the orgasm. There’s definitely more to sex than the physical pleasure.” I turned onto my back as well, staring into nothing with my guest. “There’s the intimacy, the excitement, the give and take of the whole thing. There can be an emotional aspect to sex just as much as a physical one.”

“You’re not wrong,” mused Twilight. “There’s a lot I’m just unsure about. I’m still pretty inexperienced. I’ve only had sex with one stallion, and it didn’t feel particularly… emotional.”

‘Interesting turn there at the end.’

“How do you mean? You weren’t really that into him?”

“No, I was. I… liked him a lot. But the sex was sort of… secondary to the relationship. It didn’t feel like it was any more intimate than anything else we would do together. Physically it was more gratifying, but it was no more emotionally fulfilling than, say, reading together. It was just another fun thing to do.”

“Hmm…”

“What?”

“Nothing. It’s just interesting. Everypony views sex differently. Everypony has kinks and hangups. Different levels of investment, different priorities. For some people it’s all about having as much sex as possible, for some it’s about having the best sex possible. For some, it’s about connecting with another pony.”

“I think two ponies can ‘connect’ better through conversation than sex. At least, that how it seems to me.”

I shrugged. “Like I said, it’s different for everypony. Some ponies aren’t good at expressing themselves verbally.”

‘Cough cough, Golden Harvest.’

“I guess that’s true.” Twilight sighed heavily. “Maybe I’m just bad at communicating physically.”

That sounded like she was concerned about something in particular. “What’s on your mind?”

She groaned. “Just… I don’t know. I feel like… Is it okay if I talk about my relationship?”

“Of course it is. This time is yours after all.”

“Right.” She took a deep purposeful breath. “So… we mostly broke up because we fought so much. But one fight we had a couple times was that he’d want to have sex when things were romantic. To me it always felt… like it was interrupting the romance. It was breaking away from a tender moment for the sake of physical pleasure.”

This was proving to be a pretty deep conversation. “So is it just that he wanted sex too much and it got tiresome? Or was it just his timing?”

“The latter, for sure. I was fine with the amount of sex. I like sex. It was just… he’d always ruin the mood. When I got mad about it, he said that he didn’t understand. That I didn’t understand.”

‘I didn’t peg Twilight for the type to separate emotion and sex, but it sounds like that’s what’s going on.’

“So, if I understand this, you don’t feel sex is particularly romantic?”

“Hmmm…” she pondered for a moment. “I guess not. I mean, you read about romantic and passionate love-making. But sex never really seems like that to me. It’s so… visceral. Animal, even.”

“You used that word when we first met. ‘Visceral.’ How do you mean that?”

“It’s all just… Fluids, meat, hormones, synapses. Everything about it is… pumping and thrusting and secreting.”

“So, you find it gross?”

“Well… isn’t it?” She rolled to face me. “The penis is basically a sponge that fills up with blood. It shoots out a sticky fluid composed of tiny organisms that swim around in the vagina and into the uterus. In the meantime the vulva are also swollen with blood, secreting a slippery fluid that makes it easier for the penis to slide in. On top of that you get covered in sweat, your heartbeat rises, you make a mess of whatever’s underneath you. And we do all of this because our bodies are telling us to make babies, which is an even longer list of bodily functions.”

“…wow…”

“Sorry…” Her ears went flat.

“No no, it’s interesting. Fascinating really.”

“What is?”

“The way you see sex.” I continued to stare into my ceiling. Past it, honestly. “You’re right, of course. That is what sex is. But for me, that’s what I really enjoy about sex.”

“How do you mean?”

“Just… the animality of it all. Indulging in your baser wants and desires. It lets you step out of who you are for a moment, and lets you be what you are.” I turned to meet her gaze.
“Does that make sense?”

She nodded. “Well, yes. And to some extent I agree. It’s nice just letting yourself be overwhelmed with the pleasure. But it’s still not something I see as being… romantic. Intimate.”

“You don’t really see it as going hoof-in-hoof with love, then.”

She paused. A long pause. I didn’t want to interrupt her. “No. I don’t. Sex doesn’t make me feel ‘loved’ it makes me feel ‘good’. It’s fun, but there’s nothing really intimate about it. Is it weird that I think that way?”

I purposefully chuckled. A well placed chuckle can really disarm somepony. “Weird is a weird concept. I think that your way of thinking is uncommon, especially for mares. But when ponies say weird they don’t just mean ‘uncommon’, they mean ‘uncommon and bad’.” Reassuring smile. “I don’t think it’s bad at all to think that way. I’ve known a few ponies like that. Whores mostly.” Playful smirk. “Ever consider a change in profession?”

She laughed despite herself. “Very funny.” She sat up and levitated her glass to her lips. “What about you?”

“What about me?”

“What does sex mean to Guilty?”

“Tough question,” I said flatly. It was a query with many answers. “I guess my ideas and feelings towards sex have evolved a lot over time.” I reached for my own glass, righting myself in the process. “When I was a teenager, prior to losing my virginity, sex always seemed like the… goal. Like it was what you needed to do to be an adult. After I did have sex for the first time, it was… anti-climactic. Not literally, I came like crazy. Just on a… mental level.”

“Really?” she asked as I took a moment to finish off my glass. Without prompting she began to fill it again. I was going to have to start pacing myself.

“Yeah. I was expecting it to sort of… change me somehow. Like my life would enter its next chapter. But nothing was different. I was still me except I knew what the inside of a mare felt like.”

“You sound like you were almost disappointed.”

“Hmmm… I wouldn’t use that word. It was more… it rearranged my priorities. Sex was no longer the most important thing on my mind. It was almost freeing.” I swirled my wine.

“After that, though, sex became… work. It was my profession. I was good at it. Am good at it. It take pride in it. Sex is sort of… part of my identity now.”

Twilight shot me a look that was… hard to read. One part pity, two parts fascination. Some disbelief mixed in there maybe. “I suppose I should’ve expected a complicated answer. Asking a sex-worker what sex means to them.”

“Yeah, it can be complicated. Especially where relationships are concerned.” I thought of Derpy. I reflexively smiled.

“You’re dating Derpy Hooves, right? What’s that like?”

“Dating Derpy? Or dating in general as an escort?”

“In general,” she answered.

“If we’re being honest, I don’t know. It’s the first… real relationship I’ve had. Things can get complicated, but Derpy doesn’t seem to mind my profession at all.”

“But I mean… sex with her. I-if you’re comfortable talking about it, of course.”

I was. My relationship with Derpy was no longer part of my job, it was part of my life. “It’s… hard to say.”

“Does it make you feel… loved? Does it make you feel, like… closer to her?”

I had to think about that. I’d been having sex with Derpy since I met her. Love only entered the equation very recently. Was the sex we were having now different from when we started? Was I still thinking about sex with Derpy in the same way?

“I think… I think it does. After we have sex sometimes we just… lay together. Hold each other. Kiss. We didn’t used to do that.”

Twilight didn’t seem to like that answer. She sighed heavily and flopped onto the bed, her wine continued to swirl aimlessly above her head. “I wish I understood why.”

‘Quick, cheer her up.’

“Well, maybe you will. Maybe you just need to meet the right stallion. Or mare. No judgement. It might not be that you don’t connect sex and romance, it might just be that you didn’t connect sex and romance to him.”

“Maybe…” She arched her back in a long vigorous stretch. “Why does talking to you come so easily?”

“Well, I do my best to listen and not judge. Comes with the territory.”

“I don’t know; it feels like it’s more than that.”

“Well, there’s always the fact that I’m not part of your life outside these walls. I’m more or less a stranger. The things you say here won’t affect your social or professional life.”

“Well, I still think of you as a friend outside of here, Guilty.”

That was awfully sweet of her.

“And I do get what you’re saying. But even beyond that, there’s just something about the way you talk, the way you think.”

My brow furrowed. “The way I think?”

“Yeah. We obviously have different experiences, different memories, different opinions. We’re different ponies. But it feels like our brains are sort of… built the same. We think different things, but the mental processes you use to reach the conclusions you reach feel like they’re… similar to mine.”

