Gentlemen for Mares Tale: Upper Crust (The VIP Client on Fimfiction)

 

“Everypony is stuck up in this part of Equestria,” you say, not caring if it puts you in hot water with how high your emotions are running right now. The past few weeks have been a struggle for you as a gentleman. You were doing so well in the Whinnyapolis and Baltimare divisions as you were getting started.

 

It had been easy to score new mares every week or so. You even had the first Kirin client attained by a gentleman, earning you your call name, “Heat”. That was enough to get you notoriety as a hot shot of a gentleman. The new way that Rising Star was running this little branch of the company was on her terms, so mares needed to request you from the line up specifically, or you had to get them, haunting hotel bars and other expensive meet up spots in Canterlot.

 

“It’s not like I didn’t have mares before this whole… Canterlot debacle,” you look up, wincing at what you said. This new division of gentlemen in Canterlot was Rising Star’s baby. Anyone who’s wise wouldn't have said that out loud. Earlier, she was disappointed in you, now she is furious thanks to your indirectly insulting view of how things had been going so far in this area judging by the glare you are receiving, loathing emanating from her amber eyes. The glare turns into a snarl, making her sharply white teeth contrast with her deep purple coat and golden mane.

 

Rising Star speaks slowly, cautioning you to pick your words carefully as you go along, “This division has been having its struggles, yes. There is something to say about how we have been reaching out to a different demographic, but zero mares is zero mares, Heat.” The scolding makes you turn your head to the window on the right of you in her second story office. It overlooks Canterlot’s downtown square, ponies marching in fancy dress while they’re holding their heads high, despite the freezing mist for weather. The outside is grey from the chilling winter overcast too.

 

You think about your situation as you look away, forehead veins protruding. Hearing something you already know about your current standing in your career is starting to make the tension in the office increase. The other three gentlemen assigned to work under Rising Star were all in the same shoes before you started here. They were deemed attractive, popular, and important assets to the company. The heat in your face begins to subside a little while staring off into the distance, thinking about how it’s not so bad considering the top gentleman here only has three current clients. The other two guys only have a couple of mares that were regulars as well. What’s still frustrating is how you had to give up your old clients to make way for the potential swathes of new mares in Canterlot that would supposedly pay top dollar and order the four of you at once. Yeah, that’s not happening anytime soon.

 

You look back to your boss, feeling conflicted as she is in the same position as you in a certain way. Rising Star really showed her loyalty and grit, climbing up through the ranks of handler mares. Platinum herself had chosen her to lead this place after such a stellar performance. It’s such a disappointment that the place is struggling right now. Adding insult to injury, you’re the main offender for its lack of success as it seems.

 

You’re about to speak on how you’ll get mares as fast as possible, really putting yourself out there, but you’re cut off, “Heat, I need you to have a client soon, or we’ll need to part ways”. The seriousness of the situation is now explicit to you. Your stomach drops. This job has been such a gift to you before Canterlot. It’s just so unfair. The earth pony before you is starting to show how she climbed up the ranks so fast. She always seemed like the cut-throat type. Why not let you go back to Baltimare and lay some of the cougars again instead of just dropping you entirely? Rising should never have been given this much power as far as you’re concerned. If anything, she should be helping you get these clients like they used to do in your first stint with your original handler.

 

“Okay, I know I can get a couple of mares this week. I promise,” you reassure her. You make direct eye contact, ensuring you get what she means. The mare just continues to look at you blankly before crossing her hooves on the clear tabletop of her desk. It seems like she’s displeased at what she has to say.

 

“Heat, I’m going to be up front with you. I’m giving you until Tuesday morning to get a client,” she explains. The gears in your head make a couple of meshed revolutions at what she told you. You feel panicked as you realise the amount of time you have.

 

“It’s Sunday!” you can’t help but voice your concern loudly. What could you even do to get a mare in such short notice when there hasn’t been a single client for you in the past few weeks? Her deep purple hoof raises up for you to calm down.

 

“I’m sorry, but I was given the task to make this a permanent establishment in Canterlot. I can’t have it fail from lack of productivity, even if the others are struggling too. There’s… a threshold you must meet,” she explains to you. Your hands grip your knees and the floor is looking mighty interesting right now. It seems like it’s all going to end in a few days from now, and the seams in the carpet pattern are the only thing your senses want to take in.

 

You acknowledge her to hopefully speed this whole talk up and be free from the torturous atmosphere of Rising’s office, “I’ll try my best”. It comes out in a forced manner, mostly hiding the disgust you’re feeling. Rising is not convinced judging by her face.

 

“I hope to see results. You’re dismissed, Heat,” Rising lets you know that you can escape the dungeon that takes the form of her upstairs office in Canterlot’s Gentleman For Mares’ building.

 

It’s not hard to convince your legs to get up and move to the door of her office. Speed walking out just allows you to separate yourself from the mare that is causing you distress. It’s easy to let the hard heels of your dress shoes clack down the steps at your fast pace to get to the small lobby of the building. The main door is flung open by you on your way out whilst you pay no attention to the receptionist. It’s also easy to rush out into the cold. The weather is just warm enough to allow sleeting rain instead of snow. A few flakes are mixed with the misty atmosphere that’s already starting to become a heavier deluge. You pay no attention to it.

