Sunset's Prostitution Problem

by Michael Hudson

Rating: mature
Tags: Equestria Girls, Sex, King Sombra, Sunset Shimmer, Drama, Porn
Length: 5632

Sunset has always had problems with money. Even a part time job hasn't fixed it but it has let her cut back on her more... illicit activities. Too bad she has one customer she just can't quit.

Sunset has done things she isn't always proud of. Before she was reformed she would often just accept them as a means to an end. She would do anything after all if it meant taking over Equestria. After she was reformed though? Some of those things got much more problematic for her. Things she didn't want to usually think about or do anymore but rent has to be paid and food needs to be bought, especially if you don't want your friends knowing that before you turned eighteen you lived in a box behind a pizza place.

She's mostly cut herself off from those things though. Forgotten them and moved on. If it weren't for one client who simply was far too generous to quit, she'd be done. Maybe this time she'll stop it, especially now that she'd having to do this at school of all places.

Contains: Prostitution Large cocks Creampie Public Fucking Dom/sub After care/Protection

Cover by Marenliscious

Published 2020-04-02 18:00:02 UTC
Last updated 2020-04-02 18:00:02 UTC

The Last Time

Sunset tapped the side of her arm as she scowled and awaited for her client. He’d always been prompt with her before and… She sighed as she shook her head. She knew why he was taking his time. This wasn’t exactly the easiest way for them to meet. He would be here any minu-

“Hello.”

Sunset jumped at the deep voice and slid away from him as she put a hand over her chest. It was indeed him, just as she had been expecting. Dark, black skin, long hair that matched, and dark, menacing eyes. They’d always looked at her like a snake after his prey. Before she reformed she had wanted to prove them wrong. That she wasn’t just something to be trifled with.

Nowadays it made her really want to cut off this deal they had. It scared her, especially with the shivers it ran up her spine. She didn’t exactly have the same stubbornness that could fight it anymore after all. Well, that and…

The man pulled out of his shirt pocket a large fold of bills and extended it towards her. It was just as large as it had always been. No, a little larger. It had to be an even more excessive tip than usual for putting up with his request. Not that she could figure out why he’d made the request. She couldn’t tell him no though as she took what was likely to be half of her rent this month. Not when he made it so she only had to sleep with him so she didn’t suddenly have to admit to her friends how broke she was even with the sushi job. “Thank you, Professor Sombra.”

The man’s eyes softened a little as he smiled before extending a hand out and petting her. Sombra’s hand then slowly trailed down her cheek. His fingers were so soft and-

Smack!

Sunset stumbled a little as she put a hand to her cheek. She blinked a few times as she considered what she had screwed up before she looked away and gripped her arm. “S-Sorry, sir.”

Sombra smiled a little as he once again pet her. His little request was more than acceptable after all but Sunset had let her nerves get the better of her so she forgot about it. She also knew she would have to obey whatever he had to say now. Not that it was all that unexpected as he said, “Strip. Entirely.”

Sunset’s cheeks began to turn red as she began to recenter herself. After all, she had to get back in the right mindset for all of this. To just take care of him, ignore any… problems he gave her, and then leave. It was just another fuck. That was all. “Then let’s head to your classroom.”

Sombra’s eyes narrowed before he gripped her hair tight in his hand. His voice was as cold as before but this time it sent shivers down Sunset’s spine as she realized that it was far, far more commanding than usual. Like he had all the power here. “Now.”

Sunset’s eyes darted around before she grit her teeth and turned her head. It hurt but she wouldn’t let him have such an insane request easily. “I may be eighteen but you’ll lose your job instantly if we got caught. You aren’t that stupid are you?”

Sombra was dead silent as he looked down at her. Slowly he finally began to move as his fingers slowly slipped out of her hair. With each digit that released her though, his eyes narrowed more and more and his normally stoic face turned slowly into a scowl.

