Risky Business

by Simply_Z

Rating: mature
Tags: Romance, Comedy, Human
Length: 5534

[Second Person] [Butt Obsession] [One-sided Crush] Life was slowly starting to get better. You had a good paying job. You had a roof over your head. Full belly. It was all so good, until Twilight fell in love with you & screwed everything up.

[Second Person] [Butt Obsession] [One-sided Crush]
Life was slowly starting to get better. It was almost Hearts and Hooves Day. You had a good paying job. You had a roof over your head. Full belly.
If only you didn’t take that one request.
Everything would be different.
It was all so good, until Twilight fell in love with you & screwed everything up.

Published 1970-01-01 00:00:00 UTC
Last updated 2015-02-17 05:20:02 UTC

Tradesman X Request

“Look it won’t look to bad on your resume for taking in one request.”

“I said no, I have a full schedule and I don’t need more work on my plate.”

It’s dark. It’s dark, and you feel horribly cramped. You think your friend’s beak being just inches away from you face. Pieces of his lunch still clung to his feathers.

It wouldn’t be so bad if you could move, just a little bit, but you’re stuck. You’ve been stuck like this for at least five minutes now. You remember back in the day how it all happened, how this all started. The night you turned off your popup blocker. Then going to the one special site of yours that if anyone saw they would start giving you weird side glances.

Now you’re here.

You were a hit though when you first were discovered on equestrian soil. Talk shows, photos with royalty, party invites to all of the best Canterlot parties. A real human! Alas, no matter big of a splash you made, eventually, no one gave a shit.

It wouldn’t be so bad if he just asked one time, but this was becoming a bad habit. You knew you had to get your work done for the day. Today was your last day to handle the office and dole out requests to all your co-workers. Starting tomorrow you will be on requests for the next nine months until it was your turn again.

“You know I’m getting tired of covering for you Squeaks, don’t you have griffon pride or something like that?” you said.

You didn’t like taking on other ponies requests. Tomorrow was Hearts and Hooves day. You had plans, not romantic one but if you played your cards right the possibly was there.

“I know but you will like this request. It’s from some rich guy; the pay is pretty sweet too. C’mon man please this will be—“

“The last time, you say that every day. I’m not giving up my Hearts and Hooves day just for you to go sit at home to play some drinking games with some barley legal ponies. I already took your request for tonight so be thankful.”

You were tired of coving for him.

“I know, but please man. You have no idea how close I am with these three.” Squeaks defended himself weakly. “Please man, just do me this one solid and I swear you don’t regret it.”

Your eye twitched as you wiped some of the food that flaked off his fur and onto your black suit coat. “Step back, you’re getting me dirty. You know I need to be presentable for the client. The client, I might add that was yours, Squeaks.”

His eyes went half lidded as a sly smirk work its way to his cheeks. “You know I have something that you desperately want.”

You raise a brow slightly curious to be your co-worker had to offer. It would need to be something beyond words to tempt you. After pushing him out of your comfort zone and rest your hand on the wooden counter.

“Oh really, what do you have to offer.” You said.

He whipped his wing to the side and drifted it over the counter, he retracted it and there was a small yellow parchment.  Even though it was crumpled it was easily distinguishable. It was a request form. You had processed hundreds of these guys in the past month alone. “I will be in charge of the office on Monday. You know what that means don’t you.”

You could feel the hairs on the back of your neck grow. You could see just two letters on the back part of the paper. It felt like several icy daggers were floating just above your back, each ready to tear deep into your skin.

“Yes,” Squeaks continued, “I choose who does what assignments. If you do me this favor I will not only let you have prime pick off all the juicy requests. I will specifically hold all assignments from a certain little mare—“

You cut him off as if in a blink of an eye you unfolded the paper. It only took a moment for your blood to turn to ice, your eyes now the size of pins as they glazed over the client’s signature.

It read ‘Fluttershy’.

You folded the piece of paper back and made a quick surveillance of the room making sure that the room was completely clear of prying ears. You’re not sure what to think about that.

“How long have you known?” you whispered. It was your darkest secret. You had never told anyone of the lingering feelings for the butter coated mare. The way she walked with that sly sway in her hips. Her overly kind nature - sweet and innocent and pure to the world. Not to mention at sweet, round, soft looking ass. You always had a thing for butts, big, round, soft and squishy.

