The Night Worker

by WanderingPuffin

Rating: mature
Tags: Sad, Original Character, My Little Pony: Friendship is Magic, Pinkie Pie, Sex, Caramel, Cheerilee, Slice of Life, Dark
Length: 4429

A male escort, a client, a job to be done. A story about the humanity that can be shown and destroyed in the worst places.

Moonlit Jackpot is a pony with a double life. He needs money and stallions on the down low are willing to pay for a nice piece of ass. When you know something is wrong can you do it and still be a halfway decent pony?

Published 2014-09-01 21:50:03 UTC
Last updated 2014-09-01 21:50:03 UTC

Caramel

Author's Note

I am sorry if I offend anyone. I am pretty sure the fandom isn't the place for this but I had to write this story. I know that it is crazy. Sometimes I just need to get an idea out on paper. If you are here because of my comedy please understand this will not be the same piece. If you are underage please don't read this.

Caramel

I am a prostitute.

I hate that I am but I am.

I know that I shouldn't be. That sex is supposed to be between a mare and a stallion. Only between loving ponies. An intimate moment.

I chose the dirty option.

I don't deserve sympathy. I got into this work myself of my own accord. Nobody forced me to do the work.

I need money. My mom is sick. Degenerative neurological condition. No cure. Plenty of expensive treatment. The bills just for her home can come up to 100 bits or more a day. More than I can make alone. Treatment=$ Meds=$$$

I work as a a teacher. I love kids. I went to school to get a degree and everything. Took on a lot of debt too unfortunately. Everything would have been fine if Mom hadn't gotten sick.

I'm an only child. Stallion born to a single mum. Dad...I don't know where dad is. Don't get me wrong. I had a great foalhood. Mom did her best. She worked as a factory mare for years to put me through school. I owe her big. I got a job teaching near Ponyville so I could help her out when she needed me.

When I learned about Mom getting sick I tried everything to get more money the honest way. I still sell plasma, I did drug studies, I don't have really any skills besides teaching but I tried to get tutoring work. It still wasn't nearly enough. Eventually a friend suggested the obvious. He didn't want me to do it but he had some experience with it so he helped me build a client base.

I am not a great criminal. I don't know really anything about the world of crime and I end up guessing most of the time about what will keep me out of prison or worse have me found out.

If I get caught I lose everything. I get fired from work. The entire population of Ponyville learns about my lifestyle. I can never teach again. Mom dies even quicker.

I was working on my paper work in my classroom after all the students had left for the day. I teach older students. Middle school mostly. I like that they have not really decided what they want to do with life yet. So many decisions to be made. One thing I do not like about teaching is the numerous grading of papers but I find ways to put up with it. I had almost broken my record for grading the most papers in an hour when a distraction walked into my room. A distraction in purple with white and violet hair. Cheerilee. She taught the younger foals. Everything about her was amazing. Her face, her flanks, her mind, the way she smelled. Even the way that she spoke amazed me. The cadence of it and tone were amazing. She could walk into a room and just "be" and every eye in the room would rest on her.

I hated it. Being around her is sweet pain. Imagine staying next to the world's best bakery if it refused to serve you. You can smell it. You can see it. You can almost taste it. But at the end of the day you are stuck with fantasies.

"Hey, Jackpot. Do you think you could go out for dinner with me?" Cheerilee asked.

I want to say that I accepted. I want to say that we went out to dinner and talked for hours. We liked it so much that we decided to meet up again the next week. It lead to a beautiful friendship that turn out to be something more. That we said yes to one another on a bed of white roses.

But my mom always told me not to tell lies. Even when they hide the painful truth.

"I'm sorry Cheerilee. I can't. I have to meet up with a friend later." She smiled. She walked off disappointed. I hope that it was disappointed. I leaned back to watch her all the way out the door. I know I am a jerk. I have a meeting with a client that I could easily reschedule. That I am an idiot for turning the mare I dream about to go sell my body. You're right

Cheerilee is a pony I put on a pedestal. A pedestal that doesn't have her going out with a sex worker. Even if it is just as friends and coworkers.

