The Cheerleader - Cover

The Cheerleader

by Michele Nylons

Copyright© 2025 by Michele Nylons

Erotica Sex Story: A crossdressed college cheerleader realizes that her femininity, good looks and sensuality are commodities that she can trade to improve her grades. With the help of her sister, she transforms from pretty boy to pretty girl and soon discovers that boys like her more than they should and she is more than willing to put out to get ahead.

Caution: This Erotica Sex Story contains strong sexual content, including Teenagers   Coercion   Consensual   Reluctant   CrossDressing   Shemale   Fiction   High Fantasy   School   Anal Sex   Analingus   Cream Pie   First   Oral Sex   Petting   Voyeurism   Leg Fetish   Teacher/Student   .

Joidale College, Massachusetts – 1985

Candi lay on her side facing the wall. When she heard the door open she scooched over so that her ass hung over the side of the bed. She was wearing her cheerleader uniform: a red body-hugging lycra top, blue pleated micro miniskirt, sheer-to-the-waist flesh-toned pantyhose, red nylon bikini panties and black high heels. The heels were disparate to the uniform because she usually wore sneakers with the cheerleader costume of course but they looked sexy as hell. Her makeup was heavy: black eyeliner and mascara, ruby-red lipstick, colourful eyeshadow and rouged cheeks. She looked both pretty and sexy and she knew it.

Then the door closed and she heard Robert Carlyle’s footsteps approaching the bed and she smiled. She knew that Robert was infatuated with her but he was also a little ashamed and embarrassed by the infatuation, so Candi kept facing the wall and wiggled her ass invitingly.

Robert Carlyle approached the bed feeling highly aroused but also a little reticent. He knew what he was doing was wrong but he had become infatuated with Candi and despite vowing that he was over these tacky, illicit and downright shameful assignations he just couldn’t control his sex drive and his longing for her. The room was gloomy, lit only by the lamp on the desk but bright enough for him to see Candi’s lithe form lying on the bed in that provocative red and blue cheerleader uniform. He could smell her perfume, something sweet with undertones of musk, and he could see the contours of her shapely pale buttocks through her almost transparent panties and his eyes narrowed on the cleft between them. He sighed resignedly and pulled the back of her panties down just a little so he could roll her pantyhose down just enough to expose her creamy cheeks. He was careful to leave her genitals covered.

Candi heard the almost ominous grinding sound of Robert’s zipper unfastening and then the rustle as he lowered his jeans. She heard his fingers skittering on the desktop as he snatched up the tube of lubricant, then she felt the cool, slippery emollient being smeared along her perineum as Robert prepared her for his mighty prong. She smiled when she felt his glans nestle in her sphincter and then closed her eyes and took a deep breath.

Robert felt a little guilty as he guided his swollen member to Candi’s puckered bud. He was a good-looking guy and he could easily chat up one of the girls over at the coed college on the other side of town and coax her into his bed, he’d done so on many occasions but something about Candi drew him to her. It wasn’t just that she was easily accessible because she lived in the same dormitory, or that she was pretty and sexy; there were plenty of pretty girls in town, she simply fascinated and beguiled him.

He pressed his pelvis forward and heard Candi hiss as his bulbous glans opened her tight sphincter.

“It’s ok Bobby, you can go all the way,” Candi whispered.

She knew that Robert didn’t like to be called Bobby but she also knew that he couldn’t resist her.

She wriggled her buttocks invitingly and Robert slowly pushed his thick cock into Candi’s tight, slick hole. He put one hand on her thigh to hold her still while he drilled her with his hard cock, stopping only when he was fully inside her anus and his scrotum slapped against her soft buttock.

“That’s nice Bobby,” Candi crooned, although his cock was stretching her anal cavity quite painfully.

