A Filly Named Jailbait

by 2Merr

Rating: mature
Tags: Comedy, Human, Second Person
Length: 12368

Anon's adventures in foalsitting a flirtatious filly.

Anon takes a foalsitting job, expecting easy money. But there's something… off about the filly he's in charge of.

Published 1970-01-01 00:00:00 UTC
Last updated 2017-05-03 18:45:55 UTC

First Impressions

She's doing it on purpose. She has to be.

Standing by the window in your Canterlot apartment, you watch as all the colorful ponies walk past. All but one. A tiny pink pegasus filly sits in the grass across the street, directly in front of your window view. Normally, you wouldn't think much of this; she might be waiting for her parents or something. But the way she's been acting is... off. It started out innocent enough. You would scan the crowd, and occasionally make eye contact with the filly. She would quickly look away and giggle a bit. You just chalked that up to shyness. Then things got weird. You would glance at her every few minutes, and each time she'd be in an increasingly provocative position, stretching her small form, always with the same coy smile on her face. You think she's trying to be provocative, anyway. She's too cute to give you anything more than a half-chub.

By this point, you've abandoned watching the other ponies. You can't pull your gaze away from the miniature flexipone for more than a few seconds. It's been almost half an hour, and she's currently leaning back on her front hooves with her tiny wings straight behind her. Her back is arched, and her hind legs are spread wide in a perfect split. She has her tail in her mouth, positioned carefully to hide her naughty bits from view. Not that you want to see. You may be a depraved horsefucker, but you're proud to say you still have standards, low as they may be.

I need to stop while I still can. I should be looking for a job right now, anyway.

Sighing, you close the window and make your way into the living room. You flop onto the couch and grab the newspaper from the coffee table at your feet. You don't need to pay rent because Celestia says you're technically an ambassador for the humans. The only problem is, there aren't any other humans as far as anyone knows. And no one else seems to think that's weird. Ponies are a little too accepting of weird shit. They freak out about something for a few minutes, and then it's treated as normal. A fucking goat-lizard chaos demon appeared and made it rain chocolate. The next day, they're back to doing pony shit like nothing happened. Nobody has even mentioned it since then. It's unnerving.

Flipping to the classifieds, you begin the arduous task of job-hunting in a world where one's job is determined by the tattoo on their ass. Most of the ads are price listings for junk items ponies want to get rid of. There's only a handful of 'help wanted' ads, and they're mostly manual labor for shit pay, or volunteer work for no pay at all. Fuck that.

One job catches your eye. Foalsitting. The pay is marginally worse than carrying bricks, but you won't have to move very much. Besides, it's not like you have many options at the moment.

Aren't there professional foalsitters? I'm pretty sure I saw a few cutie marks with bottles and diapers. Why would they need to put an ad in the paper?

Mentally shrugging, you jot down the address and head out.

The building is easy enough to find. Nestled between a police station and a candy store is a small restaurant called The Honey Pot. You check the address again, just to be certain.

The owner probably lives upstairs. Maybe I can get some free food out of this.

You walk through the door, a bell ringing above you to announce your arrival. The interior is spacious and almost empty. The tables are placed far apart, and the only diners are a few off-duty cops and an old couple. The couple appears to be locked in a battle of wills, trying to see who can live the longest. They're both losing.

The light blue mare behind the counter smiles at you. "You must be Anonymous the human, right?" You simply nod. "My name is Ambrosia. Welcome to The Honey Pot! What can I get for you?"

"Sorry, I'm not here to eat. I'm actually here for the foalsitting ad you put in the paper." You briefly wonder if you should have brought the newspaper with you.

"Oh, wonderful! That was fast; we placed that request only this morning," the mare says as she walks out from behind the counter. "You'll want to talk to my husband about the details. Follow me."

She leads you to the far corner of the restaurant where the cops are chatting and sipping coffee. She gently knocks off the nearest stallion's hat onto the table with a giggle. "Noble, dear, this is Anonymous. He's here to watch JB while we're out tonight."

"Already? That didn't take long," the chubby yellow pegasus laughs as he turns to face you, ignoring his hat. The name on his badge reads 'Detective N. Trapment.' It looks new, or at least very well-polished. "Nice to meet you, Anonymous. I'm Detective Noble."

You don't miss the emphasis on 'detective' or the swelling of his chest as he introduces himself.

"He just got promoted and we're going out tonight to celebrate," Ambrosia explains with barely-contained giggles.

"Congrats," you awkwardly mumble. "So, uh... who am I watching and when do I start?"

"You'll be watching our daughter, Jailbait. The restaurant closes in about an hour, so you can just wait here until she gets back from ballet practice if you want." Noble keeps talking, but you zone out as one word echoes in your head.

Jailbait? He's joking right? No one in their right mind would actually name their kid that, not even in magical horse land... That poor filly.

"Is that okay with you?" Noble finishes talking.

"Um... sorry, could you repeat that?"

"I just wanted to know if you would be okay with spending the night here. You'll be paid for the extra hours, of course. We plan on getting a hotel room and really celebrating," he says as he wiggles his eyebrows at his wife. The other three stallions start snickering.

Way too much info, dude. "Sure, I guess." Money is money, and this is still better than carrying bricks.

"Perfect! Thank you so much for this, it's been a while since we've had some time to ourselves." Ambrosia's smile looks painfully large.

"It's really no problem, I just need to grab some stuff from my apartment. I should be back in about twenty minutes," you say over your shoulder as you quickly retreat to the door. You pass by the old couple and notice they haven't moved since you entered. You aren't even sure if they're breathing.

Not my business.

"Toothbrush, toothpaste, comb, change of clothes." You cross the items off your imaginary checklist and throw them all into a small, brown man-bag. It looks like a purse, but it's a fucking man-bag. That salespony clearly had no idea what she was selling. "Okay, that's everything."

Except my dignity. That shit's back on Earth.

Now that you know the route, you make your way back to The Honey Pot at a much quicker pace. The sun is just starting to touch the horizon when you reach your destination. The bell rings again, causing Ambrosia to glance up from the pile of bits she was counting. She's still grinning. Your jaw hurts just looking at her. You notice the old couple is gone. It seems like one of them won and carried the loser out. Or they were kicked out before they could finish dying.

"Welcome back, Anonymous," Noble calls from his corner booth. The other officers are gone, leaving the restaurant empty aside from you and the owners. "Jailbait just got here a few minutes after you left. She's taking a bath right now. I'll introduce you two once she gets out."

"Oh, I have an idea," Ambrosia chimes in. "Noble, sweetie, come finish counting this while I make Anon here something to eat as thanks for helping us on such short notice."

Free meal. Fuck yes.

"Sure thing, pumpkin," Noble responds in an overly-sweet tone. The cutesy name bullshit is starting to get on your nerves.

With nothing else to do at the moment, you take a seat at the nearest table and wait for your meal. You are content to sit in silence and think about the various pony asses you've encountered. You've never gotten a good look at Celestia from behind, but you can fantasize. God damn can you fantasize.

Noble finishes counting the bits and decides to ruin your moment by sitting across from you and breaking your focus. "Well, since we've got a few minutes, I guess I can give you the rundown. Jailbait is severely allergic to wasps; she swells up like a balloon and can't breathe." He passes you a small, plastic tube. "Stick her with this if she gets stung, and then immediately take her to the hospital."

Great, I have to actually pay attention to make sure she doesn't die. Fan-fucking-tastic.

