The dim lights of the Brass Horseshoe blanketed the pub in an ambient sepia. The waitresses were busting hoof like every Friday night, the university crowd was out in droves looking to unwind from a stressful week. As ponies socialized and flirted around him, one cross dressing unicorn sat by himself at the bar, sipping on his madras. Using his magic to adjust his black knee-high socks, his eyes moved across the room, he could tell he was getting some looks. He certainly didn't mind the attention, he loved the idea of all eyes on him. He certainly couldn't blame them, he had quite the unique appearance. Orange highlights in his lime green mane, a long sleeve fishnet undershirt hugged his raspberry red fur, covered by a band t-shirt a size too large for his petite frame. A plaid skirt completed the outfit, just barely long enough to cover his sky blue panties. Were it not for his more tenor tone of speech, one could barely tell they were looking at a colt.
Out of the corner of his eye he saw a stallion approaching, a pegasus with a letterman's jacket. He took only a moment to memorize the jock's appearance before turning his gaze away, feigning disinterest. “Bartender,” he called out, “Another madras, s'il vous plait.”
“Put it on my tab, Whiskey Ball.” The jock called out, leaning on the bar next to the cross dresser. “Can't make a lovely filly pay for her own drinks.”
“Oh, merci.” He giggled, covering his mouth with his hoof. “But please, don't call me a filly. I simply like the clothes.”
“Of course, I hope I didn't make you feel uncomfortable.” He grinned, examining the boy from head to hoof. “The name's Tailwind, I take it you're a french major?”
“I'm afraid I'm not a student.” He corrected, taking a sip of his new madras. “I'm Sorbet, I run an ice cream parlor up the road. I just like the way french rolls off my tongue.” He licked his upper lip in emphasis, looking over at the pegasus.
Tailwind couldn't help but blush at the flirtatious cross dresser. Chuckling gently, he leaned in closer to the boy, brushing his amber mane from his face. “An ice cream parlor, huh? Is your cutie mark an ice cream cone?”
“It's a secret.” He teased, smiling at the sports colt as he tapped him on the nose. “If you play your cards right, maybe I'll show it to you later tonight.”
“Sounds fair.” Tailwind smiled, and gestured to Whiskey Ball behind the bar. Whiskey Ball nodded back, and began mixing a drink for the student. “How long have you been running your own business?”
“It's only been a couple years.” Sorbet sipped at his drink, watching as the bartender set another drink down for Tailwind. “So you're a student? What do you study?”
Tailwind smiled and took a sip of his drink, sighing softly at the taste. “I'm mostly studying weather sciences in terms of classes, but I'm on a sports scholarship. I'm the track team's trick flyer.”
“Trick flyer, huh? Do you have any signature moves?”
“Of course.” Tailwind grinned at him and tapped his nose. “Play your cards right, maybe I'll show you them later tonight.”
Sorbet blushed as he felt the colt's hoof on his nose, giggling gently at the mocking response. “Cute, athletic, and quick witted. You're the full package, aren't you Tailwind?”
“Would it be in poor taste to make a 'package' joke?” Tailwind grinned, leaning against the bartop.
Sorbet's giggles persisted at the colt's joke, until his laughter turned to a yawn. “Pardon moi, I suppose I'm getting sleepy.” He wrapped his hoof around Tailwind's, smiling gently. “Would you, par chance, like to walk me home?”
Tailwind smiled as he downed the remainder of his drink, taking the colt's hoof tightly. “I'd love to.”
Sorbet kicked back the door to his bedroom, leading Tailwind by the lips through the doorway. Their tongues danced and wrestled with each other, the pair breathing heavily through their noses, their bodies warm. Sorbet groaned at the feeling of his cock aching to break free of his underwear, Tailwind groaned alongside him, pressing his muzzle closer to the cross dresser’s as he shut the door behind him with his hoof. Sorbet pulled back from the kiss, a strand of saliva keeping their hanging tongues together. His horn lit up as his magic slowly parted the zipper of Tailwind's jacket. “Get on the bed.”