Robert said nothing. He stroked her thigh below the roll of her bunched pantyhose. He liked the feel her silky nylons on his fingertips. He liked the feel of her tight sphincter clutching the base of his penis. He liked the feel of her tight spongy channel gripping his shaft. Without the lubricant it would have been painful but his cock felt like it was enveloped in a slick, satiny glove and he began to thrust, breathing in Candi’s perfume, seeing the silhouette of her lithe body lying sideways on the bed, her ass pushed out, her skirt hiked up, her panties and hose gathered at the top of her thighs. He liked the feel of her pantyhose against his fingers as he gripped her upper thigh. He liked the smell of her perfume. He liked the shape of her body and the curve of her buttocks. But most of all he liked hearing her grunt every time he pushed his cock all the way inside her. He hoped that her muffled cried were the result of pain but deep down he knew that Candi quite liked having his cock buried in her ass.

And Candi did quite liked having Robert’s cock buried in her ass. It was always uncomfortable and sometimes quite painful but it was heartening somehow, knowing that she had this hold on him and that he couldn’t resist her charms. She seldom climaxed when Robert fucked her but he was a good prologue for to what was to follow. She liked how his cock filled her void and how his balls slapped against her ass as he began to fuck her harder. She gritted her teeth and felt Robert begin to fuck her earnestly.

Robert always vowed that he was going to take his time fucking Candi. That he was going to make her squeal or cry or plead for him to stop but he couldn’t resist her feminine charms and the feel of her body. He spun her around so that she was lying on her back and lifted her legs up against his body and stared into her pretty face and began to fuck her viciously.

She smiled up at him, wincing when his cock went into her all the way as he pounded his engorged manhood in and out of her anus. He fucked her so hard that the top of her head banged against the wall. Robert could feel her tight cleft clutching at his cock as he jackhammered it in and out of her ass harder and faster until finally he couldn’t hold back any longer and his knees nearly gave way as he filled her with his scalding issue. He clutched at her thighs and forced every millimetre of his quivering cock inside her tight hole as freshets of warm viscous milt spurted from the eye of his cock, filling her cranny so full that some of his spunk dribbled between her legs.

He didn’t look at her genitals. He knew what she was and he didn’t like to see the physical traits that so disturbed him. He knew that she was erect because the front of her undergarments were tented with the bulge of her hard cock, the sleek fabric of her pantyhose and panties damp with precum.

His orgasm washed over him like a tidal wave as he pulled Candi almost off the bed, bending her back, driving his cock in her as far as it would go and was rewarded when she winced painfully and squealed. But only for second, and then that self-satisfied smirk returned to her pretty face.

Robert shuddered as he voided the last of his issue inside her. After the delightful wavelets of pleasure dissipated, the self-loathing returned and he whipped his cock unceremoniously from her ass and watched his spunk dribble from her distended sphincter and run down her ass crack. As a pitiable act of defiance he snatched at her bedsheet and wiped his cock on it before he put it away and zipped up his pants.

“Leave the essay on the desk,” Candi said matter-of-factly as she dabbed at her ass with tissues and then hiked up her pantyhose and smoothed them out before pulling her panties back into place.

Robert took the essay he had written about T.S. Elliot’s poem The Wasteland from his backpack and dropped it on the desk. It was by no means a masterpiece of literary review but it would fetch Candi a C+, possibly even a B when she submitted the essay under own name.

Robert left the room. He hadn’t spoken a word during the encounter and was feeling regretful that he had once again succumbed to Candi’s charms but he was already thinking about what he was going to do her the next time he went to her room. He nodded tersely at Peter Longmire when he passed him in the hallway.

Peter Longmire entered Candi’s room without knocking and locked the door behind him. He walked over to the desk and put his backpack down beside it then he turned up the illumination of the desk lamp, he wanted to see Candi in all her glory.

Candi was standing in the middle of the room waiting for him. She looked stunning. The tight fitting bodice of her lycra top clung to her lithe frame. When she performed cheers she wore a sports bra, the cups filled with latex prosthesis known as breastforms, but this evening she was flat chested, her tiny nipples distending the lycra. The little blue pleated skirt rested high on her thighs, her translucent red nylons panties just visible below the hem. Her long shapely legs were clad in shimmering fleshtone pantyhose and her feet were shod in ridiculously high heels.

