Gentleman in Training

by Denim_Blue

Chapter Five: Not a Boy, Not Yet a Gentleman

The rest of the weekend passed by rather uneventfully for Full Bloom and I. Sunday brought with it an unexpected rogue storm from the Everfree, but the Hoofington weather ponies managed to weaken it to a steady drizzle throughout most of the day. With the weather being less than ideal outdoors, Full Bloom and I decided to head over to my place and enjoy watching a few movies on my laptop, among them being Forrest Gump and Spirited Away, the latter of the two being one that Full Bloom was quite fond of.

When Monday rolled around, I found myself with nothing to do. Full Bloom had to work, Alex was still out of town with Sugar Sweet, and Gabe was already receiving training at Gentlemen For Mares. As such, I was mostly left to my own devices for the next two days. I had spent most of the time walking about town, getting some much needed groceries, and reading up on my brochure from Gentlemen for Mares. Tuesday was only a little more eventful since Full Bloom came to my place and we had a nice dinner together. Nothing much aside from that, since she had an early morning the following day, so she unfortunately had to go home.

Wednesday morning came, and after having a glass of milk and an apple—didn’t want to spoil my appetite for the at-work breakfast—I showered, threw on a nice, collared short sleeve shirt and khakis, and made my way towards Gentlemen for Mares.

It was about nine o’clock when I walked into the main lobby of the Hoofington Branch building. I was greeted by the faint smell of cinnamon and nutmeg and a cheery smile from the receptionist. I recognized the mare as Manila right away.

“Good morning, Darren,” she greeted, adjusting her thick-framed glasses with a hoof. She had her silky white mane done up in a tight bun today, and her tan coat was complemented by a light yellow silk scarf. I didn’t want to call her out on it, but she seemed to have a penchant for looks that would have been seen about forty years ago back on Earth. She made it work, though.

“Morning,” I replied with a wave. “So, uh…?”

She giggled. “You’re actually a bit early. Silky and the rest of the staff that will be handling your orientation are in the conference room. Feel free to wait here, or head back there. Breakfast will be held after the introductions are made. If you want some coffee, though, I can get you a cup.”

“That would be great, actually, I could use a cup. If you got some creamer and sugar, I’ll take a little of both.”

She gave a nod and got up from her chair, coming back a short while later with a cup of coffee in one hoof. “Here you go!”

I took a slow sip and sighed. It was a rich blend, whatever it was. I was about to take a seat in the lobby when I heard a door open in the back behind Manila’s counter. She and I both looked up to see a white coated pegasus with a blonde mane walk in. She looked like she had been running a marathon; her barrels were rising and falling steadily, her cheeks were flushed, and she was sweating. I raised an eyebrow as I noticed the blue and gold form-fitting flight suit she was wearing. What was a Wonderbolt doing here?

“Oh, Pizzelle, glad you made it,” Manila said with a giggle. “I take it your superiors were keen on letting you leave last night, huh?”

Pizzelle groaned, “No, Lieutenant Soarin’ insisted I get all my drills in last night, and by the time I was done, I was too tired to make the flight here. I got up early this morning and got here as fast as I could…” She looked to me and studied me with a scrutinizing eye. “You one of the recruits?”

“Erm… recruit—oh, yes, I’m a… one of the new Gentlemen, yes…”

She frowned, clearly looking less than impressed. “Hm. Manila, how many did Silky manage to pull in?”

Manila shook her head in amusement. “Five Gentlemen, Pizzelle. Darren here was our fifth.”

“You don’t say?” She gave me a final once over, and clucked her tongue. “I sure hope you’re ready, kid. You’re going to learn to hate or love me by the time I’m done with you.”

Wait, did she just call me ‘kid’? “Well, I look forward to getting to know you.” I gave a smile and a nod. She grunted a reply, and turned back to Manila. “I got my luggage in the spare office with the cot. Silky’s still okay with me bunking down in there, right?”

Manila gave her a nod. “Yep, and if you need something better, I think we can find a nice futon for you to sleep on.”

“Don’t worry about it. I’ve slept on worse and been fine.” She made her way back through the way she came. “Later.”

I gazed at the door she exited through for several long moments before Manila’s amused chuckles stirred me from my thoughts.

“Don’t worry too much about her. She comes down hard on anyone she meets for the first time, but Pizzelle only means well. Her father was a member of the Royal Guard, and her mother works for the Canterlot Police Department. She was an only filly who grew up with two older brothers, so she comes off as a bit rough, but she grows on you.

“She’s a Wonderbolt, too,” I pointed out.

“Mm, well, technically she’s in the reserves. She still beats herself up over having not made it into the higher ranks, but she’s an amazing flyer in her own right. She’s usually helping train cadets, but has offered to help with getting you boys into shape… and now that I think about it…” Manila pulled out a folder from a small pile, and scanned it over quickly. “Yep, she’s also your pegasus teacher.”

“Uh… huh…” I took a sip of my coffee to hide the frown that was forming on my lips.

Manila just giggled. “Don’t worry, Darren. As long as you give her one hundred percent, you’ll earn her respect. She also makes amazing cookies, so there’s that, too.”

“I’ll remember that, then.”

The doors to the front opened, and I was greeted by the sight of Alex. He was wearing light blue long sleeved shirt and black pants. He had cleaned up his goatee a bit, too. In fact, as I took in his appearance more…

“Alex, did you get a haircut?”

“Hey, Darren. Yeah, Sugar Sweet’s younger sister visited yesterday, and wanted to try out my hair. Apparently, she’s a stylist in Fillydelphia. Does it look alright?”

“Yeah, I’d say so,” I said with a chuckle. “I’m just used to you letting your hair grow out for a while, then just getting a buzzcut. That looks like it was professionally done.”

Alex gave a grunt, running a hand through his dark brown locks. “Yeah… she may have gone a bit overboard. I didn’t want anything fancy, but I guess Sugar likes it.”

“How’s she doing, by the way?” I asked.

“She’s good, she’s good…” Alex chuckled. “She wanted me to get a list of your favorite kinds of sweets, by the way. Something about testing out some stuff with you guys. So, uh… if you have time, write down a list of like, five things for her. She’d appreciate it.”

I laughed, “That’s cute, Alex.”

