Despite having escaped the ornery clutches of several alicorn Princesses, Anon’s situation was far from what he’d consider ideal. He’d managed to hitch a ride with a surly crew of sky-sailing parrots, and diddled their fare Captain a handful of times, but therein was the problem. In a grand twist of fate, his flight from the Crystal Empire, while successful, had left him stranded in the middle of nowhere.
He hadn’t even heard of the remote village of Hope’s Hollow, yet that’s where his exodus had landed him. He knew that the little town was somewhere in the north eastern area of the Equestrian empire, and that the air was fairly chilly, but the place sure as hell seemed isolated as all get-out. He’d gotten a good look at the settlement from the air, noting a distinct lack of train tracks, which left him with a sinking feeling. Wherever he went from there, if he hoped to evade Celestia’s wrath, he’d more than likely have to do so on foot.
“Thanks for the help, Anon,” Calaeno remarked, shaking him from his thoughts.
Setting down a crate of oats, one of the many items that had been delivered to the secluded hamlet, he turned and wiped his brow. “It’s the least I could do.”
“Oh it’s far from the least you could do,” she snickered, sauntering over and brazenly fondling his package. “You sure you don’t want to come with us? I’m sure I could find a place for you…”
The flagrant flirting and the less than subtle grip on his equipment gave him a moment for pause. If he did decide to travel with the former pirates, he realized things likely wouldn’t end well. For starters, there was a damn good chance that Twilight had or would figure out who he’d hitched a ride with - secondly, and more prudently, he’d really rather not get too fond of plowing the swashbuckling avian. It wasn’t that he didn’t like her or anything, she’d actually been very accommodating on their two day journey, but he’d eaten and stuffed - not necessarily in that order - enough poultry to last him a while.
“I...I’d rather not get you guys in trouble,” he murmured, reluctantly meeting her eye.
“Well, if the Princesses do wind up catching ya, I’ll do what I can to organize a jailbreak,” she purred, pressing her soft chest against him. “After all, it wouldn’t be the first time I’ve broken the law for some booty.”
With that, she slipped her hand around his waist and firmly squeezed his backside. If nothing else, she was certainly forward for a woman, something the females of his homeland lacked, so he had to give her points there - heck, he’d even told her the real reason he was running away from the Crystal empire. Giving her a brief hug, before wriggling from her grasp, he marched towards the center of the town.
“See you later, lover boy,” she shouted from over his shoulder.
Anon merely waved and briefly looked back to give her one final smile. Aside from having to plan his next move, and figure out where in the hell he was, there was one other concern he had to get dealt with. Being trapped on a floating dirigible with an amorous avian, no running water, and only the clothes on his back meant he needed to get two things addressed as quickly as possible - getting a shower and hopefully finding something clean to wear.
As he steadily walked towards what had to be the center of Hope’s hollow, he surveyed his surroundings. A number of businesses circled an open area with a fountain at its center, and he’d passed a few houses, but there wasn’t much activity to be seen. Outside of a few ponies who’d come to help unload the airship, there wasn’t anybody out and about - then again, it was still relatively early in the morning.
Spotting what he presumed was a tailor’s shop, he slowed. The little business had no sign, nor any obvious markings about it, yet he could spot a handful of dressed mannequins resting inside. Figuring it was as good of a place to start as any, and hoping the proprietor would be kind enough to accept an IOU for his potential business, he brushed himself off and marched to the entrance.
A small bell above the door jingled as he saw himself in, yet he didn’t immediately spot anyone within. Creeping inside, inspecting at the neatly arrayed, colorful garments, he smiled. He wasn’t sure who owned the place, but they certainly seemed to have an eye for flashy attire. Slowing by the front counter, he peered into what seemed to be a backroom behind the checkout area.
Clearing his throat, hoping for a reply, he finally decided to greet his would-be host. “Hello?”
“I’ll be - oh crackerjacks - right there!” a voice from the back hollered, moments before he heard a small clatter.
“Uh - are you alright back there?” he asked, knitting his brow.
After another small crash, closer this time, he got his response. “Oh I’m fine! Just - dang it - wait right there!”
Though Anon was tempted to go and check on whoever seemed to be struggling, he patiently waited. Whoever was running the joint almost sounded like a stereotypically midwestern soccer mom, which both confused and amused him. Keeping his eyes glued on the doorway, listening to the sound of approaching hooffalls, he got his first look at the employee.