She would never perform in heels of course or the almost transparent nylon bikini panties she was wearing. When she cheered she wore an identical costume but with anklets, gym shoes and form-fitting lycra boy-leg panties known as spankies. Her cock would be tucked in such a manner that when her skirt flew up it would reveal a perfect Vee between her legs, just like a girl. There was no Vee there now. Peter could see the bulge in her panties and the little wet patch undoubtedly caused by the ministrations of Robert Carlyle’s cock.

Her pretty face was framed by a blonde bob. It was her own hair, styled androgynously. She wore it long in both her male and femme personas although she usually put it in a side ponytail or a braid when she cheered. Her makeup was heavy; not what a girl was likely to wear out in the evening but appropriate for a cheerleader.

Peter thought she looked downright sexy. He saw no ‘boy’ in her at all. Unlike Robert Carlyle, Peter had no qualms dealing with Candi for what she was. To him she was a pretty cheerleader who just happened to have male genitalia.

Candi sidled up to Peter and he kissed her softly at first, letting his passion build as the little doll he was embracing rubbed against him and opened her mouth to accept his tongue. Her breath was sweet and her perfume intriguing and Peter’s cock was fully erect inside his jeans.

She reached for him and found him hard and she squeezed his cock through the denim and scratched her long nails down the fly and he gasped into her mouth when she unzipped it and extracted his throbbing manhood. She stroked his cock to full tumescence and smiled when she felt the little globules of precum begin to leak from the eye. When he was fully erect she slipped out of his embrace and helped undressed him. She unbuttoned his shirt while he kicked off his sneakers then she knelt down and pulled down his jeans and underpants, his cock level with her eyes as it sprang free.

She got to her feet and Peter clutched at her, kissing her deeply, pressing his cock into the valley between her legs, rubbing his swollen organ on her silky panties and glossy pantyhose, delighting in the feel of the satiny fabric on his tender organ.

Unbidden, Candi dropped to her knees and took Peter’s penis in her mouth and began to suckle it. He gasped and placed his hands lightly on her head and held her still while he fucked her mouth. She worked her lipsticked lips along the shaft and tickled his frenulum with her tongue, lashing at the bulbous glans, swallowing the sweet nectar of his pre-ejaculate.

Peter looked down into Candi’s beautiful green eyes. Enhanced by the black eyeliner and mascara and colourful eyeshadow they looked catlike and exotic as she stared back up at him, her red lipsticked lips clamped to his veiny shaft as she sucked his cock. She smiled up at him with her mouth filled with cock. It was both cute and depraved and he returned her smile.

“You do that so well,” Peter whispered and Candi removed his cock from her mouth and licked his glans like it was a lollipop.

Then she gobbled his cock again and returned to her cocksucking duties, working her lips along the shaft as her tongue flittered against his frenulum. Peter sighed and felt his scrotum begin to roil as the pleasure became almost overwhelming. Candi sensed it and spat out Peter’s cock. As much as she savoured the taste of his semen in her mouth she wanted to feel his cock inside her. She wanted Peter to finish the job Bobby had only partly completed.

Peter helped Candi to her feet and she pressed her body against him and kissed him passionately, driving the tongue that had just been lapping his manhood deep into his mouth, her lips crushed against his, her fingers lightly stroking his engorged member. She put her arms around him and ground her body against him and then she broke the kiss and looked longingly into his eyes.

“Fuck me,” she mewed like a slattern and turned her back on him and bent over the desk, her ass raised, her buttocks shrouded by the little pleated skirt.

Peter lifted the hem of her skirt out of the way exposing her pert globes encased in the red nylon bikini panties. He massaged her perky cheeks, feeling the nylon panties slip and slide over the lustrous pantyhose. He slipped his fingers inside the leghole of her panties and stroked her glossy, pantyhose-shrouded ass cheeks, nestling his cock in the valley between them.

