Keeping Eyes off Babs's Booty

by darf

Rating: mature
Tags: My Little Pony: Friendship is Magic, Human, Other, Romance, Apple Bloom, Sex, Babs Seed
Length: 8602

Human-in-Equestria babysits Babs and Applebloom, WITH SEXY RESULTS.

After being stuck in Equestria for any amount of time, it's normal for a human to go stir crazy. Does that mean that staring at Babs's filly-booty is in any way moral? Don't think too hard about that question--especially if Babs doesn't want to think about it either.

A bootyful filly fun-fest, commissioned by Anonymous.

Published 2016-05-15 19:40:02 UTC
Last updated 2016-05-15 19:40:02 UTC

The Only Chapter (Filly-Butt-Fun)

There is (according to Twilight, anyway, last time I asked her) a long history of humans and Equestrians getting along. Apparently in pony pre-history, a girl named Megan coexisted with ponies and helped them with their struggles and general friendship related activities. There’ve been dimensional travellers thrown up by the void to find some kind of home amongst miniature talking horses. There have been ‘incidents’, and arguments about informed consent. Tongues have burned.

I, personally, have been here about three and a half months, and it’s been almost too easy to find ways to make myself useful. It seems like everywhere I go, everypony I talk to, something needs fixing or adjusting or tuning, and oh please big mister human, couldn’t you please help? I have no idea whether the humans before me had to fend off interspecies flirting as well. A handyman job always turns into a waving tail and flirty eyebrows. Do ponies just have a thing for humans? Is cross-species romance not really a big deal here? There’s been dragon and pony precedent, certainly, but I have yet to see a biped and a pony go on a date together. Not that Twilight’s ass doesn’t look awfully inviting when she’s searching her bookshelves for something hard to find.

Today, the job is a double: fix up a leaky shed roof for Applejack in the morning, then spend the night watching her kid sister and cousin while she and Big Macintosh head off to the Big Apple for an agriculture convention. Applejack is probably my favorite pony to do work for, because it seems like she appreciates the actual value of something done right—plus, she has the best non-human butt I’ve ever laid eyes on, and either doesn’t mind my staring, or is completely oblivious to it. While leaning over the fence and waving her tail in the air. For three minutes at a time. Winking.

Anyway.

It was around four PM when I got to the Apple Family Farm to find Big Macintosh and Applejack waiting for me at the bottom of the long dirt driveway, smiles on both their faces.

“Sorry I’m a bit late,” I said, waving to the two ponies. “Took a little while to find all the tools I needed.”

“Shucks, don’t worry about it.” Applejack gave me a pat on the back (pony hooves are conspicuously soft). “We figured you’d have enough on your hooves—er, hands—looking after the girls that we could take care of the shed roof ourselves.”

“You did?” Suddenly the belt of tools I’d warn over looked like an incredibly out-of-place fashion accessory.

“Eeyup.” Big Mac gave a nod in my direction, then another over at the shed roof, which I could see had been plainly patched and would presumably remain bone-dry in event of rain.

Even though I hadn’t particularly looked forward to doing the work, there is a little something about feeling useful—and to have something to occupy my mind besides the fillies I was supposed to be watching for the next twenty-four hours, give or take. I’d foal-sat for Rarity before, and as nice as Sweetie Belle is, she’s a real handful when her sister is gone, because suddenly everything becomes permitted, and the human watching after her is the one to take all the responsibility for where the fabrics went and why the dresses were out of order and why Sweetie Belle had been found in the bathroom wearing lingerie and makeup while I was sleeping in the back yard. Look, a day of watching a young pony really takes it out of a guy, alright?

“Oh… well, that’s something, I guess. So you just need me to look after Applebloom and…”

“Applebloom and her cousin, Babs Seed. She’s visiting all the way from Manehatten, and the two don’t get to see each other too often—so we really appreciate you helpin’ us out. The convention date changing sure threw us for a loop.”

“Eeyup.”

As we made our way to the end of the driveway, I took a second to appreciate how nice the Apple family homestead looked; all-in-all, the house was a very impressive structure built up by just a few ponies, and it managed to look inviting and imposing all at the same time. A shade of red brighter than red, almost.

“The girls are upstairs right now, but I’ll call ‘em down to meet cha’ before we go.” Applejack pushed open the front door and turned to the stairs towards the upstairs bedrooms. “Applebloom, Babs, we’re leavin’! Come down and say hello to your sitter.”

It wasn’t like I hadn’t meant Applebloom before—practically every pony in town knew me now, the only upright bi-pedal pink monkey-thing around—but Babs would be a new face, and hopefully a bit more cooperative than Sweetie Belle had been. Applebloom, on the other hand, was almost always perfectly polite, albeit a little mischievous. At that age, still hoping for her cutie mark, it’s hard not to be curious about everything.

Two sets of smallish hoof-steps clattered down the stairs, and Applebloom and her cousin Babs made their appearance.

“Hey there,” Applebloom said, wearing her usual ‘friendly to everyone’ smile.

“You already know Applebloom,” Applejack said, nodding in her direction. “And this is Babs Seed, our cousin from the Big City.”

