A Perverse Proposition

by Some Leech

Rating: mature
Tags: Porn, Button Mash, Fetish, Rarity, Rumble, Sex, My Little Pony: Friendship is Magic, Anthro
Length: 2270

Rumble and Button Mash get caught with their hands in the cookie jar.

Caught peeping on Rarity, Button and Rumble find themselves in quite the predicament. While they'd fully expected to get reamed out by the mare, it wasn't the mare that would be doing the reaming...

Author's Note: Everyone in this story is of age

Kinks Include: Male on Male, Reluctantly Gay, Exhibitionism, Crossdressing, Anal, Threeway, Bi-Curious Boys, and a Messy Finisher

Artwork by Phyll

If you want to help support me, I have a Tip-Jar/Patreon HERE

Published 2022-01-19 21:10:04 UTC
Last updated 2022-01-19 21:10:04 UTC

Boys Will Be Boys

“Are you serious?” Button bleated, balling his fists and glaring at the svelte unicorn.

“Yeah, I mean, it’s not like we were doing anything that bad!” Rumble protested. Crossing his arms and knitting his brow, despite the blush in his cheeks, he averted his gaze from the mare.

“Colts, really, what would your parents say if they found out you were peeping on a defenseless mare?” Rarity sweetly inquired, trotting around the duo.

Both the young stallions had been caught peering through the seamstress’ window while she was changing. The behavior was unbecoming of anyone, let alone a pair of high school seniors. Instead of going out and trying to find a young mare their own age, they’d caved to their voyeuristic tendencies and been caught with their hands in the metaphorical cookie jar.

Thankfully, upon being discovered, Rarity hadn’t immediately alerted the authorities. Demanding they enter her shop for a talk, the delinquent duo were left with perilously few options. If she went to the cops or - Celestia forbid - their parents, they’d be done for. Seeing no other choice, they followed her inside and prepared themselves to be well and thoroughly reamed out.

“Now then, since you two seem a bit pent-up, I believe I have the perfect exercise for you,” she tutted. Turning and sauntering to the back of the shop, she beckoned for her guests to follow.

The young stallions looked to one another, shrugged, and followed along. So long as she didn’t rat them out, they’d have to put up with whatever punishment she had in store for them. It was only after they walked past the curtain and saw her holding an outfit in her hand did they realize just what sort of pickle they were in.

“Um…” Rumble began, shifting uncomfortably, “what exercise is that?”

“I’m so glad you asked, Darling! Come now, we haven’t a moment to lose!” Rarity hummed, sauntering forward and taking the pegasus by the wrist. Without another word, she trotted off and hauled the surprised stupefied lad into a side room. Once she had him inside, away from his friend, she closed the door and grinned over at him.

Handing him an outfit, she proceeded over to a vanity sat to the side of the small chamber. “Do be a dear and put these on,” she instructed. “I’ll prepare the other arrangements.”

Unsure of what to say or do, Rumble numbly nodded and began doing as he was told. As far as he saw it, he had to do what she said. Turning his back to her, to give himself some modicum of privacy, he steadily undressed. Once his clothes lay heaped on the floor, he gave himself a better look at the articles she’d given him.

Stockings, a garter belt, lace choker, and a sheer white nightie were not what stallions his age would normally wear under any circumstances, yet he slipped them on regardless. The only reasoning he could think of was that Rarity was playing some perverted joke on him, perhaps to get even for peeping on her. Regardless of whatever strange purpose she had, he quickly adorned himself in the salacious getup, covered his nethers as best he could, and turned to face her.

“Come right here, Darling,” she murmured, waving him to herself. “Just close your eyes and I’ll finish up with you.”

As Rumble timidly stepped over to her, he only eventually noticed the array of makeup on the vanity. It didn’t take a genius to figure out what she had in mind for him, but that’s not what troubled him - no, his real anxiety came when he realized just how hard his heart was beating. As her brushes and tools glided over his face, he struggled to conceal his growing erection.