 

What’s hard for you is the feeling of doom dominating your mind. With the high end suit that you have on, you would fit in with the ponies who are dressed up on Canterlot’s walkways, but the lack of an umbrella seems to convey the way that you’re feeling to everypony as you pass them. You look depressed and shaken up in the rain. You are going to a location, not just moping around, so it’s giving you a little bit of drive. The other gentlemen are going to be at a bar on the edge of the city. It seems you’re going to meet them there as the unsuccessful, loser of the group.

 

There’s a puddle on the road every little bit you travel, and it’s giving the buildings on the side of the street a reflection of their purple, white, and gold masonry. Most ponies are briskly moving about and holding their heads in a comically high fashion. The prancing further makes the way you are trudging stand out. What are the odds that weather suited for Dracula’s Castle would be happening while you just got the news you are about to be fired?

 

Continuing to walk, a mare eyes you with discomfort at the haggard state you’re in. She’s yellow, wearing heavy eyeshadow, and has dollar signs for a cutie mark being half hidden under her designer saddle that has an umbrella mounted to it. You both glance at each other while walking past, making you slow down a bit and manually focus your eyes on the path ahead. You make it past her, speeding up a little from the social awkwardness that the super brief experience was.

 

“Excuse me,” the mare you just passed jolts your attention to her. You turn around. She’s turned perpendicular to the street, and her neck is turned ninety degrees toward you.

 

“Y-yes,” you get out, concerned with the way her face has one eyebrow raised.

 

“Why in Equestria are you not using an umbrella?” The pony is speaking with a mixture of curiosity and unease. You don’t really have an excuse. You choose to shrug your shoulders.

 

“I don’t know,” you say and are about to continue on your way, feeling shamed.

 

“Tsk, you humans must have a complete disregard for fashion. Getting a pinstriped suit like that all rained upon. You must take this,” the high class pony is speaking to you while her magic opens her pouch that’s attached to the saddle she’s wearing. A smaller umbrella floats out to you. She shoves it into your chest since your depression keeps your hands at your side at first. It takes you a second, but you make the metal clip unlatch for the top to spring open. The cold rain stops pelting you, and it’s quite the reprieve.

 

The mare tells you, “I’m Upper Crust, and you’re welcome.”

 

To not be ungrateful, you tell her your name too, “The name’s Heat. Thanks for the umbrella, miss.”

 

“Carry on then, and please keep your suit dry the next time it rains,” Upper Crust commands and continues about with her highfalutin strut, wherever she’s going. You watch her flanks swaying as she leaves. The motion activates some primal urges in you. You wouldn’t mind having her as one of your clients, you think. You decide to break your stare and head towards the bar again.

 

The walk is starting to feel a lot less depressing. There’s no water splattering your lapel at the moment, so it’s a small victory. There’s a lot fewer ponies out as you progress. Of course, the rain is making them stay indoors.

 

There’s finally a familiar sight of the white and purple neon sign that stands on the face of the bar. “Crystal Cascade” reads the sign. You get closer and begin to undo the umbrella so you’ll fit through the glass door entrance. The building is not different looking on the outside compared to the surrounding places. Entering, there’s a change of scenery: There’s humans in here. They’re all dressed like you to fit with the uppity environment of Canterlot.

 

It’s about the size of a normal, human restaurant or bar from back on Earth with regular tables around the right, and the main bar area is a massive U-shape of white marble with black veins. The side of the bar, along with the floor, is the inverse of the top; black with white veins. The place has several magically lit light sources making the shiny, stainless trim glint with the black, brick walls. “This is a place worthy of Canterlot,” you think as you enter. You look around for your group amongst the other patrons.

 

“Look who decided to show up!”, the other gentleman you work with for the division, Shane, signals you to come sit by him and the other two. You go up and sit on the black bar stool. Even though everything looks expensive here, the stool is just cloth. You figure that Equestrian ponies wouldn’t be skinning animals to make leather anytime soon for their seats.

 

“What’s up, guys,” you greet them. Shane pats your back as you sit down. He’s on your left.. He’s lankier and sporting dirty blond stubble on his face. Shane has two younger, government mares that he attends to on the job. You bet they must be the ones who thirst after a “bad boy” type to contrast with their line of work since Shane is covered in tattoos and can have an attitude if he wants, like when you don’t call him his real name. He hates having a call name. The other two are on your right, sitting around the marble bar too.

 

“What’s up, buddy,” goes Steele with his typical, midwestern style of saying hello to your right. You fist bump him. He’s shorter but built like Zues, if Zues had short, black hair. Steele is his call name obviously, but you think his real name, Harold, is pretty damn funny sounding sometimes.

 

On the far right, the last gentleman to greet you is Fox. He’s older with a tad bit of grey and was an escort on Earth too before the whole Equestrian dimension fiasco. He salutes you with his right hand as his left is currently holding the clear glass full of the cocktail he’s finishing off. You think you have a decent working relationship with him. He usually bangs mares that are in search of the most experienced and well known gentlemen. He’s the one who currently has the most clients here too. Fox serves as an unofficial leader to the group.

 

“Sheesh, you look like a drowned rat,” Shane notices the amount of water you have on your suit, “you need a freshen up, man”. Shane beckons the unicorn mare who runs the bar to come over. “Can you give my friend a han- hoof with his wetness problem?” The unicorn complies and uses her magic to float a towel to you from one of the drawers in her area. It hangs around your neck. “Can you get him a drink too?”. She waits for your request.

 

“Straight vodka please,” the unicorn and the other gentleman are a little perturbed by your choice. You figure the bitterness will compliment how you feel if anything, “and make it a double shot”. She trots over to where the handles and fifths of liquor are kept.

