Filthy Lucre

by Shrinky Frod

Rating: mature
Tags: Cheerilee, Sad, Drama, Porn, My Little Pony: Friendship is Magic, Fetish, Filthy Rich, Sex
Length: 4405

Filthy Rich does filthy business.

Filthy Rich believes in giving back to the community. He doesn't worry about making a big deal of it, but he donates quite a bit to keep the Ponyville Schoolhouse well equipped.

Of course, he's still a Rich.

He always gets more than his money's worth in the deal.

CW: NC-17, M/F, F/F referenced, Informal prostitution, resentful sex, sex using pretty much every hole available, orientation play,  homophobic language, cheating, open relationship, running makeup, dacryphilia, coercion/blackmail

Story was originally written as an entry for Striptember, focusing more on the prostitution angle than on the stripping angle that I did last year. Story was originally meant to be longer, but it's probably turning into a lengthier series instead. I also have a prequel to this that'll be coming out in the next month or so, probably!

I'm not sure who edited the screenshot in the cover art (I didn't even realize it was edited at first, oops!) but it can be found here!

Published 2022-09-28 21:10:00 UTC
Last updated 2022-09-28 21:10:00 UTC

Chapter 1

Filthy Rich checked his watch as he waited outside the Ponyville school house. The door opened to reveal the Cakes, chatting with Miss Cheerilee.

"Well, the twins are looking forward to joining your new class next year," Carrot told her. "It's going to make the days a lot quieter."

"You'll still have Pinkie working there," Cheerilee laughed. "I'm sure she'll keep things exciting."

"She actually seems to be settling down, now that Cheese Sandwich is coming around more often," Cup pointed out. "Oh, hello Mister Rich!"

Filthy smirked inwardly as all three of their smiles became a little more forced, especially Cheerilee's. There was something satisfying about being a beloved figure in town - but something more satisfying about knowing some ponies had different reactions.

Especially ponies who owed you money.

"Miss Cheerilee asked me to come and look over some proposals for renovations to the schoolhouse," he explained smoothly. "I thought I'd see what it was like to be here and not be apologizing for something Spoiled said at the school board." He chuckled easily, the Cakes laughing along politely before they quickly made their way back towards the bakery.

Cheerilee, he noted, did not laugh.

"After you, madame," he said graciously, gesturing towards the schoolhouse. She turned to lead the way in, her jaw set, tail tucked down tightly. Filthy let her get just inside the door before leaning his head forward to brazenly nip at her cutie mark.

"Mister Rich!" She chided him, hurrying further in. "I did call you here over a business matter."

"And I'm just eager to get down to business." Filthy took a seat and lounged back casually. "Now, you mentioned renovations?"

"Ehem, yes," she nodded, the nerves right back. "As you heard with the Cakes, I'm starting a new class next year. More to the point, you've seen how the town is growing lately, and-"

"Miss Cheerilee," Filthy chuckled as he pressed his forehooves together and leaned in towards her with a friendly smile. "Whatever the reason, it's my wife who's in charge of the school board, an' you know perfectly well that she's the one who has to approve any decisions like that. So why don't we cut the horse hockey an' get down to the point?"

She closed her eyes and drew a deep breath, like she was steeling herself for what was coming next.

"I need to expand the schoolhouse and hire more teachers. The whole town knows it, it's been that way for years, but with the town growing it's only becoming more obvious. The EEA won't provide any more budget because Ponyville, and I quote, 'shouldn’t be charging the crown for its poor planning.' Which means going to the school board."

"Where my wife won't call for an extra nickle spent unless there's a dime coming in for it," he nodded, considering the probable costs. "What exactly are you looking to add on?"

"I'd like to add two more classrooms, with a teacher each. Split things up so that my three classes all pick up full days instead of the shorter shifts, maybe get in a teacher from Mount Aris or Seaquestria if we can find a qualified one."

"Whose salaries will be hard enough to pry out of Spoiled's hooves," he mused. "Of course, this isn't going to be cheap."

"I hope that with a substantial pledge, I can get the EEA to make up the difference," Cheerilee explained.

"You mean you hope I won't have to hoof over the whole amount, so you can actually retire some time," he chuckled. "Get your proposals put together, and I'll see what I can do. If it isn't completely unreasonable, I'll agree to it. Even put a little pressure on Spoiled to stop keeping the school budget as tight as her haunches."

