S.L - The Pretty Boy

Author's Note: This is a standalone story, part of a series of short one-shots I'll be doing alongside my long ongoing series. This one will feature gender bending and queerness. This is a smutty fantasy so please do not read if you want realism. All characters in this story are 18 or over.

This is part of the 'Sapphire Lane' universe which is a collection of various series all set on Sapphire Lane, or at the nearby Ginerva Academy and Violet Liberal Arts College, each lesbian related but exploring different kinks. Each series is standalone but features cameos and potentially crossovers with other series.

The Story

"Come on Casey or we'll leave without you!"

Casey, sat on the loo, heard her roommate Mitena shout through the bathroom door.

"Just a second." Casey called back. She finished peeing, wiped herself, then pulled up her black jeans, being a girl who rarely wore a skirt. She grabbed the can of beer she had balanced on the sink, finished it off with a swig then dropped it into the bathroom bin though knew Mitena would be mad to find it discarded there.

She quickly checked herself in the mirror, smiling back at herself. Casey, 20 years old, was the definition of a gamine with her playfully boyish charm and pretty face, with thick eyebrows and freckled cheeks and nose, framed by her short curly brown hair. Her body was slim with slender legs, small butt, and slight breasts, pretty much just nipples, that were invisible under the loose white vest she was wearing.

Her roommate Mitena was waiting outside with Zoe and Alison, who were two girls who lived in the same dorms as them, as well as Ritu who lived with her family on a road called Sapphire Lane in the suburbs near to the college. The five of them were all students at Violet Liberal Arts College, an all-female place of higher education that was large enough to offer diverse faculties and courses, whilst feeling small enough that you felt like you knew all the other students, even if it was just by sight. Many of the college students lived in dorms on site, though a few lived in privately rented houses or, like Ritu, with family in the surrounding area.

"Come on, or we'll miss last admittance!" Mitena said, always acting frustrated with her dawdling roommate though Casey knew the girl was exaggerating her annoyance. She was of Native American ethnicity, with light brown skin and hazel eyes with epicanthus, with a slim body dressed in jeans and a crop top that exposed her midriff, showing off her flat tummy and pierced belly button. Casey wasn't sure if she had ever seen the girl dressed without her midriff on display.

Mitena led the way with the other girls following, Zoe and Alison with plastic cups which they sipped the last of their vodka from, whilst Ritu, a girl of Pakistani heritage, smoked a cigarette. It was Friday night, and the five girls had had pre-drinks together in their dorm's lounge and, now sufficiently tipsy, were being hurried along by Mitena as the queer bar, Club Rainbow, they were heading to didn't omit people after 11 o'clock. Club Rainbow was a short walk from the college, and was where a lot of the students hung out if they wanted to dance, drink, and listen to loud music but didn't fancy making the trek to the bigger clubs in city centre.

The place was packed, as normal for a Friday night, and the five girls squeezed their way through the crowd to the bar, getting some shots. "So, are we going to find you a girlfriend tonight!" Ritu shouted over the loud music.

"I wouldn't turn one down!" Casey laughed. Earlier on they had been playing a drink game with Zoe daring everyone to take a sip for how many times they had masturbated that week. Casey blushed as she took eight sips, having had a few classes cancelled that week and feeling a little horny lately so pleasuring herself to pass the time, but this had been significantly more than any of her friends, so they had all concluded the freckled brunette needed to get laid.

Casey didn't disagree with this conclusion as it had been quite a while since she last slept with a girl, the last one being Nora, a Chinese-American tomboy who took a pottery class which Casey had briefly attended. She had slept with Nora a couple of times, but the girl was now 'officially' dating someone, and Casey, though daydreaming about several girls she shared classes with or saw in the study area or the canteen at breakfast, hadn't pursued anyone since.

"What about her!" Alison said, pointing over at a girl on the dancefloor which Casey thought she recognised from her poetry class, called Mackenzie or perhaps it was just Kenzie... The girl was blonde and petite with an elfin face, bright lipstick, a pink miniskirt and crop top which was pink again, only a darker shade.

"Far too much of a girly girl for me! She looks like the type to still have her bed filled with cuddly toys!"

"Hey!" Alison said faux-outraged, being a girl who still slept with a teddy.

"How about you just pay Mitena to do it?" Ritu joked, referring to Mitena's new part time job working for Bianka's Escorting Agency, where she had already satisfied the needs of a handful of lesbian clients.