 

“How’d your meeting with Rising go, Anon?’ Shane asks. The brief moment of time you had your mind off from what happened earlier is broken. You tense up, not able to respond all that quickly.

 

“Well, I got till Tuesday, so this’ll be the last time I might hang out here,” you respond with a bluntness brought about from your nerves being shot. Everyone starts to chuckle. You don’t. There’s an uncomfortable silence.

 

Steele notices your lack of laughter, “dude, are you serious?” You simply nod your head once, looking at the hanging wine glasses that are in the bar tender area instead of someone in particular.

 

“I haven’t gotten a mare that wants me in the past while I’ve been here, so my time has run out,” you explain glumly, “Unless I somehow get a client by Tuesday morning”. You can sense the other guys are looking at each other, not sure of what to say.

 

Steele speaks first, “well, holy shit”. There isn’t much to say beyond that. You’re finally able to break your eyes from the glasses and see the others' faces. It’s a safe bet that you’ve killed the mood around here.

 

“Don’t mind me, though. We might as well have some fun tonight,” you try to lighten things. The bar mare levitates your double shot of vodka in front of you. You put a few bits on the bartop.

 

“Hey, at least you didn’t call her Five Stars like the one guy did on accident,” Shane is trying to make it not seem so bad, “she almost killed that guy with her bare hooves before she decided to fire him instead”. This grants Shane a slight smile from you.

 

Steele is next to talk, “You’ll get a client. There’s that parade tomorrow with the princesses, and everyone is gonna be there on Mane Street, you know.” You ponder that. The parade seems like an opportunity to save yourself tomorrow before Tuesday's inevitable hand of doom pulverizes you. “Take this too,” Steele gives you a card with Gentlemen For Mares emblazoned on it, “they’re just now releasing these, and they gave one to me, but you can use it to maybe score a few tomorrow”. You thank him and let the others start to change the mood back to normality with jokes and stories about how their clients treated them.

 

You and the gentleman keep conversing for a while, getting more and more intoxicated. You haven’t drank your vodka yet. Shane gets up to go to the bathroom, and Steele decides to go right behind him. It’s just you and Fox left at the bar. You glance over to him, and he raises his eyebrows at you. He gets up and sits in Steele’s seat to talk to you.

 

“Anon, we should talk about your situation,” Fox gives a serious look. Shaking your head to let him continue, he begins, “I’ve been doing this for a long time, and there’s a lot that I’ve learned. I think there’s something about you that needs to be said”. What he’s leading to is making you anxious. What’s going to come next? You stay silent in wait. “Mares and women don’t like someone who wears their heart on their sleeve like you do. Maybe it would have worked out for you better to be one of the Canterlot elites if you get what I mean. Keeping a stiff upper lip and trying to be more like them with that bit of higher class mentality.”

 

This all kind of hurts in a strange way. You’ve been operating like you did in your previous locations, and that’s what netted you some really excellent mares to be with. They appreciated how you seemed realistic and mature instead of what is expected of you according to Fox. Being a faux elitist goes against what you’re about. That was Baltimare and Whinnyapolis though. Was there truth to what he’s going on about? “Listen, you needed to change up your approach, and it should've been more like mine. It’s okay to be a little fake, alright.”

 

Fox is the guy to get advice from after all, you think. He gives you a tap on the shoulder before leaving for the bathroom too, “hey, you shot your shot, Heat. You got thrown in the mix with ponies that just don’t appreciate your style.” With that, he leaves you by yourself.

 

What Fox said makes you let go of your fantasy that you’ll somehow make it by Tuesday. You grip your vodka glass, gulping the spirit in one go. The burn feels welcoming in a way. A compliment to how tonight has gone.

 

You wake up. The night before didn’t see you do any drinking besides the single glass of vodka, so you’re not hungover, but you’re still tired. It’s hard to sleep when you’re stressed out like this. Risen from your bed allows you to meander to your bathroom. The apartment you live in is pretty darn nice. Everything in Equestria seems to be much higher quality than Earth. There’s probably some global economic policies baked into that, but that’s its own can of worms.

 

First, you take a shower, touch up some spots while shaving, and then you put on one of your suits. It’s a navy blue pinstripe style suit, but there’s no handkerchief in the pocket. You take the card off of your nightstand that Steele gave you yesterday. It slips into place in your suit pocket, sticking up just enough to show the company name. You think that looks like a good placeholder.

 

It’s determined in your mind that today you’ll go to the parade where the princesses are going to be headlining. Whether you succeed doesn’t matter. All the hustle and bustle in Canterlot will be there anyway, so you can take your mind off things.

 

Breakfast is just some cereal that you’ve got. Sapient cows made the milk for your bowl of cereal, and that’s kind of… strange. No matter, it still tastes good. You skip your morning exercises and head out the door of your Canterlot apartment, letting your suit boost your confidence.

 

Today is bright, but the winter sun is still in a whitish grey sky. The pegasi must’ve cleared everything for this parade.The cloudlessness is making the brick road radiate a tad bit of heat. That extra warmth is a blessing in the cold. New Year’s Day was only a week ago anyway.

 

You make it to Mane Street. It’s not far from your apartment, so going there is quick. There’s a lot of ponies waiting for what’s coming. Outsiders from Ponyville and Cloudsdale must be who a lot of them are as they aren’t adorning ensembles that cost a thousand bits. You’re early too, so it's not flank to flank just yet with all the bystanders.