Though the pegasus mare appeared to be roughly the average size and build for her kind, there were a few things that stood out about her. The two-tone pink of her mane and tail contrasted sharply against her turquoise coat and plumage, but that was just one element that caught his eye. It was pretty rare for ponies to wear anything, which made her daffodil colored vest rather unique.
“Alrighty then, how can I…” she trailed off, seeing her highly atypical guest.
It wasn’t the first time Anon had left a pony speechless, and it more than likely wouldn’t be the last. Being the only human in a land of talking and oftentimes magical creatures tended to leave a fair many spellbound, even after the papers had published articles about him. Lowering himself into a squat, bringing himself closer to her eye level, he smiled.
“The name’s Anon,” he began, extending a hand towards her. “And you would be?”
“I’m Kerfuffle,” she chirped, trotting over to greet him, “and this is my boutique!”
“Well it’s a pleasure to…” he fell silent, noticing her prosthetic hind leg. He’d seen some pretty wild shit throughout his travels, but he’d never realized ponies could make artificial limbs. Closing his eyes, forcing himself to focus, he firmly shook her hoof. “Sorry about that.”
“Oh sorry nothin’! Trust me, if I had a bit for every time somepony looked at my leg, I would’ve retired to Silver Shoals by now - anywho, what can I do for ya, Mister Anon?” she snickered, taking a small step back.
“This is gonna sound really crazy, but I was wondering if you could help me get a pair or two of pants, a few shirts, and maybe a belt,” he sighed. As he inhaled, detecting the less than fresh scent permeating from his person, he hastily raised a finger. “And if you knew somewhere I could take a shower, that would be great.”
“You know, I might just have something that could help you out. A few diamond dogs came through here a couple of months back, and one ‘em ordered a few things. Not sure whatever happened, but the guy never came back - can you believe that?” she lightheartedly inquired. “Like I was saying, I could probably tailor them to fit you.”
Anon couldn’t help but smile, hearing the news. “That would be great! Honestly, if they can fit, I wouldn’t even care about the color.”
Turning around, with her mechanical leg gently squeaking beneath her, she trotted towards the back and motioned for him to follow. “Well the slacks are denim, so I hope you don’t mind blue. As for the shirts, well, it probably wouldn’t be too hard to make something similar to what you’re wearing.”
“That would be fantastic,” he responded, getting to his feet and walking behind her.
Moving past the counter and through the doorway, he found himself in a small workshop of sorts. Dummies, a drafting table, spools of yarn, and rolls of fabric lay scattered about the area, as well as a sewing machine and a number of other tools of her trade. While it certainly wasn’t the most organized space, she definitely appeared to know where everything was. Without skipping a beat, making a beeline to a rack of hanging garments, she produced a pair of jeans.
“Here we go!” she announced, freeing the article from its hanger. “Would these fit the bill?”
“Perfectly!” he merrily announced, overjoyed by his bit of luck.
Looking from the slacks to the man, she knit her brow. “Oh yeah, I’m definitely going to need to lengthen these a bit,” she mused, looking up his legs, over his torso, and to his beaming face. “Tell you what, since you said you wanted to wash up, how about you use my bathroom,” she continued, nodding over at a closed door.
As much as he would have liked to stay and lavish her with gratitude, the last thing Anon wanted was to put her off by his somewhat ripe fragrance. Navigating his way past the equipment and fabric, he smiled back at her. “It won’t take me long, I promise.”
Waving a hoof to dismiss his concern, she went back to rifling through the rack. “Don’t be silly, take as much time as you need! I’ve still got to find the denim I stashed away, don’t’cha know!”
Grinning like an idiot, feeling more at-ease than he had for the past few days, he entered the restroom, disrobed, and jumped into the shower. Even though he didn’t have the funds to pay Kerfuffle for the service and generosity, he made a mental note to compensate her - be damned if he knew how or when he’d have access to his meager funds, but he’d make it up to her somehow. Humming to himself, relishing the sensation of warm water cascading over his body, he stewed on his next steps.