Cheerilee tried to hide the wince at that particular simile, but Filthy didn't especially care.

"Y-yes," she sighed. "Which, I suppose, brings us to the topic of how I'm going to pay you back."

"Yes," Filthy drawled casually. "If I were to make an estimate, we're talking about… hmm… at least one hundred thousand bits, after I take out the tax deductions and ability to donate supplies instead of cash. That's if we don't need to just rebuild the whole school, of course."

"I'm hoping that the EEA will agree to match funds with a large enough donation, so it's not as bad as all that."

"All the same, that's quite a lot of bits you're asking for. And there's no guarantee that they'll make that decision," he pointed out. "Hardly an amount you can reasonably pay back on your salary."

"Not in bits… but that's the way you like it, isn't it?" She frowned, not able to meet his eyes. "Our… our usual arrangement."

"Miss Cheerilee, our usual arrangement would mean I could make you my exclusive plaything for the rest of both our lives, and you still wouldn't have repaid me," he chided. "However, I believe that with a few… modifications… we could still have an arrangement. Allowing me certain liberties we've usually refrained from."

She frowned slightly, giving a look that had stopped playground fights for years. Filthy saw right through it; the faint drop of her shoulders, the sag of her back, her tail drooping behind her.

He'd already won, and he knew it. He just had to be careful not to overplay his hand.

"Well, Diamond Tiara has mentioned wishing she wasn't an only foal," Filthy mused lazily. Panic flashed through the schoolteacher eyes, and he shook his head with a laugh.

"No, no, I wouldn't ask that of you. A little tricky to explain to the mare back home. Besides, I’m getting too old for diapers."

"As if you've ever not had someone on staff to handle that," Cheerilee grumbled.

"And I'd still rather not do it again. However, I do want to alter our previous arrangement in a few small ways. First off, no more condoms. You know I couldn't knock you up if I wanted to, an' I'd know by now if any of my other 'business associates' had anything. I'll add twenty percent to our usual arrangement for that."

"Done," Cheerilee sighed.

"Next, I want our little appointments on my schedule, not yours. That means weekends and holidays, you're on call, and if I want you at my office or even in this schoolroom, no putting me off for a motel room. When I want, I fuck you how I want, convenient or not." There. He'd said it, flat out. Cheerilee's wince when he did was almost pathetic; as if she had any right to worry about language with him. "I'll forgive double when you have to leave class or ditch the Mayor. If I have you travel with me, it's fifty an hour, from boarding until we're back at Ponyville station."

"Travel?" Cheerilee reared back, shocked. "But how would I-"

"I don't care what excuse you give her. Teacher workshop, emergency field trip, none of my business. You're the one trying to keep your marefriend in the dark. I told you the first time, it's easier to let 'em know. Besides, I don't expect it'll come up often, maybe not ever at all. Haven't taken one of my partners out in a year or two… I should look at doin' that again some time," he mused.

"Final offer," he continued, "something new to help work it off. Sometimes I like to have a couple of my partners put on a show. You do that for me, and it's five hundred if it's with another mare. A thousand if it's a stallion. I'll record it, and may join in, but strictly for private enjoyment. One of the few things Spoiled and I do together."

Cheerilee wanted to say no, especially to the last part. The more people who knew what she was doing, the better the odds somepony would let things slip. She wanted to just buck Filthy in the face and tell him to get out of her school.

But her school - her students - needed his support. And she needed to get out from under the debt as quick as equinely possible after that.

What did it matter if she was on one of the stallion's stag reels blowing somepony else? She'd already sold her dignity to Filthy before, to make sure she had the supplies she needed for her class. Her self-respect had followed when she got the printing press for the Foal Free Press. There were times, when he'd been buried inside of her, that she wondered if Filthy was encouraging Spoiled to keep the budget crippled just so she'd have to go begging to him any time the school needed money.

"Do you need a little time to decide?" Filthy asked her. "As it stands, if you find out the EEA will help, you'll be out of it that much faster. If they don't… well, by the time you find that out, I may have changed my mind about the terms I've offered."

"All right, Celestia damn it," she spat out. "Fine. But the shows are on a case-by-case, I'm not letting you pimp me out to your actual friends and saying they're in the same spot as me."

"Of course! Miss Cheerilee, you know me. I may enjoy pushing your boundaries, but you can always say no to me," he reminded her with a smarmy smile. "It just means I may start looking to be repaid in bits rather than services, depending on how often it happens."

