Candys lesson

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#15 of 2023 Shorts

A drunk Candy gives a girly cross-dressing pony a challenge, which she wrongfully assumes he wasn't man enough to accept. The pretty pony is only too happy to teach his best friends annoying girlfriend a lesson she won't soon forget!


This is a work of fiction. Unless otherwise indicated, all the names, characters, businesses, places, events and incidents in this story are either the product of the author's imagination or used in a fictitious manner. Any resemblance to actual persons, living or dead, or actual events is purely coincidental. All characters are of legal and consenting age, likewise if you are reading this story, you should be of legal age in your respective country.

All characters are my own creation, any resemblance to existing characters is purely coincidental and not intentional, please do not use them without permission. If you would like to use them in a story, please feel free to send me a PM either as Inja on SoFurry or TheRealInja on FA. As always, I am open to new story ideas or situations with existing characters as well.

A trade commission for a good friend, probably not what she had in mind when she sent it to me, but she did give me free reign again, so :P Candy belongs to her owner; Shelby is my own creation to replace the unnamed partner in this RP as SOMEONE didn't get adequate permission for this story based off her RP. Again, this was provided by my favorite spotty feline contributor and conspirator.

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"Heeeey Shelby!" The rather drunk albino crimson snow leopardess slurred as she stumbled through the doorway and into his apartment uninvited. A half-finished bottle of peach schnapps clasped in her hand, her clothing and makeup a little disheveled. Behind her, a somewhat more sober Greg followed with a mostly empty beer bottle in his hand. The large black and tan canine raised his brows apologetically at his best friend for barging in on him like this, knowing Shelby had asked for peace and quiet tonight so he could study. Unfortunately, Candy had other ideas and decided to crash the party, so to speak.

"Great, you're drunk and on a Tuesday night as well" The white pony sighed, rubbing at his temples as his roommate's drunk girlfriend barged into his living room. He and Candy didn't get on at the best of times; having just broken up with his partner a few days ago, Shelby really wasn't in the mood to deal with her shit right now. It didn't look like Greg was about to step in and try control her either, when he settled down in the single seater off to one side and watched his girlfriend annoy the living shit out of his best friend. Greg seemed oblivious to the pleading looks Shelby was giving him, the large canine simply sat sipping on his beer while Candy made herself at home.

"S'fine, I'll just crash here on the couch. Won't even know m'here" she giggled and sprawled out on the sofa he'd just been sitting on. Apparently, she was too drunk to notice her short skirt riding up to reveal the rather obvious camel toe she was sporting, thankfully she was also too tipsy to notice the sudden blush at Shelby's cheeks when he spotted it.

"Candy, I really need to watch this documentary for my biology study. Can't you go sleep it off in Greg's room rather?" Shelby asked as politely as he could, trying to keep the note of annoyance at the curvy feline already hogging most of his sofa out of his voice. Shelby shot Greg another pleading look, but the large canine simply smiled and shrugged his shoulders again without saying a word.

"But it's too early to go to bed, c'mon! I don't bite!" Candy offered with a sweet smile, or at least what she thought was a sweet smile. In reality she was grinning at the pony like a psychopath, if she'd had a bat in her hands, she'd look just like a demented Harley Quinn right then.

"Ugh fine! Just please be quiet and let me watch in peace!?" Shelby groaned in defeat, brushing his fingers back through his long rainbow colored mane, pushing his fringe back behind an ear. The slender white equine brushed his hands along his hips, smoothing out his own short skirt in the process, a force of habit he did when he was stressed. He tended to do it a lot around Candy for some reason, he noted to himself.

Shelby tried his best to ignore Candy, while attempting to take notes of the documentary on the television. Sitting on the opposite end of the couch from her with his legs crossed, one of his hands idly fiddled with the edge of one of his thigh high stockings, or adjusting the sleeves at his upper arms to prevent his off the shoulder top from sliding down too far.

"You know, if you actually had tits, like mine, your top wouldn't keep falling down like that. Plus, your bulge is super obvious under that skirt too!" Candy mocked with a little laugh, reaching out with her foot to grind her heel against the obvious bulge under Shelby's black skirt.

"I'm a goddamn horse, of course there's going to be a bulge" He snorted in annoyance, swatting her foot away from his crotch. "Pretty sure Greg doesn't like you going around touching other guys junk either." Shelby almost growled, once again shooting his best friend an annoyed look; frowning when the canine smiled meekly and shrugged his shoulders without saying a word.