"Noted." You place the pony-EpiPen in a side pouch of your man-bag.

"Next, she likes to stay up late and sleep in. She's a responsible girl, so we've never needed to give her a set bedtime. Besides, it's summer. All the foals basically become nocturnal when school is out," he chuckles heartily. He reminds you of Santa, with his jolly demeanor and pudgy gut.

"I'm a bit of a night owl myself, so I have a feeling we'll get along just fine," you say with a smirk. It's your first semi-genuine smile since waking up.

"Good, you already have something in common!"

His smile suddenly drops. You see the warmth in his eyes drain away. It feels like the temperature in the room has dropped several degrees.

Noble leans forward. "Now listen here, son. I am a public defender of Canterlot. I have the power to put you behind bars for the rest of your life. It is my sworn duty to uphold the law above all else, but that's my little girl up there. I don't care if you're the Princess herself, if I find you treating her poorly, I will end you. Understood?"

You sit there in shocked silence as Noble stares at you. You're thankful you haven't eaten anything today, because you're pretty sure you tried to shit yourself.

Finally forming a cohesive thought, you respond in a shaky voice, "Y-yes, sir."

Noble nods once and leans back in his chair. Instantly, his demeanor flips back from angry father to goofy dad. "Don't take it personally, Anon. You'll understand if you ever have foals one day."

You laugh nervously, but before you can reply, Ambrosia walks in with a steaming plate on her back. "Dinner. Is served," she says in a dramatic voice. "I made enough for two, since Jailbait hasn't eaten yet. Enjoy!"

"That filly still isn't done washing? What, did she fall asleep in the tub?" Noble stands up and huffs. "I'm gonna go check on her," he calls over his shoulder as he walks toward the door Ambrosia just emerged from.

Ambrosia takes Noble's seat at the table and watches you expectantly. The food smells heavenly. Before your stomach has a chance to complain, you remove the cover from one of the two plates.

Fucking ponies, man. How do they all not have diabetes?

The dish in front of you is bread pudding with honey drizzled on top. Not the most healthy meal in your eyes, but ponies run on pure sugar and rainbows, so you shouldn't be surprised. It tastes as good as it smells, and you clean your plate in less than a minute.

Ambrosia laughs as you lick the honey from your fingers. "Well, If I knew you were this hungry, I would've made more!"

You briefly consider sneaking bites of the remaining dish. Kids are small, so they don't need as much food, right? Your stomach certainly thinks so.

"She'll be down in a sec," you hear Noble say as he opens the door. You get a brief glimpse of a kitchen before the door swings shut.

"What was taking her so long?" Ambrosia voices your thoughts.

"She was fixing her mane and tail. She said she had to be 'presentable for the foalsitter,'" Noble sighs. "Why can't we get her to put that much effort into looking good for her recitals?"

"Oh, you know she loves ballet too much to worry about how she looks onstage. She just wants to get out there and dance."

Noble starts to reply, but he's cut off by a loud, adorable squeak. Everyone at the table turns to look at the pegasus filly standing in the kitchen doorway. She's small, even for a filly, and she doesn't have a magical tramp stamp. Her coat is bubblegum pink and shiny from recent brushing. Her mane and tail are honey yellow, slightly darker than her dad's coat. A baby blue hairband holds back her short mane, matching her eyes. You recognize her as the same filly that was stretching in the grass near your apartment a few hours ago.

"Oh." Great opener, Shakespeare.

"Hm?" Ambrosia breaks the silence. "Do you two already know each other?"

Clearing your throat, you quickly defend yourself before Jailbait can reveal that you were watching her stretch for half an hour. You don't want to seem like a pedo when her dad's a fucking cop. "I saw her outside my apartment earlier today. I didn't know she'd be the one I'm supposed to watch."

"Is that a problem?" Noble speaks up. You can detect a hint of malice, and you really don't want to push this guy.

"No sir, no problem at all!"

Noble narrows his eyes and stares into your soul.

"Well, I suppose introductions are in order, then!" God bless you, Ambrosia. "JB, this is Mister Anonymous. He's going to be your foalsitter for tonight. You need to listen to him and be respectful, okay?"

"Yes, Mom." She appears to have gotten a boost in confidence after her initial shock at seeing you. She's now smiling at you, showing none of the shyness from before. In fact, she's... smirking?

What?

"Have fun, you two!" You turn to see Ambrosia dash out the front door; Noble is already gone.

"This is a pleasant surprise," Jailbait whispers in a seductive voice.

That is not right. Children aren't supposed to be seductive!

"I just wanted to tease you while I was getting ready for ballet practice, but now I get to play with you all night, Mister Anonymous."

What.

Instant Regret

"Alright, first things first: you have to do whatever I say, got it?" Jailbait declares. She is standing on the table to be at eye level with you in the chair. Her wings are flared wide and she's puffing out her chest fluff, probably trying to look bigger.

It's fucking adorable.

"Yeah, that's not happening. I'm the foalsitter, remember? Your parents put me in charge," you respond. You briefly wonder if you can get away with ignoring her all night. As long as she doesn't die, you're fine.

"Oh, really?" The tiny horse looks genuinely surprised for a moment, before lowering her wings back to her sides. "Okay then, I'll just tell my dad you locked me in the closet all night," she cheerfully says as she hops from the table to a chair, then down to the floor.

Noble's threat from a few minutes ago echoes in your ears, making your blood freeze. You can only sit there and watch the manipulative filly trot into the kitchen. A hundred thoughts rush through your head before you finally realize that you're fucked if you don't play along.

It's only for one night, and she has to go to sleep at some point. I can deal with taking orders from a little girl for a few hours. What's the worst that could happen?

You quickly stand up and rush to the kitchen. Throwing open the door, you see the little hellspawn sitting on the counter smirking at you.

"Would the silly human like to start over?" she says in a disgustingly sweet voice.

Now I know why they had to put an ad for a foalsitter in the newspaper. She probably did this shit to all the normal ones, and none of them wanted to come back.

"...Fine," you grumble.

"What was that? I couldn't hear you with all that insolence in the way."

"Yes, ma'am." Any self-respect you had left is crushed under a tiny pink hoof.

"Close, but not quite. You will call me 'Mistress' from now on."

"..." Are you fucking kidding me?

"Well? I'm waiting," she sniffs haughtily with her eyes closed, muzzle pointed at the ceiling.

"Yes, Mistress," you hiss through clenched teeth.

"Oh, buck yes. Say it again."

You don't like where this is going.

It's not like I have any choice. "Yes, Mistress."

Jailbait lets out a shaky breath and slowly opens her eyes, looking dazed. "Now carry me."

"What? Why?" you blurt out.

"Because I said so!" she snaps, glaring at you for daring to question your mistress.

You step up to the counter, unsure of how she wants to be carried. She raises her hooves at you, looking just like a human toddler begging for upsies with a lustful smirk. You choose to ignore that disturbing image, despite your penis's protests. You grab under the filly's front legs and place her on your left hip, wrapping your arm under her flank so she doesn't slide down. She's too small to wrap her hooves around your neck, so she settles for clinging to your shirt.

How can something so cute be so evil?

"Take me to my room, servant. The stairs are down the hall."

You don't say anything while you walk, not wanting to say 'Mistress' any more than you have to. At the top of the stairs, another hallway stretches in both directions.

"Left. First door," Jailbait yawns while snuggling into your chest.