There were a few sovereign nations he could run off to, yet he couldn’t say if one was better than the others. Even if the dragons, yaks, griffons, or changelings eventually turned him in, he could buy himself some time and allow his trail to grow cold. It may not have been the best plan, but, barring the intervention of some sort of all-powerful deity, it was the best he could come up with on such short notice. Having taken his time to enjoy the shower, realizing he probably shouldn’t use up all the hot water, he stepped out of the basin, grabbed a towel, and froze.
His clothes, which had been in a neat little heap beside the closed door, were nowhere to be seen. It was impossible that he could have misplaced his only possessions, since the room wasn’t all that big at all, leading him to one conclusion - someone must have taken them. With only one potential culprit at play, he pursed his lips and stepped over to the exit.
Cautiously cracking the door, taking care not to reveal his nude form, he peeked out into the workspace. “Hey - um - did you take my clothes?”
“Hmm? Oh, yeah, sorry about that! I wanted to see how much tailoring I’m going to have to do, but didn’t want to bother you - figured the easiest way to do it would be to borrow your outfit,” she responded from somewhere within the chamber. “Besides, it’s not like you don’t need them cleaned. I was going to throw them in the wash for you, once I was finished with them.”
Though her explanation made perfect sense, and was a further display just how good-natured she was, Anon was left in a pickle. With not but a towel to cover himself, he’d have to venture forth, confront her, and hope she had something - anything he could wear for a time. It was all well and good that ponies typically went around in the buff, but doing so himself made him less than comfortable.
Summoning his courage, he wrapped the towel around his waist, stepped out of the bathroom, and moved into the workspace. He knew it was silly to feel so awkward about the situation, given the odd circumstances, but he couldn’t shake a nagging feeling that something would go horribly awry. Sideling around a group of nude mannequins, nearing her drafting table, he stopped in his tracks. Standing at her desk, with her forehooves on the hardened surface, the mare contentedly wiggled her rear while cautiously snipping at the pants she’d shown him.
He had little doubt that she was a competent couteur, but the view made him wonder how and why she wasn’t a baker, because she had cake. Her soft, excruciatingly inviting buns gently swayed back and forth, practically begging to be squeezed. Though he’d messed around with the good Captain several times during his flight to the isolated village, the sight of such a plump ass set his heart thumping.
The perfect peek of her assets sparked a furious conflict within him. On one hand, his better judgement knew doing anything with or to her would end disastrously, adding to his growing list of debaucherous deeds - on the other, his id didn’t give a single, solitary fuck about his higher functions. His manhood gradually swelled, rebelling against his hesitancy, as he longingly peered at plush posterior.
Turning her head, glancing back at him, Kerfuffle’s eyes wandered down his frame and to the tented towel. “Enjoy your shower?”
“Y...yeah,” he stammered, tearing his eyes off her rump. “So - uh - you wouldn’t have anything I could wear right now, would you?”
“Can’t say I do, but I should be able to get these jeans refitted lickety-split. Actually, how about you take that towel off and come over here. I wouldn’t be much of a tailor if I didn’t get your measurements before I really get to work, would I?” she countered.
With a reluctant sigh, Anon walked over to her. It really wasn’t his fault that he’d always had a weakness for asses, but it certainly didn’t help matters that ponies were a perfectly fuckable size. Hoping his erection wouldn’t become an issue, yet keenly aware that it had already gotten him into a decent bit of trouble, he halted by the side of the table and quietly watched her work.
“Alrighty then, Mister, lose that towel,” she chipperly ordered, grabbing up a neatly wound length of fabric measuring tape.
He nodded once, before uneasily removing the towel and setting it atop the desk. The logical part of his mind told him that his hesitance was undue, since ponies saw one another’s junk on a regular basis, but a lifetime of modesty flew contrary to that fact. Stooping over, wrapping the tape around above his ankle, she steadily started her task.
“So you get many bipeds around here?” he inquired, attempting to distract himself from the awkwardness of it all.
“Not too many, no. Aside from that small pack of diamond dogs, the only other two-legger I’ve ever serviced was an abyssinian a few years back. Spread your legs for me, Hun,” she tutted, as she moved up his leg.
Everything went smoother than he expected, with her getting measurements of his calf, thigh, and the length of his limb without problem - that was, until she reached his waist. Rearing onto her forelegs, bringing her face to within inches of his semi-turgid length, she knit her brow and glanced at his cock. It took everything he had to stay cool and keep his mouth shut, praying she wasn’t about to remark on his equipment.
