The Megalomaniacal Mare

by Some Leech

Rating: mature
Tags: Anon, My Little Pony: Friendship is Magic, Porn, Fetish, Comedy, Cozy Glow, Profanity, Slice of Life, Sex, Human
Length: 5785

After a string of unfortunate events, Anon finds himself in Tartarus. Fortunately, he has someone to keep him company...

Past mistakes have finally caught up with Anonymous. Time after time, he had one lewd encounter after another, all with students at the School of Friendship. Well, after his most recent fling, with one very sexually aggressive yak, he's paying the price. After being caught by Twilight Sparkle, Anon finds himself whisked away to Pony Hell Tartarus. Mercifully, he's not alone in his imprisonment; but he has to ask himself, why would anyone jail such a small, innocent mare?!?

Kinks Include: Foalcon (🤔), Interspecies, Female on Male, Male on Female, Oral, Vaginal, Rough Sex, Size Difference, Stomach and/or Throat Bulging, Creampies, Squirting, and Copious Amounts of Man Jam

EXTRA LEWD KINKS INCLUDE: Prurient Punishments...

This was a collab with my buddy Aer0 Zer0 (Find him on Twitter). He provided the art, I produced the story.
Hope y'all enjoy it!

Published 2019-05-18 18:30:01 UTC
Last updated 2019-05-18 18:30:01 UTC

And the Confused Convict

Walking across the cold and dreary confines of his cell, Anon knelt to greet his unexpected roommate. “Hi, I’m Anon,” he announced, wearily extending his hand to the diminutive, shadowed figure. Slowly, a pinkish grey hoof reached in his direction; but before he could shake it, it retracted. “Hey, I’m not gonna hurt you,” he sighed, squatting to his haunches in an attempt to reduce his imposing height. After all, he was a fair bit taller than a great many of Equestria’s denizens.

“I...I’m Cozy...Cozy Glow,” the tiny mare fretfully muttered, stepping forward and into the light.

In all of Anon’s time in the land of magical pastel ponies, he’d never seen a pegasus mare so small. Cozy was positively runtish, only coming up to his knees. Curly greyish blue locks sat atop her head, with her tail styled in much the same fashion. Her coat, a dull peach color, contrasted her hair. Heck, she even had a few snow white freckles on her cheeks just below her saucer-like scarlet eyes. All told, she could pass for the horse version of little orphan Annie.

Taking her hoof in his hand, he gingerly gave it a shake. “Nice to meet you Cozy,” he softly said, giving her a warm smile.

“N...nice to meet you too,” Cozy whimpered, sheepishly looking up at the man. “I think Twilight told me about you, aren’t you a janitor at the School of Friendship? Oh no! Don’t tell me those mean old ponies threw you in here by mistake too?” she continued, her timid demeanor turning all the more dour.

“Well…” Anon began, releasing her limb to rub the back of his neck, “it’s a long story…”

And what the long and sordid story it was. Basically, he’d had the perfect setup; a job as a custodian at the School of Friendship, a great relationship with the faculty and student body, and even a little apartment to call his own, but things had quickly taken an unexpected and scandalous turn. Somehow, for one reason or another, he’d managed to find himself in rather intimate relationships with several of the young creatures attending the academy. Chronologically, Anon had done the do with a changeling, a dragoness, a hippogriff, and even a yak. It wasn’t even like he’d gone out trying to get laid, everything sort of just happened.

The straw, or should he say yak, that broke the camel’s back had been Yona, the obstinate bovine. Apparently, she’d been privy to his salacious activities, and had developed a thirst for some human lovin’. Try as he might, he was only able to stave off her advances for so long. Eventually, frustrated beyond all reasoning, she’d bludgeoned her way into his room and rutted herself on him. Now, as one may expect, this didn’t go over all that well with the Academy’s staff, not to mention the disgraceful sight it had created.