I finished up with the paperwork after about a half an hour later. I went home. I still live in my childhood home. I would have sold it except not many ponies want to move to Ponyville so I couldn't find a buyer. Mom is in a special care facility so I live alone. I had to get ready before working. Luckily I don't have any clients who request special clothing so I can go out normally. Still I shower, douche, shave, comb my hair, and add cologne. I pack up the essentials in a small bag that I carry with me. A canvas satchel with a button close that I hope doesn't send off an effeminate vibe. Condoms, lube, poppers, dildos, all tools of the trade when you work the beat. Strange how you change when you work in this trade even part time. You start to develop a sense for good product and what will last and what looks painful to have inside you. Knowledge I could have gone a lifetime without knowing.

We always tell the children at the school. Be curious. Be willing to learn new things. Then they go out and learn that some knowledge shouldn't be gathered.

I am ready to head out.

I don't stand on street corners. That is a great way to get rolled by the police. I have a client base that knows my services. I work completely on word of mouth. I have regulars who have a standing date and I have one offs who just want to prove something.

Today I am meeting a new one. I insist on meeting in public first. Most of the creeps can't hide the freak in them and I have developed a sense for knowing when to walk way. The client insisted on this meeting place. I don't like it. A smoky bar can hide transactions the owner is willing to overlook. This is a family place full of kids. I think of mom and stride in. Celestia save this sinner.

The sign reads. "Sugarcube Corner" Cute, but sometimes cute is the worst emotion I can feel.

Remember when I compared Cheerilee with a bakery? She is better because I can't eat anything at a bakery. I have to keep my weight steady or else I face losing business. Most of my clients prefer their stallions smaller than them. I get complaints if I gain five pounds. Being surrounded by a display of sweets is sorta horrible for me.

"Hey, new friend" a pink pony called out from behind the counter.

Who was this pony? An overeager employee? An owner wanting new business. Could appearances tell me anything anymore?

"A cup of black coffee, as strong as you have it." I believe that coffee should be capable of doubling as coffin varnish.

"Cupcake? first one's free." She presented me with a treat that I could have loved. Chocolate cake so dense that it seemed to absorb all light into it. Frosting that looked as light and fluffy as cotton.

"No thank you. Just coffee and a quiet table." if there was one that could be found in this place.

"Ah, what's eating you?" the pink one didn't seem to get the idea that someone could want to be left alone.

"Nothing," I say turning my face. Somehow she is still in front of me when I turn around.

"Nope, not nothing. Definitely something." Her tail twitched.

"Please leave me alone," I asked quietly.

"Okie odkie loki." she responded in some foreign tongue.

I found a dark corner that seemed far enough away from the kids to allow me some privacy. I may be scum but I have my standards. Eventually I saw my client walk in the door. A decent looking pony. Brown hair, a light tan coat, three horse shoes in a circle for a cutie mark.

A stallion

I consider myself heterosexual with perhaps a few homosexual thoughts. I know saying that when I admit I have a stallion here ready to pay me for sex is a bit closeted but it is true. I am also pragmatic. There is no market for heterosexual male escorts in Ponyville. I know there is some sort of idea of the sexy gigolo entertaining bored shapely housewives. I have never met one and especially never met one that would be willing to pay me for something they could probably get for free at the local bar. So I did the logical thing and sold myself to somepony who was willing to pay me. I am versatile as they say in the community. I am willing to play the part of the sensitive feminine bottom or hyper-masculine top if the pay is right. Fetish work is extra.

"Over here," I call out when he seems a bit lost.

"Thank you for meeting me," he says nervous as can be. He seems to be about my age. Good muscle tone but not a gym bunny.

"No problem," I say trying to keep my voice down. Three foals are already watching us.