"I'm well aware. Of both facts. Is there anything else before we leave for the day?"

"How about we get a start on what you owe me," he rumbled deep in his throat. "What do you say, Cheeri? Relive the good old days when you were cheering for Canterlot Academy?"

"I wasn't that sort of cheerleader," she pointed out acidly. "Besides, what makes you think I even have the outfit or gear here? I only get it out for the Applewood Derby."

Filthy Rich chuckled, wandering over to the supply cabinet and giving the door a light kick. Inside, under a pack of construction paper, was the white-and-yellow cheerleading uniform.

"You forget, my little filly's better about noticing details than she acts. You're just lucky she doesn't care what's in your desk!"

She sighed inwardly, going over to pull her uniform out. This was the part of her life she'd always kept for herself. Her teaching, her school activities, her private life… they were things Filthy wasn't supposed to get.

But if his money was going into them, of course his libido followed. That was how it had gone since the first time he'd suggested how to 'stretch her budget' despite Spoiled keeping the school's funding damned near a decade out of date.

She'd known this was coming. It was too much to ask without him wanting to get more out of it, and this way she'd at least have a chance of getting out from under it that much sooner.

She started to pull on the uniform, the top clinging to her chest and barrel, the skirt short enough to show off her cutie marks,

"The bow isn't a clip on?" Filthy asked as she sat down and started carefully tying it off with her hooves.

"Clip ons fall off," she shrugged before she stood back up and gave him a twirl.

"Well, we certainly can't have that, can we?" He chuckled. He walked around behind her, nuzzling into her mane to cinch the bow a bit tighter and inhale the scent of her mane.

"I'll get the door and windows." He nipped at her ear lightly. "You go up to the chalkboard and get ready to earn some extra credit."

She could feel his eyes on her flank as she walked up to the front of her class, awkwardly trying to put a sway into her hips and tail. She hiked it up, raising her skirt to flash her hindquarters at 'Professor Rich,' and then braced her hooves against the board to stretch herself out.

"You really did miss your calling, Cheerilee." He walked up behind her and nosed her skirt up to nip at her flank. "For a pony who's so good at being a whorse, it's a shame you're a teacher instead."

"I cook too, if you want to give that a shot instead."

"I think I'd rather eat out," Filthy smirked. He nuzzled her marehood, giving it a light lick. "Start with something more your speed."

Cheerilee let out a whimper, trying to get herself to respond the way Filthy wanted. After all the time she’d been doing this, she still hadn't grown to appreciate his oral ministrations, even as his skill improved. He was an expert with his tongue by now, slipping it inside of her and playing the surface along her clit. She was anything but turned on, and knew he could tell as much.

Not a problem that he was having. She could smell his arousal, a musky undertone to it that screamed 'stallion' to every part of her brain even before she heard the sound of his erection slapping against his belly. She tries to tune those parts out, focus on the physical pleasure rather than how much she didn't want to be in this situation.

Hard enough to do somewhere else, but here with the chalkboard in her face….

She pushed the side of her face up against the chalkboard, faking a moan and inhaling the smell of the chalk and slate to mute his scent. Filthy chuckled as he peeked above her skirt, then set himself back to eating her out, finally coaxing a bit of arousal out of her. She tried to go back in her head, to the time she had done something like this once, fumbling experimentation with Big Mac before she'd transferred to Canterlot and met the future Mayor.

It was a workable little fantasy for now, an encounter she'd at least not resented herself for afterwards.

"Don't you want to mount me, Captain?" She asked, brushing her tail along Filthy's barrel. "Mark your mare so everypony else knows it?"

"Oh, I would like that," Filthy grinned, climbing up on top of her and positioning his shaft against her marehood. "Make sure the Mayor gets a good taste tonight," he drawled into her ear, thrusting himself into her tight, barely-slickened body.

Cheerilee bit her lip, hard, milking his cock instinctively as he worked his swollen tip back and forth inside of her. The edge of his flare stroked against her clitoris between winks, helping her body to relax and let him in deeper each time he rocked his hips forward.

"That's a good whorse," he murmured, stroking her sides with his forelegs. "Whatever it takes to help your little flowers grow, hmm?" He slapped her cutie mark and slammed his hips forward, hilting inside of her with a muffled slap.

"Mmph! You don't… hah… have to be a dick about it," Cheerilee panted.