Having been caught balls deep in a yak, by principle Twilight Sparkle, Anon didn’t have a leg to stand on. Not only had he been discovered plowing a student, but the event had sparked a heated argument regarding whom had won his affection. Under the baleful gaze of the alicorn Princess, Anon had been banished to the prison he now occupied, for committing the heresy of creating a friendship problem. In short, he’d fucked up on multiple levels.

“Mister…” Cozy whispered, blushing and averting her gaze, “I can see your wiener…”

The tiny mare’s humble words dragged Anon from his despondent state. Sadly, Twilight had teleported him to his current location buck naked, leaving the filly an unabashed view of his dangly bits. Darting for the mattress, he tore off its cover, and swiftly crafted a makeshift toga from the linen. It wasn’t much, but it gave him some semblance of humility.

“A...anyways,” Anon stammered, turning his attention back to his cellmate, “I wouldn’t say the ponies are mean, I just made a few mistakes and got thrown in here. I’m sure it’ll all get sorted out.”

“Well, I think they’re a bunch of grumps. They put me in here because I wanted to make friends!” Cozy attested, solemnly kicking at the hard stone floor.

“What? You’re kidding, right?” Anon blurted, utterly confounded by the admission. All throughout his time in Equestria, he’d never seen or heard of anyone being anything but friendly. Before he could respond, a raspy voice crept from over his shoulder.

“She’s right, you know. Poor Cozy was locked up, simply because she wanted to be my friend,” something called, followed by the sound of hooves.

Wheeling around, Anon found himself facing a wizened, centaur-like creature. “Wait...I think I’ve heard of you,” he muttered, squinting at the odd beast.

“Tirek,” the creature answered, giving a slight bow, “it’s a pleasure.”

“Hold on, you’re the dude who blew up Twilight’s house! She told me about you!” Anon exclaimed, taking a step away from the bars. Fortunately, Tirek was in a different cell, but he was still reluctant to get close to the villian. Out of the blue, something bumped against his leg, causing him to look downward. There, with her forehooves draped around his calf, sat the filly with whom he was imprisoned.

“Principal Twilight wanted us to have friends, and poor old Tirek was trapped down here all by himself. I started to write him letters, because I just felt so bad for him, but then the Princess threw me down here…” Cozy sniffled, looking up at Anon with tears in her eyes.

Kneeling down, Anon picked up the filly and gave her a hug. For all he knew, Cozy may have been a victim of circumstance, just like himself. She was just a kid, for fuck’s sake! Holding the small pony to himself, she wrapped her forelegs around his neck and pressed her face to his collar.

“I like you already, Anon. You’re just super-duper strong, and handsome, and you even smell nice,” Cozy cooed.

“You seem pretty sweet yourself!” Anon chuckled. Clutching the girl, he took a moment to take stock of his surroundings.

The cell was small, and painfully spartan. In one corner sat a toilet, shower pan, and a sprinkler head, at roughly waist level. The only bedding was a single mattress, positioned in the opposite corner of the room, beside himself. Whoever had designed the jail, clearly hadn’t accounted for larger creatures, like him. The worst part that there’d be no privacy whatsoever. The walls were constructed of rigid metal bars; easily allowing Tirek, or anyone else, from looking within, and that wasn’t even taking into account his bunkmate.

“They seriously don’t even give us any clothes?” he asked, turning to face the centaur beast in the next enclosure.

“Why should they? We’re prisoners, so we’re afforded the bare minimum for survival,” Tirek replied, with a shrug. “Anyways, I’m going to get back to bed. I’m sure we can continue this conversation in the morning. That is, unless you find something more entertaining to preoccupy yourself with…” he snickered, slinking back off to his sleeping mat.

Considering Anon had appeared in the late hours of the night, he couldn’t blame him. Hell, he was actually pretty tired himself, given the maelstrom of bullshit he’d been through. Regardless of what he decided to do, he’d likely have to wait until morning, when he’d hopefully get the chance to ask a guard for something to wear. A muffled yawn drew his attention downward, towards the mare in his arms. With only a single mattress in the room, it looked like he and Cozy would be sharing the bed for the night.