You open the door, mentally preparing to have your eyes assaulted by girlish designs.

The room looks... surprisingly normal. Sure, the bed is pink and there's some dolls on a shelf, but that's about it. Everything else is the same dull brown wood as the rest of the building.

"Put me on the bed."

You silently comply once more, placing the tiny horse on top of the covers. This isn't so bad. I thought she'd want to stay up late, but at least she's not making me do weird shit.

"Now rub my belly."

God fucking dammit.

You sit on the bed heavily, ignoring the grunt of surprise from the filly when she bounces into the air. You catch her before she lands and set her in your lap. Placing your right hand on her stomach, you start to scratch her like a dog. The effect is instantaneous. Her left wing shoots out away from you, with her right one pushing into your stomach. Her eyes roll back and she lets out a single, shaky moan.

Jesus horsefucking Christ. She's getting turned on by this? ...I'm getting turned on by this?! What the fuck, penis?! I trusted you!

Your mind is screaming no, but your penis doesn't care. That moan, combined with the filly's twitching body rubbing against your lap, makes Anon Jr start to swell. You pray to the pony gods that she doesn't notice. She could use it as an excuse to get her dad to arrest you, anyway.

After about a minute of silent twitching, you see Jailbait's front hooves slowly reach for your hand. She starts pushing it down.

NOPE.

You nearly throw the filly into her pillows, making her squawk loudly. "Hey! What was that for?!"

"Ineedtogotothebathroom!"

You race down the hall, checking each door until you find a safe haven. Thankfully, it's only two rooms down. Slamming the door and locking it, you strip down and hop into the shower, turning the cold water on full-blast. Your balls will hate you, but your soul remains pure only moderately filthy.

"Anon?"

Your heart leaps into your throat. She's probably going to get you arrested, now.

"...Ohhhh, I see. You're freshening up, first. Good idea. I'll do the same and meet you back in my room, okay?"

The sound of hoofsteps slowly fades away, leaving a single thought in your mind.

What.

Little Sins

You stand there, letting the cold water flow over you, but your erection is completely unaffected. It's telling you to give up; you have no chance of winning.

But, penis, she's a little girl.

Your penis responds by throbbing and becoming even harder, almost painfully so.

You sick fuck. How could you do this to me?

You slowly realize this is one game you simply cannot win, because you don't even know how to play. Sighing in resignation, you turn off the water and start to towel yourself dry.

You win this round, penis. It always wins.

You feel dead inside as you shuffle down the hall, completely naked. You pause in front of Jailbait's bedroom door, hand on the knob. Anon Jr is urging you forward, tugging at his leash. The words of your late grandmother echo in your mind.

"Sometimes, you just have to let go of all control, and hope everything turns out okay."

You feel your resolve strengthen. You'll do it. You're going to fuck this filly senseless. You have to.

For Grandma.

Anon Jr is practically foaming at the mouth now, anticipating the sweet taste of forbidden fruit lying just beyond the door. Your mind at peace and your soul burning in hell, you open the door.

"Welcome back, servant. Let's pick up where we left off, shall we?" Jailbait is lying on her back, front hooves behind her head, back legs crossed chastely. Her short, yellow mane is slightly damp from her own recent shower. If you were a better man, you would turn around now and never look back, but you passed the point of no return a long time ago. You shut the door behind you.

When she finally turns her head to look at you in all your naked glory, her pink coat immediately blushes a deep red.

"...O-oh." Her momentary shock fades and is replaced by that fucking smirk. "I see you're eager to serve your mistress. Perhaps I'll allow you to cum for being such a faithful servant."

You're getting really tired of this master/servant bullshit. She's one-tenth your size, for fucks sake! When she pulls a pair of handcuffs out from behind her head, you immediately remember why you're doing this in the first place.

"Now come here and let me put these on," she commands. Your erection throbs again.

Really?! Fucking really. Of all the obscure fetishes, you choose being dominated by underage horses. I'm very disappointed in you.

Anon Jr doesn't care. He's drooling now, eagerly awaiting his release.

You walk over to bed and she motions for you to sit against the pillows, which are propped up against the headboard. Doing as instructed, you hold your wrists out, ready to get 20 to life. The first cuff goes around your left wrist, before being pulled above your head. You raise you right arm without prompt because you're a filthy degenerate. The second cuff goes through a hole in the headboard before latching onto your right arm. Your last chance of freedom is gone.

"Mmm..."  Jailbait moans while biting her lip. "You're much more compliant than my other sitters were. I like that."

I fucking knew it. Were all the other sitters arrested? Did she just let them go free? ...How the fuck have her parents not noticed anything?

The filly gently positions herself on your stomach and slowly starts to grind her hips against you. "Are you ready for your reward?" She feels your arousal throb against her flank, and her smirk returns. "I'll take that as a yes... Now beg for it."

Oh my god penis stop.

"...Please, Mistress."

"Please what?"

"Please give me my reward." You're practically ready to cum already, and that fact fills you with shame.

"Do you think you really deserve it? You're supposed to be in charge, and yet here you are. Chained to the bed of a foal. You aren't very good at your job."

"I've done everything you've asked!"

"And don't you think that's kind of pathetic?"

Anon Jr thinks it's fucking fantastic, apparently.

"But you're right, you have been a good servant. So here's your reward."

Your mistress slides down your stomach and over your shameful erection, leaving a slick trail as evidence of her own arousal. She stops at your thighs, now eye level with Anon Jr. She grabs the base of your dick with her wings and slowly moves the tip to her lips.

"Good boy," she says with a kiss. Opening wide, she sticks out her tongue and drags it from base to tip. You let out a gasp of pleasure.

"You know what? I've decided to let you be the one." Your foggy mind can't comprehend what that means, but Jailbait continues. "I'm actually a virgin, and I want you to change that, my good and faithful servant."

That pushes you over the line. Your body tenses and your eyes close. Sensing your release, Jailbait envelops your dick with her lips, expertly wrapping herself tongue around the shaft. Your cum explodes into the filly's mouth, and she eagerly swallows every drop. When you're finally spent, she slowly lets you go with a loud slurp.

"Mmm... You taste different from stallions, but it's not bad. We're gonna have to work on your stamina, though."

Your cloudy mind manages a single response.

"Yes, Mistress."

"Really? You're willing to come back next weekend?" Ambrosia looks surprised at the idea. "Not that I think it's a bad thing, it's just that every other foalsitter we've had before didn't really get along with JB. None of them want to watch her again."

"She was very well-behaved, ma'am." Out of the corner of your eye, you see the filly in question walk by, her flank swaying. "I'd love to watch her more often."

"Then it's settled!" Noble loudly declares. "You'll be our permanent foalsitter from now on. Pleasure doing business with you, Anon."

You shake Noble's extended hoof with a small smile.

"The pleasure is all mine."

The Morning After

You walk home that morning feeling confused as hell. And hungry. But mostly confused. What the fuck happened last night? You've never had that type of reaction to anything before. When you were watching Jailbait stretch yesterday morning, you barely had a reaction, and she was actively trying to tease you. But when she started to order you around, you just couldn't stop yourself from getting aroused. Even worse, what's stopping her from telling her dad? He'd believe whatever she says, regardless of the truth. You realize the truth is that you are now an unregistered sex offender.

We need to have a serious discussion, penis. This is not okay. I may like to fuck horses, but this pedo shit is *your** fault.*

Anon Jr silently agrees, willfully taking the blame and the filly that comes with it.