"Pfft, nah. He likes watching" Candy replied with a broad smirk when Shelby shot her a surprised if not skeptical look, but the fact Greg was only a few feet away and no doubt clearly hearing her; still, he didn't deny it. The albino snow leopardess continued to grin at the horse, curling her toes as she began to blatantly rub and massage at his crotch. "But it's not like you'd ever do anything anyway, too much of a pansy to fuck a woman, let alone your friend's girlfriend, right? Do you even like girls, you look like you've taken more dick than even me?"

Shelby grit his teeth as he bit back a cruel retort, the only reason he even put up with Candy was because she was dating his best friend and roommate, Greg. He didn't know why, but she'd annoyed the ever-loving fuck out of him since day one. He just couldn't put his finger on it, it wasn't like she was really annoying or anything either. She was cordial to him most of the time, but he'd seen the looks she'd give him when she thought he wasn't looking. He'd assumed it was just because he was a tall slender stallion whom liked wearing skirts and stockings. Or maybe it was because he died his mane and tail bright colors of the rainbow? Then again, perhaps he just pulled the look off better than her and she was jealous.

"I'll have you know; I've slept with plenty of women, thank you very much!" Shelby snorted, pushing her foot away from his reluctantly plumping crotch. As much as he did not like her, even he was not blind to the fact she was a gorgeous feline. Her curvy figure, the cute pink and red heart shaped rosette spots on her fur, even the long and luxurious white and red striped hair. Even though she was his friends girlfriend, she was a woman to which he had reluctantly pleasured himself to the thought of more than once in the past; after accidentally catching her coming out of their shower in nothing but a towel.

"I call bullshit on that. If you're such a stud, why don't you show me what you can do?" Candy purred playfully at him, narrowing her gaze to a sultry stare. Again, her foot reached out to rest and rub against the obvious tent in his skirt. "Or are you too much of a little bitch to put me in my place?" she challenged with a growly purr accenting her words.

Shelby gave a little chuckle at her words, the foot wiggling in his lap did feel nice admittedly; his rainbow-colored tail giving a little flick beside him in annoyance. However, her words would make his brow lift as he gave Greg a questioning look. Greg in turn simply grinned and nodded his approval to Shelby, much to his surprise. The colorful horse soon turned more to face Candy with a smug grin when he called her bluff, knowing he had his friend's permission to accept. He spoke slowly and clearly, so that the inebriated feline heard his response to her challenge clearly. "If that's what you really want...just got to ask for it, kitten." He replied with no small measure of a mocking tone, knowing how much she hated being called kitten.

"Well, pretty pony; would you do me a favor and pin me down, grab my tail and then fill me full of nice thick pony cock? Fuck me nice and hard until I beg for mercy, right here on this couch in front of my boyfriend?" She teased, her little pink tongue licking along a fang while she stared at him with an inviting gaze. Her foot stirred in his lap, rubbing back and forth along the tent forming beneath Shelby's skirt. It was obvious that she thought this was a simple game of chicken and she fully expected him to blink first, if he did that, she would never let him live it down. She needed to be taught a lesson and put in her place, Shelby couldn't think of a better way for him to do that.

His mind was running a mile a minute, the constant rubbing of her foot against his lap caused a nice bulge to form, his thick pony length plumping up and beginning to rise under his skirt. He hummed in thought a moment before giving a nod. "Sure thing...bitch," Shelby almost growled, giving her a stern glare before he sat up, suddenly gripping the ankle of the foot in his lap to use as leverage to flip her over onto her belly beside him on the sofa. Shelby joined her a moment later, a surprisingly firm but soft hand soon befell the back of her neck, holding the feline in place while he shifted in behind her. Lifting the front of his skirt up and out of the way, tugging his own panties aside to free his thick and heavy cock. Without warning, his firm hand came down with a loud crack to give Candy's plush spotted rump a nice swat, making her mrowl in surprise. "Good kitten," he once more growled softly down at her, quickly getting to work on pushing Candy's own almost matching skirt up about her waist. His hips shifted in closer, angling to let his thick pony prick give a tap against her ass almost threateningly, before he wedged himself between her firm spotted buttocks. Sawing slowly back and forth, between her plush spotted cheeks, Shelby let the albino snow leopardess feel his size for the first time.

Even though Candy initially growled at being rolled over and moved about, as soon as his hand grabbed the back of her neck, all resistance went out of her. Her tail raised almost obediently as soon as Shelby gave her spotted behind a firm swat. With her skirt lifted and her panties tugged aside, Shelby got his first real unobstructed view of her treasures, which soon enough he began to grind his thick cock against. It was only when the feline felt the warm weight of the mustang's cock rubbing against her that she wondered if perhaps she'd bitten off more than she could chew. For a little cross-dressing pony, Shelby was packing a decent length it seemed. Still, Candy was too proud, or perhaps just too drunk to admit defeat just yet; she'd given him the challenge and she wasn't about to back down yet. Especially not with Greg grinning at her and watching from the seat beside them.