 

Time passes, and you keep checking your watch that’s replaced your phone after being in Equestria for so long. The lack of outlets and service made it obsolete in your eyes. If you really need to be contacted an enchanted stone on your watch helps you with that by blinking.

 

It’s really close to the parade finally happening. The amount of time you’ve spent so far this Monday morning is slipping quickly. Whenever you don’t want time to move fast, that’s when it does. Crowding around you, the exorbitant amount of ponies that are accidentally bumping into you lets you realize that it should be time to watch some regal princesses make their impression soon.

 

The parade starts with the military ponies marching. Royal guards are flanked with chariots. A highlight is some of the guard mares that could buck you through a wall if they wanted with their sexy, toned legs and flank muscles. Maybe you should try to get one of them as your clients…

 

Ogling has you distracted. The first princess abruptly comes into your view. There’s no “floats”, but there are chariots like the one Princess Twilight is riding on, immaculately shiny and golden. Some ponies in the crowd feed on the nervous energy she has. She’s smiling and waiving, but you swear you can see sweat droplets on her forehead like she’s stressing over what’s going on.

 

The chariot she’s riding in hits a pothole made from the missing couple of bricks in the Canterlot street. The hiccup makes her rise off her haunches, and the chariot audibly sways with a cartoonish squeaking sound. That thing’s gonna need some WD-40 and duct tape after that. Twilight is frazzled and shakes her head like a wet dog after jumping out of a bath.

 

You put your hand on your chin, observing the scene. Come to think of it, Twilight’s awkwardness makes her pretty cool and relatable. Maybe other ponies in the crowd are disappointed with her, but you like her style. The purple princess continues out of your sight.

 

“Was that Princess Twilight?” a female voice behind you says in an accent that reminds you of working in Whinnyapolis, “tall stuff over here got in the way.” The side comment makes you roll your eyes. You stick out pretty tall compared to all the ponies out here. It’s not your fault they are a little over half your height. It must be some mare and her friends openly being catty behind you. You got here to the edge of the street from being early. Sucks to suck, ladies.

 

Cheering is erupting closer and closer. That must be Celestia herself coming your way. The tourists must be getting a serious rush of dopamine. You’re finally able to spot Celestia. She’s just a small brilliance of prismatic hair that has a white horn erect from your vantage point.

 

“Is that her!? Is that her!?”, the same group of mares behind you are excited for what’s coming.

 

“Where’s Luna?”, one of them asks. You think that she’s most likely sleeping.

 

Another says your exact thoughts, “I think she’s more of a night pony.” You roll your eyes again.

 

The princess is in full view now. She really is as regal as they say. She’s flanked by a couple of chariots, and a whole platoon of guards is surrounding her with pikes, maces, lances, and general pointy weapons you would know more about if you were born during the middle ages.

 

Celestia is riding on a chariot like Twilight. You spot the same hole in the road that the missing bricks created from earlier. The radius of armed guards probably makes it tough to notice the upcoming road hazard. Looking around, there’s no one else that’s noticing the problem you’re seeing play out in your head. There’s gonna be another awkward scene but with Celestia being thrashed about this time.

 

Celestia is still smiling and waving as she gets just before the pothole. It’s pretty clear she’s exponentially more experienced with these crowds compared to Twilight, making things less tense and more awe inspiring. The two royal guards are pulling Celestia exactly to the wrong spot to miss the hole.

 

“Clank,” goes the chariot. You close one eye, wincing, knowing this was going to happen. Celestia’s golden regalia she’s wearing on her hoof slips off as she attempts to steady herself. It bounces off into the gutter of the street. The princess notices, and looks around, unable to find where it went amongst such a crowd of bystanders and guards, but you see exactly where it landed. It’s in the gutter… right in front of you. The chariot keeps moving, making her shake her head in distaste that she lost her horseshoe.

 

Believing that some tourist might try to pawn the thing on the pony black market for all you know, you think you should do something. There’s a break in the guards walking down the street, leaving you an opening. Acting quickly, you step past the sidewalk and grab the thing from the street.

 

“Hey, buddy, that’s the princesses’,” one of the catty mares from Whinnyapolis calls out, seeing you pick up the weighty, gold shoe studded with a few diamonds. You turn to the crowd, who’s looking at you with contempt, and being that there’s a few hundred eyes on you now, the stress hormones in your body tell you it’s time to go.

 

You break off into a run and try to catch up with the princess. The dress shoes you have on make a clopping sound not far off from a pony while you run. Catching up, you make it to the back side of the guard on the five o’clock position of Celestia’s chariot.

 

“Princess Celestia,” you try to be audible while not startling her to avoid a spear being aimed at your neck. Your hand extends out the shoe, even though she’s fifteen feet away. All the guards halt. Metallic pinging sounds of their weaponry being aimed at your body are heard. The guard you’re closest to you aims his pike directly at your gut, threatening to spill your innards if you go nearer. This isn’t good.

 

The crowd on both sides of you gasps. It can’t be too often they see a pony or human about to be slaughtered in front of them. Your eyes are able to catch the intense glares of guards that are ready for combat. To your relief, a golden aura envelops the weapons around you and tugs them upward. The guards comply. Now that you’re looking up, you can see Celestia inspecting you after her chariot has stopped. Everypony seems a little calmer. You’re still frozen in place, extending your arm outward.