I wasn’t quite sure what she was getting at. Maybe the act I put on with her just happened to hit the nail on the head. Then again, maybe she’s on to something. She seems like a pony who “gets it.”

I decided to humor her a bit. “I think I… vaguely understand what you mean. We’re both… calculating, scrutinizing.”

“Exactly,” she responded. “It’s nice to talk to you. It’s sort of like bouncing ideas around in my own head. Do you ever do that? Talk to yourself in your head?”

‘Say nothing.’

“No comment.”

‘Masterful. Bravo.’

“I do it a lot,” she went on. “I practice conversations. Run through scenarios in my head. Think of responses ahead of time to questions that no one has asked.”

“Is that like a social anxiety thing? Want to be prepared?”

“Maybe a little.” She sat up and looked back at me. “Do you mind this? It’s becoming a sort of… personal conversation. Is this okay?”

Comforting smile. “Twilight, I’ve had far more personal conversations than this about clients. You wouldn’t believe the things people confess to me.”

“Okay. Good. I wouldn’t want to make you… uncomfortable again.”

I sighed internally. “Don’t worry about it. I blame myself for that more than anything. As a rule I try not to bring up certain parts of my life.”

“I’m sorry. I should’ve known better.” Her head sank.

“Nonsense, it’s just natural curiosity.” There was a pregnant pause. “That’s been… happening more lately, though.”

“What has?”

“Me slipping up like that.”

“Did something hap—?” She cut herself off, a mortified expression on her face. “Sorry. Forget I asked. I’m prying again.”

“It’s okay. I guess…”

‘Okay maybe Twilight knew what she was talking about. The idea of talking to her about this didn’t fill me with the usual instant sense of dread. I wanted her input.’

“I guess it’s because I started having feelings for Derpy. She’s the first pony I’ve sort of opened up to in a while. I’ve told her things I… haven’t told anypony in years.”

“Maybe it’s just because you let yourself think about those things again. You told her about whatever you told her about, and that put them back into your head. If they’re in your head all the time they’re bound to slip out eventually,” she theorized.

“Yeah. I was thinking somewhat along those lines. I’m opening up to her, and as a side effect I’m opening up in general.”

She just nodded.

“Okay… I think I get what you mean,” I relented. “We do have very similar ways of thinking about things.”

“Told you,” she said triumphantly.

I hadn’t really realized it happening, but over the course of the conversation I’d slipped out of my act. I wasn’t being an escort at the moment, I was just… talking to Twilight. I wanted to kick myself for it, but part of me felt that this was exactly what Twilight needed. Just some honest conversation.

There was a moment of silence. Neither of us really had anything to say, it seemed.

I said something anyways. “So, what now?”

“I’m not sure.” She rolled back onto her stomach and I followed suit. “I’d like to get back out of my head, frankly. I need a distraction.”

“Back to reading then?” I offered.

She blushed. “The book gets me so worked up, though.”

“Ah so we’ve moved from ‘turned on’ to ‘worked up’. You’re mastering the art of implication already.”

“Well, I guess I have a good teacher,” she teased.

“So, if you find the book is working you up to much, I could always… help… with that.” No lurid smile, no cheeky tone, just on honest offer. “Relieve some of the pressure that builds up. Or is that too quick of a change in gears from our conversation just now?”

“Honestly… I could really use that.” She started twiddling her hooves again. “I wanted to ask earlier, but I was too shy.”

‘Score!’

“Could you… um… use your tongue?”

‘Double score!’

“Twilight, it would be my pleasure.” Now was the time for some seduction. Smoldering Gaze. Sly smirk. Syllables laden with honey.

“Good,” she said through increasingly heavy breaths. Her excitement was building. That rare excitement that comes from being intimate with someone for the first time. The shuddering in your chest. The inability to stop smiling. The tingling all over.

I’m sort of numb to that now. I’ve been with so many ponies that it’s become background noise. Only every now and again does that special, first-time excitement rear its head.

I sort of miss it.

“Give me two shakes.”

Unless I was mistaken, I was going to be Twilight’s second. I could see on her face just how excited she was. She was literally trembling with anticipation. I repositioned, sliding across the bed behind her. With one last big smile, she turned back to her book, finding her place again.

Her tail flicked nervously, unsure of just how much to expose. Through the twitching curtain of dark blue, I could see her lips glistening. She was soaked. With gentle hooves, I guided her lower half. She was a bit clumsy, not sure precisely where I was leading her, but in moments she was on her back, hind legs high in the air, a large “V” that met at her wet entrance.

Her juices were practically running down her coat. More than wet, she was drenched. I held her legs apart as I moved my muzzle closer to her entrance. She quivered as I approached, tickled by my breath.

I began to tease her, placing small kisses and pecks up her legs. She shook with pleasure and anticipation. I waited for her to get impatient. Waited for her to need it. The whole while she stared at her book as it floated above her head.

She began to get breathy, started to squirm. She was aching for it. She gyrated, desperate for relief. I waited until she was at her limit before placing a long slow lick along her entrance.

“Aaaaaah!” she screamed. “Ohmigosh!”

This was heaven. Muzzle-deep in a lovely mare. Feeling her every spasm and twitch. Indulging in her taste. Listening to her pleasured whimpers.

“Mmmm… that’s… that’s so goooood.” The words practically oozed out of her mouth. I saw an opportunity to tease her more.

I lifted my mouth from her entrance, strands of fluid connecting us. “Me, or the book?”

“Y-you! Don’t stop!” she answered. “I’m so close already; don’t stop.” I dove back in, moving my tongue with renewed vigor. I could feel her whole body begin to tense. “Guilty… Guilty I’m going to… I’m going to…”

She thrust her hips into my muzzle, desperate for more contact, more pleasure. I matched her pressure with my own, placing firm swift licks across her clit. It didn’t even take a minute to bring her over the edge. Her legs trembled as she yelped in pleasure. After a few moments her body collapsed, sweaty, tired, bathing in afterglow.

“How was that?” I asked with a smirk.

“Good. V-very good.” Even through her orgasm her gaze stayed fixed to the book. “I was in the perfect spot for it too.” Her hooves twiddled in front of her. “Can we… go again?”

“More tongue?” I inquired. “Or something else?”

“More like this. Exactly like this,” she insisted.

“No argument here. Thirty seconds?”

“Hurry back, please.” She was sort of absorbed in the book and the pleasure. I can see how somepony might be off-put by her behavior, feel neglected, perhaps. Didn’t bother me.

I quickly slid off the bed, downed a potion, and slid right back into position. I could feel things escalating. Better to break up the action right after an orgasm, rather than right before one. Better safe than sorry.

“Ready for more?”

“Mmhmm… just take it slow for now,” she requested. “Nothing really steamy is happening.”

I spent the next couple chapters gently pleasuring her nethers. Slow gentle licks and kisses. The occasional dragging of my hoof across her coat. Hearing her faint pants and moans alone was enough to get me appropriately aroused (to borrow Twilight’s term). If I didn’t have any self-control, I might have gotten off from the sheets rubbing against my shaft.

There was something very refreshing about the lack of pretense with Twilight. For all her awkwardness, there was no real illusion that this is something more than just sex. She was paying me to give head, and that was the end of it. I wasn’t putting energy into an act. If anything, I was behaving more like myself than with most other clients.
It might sound sort of cold, or sad to think of sex like that, but I do. Sex is work. Most of the time, I have to pretend: It’s the best sex I’ve ever had. The mare is amazing. I’m 100% enthralled.

In truth, for most of my sessions I’m bored. I put everything into the act, and into the sex. I’m dedicated to my work, but it is work. And Twilight didn’t seem to mind that that was all it was to me. It made my job much easier.

Please don’t misunderstand, I love my job.

But it is a job.

That said, I was currently snout deep in an adorable librarian who was actually pleasant to talk to, so this didn’t feel too much like work.