“Hey,” Babs said, looking up at me with mild disinterest before returning her eyes to the ground. Manehatten glowed off her—the low, gravelly accent, along with a physique that suggested more by-the-slice pizza than lettuce salads—and, lest my eyes spare me a place in hell, a curve to her backside that looked like a jean-short ad waiting to happen. I swallowed a sudden lump in my throat and tried to remind myself that some curves, while still just curves, were much more illegal than others.

“We ain’t got a lot of time before our coach, so we gotta jet—but y’all know where the blankets and pillows are, and there’s some left-over stew in the fridge for dinner. You two behave while we’re gone!” Applejack gave her little sister and younger cousin both a pat on the head and a kiss on the cheek before turning smartly and walking out the door. Big Mac followed, giving his own hugs but staying in his usual silence. The door swung with a slight creek behind them on its hinges, leaving the house empty except for the two young fillies and me, their inter-species babysitter.

Without my even noticing, the girls had gone up the stairs and back to their bedroom. I don’t blame them—making small-talk with a babysitter isn’t among the greater pleasures of life. But are they going to ignore me all evening? Hopefully they’re not planning some kind of mutiny.

Sighing, I pulled out a chair from the dinner table and fell backwards into it, noting the stiffness of the wood against my back. Maybe because ponies are so soft, their furniture doesn’t need to be? I picked up a green apple from a bowl on the table and took a large bite. I’ve never tasted apples like the ones on the Apple Family farm before—the combination of bitter-sour and sweet was just right. And so, without anything else to do, I settled in for an evening of apple-munching.

***

It only took half an hour for the girls to come back downstairs and find me in the living room. Applebloom didn’t say anything on her way down the stairs, but Babs followed behind with loud steps and a louder mouth.

“I’m boooooooored,” she said, Manehatten accent taking over her ‘r’s. “Let’s do something.”

Applebloom’s eyes perked, and her mouth moved as tho to open, but closed again just as quick, her eyes swallowing what she’d meant to say. “I thought…” and there it went again, the thot swallowed.

“Do you guys have any board-games or something?” I asked, turning in my chair pointlessly, finding the same fireplace and coffee table that had been there for the last half hour. No Monopony as far as the eye could see.

“Ooh, I’ve got a deck of cards! It’s missing the Aces, but we could still play Go Fish, or Rummy, or…” Applebloom’s voice trailed off at Bab’s stare, a “how-old-are-you?” that cut with a familiar condescention.

“Back home we play hoofball after school. Do ya have a court anywhere nearby?” Babs asked.

“Actually, yeah! My sister built one a few years ago, when she and Rainbow Dash were watching the league and wanted to have a one on one shoot-out…”

“Great!” Babs smiled, which turned into a smirk, which I couldn’t help but feel had just slightly more ‘come hither’ in it than any smirk I remember seeing back in human-land—but as soon as I saw it, it was gone, and Babs was a cute little filly again, wanting to play two-on-one hoofball with her cousin and the lanky pink monkey babysitting her.

“You guys think you can beat me? I don’t have hooves, but I imagine hands are probably close enough to count.”

“Two versus one?” Babs asked, smirk returning (including, no matter how hard I fought them back, my accompanying thots about pony/human intimate relations and whether Babs’s mouth was as soft as it actually looked). “I think we’ll beat the pants off you.”

Better that Babs doesn’t know uncomfortable pants are in the first place—if I was to suddenly stop wearing them, would Equestria care? Or could I take full advantage of my instant access, and treat the world of cute ponies and their squishy bodies as a smorgasbord of visual delights, or at least as far as my penis is concerned.

“Oh,” I said, “We’ll see about that.”

Despite Applebloom’s insistence that “We’re not even wearin’ anythin’!”, Bab’s had insisted both girls go upstairs to change into something for the game. The weirdness of a normally naked horse covering itself almost made the whole thing more erotic. Or I had a serious perversion of some kind. Either or.

I waited on the court outside the Apple Family House for eighteen minutes before I was ready to go back inside and yell up the stairs, but just as I was about to step off the asphalt, the two fillies came bounding out the front door, Applebloom shouting “We’re ready!”

Oh, good lord were they ready.

Applebloom did not, by herself, look sexy specifically. It was more so that she was wearing the perfectly tomboyish sports outfit—a white top with green highlights on the short sleeves, and a pair of slightly too-big sweatpants that looked like they may have been a hand-me-down from one of her cousins. Sweatpants aren’t necessarily sexy, but they can be, depending on who’s wearing them.

Babs, on the other hand, was on the verge of becoming full-fledged jailbait: a small, punky denim jacket matched her faux-hawk, and the jean-shorts that hugged her backside were so tight I could make out the full form of her butt, every illegally delicious curve that I should not, by any means, be staring at while half-hard in my jeans.

“Uh,” I said. “Are you… are you girls, uh, ready, then?”

“We’re ready!” Babs said with a smirk, and what seemed like almost too much growl—a growl that made half-hard into a full on erection. Was any of that sex appeal actually there, or was I just delusional after months of absolutely no human contact besides my right hand?

Hoofball is, for those interested, basically basketball, but with hooves. God, shoot me for writing that. What that difference means in practice, however, is that the ball is much easier to bounce when you have a solid hoof to pound it into the ground with, and also that the action of the actual bouncing occurs much lower to the ground that humans are used to. Specifically, ducking down to two feet in height to intercept a pass or dribble is difficult, and dangerous to your spinal health. But what could I say if I didn’t try? So the game started, already in my mind vastly in the girls’ favour, and all the while me trying not to get caught staring at Babs’s ass for any length of time.