 It however was a one-sided affection.  You always did enjoy the rare moments you got to spend alone with her. Or when all of her friends where gathered around becoming the most influential cock-block.

Seriously, one was a dam princess.

Fluttershy was perfect. Well... maybe that wasn’t quite the right wording. She seemed perfect, too perfect, like a hand stitched doll, tailored for just one purposed.

 “About three months or so I say.” He said as he furled his wings against his sides. “It was when we got a request from her for two assistants. You never accepted jobs with two assistants. This time you did, which was odd because we both know what that usually means. Then when we got there instead of doing our normal job, we spent fifteen hours moving animal dung.”

“That doesn’t mean anything, you know I like a job well done.” You said in a shallow voice and slightly scornful voice.

“No pony, griffon or human for that matter smiles that much while picking up animal dung. You also looked like you were given a gift from Celestia herself when she gave us lemonade. Then for the next week you kept going back every day making sure that everything was a job well done.”

While you’re aware of the potential awkwardness of being caught, there was nothing to shameful for being smitten. It was perfectly understandable, given the circumstances.

He smirks at you, his left brow rising ever so slightly as he bumped your side, “do we have a deal?” A faint shiver runs down your spine.

Something in the back of your mind told you to say no. Something felt off, maybe if was a sixth scent or divine intervention trying to help you. You didn’t listen.

“Fine, but make sure the boss doesn’t find out. You know how she gets when the office plays favorites.” You said almost in a single, quiet breath.

“No pony will ever know—“

BING-BONG-DING-DONG

Both you and your associate looked at the clock at the same time. It was already five o’clock which meant quitting time. A long sigh left your lips, which also meant your real job was about to start.

“I will see you on Monday,” you say. You had said but you partner in crime was already flying out the door. Leaving you standing there alone to lock up the building by yourself. “You could have helped me clean up, you ass!” you shouted to no one.

You start to package the left over paper from the say and placed all of the requests in the ‘IN’ tray. Taking a moment to pick up a few discarded pieces of paper that had found their way to the floor you decided that it would be clean enough. Not like it was a very active business.

You shut and lock the front glass door. Taking a moment to look around for anything that might be out of place. You spot a small bird’s nest at the top of the letter ‘R’ of Risky Business, the name of the company that you worked for.

You were a Jack-of-all-trades. Tradesmen was your given work title. A professional in any task given to you. Because the tasks you are given are not ones professionals would take. Cooking, cleaning, rat slayer, chicken chaser, animal fecal matter remover, taste tester, blacksmith, scape goat, joker, fisherman and many more.

These were just a few of the job titles that you have been bestowed upon since you have started working at Risky Business. You only took the job because it played well and it was just a block and a half away from your apartment.

You took a moment to give yourself a once over, after making a impartial judgment you decide to stop home real quick to get a new suit jack that wasn’t covering in food particles.

: Friday Evening 5:05 – Carousel Boutique – Top Floor:

“I’m home!” you shout.

You where greeted to a cloud of gray smoke that was no rapidly exiting the windows were two mares and a filly tried to eagerly try to fan out the kitchen.

The entire room stopped dead in their tracks as every pony in the room looked at you. They had very recently redecorated; your landlord, Rarity had mentioned something about it.  It’s a quaint little hovel with colorful paintings on the walls here and there, and a nice, well-stocked kitchen. Billowy curtains and brilliant bright lamps and silky soft sheets that make you want to melt away into the covers.

Rarity always went all out on the comforts of home.

There was no correlation to staying with Rarity and your affection with her best friend. None what so ever, even though you were paying almost one and one half times more than the normal cost of a room.

You catch a sight of Applejack just as she’s preparing to get another fan. You haven’t had a chance to ask her about what exactly it is she does, though given her namesake, you figure it might have something to do with apples. Even though they hang out almost all the time, you never really got to know very many of them.

The one you did want to get to know was always just out of reach.

“Hey,” she said, causing Rarity to pause with her hoof just on the window pane. “Ya’ mind givin’ us a hand here?” Applejack yelled.

“No!” Sweetie Bell shouted her mad dash across the room made for an almost comical head butt against your thigh. “You can’t see this, go away.”