 

Her magic floats the shoe from your hand, and it slips the piece of regalia back on her hoof. Her eyes are closed in concentration and satisfaction while she does. Opening her eyes again, Celestia looks you up and down slowly, appreciatively.

 

“Thank you, my human subject,” she says in her velvet smooth voice. You smile. The guard that was just aiming his pike at your guts harrumphs and turns back to marching.

 

It’s Tuesday morning. The time has finally come to let Rising Star do away with you and your career. You’re sitting in the small lobby of the Gentlemen for Mare’s building. The secretary is not in yet, so at least you won’t have to take the walk of shame out of the building in front of her as you leave. Yesterday’s actions play out in your head a few times. It was pretty absurd that you went from helping the princess via circumstance to now being fired.

 

“Heat can you please come to my office,” Rising Star calls you from the top of the steps. You look up at her. She doesn't seem to have contempt or any type of malice in her eyes, but with how she’s been, you question her motives. You try to remind yourself that this isn’t a personal thing. Trudging up the stairs she turns away and opens her office door to let this awfulness begin. There’s probably paperwork that you need to do on top of this miserable experience. As you go up the steps, you hear the main door open behind you. The whimsical sound of magic is happening which tells you a unicorn opened it. It seems that must be the secretary. You make it to her office at the top.

 

“Please have a seat,” your boss extends her hoof out like she’s being a saint. She closes the door behind you. Your mood is indifferent and depressive, having played this out in your head so many times. “As you know, things haven’t been working out so far, Heat,” she explains the obvious as she sits on her office chair, the desk separating the two of you. “I brought you in to start on the severance-”

 

-Knock, knock, knock-

 

The thwacking sound at the door is starling. Both of you look towards the entrance to the office. “We’re busy in here, Miss,” Rising assumes that it’s the secretary trying to tell her something based on the tone she has.

 

“Is Heat in there with you? This is important, I promise,” a familiar voice responds from outside. That definitely was not the secretary who knocked on the door just a minute ago. Rising looks back to you briefly, probably wondering what this could be about too.

 

“...come in then,” Rising grants them access. The door opens and what is on the other side shocks the two of you. It’s Platinum Corona, wearing a variation of her incognito choice of fashion: It’s a full latex suit which is covering her body with gasmask-esque goggles where her eyes are. It covers her every inch besides her horn and the unzipped portion around her mouth to speak. Her presence is a little imposing being in tandem with her pony gimp suit, especially in this current situation of being fired. To you, the uncertainty of what this means is making your stomach drop even more. Platinum Corona is the main mare for this company, though. Is she here to rub salt in the wound of your failings as a gentleman?

 

Through the door, some papers are levitated as she enters the office. You try to inspect them from your seat. Platinum is floating two contracts in her magic. You’ve seen the typical writings in Baltimare so many times, you recognized them from across the room. The yellowed parchments are floated to the see-through desk.

 

“Good morning, Rising,” Platinum begins. “Heat,” she acknowledges you with a nod, “ apologies for the interruption, but I want to ensure that this gentleman is well prepared for his contract.” Platinum explains this as the muzzle of her suit undulates with each word. Rising inspects the first contract, her eyes reading left to right. It all seems normal to her.

 

“Hmmph,” Rising muses to herself at the first one. She places it down toward her left. You can just barely make out the name “Upper Crust” on the signature area. You remember the yellow mare from the weekend. How did she know you were a gentleman? Well, that’s a stroke of luck since her flanks alone are a total knockout.

 

Rising picks up the next one. Her eyes scan it the same way. They go left to right, but they suddenly stop and backtrack. She blinks a few times to ensure she’s seeing what she sees. Pausing on the supposed outlier in the contract, your boss drops the paper and looks up at you slowly, mouth now agape. It’s a strange expression, like a mixture of disgust and shock directed toward you. Platinum interjects again.

 

“If you’d please allow me, I’d like to take Heat with me to give him some advice after you review these with him,” Platinum informs Rising, but she stays silent, unblinking. You try to get a look at the paper to read the name on the second contract. You can just barely make out a couple of letters. There’s no way it says what you think it says… “Princess”?

 

Rising ordered the chariot delivery that you’re currently riding in, but it’s just you alone. You honestly miss your old handler. However, the excitement for tonight has you feeling like a kid waiting for Christmas. The time has come for your first contract with a mare in Canterlot. It’s a complete and total one eighty in terms of mood from the way that the week has gone earlier. You’re finally feeling good because of it. You still can’t believe that you got not one but two contracts, and one of them is a princess for crying out loud! It was satisfying to see Rising become stupefied at your abrupt success too. You can’t wait to tell the guys you work with about all this happening.

 

All that said, you revert back to what’s currently happening for your current contract. It’s so much fun to feel the positive anxiety of what a client’s personality might be like, what her passions are, and how she’ll treat you in bed. You’ve always fancied yourself as a connoisseur of mares in general. Upper Crust is a middle aged mare, has money, and doesn’t have foals. This should play out to be a unique experience compared to others, even though you’ve had your fair share of milfs and mature mares to please.

 

Progressing closer, the streets pass below in the chilly air. This new suit has good insulation, luckily. These Equestrian fashion designers like Rarity, who’s also a mare that bangs gentlemen, somehow blended form and function quite well. This new pinstriped suit you’ve bought for the occasion was what you picked up from the Canterlot Boutique earlier. It’s easier to spend money when you’ve not the fear of being fired.