“Okay, faster now,” she insisted. I think she’d be a good dom. She’s good at asking for what she wants. A little practice and she’d be good at demanding it.

I increased my pace, diving into her depths with practiced licks and swirls.

“Oh yes… yesyesyes.” I lamented that I could not see her face at this moment. “Guilty, you’re soooooooo good at this.”

“Mmhmm,” I hummed.

She gasped. “Oh… I liked that. Hum more. That feels good.”

“Mmmmmmmmmm,” I obliged. Mixing some low hums into my routine.

“Oh, Guilty, that’s so good.” Her hind legs began to squeeze the sides of my head. It was a comfortable pressure that kept my mouth firmly against her entrance. “You’re going to make me cum again!” I doubled down on speed, flicking wildly across her clit. The pressure on my head grew tighter as she got closer and closer to climax. “G-guilty!”

I felt the familiar sensation of a mare’s orgasm against my lips. I relished it. Twilight collapsed in sweaty pile of limbs. Her book (well, my book) lay tossed at her side. “Th-that was a really big one.”

“I’m glad. Too distracted to keep reading?” I teased.

She nodded. “I couldn’t focus on the words. Oh my gosh, I’m still throbbing down there.” A giant grin was plastered on her face as her chest rose and fell with her gasping breaths. “That was the best orgasm I’ve ever had.”

“I try.”

“Practice makes perfect… I guess.”

“You need a break?”

“Yeah. Let me catch my breath.” She wiped the sweat from her brow. “Between the wine and the book, I don’t think I’ve ever been more… turned on.”

“Don’t forget the oral sex.”

“That too.” She reached over and took a large gulp from her glass.

I stifled a worried look. “If you need to hydrate, wine is not really your best choice. Want some water?”

Realization registered on her face. “Of course. I wasn’t even thinking. Yes, water would be ideal.”

I nodded, and left to fetch a glass. My insistent erection bobbed beneath me the whole way.

‘I’m loving this. This is a good session.’

There was a noticeable spring in my step as I returned. Twilight had begun reading again, legs spread, pussy exposed for the world to see.

Well, just me to see, really.

“You really like reading, huh?” I placed the water next to the wine glass. “Makes sense you own a library.”

“I don’t actually own it. Ponyville does.” She sat up, floating the water to her lips for a quick sip. “But yes, I do like reading. I always have. It’s calming.”

I smirked. “Even when it’s ‘arousing’?”

“Weirdly, yes. Those two orgasms were quite relaxing. Even if the second one was mind-blowingly huge.” Her eyes were still flitting across the pages as they hovered in front of her face.

“You can talk to me normally even when you’re reading?”

She nodded. “There’s a spell that helps with it. I also use it to read two things at once. Sort of a multitasking spell. Mind-magic. Really tricky stuff.”

“Freaky,” was all I had to offer. “So, are you enjoying this? Reading and cunnilingus.”

“Very much so. I’d like to take it further, if that’s alright.” She closed the book and looked me in the eyes. Her face was very sincere. “Can we have sex sex? Is that okay?”

I nodded. “Of course it is. I’m surprised you asked so directly.”

“I feel too good to be shy right now. This is amazing. You’re really really good at this.”

“You mean… giving head?” I asked.

Her brow furrowed slightly as she looked around the room. “I mean yes, but it’s so much more than that, isn’t it? It’s not just the physical acts you perform. The way you make a pony feel comfortable, the atmosphere you create. I’m sure a lot of your word choice and tone is carefully considered. The book you chose for me, the warm tones you use in your decorating.

“Everything you do takes so much planning and forethought. You really make a pony feel…” She looked for a word she couldn’t find.

“At ease?” I offered.

“Safe,” she said with some finality. “You really make this feel like a safe space to be… sexual.”

I smiled. “That’s true. Especially since I’m a stallion, and my clients are mares. A pony can’t feel pressured or persuaded while they’re here. I try to match tone, body language, attitude. Never as a form of deception, mind you. It’s just salesponyship.”

At this point, I was sort of peeling back the veneer, but I thought Twilight might appreciate it.

“Especially difficult is when it comes to sex. It’s really easy to scare someone off if I’m too aggressive. Feeling out what a pony is and isn’t into takes a lot of mental acuity. Ponies tend not to SAY what they want, but they still expect me to know.”

Twilight blinked. “Wow.”

‘Shit, was that too frank?’

I doubled back. “Sorry. Too much?”

“No… no it’s just… impressive. It’s a remarkable attention to detail. You don’t even have the benefit of a concentration spell.”

“But I do have the benefit of years of practice,” I pointed out.

“True enough. Still. You put an admirable amount of effort into this.” She shuffled her hooves a bit. “It makes me feel a little bit like I’m not paying you enough.”

I thought she might say that. “Don’t worry about that. For what it’s worth, you’re a very easy client. There’s not a whole lot of pretense with you. Not to mention, you’re actually very pleasant to talk to. I’m enjoying this.”

A face of both doubt and acceptance. “I… good.”

“Now, there was mention of sex sex?”

She giggled adorably. “Right. I did say that. Would that be okay?”

“Twilight, I’ve had an erection since we started reading. That would be more than okay.”

“Great. So… how do you want to…”

“How do you want to?”

“Oh, um… let me think.” Her hooves twiddled again. “Could I try being on top? I haven’t done that before.”

Comforting tone. “That sounds just fine.” I laid back, my member pointing skyward. “This okay?”

“Yeah, like that. Let me see.” Twilight took a moment to work out the mechanics of climbing on top of me. She was still quite inexperienced with the physical techniques of sex. She didn’t have the muscle memory of some of my more experienced clients. With no small amount of awkwardness she managed to get herself into a reverse cowgirl position, my stallionhood pressed against the length of her entrance. “Is this okay?”

Intentionally audible chuckle. “That’s for you to decide. Are you comfortable?”

She nodded.

“Then let me just…” I adjusted myself, placing the head of my shaft towards her entrance. “... okay, now just ease down on top of me.”

I waited in agony as Twilight slowly lowered her hips onto mine. Hot wet pleasure wrapped around me. She gasped audibly as she reached the hilt of me. “You’re really hard.”

“I know. You’re really wet.”

“I know…” She was breathing so hard I thought she might pass out. “Guilty, this is really hot.”

I’m not sure what aspect of the situation was doing it for her, but I was glad she was enjoying herself. “Yeah… you feel really good.” It wasn’t a lie.

Without a response she started moving. Her hips rose and fell along the length of me. Her tail tickled at my chest as she gyrated. It felt kind of nice.

Through my pleasure, I found the time to analyze her technique. “You shouldn’t hunch. You’ll get sore…” Normally, I wouldn’t criticize a client, but Twilight seemed like she’d appreciate honest feedback.

She stopped bouncing for a moment to straighten out her spine. “Like this?”

“Yes. Please start moving again, it feels so good.”

With a nod she resumed. She seemed to enjoying being on top quite a bit. Her yelps and moans raised in volume as the minutes passed. I could feel her climax approaching. “Guilty, I’m—“ Her orgasm interrupted her sentence. Her insides gripped my shaft tightly as she literally shook with pleasure. She muffled her screams with her hooves.

Once her pleasure subsided, she clumsily climbed off of me before collapsing into a heap of sweaty mare. “I like being on top,” she announced excitedly. She threw her hooves up with equal parts glee and exhaustion. “That was exactly what I needed.”

“Good.” Helping a mare discover herself sexually is always a good thing.

“D-did you finish too?”

“No, but that’s fine.”

“No, I want you to. I want you to…” She rolled away from me. “… cover my back with it. I-if you can.”

“With how good that felt, it won’t take me long,” I assured her. I sidled up behind her and began to stroke myself. Twilight pushed into me, her coat rubbing against my throbbing length.

“It’s so warm,” she commented. “I like how it feels.”

“Me too.” I nuzzled her neck. “Almost there.”

“Yeah?”

“Yeah!” I grunted as I felt pleasure overtake me. Streams of hot white mess shot along her back painting her coat with messy pleasure. It felt amazing. I came quite a bit.

