A Filly Named Jailbait

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.