“Come on,” he groaned, easing himself onto the bunk, “let’s get some rest.”

“Are you sure? You don’t mind sleeping with a filly?” Cozy murmured fretfully.

“Nah, you’re fine. I promise I won’t do anything weird, but I might snore a little,” Anon mumbled.

Carefully, he laid back, after setting the filly beside himself. Thankfully, there was still a blanket to share, so they wouldn’t get too cold. Curling up next to him, Cozy snuggled herself against his side. Even though she was small, she was surprisingly warm, and the added heat was a welcome sensation.

“G’night Cozy,” he whispered, running his fingers through her curly mane.

“Night night, Anon,” Cozy softy responded, as she closed her eyes and rested her head.

Having made himself as comfortable as possible, Anon cast his gaze to the ceiling. One way or another, he’d have to find a way out of here; or, at the very least, speak with Twilight. To an extent, he could see why he’d been locked up, but not a filly like Cozy. Steadily, his eyelids grew heavy, and he drifted off into a heavy slumber.

What must have been hours passed in what felt like mere moments, as Anon awoke in a rather compromising position. It wasn’t the fact that he’d tossed off the blanket, a common occurrence for him while sleeping; no, it was something altogether more disconcerting. Somewhere over the course of the night, his toga had slipped from his torso, leaving his bare chest exposed, yet this wasn’t the source of his discomfort.

Cozy, likely whilst snoozing, had positioned herself onto Anon’s groin. To make matters worse, her muzzle was firmly betwixt his dong and balls. Glancing over, he noted Tirek was still asleep, and breathed a sigh of relief. The last thing he wanted was for the quadrupedal villain to see him in such a state.

Reaching down, Anon tried to slip his fingers under the filly’s chin. His attempts to remove the young mare were stymied, as she felt his movement. Wrapping her legs around his thigh, she nuzzled his package and yawned sleepily, permitting one of his balls to flop into her maw. He froze, not knowing what to do.

“H...hey, Cozy,” he quietly said, brushing her ear, “you gotta get up.” There was no way of knowing if, or when, a guard would come strolling by, so he needed to act quickly. Sweet Celestia, he didn’t need some random pony finding him like this.

Dreamily, Cozy’s eyes fluttered open, allowing her to look up Anon’s frame, to his nervous face. Sensing something warm in her mouth, she peered to her muzzle, then to the man’s groin, before lazily tonguing the man’s nut out of her gob.

“Mornin, Anon. I hope you slept well,” she sighed, her snout still a scant few millimeters from his junk.

Anon opened his mouth, but was at a loss for words. Cozy had acted like it was any other morning, despite waking up with some guy’s teste in her maw. Languidly, the puny mare got to her hooves, stepped over his waist, and straddled herself on his lower abdomen, just above his groin. Now beaming at him, she wiggled her rump contentedly. He gulped, keenly feeling the warmth and subtle moisture of her loins against his flesh.

“I’m so glad to have someone to play with now,” she hummed, continuing to gyrate on the man. “It’s so cold and lonely down here, and washing my mane has been a real pain in the butt. Oh, I know!” she chirped, leaning forward and draping herself over his chest. “You could help me with my hair! It’s not easy, since I don’t have any magic or anything.”

“I...I don’t know, Cozy…” Anon grumbled, attempting not to look her in the eyes. Something about all this was just wrong. After having stumbled into multiple lascivious situations with students, he’d started getting somewhat paranoid about anything involving young mares, especially when they started asking for help with things.

“Pleeeeease,” Cozy pleaded, her lip quivering ever so slightly.

“Alright, I guess,” Anon relented. What’s the worst that could happen? Washing a filly’s hair was pretty tame, so he doubted anyone would give him flak about it.