“If you don’t mind me asking, is this normal?” she asked, unabashedly studying his package.
“Yeah,” he admitted, rolling his eyes, “it just happens when I’m excited.”
“Excited?” she repeated, glancing up to his face. “You’re excited over pants?”
The question wasn’t undue, yet he’d failed to expect it. Looking down at her tush, feeling his mouth go dry, his mind raced. If he told her the truth, there was a very real chance the situation would become even less comfortable than it already was - if he lied, he ran the risk of her calling him out on his bullshit. As he weighed his options, considering how best to answer her, his indecision bit him squarely in the ass.
Hopping down to her hooves, she wheeled away from him, lowered her chest, and gazed at her backside. “Is it because of my fanny?”
Askance, Anon took a small step back. “W...why would you -”
“Well you were looking at it mighty hard,” she giggled, caressing her behind with her wings. “Say, that gives me an idea! Instead of you paying me, how about you give me a massage?”
“What?” he blurted, unable to believe his ears.
“You don’t have to if you don’t want to,” she continued, straightening back up. “I just thought that, seeing as how you seemed interested in my heinie, we could both enjoy ourselves a little. Walking around on this leg can be awfully tiresome.”
Seeing her lift and shake her prosthetic limb, the devil on his shoulder went absolutely wild. If she wanted him to give her a rubdown, it would be impolite to turn her down - after all, she had been nice enough to let him use her facilities and was crafting him some new garments. His willpower waned, crushed under sinful temptation, as he inched closer to her.
Kneeling down behind her, uneasily extending his arms towards her, he gulped. “I’ll try to be gentle.”
“I actually wouldn’t mind if you were a bit rough. You’re not gonna work the kinks out unless you really get in there,” she snickered.
Wrapping his hands around her lower thigh, just above her hock, he kneaded the soft flesh of her hind leg. While he was far from any sort of equine expert, he could tell she hadn’t been bluffing. Her muscles were taut and tense, possibly because she subconsciously bore more weight on the biological limb, but that wasn’t what had him worried; as he steadily moved higher, approaching her groin, his shaft eagerly twitched.
It wasn’t until his fingers came to within an inch of her nethers did he slow. He could continue giving her a legitimate massage, steering clear of her naughty bits, yet his curiosity and growing lust screamed at him to do otherwise. Given that his time with Cadance had been rather energetic, with the Princess basically thrust herself upon him, he’d never gotten the chance to appreciate a marehood before - as such, his lecherous interests won out over reason. Drawing his fingers to her snatch, delicately rubbing her velvety lower lips, he felt her shiver.
“Just tell me if you want me to stop,” he whispered, momentarily shifting his focus from her flagging tail to her face.
“I...it’s - Goodness me - it’s f...fine,” she sputtered, broadening her stance. “Actually it f...feels pretty good.”
With the green-light given, he gently rubbed and squeezed her sex. Unlike a human woman’s, her snatch rather meaty. As his digits glided over her entrance and to her backdoor, she winked. Though he hadn’t expected her to become aroused so quickly, the sight of her rosy pink interior sent blood rushing to his aching boner. Though he’d had no intention of actually doing anything with her, having simply intended on possibly copping a feel, his plans took a subtle turn.
Gathering his courage, he cautiously slipped his thumb to her clit. The results of his sensual exploration were as profound as they were immediate, eliciting a light whimper from her. Her legs trembled, her marehood excitedly winked and drooled over his hand, and she rolled her hips backwards. There was no doubt about it, she was thoroughly enjoying herself.
“Cheese and crackers- I’ve never had a massage like this before,” she groaned, bucking back against his hand.
Grinning despite himself, he continued running his thumb over the sensitive little nub. “Want me to try something else?”
Practically pressing her head to the floor, fully presenting herself, she enthusiastically nodded. “If it’s half as good as what you’re doing now, knock yourself out.”
Shifting his hand lower, he slipped his middle finger into her confines. He had no way to know if ponies had a g-spot, having only enough functional knowledge of human anatomy to know where the illusive area was, but he was about to find out. Questing deeper, rubbing his palm against her clit, he heard her gasp - jackpot.