You reach your apartment and stumble up the stairs in a daze. Finally arriving at your room, you grab your keys-

They aren't there.

Shit.

The Honey Pot is closed on Sunday's, and you don't see a doorbell. There must be a backdoor that you missed during your short stay while you were... distracted. You walk down the alley separating the restaurant from the police station, totally not feeling guilty or scared of being arrested. After exiting the alley at a dead sprint leisurely stroll, you check the back of the building to your left. Sure enough, there's a small set of stairs leading to a yellow wooden.

This is gonna be awkward.

You raise a hand to knock, but the door opens before you can touch it. You look down and find yourself crotch to face with Detective Noble Trapment.

"Oh, Anon! Looking for these?" Noble takes your keys from his uniform pocket and tosses them up to you. "I was on my way to find you, but you came back on your own!"

"Haha, yeah... I must have left them in the bathroom when I took a shower." You can't bring yourself to look Noble in the eye. You don't trust your penis enough to not take over your body and tell the detective what his daughter's mouth feels like.

Anon Jr is offended, but he keeps his silence.

"Well, you must have made quite the impact on JB. She was practically begging me to let her take these to you by herself. I'm glad my worries about you from before were unfounded."

You clasp your hands behind your back to hide the cuff marks. "I would never hurt your daughter, sir."

"I know that now, son. I was just being a dad," he says with a warm smile. "Anyway, it was nice seeing you again, but I gotta get to the office. Have a nice day, Anon." Noble steps around you and trots over to the police station's own back door. When the door finally shuts behind him, you let out the breath you were holding.

She didn't say anything. God bless that adorable, sadistic birdhorse.

All that's left to do is get some food so your stomach will stop having a little bitchfit. You turn around and start down the steps before hearing the door open once again.

"Why hello there, Anon! I take it you're back for your keys?" Ambrosia has a tired smile on her face, still worn out from the 'celebration' with her husband. "You just missed him; he left earlier to meet you at your apartment."

"I was here for that, but I actually caught him coming out the door. I got my keys right here," you say, patting your pocket so they jingle. "I'm just off to find breakfast now."

Her eyes light up. "Oh! Why don't you come inside and I'll cook something for you? It was awfully rude of us to just let you leave so suddenly without thanking you properly. It's the least I can do, since JB seems to absolutely adore you. You know, I never figured out why she couldn't get along with the other foalsitters. The stallions we hired seemed uncomfortable, and the mares were downright scared of her. I can't image why."

"Yes... That is indeed strange," you say in monotone. "But I'm definitely not gonna turn down any more of your delicious cooking." Your stomach wouldn't let you anyway, letting out a very loud gurgle.

Ambrosia giggles a bit, still seeming tired. "Well, you certainly sound hungry. Come on in." She steps to the side, allowing you to enter a small hallway that you recognize. It's the same one connected to the kitchen, but you must have missed the door while carrying Jailbait to the staircase, which is now to your right. "JB already ate, so she's probably back upstairs." Your penis seems to sense the events of last night, twitching occasionally.

Calm the fuck down, man. You had your fun last night. Besides, her mom is right here.

Said mom guides you to a small dining room on the other side of the main kitchen. "Sit right here, handcuff, and I'll whip up some omelettes."

"What?!"

"Hm? Do you not like omelettes?"

"No, not that," you wave your hand quickly. "What did you just call me?"

"Oh! I'm sorry, does it make you uncomfortable when ponies call you handsome?" Ambrosia grins sheepishly. "I promise I don't mean anything by it."

Oh. Handsome. Okay.

Your balls slowly emerge form their hiding place in your rib cage.

"No, that's... that's fine. I just missheard you, sorry," you say with the fakest laugh on Earth. Luckily, you aren't on Earth and ponies are shit at reading body language.

"Alright then, but just to be sure, you're okay with omelettes?" Her grin is back in full force. She must be physically incapable of frowning.

"Yes, ma'am."

"Perfect! I'll only be a few minutes." She turns and walks back into the kitchen, not bothering to close the door behind her. You are very thankful for this, because it allows you to stare at her ass while she cooks.

You are a firm believer in the idea that earth pony mares have the greatest asses in the universe. Because holy shit goddamn, dat ass. Ambrosia is one of the few earth ponies you've seen in Canterlot, and she definitely embodies that idea. Anon Jr agrees, eagerly trying to get a peek for himself. You tuck him into your waistband to keep him under control.

A small cough draws your attention away from the ass of the gods. Jailbait is standing next to you, a small frown on her face. Oddly enough, Anon Jr has no reaction. Your arousal from staring at Ambrosia is actually diminishing as you look at the filly. Just like the first time you saw her, she's too cute to get you hard.

"You left without saying anything."

Did I? You think back to the fuzzy memories of this morning. You and Jailbait woke up shortly after her parents got home, which nearly caused you to have a panic attack. If they found you naked in their daughter's bed, your fingers still inside her, you would be in Tartarus or worse. You had to hide your left hand's shriveled fingers and hope they didn't notice. After the conversation about becoming her permanent foalsitter, you ran out with just a glance at the filly. Oh, I guess I did.

"Uh... Sorry about that, I kinda panicked."

"I didn't give you permission to leave."

Like flipping a switch, Anon Jr is standing at attention, ready for his orders.

God, I'm so fucking pathetic.

"Um... Sorry?"

The smol anger pone doesn't say anything at first and walks toward you slowly, her eyes narrowed.

"Disobedient servants need to be punished."

Really, penis? I shouldn't even be surprised anymore, but come on. You're better than this. No he isn't; and neither are you.

Jailbait dashes under the table as her mom emerges from the kitchen, two steaming omelettes on her back.

Uh oh.

Hot Coffee and Blue Balls

This is *not** good.*

Jailbait is nestled between your legs, trying to undo your belt with her wings. Ambrosia is completely oblivious as she sets your plate down in front of you. Fortunately, the tablecloth reaches halfway to the floor, so the filly is hidden as long as she stays quiet. You're more worried about yourself, though, because keeping a straight face is not going to be easy.

"Enjoy! I put some coffee on, so that'll be ready in a few minutes," Ambrosia sets her own plate down and starts to sit in the chair across from you before bouncing back up. "Oh, my!"

Well, that didn't last long. Thankfully, Jailbait still hasn't conquered the belt, so the situation doesn't look nearly as bad as it is.

"I didn't even ask if you like coffee." Ambrosia takes a step back toward the kitchen. "Do you want me to get you something else to drink?"

Oh. I'm not sure if it's good or bad that she hasn't noticed. "Coffee is fine. I usually make a pot for myself, but I couldn't exactly get to it without my keys," you say with an awkward laugh.

"Oh, don't worry about that! Everypony is forgetful, sometimes." She sits back down and picks up her fork and knife using the physics-defying abilities of pony hooves. You grab your own fork and start cutting into the omelette. "I hope I made enough for someone as large as you. If not, I have plenty of ingredients to make more."

While you're pretty sure you could eat another two or ten, you really want this meal to be over as quickly as possible. Jailbait finally got your belt off and is now working on the button. She must be too small to reach it with her mouth or hooves, because she's still using her wings.

"No ma'am, this is plenty." Please, just shut up and eat.

You take a large bite and find it to be even better than the bread pudding was, and much less sweet. You're very thankful that Ambrosia chose to make omelettes instead of pancakes; you have a feeling she'd cover them in chocolate and syrup, and you doubt could survive that much sugar.