“Lay off it, Gabe’s going to be giving me enough problems as it is, I’m sure.”

After Alex got himself a cup of coffee as well, he and I made our way to the conference room. Sure enough, there was Silky, along with a pale green earth mare with a red mane done up in two braids. She had what appeared to be two candied apples on either of her flanks. Next to the earth pony mare was a unicorn mare with dark orange coat that was bordering on brown. She had gray-blue eyes, a pale blonde mane similar to Silky’s, and a double-ended wrench cutie mark.

“And there’s the first of our group,” Silky said with a chipper smile. “Good to see you Darren, Alex.”

“Morning,” we both greeted.

“Darren, Alex, these two are Candy Apple and Silver Spanner.” She pointed to the earth pony mare and unicorn mare respectively as both waved in greeting. “Alex, Silver and Candy Apple here will actually be among your personal teachers, so you will be getting to know each other quite well in the weeks to come.”

Alex gave Silver a smile. “Pleased to meet you both.”

Silver Spanner giggled. “Likewise.”

“Well, you boys look younger than I was expecting,” Candy Apple commented with a chuckle. “Shoot, Silky, you should’ve warned me. I didn’t know we had a couple of studs this young joining. I might’ve bitten off more than I can chew.” She gave Alex an approving smile, and added. “Not that I’m complaining, mind you.”

Cute, she even has a southern Equestrian accent, I thought to myself. I couldn’t help but feel a twinge of jealousy towards Alex.

“Well, as soon as the rest of the boys and their teachers show up, we can get started,” Silky said. “In the meantime, you’re more than welcome to have something to eat.” She gestured to a table in the far corner. “We got some muffins, bagels, fruits—”

“Oh my god, Darren, they have waffles.” I turned to see that Alex had already made his way towards the breakfast buffet, and was stacking up about four waffles onto a plate. “Please tell me they have it… yes!” Alex lifted up a small pitcher of blueberry syrup, judging by the label. “Silky, whoever made this breakfast is amazing.”

“That’d be me,” came a reply from Candy Apple. “I hope you don’t mind, but I put apples and cinnamon in the waffles. Not sure if it was a great idea, so I have some waffles without anything in them.”

“Cinnamon apple waffles, Darren,” Alex continued. “This place keeps getting better.”

As Alex began digging into his waffles, I walked over to join him, picking out a few fruits and a chocolate chip muffin for myself.

As I sat down in a chair by the table in the center of the room, I heard three voices, one of them I recognized, down the hall leading to the room. I looked up in time to see Gabe, along with two other men I’ve never seen before, walk in.

Next to Gabe was an older man, probably around his mid-forties, with black hair that was peppered with streaks of gray. He stood about as tall as Alex, maybe a bit shorter, and had gray-blue eyes. He had a light dusting of five o’clock shadow along his face and very tan skin, though it looked natural, from years of living in warm weather. He was dressed in a short-sleeved red shirt and khaki pants on. He was carrying a briefcase in one hand, and had sunglasses resting on his forehead.

Behind the two was a young man about my age with wavy, dark brown hair that had faint streaks of copper color in it. His skin was a deep, olive tone, and much like the older gentleman, looked to be from years of living in warmer climate. His had deep brown eyes and a small soul patch under his lower lip. He was of similar size to Gabe, perhaps a little taller and a little more built.

“Oh, damn, Alex already dug into the breakfast,” Gabe said with a laugh. “Silky, you promised you’d hide everything until we showed up.”

Silky rolled her eyes and chuckled. “Let them be, Gabe, or I’ll tell Sugar Belle you’re misbehaving again.”

Gabe laughed, “Good luck with that. She likes to enable my misbehavior.” Gabe turned to the two men beside him and nodded to Alex and I. “These two are Alex and Darren.” He turned back to us. “This is Arnold,” he pointed to the older man, “and Martin. They started yesterday, so you two are the greenhorns around here.”

I smirked, and gave a nod to the two. “Hello. Hopefully Gabe hasn’t been too much trouble for you guys.”

Martin chuckled. “Nah, Silky keeps Gabe and me on a tight leash.”

“Not tight enough, if you ask me,” remarked Arnold, earning a laugh from Alex and myself. “Gabe can make a sailor blush with the number of dirty jokes he has.”

“Aww, come on, Arnoldo, you know you love them.” Martin chuckled as Arnold just smirked and shook his head. “It’s part of our calling as humans living in this wonderful land to spread dirty jokes and innuendos, after all.”

“Silky, why did you hire this boy again?” Arnold asked with genuine mirth in his tone, thumbing to Martin.

“He had a nice smile. I’m ashamed to admit, he had no difficulty in convincing me to hire him. It was Manila that recommended him to me, though, so you can blame her,” Silky replied.

“Gabe 2.0. Wonderful, just what we need,” Alex mumbled under his breath, earning a chuckle from me.

Silky cleared her throat, getting everyone’s attention. “Alright, well, we still are waiting on some of the teachers and other staff… and I think I hear a few more coming this way now.”

Sure enough, the room was suddenly flooded with color and femininity. Unicorns, pegasi, and earth ponies, all of them mares, walked into the room. Soon, there was about sixteen or more mares standing and sitting near the front of the room by Silky. They varied in build and the manner they carried themselves.

Now, I’m not going to lie; I was a little flustered with having so much attention focused on me, at least partially so. Several mares even winked playfully when I looked to them. I did my best to return their attention with a smile, though I think a few of them could tell I was a bit nervous if their giggles were any kind of indicator. Kind of odd, given the fact that I’ve already been intimate and was dating a wonderful mare right now. You think fluttering eyes and playful waves would be nothing for me, but nope, it still got a reaction out of me.

Then again, having over a dozen mares looking at you and openly flirting with you at once was a bit much, I suppose.

“Right, well, now that we’re all settled,” Silky began. “Welcome, all of you. I know a few of you have been here for a day or two now, but let me officially welcome you boys to Gentlemen for Mares. For the next few weeks, we’ll be training you all on everything you’ll need in order to become effective Gentlemen. We’ll be covering topics such as social norms, fashion trends, history, body language—”

“Don’t forget about sex,” added a mare in the group, earning a giggle from a few others.

Silky, being a good sport, just smiled and rolled her eyes. “Yes, thanks for the reminder, Windsweeper.”