Tailwind grinned as he brushed against Sorbet, bumping his flank playfully against the unicorn's. He slipped free of his jacket, letting his silvery grey fur free. Sorbet smiled at the pegasus as he slipped out of his shirt, along with his fishnet. He eyed Tailwind, who was watching intently as the cross dresser lifted his forelegs up onto his dresser, his rear facing the erect stallion. Using his magic, he released the button on the skirt, and slowly shook his hips until the both the skirt and his socks fell down to his hooves, now standing in just his blue panties. “You still wanna see my cutie mark?”
Tailwind rolled onto his side with a smile on his face, watching the colt's shaking hips with deep arousal. “Of course, let me get a good look at it.” He licked his lips, watching intently.
Sorbet grinned and turned his head away, his forelegs still resting on his dresser as his horn lit up and his magic took hold of his panties. He bit his lip as he slid his panties down slowly, giving his playmate a look at his toned flanks and puckered tailhole. After another moment of teasing and shaking his hips, he finally slid his panties off his back legs, spreading wide to give a good view of his hanging erection and tailhole, his cutie mark on display. An elegant looking ice cream scoop, with a solid handle blending green, orange, and the red of his fur. “So, what do you think?” he asked, dropping onto all four hooves. He approached the bed and climbed on top of the sports colt, smiling down at him. “Is it everything you were expecting?”
The track pony smiled up at the feminine unicorn, rubbing his flank gently, his hoof brushing back and forth across the ice cream scoop, the cross dresser’s cock resting on his stomach. “Yeah, it's very cute. Just like you.”
“That's the cheesiest thing you've said all night.” Sorbet told him, leaning down and kissing him deeply.
The two rolled their tongues against each other, Sorbet rubbing his flanks against the groaning Tailwind's member. He could feel the warm pre dripping on his flanks as he opened the dresser with his magic, retrieving a bottle of lube. Drizzling it down the jock's flared tip, Sorbet began to rub the lube all across his partner's cock with his thighs. Every grunt and groan from Tailwind made the ice cream pony's body heat up.
Suitably lubed, he groaned as he pressed his tailhole against the flared tip. Tailwind echoed the groan as the unicorn lowered himself slowly onto his stallionhood, feeling every inch penetrate him until he was halfway down the shaft. Taking a moment's pause to get used to the girth, Sorbet broke the kiss and began to bounce slowly, letting out soft moans as he slid up and down on the student's length.
Tailwind laid back as his partner got into rhythm, moving his forehooves to hold the colt's flanks, helping to guide the unicorn up and down on his shaft. The pair moaned loudly, feeling flesh against flesh as their pace sped up. Tailwind began to thrust up into his partner, eliciting excited squeaks and moans as their hips began to connect and slam against each other.
Sorbet sat up, supporting himself with his hooves on Tailwind's stomach. His long, slow ride escalated to quick, rough bounces on the base of his partner's cock. He fought back drool as he rode his partner, feeling Tailwind's every thrust up with his bounce down, they were in perfect harmony. “mph! Spank me!” Sorbet yelled out, shaking his hips against Tailwind's forehooves.
Tailwind was quick to respond, and all too happy to reel his hoof back and strike the horny cross dresser right over his cutie mark. The loud smack and groan from his partner excited him more, motivating him to continue the spanking, striking the colt over and over with painful precision. Thankfully, with Sorbet's red fur, the blush of his bruises were barely visible.
Every strike of the hoof caused Sorbet to squeal and moan and whimper like a chastised school filly, every stroke making his dick throb, his tailhole tighten. He could no longer keep himself from drooling, his saliva running down his chin and neck, dampening his fur. He kept his pace, bouncing and moaning on the colt's hard member. He could feel the student's dick throbbing, he knew he was getting close.