Hefting Cozy, he set her beside himself on the bed. As soon as he released the runty mare, she hopped down and scampered over to the shower area. She quickly turned the tap, allowing the water to warm, prior to waving him over. With a sigh, and attempting to fix his shoddy toga, Anon plodded over. After all, it wasn’t like he had anything better to do.

Cozy’s gaze wandered over the man, while he walked over towards her, but only for a moment. Thrusting her hoof into the shower, she found the temperature adequate. Jumping into the basin, she let the water patter over her frame. In short order, her curly mane and tail dampened, unfurling to their full length, to drape over her face, neck, and rear.

“There should be some soap in a dish around here somewhere,” she pointed out, blindly waving a hoof to one side of the shower pan.

Spotting and retrieving the aforementioned brick of detergent, Anon squatted beside the basin. Reaching into the warm drizzle of water, he lathered his hands, before he ran the soap over the top of her head. While he gently washed Cozy’s scalp, she turned in place, making his job slightly easier. Her mane was actually pretty long, almost as long as Fluttershy’s, when it wasn’t all coiled up.

“So, what do you do all day, since you’re stuck down here?” Anon asked, attempting to strike up some idle conversation.

“Oh, you know, play chess, meditate, chat with Tirek, plan my rev…” Cozy paused, freezing in place, “eri, my reverie for when I eventually get out.”

“That doesn’t sound too bad, just kinda boring,” Anon commented, setting down the soap to rinse out her hair. He stopped, however, as her wing folded over his hand.

“Anon, you forgot my tail,” Cozy noted, peeking over at him. Spinning around, she presented her rear to the man.

Rolling his eyes, Anon went to finish his job. Working the soap in his hands, he gingerly brushed his fingers through her tail, taking care to avoid her dock. To his astonishment, he completed his task without incident. Handing Cozy the soap, she scoured her body with her surprisingly dexterous wings, before rinsing off. Looking around, he found a pair of pony sized towels, and readied one for his cellmate. As she stepped out, he handed it to her.

“Thanks, Anon. If you want to take your turn, I’ll be on the bed,” Cozy said, trotting off to the mattress.

“Alright,” Anon said, watching her dry herself and wrap the towel around her head.

He couldn’t say what he’d been expecting, but it hadn’t been something so mundane, not that he was complaining or anything. Honestly, he was thankful for the offer, since he was still sullied from his wholly unexpected romp with Yona. After making sure she wasn’t watching, he stripped himself from his toga. Stooping down, and damn near having to sit, Anon got in the shower. With the sprinkler just over his head, while in an awkward half-squatted position, he washed himself.

Closing his eyes, Anon played over the events since he’d arrived in the prison. Cozy seemed nice, almost too nice, and painfully innocent, which didn’t make any sense. Twilight would never incarcerate someone without reason, so he had to be missing something. The more he thought on it, the more frustrated he grew.

Rinsing off, he grabbed the other towel, and stood. Infuriatingly, the stupid thing was only the size of a human dishrag, but it was better than nothing. Drying himself, as best he could, he reached for his makeshift garment, but something was wrong. Glancing over, he discovered it was missing.

“Oh, I’m sorry, Anon! Were you looking for something?” Cozy inquired, causing the man to look over his shoulder.

Much to Anon’s horror, the small mare as lying on the bed, idly stroking her nethers with one forelimb, while her head rested on his discarded bedsheet-made-toga. Gone was the look of carefree innocence on Cozy’s face, replaced with the most sinister smirk he’d ever seen on a pony. As he went to cover himself, she shook her head and glowered.

“Anon, Anon, Anon, if I’d wanted you to cover yourself, do you think I’d have taken your little blanket? Now, come to me.” she tutted, shaking her head. Slowly, she extended a wing in his direction, and beckoned him over. When he didn’t comply, she scowled. “You know, it would be so much easier if you listened. After all,” she giggled, spreading her hind legs a hair and exposing her moistened loins, “it’s not like you won’t be getting something out of it…”

“I...why…” Anon sputtered, unable to form a reply. Up until a few minutes ago, she’d been as sweet as can be, but now she was acting like some two bit strumpet on prom night, and a petulant one at that!