You extend your hand, reaching done and giving Sweetie Bell her daily pet behind the ears. A long standing ritual since you moved in. Sweetie Bell was always one of those things you looked forward to in the day. She always was bright and cheerful. Like a cute puppy that crawls into bed with you on those cold winter nights.

Before you could even act, almost all the smoke in the kitchen left in an instant when Rarity finally got a window down creating a huge cross breeze. In its wake was a smoldering pile of grey goo on the table was the smoke had been emanating from.

Almost immediately after the room was filled with an awkward silence. There was no hellos, hi, how are you doing, Just a long silenced.

“So… how are things?” you said trying to fill the painful void. You couldn’t tell but you felt like you were missing something.

“Everything is just fine darling; just a little mishap in the kitchen is all. How are things at… work?” Rarity chirped with some mild distaste in her mouth.

“Fine, although I got to cover my friends shift tonight.”

Her eyes narrow and her mouth shrivel up like she’s eaten a lemon Warhead. “Oh. I see. Well do be off soon, I wouldn’t want you to be late for work.” with a look you can only classify as disdain.

It was just a small whiff since the smoked cleared and you finally noticed the several baskets of apples that were piled on top of each other near the entrance of the hall that lead to the bed rooms. “What’s with all the apples?”

“Nothing,” Applejack said nervously. “It’s not a surprise dinner, or nothing. Totally nothing at all. Hey I heard you like apples, why don’t you stop questioning the apples and have an apple.”

“O-K…” You slowly walked across the room. You did like apples, but just as much as any other fruit. You however did spot a fruit that you wouldn’t have minded biting into.

You could tell that you weren’t welcome in the room, something though was different. Something was off, like that was completely staring you in the face. Yet, you didn’t pick up on it. You mind was still set of finishing your friend’s assignment.

“Ok, I have to ask. Why are you three trying to make fertilizer in the house?” you questioned.

“Fertilizer?!” both Rarity and Applejack said in unison.

It was faint at first, barley even audible over the sound of the wind flowing through the house. It was one of those things you never forget and never want to hear.

It was the sound of a girl crying. You wouldn’t say you had a weakness to anything it would be that. You were raised to respect women and care for them. It was almost ingrained in your DNA. If a male was crying you would tell them to suck it up and act like a man.

“Oh, Sweetie he didn’t mean it.” Rarity said.

Her face dropped quickly. She blinked quickly to hide the tears about to well up and overflow, spilling out of her eyes. She looked almost disgusted but I could tell that this was real sadness.

You were sure your heart stopped.

“Sweetie Bell what’s wrong?” you questioned. You could feel your heart pinching inside your chest.

“You lied, Rarity! This is the last time I listen to you!” Sweetie Bell whimpered as she got to her tiny hooves and be lined out the front door and down the stairs.

You stood there momentarily dazed. You had been living with these two for well over half a year now. Granted there were fights, but you never had seen Sweetie Bell blow up like that. Today seemed oddly eventful.

“Sweetie wait, come back!” was all the words that Rarity got off before she followed in suit after her sibling. Not before giving you a death glare.

You flinch a little as the front for of the shop slammed shut.  Leaving you and the Applejack standing in silence. You had started to see a pattern beginning to form.

Applejack thankfully was kind hearted and broke the ice, “don’t tell them I said this, but this would make excellent fertilizer.” She said with a smile.

“I’m guessing this is Sweetie Bells attempt at cooking.” You had seen it a few times before this this time it looked worse. You however didn’t know why she was so down rotten. Sweetie Bell knew she wasn’t the world’s best cook.

“Yeah it is, there is a bit more to it than that but yes this is her cooking.” Applejack said as she started towards the door. “Last night Rarity overheard a particular piece of information about her sister at the girls sleep over. You know how Rarity gets when she gets an idea in her head.”

“What was the piece of information?” you questioned.

“I’m not allowed to say, I made a Pinkie promise. I think you know though, or at least you can figure it out.” Applejack said before taking her leave. “Don’t take it to heart; this family is full of drama.”

You had a growing suspicion that was starting to burn inside your gut. Or it may have been the fumes from the grey mesh that was on the table. It really looked like it should be censored.