"And you don't have to be doing this," he countered. He nipped the nape of her neck, his cockhead battering at her cervix. She could feel that he was getting close, his cock throbbing inside of her. She knew what he was planning to do, and her stomach churned at the idea, vasectomy or not.

But she did have one ace up her pompoms.

"Do you really want to come inside, Filthy? Or do you want to make me walk home with your seed all over uniform?"

That actually got him to stop for a moment, pausing mid-thrust at the suggestion. She could feel him grinning against the back of her neck as he started thrusting again, hard and fast.

"You don't take it off until you get home, or tonight's a freebie," he warned her. "And you're cleaning up with your tongue after."

"Y-yessir," she muttered, pushing back into his thrusts, already trying to figure out how to minimize the chance she'd be caught out.

She tightened herself around Filthy, hoping to get him off faster. It seemed to work, as he pulled his hips back and pushed her ass down with his forehooves. She felt his shaft slide up the soft cotton of her uniform, and then he went off.

Jets of thick, hot stallion-semen shot out over her back. A few strands shot over her head, splattering against the blackboard. She felt some hitting her mane, pearly white strands tangling with her two-toned pink mane. It dripped down her neck, and then splattered onto her clothes, wet and sticky and quickly cooling off as it soaked into cloth and fur. The sharp ammonia smell of semen filled her nostrils and the rest of the room, as Filthy pulled her rump up by the tail and casually wiped his cock off with a swipe up her marehood through to her dock.

"Mph!" He grunted and stepped back to look at his handiwork. "There's something about seeing a mare-muncher like you covered with cum that's that little bit sexier."

She didn't answer, just turning around and lifting his cock with her hooves to give his cock a long lick. She dutifully cleaned him off, looking up into his smug, arrogant eyes with her own expression of barely restrained disgust.

"If you get me broken up with, I'll- glk!"

Before she could finish, Filthy grabbed her head and shoved himself into her muzzle.

"You'll what, hmm? Tell the whole town their teacher sells herself for crayons and construction paper?" He sneered down at her, fucking her face harder as he recovered from his first orgasm fairly quickly. "Spoiled already knows about you whorses, she'd just make sure you never get a teaching job again for the embarrassment!"

Cheerilee gagged as he forced himself into her throat, his eyes rolling back in pleasure as her neck bulged around his shaft. She closed her eyes, taking the excuse to let herself cry, her mascara running down her cheeks.

He was right, and she knew it. And he loved it.

"That's right, go on and cry." He whispered, shifting his hooves to wipe his semen deeper into her mane. "You say anything an' you're the only one who'll regret it, Cheerilee. That's your lesson! You-"

His balls slapped against her chin as he hilted half-way down the younger mare's neck.

"Do-"

Her throat constricted as she almost heaved, tightening around the tycoon's member as he ground her muzzle into his pubes.

"What-"

She felt herself heaving again, her stomach trying to get in on the action to expel the intruder that was blocking her air, keeping her from sobbing.

"I-"

He pulled back just before she hit the point where she'd have to vomit, saving her that indignity at least.

"Want!" His cock pulled out to her teeth just after he started to cum again, the first shot streaking back along her tongue from tip to tonsils. She panted through her nose, swallowing what she could, more of Filthy's bitter juices dribbling out of her muzzle before he finally pulled loose. He twisted his hips, his throbbing tip smacking her across the muzzle as he shot his last spurt of seed, right across her eyes.

Cheerilee fought not to blink, her eyes burning as she forced an unsteady smile onto her muzzle. Filthy tipped her face up towards his with a hoof, then gave her a patronizing kiss on the forehead.

"Finish cleaning up the mess. With your tongue," he reminded her.

Swallowing hard, Cheerilee wiped the cum from her teary eyes, licking her stained hooves and cannons clean before Filthy offered her his own hooves, now stained by cum and hair from her mane. She followed his hoof obediently as he pointed out one stray bodily fluid or another - a few drops of his seed on the floor, a ring of her own arousal where her marehood had been on the floor while he came on her back. Finally, as her vision cleared, she realized that the last mess he was indicating was the streaks on the blackboard.

And she knew damned well that he wasn't suggesting towels.

Like with the lacquered wooden floor, she extended her tongue, mopping a bitter mix of chalk and stallion from the board, finally wiping the tears from her muzzle afterwards - her tongue stretching out to lick them from her upper cheeks.