“I’d do what she says,” Tirek grumbled, halfheartedly watching the scene unfold, from his bed.

When Anon looked back to Cozy, he found, much to his dismay, she’d shifted her position. Now, lying spread eagle and with her crotch facing in his direction, he was granted an unabashed look at her drooling marehood. Like a hungry dog smelling a meal, his loins stirred, despite his confusion.

“Why are you doing this? Are you in here because you’re some sort of nympho filly or something?!” he bleated.

“I’m doing this because I’m bored,” Cozy groaned, rolling her eyes.

Having quickly discovered she could slip out of her original cell, she’d scoured the depths of Tartarus for any sort of entertainment. Unfortunately, many of the monstrous captives weren’t capable of speech, and Tirek had no interest in her, since her failure, but she’d been undeterred. Upon hearing the rush of displaced air, and waking from her slumber, she’d darted into Anon’s cell. While he was too large to press between the bars, she was not; as such, as far as she was concerned, she had something new to play with.

“You’re wanting me to parade around naked because you’re bored? Are you kidding me?” Anon squaked, watching the filly roll to her stomach.

“No, silly! I want you to fuck my brains out with that meaty cock of yours!” Cozy responded, her voice losing any trace of menace, as it returned to its chaste, former state.

“You’re a kid! How do you even know about this stuff?!” Anon demanded, exceedingly disconcerted that a mare her age would make such a shameless request.

“Well, first of all, I’m older than I look; I just happen to be tiny, that’s all. Secondly, you act like I haven’t had my way with a stallion or two,” Cozy tittered, wiggling her tush at him. “And, before you ask, Tirek is a little too old for me. You, however, seem to be relatively young and healthy, and that hide of yours,” she purred, pausing to lick her lips, “is quite inviting…”

Anon held up a finger to protest, but fell short of saying anything. If he really was going to be trapped down here for a while, possibly forever, there wasn’t any sense in pissing off one of the two sapient inmates in the place.

“What about the guards?” he asked, noting the distinct lack of any staff in the prison.

“There are none. Tartarus is magically sealed, so there’s simply no need,” Tirek responded, absentmindedly picking at his fingernails.

Without any correctional personnel, any chances of Anon getting clothes were pretty darn slim. So he’d likely be nude and cooped up with an exceedingly thirsty pint-sized mare. Bearing that in mind, he weighed his options. Even though Cozy hadn’t told him her age, she clearly knew what she was asking for. Shrewdly, he rubbed his chin, considering his choices, until the pony cleared her throat.

“You know,” Cozy mused, continuing to roll about on the mattress, “with my size, you could fuck me like a sex toy…” As a seasoned schemer, it was a worthy piece of bait. She wasn’t sure what Anon had been banished to Tartarus for, nor did she care, because he could be a useful tool and source of entertainment. While she would have preferred a stallion mounting her, she had to admit, the prospect of feeling the man’s hands holding and caressing her was enticing.

“Fuck it, I don’t even care anymore,” Anon sighed, defeated. After everything he’d been through, and all the various creatures he’d plowed, he may as well add a pony to the list. Tossing his towel to the floor, and allowing his semi-flaccid manhood to flop free, he stepped towards the bed.

Cozy’s maniacal grin reappeared, as she saw Anon draw nearer. It didn’t matter if Anon’s resolve had crumbled, or if the human had simply lost hope; either way, she was going to get what she wanted. Flopping onto her back, and letting her head recline off the side of the bed, the world was upside down, as she watched his bobbing prick grow nearer.

“Just fuck my throat raw,” she squeaked.