"I'll give a friend discount!"

Casey knew Mitena was joking, but couldn't deny she found the Native American girl attractive despite the thought of sleeping with her college roommate and friend feeling a little incestuous.

"Let's just go and dance!" Alison said before Zoe could get the attention of the bargirl to buy more shots, and the five girls wove through the crowd until they were in the midst of the dancing. After a couple of songs, Casey noticed a girl dancing nearby, part of the crowd but seemingly by herself. She was slim with pale skin, a thin face with a pretty nose, and wavy black hair in a short pixie cut. She was dressed in a blue denim shirt, with no visible curve of breasts, and skinny black denim jeans on her slender legs.

"That's the one I want!" Casey told Mitena, nodding in the girl's direction so her friend could take a look at who she meant.

"Go for it!" Mitena encouraged her, and Casey, who was certainly a little drunk otherwise wouldn't have had the confidence to just approach a stranger, danced her through the crowd, stooping down to swipe up a discarded plastic cup. She danced her way closer to the girl until they were side by side. Despite her tipsy confidence, Casey was a little more nervous now she had left her friends and was actually by the girl, but she thought 'what's the worst that can happen' and moved to brazenly dance with the girl.

The girl looked a little surprised but didn't try and move away but continued dancing until she was moving in rhythm with the Casey, and laughing at the freckled brunette's goofy dance moves.

"I hate this song. Let's go get a drink!" Casey shouted over the music as a new song started, pointing at the plastic cup. "Come on, I'll buy!" Casey dropped the cup and took the girl's hand, pulling her through the crowd towards the bar. She ordered rum and coke then tapped cups with the slender noirette.

"So do you go to Violet's, I haven't seen you around campus before..." Casey asked, thinking she'd remember if she had seen the girl before, always being on the look out for her type which combined tomboyishness with femininity.

"No, I'm a barista!" The girl shouted back over the music.

"Wow, involved in any exciting legal cases?" Casey asked but couldn't keep a straight face, laughing at her dumb joke, with the girl chuckling too. "My name's Casey by the way."

"I'm Caidan." The girl stuck out her hand which Casey took but, with confidence that surprised herself, used it to pull the girl close rather than shaking it. She kissed the girl's lips gently, with Caidan returning the kiss after she recovered from her surprise at the brunette's directness. It was the first time Casey had kissed anyone since Nora, and she enjoyed the feel of the girl's soft lips on her's, and the tenderness between them as the kiss grew deeper. She brushed her hand over the girl's cheek then ran her fingers through her black pixie cut, liking how the short wavy hair felt between her fingers. She felt Caidan's hand caressing down her back, and was excited to feel it softly grope her denim-clad butt.

"Looks like Casey has scored!" Ritu pointed from the dancefloor, glimpsing her friend making out with the girl near the bar.

"I might need to crash in your room tonight! Mitena laughed, speaking to Zoe and Alison.

"You're welcome to the floor, I hear its very comfy." Alison teased.

"Or perhaps I'll steal the dorm's couch from Ritu!" Mitena said. Ritu, due to living off campus, often crashed on the couch in the dorm's lounge area after a night out.

"Is that definitely a girl she's kissing?" Zoe asked, peering through the crowd.

"Think so, she looks like one... must be as Casey is a total lesbian..." Alison said, though was a little uncertain now Zoe had mentioned it.

Casey poked her tongue between the girl's lips as they kissed deeply, and felt excited to feel the wet tip of the girl's tongue meet her's. Their deep kiss, open mouthed, turned a little sloppy as they both eagerly involved their tongues.

"I think we need to get a room." Caidan said after the kiss broke, blushing a little as they had been making out in the middle of a bar, though such displays of public affection weren't too unusual in Club Rainbow.

"I think that's a fantastic idea!" Casey laughed.

****

Caidan had returned to his apartment after a long day's work at a coffee house, and after making himself a bowl of ramen for dinner, messaged around the few friends he had in the city, having only recently moved there, to see if anyone wanted to go out.

He was disappointed to find everyone was busy, as after a long week of work he wanted a night out rather than just being stuck in his apartment for another evening, especially a Friday night.