When she was done, her tongue was tired and tasted of chalk and varnish. She knew her eyes were going to be red from crying and the facial, and her mane and dress were still both stained.

Mercifully, she knew she at least had a shawl that she could use to cover up the worst of that.

"Happy?" She asked Filthy with a tremor in her voice.

He walked around her, then nipped at her neck possessively.

"You'll be a fine thing to remind myself who runs this town during the councileeting tomorrow," he grinned at her. "That should cover fhe first hundred. Take care, Miss Cheerilee! If you do ever feel like being stupid enough to get fired, I'm sure I can find a few positions for you to try out."

After that, he left, leaving Cheerilee to wonder who else in town he had over a barrel. It wasn't the first time she'd wondered, and she even had a few specific ideas in mind. All he knew for sure was that the Apples weren't on the list. He wasn't that stupid.

Unlike you, who are precisely that stupid, she thought to herself, looking into the mirror in her cupboard next to her shawl.

She cringed as she tied the cloth on, feeling Filthy's cooling seed smear into her. When she walked home, it was by the long route, avoiding the marketplace where other ponies would be more likely to smell sex all over her.

It gave her time to think. Despute what she'd said to Filthy, she knew she'd get away with this. She'd gotten away with it for years, after all. She'd need to take a longer shower than usual to clean herself off, get a load of laundry started… but that would be easy. Mary - Mayor Mare - wouldn’t be home until late with a council meeting tomorrow.

When she was, she'd be too tired to do anything more than eat, maybe snuggle while Cheerilee finalized her lesson plans, and then pass out in the same bed after splitting a bottle of wine.

It had been so hard at first. Not saying exactly how she'd gotten a few extra bits here and there. Lying about a "teacher's discount" at Barnyard Bargains. Exaining her limp after Filthy had railed her ass for the first time one winter by saying she'd slipped on some ice.

And now, it was so easy. Practice… but also, she knew, she was letting Mary lose herself in her job and campaigns, so she'd have the time she needed to properly cover things up.

Cheerilee paused at a fork in the road leading home. One way, and she'd be home and cleaned up before anypony had a chance to know what was happening. The other led back towards Ponyville, it's marketplace… and town hall.

"You're the one trying to keep your marefriend in the dark."

Tonight had gotten a hundred bits shaved off her new debt. A hundred bits, out of tens of thousands it would end up adding up to, for two orgasms, risking her home, her job, and what little space she still had left.

She was selling her soul for this expansion. And even if she ever got out from under it, she knew it would just be a matter of time before she was right back in.

It wasn't worth it. It never had been, but it had been easier to lie and say it was every other year, knowing she'd be able to say it was the last time in just a few months. Then starting all over again a few months after that. This time… this time, she was looking at years. Years, or starring in dozens of stag reels for the stallion she'd already had sex with more often than her marefriend lately.

She could go down to town hall. Get Mary to come home so they could talk. Confess, and get the help she needed to figure out how to tell Filthy to go fuck himself the next time.

For what felt like an eternity, Cheerilee looked at the tower of town hall, working up the courage to go there.

And then she turned, silently, to get home while she still had time. To slink away and wash the shame off. It wasn't that she didn't trust Mary. She knew she could trust her, trust her to help figure out an alternative. Trust her to understand. Trust her to stay with her, to work through this, to find a happy ending… or at least one that they could both live with.

She could trust Mary, utterly and completely.

Just like Mary could trust her.

So Cheerilee went home, and she took her shower. As she expected, Mayor Mary Mare was home late, and then had chineighse takeout for dinner while Cheerilee finished her lesson plans for the week. They split a bottle of wine, talking about their days.

The meeting was going to be a pain, but everything would work out in the end. Yes, Cheerilee had figured out a way to raise the funds to start making the expansions the school needed. Raven was dating a new stallion from Canterlot, the classroom was surprisingly peaceful now that the CMCs were working at Twilight’s school instead. The town was going to have to adjust to having more and more non-ponies living there, and yes, updated dragon-rated fireproofing was part of the upgrade proposal, stop worrying so much.

Eventually, the two mares slipped into bed together, Cheerilee smiling softly to herself as she stroked the Mator's gray-dyed mane gently, looking for the natural pinks at the roots. Eventually, the teacher closed her eyes, stuffing down the gnawing sense of guilt inside of her.

She'd tell her. Some day. Then she could come clean, and get out of the business she'd never wanted to get into in the first place.

Some day.

But not tonight.