Candi let out a little squeal of delight as Peter hooked a fingernail in the fabric of her pantyhose, right next to the seam that ran along her ass-crack, flush with the entrance to her spunk-clotted sphincter. He tore a tiny hole, just big enough to slip his cock through. Peter wanted to feel her pantyhose-clad ass pressing into him when he fucked her.

There was no need for lubricant. Candi’s hole was chockful of Robert Carlyle’s semen and it provided the perfect unguent, allowing Peter to slide his engorged phallus all the way inside Candi’s tight rectum. Peter didn’t mind that he was taking ‘sloppy-seconds’, in fact it excited him knowing that he was putting his cock inside Candi’s recently used hole.

Candi did not wince, grimace or grunt when Peter’s cock opened her sphincter and slipped inside her. In fact she smiled blissfully and let out a sight of contentment. Where Robert’s cock was always a little uncomfortable and difficult at times to accommodate, Peter’s penis seemed to be the perfect length and girth and Candi pushed back and wriggled her ass appreciatively, encouraging Peter to fuck her. She knew that he relished the feel of her nylon-sheathed buttocks pressing against his flesh and she was more that willing to pander to his fetish.

Her sphincter lit up with sparklets of pleasure as Peter’s bulbous glans and thick meaty shaft opened it and a deep, satisfying resonance pulsated along the walls of her anus as the head of Peter’s cock stimulated her prostate. She felt her cock become fully engorged, pressing against her pantyhose and her panties and a small puddle of glistening pre-ejaculate formed on the outside of her panties where her cock tented the fabric.

Peter felt Candi’s anus begin to undulate and she shuddered as her breathing quickened and became ragged and then she began to mewl as Peter began to fuck her earnestly. He gripped her hips and fucked Candi harder and faster, coaxed on by her little cries of encouragement as she opened her legs a little wider and pushed her ass back into his groin. This was all wonderful but he wanted to see the expressive look of desire on her face, he wanted to kiss those plump red lips, he wanted to feel her silken-shrouded legs locked around him and he wanted to feel his naked body pressed against her lycra-clad frame.

He clasped his hands together under Candi’s tiny waist and lifted her bodily, with his cock still inside her, and carried her to the bed. He whipped his cock out of her ass and laid her down on the bed.

She looked like the hussy that she was with her pretty face framed by her tousled blonde locks, her makeup smeared, her body dressed in the cheerleader uniform with the ridiculously short skirt and her equally ridiculous high heels, her long legs clad in those shimmery pantyhose, her translucent red nylon bikini panties wet in the groin where her hard cock pressed against the fabric.

Candi opened her arms and smiled up him, her incredibly white teeth framed by those luscious red lips, the lipstick smeared around her mouth like a young whore. Her perfume invaded his nostrils, her flat chest was heaving with desire and anticipation while Peter stood there naked surveying her, his cock jutting out like a prow, a glistening runnel of precum dangling from the tip of his engorged manhood.

Peter fell on her and Candi giggled like a girl as Peter squirmed on top of her, pressing her body into the bed, trying desperately to guide his cock back inside the little hole he had ripped in the gusset of her pantyhose. He eased aside the crotch of her panties and snaked his cock through the tight snag in her hose and once again nestled his glans in her sphincter and Candi dutifully wrapped her legs around his torso and her arms around his shoulders and stared up at him with her incredible icy-green eyes and uttered two words.

“Fuck me,” her breath sweet and her voice tortured with desire.

Peter obliged and pushed his turgid phallus deep inside Candi’s tight, slick asshole. He kissed her and she kissed him back, driving her tongue into his mouth. She writhed underneath him, her legs scissoring on his flanks so that her silky nylons lit up the sensitive dendrites in his delicate flesh. She raked her high heels down his flesh, encouraging him to fuck her harder and Peter obliged.

The feel of her plush tunnel gripping his shaft as he rammed it in and out of her anus and her tight sphincter gripping the base of his cock felt like the hands of a milkmaid trying to express his essence. The silkiness of her nylons grazing his tender skin, the fluttering of her tongue in his mouth, the feel of Candi’s tiny lycra-swathed body under him, the tickle of her hair against his cheek, the redolence of her perfume, all combined to overload his senses and he felt his scrotal sac contract against Candi’s panty-clad ass as a wave of intense pleasure blossomed deep inside him.