 

The chariot being pulled by the two pegasi stallions lands you in front of a compellingly large and fancy townhouse. This is the downtown area of Canterlot, not far from the Princess's Castle, so there aren’t any mansions here as there isn't room for them. That doesn’t stop the property from being 3 stories tall and a probable 5000 square feet.

 

“G’day,” the stallions salute you as you step out onto the curb. You wave at them. Looking back to the townhouse, the white masonry of the expensive property has bricks that are glossy on the corners for trim on the front of the house, and there’s matte ones that make up the inner portion of the front face while a few deep purple ones are scattered around in the mix. You approach the double front door. One side of it opens slowly and Upper Crust is revealed to have been waiting for you right at the door, signalling she must be excited like you are.

 

Her sultry makeup is adorning her. She’s wearing a pearl necklace and nothing else, revealing all of her perfect mare body. It stops you in your tracks.

 

“Hello, handsome,” she blinks a few times seductively, making the alluring sex appeal of herself even more tantalizing. The blue-green eyeshadow she’s wearing can make you melt, you think. Coming close to her, you bend down, taking her forehoof in your hand.

 

Remembering to spark a bit more sexuality in the situation, you address the mare that has given you your first Canterlot contract, “It’s wonderful to meet you again, Miss”, and you gently kiss just above her hoof. The soft fur is starkly different to the cold air on your lips.

 

She signals you to enter, “Please take off your shoes, and come to the living room.” You follow her into the manor-like abode.

 

You take in the interior of the house first, and it’s grand alright. There’s crown molding, a fancy, tiled ceiling that’s way farther above your head than any pony could need, and the white theme is continued but with powder blue as the accenting color in a few areas. A staircase is to your left, breaking up the lobby-like entrance to the house. Upper Crust has gone to the right, where a huge, open-concept living room is located. While removing your shoes, you notice that there’s a bone white piano as the centerpiece to the living room on a blue rug. It’s next to the fireplace that is blazing, lighting up the whole space. You can feel warmth radiating all the way from where you’re at. You approach the couch where Upper Crust has decided to lay on her side in an enticing fashion. Her legs are sprawled out in back, and she beckons you with her front hoof to sit next to her. You comply by seating yourself, being careful to avoid the prestigious coffee table that has two glasses of red wine awaiting the two of you. The luxuriously sexy mare is blinking rapidly at you, accentuating the mood.

 

You’re not sure what to say, and you haven’t said much of anything yet at all actually. This mare just has you going with the flow in a natural way. You keep eye contact with her. She sits up, ready to say something. Her face is about a foot away from yours and you can smell her perfume that’s a perfect scent which isn’t overpowering. The situation is already giving off that positive anxiety of getting some, although you’ve been in each other’s presence for a very short period of time.

 

“Excuse me,... I'm going fast already, I know. I typically like to wine and dine a stallion in a highly reviewed restaurant, or I take them to an expensive game of professional croquet when I’m on a date,” Upper Crust explains to you in her transatlantic accent, clicking her tongue at the self-aware admission, “but I figured you don’t really need a bunch of fluff. Not because you’re a human or a gentleman though”. You consider this for a moment. It’s hard to parse exactly what she means.

 

“That’s okay,” you start, “but I’m not sure what you mean, and if you don’t mind, please humor me. How did you find out I was a gentleman?” Upper Crust seems to be amused by this, like she was expecting this response.

 

“I noticed you were a little odd,” is what she retorts with. It makes you recoil internally. Perhaps that’s what she playfully wants. “You seemed like you didn’t mesh with this area. However, you don’t seem devoid of class. I couldn’t quite place what type of pony, err what kind of human you were.” You raise an eyebrow out of interest for her to continue. She looks toward her wine glass on the table while smiling from being buzzed and having fun being personal with you. “Maybe I like a type of colt that is more elusive. I enjoy hunting somepony exotic. Somepony deeper cut, even if that means I have to pry them open, ahem, metaphorically.” Upper Crust seems to certainly have a type based on the response she’s given. “Also, I’m tired of needing to use money and my name to impress these money chasing boytoys. I think you check those boxes.”

 

So, Upper Crust thinks you are a hard to find type of guy? She also likes that you aren’t fake. Maybe that day in the rain was what sold that by wearing your emotions pretty obviously. That doesn’t explain how she found out how you were a gentleman. You raise your hand to ask but are cut off.

 

The mare begins, looking lightheartedly smug, “Well, I found out you were a gentleman at the parade. You had many eyes on you, you know? Luckily the rough-and-tumble ponies in the guard didn’t harm you. Returning that royal horseshoe allowed you to pass my personal litmus test for being somepony… respectable, hmm.” This admission gives you insight. You forgot about the card in your pocket during the parade, and that must explain the Celestia contract you have coming up too. That one sounds so daunting yet rewarding.

 

“That explains a lot, actually,” you admit your understanding. Upper Crust takes your hand in her forhooves. They feel wonderful. You like every part of the mare anyway. The wine glass she has on the coffee table is floated with her magical aura, and she greedily finishes off the rest of the wine in a sizable gulp before returning it.

 

“You must tell me more about yourself, though, Heat,” the unicorn presses herself against you while giving you bedroom eyes, pleading to explain more of your background. The body heat sends endorphins swimming in your brain. You feel comfortable about sharing with her. Upper Crust is very good so far at making you feel comfortable. It seems she’s really experienced with this sort of thing. The forehoof stroking your arm and hand slowly is soothing while you tell her about your past. There’s so many details that are hard to forget.