Be damned if he could explain why being prettied up was getting him so excited, but it did so nonetheless. As her hands finally departed, he heard her step back. Without being asked, curious as to exactly what she’d done with him, he peered out at his reflection. His eyes widened in shock, his jaw hung open, and his stallionhood twitched uncontrollably at the sight of himself. If he hadn’t known better, he could swear he was looking at a slender young mare.

“It’s not my best work, but there’s no time to waste!” Rarity huffed, taking the lad’s hand and dragging him back towards the other room. “I’m sure your friend will love your new look.”

Almost as if he were in a trance, the pegasus obediently trailed along beside the seamstress into the backroom of her shop. As they entered, Button turned and immediately went rigid in more ways than one. The brown earth pony’s pants tented and he stared in wide eyed wonder, gazing at his now strikingly effeminate friend.

Blatantly ignoring the two, as they gawked at one another, Rarity trotted over to her drafting desk, plucked a bottle from the wooden surface, and handed it to the stricken stallion. “Here, you’ll be needing this.”

Doing a double take at what he’d been handed, Button’s eyes flew to the unicorn’s face. “Is...is this lube?”

“But of course! You’ll be needing it when you rut your friend there!” the mare giggled, nonchalantly pointing to a nearby futon. The pair of classmates stood mute, processing or possibly dumbfounded by what they’d just heard, leading her to sigh. “It’s a simple concept really. You both clearly need some relief, so I’ll teach you how to do it with one another. Rumble, get on the sofa and present yourself as a proper mare should. Button, get undressed and get ready to show your mare a good time.”

Compelled, following his impulses, Rumble wheeled around and casually moved towards the small bed. Though he was having a hard time wrapping his head around everything that was happening, he was well beyond the point of caring. He’d been horny before Rarity had busted them, so the bizarrely hot combination of being gussied up and commanded by the demure mare pushed him well past the breaking point.

Nearly scrambling out of his clothes, eager at the prospect of getting some action, Button slipped glances to his friend’s immaculately presented rear. Honestly, given the hormones raging through his system, he couldn’t care less about if he’d be bedding a stallion or mare. As he kicked his shorts aside and wriggled out of his t-shirt, he slathered his turgid cock with the slick, gooey substance.

“Comfy?” Rarity asked, easing herself onto the mattress beside the pegasus. Peering over at Button, seeing the lad getting into position, she affectionately smiled to the lad’s face. “Take a deep breath and do try to stay relaxed.”

Shivering, feeling his friend grab his hips, Rumble gulped. It was all he could do to screw his eyes closed and take a shuddering breath, as he heard his classmate shuffle behind him. Everything was just happening so fast! One minute, he’d been stealthily watching a mare undress - the next, he was wearing negligee and getting ready to be plowed. Gnawing his lip, feeling the blunted tip of his friend’s tool press against his pucker, he shivered.

“Button, take it nice and slow for your mare - it is her first time,” the unicorn sweetly intoned. Noticing that the pegasus was far too tense for what was to come, she put herself to work and caressed his back and thighs. “Trust me, you’ll love it.”

Sinking his fingers into his friend’s waist, Button steadily plunged into Rumble’s upturned behind. The sensation was divine - hot, snug, and better than anything he could have imagined. While he’d fantasized about plowing someone’s ass, the act itself outshone his wildest fantasies. Without fully realizing it, caught up in the moment, he started steadily humping away.

While he had not expected to have a dick in his ass that afternoon, Rumble couldn’t say he was fully opposed to the experience. It felt odd, but not unpleasantly so. As the seconds dragged on, being screwed by his companion and lovingly fondled by the seamstress, what little discomfort he had withered into an unfamiliar sort of bliss. It wasn’t long before he was rocking back to meet Button’s thrusts.

“Such a good mare,” Rarity cooed.

Rolling onto her back and shuffling beneath the pegasus, she peppered his delightfully flat chest with kisses - that was, until her lips graced one of his perky nipples. Suckling upon the delicate bud of flesh, hearing a whimper escape from him, she unabashedly reached between her legs and began rubbing her marehood. With the two young stallions enjoying themselves, she saw no reason why she couldn’t have a little bit of fun herself.