You looked at the clock, it would have been cutting it pretty close but, you decided to take a quick hot shower and get the smell of the day off you.

: 5:37 Ponyville Center Market Place:

Shit, shower and shave. It had to be the best three things in the world that a guy needed. Now the day just drifted by, leaving you to watch the sun crawled away across the horizon.

You could tell from the smell in the air and the fact there was pegasi pushing in black clouds there was a scheduled rain tonight.  You loved the rain; there was always something about it, like it washed away the unseen.

You spot the house which you were supposed to go to. It was a small two story cottage that was only a few blocks away from the main street that ran though the center of town. The small garden in the front of the cottage really set off the yellow color of the paint. You were slightly suspicious of the mail box being bent at a ninety degree angle.

Like always, you mentally prepared yourself for you given task. You knew what you had to do, this wasn’t the first time and it wants the last time. You were here to provide a specific service, it is a need and you already have been paid.

You were tradesmen, something that you slightly grown accustom too and liked. Although, you were probably sure you shouldn’t being feeling honorable for this type of task.

You were tradesmen… you told yourself.

You have the front door three sound knocks.

Because tradesmen sound far better than escort or… whore.

The moment the door cracked opened you turned on your game face. You were now representing Ricky Business; you had pride in your work. This is what you chose to do.

You closed your eyed and took a small bowl, “it’s a pleasure to meet you, I am the representative from Risky Business and if you don’t mind me saying you are quite a beautiful mare.”

…

“You think I’m beautiful, no pony has ever said that to me.”

You could feel the twitch in your face begin to turn as the voice washed over you. It was female to be sure. There was though something off about her pitch, it was far too high.

You opened both of your eyes to see a small light purple filly unicorn with a straight blonde mane standing in the threshold of the doorway.  Her blue eyes looking up at you, both in amazement and wonder, only for the skin under her coat to go completely scarlet.

“My mom said I’m not allowed to date until I’m thirteen.” The filly said taking heavy interest in the floor. “Sorry.”

“Oh…” You didn’t know what to say. You particularly didn’t know how to respond to this. Let alone getting rejected by a ten year old. “If you mother home by chance?”

“Who is at the door muffin?”

The little filly turned back, and looked back at you and then again back inside the house. “I don’t know mom.” The filly looked back at you; thigh was almost a twinkle in her eyes.

You stood at full attention when you head the soft steps of a mare peek her head out through the doorway. She had a silky smooth golden mane that just seemed to catch the light perfectly, and a silver coat that seemed to shimmer and gleam in the evening sun. She had a white patch that ran down her muzzle that complemented her eyes.

Although upon closer inspection it looked like she just had a run in with a bag of flour.

Her ash grey wings were folded at her sides as she looked at you, her eyes were crossed, and it only took you all of half a second to recognize the mare. “Oh hello, you must be from Risky Business.”

“Yes, sorry I am running—“

“Are you hungry? We just finished dinner and there is some left over if you like, its mac & cheese.”

You looked down at the filly and back up to the mother. “I wouldn’t mind a glass of water.”

The mare nodded and flapped her wing for you to follow her. The very moment the door shut behind you, it felt like you had just been trapped in a cress pool. The house was immaculate, clean in almost the most extreme of conditionings.

It was the smell, the whole cottage smelled of pure and utter sewage.  You could almost feel your lunch starting to crawl up your throat.

“I’m so happy you’re here.” The mare said as she walked into what you assumed to be the kitchen. “I can’t tell you how bad I need this.”

You only blinked as you looked at the filly, which was now standing inches away from your foot. Her face still scarlet, you were more curious how these two were able to stay with they smell.

 The mare gave a sigh of relief “I know it may seem a little off but would you mind if my little muffin watched, she wanted to learn the ins and outs.”

This question took you back a little bit. Certainly you had mares that had children, but what the living hell?

“No… I don’t think that would be good.”

“Its ok mom, I have to do my homework anyway.” The little filly said as she looks up at you. “I’m studying to go to a school in Canterlot.”

“Well isn’t that cool, I bet you’re really smart.” You were still hung up on the mother asking if she could watch you both have sex.

The filly nodded and quickly made her way down the hall and up the stairs, only just before she was out of sight she turned back giving you on more look before see what completely out of sight.