“Hooo… that was good.” I felt goosebumps creep onto her skin as she relished the warm sticky feeling. Was it good for you?”

She nodded. “Perfect. Perfect perfect perfect,” she assured me. “I need a moment.”

“Take all the moments you need. I’m hourly.”

She laughed at that. “So witty.”

“Again. Practice.”

“Good at sex, too,” she said between labored breaths.

“I won’t deny that.”

“Will you be good to go again in a bit?”

I smiled. “I’ve got a couple more in me.”

“Great… I want more…”

“Thirsty, aren’t we?”

“I could use some more water, yeah.”

“I meant… never mind. I’ll get you that water.”

“Thank you, Guilty,” she said tiredly.

This was going well. Twilight was bathing in ecstasy, I’d blown a huge load myself, all was right with Guilty. That said, I was slightly worried about overdoing it. Twilight was still fairly inexperienced, after all. I’d hate for her to try a position she couldn’t handle.

When I returned she was lying on her back, legs spread, lips soaking, chest heaving. Add a cigarette and she’d be the poster girl for post-coital bliss.

“How are we feeling?” I asked. “Good, I hope.”

“I would classify this as euphoria. This… post-orgasm haze of endorphins and adrenaline really is something special.”

“Couldn’t agree more.” I placed her water on the bedside table.

“You do this for a living. Your life is amazing.”

“It definitely has its perks. Like cumming on sexy librarians’ backs.”

“Whu… I’m not sexy!”

“I beg to differ. Your body thoroughly excites me.”

“That’s…”

“You felt how hard I was. Can’t deny the erection.”

“… Okay, fine.”

“Why is it that ponies always think they aren’t sexy? Nine out of ten of my clients insist they aren’t attractive.”

“We all compare ourselves to models and royalty. I think it’s probably harder for mares. Celestia and Luna are literal goddesses; they represent genuinely impossible standards.”

“That’s a well-reasoned and concise answer.”

”I wrote a paper on it once. Princess Celestia was not the biggest fan.”

I failed to stop myself from giggling. “That’s hilarious.”

“In hindsight, yes. At the time I was mortified. I never thought she’d take it personally.” She sounded a little too serious for my comfort.

“You okay? Conversation kind of took a turn.”

She sighed. “I dunno. It just brought up some embarrassing memories.”

“Sorry to kill the mood.”

“Oh no, I’m still horny. A little awkwardness isn’t going to turn me off at this point.”

“Well that’s good. You ready to keep going?”

She smiled. “Yes, and I uh… have a request.”

“I’m all ears.”

“Can I… use my mouth on you?”

“You will hear no complaints from me,” I teased.

“Here.” She patted the bed next to her. “Lie on your back.”

I obliged, sliding into position beside her. She eagerly lowered her head down, gently nuzzling my member.

“I love this smell. This stallion smell,” she said, almost entranced. “I like it more than I like it.”

I cocked my head. “How do you mean?”

“Objectively, it’s a musty, sweaty, sour sort of smell.” She gave a quick peck to the end of my erect self. “But, for some reason, I can’t get enough.” She gave a slow wet lick along my shaft. Her technique was non-existent, but the attention was no less pleasurable. “The smell of stallion is just…” she cut herself off, inhaling deeply “… addictive.” The word practically oozed out of her. She wrapped her lips around my tip, relishing the flavor of me.

I moaned audibly. “That’s nice.” This earned a giggle from Twilight, as she began to take more of me into her mouth. As she started bobbing up and down on my length, I saw her hoof reach down to her own nethers.

With a pop, she pulled off of me and took a breath. “I like that I can fit the whole thing in my mouth. I couldn’t do that with my ex.” She paused awkwardly, realization dawning on her face. “Was that mean? Was that an insult?”

I was feeling too good to be insulted. “No, I like that you like it. I know I’m smaller than most. I don’t take it personally.”

‘Usually.’

“O-okay.” So nervous, this one.

She returned to the act of fellating and masturbating at the same time. After a few minutes she swung her hips around to my face, placing us in an extremely pleasurable sixty-nine. Twilight was positively enamored with my package, practically feasting on me. She pushed her lips against my tongue with what could only be described as gusto. I let my hooves trail delicately across her sides as I kissed and licked her.

This was perfect.

Sex with Twilight lasted a good while. We tried out 2 more positions after that. She had all the vitality of a teenager. At the end of it all, she asked to cuddle. We spooned on the bed for a time, amidst the stains and the musk of our passion. It was a lovely few minutes, inhaling the scent of her mane, feeling her coat against mine.

“Did you have fun?” I asked.

“Yes… yes I did,” she replied.

‘There was a hint of worry in that. Double check.’

“You sure? You seem a little out of it.”

“I… I feel bad.”

“What for?”

She rolled away from my embrace, sitting upright to face me. “I feel bad because I just had a lot of fun sex… but I really need to say something.”

The hairs on the back of my neck shot straight up, and my posture followed suit. I sat up to meet her gaze. I could feel something coming. I was not going to like this.

“I want… no, I need… to talk to you about Applejack.”

‘… fuck…’

She continued, “I was… I was going to wait… until maybe we cleaned up first but… but it was eating at me… I’m sorry.”

“No no, it’s okay…”

‘It is far from fucking okay.’

My head was spinning. It was such a violent change of gears. Twilight looked uncomfortable, herself, but I was panicking about as much as I ever have. Still, I kept it together… mostly.

I was almost shaking. My mouth refused to cooperate. “I-i-i… S-so… what did y-you want to s-say?”

The pinnacle of elegance.

“I’m… I’m really sorry. I just… I promised myself I would do this, and the waiting was killing me.”

“I… understand.” If I wasn’t already sweating from the raucous love-making, I would’ve started right then.

“The situation between you two has gotten… out of hoof. Between her getting in an actual fight with Derpy… your friend apparently trying to proposition her… the fact that neither of you is acknowledging the other’s presence…”

‘Sounds fine to me!’

“Both of you…” she sighed. “You’re not exactly acting like foals… but you’re… you’re…” She couldn’t find the words. Twilight couldn’t find the words.

“It pains me to see two… good ponies… one of whom is one of my best friends… bickering like this. No, not even bickering… fighting. You two are practically at war. I hate that Rarity and I both have to stay quiet whenever she badmouths you. I hate seeing ponies whisper behind both of your backs.”

I swallowed. This was an all too familiar feeling. Being lectured. I was in Hell.

“And not just you two. Ponies talk about Derpy, too. I know that gets to her… even if she doesn’t show it.”

“I—”

“Let me get this all out first... Where was I?”

“Derpy…”

“Right. Look.” She took a shaky breath. This wasn’t easy for her. “Your feud affects more ponies than just you. In a small town like this… things grow. I’m from a big city too, I was born in Canterlot. I know that in a city if you get into a fight with someone on the street, you walk away in a huff and that’s the end of it. You never see that pony again. The ponies walking on the street are just background noise.

“But you live in Ponyville now. Ponyville isn’t Canterlot, it isn’t Manehattan. That fight hangs in the air until the air is cleared. And the air needs to be cleared, Guilty. You two need to patch things up. If this keeps going… gosh… I hate to think how this could start to affect Dinky and Applebloom.”

“…”

She coughed awkwardly. “Applebloom is Applejack’s little sister… if you didn’t know.”

“I did not...”

“Well… that’s what I promised myself I would say.”

I couldn’t respond. I felt like a child.

When you’re a kid and an adult is yelling at you… it sort of shuts your world down. The idea that you’ve fucked up overwhelms you. You can’t see past the moment. There’s this blinding feeling that you’re bad. You’re a bad pony, and you’ll never be good. That you’ll never be forgiven. That you shouldn’t be forgiven. That maybe you shouldn’t exist.

“I’m… I’m sorry.” Twilight spoke up. How long had I been silent. “Believe it or not, I’m not just trying to… guilt you. I know you’re not the only one in the wrong. You and Applejack have both really attacked each other. I’m… I’m going to have the same talk with her that I did with you.”