Bit by bit, Button delved deeper into the pegasus’ delectable rear. From his vantage, plowing his classmate doggy style, he couldn’t even tell he was railing a stallion. Between Rumble’s slim figure, the feminine outfit, and the soft moans, it was almost like he was doing a mare! T view, sensations, sounds, and the fact that he could perfectly watch Rarity getting herself off, caused his excitement soar to unimaginable heights. Shuffling forward, yearning to sink all of himself into his mate, he drove his medial ring into the pegasus’ taut hole.

As the girthy band of flesh Popped into his tush, Rumble groaned whorishly. He hadn’t so much as touched his prick, but he felt absolutely amazing. Far more intense than any sort of masturbation he’d tried before, the act of being bred outshone any sexual act he’d ever had. His legs trembled, his heart thundered in his chest, and he pined for more.

Glancing to the side, Rarity noticed Rumble’s stallionhood dripping pre-cum to the sheets below. Though there was some temptation to stroke him off, or possibly to give him a blowjob, she abstained. She hoped that she wouldn’t need to pay that particular part of the pegasus any attention - after all, if he was leaking that hard after only a few minutes, he probably wouldn’t need any direct stimulation to get off.

As she sank two fingers into her meaty snatch, she redoubled her efforts. Reaching up with her free hand, she delicately twisted and tweaked his free nipple. There was something just so delicious about watching a stallion embrace their marish side - especially if she was lucky enough to get involved. Suckling upon his teat and bucking into her hand, she moaned lustfully to herself.

Rutting the femcolt harder than ever, with his plump nuts slapping against the pegasus’ backside, Button playfully slapped his friend’s rump. The move wrought an immediate and profound consequence, leaving Rumble to mewl out and clamp around his pistoning length. Startled with the revelation, he issued a second smack and grinned to himself.

The stimulation of it all was nearly overwhelming for Rumble. The unforeseen pleasure of being fucked, the sensation having a mare play with his chest, and the slightest tinge of pain from the spankings wreaked havoc upon his delicate heterosexuality. Some part of him embraced it, knowing it was something he would never get with a mare, and spurred him to meet his partner’s thrusts. Before he knew it, he was throwing his ass back like a needy filly on prom night.

Similar to the sensation of a building climax, yet different than anything he’d felt before, a peculiar warmth built within his abdomen. Somehow, despite the sensation being completely new, he knew what it meant. Like it or not, as astounding as it was, he was quickly reaching his limit. Pulling out all the stops, he desperately moved in tune with his mate.

Having lost what little self-restraint he had some time ago, Button wasn’t fairing much better than his friend. His balls snuggled up to his groin, preparing to unleash their fertile load, as his hips became a blur of motion. Gritting his teeth, trying and failing to halt the inevitable, the dam burst. Hilting himself as deeply as possible, he unloaded in the pegasus’ backside.

The influx of hot, thick foal batter pouring into Rumble was too much to bear. Howling out and arching his back, he reached his breaking point. His stallionhood, unmolested throughout the entire ordeal, gushed and lewdly sputtered his cum to the blankets below. Awash in a sea of ecstasy, uncaring about the fact that he’d been so brazenly despoiled, he only just kept himself from collapsing.

Moments after the youths peaked, Rarity did the same. Her marehood clenched hungrily around her fingers, dribbling climactic juices down the cleft of her alabaster rear, while she brayed out in rapture. Experiencing the moment when two stallions caved to their urges was simply divine and far surpassed being bedded by a stud. Feebly hauling herself aside and out from under the pegasus, she heaved air into her chest.

With the unicorn cleared from beneath him, Rumble flopped to the bed. Button’s tool slipped from his battered pucker, painting his lower back and slate grey buns with the final shots of jizz. Panting, feeling the spunk leak from his hole, he struggled to comprehend what he’d done. Surprisingly enough, despite the impulsive nature of it all, he hadn’t the slightest shred of regret.

“T...that was so fucking hot,” Button wheezed, wiping the sweat from his brow. Like his friend, he felt no shame from the lusty encounter.

Glancing between the pair of students, licking the syrupy juice from her whetted fingers, Rarity smiled. “If you want, after you’ve both had a moment to recuperate, I wouldn’t mind finding a dress for Button…”