 

Starting with your home life, you explain many of the ways your worlds are so different, yet so similar, and you go off on a few tangents explaining all leading up to what made you finally bite the bullet to come into Equestria through the portal. You are a little resistant, but you trudge through the details of what has happened with the Canterlot division of Gentleman for Mares. Her understanding about how you feel about what’s happened in your life in general, makes her feel like some sort of therapist, listening to what makes you tick and what has led you on this path in life. You feel somewhat exasperated explaining all of this and lean over to take a drink of wine.

 

“You are quite the exotic specimen, my dear,” Upper Crust is cooing. She stops stroking your arm. “A human like you makes my husband look boring.” You choke a little on your drink of wine. Luckily, you are able to avoid doing a spit-take.

 

“You got a husband?” is the blunt question that you blurt out after swallowing. The mare stiffens just so, obviously not taking pleasure in the culture shock you just projected. It just so happens to dawn on you again that the ponies here aren’t always into a monogamous relationship. You start to remember how many times you’ve been told about herds and polygamy.

 

“Yes, he’s away on business at the moment,” Upper informs you.

 

“Oh, err, yeah, I-I mean,” it’s hard to get a coherent response with how you’ve lost your smoothness in this interaction. Finding your social rhythm again, you adjust to it, “Sorry, it’s just one of those human versus pony differences, you know?” Upper Crusts smiles and silently laughs with her belly.

 

“I assure you, me hiring you won’t cause a relationship problem,” she offers reassurance. You’ve set down your glass and are looking at the mare, staring deeply into her eyes, accentuated by her teal eye shadow.

 

You start on about what you think of her, wanting to put the polygamy thing aside, “Excuse me for not having a segway, but I can’t stop thinking that you’re such a beautiful mare.” She raises her eyebrows, intaking what you said. “You’re mature and so warm to be around. I didn't realize you had been able to make me ramble so much and outpour my past like that until I already had.” You are being honest at the coziness of her so far.

 

“Thank you, Heat,” she says, “you might say that I’ve been taught a lot about being a better mare from my encounters with Rarity.” She begins to close in on you, minimizing the small distance you have on the couch. She stands while doing so, making her hooves depress the cushioning beneath her. The yellow cougar wraps her forelegs around your neck, putting her face inches from yours. “Observe what else I can show you.”

 

Upper Crust tightens her hooves around your neck. She closes her eyes and kisses you. The first thing that you take in is the perfect softness of her pony mouth on yours. The wine has clearly broken down her inhibitions as she breathes hotly onto your face. You savor the feeling of her warm exhalations. Your eyes are still open, observing the mare passionately kiss you. She breaks away, and you look at each other. There’s a tremendous amount of heat radiating from your faces. She’s outshining you so far. It shouldn’t be some absurd competition, but you feel, as a professional, that you should be able to take her by surprise and be the fantastic romantic that your job implies you to be. You start to defend your pride,

 

“I can show you a thing or two as well.” Taking control of the situation, you bring her to yourself this time, but you go for her neck, just beside the back of her jaw. You lick from her neck up to her ear on her right while you rub behind her ear on the left. Having a much younger man touching upon her erogenous zones is clearly thrilling to her. A strategic idea to usurp her for being an exceptional lover goes through your mind. Now that you’ve licked and kissed the cute pony ears atop her head, you go to her horn for a smooth lick that mostly covers the base. You can feel the spiral of it on your tongue. Upper Crust looks up at you in astonishment, dumbfounded that a stallion would consider doing something so dirty. Her knees very briefly buckle. You take pleasure in stimulating her in such a way.

 

“Oh my, you hunk,” Upper softly says aloud, sounding more like an inner monologue she couldn’t keep contained rather than something she wants you to hear. You go in to kiss her conventionally. She pushes herself on you more as you kiss again. She hums a little, and her tongue starts to enter your mouth. The best thing about these pony tongues is that they’re perfect for kissing. Super softness combined with warmth and strength. There hasn’t been a mare that you’ve kissed who you’ve been able to beat in a tongue wrestling match. They’re just stronger...

 

You begin leaning back while her tongue keeps licking inside you. She moans louder as you lay back as far as you can on the couch, letting the armrest of it support your head. You run your hand along her back and neck, pulling her into you. Crust begins sucking on your lower lip. She licks the side of your neck after. One of your hands squeezes her flank, as if attempting to feel for her cutie mark. That perfect ass you observed several days ago is finally yours to caress. She squeals out and looks at your hands.

 

“Buck! You humans and your hands,” she growls in lust at your touch. Craning her neck to see you copping a feel. She starts to lose herself in the massage. You look around at her underside as you rub her atop you. You can just make out the trail of her arousal leaking out down her leg due to the fireplace’s glow making it glint. Her teats are able to be seen behind her cute belly. Just then her magic puts a stop to your actions, and it pins your hands onto the couch.

 

Between angrily horny breathing, Upper Crust is able to translate what she wants, “Heat, you’re cheating! I want to savor this, and you’re not making it easy to control myself.” The mare genuinely sounds like she’s scolding you for making her almost get to a climax in such a short amount of time.

 

“All is fair in love and war,” you say and twist yourself to be on top of her. The mare squeaks out in surprise with your hands rotating her softly but in a startling way. You have her on her back with the pillows behind her head for support on the couch while both of her legs hang off the cushion just barely. You stand up to get in position while your hands further pleasure her. Upper Crust moans out at your actions from rubbing her soft mare tummy. One hand works lower to get to her teats. The magical field of her horn glows, and she starts undressing you.