Midway through your second bite, you feel a sharp pain when Jailbait kicks your left shin, making you bite your cheek. You don't need to see the filly to know she's glaring at you impatiently. She taps your crotch a few times with a wing, using a bit more force than necessary. The message is clear: pants off. You're sorely tempted to ignore her since she can't seem to do it herself, but you shudder at the potential punishment for disobeying.

Giving in like the pussy you are, you surreptitiously slide your left hand off the table and start to undo your pants. The button comes undone fairly easily, but you don't want to risk the zipper making any noise, so you hesitate a bit. A sharp pain in your other shin lets you know what Jailbait thinks of that. Her mother comes to the rescue.

"I think the coffee is done, now. How do you take yours?"

"Just a bit of sugar, please."

Ambrosia trots back to where she belongs, and you quickly use both hands to unzip your pants. Another set of tapping informs you that isn't enough.

"Pull them to your knees," Jailbait whispers. "Underwear, too."

I'm definitely gonna get caught.

Now sitting with your bare ass on the cushion, you feel the filly's wings go to work. The soft tickling sensation brings you back to full arousal in no time.

"Here you go!" Ambrosia's voice makes you jump. She sets both mugs down and slides yours across to you. You grab it with trembling hands and take a sip, ignoring the heat. You burn your tongue, but you don't care; anything to distract your mind from the wonderful, feathery grip on your cock.

"What's wrong, Anon? Did I use too much pepper in the omelette?" the oblivious mare asks with concern in her voice. You realize your face is burning red, and you're sweating a bit.

"N-no ma'am, it's fine. I just burrnnnnedmymouthonthecoffee!" Jailbait ramps up her efforts when you speak, clearly trying to make this as difficult for you as possible.

Ambrosia just laughs. "Yeah, you need to careful about that! Noble does the same thing when he drinks anything hot."

You don't respond, not trusting your voice. Instead, you take another bite and pray to the pony gods for a swift death.

Jailbait really knows what she's doing. She brings you to the edge of orgasm, and then keeps you there. When you reflexively buck into her wings, she releases her grip for a few seconds before repeating the process. You're now panting, your heartbeat pounding in your ears. You don't know what the fuck is wrong with Ambrosia, because she continues to eat, nearly finished with her plate.

You start shoveling omelette into your mouth, choking it down with more burning coffee. The oblivious mare doesn't even blink at the disgusting display. Fucking ponies, man. You swallow the mass of eggs in your mouth right as she takes her last bite. Meanwhile, Jailbait continues to stroke away at an agonizing pace, smearing your precum into her feathers.

"I'll take that for you, dear." You didn't notice Ambrosia get up, but she's now reaching for your plate and mug, looking much more awake since drinking her coffee. You place your empty mug on the plate and slide them over, unable to hide the trembling in your hands. Once again, the light blue mare remains ignorant and trots off to the kitchen with both plates on her back.

The heavenly wingjob comes to an abrupt stop. You see Jailbait peek out from under the table and glance toward the kitchen. She then turns to you with a cold stare.

"That's for leaving without permission. You may go now."

She dashes off to a side door, leaving you rock-hard and unsatisfied. You quickly pull up your pants before Ambrosia gets back, shuddering at the cloth rubbing against your sensitive member. You immediately realize what just occurred. You can't finish until you leave, and your erection will be gone by then.

You just got blue-balled by a filly.

Gathering your broken spirit, you step into the kitchen.

"Thank you for the meal, it was delicious," you mumble in a dead voice.

"It was my pleasure, Anon!" You wish it was yours.

"See you next week, Mrs. Ambrosia." You start to drag your feet down the hallway leading to the exit.

"Bye, Anon! Have a nice day!"

The walk home is uneventful, but you can already feel the pain starting to gather in your groin. When you finally reach your apartment, the single pony inside gives you a strange look as you slowly waddle to your room.

Young and Impure

You are standing a few feet inside your apartment, trying to move without disturbing your tender jewels. Your shirt was covered in sweat, so you took it off before unlocking your door. Now, you just need to figure out how to remove your pants as efficiently and painlessly as possible. You start with the belt, which proves to be just as much of a pushover as its owner. When you grab the button, though, you notice something out of place.

A small, pink feather is tucked into the waistline of your pants, slightly ruffled from the walk home. You gingerly remove it and start to smooth out the barbs with your fingers. It's a few inches long and looks to be one of Jailbait's primary feathers. You place it on the coffee table and continue struggling against your pants. After a few long, painful minutes, you stand naked and victorious. You double check to make sure you locked the door behind you, then awkwardly waddle to the bathroom.

You turn on the shower and step in once it's warm enough. This shower serves two purposes; an attempt at cleansing your sinful body, and a safe place to furiously touch yourself. The best cure for blue balls is to orgasm as soon as possible, and that's exactly what you plan to do. You set a personal record and manage to finish in under a minute. And regardless of what Anon Jr says, you most certainly were not thinking about an underage horse riding you like a rodeo bull.

I'm so fucking pathetic. It has become your daily mantra; a reminder of just how little you deserve to live.

The relief isn't immediate, but it slowly fades as your erection wilts. Finishing up with your shower, you step out and grab one of the many towels you stole from the palace during your first week in Equestria. Sneaking them out was extremely easy; no one noticed you weren't actually pregnant. They just gave your stomach a strange look and then sighed. Ponies can be so stupid.

When you're completely dry, you slap on a new pair of boxers and take a seat at your favorite window. It's Sunday, so there are more ponies out than usual. You glance at the patch of grass where you first saw Jailbait stretching, but she's obviously not there. Her ballet classes are in the evening, if you remember correctly. Aside from Saturdays, you don't even know what days the classes are on.

You catch yourself wondering about the schedule of a children's dance class.

Have I truly fallen beyond morality and shame?

You realize that you no longer care.

The week passes quickly with little event. You don't see Jailbait again until Saturday evening, when she finally returns to her spot in the grass, escorted by her father. Noble says a few words to her, then starts walking back. She starts to stretch, but then glances up at your window. Seeing you there watching, she motions you down with a hoof, the shy smile making its reappearance.

You casually sprint down the stairs and out the door, nearly running over several ponies in the process. Stopping at the bench next to Jailbait, you try catch your breath while she laughs at your eagerness.

"Um... Anon?"

You immediately notice something off. Jailbait has never used your nickname before. It's always been 'servant' or 'human' except for the one time she sarcastically called you 'Mister Anonymous' when she first spoke to you. Looking up with trepidation, you are surprised to see the filly looking... nervous? That can't be right.

"Yes, Mistress?" You glance around after replying, worried someone nearby might have overheard.

"N-no, you can drop... that, for now. I just... I was w-wondering if you wanted to come watch me dance..." she quietly trails off at the end, making you strain to hear. Your brain takes a few seconds to process what the fuck is going on.

"Y-you don't have to!" Jailbait quickly says before you can respond. "I mean, I just wanted to let you know, and if you have any free time you can..." she's mumbling unintelligibly now. Your brain hasn't quite caught up yet, probably because you're a fucking moron.

Jailbait takes your silence as an answer, and she starts to ramble in a voice slightly louder than a whisper. "I-I know, it was stupid. I shouldn't have even asked. You probably don't even-"

"I'd love to," you blurt as you finally succeed in rubbing two brain cells together.

The filly just stares up at you, her mouth slightly open.

"...Really?"