“Anytime!” replied the mare.

Silky continued, taking a step forward and taking a clipboard from one of the mares that had entered. “Alright, now, before we get too deep into this, I think we can spend a bit of time so that you can meet your teachers personally. That we can all get an idea of who we are, and see where to start with each of you as far as training goes. Yes, that includes you, Gabe, put your hand down.” There was a chorus of chuckles and giggles as Gabe sighed dramatically. “Now then, first we have Martin…”

I watched as Martin went with three mares to a corner of the room, among the trio of ponies being the one who had made the remarks earlier about sex to Silky. Eventually, I was the last one to be called, and was greeted by three mares who gave me friendly smiles.

“Good morning, Darren,” greeted the unicorn pony of the trio.

Following behind her was the mare with the brace that I saw before, as well as Pizzelle, who was still in her flight suit. The unicorn had a pink coat with a bi-colored mane and tail consisting of two different shades of light blue. She wore a frilled dress saddle on her back, and had a choker with a purple gem around her neck. For a finishing to touch she had a light violet bow tied up in her stylish mane.

Beside her was Pizzelle, who looked a little more enthused to be here now, though she was still looking me over with a somewhat bored look. I decided not to let it get to me; Manila said to give her time, after all.

Last among the three was the earth pony with the brace. She had a light, sandy-yellow coat with a bi-colored mane of white and very light blue streaks. She had three apple slices for a cutie mark. “So, you’re the one that Silky said helped get this new program at the Hoofington branch started, huh?”

I laughed, waving a hand as I shrugged. “Sorta, but I think she blew it out of proportion by calling me a lifesaver. Regardless, she offered me the job, and I figured it’d be worthwhile.”

The unicorn smiled. “So I see. I’m Royal Ribbon, by the way.” She held out her hoof, and gave me an expectant look. I took it after a moment’s thought and shook it in greeting. She raised an eyebrow, an amused look on her face. “Hmm… that’s not what I was expecting…”

The earth mare chuckled. “Be nice, Ribbon. He’s just started.” She gave me a small smile, then added. “I’m Ambrosia, by the way, and this here is Pizzelle.”

I looked to Royal Ribbon, then frowned. “Uh… did I do something wrong?”

“No, no… well… not quite.” Ambrosia gave Royal a light nudge. “Ribbon here is just used to being doted on.”

“A lady should expect nothing less,” Ribbon said, though the playful tone in her voice was anything but serious. “Don’t worry about it, Mr. Halverson. We’ll have you up to speed in no time.”

“Physical speed, on the other hand,” Pizzelle cut in. “You’re not really… built, but you look alright. You could stand to gain a bit of muscle, though.”

“So I’ve been told. I blame it on my mother’s genes. She’s a fairly small woman.”

Pizzelle cocked an eyebrow, but smirked. “Well, then I guess we’ll just have to kick those genes around a bit and tell them to knock it off. By the time we’re through with you, you’ll be the envy of every man and stallion in Equestria.”

“I’ll try not to disappoint you, then.” A sudden thought came to mind, and my eyes widened as I looked back to the unicorn. “Wait… Royal Ribbon…” I studied her a bit. “You’re… not from Canterlot, are you?”

“I am, actually, yes. It’s easy to see, isn’t it?” She sighed. “I’m afraid my love for extravagancy is a hard habit to kick.”

“You’re not quite the most athletic pony, either. You could probably stand to lose a feewwwww…” Pizzelle’s words died on her lips as Royal Ribbon turned to her with a level look. “Your tail is a bit long. Maybe lose a few inches at the tip so it doesn’t get dusty.”

Ribbon arched an eyebrow, but said nothing further on the topic, instead returning her attention to me. “What were you saying again, Mr. Halverson?”

“Please, you can call me Darren. What I was going to ask, though, is if you’ve been on a radio program recently. Your name rings a bell.”

“Ah,” she laughed. “Yes, I was on True Talk last a few days prior.”

“Huh, so you’re a former politician, then?”

“A minor one, nothing special. I was more of a bureaucrat who wasn’t afraid to speak her mind. Earned me a few enemies in the castle, but Her Majesty seemed to appreciate my frankness.”

“Princess Luna or Princess Celestia?” I asked.

“Mm, both of them, actually, now that I think of it. Princess Luna seemed to have no qualms with me in the time I got to know her before she left to visit Earth.” She waved a hoof. “My apologies, this is a chance for you to know all of us a little better.” She gestured to Ambrosia, and smiled. “Dear, why don’t you tell him a little bit about yourself?”

“Oh, yes…” She scuffed a hoof. “Well, until about a year ago I worked for a construction company based out of Trottingham. I got into an accident, though,” she waved her leg in the brace a little. “It’s mostly healed, but my long-term disability ran out, and they let me go.”

“They can do that?”

“Mm, yep, and there wasn’t anything I could do about it, legally. I put up a huge fit, though.” She sighed deeply. “My sister-in-law works for the Manehatten branch of Gentlemen for Mares, and she suggested this job. I… haven’t been with many stalli—er, I mean, men, but I’m not a stranger to them.” She flushed a bit. “I look forward to working with you, Darren.”

I grinned a little, just enough to hide my canines. “Same here.”

“She’s quite the adorable little doll, isn’t she?” Ribbon asked me in a teasing tone. “Don’t let her demeanor fool you; she’s an animal in the bedroom.”

“R-Ribbon!” Ambrosia squeaked.

“Mm. She’ll probably break your pelvis if you’re not careful. All the more reason to get you into peak shape,” Pizzelle added, her lips curving into a small smile as Ambrosia began sputtering.

“W-what? I-I… that is not… it only happened once—I mean…” She was now beet red in the cheeks.

I laughed softly. “I suppose they’re just jealous, Ambrosia.” I winked to Ribbon and Pizzelle, who just smiled. “I’m still new to the world of mares myself. I just started seeing a mare not too long ago, actually.”

“Oh? Well, that should prove to be entertaining, then,” Ribbon added, her voice dropping a bit in volume. “Truth be told, the three of us have been brainstorming on ideas to help get you more in tune with the more… delicate portions of the job.” She rested a hoof on my knees and moved it in slow circles. “I’m sure it will be quite an enjoyable time.” she whispered huskily.