It was as Sunset saw his open, flat hand that she yelped, “Sir!” Her heart beat a mile a minute from having realized her mistake just in time. After all, while she called the shots she had to be careful of how much she pushed Sombra. He never got truly abusive. Slaps and grips were all he did. Things that reinforced lessons and helped her get where she was. When he went too far were the nights she held him and…

Sunset shut her eyes to the thoughts before her heart sank. “I do not need this job. My past files pay me plenty. If not, then you wouldn’t have a job.” Sombra then stepped closer and towered over her by at least a foot. “If someone saw you out here performing your duties then you’d be the one in bigger trouble.”

Sunset quivered as her eyes darted around them. They had chosen a fairly secluded part of the school and it used to have a flickering light that most people expected to fail any day now. Well, it finally did. Three days ago. The same day he requested they do it at the school. She swallowed hard before looking back up at him. “You… You don’t want that to actually happen to me, right… sir?”

Sombra tilted his head before shaking his head. “That’s why I chose here. No bathrooms are this way, there are few active lockers in use, and I have told the janitors to leave this area alone until the end of the day due to the lack of traffic.” He then sighed as he said, “Helps that everyone fears me.”

Sunset bit her lower lip. He was right after all. About all of it and her own calculations gave the two of them getting caught, especially with how he’d taught her to keep her voice down so her screams didn’t hurt his ears. Besides, focusing those energies back into her body had made things much more… intense. The fact that he brought up his softer side didn’t help either. The fact that being his whore had actually let him get closer to her than he likely did to anyone else.

She sighed in defeat before reaching down and grabbing the bottom of her shirt. She began to peel it back before Sombra barked, “Faster. We are on a time limit.”

Sunset’s body didn’t even pause to take it in as she stripped the shirt off and then moved down to take off her shorts. It wasn’t sexy but it was what she had to do for this. Besides, she expected any second there would be-

Click.

Sombra had never been much of one for her stripteases. He chose her outfits, positions, almost everything to do with their sessions and so skipped something as banal as her simply disrobing. Or, at least, that was how he put it. It had been one of the things that infuriated her the most.

Now? She stood up and held her breath as he held her bra aloft. He wouldn’t do what he normally did after all. He couldn’t. Not here.

As if knowing her thoughts he threw the bra behind him. Out of reach. Unlike usual though he did say, “if you do your work properly then you will get it back. Hold back and I will leave you without it for the rest of the day. And no, I do not care that you still have gym.”

Sunset nodded as she tried not to cover her chest. In any other setting she would have shown off with it. After all, she was only beat by one of her friends and Rarity and her often got into arguments about whose tits were better, though that happened mostly when she was doing outfit measurements. No matter what though, her tits were a bit bigger than her head and one of the top ten racks in the school, easy. She also knew he had a weakness for them and so she would shake around a bit while they were out. He might not like the strip teases but he definitely liked her dances. She also thought that that was why he normally took her bras as ‘keepsakes’.

Here though? Here she almost hated having them out as her eyes darted to the sides of the hallway. She almost couldn’t think of what being caught would be like. Would she get angry? Flustered? Cry? She didn’t know but she knew it wouldn’t end well. She shut her eyes as she tried to force the image out.

It was then that Sombra’s hand stroked her head again. “I will protect you. You simply must trust me.”

She smiled a little as she thought about their first time together. He had said something very similarly once he found her. He had then made good on that promise with a whole month’s rent from one night. She had suspected back then that it was due to his specialization in psychology but nowadays she just accepted it as part of who he was. That he was just looking out for her. It was part of why she hadn’t said no to today even if she was nervous about actually doing this work at school.

She nodded to him and Sombra made a gesture for her to turn around. She bit into her lip as she did as she was told and almost ate the poor bit of flesh as he said, “Bend over and hands on the wall.”

Sunset did as she was told. Her shorts were still around her ankles and were most of what she could see beside the floor. She was a little surprised not to be told to get on her knees for him and to be mounted like the ‘puppy’ that Sombra would often call her. Even to this day she took it as mocking her. He said as much whenever she told him to stop. ‘You do not know enough about the world for me to call you a bitch yet, especially while under my guidance.’

She took a slow breath out as she tried to stop her body from shaking. This was so far. Too far for her. Instead of her body rejecting it outright it only made her normal reactions to his treatment more extreme, especially after he had told her to trust him. Then again, being fucked by someone for almost an entire year would lead to a girl getting kind of excited whenever she was about to have another taste.