"I have never done this before. I have a marefriend and everything. I mean I have thought about it but never actually tried it. My fiance proposed and I just want to make sure that I am... you know ... correct? I don't want to wake up in twenty years asking myself if it was a mistake you know? Big Mac told me about you and is it true that you will... let me?"

A good stallion would probably walk away rather than cheat on the other mare. I gave up my goodness a long time ago. All that is left is the scum. Cheating can perhaps be blamed on the society. The high number of female births to male births means that just about every stallion is expected to marry to keep a stable population. There is the idea of keeping a herd but it is discouraged around here and interbreeding can quickly come into play if all the fillies and foals share the same father. Being discouraged doesn't destroy gayness though. It just forces you on to the down low where there is always somebody like me willing to provide. This logic doesn't make it feel better though. It just makes it seem like the logic of the damned.

"Aw what a cute couple." I saw the pink pony staring at us again. By Celestia's horn she was annoying.

"Miss, we are just a couple of friends."

"Nope, that was definitely more than a friend twitch. There is something going on here."

"We should go." I leave a couple coins on the table to pay for a coffee I never touched. My client had gone pale.

It is only once we get outside that the brown pony starts to panic. "Oh what am I doing. Carrot eats at that place. Pinkie will tell her and she will tell Sassaflash. She will tell everyone and then everyone will know I like colts"

Paranoia, that is unavoidable sometimes. You never get rid of it but you learn to live with it.

"If you already like colts why do you need me?" I snark quietly. The question has the desired effect of snapping him out of the spiral. "Your options are as I see them: You can go home and forget about me. I won't charge you. You can tell your girlfriend all about what we were planning. She might forgive you. Third option: We find a quiet place and just continue our business like nothing has happened. You can easily explain a single night out. Even if this Pinkie does tell your marefriend you can easily explain it as Pinkie being crazy. You have your fun and then you go back a better coltfriend than ever."

I arch my back and throw out my ass to draw his eye to it. I know the words that can make a grown stallion think with his cock rather than his head and I can see him greedily eye my ass. This is evil I do willingly. Swallow down my poison little stallion. Justify it in your mind.

He nods, "You are right Pinkie has always been weird. I can probably get away with one night,"

I agree quickly. "You are saving your mare from a possible broken marriage. You are doing good here no matter what society may say."

Swallow down the damnation I offer. Give me money so I can have a little more time with my mother.

He seems to accept my answer. "Okay, what do I need to do?"

I let my experience take over, "We go someplace private and have a little fun. Should we go to your place or a hotel Mr.?"

He pauses, "I'm Caramel. My place is close so we can go there." He leads the way to the apartment. It is your average studio apartment bachelor pad. I walk in to a mix of ideas. It is seemingly clean but with empty cardboard boxes piled up in the corner. A pile of laundry in a basket in the hall. Dirty dishes in the sink. If I wasn't paid for my love I would immediately begin cleaning. I follow him until he leads me into the bedroom. At least the bed is made. Small favors.

He tries to kiss me but I stop him. I have him hot and bothered. Time to name my price.

"Did Big Mac tell you about my fees?" Caramel seems put off that I would mention something so crass when he is trying to seduce me but he obliges. A bag of bits is passed to me. I look in. A generous amount. Enough to pay for a whole night with me.

"I don't want to hold back." He states. We discuss what he wants to experience briefly. I have to explain a few things but eventually I get an idea of what he wants.

It begins with a kiss. Both of us sitting on the edge of the bed. Our hooves running over each others bodies. He is clumsy. More used to kissing someone who is too in love with him to correct him. Not a cold professional who does this for a living. I guide him with my hooves. Our lips rubbing against one another. The sickening exchange of spit. He thinks that the highest talent one can have is to force his tongue into my mouth. To spear my mouth with force until I almost begin to choke. Poor boy. I push him away to catch my breath. when he attempts it again I hold him away with my hooves. I plant my small kisses across his lips. I run my lips down his neck until I can feel his pulse with my lips. I hold him close his chest close to mine. I can feel his breath upon my back. I can feel his heartbeat matching mine. His erection grows to gently poke me. He takes this as permission to leap forward and tries to force my head down.