Gently massaging the erogenous zone, feeling her quiver around his digit, his smirk broadened. He knew it was wrong, that he was far from the first person who should be tainting the friendly, innocent creatures of Equestria with depravity, but there was something undeniably hot about showing them the licentious light. Inspired, turned on, and swiftly forgetting where he was or what he was there for, he sank his ring finger into her.
“Oh my gosh,” she bleated, all but bucking herself on his hand.
Without even thinking about it, spurred by his mounting carnality, he grabbed his dick and started jacking off. If someone had told him he’d end up fooling around with another pony, after having bedded a married alicorn, he would have laughed in their face - having said that, his life had taken a rather salacious turn. It was like the cosmos was paying him back for all the years he hadn’t gotten any amorous attention, having him stumble into one lewd situation after another.
Licking his lips, fingering her with increasing speed, his passion soared. It was one thing to have a lustful mare use him, as the Princess of Love had, but this was something else entirely. The abject control he felt, getting the little pegasus more and more riled up, was intoxicating. Listening to her heavy, stuttering breaths, feeling her clench and spasm around his fingers, and seeing her legs shaking like leaves told him one thing - he was pushing her to the brink.
“Go ahead,” he whispered, egging her on, “concentrate on that feeling building up inside you…”
A handful of seconds and faltering breaths later, she reached her peak. Hot, syrupy nectar rushed from her depths, coating his hand and the floor beneath them, as she shuddered in bliss. Creeping closer to the limit himself, furiously jerking himself off, an idea struck him and caused his shameless masturbation to grind to a halt.
Withdrawing his digits from her exceedingly juicy canal, forcing himself not to lick his fingers clean, he leaned over and softly patted her thigh. “You ok?”
“J...jeepers,” she weakly croaked, shakily looking over at him. “Was that supposed to happen?”
He nodded back at her, as he sweetly stroked her tush. “Yeah, that tends to happen when a human does it,” he explained. “Say, since you mentioned wanting it a bit rough, you want a deep massage?”
“Will - Cough - will it be as good as that thing you just did?” she countered, piquing a brow while catching her breath.
“Mmmhmm,” he hummed. Straightening up, sidling directly behind her, he grasped the base of his tool. “Just stay right there, relax, and enjoy yourself.”
As he shuffled closer, kissing the tip of his length to her slavering entrance, he paused. If he went through with it, despoiling yet another creature in the magical land, he was making one more breadcrumb for the Princesses to follow. Looking to her face, momentarily torn with indecision, he saw the needy look in her eyes. He’d given her a taste, a small sample of the carnal delights he had to offer, and he couldn’t bring himself to leave her wanting. Driving his hips forward, his manhood gradually slid into her taut marehood.
Plunging into her, he couldn’t help but notice that she was far tighter than Cadance, likely due to being smaller in stature. Questing deeper, holding her waist, he didn’t stop until he bottomed out. Unfortunately, due to a disparity of their sizes, his endowment couldn’t quite fully fit within her, yet that wasn’t about to stop him. Securing his grip and bracing himself, he started pumping his hips.
Taking his time, allowing both he and the comparably diminutive mare to enjoy the warmup, a contented sigh escaped him. To his amazement, as he incrementally moved faster and faster, she began rocking back to meet his thrusts. While it was a pleasant turn of events, he was keenly aware that, despite it being her first time experiencing any sort of intimacy, she, like the Princess and Captain before her, took to the endeavor like a fish to water.
Her enthusiasm was beyond inspirational, and his pace slowly increased. His balls wetly slapped against her winking clit, as his length rhythmically pistoned into and out of her. Taking long, deep plunges, knocking against her doubtlessly fertile womb with each thrust, he lovingly ran one hand up her back and to her shoulder.
Regardless of the impulsive and unexpected debauchery, he found himself reaching a fevered pitch. The heavenly sensations of her clinging marehood and the sublime view of her jiggling rump practically demanded he give her his all, even if they were doing it in the back of her shop. Moving faster and faster, intent to deliver a particularly forceful thrust, he unsheathed his length, grit his teeth, and jammed his cock into her ass.
The mare howled out and nearly collapsed beneath him, yet it wasn’t from discomfort - quite the opposite, in fact. Throwing her rear into reverse, hilting him in the blink of an eye, she shot a crazed look. Though he hadn’t meant to fuck her in the ass, he’d unwittingly tapped into something neither of them knew she had - her inner butt slut.