The mare sat down on the only couch taking up two couching with the length of her body. Leaving the only spot to sit open was right next to her.

“So how long have you been working at Risky Business?” Derpy questioned as she took a sip of her drink. “I hope you don’t mind if I have a drink, it’s been a long day. Mailroom was busy all day.”

You smirk as you’re started to work yourself into a mental groove. “Sure, I don’t mind at all.” You stated as you reached for your water and taking a small sip. “I’ve been working there for a while. Its good pay, considering.”

“I can’t believe your prices are so cheap! Everywhere I looked they were charging sixty bits an hour. With bits being so tight lately,” the mare said with an awkward smile. “Raising little Dinky and everything, it’s nice to find a small blessing.”

You had to think for a moment; as far as you knew you were the only place in town that was legally authorized for prostitution. Your boss being the parents of the local alicorn goddess had its perks.  You however didn’t like talking about pricing.

It wasn’t that it was a sore topic, it’s what it is. You were priced out at twenty five bits an hour.  Only you. All of your co-workers lease out at forty five to sixty per hour. The only reason why was sadly about size.

Dick size.

You weren’t a horse, simply put, why should the mares be paying full prize for less. Like everything in life, you get what you pay for. You however where fair ahead of your co-workers in customer satisfaction. You didn’t need a mile long dong to get off a mare. You however had a full proof strategy too always stay above your co-workers.

You pulled out a small slip of paper from your best pocket... “Normally I would ask you to do this after, but could you fill out this survey.”

You would cheat.

“Oh, I’ll just give you all fives.” The mare said as she gave it a brief glance at the paper.

You loved giving then the survey while you were watching, that way they would always give fives. No matter whom you serviced.

Now though, it was time to get start. No matter how you swung it, you had a lot to do. The world revolved around the good old-fashioned bit, and you had a lot to do before the night was through.

Derpy was lying on the couch with her tail wrapped around her midriff as the tip pointed down like an arrow to a glistening mound that was just hidden by shadows. The smirk of your face grew you looked at what you were looking at.

There was something about the mystery that got you.

The only thing visible before you now was her bubble butt, her tender flanks were just begging for a firm hand. She wasn’t even trying to be shy about it, like she was a defenses little lamb just waiting to be gobbled up.

You had a good idea what she wanted, nothing but a large dosage of hot seed imbedded in her womb.  You subconsciously swallow as you look to the mare, although it was exceedingly hard to pull your eyes away from that ass. Never in your life would you thought to see Derpy in this light.  Her grey coat looked glossy in the lighting. What was really pushing your buttons was that innocent look on her face.

Oh fuck yes.

It took all of your will not to jump her at that moment. There was a process to everything and you were hell bent on making sure this mare could walk after you were done.

You decided right on that moment the produce, massage then foreplay the eating her out.  Fingering, more eating, doggy style and then missionary and finish with anal. It was a standard that was always worked.

Almost subconsciously, you move your hands to her butt and take a handful in each palm.

The last thing you remember seeing was the bottom on her hoof.

: Derpy’s House 9:09:

Cold.

Your face was freezing.

Your eyes flutter open, only to fall shut again.  Breathing came next, almost a forgotten act that was supposed to come naturally, the first few were magical.  You eased his head to the side, there was a window, stainless steel and the sun was long gone into the night sky.

Only for two giant golden eyes to cover your field of vision.

“Are you alright?” Derpy said as she moved the ice pack off of your face.

“You kicked me,” you said flatly.

“Sorry… I didn’t mean too. You accidently grabbed my butt and I kind of panicked.” Derpy said.

“I was going to give you a massage, if you were that sensitive why didn’t you—“

“Why would you give me a massage?”  Derpy questioned.

You grit your teeth as you touched you face, there was a bandage on your cheek giving a new gash below your right eye.

“Look, I have dealt with sensitive mares during sex before. If you wanted it slow I could—“

“Sex?!” Derpy’s eyes shot wide like dinner plates as her force herself back into the chair. “There is no pony way I am going to do that!” she said, she could feel her face flushing. “I-I hardly even know you!?”

“What do you think you’re paying me for?” you said.

Derpy looked back down the hall, “To fix my toilet… it’s been backed up for almost two weeks... Me and Dinky have had to use the upstairs bathroom.”