With the mattress at roughly shin level, likely due to the myriad of different creatures imprisoned, Anon had to sink to his knees. Moving closer, Cozy appealingly opened her maw, as she awaited his tool. Of all the students he’d had a roll with, not a damned one of ‘em had been as outright whorish as this weird little mare. Hell, even Yona had shown some self restraint! But none of it mattered now. Condemned to pony hell with a sex crazed horse; truly, a wry twist of fate.

Craning her neck forward, Cozy kissed the tip of his prick, prior to running her tongue around its head. “Use me,” she muttered.

As tiny as she was, and as off-putting as her innocent act could be, Anon was finding it hard to fully commit himself. Yeah, he’d done some questionable shit before, but this just felt weird. He looked up, as he heard Tirek clear his throat.

“You realize, while she may look like a filly, Cozy did almost conquer Equestria,” the centaur-like beast chortled, gleefully watching from his cage. “Perhaps you should punish her…”

“Wait, really?” Anon rebuked, shocked by the villain’s admission. He kinda figured Cozy had been sent there for some sort of friendship faux pas, much like himself, not attempted world domination.

“Yeah, yeah, yeah,” Cozy growled, taking a break from her ministrations to wave her hoof about. “So I tried to take over Equestria, so what? It’s not like I would’ve done a bad job or anything, just remove any traces of magic from the land, subjugate the populace, and reign supreme as the friendshi-Mmmph,” she was cut off, as Anon thrust forward, filling her gullet with his member.

While Anon may have made some poor life choices, there was no way he’d ever actually hurt somebody. The fact that this precocious mare would try something so heinous practically demanded that he take action. Hunching over, he wrapped one hand around Cozy’s torso,while the other flew to her loin. If she wanted some action from him, and considering her wicked confession, he’d give her what she wanted, but it wasn’t exactly going to be gentle.

As Anon serviced himself with Cozy’s mouth, making sure not to choke her; he kneaded and massaged her marehood, with his left hand. Skillfully, he played with her clit and teased her entrance, feeling her meaty and taut lips wink around his digits. Sensing himself bump against the back of her throat, she gutterally groaned around his length. It certainly didn’t sound like she minded the rough treatment, and she wasn’t struggling or anything, so he wasn’t too concerned. That being said, he was getting frustrated. This was supposed to be some grand irony, as Cozy was undone by her own hubris!!!

With a frustrated grunt, Anon pressed forward, causing his tool to delve into her esophagus. Strangely enough, the tiny pegasus didn’t struggle; although she did writhe around a bit. Readjusting his hands, he plunged deeper, until the filly’s snout bumped against his balls. The sensation of her maw was astounding, only eclipsed by the sight of her throat obscenely bulging outward. In and out, back and forth, he slowly made use of her muzzle. As his gaze crept down her tiny frame, he noticed her engorged and succulent marehood. It seemed that the face fucking wasn’t enough of a punishment for her.

Irritatedly, Anon jammed one finger into the pegasus’ cunt, followed by a second, as he continued with his righteous punishment. Instantly, her voice raised an octave, and her wings reached up to caress his balls. As for her marehood, it was astoundingly snug and warm, much more so than any female he’d ever been with. Between her noises, his digits in her vice-like sex, and her tongue dancing over his length, Anon was in a bit of a spot. No matter how hard he tried to tell himself he was doing this to discipline her, the longer he went on, the harder he got.

Thrusting with increasing force, Anon endured. To his chagrin, Cozy wrapped a wing around her abdomen to tease at her clit, as his fingers probed her marehood. Somehow, even though the muted gagging noises, she was getting off to choking on his length. After a minute or so, Anon realized he needed to switch gears. Releasing the mare, Anon stood and hauled himself from her maw.

As he pulled his shaft from her gullet, she coughed weakly. A strand of pre-cum and saliva dangled between his manhood and her mouth. Dreamily, Cozy looked up at him, while she licked the cocktail of his pre-cum and her saliva from her lips. Surely, she was an insidious and depraved creature, unlike any other. Silently, he scooped her up and spun her around. Grabbing her around the midsection, with both hands, he moved her towards his groin.