"We have all night." I say gently reminding him. He cringes out of shame. Cute.

"Lets try something. Lie down on the bed." A great big smile breaks out across his face. He lies back with his hooves behind his head. His erection stands straight up and bobs gently back and forth. He thinks I am going to suck him.

Instead I pull out a bottle of lotion out of my bag. I can see his confusion in his eyes. I squirt some in my hooves and begin to gently massage him. I climb on top of him with my buttocks straddling his waist and begin to rub all his big muscled limbs. I coo sweet praise about his strength and manliness. I gently rub in the lotion. I am not a professional masseuse but I make do with what I have learned. I maintain eye contact to entice him. A thousand thoughts communicated without words about how much I want him. About what a catch he is. About how much I am looking forward to soon being under him. All lies of course. Eventually he bucks under me. His emotions boiling to a point of no restraint. My cue and I drop down to do his legs.

I climb down to my bag. I pick out a black plug and drown it in lubricant. I hate this part. I plunge it into me quickly. I am full to capacity. Unlike what most ponies seem to think assholes are not super stretchy. You have to expand it first and give it time to adjust or you can't fit anything in there. My first few jobs taught me well enough. Sure they fit but the pain was horrible. I have learned better since. Especially since most clients do not want to take it slow.

I take my place between his legs. Caramel is a reasonably endowed pony. He comes up as about average. One of the few perks about this job is that it has taken away any fear of me being a lesser stallion in this area. I hate this part as well. Hard to pretend to be hetero when you have a cock in your mouth. I start to lick and try to pretend that it is something else. A popsicle, an ice cream cone, a tofu dog. I run my tongue up and down it as I feel all the veins and the slickness. I take it in my mouth as I hear moans coming from the bed. I suck it as I run my head up and down its length. Part of me wants to bite. To chop down with all my force. Just so I won't be so damn good at this job. So I can quit and tell mom that I did do everything that I could do for her. But I don't. I focus on the tip of the penis where most of the nerve ending are while my hooves play with his balls. He moans harder as I continue. Should I stop? Keep him hard so that I don't have to wait while until he is hard again so he can claim my ass? I let out a sigh and continue even as I feel him tense up.

My mouth floods with the tangy and yet sickening cream at the same time. What would a hetero do? Spit it out in his face?

I swallow. Again and again until he runs dry.

Caramel seems pleased, "Wow, Sas never does that."

Of course not. She probably doesn't depend on you for money. It is probably a relationship based on trust and mutual admiration rather than what we are doing. Idiot.

I smile coyly, "I aim to please. Are you wanting to continue with your "exploration"?" I rub the inside of his thigh.

"Oh yeah," he say almost leaping from where he is lying on his back. Mistake, he ends up throwing me off his bed. I reach out trying to grab anything. I end up pulling the covers off the bed. Caramel ends up falling down on top of me with his head at my ass.

"Okay, I like that you are eager but tone it down okay?" I can't exactly keep up the sensual professional look when that happens.

He doesn't reply. Suddenly I can feel the plug being pulled out of me. "Hey, what are you doing?" I ask quickly my head still spinning from where it hit the ground. He still doesn't respond. Instead I feel his forelegs wrapping around my thighs. A warm wetness touches my hole. I try to move my head to get a better look. He is slurping eagerly at my ass. His tongue running up and down my crack. I can't help a gentle smirk coming across my face. This colt has done his homework about pleasing a stallion. Probably gathered from whispers in a locker room and smuggled magazines. Either he is really wanting to try everything before he ties the knot or he is in a closet with a very open door.

I know I should be putting on a show. Gasping for breath and writhing out of control due to the pleasure but really I don't do this activity for a reason or at least I don't do it without protection. The pony digestive system leaves a lot of disease behind even after you clean yourself. Nothing feels less sexy to me than wondering if you are going to be bent over the toilet with e-coli the next morning.