Words wouldn’t come. I could see Twilight tensing up more and more. I wanted to talk. To move forward, get past this terrible moment. Something about the moment took me right back to my childhood, when my father would berate me. Twilight was nothing like my father, but I was just as frozen and scared as if she was.

“Look, I… I didn’t mean to…” She was starting to panic. “I’m… I’m sorry…” I could hear her beginning to tear up. “W-was I too mean? I… I wasn’t trying to upset you, I just…”

I couldn’t move. I could barely breathe. I’m fairly certain I had a panic attack.

‘Deep breaths, Guilty.’

“P-please don’t hate me!” She started to sniff.

‘Move, Guilty.’

“I… I should go. I’ll go.”

“Wait,” I managed to get out. “You’re… it’s fine.”

“I… I’m sorry. I knew it was going to be hard to bring up but I had to.”

“I… It was just… we changed gears too quickly. I have… whiplash.”

“I… Okay, yeah… I can see that. I’m sorry.”

“You don’t need to apologize.”

“… okay…”

“Give me… give me 30 seconds.”

“I… uh… sure…?” Twilight

I took a deep breath. A very deep breath. The kind of breath that stretches your insides to their limit. I exhaled, slowly, purposefully, calmly. I needed to make my body calm down. Needed to ease myself out of panic mode.

“Twilght…” I was in control of myself again. Not tripping over my words, not shaking. “I… get that you needed to say this. I really do. I find it sort of odd that you decided to take advantage of my services first, but let’s just chalk that up to your apparent disconnect between sex and emotion, and perhaps a bit of social awkwardness.” I regret my phrasing in hindsight. I was a bit blunter than I needed to be. She already felt bad.

“I also find it… extremely optimistic of you to think that Applejack and I can or would patch things up.”

“I… I know. But… but I have to believe that you can. That you will.”

I didn’t know how to respond to her raw sincerity.

“Friendship is my… calling. I don’t know if you two can be friends… I’m not asking that of you. But I know you can at least be… not-enemies. You don’t have to hate each other like this.”

“I don’t…”

‘Nice try. You fuckin’ hate that mare. Don’t even lie.’

I sighed, too tired to even fool myself into believing that. “I do hate her. She’s been a stone bitch to me from the moment we met. Before, even. She decided how she felt about me the moment she heard I was an escort. All I did was follow suit.”

Her face fell, nearly imperceptibly. “I think we both know that’s just an elaborate way of saying ‘she started it.’” Fuck. She was dead-on. “I know… hating her is easier than trying to reconcile. Any relationship takes work.”

I was just not in a headspace for this. But then again, would I ever be?

I dragged a hoof across my face. “So… what’s your plan, then? Sit down, just the two of us. Yell until we make nice?”

“Not just you two. I’d be there. I think Derpy should be too. Rarity said she’d come too, since she cares about you and Applejack.”

“I… I’ll consider it.”

She shook her head. “Not good enough.”

“I’m sorry?”

“Promise me. Promise me you’ll at least sit down with her. I know it’s not really my place to insist, but… promise me. This matters to me. To a lot of ponies.” She was resolute.

‘Just give in, Guilty. She’s too earnest for your cynical ass.’

I did my best to suppress a groan. “Fine. I promise I will at least sit down with her. Beyond that… I will make an effort.”

“That’s… thank you.” She breathed a sigh of relief.

“Let me say something, though.”

Her turn to swallow. “Oh?”

“I don’t normally say this to a client. But I’m kind of upset. It feels like you used my profession as a way to corner me. Especially, since you actually went through with the sex before doing so.”

“I… I get that. I really did want to have… have sex with you. I didn’t just come to say this. I just… I had to get it out there. I promise I wasn’t trying to corner you.”

“I know. You’re not so devious. Still…” I smiled as best I could. “… maybe wait until we’re showered off before you drop a serious-bomb on me. Not just me, but… anypony you have sex with.”

Twilight nodded. “I… I already regret my timing. I clearly have… different ideas about sex than most ponies.”

“And again, that’s fine. You just have to be aware of what other ponies might expect.” I was already back to being an escort, giving her erotic advice.

‘Time to move past that terrible terrible awkwardness. Push forward.’

I forced myself to be professional. “Well… all that being said. We both still smell like sweat and sex-juice. Let’s go take a shower.”

“That sounds…” she smiled tiredly. “cleansing.”

“Indeed so.”

Troubled as I was by what had happened, I was still a professional. Twilight and I had a nice hot shower, continued to make pleasant conversation, had some more tea. She ended up borrowing the book she’d started, promising to return it soon. She paid for the sessions, and we said our goodbyes.

After she left, I found myself staring at the door. Couldn’t move or form a thought. Just stunned. Took me a few minutes to start cleaning up, getting everything in order. Still, I was sort of on autopilot. My brain was off.

I shook myself back to normality. I cleaned up, poured myself a drink, settled in for the night. I ended up re-reading my book about sexy Zebra mares. Yet through all this, I was still dwelling on what had just happened. I’d promised to sit down with Applejack.

I’m still kind of in denial of the whole thing. It doesn’t feel real.

Derpy is visiting for lunch tomorrow, so… I’ll bring it up to her then. That will probably knock me into reality.

Ultimately, It was a real whirlwind of a Wednesday.

I’m going to sleep now.

Author's Note

WOW it's been too long.

Thanks everyone for reading. I will not let this fic die. I'm quite happy with how this chapter turned out, considering it took YEARS to write.

Please comment and all that. Your praise sustains me.

Disco

Impossible Ponies

A date has been set for the meeting with Applejack. I’ve got a week to mentally and emotionally prepare myself.

I am… not looking forward to this.

I told Derpy about the coming social apocalypse. She insisted that she be there too, which I'm thankful for, honestly. I’m still feeling sort of numb to this coming meeting. It doesn’t feel real yet. I can’t even conceptualize a version of this that doesn’t turn into a shouting match or actual slugfest. Derpy also said she’s going to ask the girls if any of them would want to be there which, again, I'm thankful for.

Speaking of the girls, they seem to be doing well. Lyra and Bon Bon are as close as ever. Lyra got a gig in Canterlot so she’s been practicing a lot. Bon Bon’s confectionary got a new sign out front. This is what qualifies as exciting in a small town, it seems.

Even Golden Harvest and Lily seem to be doing okay. They don’t fight as much in public. Ms. Harvest seems less hostile towards me. Lily is still a little awkward around me, but she’s been getting better. She’s still nervous around Derpy sometimes. Keeping secrets is hard for some ponies.

I want to put this out of my head. I’m still processing this whole thing.

But as much as I am nervous about the meeting.... I CANNOT STOP THINKING ABOUT THE BALLS CRAZY SESSION FROM THE NIGHT BEFORE LAST!

The story starts just before midnight.

A new client wrote me. Asked for a late night rendezvous. The letter was very formal. The writing was very elegant. The stationary looked quite fancy.

Her knock was not the knock of a first-timer. I was almost surprised. Loud and confident.

The mare was stunning. Truly stunning. I almost forgot to greet her. She was big. Not chubby, not muscled, not tall and lanky. Just large. A head taller than me. A giant of a mare.

Despite her size she was elegant; she moved with preternatural grace. “Guilty, I presume.” Her voice carried a sort of weight. An authority.

“Yes,” was the best I could muster. She’d thrown me off my game. I gave my head a quick shake.

‘Back in the act, Guilty. What’s the matter with you.’

Coy smile. Raised eyebrow. Seductive voice. “And you must be my mysterious new client.”

She smiled. It was not the sort of smile I was used to receiving. A proud smile. Like she was telling me “good job”. She was odd. No embarrassment from a first-timer. No excitement from a regular client. No stress of someone who’d come to talk about troubles. I couldn’t get a bead on her.

Her horn began to glow as her coat levitated off of her frame.