There's definitely something going on here. I just wish I knew what.

"Yeah, it sounds fun." You nod your head with a smile. Her face lights up.

"Okay!" She grabs your hand with her wings and starts pulling you toward the building next to your apartment. "I'll introduce you to my, friends, and you can meet my teacher, Miss Frills!" You let yourself be pulled along, happy to see Jailbait so excited for once, but wary at the same time.

The building looks nothing like a dance studio on the outside. It's a small, yellow box with a single, wooden door facing the street. The only windows are near the roof, preventing you from seeing inside. When you're dragged through the door, your vision is temporarily restricted by the dim lighting.

Jailbait pauses when she sees the darkness, not releasing her grip on your hand.

"Huh? Where is... wait," she whispers to herself before turning to you with a sheepish smile. "Uh, I forgot I'm always the first one here. I usually wait for Miss Frills to arrive before going inside, but she's not here, yet."

"Should we go back outside?" you suggest, gesturing toward the door with your free hand.

"...Sorry," Jailbait mumbles before turning to the door.

Right as you close the door behind you, a sharp voice makes you jump.

"What were you doing in there?"

You turn to see a jet-black earth pony mare glaring up at you. Her white mane is pulled up in a tight bun, giving her a very professional look. You notice her ass tattoo is actually an ass tutu—a white silhouette of the hind legs of a pony wearing a frilly ring just above its flanks.

"Miss Frills!" the filly behind you pipes up, releasing your hand to give the mare a hug. "This is my foalsitter, Anon. Is it okay if he watches us today?" Her voice is overflowing with excitement, making you smile once more.

"I don't see why not, but why were you two in there?" She doesn't even glance at you.

"I... I wanted to introduced him to everypony, but I didn't realize how early it was," Jailbait laughs nervously with her ears splayed back.

"Hmph. Well, no matter. I'm here now, so we can go inside. Nice to meet you, Mister Anon," the mare walks past you into the building, still refusing to look at you.

"The pleasure is all mine," you mutter, watching her flank sway as she walks. Chalk one more point to earth ponies having the best asses.

You sit in a chair next to a rubber mat that stretches across nearly the entire floor. All the foals have arrived and are sitting on the mat in front of Miss Frills. To your surprise, you see a few colts in the group. Most of them are staring at you in wonder, while the rest seem a bit afraid of you. Jailbait is bouncing in place, eager to finally introduce you to her friends.

"Alright, young ones," Miss Frills says in a much softer voice than previously. "You have undoubtedly noticed our guest by now, so JB here will introduce him to you all." Jailbait jumps to her feet and dashes to your side, grabbing your hand with her wing again. She pulls you to your feet  and over to the spot where her instructor previously stood. The foals don't seem afraid of you now that Jailbait is next to you, still bouncing and grinning.

"Everypony, this is Anon. He's my foalsitter," the pink filly proudly declares. The group lets out a few 'oohs' and 'aahs' in response. "He's here to watch me dance. It's okay to be jealous, I don't blame you." There's the cocky attitude. What happened before?

"Also," she continues before glancing at you. When she makes eye contact, her body stiffens and her confidence drains away. She turns back to the small crowd. "He's... uhh... Y-you can look at him, but don't touch!" she practically yells that last line, her face growing red. You notice her legs are shaking. What the actual fuck? Is she sick?

Miss Frills seems to notice as well, because she quickly speaks up. "Thank you, JB. Alright everypony, find a partner and begin stretching. We only have one more week until the recital, so let's work extra hard today!"

You watch in confusion as Jailbait grabs the nearest pony—a blue unicorn filly—and drags them to the opposite side of the room. All the other foals quickly find partners and begin their stretches. Miss Frills watches in silence before turning to you.

"May I speak with you for a moment?" she asks in the harshest polite tone you've ever heard. Who pissed in her cornflakes?

Not waiting for a response, she walks off to a small office at the back of the room. Following behind her, you take the opportunity to continue staring at dat ass.

The dark mare closes the door behind you and you hear a lock click.

"What the buck did you do to her?"

...I'm going to prison.

Pure Evil

Miss Frills has her back to the door, head low and nostrils flared wide. She looks about ready to kill you. Oddly enough, you remain calm. You initially accepted your fate, but then logic smacked you in the face: there's no way she knows. Jailbait hasn't seen her in a week. Besides, if she wanted you arrested, she could just tell her father. This is just a teacher overreacting about her student's strange behavior. Probably.

"Answer me!"

You raise your hands in a placating manner. "Can you please explain what you mean? I haven't done anything to anyone, as far as I know."

She narrows her eyes at you. "JB is one of the sweetest little angels in my class. She's confident, charismatic, and friendly to everypony." You try not to scoff. "I have never seen behave like that before. She looks like she's about to faint from embarrassment, but she hasn't done anything to be embarrassed about. Hay, I'm not even sure that filly is capable of feeling embarrassed. She only started acting that way when she looked at you, as if you did something. So, I want answers. What did you do to her?"

"I haven't done anything! She can tell you that herself. In fact, bring her in and ask her why she's acting so weird, because I'd like to know, too. It's the first time I've seen her like this."

She snorts. "Fine. I know the Princesses have said good things about you, but if I find out something's wrong..." She let's the threat hang in the air. You aren't bothered. You had to deal with Noble's version of that, and he's much better at it.

The ebony mare turns and unlocks the door, opening it just wide enough to poke her head out. You are blessed with a third opportunity to gaze upon her immaculately toned flank. Oh, the things you would do to that ass if you weren't being blackmailed by Satan's favorite helper. You can imagine your hand wrapped in that white tail; her mane falling out of its tight bun as she tries to stay upright, her legs shaking in pleasure. Down, penis. Now's not the time.

"JB, sweetie, can you come here for a sec? You're not in trouble, I promise."

A few seconds later, the pink little nightmare walks in and glances at you. She sits in the chair in front of the desk and gives a small sigh. She looks... disappointed?

"That didn't last very long," you hear her mutter under her breath.

Miss Frills takes the seat behind her desk, leaving you standing next to her in confusion. What didn't last long?

"JB, I noticed you were acting... strange earlier. Did something happen?" The mare leans forward with a concerned look on her face.

Jailbait stares forward, her gaze unfocused. She starts to speak in a droning voice, as if reading from a script.

"I am fine, Miss Frills. I was just nervous that my friends would not like Anon because he is a human."

Miss Frills perks up immediately. "Oh! Well I wouldn't worry about that. They all seemed rather intrigued once you introduced him."

She actually bought that? Fucking ponies, man.

"Uh-huh," the filly responds in a bored tone.

"Well, that settles that! Let's get back to class," Miss Frills says as she trots out the door. "Sorry about the confusion, Anon." She doesn't look sorry.

You start to follow those glorious cheeks when you feel a tugging on your leg. You look down to see Jailbait spit out your pants leg and glare up at you.

"Why can't you be more fun?" she complains with a grumpy little pout.

"Wait, what? What's that supposed to mean?"

"You were supposed to crack under the pressure and confess your perverted actions, and then I would deny it all and make you look like a lunatic."

"You... you were acting? The whole time?" You can't believe it. She's not content with just blackmailing you, she's trying to destroy your reputation. "But... why?"

"I saw the way you were staring at my mom and Miss Frills." she says while inspecting a hoof. "If everypony thinks you're a creep, then I'll be the only one you can turn to." She slams her hoof on the floor and growls. "You belong to me. You don't need any other mares."