'Suppose this means I can get up early tomorrow and go to the gym... perhaps I could use this opportunity to have a healthy weekend of me time... or I could just go to Club Rainbow by myself, not to drink but just dance for a few hours as it's a friendly vibe and probably be still fun without friends...' Caidan thought, never having gone out to a bar or club by himself before, but the queer bar Club Rainbow was nearby and always felt safe.

'Maybe I'll even meet a nice boy.' Caidan teased himself, fantasying about an encounter with a pretty twink on the dance floor as he showered and got changed into a blue denim shirt and skinny jeans, and put on some eyeliner.

At the club he had a beer to loosen up before going on the dance floor, and was having a fun evening swaying to the loud music and occasionally dancing with groups of strangers, until he found himself approached by a freckled brunette boy whose directness surprised, but excited, him. Not only did he resemble the kind of boy which he had been fantasying about in the shower, but he was also one of the prettiest femme boys that Caidan had ever seen.

After an hour of dancing and drinking with the boy, whose name he learnt was Casey, and sharing a kiss with him, Caidan found himself leaving the club, holding the boy's hand. Casey had quickly said goodbye to the group of friends she was with, all four of whom were girls, but this didn't surprise Caidan as most of his friends were female too.

"My dorms are nearby, I'm a student at Violet's." Casey explained as she led him down the street. Caidan knew Violet Liberal Arts College was nearby but was surprised as he had thought that it was an all-girls place, but guessed it must be co-ed after all... He was too shocked at the fact that he had unexpectedly scored, when he only planned to go out for a dance, and was being enthusiastically dragged back to the room of a freckled nymph boy of his dreams.

****

"Hang on, I need to put the sign on the door handle..." Casey said when they were back in her dorm room. She rummaged around until she found the 'Do Not Disturb' sign that her and Mitena got, partly as a joke, to put on the door if one of them had scored.

Caidan looked around the room with two single beds, thinking how it looked like a couple of girls lived there, not that he was expecting some kind of man cave from the pretty femme boy.

"Where will your roommate sleep if they come back?"

"Oh, she'll see the sign and just bunk down next door probably."

"She? Very progressive..." Caidan murmured, not having heard of a college where male and females shared the same bedroom, even in unisex dorms, but Casey didn't hear. She pulled Caidan towards her bed, pulling off her shoes with Caidan doing the same before they fell down onto the sheets together, laughing before resuming where they left off in Club Rainbow with playful but deep kissing.

Casey rolled so she was on top of the noirette girl, breaking the kiss to brush her lips over Caidan's cheek then down to her pale neck, making her moan from the soft kisses and gentle nibbles on the sensitive area.

She moved further down the girl's body, unbuttoning her skinny black jeans with eagerness as she hadn't tasted pussy since Nora's. Caidan helped Casey pull the tight jeans down, and Casey triumphantly flung them across the room, the pants landing on Mitena's bed, then slowly kissed herself up the girl's slender pale legs, teasing Caidan but also herself as she was impatient to taste what was between the legs.

Caidan was wearing dark grey boy shorts, which Casey thought was kind of hot, having several pairs herself when she didn't fancy wearing more feminine panties, but she was surprised to see what looked like a bulge in the crotch of the shorts. 'Does she have a...!' Casey thought as she tugged down the girl's underwear to find a cock and balls, a darker shade than the pale skin of the rest of her body and smooth without pubic hair. The penis was hard with arousal, standing about five inches with a pinkish head.

'Wow, not the pussy I was expecting... she must be transgender...' Casey thought, gazing at the cock, never having seen one up close in person. She had never been with a transgender girl before, and had no objection as she didn't base her attraction on a person's genitalia, but was nevertheless a little surprised so kissed the girl's thighs, not wanting her hesitation to make Caidan uncomfortable, before returning her attention to the girl's cock.

'I know some trans girls are uncomfortable having a penis, seeing it as a reminder of their gender dysphoria, and rather not involve it in sex, but she did help me pull down her jeans so guess she's comfortable with it... it does look quite feminine and pretty' Casey though and kissed the shaft of the cock, as Caidan reached down and ran her hand through the brunette's short curly brown hair. Casey kissed up and down the shaft, before focusing on the pink head, licking her tongue over it, not really sure what would feel good but treating it like a big clit.