However, what neither I nor the girls seemed to be counting on was the fact that despite their every physiological advantage in a sport designed specifically for ponies, they still couldn’t account for raw human reach, flexibility, and my two years playing on my college basketball team.

Deciding on a first to ten, on the basis that I consider myself out-of-shape despite my various handyman tasks, and that the girls were likely to get bored or frustrated with anything much longer, the game proceeded with an almost dangerous lead on my part. A 2-0 became a 6-0 in minutes, and the look in the girls’ eyes almost made me want to play worse on purpose. But, on the other hand, if I focused on playing, it meant I was less distracted by the filly-bait bouncing around on court beside me.

But almost as tho she could sense my gameplan, Babs changed her behavior on the court immediately. Where both she and Applebloom had kept distance and let me take the ball from them while barely trying, Babs did a full 180() into non-stop aggression, checking me from every side, giving me no breathing room—and, on top of that, mashing the squishy curvature of her plot into me every chance she got. There’s no way, I thought to myself, that this isn’t on purpose. But Babs is just a filly… do fillies even know about intercourse at this age in Equestria? Am I just a legit pony pedophile?

Whatever the answer to that question, the game tied up 6-6 at an equally alarming rate, and before either team could get their bearings properly it was tied up at 9-9, game point. The single free throw between me and escape from the immediacy of my lustful, pony-butt urges. I could do this.

The break began almost in slow motion—Applebloom covered to my left, closer than she ever had been, tho luckily not close enough to incite the same stirrings Babs was. As was the new usual, Babs charged me full on, aiming to get as close to me as she could without actually touching me—and then, sometimes, accidentally(?) touching me, shorts to leg, shorts to hip, shorts to the luckily concealed bulge under my jeans. This time, I was determined not to play her game—it was a hard circle around that she couldn’t catch, and then the winning point.

The run started well, at first—I faked left, got Babs to flinch, and then bolted around. Dribbling didn’t feel hard, even with the extra-inflated ball (hoof thing). I could do this. Victory was in sight.

Babs, however, was in sight too, faster than I knew she could move, in front of me with the block. I was going too fast to stop, and with no way to stall my momentum or do anything with the ball, I did the only thing I could and slammed my feet to a lurch, praying I wouldn’t collide with this poor little pony and give her her first concussion.

The tumble wasn’t hard—Babs saw it coming, eyes wide, and braced herself, and the two of us flew forward and upside down into a bundle of limbs, pony-fuzz, and short-shorts. As entropy would have it, the landing position happened to be the den of Satan himself—Babs on her stomach, in front of me, and me fallen on top of her, my crotch pointed somewhere very particular that it should absolutely not be pointed.

“Oh,” I said. “Ohmygosh. Are you okay?” For some reason, I couldn’t move, paralyzed with some combination of shock and fear that Babs would feel my erection and call me out that second for being a filly-fiddler. Oh gosh. Please don’t let them send me to the special dungeon…

“I’m… uh… yeah. I’m… fine.” Babs’s voice sounded a tad laboured, but that’s natural if she was winded. What was odder was that she was moving, but not in any effort to get up. Her legs were tensing, lifting her hips up and down, pressing her onto my…

I couldn’t help but look down. And see the hoof-sized wet-spot on the back of Babs’s shorts. The wet-spot that had a very familiar feeling being ground back onto my cock, even thru the thick layer of denim that was there.

“Babs… are you…”

Babs turned her head, eyes wide, mouth open in a silent ‘no’.

“Uh… I mean, we should get you up and make sure you’re not too hurt. Lemme help you…” With my right hand, I reached down and picked Babs up like she was a little kid, holding her close to my stomach to conceal the transparency at the back of her basketball attire.

“I think I’m okay,” Babs said quietly. She leaned forward and let her head rest on my shoulder.

Nevertheless, going over her legs for scrapes and bruises was a good chance to get my mind off what had just happened, and Babs ran upstairs to change as soon as I was done, Applebloom all the while puttering around, quietly admiring her cousin’s silent endurance of a theoretical pain.

“All right, it seems like you’re all patched up. Just a few scrapes, shouldn’t be anything to worry about. Do you two wanna go upstairs and change again, then come downstairs and have some hot-chocolate before bed?” Damn. How could I be a pervert and such a good babysitter at the same time? Loving kids and loving kids are two very different ideas, in my mind. Or were, until very recently…

“Sure!” Babs and Applebloom shouted in unison, and, with as much coordination, turned and trotted up the stairs to Applebloom’s room.

Now, finally, I could deal with the pain of a boner contained for almost a half hour. Just a touch made me feel like I was about to burst—so I unzipped and let myself just hang, air out, until my erection began to subside, and I could zip myself up again. Luckily, the girls didn’t come downstairs until after I was done.

After an incident free hot-chocolate session (not counting argument over whose cup had more marshmallows, which was easily resolved by adding more marshmallows to both cups, and throwing a few at their owners for good measure), the girls, tho reluctant, made their way up to bed. Normally that means I’d take a little bit of time to relax in the house proper myself—nothing like a fire in the Apple Family Fireplace—but taking care of two fillies as high-spirited as Babs and Applebloom had left me with just enough energy to crawl up to the guest bed and pass out. I’m not sure how long I’d been sleeping for when I heard the door creek open, loud enough to wake me from my fuzzy sleep.