Pizzelle let out a snort. “Ease up, Ribbon. No need to scare the boy away.”

“I’m just letting him know what he has to look forward to,” Ribbon replied with a haughty look. “If you’ll excuse me, I’m a little peckish, so I’ll be grabbing something to eat for myself. Ambrosia, Pizzelle, are either of you hungry?”

“I’m good,” Pizzelle answered.

“No thanks,” Ambrosia said with a shake of her head.

With that, Royal Ribbon trotted off to the buffet table, humming a little tune to herself.

As soon as she was out of earshot, Pizzelle sighed. “She can be a bit overbearing, but she’s a good mare. She has more experience than either of us do, too.”

“Yeah, I was going to ask about that. You look like you’re a member of the Wonderbolts.” Pizzelle gave me a nod. “You must be really busy most of the time, so how’d you come about getting this job?”

“I get every other weekend off, unless we have a show that I’m needed for.” Pizzelle waved a wing a little. “I’m still working at becoming a member of the full-time crew, but the pay is okay for being in the reserve. That and I get three free square meals a day, and all the free oats that I want while training.”

“Really?”

“Yep. Gotta keep the energy up when you’re flying around all day.” She flexed her wings for emphasis. “But there have been a few weekends where I’ve need some companionship. I actually paid for a Gentleman on more than one occasion.” She cleared her throat, then added in a quieter tone. “I’ve been wanting to save up for a new place in Cloudsdale, though, and the slow season for us will be starting in Fall. So, instead of scraping by with the pay from being in the Wonderbolts when I won’t be performing, I decided to get a job here.”

“How did you hear about it, though?” I asked.

“A friend,” Pizzelle answered. “I’d rather leave it at that. Nothing bad, it’s just… they’d rather remain anonymous.”

I nodded in understanding. I had to remember that not everyone had a positive opinion about this place.

“So, what about you, Darren?” Ambrosia began. “What brought you here?”

“Long story short, I got let go from my old job and was unemployed for less than a whole day before Silky hired me. She apparently had a good feeling about me. Before that I worked for Ecosystems for Equestria as a field researcher in the Everfree Forest.

“Wait, you’ve been in the Everfree Forest?” Ambrosia asked. “I hear that place is dangerous.”

“It is, if you’re not attentive. That’s why we had two Royal Guards accompany us any time we went into the forest.”

“Huh, that’s kind of cool. Is it as bad as they say it is?” Pizzelle asked.

“I got bit by a Vampiric Jackalope once, but other than that, I came out with only bug bites and some rashes. Then again, I’m a human, so maybe I don’t smell as good as a pony to a manticore or whatever is lurking in there.” I laughed when Ambrosia’s eyes widened a bit. “We never ran into anything bigger than a timberwolf, and they usually scamper off if you make enough noise as a group.”

“What’s this I hear about timberwolves, now?” Royal Ribbon asked, having returned with a plate of fruit floating in her violet magic.

“Darren was just telling us about his escapades into the Everfree Forest for his job,” Pizzelle replied. “Apparently he’s been bitten by a jackalope before.”

“Vampiric Jackalope,” I reiterate. “There’s a big difference. One eats carrots, the other will try to eat you.”

“Good heavens, I hope it wasn’t too bad of an injury.”

“Nah, it healed up after I got it looked at by the nursing staff back in town.”

“Well, I’m not sure how much more time Silky will be giving us before she goes through orientation, so I suppose I’ll start by saying that all of us look forward to working with you, Darren.” Royal Ribbon batted her eyelashes before slowly biting down on a strawberry. She chewed it daintily while Pizzelle rolled her eyes and Ambrosia giggled in amusement.

“You’ll be seeing plenty of me, though,” Pizzelle added. “Between mock dates, education on social stuff, and fitness training, there’s going to be very little time that you won’t be seeing this mug.” She grinned. “Get used to me, otherwise you’re going to be in for a bumpy ride.”

“She’s referring to the ride being in the bed, by the way,” Ribbon added, earning a laugh from Ambrosia and myself.

The clopping of Silky’s hooves got our attention, as well as the rest of the room. The buzz of conversation died down as Silky smiled to all of us. “I hate to be the one to cut into the conversations, but we do have the rather dull, but important, task of discussing contractual obligations, your rights as employees, and so forth. The usual song and dance from what I’ve learned about human workers’ rights. Anyway, the sooner we can get this bit over with, the sooner we can get the actual training for the job underway.”

What followed next was a good two hours and some odd change of discussion on company work ethics and policies, and the typical legalese that came with any job in the modern age. While I took in what I could, it was hard to really listen without dozing off. Thankfully, Pizzelle was kind enough to poke me in the side every time I started zoning out. Though, in hindsight, she may have been doing it to amuse herself more than anything.

The second half of the orientation talk was pretty interesting, though. It talked more about the actual job, and what we as Gentlemen were expected to do. I had the papers with the guidelines and rules, but I could more or less sum it down to a few things: don’t be a jerk to your clients, remember you have the right to leave a client if you feel unsafe or uncomfortable and vice-versa, take care of yourself, and to always inform your Handler if there is a change of address or anything else that was vitally important. One thing that really sounded interesting was the system of preferred clients. Apparently, if a Gentleman enjoyed a particular client, they could request that they be given preferential status after talking with their Handler on the matter. Apparently, that gave clients a nice discount as well as more flexibility in scheduling.

Kind of neat, actually, considering it wasn’t uncommon for clients and Gentlemen to form bonds of sorts. It seemed like the company was almost encouraging bonding, in a way. It gave the company a more personal feel to it.

It was almost noon by the time Silky had finished the talk. I looked to see that Alex was currently scrawling down a few things on some paper he got from Silky, Gabe was chewing on the eraser of his own pencil, Martin was quietly flirting with one of the mares, and Arnold was closing the clasps of his suitcase while sharing a quiet conversation with one of his own teachers.

“So, you get all that?” Ambrosia asked.

“Uh… I think so,” I said with a laugh.

“Really? Because I still can’t remember all of it,” she remarked with an amused smile. “Must be a benefit of attending college, huh?”

“You get pretty good at taking notes after years of doing it,” I admitted with a shrug. “Sadly, not all of us are particularly gifted students, right Gabe?”

“Hey, C’s get degrees,” Gabe countered.