"You're such a tease babe..." Caidan moaned, propping herself up on her elbows and gazing down at the brunette girl playing with her cock. Casey licked her tongue up the underside of the shaft, over the frenulum, which she noticed especially made the girl moan, and ending at the urethral opening, before parting her lips and taking the cock in her mouth. She sucked on the head of the cock, finding she enjoyed its slight flavour, whilst stroking the shaft with her fingers. 'I would never of I'd be ending tonight by sucking cock... but that's me being too cis-normative. Girls can have pussy or cocks after all...'

Casey found she enjoyed the motion of bobbing her head back and forth on the cock, beginning to take some of the shaft, as well as the head, into her mouth. 'Sucking cock seems to be easier than licking pussy but probably because I'm just a bit clueless about technique, but Caidan sounds like she's enjoying it regardless.'

Whilst continuing to stroke the shaft, Casey removed the cock from her mouth and sloppily kissed her way down it, making it slick with her salvia before her mouth reached the girl's clean-shaven testicles. 'Be a shame not to try them whilst I'm here...' Casey grinned to herself, and licked her tongue over Caidan's balls, sucking each into her mouth in turn, as her hand jerked off the girl's cock.

Caidan's moans of pleasure increased, and Casey returned to sucking on the cock, taking it deeper in her mouth than before, as she fondled the girl's balls with her fingers whilst her other hand squeezed the noirette's small butt which had lifted slightly off the bed.

"I'm going to cum!" Caidan moaned as Casey sucked. 'Maybe I should take the opportunity to see what a facial feels like' The brunette thought, the new experiences making her feel adventurous, so she pulled away, a strand of salvia connecting her lower lip and the head of the cock until it broke. She positioned herself under the cock, mouth open with her tongue stuck out, as she enthusiastically stroked the penis, her hand gliding up and down the slick shaft. Caidan groaned, and Casey felt the cock pulsate in her fingers as it shot out a strand of white cum which landed in a trail across her freckled cheek, over her nose, and between her thick eyebrows.

Casey felt the cock pulsate again, her hand still stroking it, and a second load shot out, splattering her chin, followed by a third, and final, ejaculation which landed directly on her outstretched tongue.

Caidan collapsed back onto the bed, panting, with her hand tenderly playing with the girl's curly brown hair. Casey could feel the warm sticky cum on her face, some running off her chin and down her neck. She closed her mouth, tasting the cum that landed on her tongue as she swirled it around her mouth, thinking that it was slightly salty but otherwise a very mild flavour before swallowing.

Caidan pulled himself back up onto his elbows, looking down at the boy who had gave him one of the best orgasms he'd had in a while, and was just in time to see him swallow a mouthful of cum. The thought of his cum going down the femme boy's throat was almost enough to make him hard again. Casey smiled up at him and he grinned back, thinking how the boy looked even prettier with cum slicking his freckled cheeks and nose, as well as white droplets in his thick brown eyebrows.

"That was amazing!"

Casey blushed and laughed "It was the first time I ever sucked cock so I'm glad I pleased."

This surprised Caidan as the boy had been pretty forward with him in Club Rainbow plus seemed to have a system for one-night stands with his roommate so couldn't believe he had never sucked a cock before. 'Unless...'

"Oh, are you bisexual?" Caidan asked, wondering if the pretty boy normally went with girls, and he had just been an experiment, or perhaps a fantasy come true.

"Nope, I'm 100% gay." Casey replied, looking a bit puzzled, and Caidan guessed the brunette must just be sexually inexperienced after all, but wasn't going to waste time pondering this whilst he was in bed with the beautiful boy.

"Let me help you clean up!" Caidan said and pulled the boy up so, giggling, he crawled back on top of the noirette until they were face to face. They kissed again, Caidan feeling the wetness of the Casey's lips from his sloppy cock sucking, and tasting a twinge of his cum in the boy's mouth. He kissed the boy's chin, sucking off his own cum then kissed the brunette's neck, licking up more droplets that were running down it, and causing Casey to giggle, his laugh prettily feminine.

Casey wiped his cheek and licked his fingers, tasting more of the noirette boy's cum. "Cleaning up is just as much fun as getting messy!" He laughed as Caidan wiped some cum off the tip of his nose.

When Casey was 'cleaned' of cum, Caidan, having tasted his own ejaculation, was keen to savour the pretty boy's cock and receive his own facial so playfully pushed the brunette off of him and climbed on top of the boy, kissing him again then grinning "Now it's my turn!". He unbuttoned the front of the boy's black jeans and pulled them down along with his underwear, expecting to find an erect cock awaiting his lips...