“Oh my god!” Peter gasped between crushed lips as his cock quivered and freshets of ejaculate erupted from the eye, deep inside Candi’s anus.

“Yes!” Candi gasped as she clung to him, feeling his cock expand until her rectum was stretched to full capacity.

She felt Peter’s cock judder and undulate as he implanted his seed inside her. His mouth was locked on hers, his tongue fluttering, his hard belly pressing on he belly, his groin rubbing her pantyhose and panties against her hard cock. The feel of his prong slamming in and out of her tight crevasse lighting up her sphincter and prostate, the perception of his hard muscled body driving her into the mattress as he fucked her invoked a monumental explosion of pleasure and desire and her cock shuddered and she flooded her panties with glutinous, hot spunk.

They lay in each other’s arms, letting the remnants of their orgasms recede like a slowly ebbing tide, kissing and caressing each other softly.

Peter’s cock eventually became limp and it slid out of Candi’s anus releasing a small flood of creamy milt which ran down between her legs and soaked into her pantyhose and panties. Peter carefully lifted himself off Candi’s prone body and sat on the edge of the bed, wiping Candi’s lipstick from his face and her semen off his belly and then dabbed at his genitals with the fluffy white towel that Candi had strategically placed at the foot of the bed.

“What did you bring me lover?” Candi chewed a fingernail as she smiled up at him mischievously.

“Danny and I broke into the staff file room and lifted a copy of next week’s Modern English exam,” Peter replied as he began to dress.

“Put it on the desk next to Robert’s essay before you leave,” Candi said matter-of-factly as she used the towel to sop up the semen drenching the front of panties.

“You are quite the little mercenary bitch you know. What you are doing is almost prostitution,” Peter said as he tied his shoelaces.

“Are you calling me a whore?” Candi chuckled.

“Well, kinda,” Peter snickered.

“I gave you a freebee last week,” Candi countered.

“And I appreciated it. Have you thought any more about coming away with me during the autumn break?” Peter became serious.

“That’s a discussion for another day honey. I need to clean up and do a little homework before I go to bed,” Candi led Peter to the door.

“You mean transcribe Robert’s essay into your own words so you can submit it tomorrow,” Peter chuckled.

“Hey, a girl’s gotta do what girl’s gotta do to maintain her average above C,” Candi leaned in and pecked Peter on the cheek and unlocked the door.

Peter slid out of her room and Candi locked the door behind him.

She sat down at her desk and opened a pack of makeup wipes and removed the cosmetics from her face and then she shucked out of her cheerleader costume, tossing the ruined pantyhose in the trash along with the makeup wipes and put the semen-soaked panties in the washing basket. She could get another evening or two out of the skirt and top before she laundered them so they got hung up in the wardrobe next to the rest of Candi’s cheerleader clothing. The heels, perfume, costume jewellery were packed away.

She was no longer Candi Kennedy. Candi was now her male alter ego Kyle Kennedy. Kyle slid into his shower shoes, put on a terry bathrobe, collected the trash bag and his toiletry bag and left his room and made his way to the communal toilet and shower, pausing to drop the disposable bag containing the pantyhose and makeup wipes down the trash chute. He used the ablutions and took a long shower and returned to his dorm room, saying hello to the few fellow students loitering in the corridor at this late hour.

Kyle put on pyjamas and sat at his desk and began to meticulously transcribe the essay that Robert Carlyle had written analysing T.S. Elliot’s poem The Wasteland, which had to be submitted to Professor Ingham by the end of the week. Robert had surmised that the poem was about culture, specifically the celebration of culture, the death of culture, and the misery of being learned in a world that has largely forgotten its roots. Kyle had read the poem once and didn’t like it so he had Candi trade sex for the essay. It was easier to endure having Robert Carlyle’s big truncheon-like appendage banging away at Candi’s ass than to spend hours researching and writing the essay.