Well, at least, so long as you enjoyed it. Sunset… Sunset hated how much she did. Even her first spotting of his cock had shut her up good. If it weren’t for how long of a history he’d had in this world she’d have sworn he was Equestrian with how large his cock was. Instead, it was why she even met him in the first place. Why he used prostitutes. Normal girls simply wouldn’t let him fuck them. Not usually at least, let alone anyone he could meet through work. Not that he had many repeat girls after he spent one night with them.

Sunset was different though. Her body was mostly human but there were vestiges of her old self. She could eat almost anything a horse could and be just fine, her body was much stronger than others usually and, well… she was still ready to be bred by a horse or human. So, when he began to fuck her, she was the first person to literally ever be able to take every inch of him.

And, short of finding a stable and creeping herself out with this world’s unnatural looking horses instead of ponies, he was the only one she’d found who could properly fill her.

She shivered as she heard his pants hit the ground. She couldn’t freak out. Couldn’t show how weak her knees were right now. How ready she was to run if it weren’t for him being there. For anyone being there really since she hated showing off how weak she was nowadays. She couldn’t help but wiggle her ass a little to remind him what he was supposed to be doing right now. It would likely be more effective if she had a better ass though but she didn’t have enough fluff there to be thicc and didn’t work out enough that you could bounce a coin off of it. Sombra never seemed to mind of course but she was feeling more than a little self conscious right now.

One of his hands came up to her head and ran through her hair as he began to bend over her. He liked the petting because it showed he cared while putting her in her place. She liked it mostly for it being gentle and relaxing. It was also a deep contrast from the thick, slightly hard, wet cock against her ass. She sighed a little in relief to feel the lube but a part of her wasn’t happy that it meant less time actually, you know, getting fucked. He’d left her plenty keyed up after all and she wasn’t about to come this far to be left unsatisfied.

He didn’t enter her yet. His fingers, slick with the lubricant, instead began to grind along her pussy. She swallowed back a moan and instead felt her body tighten slightly. A slight rise in tension in her instead of getting any relief that letting it out would allow her. She refused to yell normally,especially after he had taught her to do it if she wanted to stop him from getting the satisfaction. That had definitely been a trap but right now she thanked Celestia for it since screaming wasn’t exactly going to help right now.

It didn’t help though as he slipped three fingers into her now and began to make sure every part of her was slick. His words began to come out now as he whispered in her ear, “You’re soaked. I know you’re normally not, but I expected you to be turned off here. Is my little puppy excited? Or is it because she knows her master is fucking her and she simply can’t turn her slutty training off?”

Sunset balled her hands into fists as her cheeks turned bright red. The first option couldn’t be true, even if the statement forced her to hold back another moan. Besides, that was from the more intense foreplay. Not from him being right. The latter though? She hated herself but she’d been wet before he’d even come to her. After all, he had bad nights. Nights where his dominant side went too far and there wouldn’t be anything like lube or what not to slow him down or ready her. She was nothing but a collared bitch those nights for his cock.

He held her during those nights too…

She could almost feel his smirk as he snorted slightly. She could try to excuse it for him touching and moving his cock but it wasn’t likely. Sombra didn’t make noise during this. Or, he didn’t except to talk to her and when he was finishing. It was one of the most unsettling things about him but it only added to his overwhelming presence. The feeling like nothing could stop him.

She couldn’t dwell on it too long though as she felt his wide tip press against her pussy. He wasn’t at full mast yet but that was for the best. He was large enough without getting excited and the two found that it got much harder to stretch her properly if he had a full erection when they started. It was something she had refused for a long time because of how it felt. Now… Well, the days where she felt she was sliding back into who she was were often days that she remembered to be punished and put back into her place for since no one else would.

She reached back hesitantly. She expected him to tell her to get it back on the wall but instead allowed her to grab her ass and help spread herself a bit. “C-C-Come on. You only have so much time and I’m not about to leave you unsatisfied.”

Sombra stopped momentarily before the tip was pulled away. “Admit it. Admit that you’re excited. That you’re scared of the time limit.”