Shelby ground his cock back and forth, letting her cunt feel his medial ring bump against her soft pouting pussylips, grinding and bucking against her until she started to press back against him. All twelve inches of hard cock ground and rubbed against her for a few moments, until finally Shelby slowly drew his hips back and pressed his blunted tip to her needy little pussy. Grinding it slowly back and forth against her opening, letting her prepare for his inevitable entry and all that would entail. Slowly the pony started to push himself forward, easing his cock into her slowly, spreading her wider and wider until Candy's snug little cunt reluctantly accepted him with a lewd growl from her. With one hand grasping firmly about the back of her neck, the other rubbed along the graceful curve of her back, following along the line of her spine and over the curve of her behind until he gripped the base of his slowly invading cock. His fingers wrapped about his thick girth, stroking and gripping himself tightly while he started to pull Candy backwards, forcing himself in deeper once the blunt flared head breached inside her sweltering depths. With a pleasured snort at the feeling of heated slickness enveloping him, Shelby closed his eyes and shuddered while pushing forward eagerly, quickly filling his best friend's girlfriend up with rock hard pony cock.

Candy shivered at the feeling of that medial ring bumping against her pouting pussylips, knowing the pony was packing. Sure enough, when Shelby finally pulled back far enough to nudge the blunt tip of his cock up against her little pink pussy, she knew she was about to be crammed full of delicious cock. As soon as he managed to get her opening to reluctantly part and accept his girth, she'd begin clawing at the sofa beneath her, as inch after thick inch stretched her open and filled her to the brim. For such a girly looking pony, Shelby was nowhere near as gentle or reserved as she expected him to be. In fact, she hadn't even expected him to accept her challenge, she'd thought he was gay since the first day she met him! But oh God, how she loved it, the strong grip to the back of her neck holding her in place as a nice thick cock slowly descended down inside her cunt, punishing her in the best way possible. Unfortunately, the couch would suffer a few holes from her claws in response to being so crammed full of cock however, for the moment though, none of them seemed to care.

The pretty pony shoved himself in deeper still, his rainbow-colored fringe falling from behind his ear and partially obscuring his cute done up face. His bright pink lipstick was a little smeared, but his mascara and smoky eyed look was still intact, making for a rather unique scene for Greg to enjoy watching as the girly pony deep dicked his woman. Shelby leaned back to admire how his best friend's girlfriend took his cock, her delicate pink folds stretched about the middle of his fat dick; the mottled pink and black length looking almost too big for the slender feline to take, yet he had a good portion of himself stretching her out already. With only half his cock sunk inside the feline, Shelby pushed further, until his blunt cockhead nudged into Candy's cervix. He knew he'd definitely touched her inner barrier when she made an odd sound and squirmed beneath him, he'd had similar reactions from past partners before as well. The pretty pony shot Greg a smug grin, knowing he'd obviously never reached this deep in his girlfriend before, but judging by the bulge in the canines' pants, he didn't mind that Shelby had managed to do so. With his medial ring once more kissing the stretched felines folds, it was a nice guide point for how deep Shelby could go. He sat up straight again, his free hand grabbed the base of Candy's tail to lift her ass, adjusting the angle of her hips up a little before he drew his own hips back, only to roughly shove himself in nice and hard into the tight feline beneath him. His heavy balls smacked against the backs of her thighs when he gripped the base of her tail and dragged her back onto him, huffing out aloud when he nearly bottomed out inside Candy once more. Her walls felt so heavenly around him, squeezing around his thick prick nicely. His grip briefly left her tail when his hand rose again, only to come down with a firm crack to her toned buttocks and making her yelp. Shelby grinned when he felt her clench and squeeze down around him in response to the spank; looking over at Greg, he noticed the canine was now shamelessly stroking himself out in the open while watching his girlfriend being fucked by the colourful mustang.

This was exactly what Greg had bet her would happen, but Candy had doubted Shelby knew the first thing about sex, let alone fucking a real woman. Greg had bet her that if she gave him even a slight chance, the pretty pony would surprise her. Sure enough, as she lay groaning and squirming beneath him, Candy could feel the pony's blunt cocktip nudge up against her cervix while her pussylips were stretched taut about his thick cock; she was filled to the brim! As soon as he gripped her tail and pulled her back, she was his to do with as he pleased. Her soft little pink pussylips stretched about that fat pony prick as it began to sink in and pull back out of her needy cunt, the feline was so blatantly aroused, there was no denying it. Especially considering how slick Shelby's cock came back out of her every time he bucked into the needy spotted feline beneath him. Every firm swat to her behind made her growl and snarl into the crook of her arm, her inner muscles clenched and squeezed down around his cock while she willingly tilted her hips, further presenting her behind to him to enjoy her.