"B-but... booty," you whimper.

She kicks your shin. Hard.

"If I catch you staring at anypony else, you can say goodbye to these." She prods your nuts with a wing. "Got it?!"

She doesn't wait for a response and trots back to her class, leaving you alone in the office.

Something in you snaps. It's one thing to threaten your reputation, but when you're told you can't look at pony poopers anymore, a line has been crossed. She can take your body, she can take your balls, but she will never take your ass-worship away from you.

Anon Jr thinks you're being over-dramatic, but he's just being a dick.

I need to put a stop to this. Somehow.

Your grandma's advice floats into your mind: "If you ever find yourself in a situation where a sweet piece of ass is on the line, you must fight dirty, Anon. There is no cause more worthy than that."

Grandma was so wise. But this isn't about just one ass; this is about every piece of ass in Equestria.

It's time to finally stand up for yourself.

Everything is Fine

You sit in a chair, staring into nothingness. The foals are lined up along a rail in front of a wide mirror on the opposite wall. Your brain is working harder than ever before, trying to figure out a way to expose Jailbait's actions without making you look like a criminal. Unfortunately, you aren't very smart, so the class ends before you can come up with anything.

A pink and blonde blur enters your vision, and you blink to focus your eyes. Jailbait is standing in front of you, smiling happily.

"Good job, servant. You didn't look at Miss Frills a single time. I'm happy to see you being so obedient. Perhaps I should reward you tonight, hm?" Her smile turns into a smirk. "Maybe I'll let you cum this time."

Her words spark a thought in your brain. Tonight. You're going to be watching her tonight while her parents are out. This is the best opportunity to put your plan into action.

The only problem is... you don't have a plan.

You can't just tell Noble "Hey, your sadistic daughter is going to chain me to her bed tonight and use me as a fuck toy while she says mean things that hurt my feelings and make my peepee hard for some reason. You should come watch." That wouldn't work... Right?

Your musings are interrupted by Jailbait hopping into your lap. "Dad usually picks me up when he gets off work, but you can take me home now since you'll be over tonight anyway." She latches onto your shirt and ruffles her wings. "Let's go."

Wrapping an arm around the filly, you stand up to leave while the various foals wave goodbye at the both of you. As you pass in front of your apartment, you realize you need to grab your not-a-purse and your overnight stuff from your room. Jailbait makes no comment on the detour, but she does snoop around in your dresser while you pack. When you're ready to leave, you grab the blank flank sticking out of the bottom drawer and place her on your shoulders.

"Ooh, I like it up here," she purrs, clamping her thighs around you. She's too small for it to hurt, but you can now feel her marehood rubbing against your neck as she starts to grind her hips. "Hurry up! The sooner we get home, the sooner my parents can leave." You feel her shift a bit before she leans forward. "We're going all the way tonight," she breathes into your ear.

You know this should bother you, but it doesn't. The first night of debauchery consisted of Jailbait blowing your mind and busting your nuts with her tongue, followed by you alternating between rubbing her belly and fingering her. It didn't go any further, but she did say she was a virgin, and that she wanted to change that. With you. Once that happens, your soul will be tarnished forever; branded as a foalfucker. The foreplay stuff was bad, but this is unforgivable. And you aren't bothered by that. Maybe you've grown numb.

Your penis disagrees, already half-mast from the feeling of filly bits on your neck.

You've been running on autopilot while lost in thought, so you're surprised to find yourself standing just outside The Honey Pot. The bell chimes as you open the door, still feeling like your mind is in a haze. You glance around, but no one is inside. They must have closed early. The kitchen door is open, and you hear voices coming from inside.

"Bye, sweetums, I'm off to pick up JB," Noble says as he walks through the doorway. He pauses upon seeing you and glances up at Jailbait situated on your shoulders. "Nevermind, Anon brought her! He's such a good lad, isn't he?"

"Really? He's even earlier than last week!" Ambrosia calls from out of sight. "I wonder why that is?"

"Now, let's not look a gift horse in the mouth." You wonder how that phrase even exists in this world. "He's here now, so that means we can leave early!" Noble rushes back into the kitchen and you hear the sound of pots and pans clanging together. "You can do those when we get back, let's go!"

The couple zips past you and out the main door before you can even consider stopping them. It doesn't matter. You wouldn't have been able to say anything to them; not with Jailbait right on top of you.

The filly strokes your ears with her wingtips before hopping off and fluttering to the ground. "I'm going to take a bath. You can use the one upstairs again. We'll meet back in my room, okay?" Like always, she doesn't wait for an answer and trots off, leaving you alone with your thoughts.

You sluggishly drag your feet through the kitchen, down the first hall, up the stairs, down the second hall, and into the bathroom. You lean over the sink and just stare at yourself in the mirror. Your eyes are bright with energy you don't want. Your mouth is threatening to curve into a smile you shouldn't have. Why aren't you upset? You should be worried, or angry, or... or something! But you aren't. All you feel is... aroused.

Maybe... maybe I should enjoy myself. Just this one time, maybe I should let go of my worry and stress... and just fuck her. Then, I'll figure out how to put a stop to it. Eventually.

Your chest feels lighter, and the smile makes its full appearance. You strip down and hop into the shower. You step out looking clean, but you feel more dirty than you've ever been in your life.

And you don't care.

Dark Side of the Poon

You find yourself sitting on the edge of Jailbait's bed, waiting for the filly to finish her shower. Your clothes are in a small pile next to the door; you won't need them. Your heart is pounding with anticipation, but your mind is calm. You know what you want, and you know it's coming soon. You tried searching for the handcuffs, but they were nowhere to be found. You were hoping to hide them so you could retain some freedom for your hands; mostly to grab that tiny little ass while she's bouncing on you. Maybe pick her up like a living sex doll and just pound away... No. She wouldn't let you do that.

You hear muffled hoofsteps approaching the room. Jailbait stops at the edge of the doorway, only her head visible to you. "Anon, I have a surprise for you," she sings. The filly steps fully into view and your heart stops for a few beats. She's wearing what you can only assume is her ballet outfit, but without the skirt. It's a light blue leotard made of a tight-fitting, silky material hugging her from neck to tail. The rear of the outfit is made to only cover the back and stomach, showing off her lack of a cutie mark. Because of this, the part covering her ass is very skinny, only held in place by her tail sticking through a specially-made slot. There are small pads under the wing slots, making them puff out slightly. Her legs are covered by a pair of silky white socks that reach just above her knees.

"You've been a very good boy, Anon. This is your reward." She hops onto the bed next to you and places a hoof on your stomach, urging you backwards until you're leaning against the headboard with your legs straight out. She crawls into your lap and sits with her wings against your erection. She looks up at you with half-lidded eyes and whispers, "If you promise to behave yourself, I'll let you keep the cuffs off."

You nod mutely, stunned in the best possible way.

"Good boy," she coos in a sultry tone.

You gently wrap one hand around her left leg, dragging it over your thigh before doing the same with the other side. Her legs are now spread wide, revealing a shiny patch where her arousal is showing through. You place both hands on her stomach and start gently stroking up and down; you know she likes to go slow. She lets out a contented hum and wraps her tail around your right leg. Your fingers softly trace circles, ever-so-slowly working their way lower until they eventually encounter dampness. You slide your left hand back up to her stomach and start to lightly scratch there while your right hand massages her marehood through the material. Jailbait signals her approval with a low, throaty moan. You consider playing with her wings, too, but that idea is quickly dismissed. Her wings are so small, it'd be like trying to fondle a ten-year-old's breasts. You can try, but it won't accomplish much besides revealing your ignorance of how pegasus wings work.