Sunset shut her eyes as she scolded herself. She knew this stuff better. She knew what Sombra was like. What he did to statements like that. She could try to bluff again of course but she was already rattled by where they were that she doubted she could convince him. Instead she would simply have to say… “I’m nervous, okay? If you’re going to torture me like this then I at least want to cum a time or two. Is that so fucking b-”

Sunset’s breath didn’t just catch but was knocked out of her as she almost was slammed into the lockers. His blow was barely contained enough for her to get her free hand back on the wall to stabilize herself even as rapturous pain and pleasure ripped through her body in similar amounts. The man above her had slammed more than a third of his cock inside of her at once and while she could take all of him she did need some adjustment period. What had she done wrong to deserve this all of a sudden?

The pull back was much slower as the sound of her pussy being tightly coiled around him resonated through the hall. It was slick, arousing, and scared Sunset white as she realized how loud it was. Sombra hummed himself before he grabbed her hair again and yanked her head back as his cock came crashing back into her. Sunset’s mouth opened to scream for a variety of reasons but her training stopped her and instead almost made her cum from how much it intensified the wave that was riding through her already.

Sombra’s growl didn’t help as thoughts of pretending she had any control in the situation evaporated as easily as her body's preparations for him had. His words were coated in venom and twisted her stomach into knots. “You keep forgetting your place. What you are and who I am. What comes with those roles. Now, if you don’t want me to start smacking your ass loud enough that Principal Celestia herself will hear it, give me an apology.”

Sunset paused for two reasons. The first was the next, slow pull out of her that she was still fighting against. She was trying to loosen up, to not make herself such a shameless vacuum already, but it was simply impossible. Not when she was already fighting her want to scream. The other was knowing better than to babble out a stream of apologies. Sombra didn’t take those. Not when she fucked up so many times in a row.

So she swallowed her pride, shivered one more time as she felt him stop from pulling out by the tip only and knew another second would cause her to be crashed straight into the lockers with how weak her arms were getting and finally let out a whimper. Not a word. Not an attempt to give him more of her body in return. Just a small whine that she let out she hung her head.

All it got her was a slow, intense push into her as Sombra growled again while his hand stayed just relaxed enough to let her hang her head but it could tighten at any moment again. Put her back in place if she didn’t satisfy him. She also so desperately needed to moan as she kept him riding the high that the rest had left her in. The answer was so easy but it usually came an hour into their nights. Not ten minutes at most.

She still gave what Sombra wanted as she let out a small bark and then began to pant for him. To act the part of the ‘puppy’ she was to him. It was demeaning, humiliating, and it had been the one thing she claimed to still hate even after so many months. It was also the thing that got him to thrust jolt forward slightly and prime her for what she knew was coming.

Sombra entered his rhythm. It would change depending on his mood or his position but it always came. Always reminded her of his complete control and how easily he had learned her body as he began to thrust in and out of her. As he began to help her insides turn back into the mold that it remembered so fondly from every other time he’d been inside of her.

As he made sure to keep her riding that wave of just being under her limit. Just under her moment of climax. Or, well, he normally did. The older man hadn’t taken into proper account just how powerful of an effect that being out here in public would have on her as her panting turned into a small, low, soft growl. Her arms lost whatever strength were in them before she was pushed right against the lockers and Sombra could feel that his cock was most of what was keeping her off of the floor. Not that it was a soft hold as her already tight pussy now begged to milk him as it squeezed him as hard as it can.

Sombra didn’t give in so easily though and pulled her off of the lockers. His arms slipped under her legs before he held her so Sunset’s back was against his chest. She was also spread open wide with her legs over her head as she looked straight down as the giant cock that had slipped out of her.

Well, only for a moment. Sombra didn’t give her a break as he almost dropped her onto the cock. It was really just getting her to the right height but Sunset’s back arched as she continued the pathetic, animalistic noises as quietly as she could while she went back to being skewered on his length. Not that it hurt. Not anymore. His pace made sure of that.

Or, his old pace. He now went into what she considered his ‘angry’ state where he began to relentlessly fuck her again. It was still slow enough to get her molded properly instead of almost bruised like before. It wasn’t out of anger though this time. Not as he said in a heated voice, “Keep letting me hear those growls and whimpers. Let me know how well I’m treating my puppy.”