Shelby shuddered, loving how she clamped down around him while he beat his way in and out of Candy's wonderfully snug cunt. Smacking her ass again, he enjoyed watching her firm spotted flesh jiggle each time he left a rosy handprint beneath her white fur. The pretty pony tugged on her tail as well, leaning back to watch as his mottled cock spread her cunt nice and wide, over and over again. He couldn't help but grin at her boyfriend sitting close by, watching her take so much cock so well as he huffed out mockingly,"Mmnn...good kitten. Yea...take that cock, bitch." Shelby shifted his leg up to give himself more leverage, soon after he began to really hammer home, driving deep down into Candy. His balls swinging, nice and full of his pent-up load, ready to fill her to the brim and more when the time came. He'd not had sex in a couple of weeks since his breakup, he'd even been too depressed to watch porn and jerk off even.

It was all becoming too much too fast, the smacking to her ass, the tugging of her sensitive tail, but mostly the thick cock hammering her snug little cunt hard. It was exactly what she'd been warned about, soon Shelby had Candy mewling and panting heavily while she began to twitch and shake with her impending climax. Suddenly, one of her hands appeared between her thighs when she began to furiously rub at her clit, taking her that last little bit further until she started cumming nice and hard for the pony. Cursing and growling out his name while her body clenched tighter down around the fat cock hammering deep inside her, coating it liberally with her hot slick femcum. All the while she felt the pretty pony's big balls tap against the backs of her fingers strumming her clit so fast, they were almost a blur.

Shelby grinned and leaned back a little while he watched Candy's fingers grind into her clit, his hips not slowing as he stuffed himself into her nice and hard, over and over again. The feeling of her silky walls spasming and squeezing around his cock made the horse grunt and huff, slamming himself in harder still. Eventually he would lean over her back, releasing his grip at the back of her neck, instead shifting higher to grab at her white and red striped hair. With a rough tug back on his new handle, to force her to almost look back and up at him as she came; his hips switched to deep short thrusts, beating her cervix into submission, grinding hard before he pushed forward. Shelby's balls tucked in and up against his body, his cock throbbing and flexing hard just before he came with a loud nicker. The broad and flat head of his cock ground right against her cervix, flooding Candy's womb with all his pent up horsecum, while he tugged her back hard. There was not enough room inside the slender feline for both his cock and all his mess however, soon his hot sticky seed began to spill from her tunnel and down her inner thighs to the couch below.

Candy uttered a few rather unladylike words when Shelby bucked deep inside her and began to cum hard, filling her with all that delicious hot messy cum. She could feel him filling her womb with his seed as he ground down into her, her inner walls flexing and squeezing tightly down around him, almost milking him of every last drop of seed he had to give. Her eyes finally opened and locked onto Greg's own, a bright blush spread through her cheeks as her boyfriend watched his best friend empty his heavy balls into her, she could already feel the mess running down along her inner thighs. The albino snow leopardess hissed when her hair was tugged back while the pony fucked her deep, though she loved every second of it. Shelby was so far from the weak and gentle lover she'd assumed he'd be, if she'd known he was this good, she'd have challenged him sooner!

Shelby continued to grind and buck into her, his cock flexing and pulsing hard while he deposited all he had to offer and more. His hands gripping at her hair loosening, letting her down forward slowly as he sat back on his knees. With both hands free, the pony rubbed over her pert spotted ass, kneading it and grinding forward while he continued to nudge his blunt tip against her abused cervix. "Mmnn... fuck...Good kitten...I can see why Greg likes you," Shelby mocked, winking at the grinning canine now kneeling beside them to get a better look at the aftermath.

Candy purred deeply, a content sound as she gyrated and rolled her hips back onto the cock still buried inside her. She found she rather enjoyed the sensation of him touching her cervix still, none of her other lovers had ever managed to do that before. Even now she could still feel the hot mess spilling down along her inner thighs from her well fucked cunt, her soft lips still stretched about the girthy cock even as it began to slowly soften inside her. The tired feline let Shelby feel her inner muscles clenching and flexing in little aftershocks of her climax. "Okay...I admit, you fuck as well as you dress..."

"I hope you learned your lesson Candy" Greg teased, leaning in to give his tired girlfriend a tender kiss as Shelby lay down atop her, his hips grinding against her behind in slow undulations. "Don't forget, you owe me a threesome, seeing as you lost and all."