Thinking about breasts gives you an idea. You slip your left hand under the leotard to attack her nipples on her lower stomach. You feel around like a blind man reading Braille before finding your target. Gently tweaking one of the tiny nubs causes the filly to gasp and her body to stiffen in pleasure. You start to slip your right hand under as well before being stopped by a trembling hoof.

"I think that's enough," Jailbait slurs, her eyes unfocused and a dopey smile on her face. "No cuffs for you."

She slowly stands on shaky legs, making sure not to step on anything important. Turning to face you, she puts her front hooves on your stomach and leans her minuscule weight on you. She's panting now, a heavy blush showing through her pink fur.

"H-help me put it in," she whispers into your chest. You knew she was small, but it didn't really register until seeing her in this situation. You've always wanted to fuck a girl until she couldn't walk, but not like this. This might actually hurt her.

Your hesitation causes Jailbait to glance up, restlessness showing on her face. "Anon, p-please... Fuck me."

Well, she did say please.

Ignoring safety concerns as well as the law, you hook a thumb into the soaked cloth between her legs and pull it to the side, marveling at how wet she is. A small whimper snaps you out of your staring. You grab the base of your cock and position yourself directly beneath the glistening folds. Jailbait waits until she feels you pressing against her entrance before she starts to lower herself down. You clench your teeth as your head slowly slips in. She's extremely tight, almost painfully so. The filly pauses with just the tip inside. She's gasping for air and you can feel her trembling. You want to ask if she's okay, if she wants to st-

Her legs give out and she drops straight down, gasping as she takes every inch of your cock deep inside of her in one swift motion. Her eyes squeeze shut and you freeze, not wanting to cause any further pain. She's holding her breath, tears leaking out of her eyes. You're trying not to move, but the feeling of bottoming out in the tightest pussy you've ever felt is making your hips twitch in ecstasy. It doesn't help that the pain is making her clamp down on you even harder.

It feels like hours before Jailbait lets out her breath in an explosive sigh. She wipes away most of her tears with one hoof, the other pushing into your stomach to lessen some of the pressure. When she finally looks up at you, you're surprised to see a smile, albeit a strained one.

"Okay, you can move now," she says in a shaky voice, now with both hooves on your stomach.

You grab the filly by the flank and slowly lift her up, pulling out until just the tip remains once more. Jailbait gives a sigh as the pressure disappears. You spend a few minutes gently repeating the action, letting her get adjusted to your size. Eventually, you stop when you see her start to cry again.

"I-I'm sorry, I can't do it. It hurts too much," she sniffles. She lifts herself off of you, your dick making a wet smack as it pulls free and hits your stomach, right between her hooves. You see a bit of blood mixed in with the fluids. She collapses back down, this time on your chest, and she starts sobbing.

"I'm sorry, I'm so sorry, "she wails between breaths. "I didn't think it would hurt that much. I'm sorry."

You just wrap your arms around her and bring her closer; she's curled into a ball now.

"Nonono, don't apologize," you try to comfort her. "It's not your fault. That's normal, actually. Especially since I'm so big." Anon Jr swells with pride, thinking you're talking about him.

A minute passes in silence before she calms down enough to speak again. "I knew it would hurt, but I thought I would get used to it..."  she mumbles into your shoulder. At least the tears stopped.

"No, it'll take a lot longer than a few minutes to stretch out enough until it stops hurting," you say with a small laugh.

You feel her snort. "We're just gonna have to keep trying, then."

It looks like she's back to her normal, arrogant self now that she's not crying in pain or half-blind with arousal.

"And the cuffs are going on next time."

Well, shit. You just sigh.

"Now carry me to the shower. You're going to learn how to wash me because I can't move right now, thanks to you."

You stand up from the bed with the filly in your arms and start walking to the door. "Yes, Mistress," you say under your breath.

"...Anon?"

"Hm?"

"You can just call me JB," she says softly, nuzzling into your neck.

Maybe things aren't so bad, after all.

Of Ponies and Pedos (Alternate Ending)

It feels like hours before Jailbait lets out her breath in an explosive sigh. She wipes away most of her tears with one hoof, the other pushing into your stomach to lessen some of the pressure. When she finally looks up at you, you're surprised to see a smile, albeit a strained one.

"Okay, you can move now," she says in a shaky voice, now with both hooves on your stomach.

Right as you grab her flank, a loud bang from downstairs causes both of you to freeze. You lock eyes with Jailbait, neither of you breathing.

"Are your parents back early?" you whisper fearfully. Your heart is pounding in your penis, making you experience a strange blend of panic and ecstasy.

"No. At least, they shouldn't be..."

"JB? We heard a noise, are you alright?" an unfamiliar voice calls faintly.

"Oh, no, it's Miss Karma! She's one of the police ponies," Jailbait whispers fearfully.

You hear the sound of hoofsteps coming up the stairs. You look at the crying filly impaled on your dick; she's bleeding a bit onto your thighs.

This doesn't look that bad. I can just explain that I was blackmailed into it, and everything will be fine.

The door flies open, and a green unicorn mare rushes in.

"SHE MADE ME DO THIS!" you calmly explain. "I HAD NO CHOICE! I HAD TO FUCK HER!"

The officer stares at you in horror. Her horn lights up and you feel Jailbait yanked off your dick.

"You sick bastard! How could you do this!"

Clearly, she's misinterpreting the situation. You try a different approach.

"I DIDN'T DO ANYTHING, IT WAS HER! SHE WAS BEGGING ME TO FUCK HER! LOOK AT WHAT SHE'S WEARING, FOR FUCK'S SAKE!"

There. That should prove your innocence. Why else would a filly be wearing a tutu unless she was trying to get you to fuck her?

"Go to Tartarus, creep!" Her horn lights up and a bright bolt hits you in the chest. You collapse to the floor, writhing in pain.

"THIS IS POLICE BRUTALITY!" you shriek between surges of pure agony. A final burst of light, and your consciousness fades.

Gray. It's all gray. Four gray walls and a gray steel door. You've forgotten what other colors look like.

A hoof pounds on your door. It slowly squeals open, revealing a gray pegasus in a gray uniform. It's all gray.

"Alright, sicko. It's time for you to go."

You blink. You must have misheard. It almost sounded like you were-

"Come on, Anon. Let's get you out of there." A strangely colored unicorn steps into view.

What color is that? You think it's brown, but you can't tell. It's all been gray for so long.

"Wait, am I... free?" you breathe quietly, not daring to hope.

"No, actua-"

"It's been eighty-three years," you say as you fall to your knees, tears streaming down your face.

The unicorn sighs. "Anon, I left less than an hour ago. Come on,  your trial is up next."

A trial. After so long, you get a trial. You get a chance to defend yourself.

"It was her," you mumble, following behind him. "She made me do it."

"Mhm."

"Did you see what she was wearing?"

"Yes, Anon, I saw."

"I'm gonna be let free, right? It's been so long..."

The unicorn pauses in front of you and turns around. "Anon..."

"Eighty-three years..."

Appointed Lawyer snorts and continues leading the human to the courtroom. The sooner the filthy pedophile is behind bars, the sooner Appointed can enjoy some of that cake in the break room.