Still I let him indulge himself for a while until I see he is back to full mast. I can use all the lubrication I can back there.

"Thank you very much," I say causing him to pause. "How did you know about that?"

"Well my older brother was talking about mares and you see," he cringes back into himself ashamed. Oh, could he be any more adorable?

"Shh, baby," I say kissing him again softly.

"You can go." He says starting to tear up. "I am a coltcuddler. Oh, god what am I doing?"

I pull him into a close hug. I want to say something. To tell him that just because he licked me doesn't mean that he is bad. That gay or straight is not an either or question. That no matter what we do he still loves that mare. I get called on to provide comfort after all. All the stuff I know myself to be true but can't accept.

"It's okay," I whisper over and over until he stops sobbing.

"Look, I can leave but you already paid me." I say trying to wipe the tears away. "Do you want to just continue going through with everything?" Maybe this was just a fantasy he needs to get out of the system.

"Yes," He said finally.

I pick a condom out of my bag of wonders and sit Caramel on the edge of the bed. He sits morosely as I wrap him up. I cover him in lube and climb on the bed in front of him.

"Okay," I say quietly "Just..."

I am cut off when he suddenly thrusts into me to the hilt. "FUCK!" I shout uncontrollably.

"Don't do that" I shout. He doesn't listen to me. He slams in and out of me. I grit my teeth. Imagine that it is Cheerilee into freaky stuff. You are not getting pounded on a stranger's mattress but instead you are on a date with Cheerilee. She decided to get weird. You are not here you are with her. You are not here you are with her. You are not here you are with her.

How fucked is my life?

Caramel is having the time of his life. I can tell it without even looking. He is smacking my ass.

"Woah, baby who's your daddy?"

Who actually says that? I mean seriously I am a sex worker and I have never ever heard that line.

"We about to launch off baby!"

Was he getting paid by line of cheesy dialog? Was there a camera in here I was not seeing?

slap, slap, slap went his balls as he gave it his all. shouting every cheesy line I think he could think of.

Eventually, I can't handle it anymore and just burst out laughing. He started right along beside me as he finally came. We both collapsed in on a big heap. His softening member sliding out of me.

"Thanks," Caramel said out of breath.

"Anytime, it is what I do," I say casually.

"No," Caramel states plainly. "Not for the sex. For being with me."

Oh, by Celestia. I can't take it anymore. "Look, kid I'm a whore. No soul only a pocket book. If you want a nice pony look elsewhere"

"Do you really think that?"

"Of course,"

"Then why didn't you leave?"

"Huh?"

"You have my bits. I told you you could leave. Instead you decided to help me,"

"Kid, I screwed up your relationship and made you cheat on your marefriend. Don't turn a sinner into a saint,"

"and the hug?'

"Just good business." Wasn't it? "Now I suppose you are just going to break up with the mare?"

"Oh, I'll survive and learn how to deal with figuring exactly what I am. I always do. I just don't think you are quite the hardened pony you paint yourself as."

"Look, you paid for the whole night. Are you satisfied with what you know or should we continue?"

"I'm happy. Keep the bits. I think you need them more"

Idiot I thought as I stormed off madly.

I am a bed hopping pony with no morals. I should a find an all night liquor store and drink myself stupid.

I should go home and forget about him. Just another job.

Why didn't I leave?

Why do I suddenly feel bad?

Idiot, never let yourself get connected.

Maybe I am scum with all my goodness long gone.

Maybe I am just a pony in a bad situation.

I walk through the lonely streets of Ponyville. Strange that a place as nice as this could still have a person like me in it.

The doctors say mom only has six more months at most. Six months. About 4 weeks to a month. Maybe two jobs at most per week.

48 more times I have to do this and I am out forever.

48 more times and then I work on getting whatever goodness I once had back.