I gestured to him with a look that simply said ‘there you go’ and Ambrosia giggled further.

“Well, now that we have that out of the way, let’s take a quick break before we give a tour of the facility.” Silky said, stretching her own wings a bit and rolling her neck. “Oh, and Martin, while I appreciate the flirting, please keep the bedroom eyes and winks to a bare minimum when your supervisor is trying to explain your job to you, hm?” She had a smile on her lips, but I could see the serious gleam in her eyes.

“Whatever you say, Silky,” Martin replied with a smile.

So, with that, I made my way out of the conference room, finding myself being accompanied by Ambrosia herself. Royal Ribbon was talking with one of Gabe’s teachers, who to my surprise was a thestral.

“Huh, I didn’t notice her earlier,” I remarked with a smile.

Ambrosia followed my gaze and smiled softly. “Ah, that’s Dawn Weave. She’s from Hollow Shades, but moved here with her siblings about a year ago. Her brother works night shift at the steel mill, and her sister’s an officer for the local constabulary.” She sighed softly. “The poor girl... Dawn Weave was dating a stallion in town for a few months before he left for Las Pegasus. She didn’t feel right leaving her siblings behind, but he was set on moving. She was a bit broken up over it.”

“Dawn Weave, huh? That’s a pretty unique name for a thestral.”

Ambrosia let out a soft hum. “She likes early mornings, right around sunrise. She’s also a poet, and likes writing just when dawn is approaching and the birds are waking up.”

“Sounds like you know her pretty well.”

Ambrosia blushed. “O-oh, well, she and her siblings are my next door neighbors. They’ve helped me out a lot with things while my leg was healing up.”

“You live alone?” I asked.

“Yes, but I choose to. I had several stallions ask me out when I while I was working, but…” She frowned, clearly thinking her words carefully. “I… never had much of an interest in them. I mean, I’ve dated a few stallions when I was younger, but…” She shrugged. “I just wasn’t that eager to go looking for one to start a herd with, you know? My parents were always on my case about it, which didn’t help.”

“I know that feeling.”

“Hey, Darren,” came the voice of Pizzelle. I looked around to see her approaching me with a folder tucked under a wing. “Silky wanted me to give this to you. It’s the curriculum for your next few weeks. Try to get an idea of what to be prepared for, and make sure you keep track of any important dates. You’ll be doing most of this on your own outside of fitness training with the rest of the boys, so no one is going to be holding your hand.”

She offered me the folder, which I took and opened up. I perused through the papers, coming across a list of some of the things that will be covered: Canterlot social etiquette, proper table manners, popular pony terminology vs. popular human terminology, brushing tips, current trends in Equestrian fashion, Equestrian music…

The list went on and on, and I noticed a few pages in that the subjects became a lot more inclined towards the intimate subjects of the job: level one positions, level two positions, dealing with clients in heat, how to deal with ‘clingers’, Magic Boosters and how to properly use them, human vs pony erogenous zones…

“Damn, you folks don’t fool around,” I murmured, sifting through the rest of the papers. Most of them were bullet-pointed notes on things to remember. I’d look them over as I needed to, but for now, I closed the folder.

“Don’t get too excited; it’ll be a little while before the most of the fun stuff starts… well, Ambrosia here might give you a go a little early, but only because she’s been looking forward to this since we all finished our own training.”

“Pizzelle…” Ambrosia let out a huff. “I haven’t been that bad.”

“Okay, okay, Ribbon’s been worse.” Pizzelle leaned close, and said in a voice just above a whisper. “Word to the wise, Darren; Ribbon’s all sorts of kinky in the bedroom.”

“Is that so? Strange to hear that coming from a mare who’s a fan of roleplay and always being the dominant one when rutting.”

The look on Pizzelle’s face was priceless. I had to force down a smile as she turned several shades of red and her eyes widened. She spun around to see Ribbon giving her a very smug look.

“R-Ribbon!”

The pink unicorn paid no mind to the pegasus as she walked up to me. “Fret not, Darren, I may have certain… inclinations when it comes to intimacy, but I assure you that I will never do anything that you are uncomfortable with. I may try to encourage you to give a few things a try, but I shall never push too hard.” She looked over her shoulder, and gave Pizzelle a cheeky grin. “I wouldn’t worry too much about Pizzelle, either. She talks tough, but she’s a real dear once you get to know her.”

I decided to remain silent as Pizzelle gave Ribbon the mother of all annoyed glares, her wings flaring up a bit as her ears folded back a little. She eventually let out a deep sigh, and snorted. “Okay, I guess earned that one, Ribbon. I didn’t mean anything I said in a bad way, though.”

“Nor did I, Pizzelle. I simply felt it wasn’t right to bite back a little, as it were.” Ribbon turned to me, fluttering her eyelashes as she met my gaze. “Besides, I’m sure Darren is eager to work with us.”

“I’d be lying if I said otherwise,” I replied.

“You see?” Ribbon said, waving a hoof to me. “There’s no need to worry, Pizzelle. Come now, I believe Silky is going to give us that tour she was talking about.”

Silky guided our group through the modest building. Aside from the front lobby where we came in, there was a room behind Manila’s desk where they kept records, both in a file cabinet and on a computer, as well as a hallway leading to the back entrance. The building also had a break room and lobby where Silky had interviewed us, a weight room, Silky’s office/lounge, and a few spare rooms that served for handlers to do paperwork, and in Pizzelle’s case, make their home for the time being.

The back entrance of the building lead to a rather spacious, fenced-in yard. There was a patio with wooden reclining chairs overlooking an underground pool. Further off was a small basketball court and a horseshoe pit.

All in all, it was a pretty nice setup.

“While this is your place of business, we tried to make it a welcoming place as well for all of you, both Gentlemen and handlers,” Silky said as she lead us out onto the lawn. “The pool is open for employee use at any time, and we have sports equipment in the closet of the south office room if you ever want to play a game.” She smiled as she turned to face all of us. “Any questions?”

“Uh… yeah, actually.” I turned to see Gabe raising a hand. “Skinny-dipping in the pool… yea or nay?”

The question itself seemed to catch Silky by surprise. She blinked twice, and quickly schooled her features, giving Gabe an amused grin. “Well, I suppose since it is a fenced in yard, there’s no harm. I mean, us ponies don’t wear clothes that often as it is. Just don’t go flaunting your stuff to the neighbors.”