Her body was gorgeous. Curves in all the right places. A long wavy mane. A dark blue coat that practically shimmered. Her cutiemark was actually quite plain. A single candle.

“Do come in. You must be freezing.” I was determined not to get knocked out of my groove again. I knew my role, even if hers was a mystery.. I’d be the best damn escort I could.

“Thank you, Guilty. May I call you Guilty?”

“Of course you may. On the condition that you tell me what I can call you.” Gentle body language. Suggestive smile. Smooth tone.

I led her to the living room table. Guided her to a seat. “Would you like some tea?”

She shook her head. “No need. I’m quite awake. Feel free to make some for yourself, if you require.”

“Oh I think I’ll be alright. The sight of you perked me right up.” Obvious flattery seemed appropriate. She wasn’t shy. She would appreciate the flirtation.

“Quick on the draw, aren’t we. Hopefully not so quick when it matters,” she fired back with a clever flirt of her own, followed by a measured smirk. I liked this mare already. “Now then. Let us begin.”

“Indeed.” I sat across from her, trying to size her up. What was she after?

“Midnight,” she interjected.

I looked at me clock. “So it is.” What was she getting at?

“That is what you may call me. That was your condition was it not?”

Ah. Of course. Keep it together, Guilty. “Seems appropriate.” I smiled. “So how did you hear about me? What brought you here?”

She looked around the room. “I’m not quite sure. I’d heard about you from a friend of the family. Something about you just… called to me. The idea of you was intriguing.” I wasn’t quite sure what she meant by that.

“How do you mean?”

“A pony who picked up their whole life and settled down in an unfamiliar town away from anypony he ever knew. What causes a pony to uproot themselves like that?” She looked at me. She was sizing me up just as much as I was her. “You keep a lovely home. Very warm. Very…”

“Safe?” I offered.

“Yes… exactly so.”

“I’m glad you think so. Now, Midnight, if I may ask…” I waited for a response. An affirmative. Kept her in the conversation.

She nodded. Perfect.

“What can I do for you?”

“I’m not so sure I have an answer. I could have you pleasure me. I could unload my stress and worry onto you. Complain about the hardships of my duties or the problems with my social life. I could even have you wait on me. Serve me tea, perhaps a cocktail. Worship at my hooves.”

I nodded. “All perfectly acceptable options.”

“Take your pick,” she said devilishly.

“I’m sorry?”

“I want you to choose what we do. Dealer’s choice, as it were.”

I’d… never had to deal with this dilemma before. Sometimes mares do something like this; ask me what I want to do. But when they ask they’re not really asking. They’re telling me that they want me to be in control. They’re asking to be servants.

This mare, however. She wasn’t. She wasn’t looking for some master-servant play. She was genuinely asking what I wanted to do. She was passing me the reins, curious as to where I’d steer us. I looked to her body language. Any tells? Any insights?

Nothing. Unreadable. A mare practiced in poker-face.

‘Perhaps honesty is the best policy.’

“There are a number of things I’d like to do. I’d absolutely love to pleasure you. You’re impossibly beautiful. You’re quite large, if you don’t mind me saying, and I rather like large mares. We could have all sorts of fun in the bedroom.”

Her expression maintained its confidence, but a blush did start to appear.

“I’d also love to hear more about you. You honestly intrigue me. I can’t figure out quite what you’re after. I feel like there’s some sort of ulterior motive for your visit but I don’t think it’s malicious.”

Surprise on her face for the first time. Impressed maybe? It wasn’t much more than a bluff but it seems to have worked.

“Or we could just enjoy the anonymous company. I barely know you. You barely know me. We could sit and sip cocoa. Read. Just be alone together for a night.”

“So… which will it be?” She’d regained her composure. She wouldn’t let me forget that I had to choose. I’d been hoping to redirect her.

I found myself… excited. I liked this. This was me putting my special talent to the test. Trying to unravel this mare. “Then let’s talk. Let’s get to know each other.”

She clapped her hooves together, a genuine smile on her face. It looks like I’d chosen correctly. This is what she really wanted. To talk. She was trying to get me to figure it out. “Very well. I propose a game. Would you fetch us some liquor?”

‘Hangover incoming. The mare could probably drink you under the table. Look at the size of her.’

“Very well. Would wine be okay?” I stood and began walking to the kitchen.

“Something stronger. Gin, if you have it,” she said somewhat teasingly. She could sense my apprehension.

I did indeed have gin. This was gonna be a rough one.

“Shot glasses too. We will need them.”

I returned with the necessary game pieces. Midnight’s magic poured a shot for each of us. “Now then. Here is the game. We will ask each other questions. If the other party chooses not to answer, they must drink.”

“Perfectly simple,” I replied.

“Additionally you cannot ask a question that has been asked. If I ask you what your favorite food is, you cannot ask me.”

Interesting. Added an element of strategy. You could ask a question you knew the answer to just to keep the other person from asking you.

“So. Let us begin. As I am the client, I shall ask the first question.”

“Go right ahead.” The game was on. Let’s see where she took this.

“What is it that you do for a living?”

She knew the answer to that. She just didn’t want me asking.

“I am an escort. I make love to mares for money.”

Midnight nodded. “Excellent. It is your turn.”

I pondered. “Your cutie mark intrigues me. What’s your special talent?” Innocent question. I assumed it was a gimme.

She chose to drink.

“Wasn’t expecting that.”

“But the unexpected is so much more interesting. Perhaps I’m just a candle maker, but the mystery of me drinking might deceive you into thinking I’m more exciting than I am.”

It seemed there was more strategy to this game than I thought.

“My turn. How large is your member?”

Does she think i’m shy about that? “On the small side.”

“Confident. I like that.”

“If I was ashamed of it, I’d be a poor escort.”

“Indeed.” She looked at her glass and drank the shot. “That one was free.” She looked very smug. Sure of her victory.

“I’m not the only confident one it seems.”

“I’m just enjoying the gin.” A lie. She was flexing. “Your turn.”

“What’s your biggest fear?” I ventured.

She frowned. Debating whether or not to drink. “Being alone.”

“A standard fear. No reason to hesitate there, Midnight.” A light jab. I saw a tender spot and poked it. That’s when you really see what ponies are like.

“My fear is different.” Quite an odd statement. “It is my turn?”

I nodded.

“How is your relationship with your father?”

That was not so much a jab as it was an uppercut. Did she know about my past?

‘You’re thinking too much. She was just lashing out, hoping to hit a sore spot of yours.’

I drank. It was basically an answer on its own.

“Poor Guilty. Unwanted? Unloved?” Venom in her voice. She was on the offensive.

Things had taken a turn for the cruel. “Let’s not be quite so caustic. Or are you just trying to upset me?” I felt some anger forming in my chest. That sort of shuddering tension in your lungs that precedes actual rage. I was indeed learning what sort of pony she was. One who didn’t pull punches.

She closed her eyes pensively and nodded. “Apologies. You… struck a nerve. I’m sorry. It is your turn.”

I cleared my throat. “Well, in the spirit of being kind to each other. I shall ask a kind question. Do you prefer to be on top or bottom in the bedroom?”

“Top. I recognize that I am quite large, but I don’t care for being under ponies. They’ll just have to endure my weight.” She shrugged.

Coy smile. “Some ponies like being crushed under a larger mare.”

“Some ponies like you?”

“That is your question, then?” I smirked.

She blinked. I’d tripped her up. “It would seem so.”

“Yes, I’d rather love being under you. Particularly having you use my face like a cushion.”

She blushed again. Still stoic, but clearly intrigued by the prospect.

“It is once again your turn, you clever stallion, you.”

“High praise.” I pondered. What could give me some insight into her identity. “Where do you live? I don’t recognize you from Ponyville.”

“Canterlot, these days.”

“And before?”

“That’s another question.”

Damn. “Very well. Your turn.”

“Where did you live before ponyville?”

“Ever clever.”

“You simply showed your hand. I’m capitalizing on it.” Ever smug. Ever sure of herself.

‘Not quite. She set a trap.’