My eyes were barely open when Babs’s voice came to me from the doorway: “Applebloom’s snoring is way too loud to sleep. Can I stay in here with you?”

This is how it starts, I told myself. This is how you end up in pony prison. You let a little filly with a ten-star ass jump into your bed and grind against you, and your hands are on her and before you know it you’re balls deep in the hottest butt you’ve ever seen before the pony police show up and drag you into the eternal dungeon where pink monkies like you are stretched out elaborate torture racks and made to watch Pinkie Pie’s Puppet Parties on repeat for the rest of their lives—

Babs hadn’t waited for me to answer; while I was deep in the metaphysical ramifications of letting a (potentially) innocent girl sleep in my bed, Babs had made the decision for me, and was currently snuggling up under the covers in front of me, her head turned to face the wall. Little spoon.

“Is this okay? I don’t have too much blankets, do I?”

“Uh… no, you don’t, but, Babs—“

“What? Do you not want me here? It’s not my fault Applebloom sounds like a chainsaw with a sinus infection.”

Don’t laugh. Don’t laugh. Get her out of your bed and don’t laugh and absolutely don’t laugh and then lean in and kiss her neck and cheeks and stomach and get your head between her oh god stop stop stop stop STOP.

“Listen, Babs… as much as I’d like to let you stay here, it really isn’t appropriate for us to be sharing a bed. It’s not the done thing, really, at least where I’m from—“

The full stop left my sentence as I felt the pressure of the softest butt I have ever felt in my life squish itself back against my boxers. My dick was already hard, and a little bit of pre soaked thru rubbed against the crack of Babs’s ass.

“It seems like you want to let me stay,” she said, half-facing me with a smirk. Oh god. She knows. She’s a goddamn pony Lolita.

“Babs, please, listen, I could get in a lot of trouble if you stay here, I need you to—“

No. Again, Babs had stolen the end of my sentence, this time with an extra hard grind and wiggle of her hips with my cock lodged between her butt cheeks, one thrust away from a proper hotdogging. And then the move.

“No,” I said. “No no no no no, no no no…”

“No what?” Babs asked, still moving her hips back and forth, lying in front of me. “You don’t want me to make you feel good?”

How. How did she know, what was she doing, how could any of this be happening?

“You’ve got a really nice cock,” she said, smirking even harder. “I bet it’d feel great inside me.”

Fuck!

Every atom of sexual instinct in me screamed as I yanked off the covers and jumped up to the other side of the bed, pulling myself away from the heavenly bliss of underage ponybutt. “Babs! We can’t do this! I don’t know where on earth you learned on this but where I come from, adults and kids do not do stuff like this.”

“I ain’t a kid,” Babs said, sticking her lip out ever so slightly. “Besides, it’s not a problem if I don’t tell anyone, is it.”

Oh God. Don’t do it. Don’t let her convince you. Don’t let her convince you to fuck her until she’s squealing all over your dick...

“You can’t… that’s not…”

“Come on. I saw the way you were lookin’ at my butt. I know I’ve got a good butt—it runs in the family. All the guys at my school like it too, but they’re losers, so they don’t get any. One or two maybe if they’re nice to me.”

Holy shit. Do ponies have entirely different standards than humans? Is Babs an underage sexpot or a normal filly who’s just coming on to me the way she’d come onto anyone? If it’s the latter—

Babs had again sprung before I could notice or even react. With a small leap, her forehooves had me pinned to the bed, and she swung her torso so that she was sitting right on my chest, just above the tent in my boxers, now pressed again against her filly curves.

“Do you wanna fuck me?” she asked, grinding her hips the same way she’d done so lying next to me, only now with the advantage of full control of movement, and an excellent angle to wedge my cock between her cheeks.

“Oh, gosh, Babs, I, I, we really shouldn’t…”

“That didn’t sound like a no to me,” she said. The smirk remained.

Listen, a voice in my head said, that may have been god, or just me justifying my penis in a slightly louder and boomier internal narrative than normal. You have two choices here: either A, agree to sex with an underage pony that seems to have every intent to both fuck your brains out, and not to tell anyone about it, or B, awkwardly send this dick-thirsty young filly back out into the cold, and risk having her spin the whole thing into a story about how you almost raped her.

Girls don’t do that, I replied. In fact, there’s no way to properly understand false rape statistics because they assume that all rapes are reported, which isn’t even remotely true.

Do you want to fuck the hot pony jailbait or not?

Fair point.

But if we were fucking, it was going to be on my terms.

“Hey, whoah, what are you—“ Babs blurted out as I grabbed her by the shoulders and yanked her off my stomach. Before she could react, our positions had mostly traded, with her lying face down on the bed, ass propped up in the air, with me behind her, a full view of everything I wanted to see.

“So you want me to fuck you?” I asked, running a hand along her back, touching her spine lightly and feeling the shivers run along her skin.

“Yes!” she practically shouted, which made me worry about whether or not Applebloom could hear us. Then again, if I was worrying about anything at this point, there wasn’t much point in doing it.