Tailwind could feel it, too. His balls churned as he thrust into the unicorn, giving him careful strokes across the flanks, switching sides and frequency, he kept the colt guessing where the next swat was going to land. Unable to hold himself back, he pulled both hooves back and struck Sorbet on both of his flanks, holding him tightly in place, his tailhole at the base of his cock. With a loud moan and a hard throb he released, filling his partner with rope after rope of his thick seed.
Sorbet let out a passionate whimper as he felt the semen invading his tailhole, shaking his hips gently to milk the jock dry. Slowly, he slid himself off the sensitive dick, giggling at the moan from the pony below him. Dripping jizz from his tailhole, he took a moment to bask in the afterglow. He looked down at Tailwind, who lay limp below him. He was panting and sweating, with his hooves splayed out. Sorbet giggled as he levitated the lube over. Spreading some onto his hoof, he began stroking his pre dripping cock. “Don't tell me that was enough to exhaust a university athlete.” he teased, sliding back off of the colt's lap. “We're only halfway done.”
Tailwind stared down at the unicorn between his legs, trying to catch his breath. He blushed deeply, letting out a groan as he felt his partner's cock against his tight tailhole. Sorbet bit his lip as he thrust his lubed dick forward, feeling the tight ring hug his length. “Damn, you don't get fucked a lot, do you?” He strained to penetrate the colt, going slow to let his ass grow accustomed to his girth. “It's a good thing I'm smaller than you, a dick your size would split you in half.”
Tailwind shut his eyes and moaned loudly as he felt his tailhole stretched. His mind swam with intense feelings of pain and pleasure. He felt his erection return as the cross dresser filled him with half his length. Wasting no time, Sorbet began thrusting, in and out of the colt beneath him. Tailwind moaned loud, his back arched and his legs spread wide. “Oh Celestia, don't stop moaning, every little sound you make is making my cock throb.” Sorbet smiled down at the moaning colt. “It feels good doesn't it? Being on the bottom?”
Tailwind nodded, blushing up at the grinning unicorn, his body tensing as he felt every hilting thrust into his virgin tailhole. Waves of pleasure washed through him in what felt like hours, though really just a matter of minutes, until he felt Sorbet's final thrust, a powerful throb, and a spreading warmth flooding his ass.
Sorbet's body tensed as he came, his tongue lolling out of his mouth as his hips bucked with each rope he shot into the pegasus beneath him. Once he regained control of his body, he slid his limping cock slowly out of his partner's ass before rolling to the side, his back facing him, his hooves hanging partially over the side. “Alright, I've had my fun.” Sorbet told him. “You're free to g-”
His thought was cut short as he felt a pair of hooves wrap around him, Tailwind's stomach against his back. Turning his head back, he saw the pegasus, exhausted and snoring. He was out cold. Sorbet smiled at the adorable jock. Shuffling back, he pressed himself against Tailwind, he could feel his partner's breath in his ear as he shut his eyes and drifted off to sleep.
Sorbet groaned as the alarm sounded from the bedside table. Slamming his hoof down on the snooze button, he let out an audible yawn. He sat up carefully, stretching his legs out. After a moment to wake up and get his surroundings, he noticed the empty bed. “Guess he decided not to stick around.” he sighed, a spice of disappointment in his voice. “Oh well, sa perte.”
Well awake, Sorbet made his way out to the main room of the apartment, over to the tiled kitchen and straight for the coffee maker. As he approached the counter, he paused, staring at the coffee in the pot. In the moment of silence, he also caught the sound of the shower running in the nearby bathroom. “I guess Apollo had an early morning reading.” preparing a mug with his magic, Sorbet went over to the bathroom door and knocked as the sounds of the shower disappeared. “Thanks for making coffee.”
“Don't mention it.” an unexpected voice called out from the other side of the door. A few moments later the knob turned, revealing a damp Tailwind amongst the steam from the shower. “It's the least I can do after last night.”
Sorbet looked at him with a bit of shock, taking a step back from the door. “O-oh Tailwind, I thought you had gotten up and gone home.”