 

“This suit is quite delightful,” Crust compliments your top attire one last time before tossing it on the other side of the couch, “but it needs to be gone for now.”. Your pants and belt remain. She eyes you with a serious look that could melt metal. The belt you’re wearing comes off from your own doing, and she helps with the rest. The pants and underwear you are wearing both come down at the same time with a magical whooshing.

 

Upper Crust bites her lower lip before a forehoof comes to her cheek in giddy anticipation after seeing your dick spring free. With one hand still on her tummy, you position yourself to enter her. The mare watches you guide yourself to her marehood. You keep it passionate, still rubbing the super supple area around her belly button. Adding to all this, the smell of horny mare is intoxicating with her pheromones attacking you whilst preparing to penetrate.

 

The head you’re aiming makes contact and your dick throbs with excitement. Her mouth is agape as you push forward. The pussy lips stretch out to accommodate you. You gasp trying to control yourself as you feel the heat of her insides caressing you. Upper Crust’s clitoris winks on your dick, and it grinds itself on your shaft.

 

“Fuck,” you call out from the sensation. She giggles watching you in such pleasure too. You keep pushing very slowly forward. Both of you moan as you keep going deeper. Upper’s legs wrap around your waist as you get balls deep inside her in your initial, slow thrust. The finality of your penis stretching out her tunnel is the feeling of her cervix being pushed by the head of your cock. The two of you audibly react again. Upper Crust growls.

 

“Rut me!” she commands as you pull back. You are happy to comply by leaning over her to get more into a mating press position. Your thrusts are faster but stay sensual as you have more of your body weight in them. You savor the feeling of being one with this mare.

 

“Oh, ah!”, she moans every so often. Harkening back to what your Kirin client lost it over, you put your upper body’s weight on one hand that's on the couch. The other hand goes down to her navel, right above her vulva. Your thumb presses down firmly where you think her spot is located. This is rewarded by a cacophony of sexual exclamations by Upper Crust. Her g-spot is successfully being sandwiched by your thumb and your dick, pressing down and bringing her closer to cumming.

 

You greedily begin humping her faster. The couch starts to move a little as you rock your body into her with more passion. Upper’s thighs and legs try to not let you escape from her pussy each time you pull back. Her forehooves are pressing into your chest as you fuck. Each time you thrust, you can feel the pressure building deep in your loins to cum inside her.

 

Before you can get to the point of attempting to hold off your own orgasm, the mare you’re pleasuring starts to shake. You notice that her eyes are rolled up to the top of her head. She moans louder than before, but her lower body shaking makes her voice rattle. “I’m, I’m - OOOOooOOooOOoOooOoOooo.” Her sentence announcing her impending orgasm is interrupted and shaken up by the full body contractions that she’s having. You feel your dick get wetter with her cumming on you. Pride briefly overtakes the feeling you have for raw, carnal desire. Crust holds onto you the best she can.

 

This is the best part of the job, not money, not prestige of any form, instead it’s knowing that you can rock a mare’s world. You can put them into a realm of ecstasy and lust, but it’s all to genuinely give a piece of your romance and heart to them. The end, which is satisfaction and fulfillment, justifies the means of penetration and taboo that is inherent in this inter-species fornication.

 

The elite mare under you seems to regain most of her composure. She wants her prize. The mare’s magic presses on your head frantically to bring you closer. She kisses you before making a demand, “Cum in me, colt. Cum in me with your big, human dick!” Crust’s dirty talk compels you to be more brutish compared to your gentlemanly ways up to this point.

 

Both of her ankles are clasped by your hands, driven by galvanized sexual fury. You buck into her, letting the niceties from earlier slip. The goal is simple: put your soul into this mare. The familiar sensation has you starting to focus on going as deep as you can. It’s happening. You feel your dick twitching extra hard inside her, you can’t hold back.

 

You make several thrusts that coincide with your orgasm’s pulse. Each rope of semen inside Upper Crust’s pussy is as deep as you can go inside her, coating her cervix with warm fluid. You call her name out. It’s so intense and fulfilling to know you can do this with a creature as beautiful and soulful as her. She coos up at you while you grunt and groan from cumming.

 

“It’s so warmmm,” she trails off. Her sight is fixated at your abdomen flexing and pressing into her. “Good boy, Heat.” The positive reinforcement is what you need to make this session a reaffirmed success in your head. She strokes your chest, pawing at it.

 

You collapse on top of her. You feel your cock softening inside. You and Upper Crust respire heavily, cuddling with each other on the couch for several minutes.

 

She suggests what you can do for the night, “We should get cleaned up, Hun.” You agree and get off of her. “Maybe we can shower and have a bit of fun upstairs.” She’s about to talk more, but you cut her off and kiss her, full tongue. After breaking away, you hold her shoulders to punctuate your sensuality.

 

“You’re amazing,” you feel like a new man complimenting her, “I’m at your command.”

 

“Well, the feeling is mutual, Heat,” she concurs. It dawns on you that you might’ve just helped each other out in the same manner. She was probably lonely, not having her husband around, and you filled that void for the time being. Meanwhile, the self doubt and conflict you felt this week has washed away, and you’ve got much more than a modicum of confidence back. This is like a fresh start for your emotions.

 

You follow her upstairs to the master bed and bath, ready to be the stud needed to keep each other flying high.