“You know, you have the nicest ass I’ve ever seen on a pony… on anyone, as a matter of fact.” To demonstrate my point, I wrapped my hands around Babs’s cheeks and squeezed, kneading her soft skin in my palms, crossed between a massage and a dancing of my fingers closer to between her legs, the spot I knew that was already dripping in anticipation of my cock.

“Ohhhh… ohhh, gosh, that feels so good… Is that what hands feel like?”

“It is, as a matter of fact. Hands are pretty… (handy? oh god…) useful, when it comes to sex. In a lot of ways.”

“Like what?” Babs asked with her head turned, a bead of sweat rolling down her forehead. She looked like pure sex.

Like this, I thought, tracing a finger down between her legs and along the length of her underage slit.

“OH! Ohmygosh! What are you… what is…”

My fingers were tracing movements up and down Babs pussy, in light circles around her lips and clit, never touching anything directly, driving her so mad her hips began to arch off the bed.

“Unh! Unh! Please, please! Please touch me more!”

Fillies from Manehattan know what they want, apparently. But there’s also what I want, and it starts somewhere between Babs’s legs…

The wetness from Babs’s pussy was like nothing I’d ever tasted—not some silly nectar, or fake sweetness, but at least a soft, inviting tang that made me want to eat her out then and there. But with more pressing matters to attend to, I moved further down, tracing my tongue over her slit and down to the smaller hole below, the treasure in the center of her most pronounced assets.

She almost jumped when my tongue touched the rim of her asshole at first, but as soon as the feeling of panic seemed to hit, it disappeared under a flood of something stronger. Babs moaned unintelligibly and slammed her forehooves against the bed as I licked her ass, occasionally darting my tongue up to taste the new wetness Babs’s pussy was dripping. Still ever so faintly sweet, and great lube for my attentions to her butt.

“Oh, oh gosh, s-, s-stop, you gotta stop before I, I…”

When a girl’s afraid to come, it’s because she doesn’t want to lose control. Letting go is scary. Sometimes, you just have to give them a little push.

Moving my tongue up Babs’s wet pussy again, I found her clit, and began to lap in circles, while my index finger traced around the rim of her butthole again before plunging in, feeling the tightness of her ass clench around this new presence.

“Holy fuck! Holy shit! Oh my gosh, oh my gosh, what are you, why, oh my g-gosh, I’m gonna…”

Babs reminded me of my last girlfriend—so loud a ball-gag became a practical accessory instead of a fun gratification. All I could do now was pray Applebloom’s snoring meant she was a heavy sleeper, as Babs locked her hind legs around my head and rode out her orgasm. She thrashed on the bed for fifteen seconds, wild slams and arches of her back like her orgasm had shaken her so hard, her limbs caught the aftershocks. Eventually, her legs relaxed, and I pulled my head out from between her legs.

“Was that good?” I asked. My turn to smile.

“Holy shit!” Babs half-sat up, balancing on her forehooves behind her back. “That was fucking amazing. I never knew I liked stuff in my butt.”

“It’s a good thing you do, because your butt is dangerously attractive already. If you like anal too… gosh. I might be in love.”

Oh fuck, oh fuck, don’t say that, she won’t know it was a joke—

Nor did she care, apparently. Babs sprung onto me with the same fervour that I’d sprung onto her, pinning me to the bed on my back, the same position she’d been in before—except now my boxers were askew, and my dick was poking out in plain sight, glistening with precum under the moonlight. Babs’ hips rocked even harder now, and I could feel her pussy juices on my stomach.

“So are you gonna fuck me now?” she asked, grinding still. Grinding, her ass pressing into my cock, wet and soft. But fucking her…

I didn’t know if I could do it. It’s one thing, in my mind, to fool around with a girl (filly, sorry) who’s underage—it’s another entirely to fuck her underage pussy—mostly because there’s a chance I’ll go to jail after all’s said and done anyway. But did that mean we couldn’t fuck? Well…

“Listen, Babs,” I said, putting a hand on her shoulder as I spoke and rubbing her neck. She closed her eyes and sighed softly as I did, but didn’t stop grinding, shaking her hips back and forth in circles against my rock hard dick. “I don’t think I can fuck you. I already feel wrong about all this, as much as I like you, and as much fun as it’s been… but I just don’t think I can do that.”

Babs’s eyes almost broke my heart. God, how did I get into this mess, reducing a young pony to tears over the absence of my cock.

“But… but I’ve done it before! With plenty of guys! And I like you way more than them!”

“Babs,” I said, putting another hand on her other shoulder to steady her. Her eyes locked with mine, and when she saw me smile, she smiled just a bit too. “I’m not going to… well, I don’t feel like I can fuck you the normal way. But what about… well… how would you feel about…”

“My butt?” Babs asked, giving it a push back for extra emphasis.

“No! Well… maybe.”

“No way! I’m not just gonna let some guy do me up the butt just ‘cause he wants to. It’s my pussy or nothing, mister.”

How could a kid be so good at haggling? Another trait that must run in the family, given the prices at Applebloom’s lemonade stand…

“How about this; you try it for one minute. If you don’t like it, we stop, and I’ll go down on you again. But if you do like it…”

“Hmph. I won’t.”

“Weren’t you just saying how good it felt when I was fingering your ass?”

“That’s different!” Babs turned her face with a hot flush of red on her cheeks. Ever the tsun-tsun, never the dere.