“Well, that'd be pretty rude of me.” Tailwind smiled as he dried off his feathers with a towel. “I'm not really the type to sleep and bail.”
Sorbet continued to stare at the colt, who smiled back at him. The two looked at each other for a good few moments, before Tailwind broke the silence. “Did you...need to use the bathroom?”
“What?” Sorbet snapped out of his trance, pausing at the question. “Oh, yeah. I need to shower, I'm really gross and sweaty from last night.”
Tailwind trotted past the blushing unicorn, bumping flanks with him as he did last night. “Well, it's all yours.”
“Oh, thank you.” Sorbet let out a squeak as their flanks bumped together, stepping onto the bathroom tile. “Help yourself to some breakfast if you'd like. You're free to raid the fridge.”
He closed the bathroom door without waiting for a response, still blushing as he stepped into the shower and slid the glass door closed. Sorbet's mind was swimming, he wasn't used to his bar hookups sticking around, he wasn't used to anyone sticking around. For a while, he sat under the hot water, trying to figure out the situation. It wasn't long, though, before the hot water turned cold, and he was forced to finish washing and climb out, or freeze to death.
After drying off and retreating from the bathroom, Sorbet was faced with another surprise. The smell of blueberries and butter was in the air, a now dry Tailwind was in front of the stove, he had already made two stacks of pancakes, and was working on his third plate. As the door to the bathroom closed, Tailwind turned his attention to the unicorn standing stock still, dripping on the hardwood floor. “Hey there, I made blueberry pancakes, come dig in.”
“Uh, thank you.” Sorbet approached slowly, stepping up to the marble bartop.
Finishing the last of the plates, Tailwind slid the freshest plate across the table to the ice cream pony, taking the second plate for himself and sitting across from him. Sorbet sat in awkward silence with his hookup, eating the pancakes quietly. “Do they taste okay? I don't really cook for myself much.”
Sorbet nodded slowly, looking across the table at him. He couldn't help but smile at the jock's hopeful look. “Yeah, they're good. A little burnt in some places, but not bad.”
“Thanks.” Tailwind took a bite out of his stack, the two exchanging the occasional glance between each other as they ate.
Once the plates were empty, Sorbet was quick to levitate the plates to the sink. With no food buffer between them, the two simply sat awkwardly and shared occasional glances. “Well, I should get going.” Tailwind finally spoke up, trotting toward the door. “It was nice meeting you Sorbet.”
Sorbet nodded slowly, his mind was racing, his cheeks were a deep, rosy red. “W-wait.” he stepped around the counter, opening a drawer and levitating a flier over to the colt. “Here....If you bring this into my store, you can get a free scoop of any classic flavor.”
Tailwind looked down at the coupon for a moment, the smile returning to his face as he slipped it under his wing. “Is that your normal routine? Whoring out guys for free ice cream scoops?”
Sorbet's blush grew deeper as he tried to hold back his giggles, to no avail. “Yeah that's me, I fuck guys and pay them in coupons.”
The two began to laugh, smiling at each other. Finally, as the laughter died down, Tailwind leaned into the blushing unicorn, and gave him a kiss on the lips. “See you around.”
Sorbet stared at the colt as he turned around and left, putting a hoof to his lips with a smile. “Well, that was interesting, who was your friend?”
Sorbet jumped as he heard a voice from behind, quickly turning on his hoof to see a silvery purple furred unicorn leaning against the counter with the last plate of pancakes in front of him. His mane and tail were a deep midnight blue, his cutie mark three tarot cards overlapping each other. “Apollo, don't scare me like that!”
Apollo grinned and slipped a blueberry past his lips, leaning with his front hooves on the counter. “I certainly wasn't trying to be, I practically stomped across the room while you were making googly eyes.”
“Va te Faire Foutre!” Sorbet scoffed, his full face six tones redder than normal. “Hey, can you do a reading for me?”
“After one night?” Apollo grinned, trotting up to his blushing room mate. “Who in the world was he?”
“He's.....interesting.”