Sunset had more than a little trouble with that though as her eyes began to roll back. The fact that she could have rolling orgasms was one of her biggest weaknesses when Sombra got like this and it was all becoming almost too much. Her body was just being consumed by a raging inferno inside of her. She didn’t care about the noises her pussy made. The sound of her breasts smacking against her chest from how high they bounced when she was lowered and how hard they came back down almost didn’t reach her ears as she focused on one thing. Waited for one thing that would bring this part of this all to an end.

Then she felt his testicles hit her. Every inch. Hilted like a proper sleeve. Sunset’s body tightened up as the wave finally took a pause. It wasn’t that she didn’t love the thrust but she knew what happened when he hilted her during their first round. She still wasn’t sure if it was due to him not being able to take it or if he was honest in saying that he didn’t want to take forever with these sessions.

It didn’t matter. Not as her pussy clamped down on him and made sure he didn’t hold back any of what she wanted. She could feel it moving through the cock and she shut her eyes as her breath caught. It was just long enough for him to finally release a fountain of cum into her. Her womb was filled in an instant before it began washing around his cum. The hot, sticky seed clung to her walls tightly and her pussy didn’t dare want to let him go. It didn’t have much choice though as Sunset went limp from sheer exhaustion. She had blacked out for a second as the wave hit her which was far more extreme then she was used to.

She could feel herself be laid on the floor before she watched as Sombra grabbed a towel. He slowly cleaned up his own cock before swiping at the floor and then shoving it between Sunset’s legs. “We can’t leave many traces of today so rest a bit.”

Sunset hung her head to the side as her breathing slowly, very slowly, began to normalize again. She couldn’t believe how far she’d gone so fast. How much of a pathetic slut she was acting like just because they were out in public. It didn’t matter how good it was when it only made her feel like this was all she was.

Sombra stopped in his gentle pacing for a moment. Sunset was used to the pacing since it kept him stretched out for the next round but the stop was different. She didn’t say anything as she tried to figure out what it was. She couldn’t see anything, her own sweat mixed with his was all she could smell, and all she could hear was her own breath.

At least, before she finally heard the two sets of feet that Sombra must have. She was frozen in place. Even if she tried to move she couldn’t. Her legs simply were too weak and needed more time to recover from everything. She looked towards Sombra who kept listening before he began striding down the hall.

Towards the sound.

Still naked from the waste down.

At the same moment she heard the feet reach the end of the corridor Sombra turned to whoever was coming. Then there was silence.

When finally something spoke it was Sombra as he barked out, “Hall passes.”

The people before him must have paused to do anything because Sombra merely reinforced, “Hall passes! Or else I’ll assume you snuck out of class to come here and fuck.”

There was a high pitch squeal that Sunset recognized as Fluttershy’s that came with that before Sombra finally took whatever the pair extended towards him. Sombra took a moment to inspect the little pink slips before Sunset could hear Fluttershy begin saying, “Why are y-”

“Neither of these passes say anything about a need for coming over here. One for the nurse and one for the restroom. Both of those are in the opposite direction. One of them is even on the entire opposite side of the school. You two were coming here for something you’re not allowed to, right?”

A voice squeaked out, “No,” that Sunset didn’t recognize. Sombra answered that to some extent as he said, “Oh? Marble Pie, right? You’re not the malcontent that your sister is. If you weren’t doing something you’re not allowed to then,” his voice becoming a low growl that made Sunset shiver, “What. Are. You. Doing?”

Fluttershy spoke up again as she whispered, “Hiding. She… She got too overwhelmed.”

Sombra turned his head before finally addressing the elephant leg in the room as he said, ‘You two don’t seem to be so overwhelmed as to stop staring at me. Do so any longer and I will assume you want to have more than just a look at it.”

The silence of their first moment came back as Sombra stood there like a confident statue. After long enough that one of the girls tried to speak again, Sunset assumed, Sombra spoke again. His voice was much less severe though. Much less threatening. Almost… fatherly.