“It really isn’t, Babs. I love your butt, and I wanna do more with you, but you’ve gotta respect my standards too. Especially considering… well… you know.”

“Yeah yeah, I know. You do believe I ain’t gonna tell on you, right? I’d get in trouble too.”

Would she? Maybe the law in Equestria respects the sexual consent of minors… “Right. No, I trust you. I just… just work with me on this, okay?”

“Okay. But I get to be on top.”

“That’s actually probably better, so you can control the speed. Here, just lemme take my boxers—“

“I’ve got ‘em.” Babs grabbed the waistband with her teeth and yanked them down over my feet, throwing them somewhere into the dark floor of the bedroom.

Oh gosh. What did I get myself into.

Babs resumed her previous position naturally, but this time with her hips raised slightly, poised to look for the stiff thing ready to fill her up. She looked nervous, almost, and I reached out a hand to steady her. I caught a glare for it, but the glare turned to a smile after only a second.

“Do you want me to guide you down?”

“Naw, I can do it. I have lots of practice bein’ on top.”

Oh gosh, young, horny, and a complete slut. There’s no escape from hell after this one…

I gasped when I felt Babs sliding her pussy along my cock, her lips rubbing over my hardness, lubing my dick with her wetness. Rubbing so close the tip was almost in.

“Babs—“

“Shush, I’m just getting you wet. I don’t want it to hurt too much.”

Right. Right. This is okay. It’s somehow okay that you’re fucking an underage pony in the ass, but not her pussy. Oh fuck me and any system of morals, maybe Nietszche was right…

Babs lowered her hips without a word, and I felt the tip of my cock enveloped in warmth and wetness. I gasped, and lifted my head to look down to see Babs smirking up at me, the first two inches of my cock inside her ass.

“You know,” she said, “this actually feels pretty fucking good.”

The rest of my cock vanished as she plunged down—from zero to sixty, empty to full, from poised to fuck into absolutely being balls deep in the hottest filly ass that might exist in Equestria.

“Oh. Oh shit.” Babs’s words came strained, as tho she was fighting off a feeling inside her eager to rob her off words. “Ohhh, shit, I can’t believe it, I think I’m gonna…

Her ass clenched around my dick as she began to cum. Her pussy leaked. My cock twitched and throbbed as she bucked her hips again, never letting my hardness leave the inside of her ass, cheeks slamming against my legs as she bounced up and down like she was overtaken by a spirit, only to return fifteen seconds later, panting and wide-eyed, like she’d been hit by a personal-sized tornado.

“Holy fuck. That was the best thing I’ve ever felt.”

“I told you that you might like it.”

“Shut up. Just sit there and lemme fuck you.”

“No way.” If I was going to pave the way to hell by becoming a full-fledged filly-fucker, I was going to do it on my terms.

“Hey, what are you—“ Babs’s voice caught as I picked her up off my stomach (easily, considering her miniscule weight) and flipped our positions yet again—this time, her on the bed, face down, and me behind her.

“What the heck are you doin’?! Cut it out!”

“Shush, you. Where I come from, little girls don’t get to call the shots during sex.” Oh god. This is so weird. This is so weird. This is so fucking hot.

“I ain’t a little girl!” Babs struggled against me as I held her to the bed, thrashing her cute little butt up against my boxers and making me want to abandon the pretence of teaching her and let my dick do the rest of the thinking.

“Well, you sure look like one to me. And, as a matter of fact, right now you’re not behaving very well either.” I ran a hand along Babs’s ass as I spoke, squeezing her right butt-cheek and getting a shiver for my troubles.

“Shut up! Are you gonna fuck me or ain’t ya?”

“Yes… eventually.” My hand squeezed hard on Babs’s ass, getting another shiver, this time coupled with a hard arch of her back. Her pussy was dripping. If wanting to fuck a pony this sexy was wrong, there’s no world where I wanted to be right. “First… we have to deal with your punishment.”

“Punishment? For what—Ow!”

The ‘ow’ came coupled with the ring of a soft slap, my hand against Babs’s right cheek that I was so fond off. I barely hit her, but got a faint white marking of my hand regardless, and an arch of her back so hard it looked like her pussy was begging for my dick then and there. Winking, I think ponies call it? I wish human girls could do that.

“What was that for?” Babs’s voice had gone from slightly indignant to full-fledged rebellious, which was, more or less, exactly what I wanted. This wasn’t my first rodeo with a rambunctious girl—just one that happened to be a pony with ‘jailbait’ written on every inch of her curvy little ass. An ass bigger than it had any right to be considering Babs’s overall size and tiny waist. An ass that would get her in a lot of trouble in the future—and, as a matter of fact, was getting her into trouble right now.

“For thinking you’d get to be in charge of things. This is your first time, so I’m going to be the one doing the work. And right now, I’m punishing you for being such a little brat.”

“Ponyfeathers! Let me go right now or I’m not gonna let you—Ow!”

Another slap, a step up from the first, the mark on Babs’s left cheek slightly brighter red than her right.

“The more you complain, the longer the punishment continues.” Smack.

“Ow! Fucker!”

Huh. I didn’t know ponies knew swear-words like that. Smack.

“Ow!”