Reeling from the sudden turn, feeling her fiercely constrict around his throbbing dick, it took Anon a moment to process what happened. Far more spacious and snug than her marehood, able to accommodate his entirety, her backdoor was, in a word, amazing - still, he wasn’t exactly sure how to proceed. There weren’t many who could handle surprise anal, especially without a copious amount of lube, so he wanted to make sure she wanted him to…
“Keep going,” she demanded, humping back against him.
Her vehement plea instantaneously addressed his concerns, virtually fueling his passion into a roaring inferno. If she wanted him to plunder her booty, by all the stars in the night sky, he was more than happy to pound her plush posterior into oblivion. With little more than his determination, strength, and his zeal, he set to railing her ass like it was his job.
Truth be told, it was the first time he’d gotten to try anal with anything, but he was far too worked up to properly relish it. Between the staggering sensations her backside afforded and the sight of her pucker being repeatedly drawn out and stuffed in, his vehement rutting reached a fevered pitch in record time. Draping himself over her back, plowing her butt like a field in spring, he kissed his way up her neck.
As strange as it was to admit, he was quickly developing a fondness for interspecies intimacy. He towered over nearly all of Equestria’s denizens, making him feel like a titan, which played to one of the largest kinks he harbored - size difference. Being bigger and stronger, not to mention more dominant, than someone he was doing the deed with was something he’d always fantasized about, yet it had taken him traveling to another world to finally make it a reality.
As he furiously screwed her from behind, driving her body forward with each thrust, she turned her head to face him. While he hadn’t anticipated any sort of romance from her, considering how bawdy things had become, that’s exactly what he got. Her lips pressed to his, and her eyelids drifted closed, as she heatedly made out with him.
Their tongues entwined, as they groaned into one another’s mouths. Moving in tune, filling the air with the steady Plap Plap Plap of their colliding bodies, each fought to please the other. It was a pleasant, albeit obscene turn of events. Butt-fucking a seamstress who’d been nice enough to invite him in, tailor some pants for him, and let him use her shower was certainly a new experience in his book, but he wasn’t about to complain - if anything, he hoped the experience would serve as a small recompense or her generosity.
On and on they went, pushing each other to the limit, before Anon decided to up the ante. Snaking one hand around her waist and to her abdomen, blindly fumbling for her crotch, he found what he was looking for. His fingers crept over the soft mounds of her teats, before he eventually grazed her nipple.
Delicately pinching and twisting the little bud of flesh, hearing her stifled whimper, he pulled out all the stops. His hips became a blur, as he jackhammered her rump. He knew the chances of him outlasting her were slim to none, since she’d only cum a few minutes prior, yet he did what he could to push her past the brink. Feeling her tense, just as he reached his limit, his wish was granted.
Every muscle in the little mare’s body went rigid, her essence gushed from her convulsing marehood, and her voice raised an octave, as the first shots of his seed rushed into her tush. He honestly couldn’t say who’d climaxed first, but it was a trivial concern - in the end, they both got their rocks off. Creaming her donut, while she squirted onto his thighs and over the floor, his ecstasy gave way to a blissful euphoria.
Pulling away, breaking their kiss, Kerfuffle dreamily peered into his eyes. “Holy heck, that was amazing!”
“I seem to have that effect on ponies...and birds…” he sheepishly muttered, rubbing the back of his neck.
“Well if you throw in another few sessions like that, consider your bill paid for,” she chuckled, pecking his cheek. “Shouldn’t take me more than a day or two to get everything ready for you.”
While he would have much rather banged and bolted, the timeframe of her craft was understandable. “Know anywhere I could crash? Maybe a hotel or -”
“Oh if you think I’m gonna let you stay anywhere other than in my bed, I've got news for you,” she purred.
The prospect of shacking up with her evoked an odd thrill within him, knowing she’d be getting more of his lascivious services. Patting her head, he straightened up and hauled his softening cock from her behind. Her pucker snapped shut, trapping all but an errant dribble of his seed, yet the small stream crept down her marehood and dripped to the floor.
Realizing it likely wouldn’t be the first mess they made, he bashfully grinned. “Got a mop?”