You were at a loss of words, there was no way even with it being Derpy there is no way anyone could have miss understood the guidelines. There is a huge difference between sex and plumbing.

“Do you still have the receipt the pony gave you; you should have got a yellow or black receipt.” You said. It was simple enough, all yellow receipts where non-sexual requests. Black was sexual.

Derpy went back into the kitchen and reappeared almost a tenth of a second later. In her mouth was indeed a black receipt. She laid the paper on your lap, “Here.” She said mildly worried.

You could tell from just looking that it was a sexual request.  It only took you a minute to read of the important details. Under requested details there was a simple statement. ‘Unclog my sump.’  Although the ‘S’ was slightly miss printed and looked like an ‘R’.

You had to admit, you would have loved to unclog her plump rump…

“Who wrote out your request?” you said. It was taken out on your lunch break.

“I don’t remember his name but he was a griphons with—“

SQUEAKS

You waved your hand weakly, “I’m sorry there has seemed to be a misunderstanding. Not on your part, clerical error. I will see you get a full refund and maybe something more as compensation.”

Derpy just looked from side to side, “I’m sorry… I just don’t know what went wrong.”

“It’s alight.” You said as you rubbed your check. It felt like you got it by a damn train. You took a moment to shake away the pain, it hurt like hell. “So where is this toilet?”

“You’re still going to fix it!?”

You had to admit, you still wanted to do a good job. Even if the request was different than expected. The Sparkle family paid well and the business had always been good to you. Besides, this was good karma, which meant good things where bound to happen to you.

Good things like maybe being able to talk to Fluttershy.

You hoped.

“Yeah, don’t worry ill see to it you still get your refund too.” You said with a toothy grin. “Besides, I have fixed the toilet at Risky Business almost a hundred times now. I’m sure I can fix it in about a minute at max. Just don’t flush the upstairs toilet.

Derpy lead you down a small path with a grin on her face. Maybe she was doing it for your benefit or maybe she was doing it subconsciously but she was waging her tail just even to give you a small peek of her small mound. It looked almost surreal.

Although you could not enjoy it anymore when you came to the bathroom door. The smell that was emanating from it could only be describing by the gasping and gurgling sounds coming from your throat. You could taste the air.

You almost chickened out as you opened the door to see the ceramic bowl that was filled with a placid array of mirth and excrement that only could be seen in movies.  You had to admit, it did have a slight resemblance to Sweetie Bells cooking.

You striped off your jacket and undershirt, if this was anything like the one at the store. You were in for a hell of a time.

Fourteen Minutes Later

The wall eyed mare politely excused herself from watching you work. It was almost shameful that she allowed it to get that bad. Life sucks when you can’t afford what you need right when you need it.

The mare though had her own job to do, she was a mother still and she had to make sure her little filly went to bed. Tomorrow was there mother/daughter day.

Her trip though was short as she seen her filly dart from one side of the hall to the other. The filly knew her mother’s hooves steps.

“What are you still doing up muffin, its past your bed time.” Derpy said in a mildly scolding manner.

The filly froze just as she was inches from her door. “Going to bed right now mom.” She said without even turning.

“Ok, Hun. Oh and don’t use the upstairs bathroom for a day or so ok Hun. We just fix the bottom one so use that one for now.”

The filly turned back, “I just used it mom. I had to pee.”

Derpy opened her mouth and shut it… she didn’t say a word as she quick turned and bolted down the stairs. Her gallop went from full speed to a dead stop as she rounded the corner. The entire wooden floor was covered in brown murky water that was crawling from under the bathroom door.

One Minute Prior

Your arms were on fire, it was a tough fight… but you won.

“I’m going to go check on Dinky.” Derpy said as she exited the bathroom.

“Good idea.” You said as the moment the door shut you almost doubled over. This was far worse than anything you had ever gone through at the shop. Thankfully good old fashioned hard work and ingenuity pay off again.

You honestly believed in good karma. If this didn’t get you brownie points for the universe, you didn’t know what would.

SPLOOSH.

It was then you looked up at the ceiling as the ever discernible sound of a toilet flushing.

You looked down at the bowl to see all of you hard work now rapidly making its way back to the surface and being airborne.

“Oh shit.”