It reminded Sunset of when he paid for her to have a month off. For her to cope with having changed as fast as she had. Even he’d admitted that it came from more of his savings than he’d like to admit but that still hadn’t made him fuck her. Not once during that whole month. The words even reflected that.

“I make it my job to keep tabs on students. I’ve been here for over a decade now and being able to see a disaster coming before it hits usually has helped me keep those who need it safe. So,” he said as he crossed his arms, “you two need somewhere safe to hide? I know how hard it is to get one of you to even speak so I’m not remotely surprised. I can make one of each of yours free periods as a classroom assistant to me where you won’t need to do much. I can even try to make it the same period. This period even when I have no class.”

He then bent forward. When he had done this for Sunset, he had told her that if he heard about her fucking than he wouldn’t keep being with her. His generosity wasn’t to be abused like that. For these two it was, “You two can’t talk about what you saw here today though. Not to a soul. You do and I won’t be able to do this for you or pull the strings at the college in town that would get you a hiding spot there too. This isn’t a threat. It’s simply facts.”

There was another long pause before Sunset could hear the two sets of feet take off down the hallway. Sombra watched them for another few moments before he finally began walking towards Sunset. Where as he had been mostly erect when he started talking to them he was now flaccid as he walked. When he finally got to her he said, “The mood has been ruined. Let me help you get dressed and ready for next period.”

Sunset blinked a few times before simply saying, “You could have gotten dressed and left. You… You didn’t need to risk that, sir.”

Sombra shook his head. “It wasn’t much of a risk. The steps were attempting to be quiet but they were loud enough to mean the owners were nervous. It was slipping them up and that meant they weren’t here by accident or with permission. The slowness of the pace meant that they weren’t excited to be here. More scared. I assumed it was either a more stoic girl like Marble’s sister or shy girls. Either way I knew I could keep control of the conversa-”

“That’s not what I meant sir. I meant that you let someone have leverage on you. You don’t let yourself be weak or vulnerable so… why?”

Sombra looked down at her with a slow sigh. “I’m… sad you need to ask. All the more reason to get you dressed I guess.”

He was right. Sunset had mostly asked because she tried to refuse what it meant. Refuse the final nail this laid down. She could ignore it no longer though.

She slowly got to her knees as Sombra went to grab her bra. Her arms slipped around her legs so she could stop them from going further before, without a moment’s hesitation, she brought her head closer and kissed his cock. Her eyes then went up to Sombra’s and she whispered, “I’m sorry, master. Your puppy… Your puppy never trusted you like you kept telling her to. Not as much as you always deserved. I… I want to properly serve you for everything you’ve done. Please.”

Sombra stared at her before leaning down and petting her. “It’s not sir, but master is much better.” He then gave her a rare smile as he whispered, “I accept it though, as I always have. I’m just happy you finally caught up.” He then straightened out again before pointing to her clothes. “You still need to get dressed though.”

Sunset nodded before going to grab her shirt before looking back at Sombra. “My bra?”

Sombra smirked as he looked at it and then turned away. “Animals don’t need undergarments. You’re just going to have to get used to showing this symbol of your status to the girls in the changing room.”

Sunset winced at the statement. After all, she thought she’d done well. That she was a good girl even before she accepted her place.

It was then that Sombra stopped and stated, “After school you will go directly home and begin packing. Your master will be there at six to pick up his pet and bring her to her new home instead of that hovel you live in now. A good girl should never be stuck in such an awful doghouse.”

Sunset blinked a few times before she shut her eyes and bent down to let her forehead touch the tile below. If what he said was true then there’d be no more rent. No more having to wait for a phone call from him to make sure she could pay rent or get food. She’d have all of those things and someone to protect her from what this world might throw at her and not just Equestria.

She looked up to thank Sombra only to see him gone. She still smiled though as she sat back. He wouldn’t allow any sort of argument after all which meant he had made up his mind and there was no changing it. The only question she had left to her was how long ago he’d made this decision.

Well, that, and the much more exciting question of how he would punish her for taking so long to figure this shit out.

Author's Note

If you like this then I have one of my erotic books out for free for the next few days to help everyone with the cabin fever and you can pick it up over here!