Gabe fistpumped while Alex and I facepalmed and groaned respectively.

When the tour came to an end, Silky excused herself to get some paperwork finished that needed to be mailed out by tomorrow. Like the rest of the guys, I was pulled away by my respective teachers, who seemed all too eager to have some time alone with me.

Interpret that however you like.

So, about a half hour later I was sitting outside a small café, sipping on a coffee while Royal Ribbon, Pizzelle, and Ambrosia chatted away about various things. Mostly small talk; family, where they grew up, latest news in the social world of Equestria. I remained mostly silent, contributing my thoughts only when asked.

“Mm. Perhaps this should be considered your first lesson, Darren,” Ribbon said, twirling a lock of her hair in a hoof. “I know you’re not trying to be impolite, but it’s also important for a Gentleman to be up to date on the latest things in Equestria.”

I gave her a sheepish grin. “I… have to admit, talking about the latest Equestrian trends has never been my strong suit.” I shrugged as Pizzelle gave me an understanding nod. “Still, I’m willing to get to a level where I can at least know what’s going on.”

“That’s a wonderful attitude to have,” Ribbon replied. “I suppose we could start by asking if you’ve ever been to Manehatten.”

“Briefly, back when I first arrived. I took a train from there to Hoofington, and to be honest, I’ve spent the majority of my time on Tellus living in central Equestria.”

“You’ve never been to Neighagara Falls or Las Pegasus?” Ambrosia asked.

“Nope. I live a pretty frugal lifestyle. Money’s never been much of a thing with me; I think I’ve spent more on friends and family than I have on myself. Just ask Gabe sometime, he’ll tell you how much he owes me without a hint of shame.”

Ambrosia hummed in thought, then looked to Ribbon. “You think Silky would put some money down on a trip to Las Pegasus?”

“The sooner he’s acquainted with the place, the better, I suppose,” Ribbon said with a nod. “We’ll worry about that later. For now, let’s talk about the latest news. Let’s see… ah, here we go.” Ribbon picked up a magazine on a nearby table and flipped through it to a section that appeared to be on fashion. “Here, do you have any familiarity with the current trend in manestyles?”

“To be honest, no, but I can tell you what I’ve noticed seems to be popular. A lot of mares have been going for manes with curled bangs, and the wispy tails seem to be pretty popular.” I shrugged as they gave me an expectant look. “Like I said, following trends has never been my strong suit.”

“That’s fine, Darren. We wouldn’t expect you to completely change yourself, but it will help you a lot to have a basic knowledge. You’re right, by the way. I myself have always had a love for the wispy tail fashion.” Ribbon emphasized her point by lifting up the end of her tail with her magic to show me.” If you go to Canterlot, though, manestyles are much more complicated. The Crystal Empire is a bit ‘outdated’ some would say, though I personally love the archaic look. Give it another ten years and the ancient pony fashion of braiding strands and jewelry pieces tied into the mane will be all the rage.”

Pizzelle rolled her eyes. “Sorry, Darren, I can’t contribute much to this. The Wonderbolts don’t have much in the way of manestyles and tail styles other than, ‘Don’t let it get in the way of your flying’.”

“One thing you’ll notice is that most stallions have shorter tails.” Ambrosia gestured to the ponies walking around the area. “It’s interesting, really, since most male humans also like to keep their hair shorter.”

For the next hour, Ribbon and Ambrosia gave me a lecture on some basic constants in pony mane styling and tail maintenance. Pizzelle, while less inclined towards such topics, did mention a few things, like how one could tell if a mare or stallion served in law enforcement or the Royal Guard. Trimmed tails and manes were the typical thing to see for guards and officers of the law.

Ribbon produced a brush at one point and ran it through her mane, all while giving me a few tips as she did so.

“How come most humans don’t put brighter colors in their hair dye?” Ambrosia asked at one point.

I laughed. “You’d be surprised how crazy some hair colors can be. Honestly, I have nothing against it, but I think the human tendency is to have hair appear to be a more natural color. Humans are mammals, and not many mammals have overly bright colors like you ponies do. We’re typically shades of brown, black, gray, white, but there are exceptions, of course. It’s all based on pigments in our skin and hair color.” I rubbed my chin, then added. “I’m sure at some point there was a divergence in the evolutionary line, and whatever creatures that had more natural colors to fit with their environment succeeded for various reasons.”

When I looked back up at the three mares, I saw Ambrosia and Ribbon giving me amused looks while Pizzelle had an eyebrow raised.

“Sorry, went on a bit of a tangent there, didn’t I?” I laughed. “I’ll try to rein that in.”

“You’d be surprised how many would find that rambling adorable, Darren,” Ambrosia said with a smile. “It was nice to listen to. It made a good point, too. I can’t think of many non-pony mammals with bright colors outside of a tiger… though that’s not too far off from brown or a dull red, is it?” She chuckled. “I’m glad we got you for a Gentleman.”

“Mm. Did you study animals in school?” Ribbon asked.

“Eh, I’m just a biology graduate who got lucky and got an invitation to Equestria. It’s… actually, I’ll be honest, I’m still a bit boggled by how brightly colored you ponies are. I’m not complaining, it’s just…”

“Jarring?” Ribbon suggested.

“Very. I guess the pegasi take off the shock a bit, since they have wings. Just go to the rainforests of Earth sometime and you’ll see some of the most brightly colored birds in the world.”

Pizzelle lifted her white colored wings, and snorted. “Kinda got ripped off in that department, huh? White coat and wings and a blonde mane.”

“Oh, dear, don’t talk down about yourself like that,” Ribbon said. “I’d love to have your figure, and you have a gorgeous mane. I just wish you’d let it hang down once in a while instead of keeping it in that tight bun all the time.”

Pizzelle gave a grunt, but said nothing.

“No, I think she’s right, Pizzelle,” I added. “I mean, so what if you’re not brightly colored? You’ve got wings, and you’re a damn Wonderbolt. That’s more than most ponies can say about themselves, even among pegasi.”

Pizzelle smirked a little. “Thanks.”