“No, I think you showed yours first. You didn’t have to say ‘these days’. You did that just to make me curious. You wanted to trip me up, and you did.”

She smiled delightedly. “Oh, I do like you, Guilty. You’re sharp.”

“Not sharp enough, it seems. Manehattan. I grew up in the slums and I’m proud of it.”

“Hardship can only make you stronger. Assuming you survive. Good for you: making so much, coming from so little.” That odd sense of motherly pride again. Almost reminded me of Ms. Smile.

This mare was inscrutable.

“Moving on,” I said.

‘Think, Guilty. What can we find out?’

“Are you Canterlot nobility? You’ve got an aura about you.”

She scratched her chin. “No. I am not a noble.”

“Had to think on that one?”

“That’s another question.”

“A rhetorical one.” I swirled my little shot glass. What could she have to think about? You’re a noble or you’re not.

“My turn,” she interjected. “What type of clients do you most enjoy?”

Back to my profession. Maybe it was time to flirt again. “I appreciate candor. Mares who know what they want and make it clear. I also like a mare who can keep me mentally stimulated. It doesn’t hurt when they’re great big mares who like to be on top.” Lurid smile. Suggestive tone. Bedroom eyes.

She blushed again. This time allowing herself to smile. A small flick of the tail. She liked that. “I would say flattery will get you nowhere, but that would be a lie.” She flipped her mane a bit. By Celestia, was this mare gorgeous.

My turn. “What kind of stallions do you like?”

She shook her head. “Ah ah, Guilty. You can’t repeat a question.”

I had a workaround. “You asked me about clients. That’s a work question. I’m asking you about your personal tastes. See? Entirely different.”

She looked impressed. She seemed to enjoy it when I was clever. “I like you more and more, Guilty.”

“Does that mean you’ll answer?”

“Indeed.” It was her turn to be seductive.

Holy shit could she be seductive.

Her gaze locked with mine. I was entranced. Her eyes were a lovely cyan. Her voice came like liquid lust. I honestly got hard just listening to her. “I like smart ponies. Ponies who can keep up with me. Ponies who can surprise me. Ponies who aren’t afraid of their shortcomings. Ponies who like it when large mares use their face like a cushion.” She bit her lip a little. It was sexy. Way sexy.

I was flustered, but in a good way. That proper excitement at the prospect of physical pleasure. She got my heart racing and I was enjoying it thoroughly.

She noticed my, admittedly obvious, arousal and decided to push further.

“If I were to walk around this table right now, how would you want me to touch you?” She ran a hoof along the rim of her glass.

‘Be descriptive. She wants a story.’

“Well, to be perfectly honest, my jeans are far too tight at the moment. I’d ask you to take off my pants. I’d want you to see just how hard I am right now. I’d want you to wrap your lips around my shaft.”

One of her hooves began to slide between her legs. “Keep going,” she insisted.

“Eager, aren’t we?”

She drank. I realized that she was counting that as my question.

“I’d want you to slide me in and out of your mouth. I’d want you to indulge in the taste of me.”

“Mmm…” She moaned as her hoof began to slide along her marehood. “I’d like that.”

“Nothing’s stopping you,” I hinted.

“Oh, but the game is still afoot. I couldn’t very well ask you questions with my mouth full.” She leaned back, moaning louder as she fondled herself.

Turned on as she was, she was determined to keep playing her little drinking game. I began to rub myself through my jeans as I continued. Even through the denim, it felt good. “Well, then I’d want to empty myself into your mouth. Have you swallow my load.”

She began to speed up her hoof. I could hear the wetness between her legs. “Oh, I do love how it tastes. Stallion has such a nice flavor.”

“Then I’d want you to crawl on top of me. Push me onto my back.” I did my best not to finish. She might actually want something physical after her game, and I’d hate to blow my load early.

She was panting at this point. “Oh, Guilty, you’re going to make us feel so good.”

“I’d want you to slide your hips along my torso.”

“MMmm… keep going.” Her wings stood on end.

Wait, she was a unicorn. I’m mixing her up with somepony else.

I digress.

“I’d want you to press your crotch up into my face.”

“Yes… Oh heavens above.” Her hoof was really going to town.

“I’d curl my tongue around.”

“Fuck… ah!”

“Flick it across your clit.”

“So close!”

“I’d dive deep inside you and twist around in your depths until—”

“AAAAH! BY THE FUCKING MOON!” Everything about her spasmed. She shook with violent pleasure.

Against all odds I managed NOT to cum in my pants.

“Hah… hah… Guilty, you truly are a force to be reckoned with. We enjoyed that immensely.”

“Yes, we certainly did,” I agreed.

She cleared her throat and began to regain composure. “Let me catch my breath. Then our game shall continue.”

Incredible. Didn’t even miss a beat. “Still not satisfied?”

“It’s not your turn, Guilty,” she chided. “You’ll just have to wait while I collect myself.”

She once again took a shot of gin for the fun of it. She wasn’t even a little tipsy. “Now then. You’ve only had a single shot so far. Let’s ask something to get some booze in you. I won’t ask about your other clients, that’s practically cheating.”

“You’re very kind.”

“Ah, I know. What are the circumstances of the worst breakup you’ve ever had?”

‘When she hits she hits hard.’’

My erection shrunk a little. The question was well worded. She’d guessed correctly that I did not want to discuss that. At least, it seemed like a guess.

‘You’re paranoid. Just drink.’

I took my shot. The alcohol made me shiver a bit.

“Huzzah! Success!” she proclaimed. Once more she clapped her hooves together happily. “It is your turn. Let’s see if you can make me drink.”

“Okay, let’s see.”

‘Come on, find a gap in the armor.’

“What’s your most embarrassing sexual experience?”

She shot right up, eyes wide. She drank immediately.

“That bad?” I stifled a chuckle.

She swallowed her gin, waving her hooves in front of her as if to dispel the question.. “There are quite a few bad ones, and I’d rather not consider all of them. I’d die of embarrassment reliving the entire terrible catalog.”

I felt some small victory in that. “Very well. It is your turn, then.”

She took a deep breath. “Let’s see. Maybe something embarrassing for you as well.”

“Hit me with your best.”

She rubbed her chin. “Have you ever… no wait, I can phrase this better. What happened when you… got caught touching yourself in public?”

I squinted. “The question presumes that I have been caught masturbating. In public.”

She nodded. “It does, but it can still be answered, can it not?”

Unfortunately it could. “Well, in the past I have on occasion entertained mares outdoors. One time in an alley my client and I were pleasuring ourselves when a stallion walked by.”

She clicked her tongue. “I was certain you’d drink.”

“Tough break. Anyways he stared for a few seconds while my client and I froze. Eventually he just walked away and we ran for it.”

She sighed, defeated. “Hardly embarrassing at all.” She took another non-required shot. How much gin had she had? She was as sober as anypony. “Your turn again, Guilty.”

“Thank you, Midnight. Do I keep trying to embarrass you then?”

She groaned. “I suppose it would only be fair. I warn you though, there’s a very long list of things I’d rather forget.”

‘Let’s be kind. We don’t want to just embarrass her into submission.’

“A different direction then. Let’s get philosophical.” I called upon an old memory of myself and The Professor talking late at night behind the scenes at the stable.. We were stoned at the time. “Can we know for sure than anything is real?”

She looked curious. “Quite a pivot. You continue to surprise. No, we cannot, but it hardly matters. If reality is real to us, it’s not worth considering anything further. ‘I think, therefore I am.’ Hay Cart said that.”

I may have bitten off more than I could chew. She seemed quite versed in this subject.

“In the vein of philosophy: do you believe free will exists? Our brains just respond to stimuli and act upon them. Are we just machines of blood and bone, or is there something more inside of us? Something that defies the idea of cause and effect?”

“I…” that was a tough one. I’d thought about it before but never terribly seriously. “It has to. I think. I consider. I make choices. If I don’t have free will, what am I experiencing? Is every decision I make an illusion?”