Babs had stopped complaining now—what’s more, her ‘ow’s were getting quieter, and starting to sound a lot like the moans she’d made when I was eating her out earlier. Her back was moving like a snake, thrashing and twitching in serpentine, every arch smooshing her booty up against my cock, which had by now surrendered completely to a hardness beyond rock. The spanks went up to fifteen, and Babs didn’t seem like she could take any more—her pussy was leaking down the insides of her legs, all over the bed, and her ‘ow’s had become muffled nonsense-noises into the pillow, sounding like she might be ready to cum from just a small breath onto her sex.

“Do you feel like you learned your lesson?” I asked, removing both my hands from Babs’ underage body and giving her a second to collect herself. A second became thirty before she pulled her face from the pillow, dripping with sweat, her pink-highlight faux-hawk drenched and hanging over her face.

“Yes,” she said, almost moaned, a quiet breath between her teeth.

“Do you want me to fuck you now?”

“Yessssss…” She hissed the end of the word, swiveling her hips backwards, searching for the hardness of my dick, which I pulled away.

“Can you say please?”

“Please,” she said, every trace of her rebelliousness drowned in lust, the heat of her body and the ache for something inside her.

“Please what?” My cock was free from my boxers now, poking against her slit, but not giving her enough to grind herself on. Reminding myself of the one line I mustn’t cross, for some arbitrary reason in my head. For the same reason I was about to fuck the hottest ass I’d ever seen in my life.

“Please fuck me,” Babs moaned, arching her back and grinding her hips backwards as far as she could. Still not enough—still not quite.

“Fuck you where?”

“Please fuck my ass!” Babs practically shouted it, and it became apparent that any more teasing would be sure to confirm my fears of Applebloom overhearing us, no matter how heavy a sleeper she was. It was time to fuck Babs’s ass. My cock was wet enough from dragging it along her slit, and she was so horny and eager that the moment I put the tip against her entrance, it slid in with almost no resistance, the first half-an-inch into this little filly’s underage butt.

“Oh,” I said, unable to catch myself. “Gosh, that’s… you’re really tight.”

Babs moaned something completely unintelligible. I’d like to translate any portion of it so I could share the sense of complete, absolute lust I felt at that moment for the tiny pony babbling as I filled her with my cock, but the sound remains in a trace of my memory, the magical noise of a filly getting her first ass-fucking.

“Are you okay?” I had enough sense still to remember that no matter how horny Babs was, anal could go wrong if either party made mistakes.

“Yuh… yuh-huh… I’m… I’m really… good…” Babs’s words came between gasped breaths, each one accompanied by a thrust backwards of her hips. I was controlling the depth very carefully, aware that no matter how much Babs might want the entirety of my dick inside her, she was so little that going that fast might lead to serious unpleasantness in the middle of what was quickly shaping up to be the best sex of both our lives.

“You mean you like having my cock in your ass?” I pushed forward a little with each word to about half-way, letting Babs get accustomed to every length before I pushed in further. To be honest, the concern seemed completely unnecessary—Babs was in what looked to be full heat, or a non-seasonal equivalent, thrashing and arching her back again and again, desperate for the full length of my hardness to be buried inside her. God, was this filly cock-hungry.

“Yuh… y-yes… oh, Celestia, fuck, I’m gonna…”

That was as good an invitation as any to bury myself in Babs’s ass. And she came as soon as I did so, clenching around me, squeezing my cock in an unintentionally fervent effort to get me to cum inside her tight little butt. But I resisted, as difficult as it was, letting her bounce on me in half-inch bursts, squealing into the pillow (thank goodness for Applebloom), her pussy winking at me for every second she continued to thrash on my cock. When Babs came, she came hard—and when her orgasm subsided, it took her half a minute to raise her face from the pillow and look back at me with eyes as wide as tea-saucers.

“Wow,” she said, the least sarcasm in her voice I’d ever heard. “That was… wow.”

“We’re not done yet.”

“Ohmygosh, what’re you—“

Babs was light enough to pick up with one arm, but I used both to support her as I stood up from the bed and held her against my chest. I’d always wanted to do this with a girl, but a tiny pony was, in almost every way, much better. She was so small that the wrongness of the whole act was even more palpable, knowing I was clutching a cute little filly in my arms while I bounced her ass up and down on my dick.

“Unh! Oh… unh! Fuck! That’s… so… good!”

Babs was letting out gruff little moans when I slammed her down now, which made me slam her down faster and harder, being rewarded with even more of the sound that was keeping my cock harder than diamond. It was a lot harder not to cum than I thought it would be—the full eroticism of fucking Babs’s butt while her pussy dripped down the front of her legs and onto my cock… there was a good chance I wasn’t going to last much longer.

“Fuck, fuck, unh, I’m cumming, a-again, oh, fuck…”

I reached a hand down to Babs’s clit and rubbed at a soft and steady pace. She seized up instantly, ass tight around my cock like it was determined to make me cum then and there. I let out an involuntary gasp, but managed to both hold my load, and keep my hand working. Babs clit was soaked with her pussy juice, and I could feel her winking again as she kept cumming, another torrential orgasm before I pulled her up off my cock and lowered her onto the bed. No wet spot, luckily, as I lay down beside her.

It felt appropriate to say something—but, as I turned my head, and caught a glimpse of Babs, staring into the ceiling like she’d seen a new heaven, the words caught in my mouth. It was easier just to watch her, seeing her chest rise and fall, almost in time with my own heartbeat I could feel still twitching in my erect cock.