Ambrosia looked up at a clock hanging from a post and sighed. “I’m afraid I have to get going soon. I’m traveling to Manehatten to see my brother and sister-in-law for about a week or so.” She gave me a small, sympathetic smile. “Once I get back, we’ll be spending a few days just the two of us, so I can catch up with Ribbon and Pizzelle on a few things that you’ll need to know about earth ponies.”

“I’ll make sure Ribbon doesn’t hogtie him to her bed with rope while you’re away,” Pizzelle joked, earning a overly dramatic gasp from Ribbon.

“I guess I’ll leave him in your capable hooves, then,” Ambrosia laughed. “Take care, girls. Bye, Darren!”

“Safe travels,” I said, waving goodbye as she headed down the road.

As soon as Ambrosia was gone, Ribbon turned to Pizzelle. “Honestly, Pizzelle? Rope?” She let out a snort. “I’d at least use something softer, like velvet or silk. No need to cause any rope burns.”

Pizzelle looked to me and gestured to the unicorn with a hoof. “This is what you have to look forward to for two months, Darren. Hope you’re ready.”

I just chuckled, still finding myself looking forward to what lay ahead.

Eventually it was time for Pizzelle and Ribbon to depart, but not before leaving me some ‘homework’. Seeing as I had a lovely marefriend, Ribbon and Pizzelle saw it fit for me to practice brushing with her.

Full Bloom, unsurprisingly, loved the pampering.

“Mmm…” said unicorn hummed as I ran a hairbrush through her mane. The two of us were currently sitting on the large recliner in my humble abode, Full Bloom lying comfortably across my lap. “Darren, can we do this more often? I’ve never had a stallion brush me before.”

I replied with a gentle nip to her ear, earning a gasp from her. “I’d love to. It’s relaxing, actually.”

“Really?” Full Bloom tilted her neck to the side, a silent request for me to start tending there. I set down the hairbrush and switched over to a soft bristle brush, taking only a moment to figure out which one was which.

“Yeah, I really do enjoy it,” I said as I ran the soft brush along her neck, earning a contented exhale from Full Bloom. “I’m helping you, and bringing out the best in your coat and mane… not to mention you seem to be enjoying this, am I right?”

“It is soothing. You said you learned how to do this from your teachers after only a few hours of talking to them?” She asked me, a hint of amusement in her tone.

“Yep,” I paused as I noticed a stubborn snarl of hair in Full Bloom’s mane, and quickly switched back to her mane brush. “Hold on, I missed a knot. I’ll see if I can get it.”

“Oh, sure,” Full Bloom tilted her head for me. “That’s neat, though. I didn’t think they’d teach you stuff like that.”

“It’s just basics. Believe it or not, I have some notes in my folder on brushing tips.” I kneaded the knot with the brush, letting out a satisfied grunt as I loosened it. “There, that’s gone.”

Full Bloom’s hair was naturally curly, so it had been a delicate job working on her mane and tail. She had been patient with me, though, and offered her own advice on working with the brushes. She even kept the wincing and painful grunts to a minimum when I had first gotten started, all while patiently giving me tips on how to work with her mane. With any luck, I’d be at least halfway decent with the comb and brush techniques before I was a full-fledged Gentleman.

“So, I was reading up on that big concert in Fillydelphia,” I began conversationally. “Never knew there was any real hard rock bands in Equestria.”

“Hm?” Full Bloom looked back to me, then smiled. “Oh, yeah, I heard about that. They’re called… uh… I can’t remember their name, but they’re that one band with the female griffon singer, right?”

“I think they call themselves Nimbus Wake or something, but yeah, Pizzelle told me they’re pretty heavy as far as Equestrian or Aeric music goes.”

She turned to look up at me, tilting her head a tad to the side and giving me a curious look. “What about them?”

I shrugged. “Just thought it was cool that this world has so many similarities to Earth. It’s kind of scary, actually.”

Full Bloom hummed in thought. “You want to go to the concert?”

I shook my head. “I don’t think I have nearly enough bits saved up for a concert that’s going to sell like hotcakes once the tickets are on sale. They’re a pretty big name in the music industry, right?”

“Eh,” Full Bloom waved a hoof. “I could set us up with some tickets, I bet.”

“Let me guess,” I began, smirking a little as I resumed brushing her, now using the soft brush on her back. “You got a friend who can hook you up with some tickets, right?”

She gave me a playful smile. “A lady can’t reveal all her secrets, Darren.”

I clucked my tongue and ran a hand along her neck, earning a pleased sigh from her. “Fine, fine, keep your secrets from me. It just makes you all the more appealing, anyway.”

She lifted her head up and gave me a peck on the cheek. “That’s my intention, Darren.”

After I finished brushing her, she slid off my lap and dug into her saddlebag that she had brought over. “I know you’re not big on these sorts of things, but I figured I’d bring over a little something to celebrate your new job.” I watched as she pulled out an object wrapped in paper, floating it over to me and placing it in my lap.

I looked to her, and she simply nodded to the present, giving me a nod.

I opened it, only to gasp. “Full Bloom… how did…?”

“There’s a store down the road that sells jewelry and stuff like that. I saw it on display, and figured you might like it.” She gave me a smile. “It was crafted by a minotaur jeweler.”

It was a watch. To be more precise, it was a watch that seemed more appropriate on the wrist of some big CEO or tycoon of some sort than in my hands. There was a transparent clock face with stylized numbers encircling the face. In the upper right corner there was a smaller subdial that showed the day’s date, and another subdial on the lower left that indicated—if the crescent moon were any indication—the current movement of the moon and sun. I don’t know what kind of metal the watch itself was made of, but it had a silver color and weighed a bit more than any watch I’ve ever owned in the past.

“It’s called a Mynos IV Ortus. The entire band and case are made from platinum, which I hear is pretty rare in the minotaur lands. The hands are made from sapphire, and the numbers are made from gold. I was told there are only fifty watches like that in Equestria, and two hundred throughout all of Tellus. Don’t worry about it breaking or getting damaged by water, either; the store owner told me it has a strong durability and water seal enchantment that will last for at least forty years. That little subdial with the sun and moon is actually enchanted to adjust with the celestial bodies, so it will change if you flew over to the other side of Tellus.”

I placed the watch back in its case with great care. “Full Bloom…” I smiled, but shook my head. “This… I couldn’t possibly—”

She walked towards me and placed a hoof on my knee. “Take it. Please.” She gave me a gentle smile. “Just let it be a way of saying thanks for being such a wonderful friend… and a wonderful lover.”