“Is that your question? Or is it part of your answer?”

I rubbed my eyes. The booze and the late hour were catching up with me.

“My answer is yes. I have free will. I refuse to believe otherwise.”

“Interesting.” She chuckled ever so slightly. “Don’t worry. To this day we still don’t know what to believe.”

I raised an eyebrow. “Who’s we?”

She hesitated. I’m not sure about what. “We as in ponykind. There’s no clear cut answer out there. Don’t worry. I won’t count that as your question.”

Ever strange, this one. “You are a fascinating mare.”

“That’s not exactly a question.” She smiled. “But thank you.”

“Alright, another philosophical question.” I rubbed my hooves together.

‘Maybe we can spook her a little. Knock her off her game.’

“Can murder ever be justified?”

“Yes.” No hesitation. No apprehension. Honest. Forthright. Unapologetic. “Some ponies say that there’s always a better way and those ponies are wrong.”

Scary. It took The Prof. and me hours to even reach the conclusion that maybe if the world depended on it, murder could be justified. She, on the other hand, seemed so confident in that from the get-go that it made me wonder…

“Have you ever killed anypony?” she asked.

I didn’t answer. I couldn’t. It was such an outrageous question. “No… of course not…why would you ask that?”

She shrugged. “You asked if murder was justifiable. I thought maybe you felt guilty about somepony you killed long ago.”

“Well… no… I haven’t…”

“Your turn. That was my question.”

“Yes… yes it was.”

I felt goosebumps on my neck. I swallowed audibly. My attempt to rattle her had failed miserably. I was the one who ended up thoroughly shaken. I couldn’t think of anything clever, so I asked something almost aggressively banal. “What’s your favorite food?”

She had a deadpan expression. “Pancakes.” Unimpressed with my question, it seemed. “Moving on. What’s something interesting I could ask… OH!” She clicked her hooves together again. She liked this one. “Have you ever taken advantage of somepony’s feelings for you?”

My eyes went wide. I could suddenly feel my heart beating in my ears.

I couldn’t answer.

Had she just said that?

My jaw simply dropped.

“Was I unclear? Have you ever pretended to be in love with somepony in order to gain something from them?”

I couldn’t

How did she…

“Are you going to answer?” she asked.

I couldn’t

I drank

The gin was sour

“Veeeeeery interesting.”

I couldn’t find words.

“We’ll come back to this. Anyways it’s your turn.”

What was happening?

How did she know?

Who was this mare?

“How much do you know about me?” I wasn’t even thinking about the game. I was just demanding an answer.

She drank.

“DId I… did I trick someone you cared about?”

She drank again.

“Who are you?!” I screamed. I was shaking.

She drank a third time.

“Okay. That was three questions. It’s well my turn.” She was unfazed by my outburst.

I stood up. Marching around my table to face her directly. “I don’t want to play anymore. I want to know who you are.”

“Ah ah ah, Guilty. What happened to your golden rule? Pure discretion. Don’t go digging into my past.”

“You’re digging into mine.”

“True enough.”

“Either tell me who you are or leave… please.” I hated this. Who was this? I wanted her out of my home. Did she know Sunny? Did she know one of the other unfortunate mares I tricked?

“Last question. I promise. Then I’ll leave.”

“No.”

She stood up. I was reminded just how imposing she was. “I insist.”

I found myself terrified. “Just… fine… ask your question.” I stared at the floor.

Her hoof found my chin and wrenched it up to look at hers. Her eyes were a cold and deadly ocean-blue. The last color a drowning pony sees. “Are you a bad pony, Guilty?”

I swallowed.

I knew the answer.

“Yes.”

Her sturdy hoof released my chin. She closed her eyes and sighed heavily. She was calm. I was not. This whole thing was surreal. This didn’t feel like reality. It felt fake. Like a scripted nightmare.

“Guilty.”

“Are you going to leave or not?” I was shaking.

“You are wrong.”

I shook my head. “What?”

Her eyes were kind again. Not the empty eyes I’d been looking into only moments ago. Her gaze was almost loving. I felt embraced by her mere presence. “You are not a bad pony.” Why was she telling me this? “You have hurt many ponies. You’ve hurt ponies in terrible ways.”

“I… I know… that’s why—”

“But that doesn’t make you bad.”

I wiped a tear from my cheek. I’d started crying. When did that happen?

“Guilty… no one goes through life without hurting anypony.”

“B-but I…”

“There are very few BAD ponies in the world. Most ponies are just doing their best. Some ponies hate you, rightfully so. But some ponies love you, rightfully so.”

A hoof wrapped around me, pulling me into her chest. She stroked my mane. I don’t know why, but I didn’t resist. It somehow just felt correct.

“I… I don’t deserve them…”

“You don’t. No one ‘deserves’ to have good ponies in their life. We are who we are, and sometimes other ponies choose to spend part of their lives with us.”

“But… but what about the ponies I’ve hurt.” I started to weep. Sobbing with my whole body. The sort of crying that only happens when you feel truly and utterly vulnerable.

“Nopony you blackmailed ever died because of it. None of them got hurt so bad they couldn’t bounce back. Yes… you hurt those ponies. But they’ve all begun to get back on their hooves. To varying degrees.”

“How can you know that?”

“We know. Trust us.”

For some reason I did.

“Why… why are you telling me this?”

“Because, Guilty. We care about you. We care about everypony. We care about the ponies who love you. Who hate you.”

“But I… I… I don’t understand… how I can… how I can be a good… good… pony. After e… e… e… everything I’ve done” I could barely form words. At this point I was getting tears and snot on her coat.

“Everypony has the capacity to turn their life around. You’ve certainly started to. You helped ponies you didn’t have to. Helped the mantle ray. You’ve fallen in love. And a pony has fallen in love with you.”

“But… but… I never got punished for the things I did. I never… I never asked for forgiveness. Never apologized. I just… I blackmailed them and disappeared.”

“It is true. Some of those ponies had their marriages and lives turned upside down. Some simply paid you to make you vanish. But here’s something thou might not believe. Some of those ponies are still together. Some of those ponies blame themselves more than they blame thee. And some of those ponies have even forgiven thee.”

She’d begun speaking so strangely. Like a knight from a fantasy novel.

“They can’t… they wouldn’t…”

“But Guilty, thou have hurt thyself over thine own wrongs more than anypony else ever could or would.”

“But I… I deserve it.”

“Maybe. But dost thou intend to punish thyself forever? How much must thou make thyself suffer before thou art forgiven.”

“I…”

“Guilty…”

“I…”

“Guilty, listen…”

“Wh-what?”

“Thou can stop. Stop thinking of thyself as a villain.”

“But… but it still feels like I am. I still feel like… I need some sort of divine punishment.”

“Shall we oblige you, then?”

“H-huh?”

Pain. She slugged me. Hard. I toppled back, landing square on my ass.

“Fuckin’... ow!” I rubbed my cheek.

“All is forgiven.”

“Wh-what?”

“We have struck you on the cheek. Look, thou art even bleeding. This is the punishment we deliver unto you. And now… we forgive you.”

It felt like the world was gone. Only her words remained.

“Now… rest. And when thou awaken, know that thou art allowed to be happy.”

I woke up on the floor of my living room. The fire I’d lit had burnt out. Drool was dried on the side of my face, which still smarted from Midnight’s punch. My breath reeked of gin. My back was sore as hell.

There was no sign of Midnight, with one exception. I found payment on my kitchen counter. One hour’s worth.

The whole thing felt… impossible. A gorgeous giantess. A battle of wits. Shock and horror followed by emotional catharsis. I still don’t know who she was. How she knew the things she knew. Why she tried to help me.

When I read back what happened it should objectively be scary. Some magical mind-reading mare, with impossible knowledge. If not for the coins and the half-empty bottle of gin I’d swear it was a dream.

But somehow I’m not scared. I feel like she really was just trying to help me.

Midnight, I don’t know who the fuck you are.

But thanks.

I think I’m a little more prepared for the upcoming meeting with Applejack.