“So,” he began, dragging her leaking marehood over his dick, “if I fuck you, will you promise to be friends?”

“I…I...” Cozy stammered, feeling every vein along his shaft caress her clit.

It’d been ages since she’d had any sort of sexual gratification, so the act was tantamount to torture. Although Anon wasn’t the most well hung male she’d ever been with, he was on the larger side of the spectrum; at least, for her, he was. One of the benefits of being her size was that even ‘average’ sized cocks were large, which was an aspect of her nature she deeply appreciated. Still, despite her size, her marehood was well trained, and she had no doubt she could handle the man-creature.

Cozy gasped, shaken from her reverie, as he taunted her entrance. Anon had positioned her so that the tip of his member prodded her gash. “P...please,” she whimpered, wriggling in his grasp. The bastard was pressing it in just enough to let her sense its size, but he refused to fully penetrate her.

“Promise…” Anon mumbled, continuing to torment his cellmate.

“I’ll be a good little pony, I promise now take that faaaa-OH BUCK,” she squealed, as Anon’s length ground into her. Sweet Celestia, if she ever got out of Tartarus, she’d have to remember to make him her personal fuck toy. Lacking the blunt head of a pony stallion’s, his equipment was rounded like a dull spear. Between its shape, and prior his fingering, he delved into her depths with relative ease. Without a medial ring, the infuriating thicker band around a pony’s stallionhood, the man was able to cram damn near the entirety of himself into her, only stopping when his glans pressed against her cervix.

Peering down, Anon had to say, he was impressed. Looking through the crevice of Cozy’s tush, he noticed he’d fit almost all of his tool into her; an impressive feat, considering her diminutive dimensions. Holding her firmly, he pulled the filly off of himself, only to ram her back onto himself. Steadily, he started screwing her, effectively using her like a large, nefarious sex toy. With each plunge, his tool impacted against the mare’s womb, causing her to mewl and writhe in his hands.

“Fuck yes,” Cozy cried, fitfully flapping her wings, while she was rutted. “Fuck me harder! I’ve been such a naughty filly!!!” she wailed, as her marehood was pounded. Clamping her hind legs closed, and flexing her glutes, she exerted additional pressure on Anon’s cock, eliciting a grunt from the man. It was exceptionally rare for a male to directly assault her uterus, and the exquisite juxtaposition of discomfort and pleasure was mind boggling.

The increased tension on his member caused Anon’s speed to quicken, and the power of his thrusts to intensify in force. Even though it slightly impeded his movements, he was spurred to go even rougher than before. Although he wasn’t aware of it, on some level, he found the experience cathartic. In his prior forays into magical creature coitus, he’d never really let himself go full force. Ironically, it was with Cozy, his smallest partner to date, with whom he’d unleashed his full fury. His solemn reverie, however, was broken, as the puny pony spoke up.

“You like this don’t you? Plowing a tiny filly, like some filthy beast! I bet that’s what you’re in here for, isn’t it?” Cozy chided, speaking between plunges of his ungodly dick. “It wouldn’t surprise me if you rutted half of the students at Twilight’s Fr-MMMPH” her derision came to a swift end, as Anon jammed two fingers into her mouth.

“Just shut the fuck up!” Anon snarled. It was bad enough that he’d chosen to screw her, but her little tirade caused something to snap. Supporting her abdomen with one hand, he’d jammed two digits into her flapping maw to silence her. Even though Cozy didn’t seem to mind, given how she was lewdly sucking and moaning around them, it served to quiet her.

Relentlessly, he jackhammered into her; humping forward, while he pulled her to himself. With each plunge, he felt something in his palm, and it took him a second to figure out what it was. He was banging her so hard that his tool was distending her belly, an act he didn’t think was possible. Undeterred by the revelation, he continued to brutalize her marehood.