I frowned. “We haven’t even been together for a week, Full Bloom. I really appreciate this, believe me, I do, but… this is like… an anniversary gift that middle-aged couples with lots of money should get each other after being together for twenty years.” I looked at the watch case, and sighed. “How much did this cost… if you don’t mind me asking?”

“Less than you think,” she replied, gently rubbing my knee with a hoof in a reassuring manner. “The store owner had it marked down because they were having a moving sale. It was like… fifty percent off, at least.”

That still didn’t help. There were watches that looked like this one back on Earth that easily ran into the six digit numbers when it came to price. My uncle Dale was a bit of an enthusiast when it came to expensive office decor and apparel—especially over-priced ballpoint pens—but even he drew a line on such purchases. Watches were one of those things, but he always had an appreciation for the expensive brands. I knew a thing or two about them as well, or at least could tell when something was more expensive than all of my worldly possessions combined.

“You’re going to be a Gentleman, Darren, and I want my Gentleman to be the envy of every other guy in the business. You’re going to fit the role, I already know that, but I want you to look the role as well. That way, when you’ve got some high class mare from Canterlot giving you the once over she’ll know you’re the real deal.”

I still felt guilty for accepting this present from her. It just felt wrong to take it, but she was insistent on me having it. She didn’t get upset when I said she didn’t have to spend all that money on me, instead saying that she still had plenty of money in her bank accounts to live off of comfortably. I didn’t ask how that was the case, instead giving in to her stubborn kindness and promising to take care of the watch.

“I’ll wear it when I start taking on the big name clients,” I said with a smile. After several long moments, I added, “Any idea who would be considered a 'big name'?”

She grinned. “How about just wearing it for every date and gauging their importance by how they treat you?”

That was… surprisingly meaningful, and I couldn’t help but agree.

I got up from my seat and crouched down so I was eye level with her. I pressed my lips to hers and held them there for a few moments. Full Bloom leaned into the kiss a little, her back left leg lifting ever so slightly as she did so. When I pulled away, she was breathing a little faster, and smiling giddily.

“Thank you,” I said, wrapping my arms around her. “You’re a wonderful mare, Full Bloom. I’m the luckiest guy in all of Tellus and Earth for having you for a marefriend.”

She let out a soft mewl as I planted another kiss on her neck before slowly parting. She whined in protest, but made no attempt to pull me back. Despite my desire to continue with our little session of intimacy, both of us had to be up early for work.

“I don’t know if my bed will be as enjoyable as yours. It’s not as big as yours, after all.”

She gave me a gentle bump with her hip as we made our way to my bedroom. “I think I’ll manage. We’re well past the point of needing extra space in a bed, after all.”

I chuckled and gave a nod of agreement. Full Bloom truly was an amazing mare, and not just because she bought a watch that probably would have cost a small fortune. It was the fact that she was supporting my choice to pursue this job, and trusted me. I know the social norms of Equestrians differed from my culture, but it still meant a lot that she had no problem with me being a Gentleman.

I paused at the doorframe of my bedroom, and looked to the unicorn as she hopped onto my bed. When she noticed me watching her, she grinned and raised an eyebrow. “What?”

“Just thinking about how awesome you are.” I walked into the bedroom and threw off my pants and shirt, settling under the covers in my boxers. In no time at all, Full Bloom had settled into my arms, her back pressed against my stomach. I ran my fingers gently over her barrels and planted a few soft kisses on her neck. “I wish I had met you sooner, Full Bloom.”

“Same here,” she answered with a stifled yawn.

A thought occurred to me suddenly. I wasn’t sure entirely on how the intricacies of dating in the world of ponies, but I felt a need to put this out there, if not for my conscience’s sake, then for hers. “Full Bloom?”

“Hm?” She answered, her ears flicking as she turned her head a bit.

“I… I’m still learning how this is all going to work between us, but I just want to say that… well, since I’m going to be with other clients and… probably having sex with most of them, I think it’s only fair that, if you ever want to do something similar with another pony, human, or whatever… I don’t have a problem with it.”

She tensed a little, and rolled over to face me completely. “Darren?”

“It’s only fair. I mean, there’s probably going to be times where I’m gone for a few days at a time, you know? I only want you to be happy. If… if there’s a mare, stallion, human, griffin, whatever… I just want you to know that I wouldn’t be upset if—”

“Darren, I wouldn’t—”

I pressed two fingers against her lips gently. “I understand, but I’m just saying so. Just in case you have a change of heart. You’re my special somepony… that’s the proper term, right?” She nodded. “No one is going to just take that away from you. I just wanted to make that clear, so don’t worry about anything like that.”

For a moment, I thought I might have offended her. I opened my mouth to apologize and explain, but she cut me off with a giggle and a nuzzle to my cheek. “Such a goofus.”

“Hey, I’m being genuine here. I don’t want you to suffer through periods of me being gone… especially when you’re in heat.”

She shook her head a little and planted a kiss on my cheek. “Thank you. I guess you have a point. I might find myself pining for you, but I don’t want you to think that I can’t stand a dry spell, either. I’m a big girl.” She shuffled a little closer to me, and nestled into the crook of my neck. “I appreciate it, though. If I ever find myself in that kind of situation, I’ll let you know first.”

I closed my eyes and let out a yawn. “Fair enough. Just let me know if you ever get together with one of the Wonderbolts.”

A snort of laughter was her only reply.

Satisfied with our brief talk, I adjusted my embrace around Full Bloom and felt the weight of sleep settle over me.

End of Chapter Five

Author's Note

And so begins our valiant heroes intrepid journey into the realm of Gentleman training. What lies ahead of him? Will he be up to the task? Will he survive? Only I know for certain, and I'm not talking!

A big thank you to my pre-readers Firesight, AJ Aficionado, and Demon Eyes Laharl for helping clean this up and giving helpful feedback. If you like this story so far, I'd recommend you check out their works as well, especially Demon Eyes Laharl's, considering he set up the entire base upon which the Gentleman for Mares story series is sitting upon.

Anyway, that's all for now. I'd like to hear any feedback from you wonderful readers, and until the next update, keep on keeping on! Later!