“Are you up for one more round?” I asked. It’s no secret that anal can be a tricky practice, and especially for a little filly’s first time—

“Absofuckinglutely. Are you stupid or somethin’?”

How Babs could be both charmingly adorable and a surly ball of sarcastic aggression at the same time was a mystery to me, but probably part of what had gotten me into bed with her like this in the first place. I was just raising myself up off the bed with my arms behind my back when Babs crawled on top of me, resuming the position she’d taken before my cock had first entered her ass.

“Uh-unh,” she said, shaking her head. “I get to be on top this time.”

When a girl knows what she wants, I am not one to complain.

Watching Babs steady herself above my cock was almost as erotic as fucking her—she had to check a few times to make sure she was properly lined up, resulting in a few slips and misses which slid my cock thru her lubed up buttcheeks, earning clenched teeth and the hope that I wouldn’t blow my load before getting to be in her butt one more time. Eventually, she found her bearing, and the feeling of velvet-warm vice that I’d grown to know over the last half hour returned, Babs’s ass clenching the head of my cock, then sliding all the way down the shaft until the entirety was buried inside her, far more than a filly should be able to take, but there nonetheless, filling her up so well her pussy winked once to show its approval.

“Can you move?” I asked, raising my hands to her side to lift her. But her hooves stopped me.

“Yeah,” she said. “I can do it.”

For the same reason that food someone else has cooked always tastes better, watching Babs raise and lower herself on my cock almost instantly brought me to orgasm—where all my focus before had been on her, making certain the highly illegal and questionably immoral act I was committing wasn’t hurting her in any way, and then that she was enjoying herself enough to want to keep going. Now, all my attention was still on Babs, but on what she was doing to me—grunting as she lowered her ass onto my cock, taking a deep, low breath as she became accustomed to the length and feeling of fullness, then a long breath in, light, desperate, as she raised herself, slow, feeling every inch slide out of her butt before she steadied herself for the next drop. There was, in other words, no way for me to last for more than a few minutes.

“Babs,” I said, the same haste in my voice that had carried her last few orgasms. “I’m really close. I think I’m gonna cum…”

That was enough warning, but Babs didn’t seem to notice or care, still bouncing herself up and down, moan after groan, eyes closed, lost in a completely different world. There was no turning back now. I could feel my balls clenched as she slammed down over and over, the slapping of her ass creating a rhythmic pulse that urged me to let go of my load. I was about to cum when—

Babs got up, completely. Her ass hovered above my cock, and when I raised my eyes to meet hers, the devilish smirk I’d seen when I first met her answered me.

“Are you sure you don’t wanna cum in my pussy instead?”

Before I could answer, Babs had lowered herself again—this time with my cock aimed at a decidedly wetter and more inviting hole. The one I wasn’t supposed to be in. The one I was about to cum in.

“Holy shit, Babs—“ There was no time to move her, to stop myself. My balls clenched as the first shot of cum worked its way up my shaft, into Babs’s underage pussy, into her fertile, illegal, prison-sentence dripping fuckable pussy—“

Babs moved quick enough. The first shot of my cum fired onto her stomach, the head of my cock springing free from her underage sex only an instant before I came. Jet after jet of cum splashed onto her, her stomach, her face, her chest, all over her mane and cheeks and nose and everywhere that wasn’t inside her, thank god thank god thank god. And she smirked the whole time, almost giggling, knowing she had tricked me, and gotten a full load of my cum all over her as well.

“Holy. Fuck.” I fell backwards onto the bed as the last dribble of cum leaked down the side of my shaft, still semi-hard. Babs climbed off my stomach and did the same, lying down next to me as the tiny spoon again, just the right size for me to wrap my whole arm around her and tuck her close to my chest.

“Do you want me to go get you a towel?” I asked, running my free hand through her mane, the part that wasn’t sticky with my load.

“Nah, I’m good. I kinda like the feeling.” Babs nuzzled up against me, pressing her butt into my cock again, the feeling I’d now grown familiar to, turning half-hard into hard by light-speed.

“Babs,” I said, “you are one amazing filly.”

Babs giggled. “Don’t flatter me or nothin’.” She wiggled again, butt to crotch, the perfect fit between us.

“You… know that what we just did is technically wrong, right?”

“Which one, wrong or right?”

Argh. “Fuck. I mean… I mean it was probably illegal, right? A filly having sex with a guy—with anyone my age?”

“I dunno.” Babs shrugged and yawned, grabbing a bunch of blankets and pulling them closer around her body. “I don’t really care, to be honest. That’s the best sex I’ve ever had.”

“Have you had a lot of sex?”

“Some. But nothing like that.”

“And you’re not going to tell anyone?”

“Nah, I said I wouldn’t. ‘sides, then you wouldn’t fuck me anymore, would ya?”

With a sigh, I nuzzled my nose into Babs’s mane, smelling the implacable sweet aroma of her shampoo and young filly’s scent. The night was at its peak now, with the moon sending a sheer beam of silver light thru the window and onto the ground, casting a reverse shadow at the foot of the bed where I’d done something that I’d never thought I’d do, and felt no worse for it.

“Babs,” I said, hugging her from behind, “you are something else.”

“I know,” she said, smirking.