Slurping on Anon’s fingers, having her insides nearly rearranged by his rough treatment, and being used in such a wanton way, was quickly pushing Cozy to her limit. Her forelegs hung limp, her mind was going blank, and her thighs trembled, while Anon slaked his lust with her body. Tactician though she was, she’d always had a masochistic streak, often tricking stallions much older than herself into having their way with her, but none had truly committed themselves to the task. Every time the head of his manhood bludgeoned her womb, she shuddered, leaving her to drool uncontrollably from both ends.

Under the intense and morally conflicting pleasure of using a living creature as an onahole, Anon gnawed his lip. No matter how much he tried to stave off his impending orgasm, he had to admit, there was something infuriatingly hot about plowing something so small and knowing they were getting off to it. Realizing he wouldn’t be able last long, he gave her everything he had. He’d be damned, if she’d ever forget about pissing off Anonymous and using him for her own carnal amusement!

Pounding away like a man possessed, Anon’s balls slowly retracted. With one final, titanic plunge, entombings as much of himself in Cozy as humanly possible, he came. His tool throbbed, rhythmically pulsating, as a deluge of hot spunk raced up its length. Gritting his teeth, he unloaded into the mare, making sure she got every drop of his spunk.

The influx of Anon’s seething seed instantaneously sent Cozy over the edge. Howling uncontrollably, she climaxed. Strings of saliva hung from her chin, and a cocktail of her orgasmic juices and the man’s cream squirted from her overstuffed cunt. So great was her ecstasy, that her entire body contorted and convulsed, all while impaled upon Anon’s glorious cock. It was unlike anything she’d ever felt, so cataclysmic was her bliss. The entire world, her whole existence, was rapturous pleasure. Fighting to maintain consciousness, Cozy’s eyes rolled to the back of her head, as her screams of exaltation slowly died.

Panting, and still holding the filly on his member, Anon stood. The release of neuro-chemicals had burnt away a sizeable portion of his frustration, which certainly helped, but he couldn’t shake the feeling that something was wrong. Lazily, he looked to his side, and his heart stopped beating. There, on the other side of the barred wall of his cell, stood Twilight Sparkle. His mouth went dry, and the blood in his veins froze to ice, under the baleful gaze of the alicorn Princess.

“H...how long have you been standing there…” he wheezed.

“Long enough to see you despoiling one of the most reviled fillies in Equestria,” Twilight replied, her tone utterly deadpan.

Glancing over to Tirek, as he lazily milked his tool, she wasn’t sure what to think. Either Anon had subjugated one of the worst villains she’d ever encountered, or he was putting on some sort of exhibitionistic show for the centaur who’d destroyed her house/library. Either way, she wasn’t pleased, and Tirek had gotten off to the performance. Clearing her throat, she regarded the man.

“It’s time to go, we need to talk,” Twilight uttered, igniting her horn.

Nodding like an idiot, Anon waddled over to the bed. As carefully as possible, he hauled his swiftly softening length from Cozy’s abused snatch, allowing him to deposit her on the mattress. Sullenly, and with great shame, he retrieved his makeshift toga, and wrapped it about himself, before walking over to the Princess.

“A...Anon,” Cozy sighed, pawing at the fleeing man, causing him to turn, “come back to visit.”

Anon’s fear only deepened, as he looked at the cum drunk filly. He’d really screwed the pooch - well, young mare - this time. Holding up a hand in a silent goodbye, he disappeared, along with the, what he presumed to be, remarkably irate alicorn.

As Cozy watched the two depart, she groaned. Not only had Twilight left with the best lay of her life, but she was now without anyone worthy of her attention. Quietly, she fetched a diary from under the mattress; all while clenching her marehood, to trap as much of the man’s jizz as possible. Unfastening a pen from the book, and finding a clean page, she began to write.

Dear Diary, Anon is just as charming and wonderful as Twilight said. When, not if, WHEN I get out of this hole, I will make him mine…