Kyle was breezing through college maintaining a B GPA using plagiarism and cheating on his exams. He skipped most of his classes so he could enjoy the parts of college life he enjoyed which was theatre, drama, athletics and of course cheerleading. His feminine alter ego Candi was the reason he was able to live this life of subterfuge. In fact Kyle wished that somehow he could live fulltime as Candi and he often fantasised about how this might be achieved. As he worked late into the night transposing Robert Carlyle’s very well-researched essay, he began to see the nexus of the poem and the life he was living and his thoughts turned to how it all started.

The Kennedy Residence – Five Years Earlier

Kyle always knew that he was different to the other boys but it wasn’t until he entered puberty that he realised why. He was a slim, athletic boy with an almost angelic face framed by sun-bleached blonde locks which he always worn fashionably long. Kyle had no interest in manly pursuits. While the other boys climbed trees, played shoot-em’-up, fished, camped and tried out for the football team, Kyle preferred the arts. His train set, Erector Set, and Hot Wheels collection remained almost untouched. He preferred to play with his sister’s Barbie dolls and read her teen fashion and heartthrob magazines. This was not lost on his mother, Bab’s Kennedy, or his sister Sharon.

The saving grace that prevented Kyle from becoming a pariah and the subject of bullying was his athleticism. Too skinny to play football, even as a receiver, and nowhere near tall enough for basketball, Kyle excelled at gymnastics so while not considered a ‘jock’, he was accepted as an athlete. His sister Sharon was head cheerleader for the Brentfield High Warriors football team and she too had athletic ability. Kyle liked to hang out with Sharon and her friends, listening to them talk about fashion, music and boys they were sweet on. Most of his peers thought that Kyle hung around with his sister and her friends as a means of befriending the girls in order to ingratiate himself so that he might get himself ‘some poontang’ which most of the boys his age only dreamed of and he did nothing to dissuade their assumptions.

The reality was that Sharon and her girlfriends, mostly other cheerleaders, somehow intrinsically knew that Kyle had no romantic interest in them at all and he was tolerated accordingly because he shared their interests and they valued his fashion sense. He also helped the girls with their dance routines and cheers and became their surrogate coach. One day when the girls were practicing a particularly difficult cheer which required lifting April Montague onto Wendy Davidson’s shoulders, April blurted out... “I would feel safer if Kyle was the one who was lifting me.” The girls suddenly ceased their boisterous banter and looked seriously at Kyle and then at Sharon.

“We wouldn’t be the first cheer squad to have a boy as part of the troop. Did you know that originally cheerleaders were all male? What do you think Kyle?” Sharon asked her brother.

Kyle thought about it only for a minute and then gave an enthusiastic nod of his head.

“Sharon, you know that boy is different right?” Babs said when Sharon told her mother that her brother had joined the cheer squad.

“I know mom, that’s why the girls have no problem with him hanging around us. I think he’d be more likely to wear their panties than try to get into them,” Sharon giggled.

Babs Kenndy did not giggle at her daughter’s joke. Her face was suddenly filled with storm clouds and she gripped Sharon’s wrist.

“Has your brother been wearing your clothes?” she asked seriously.

Sharon considered her answer carefully before she replied.

“I did notice that some of my clothing seemed to disappear mysteriously and suddenly reappear and it wasn’t quiet how I left it. You know it wasn’t folded the way I like or it wasn’t exactly where I left it in the wardrobe. I like to keep my clothes in order. But that hasn’t happened for a while now,” Sharon replied softly.

“Sharon, I noticed that same thing and I’ll confess to you in the strictest confidence that on two occasions I found Kyle dressed in your clothes,” Babs said conspiratorially.

“I’m certain it’s nothing sexual. When I confronted him about it the first time he told me that he just felt comfortable wearing girls clothes. Of course he was in tears and promised never to do it again but of course he did it again because he couldn’t stop. I’m going to tell you something that must remain a secret. I bought Kyle a few things: a peignoir, a full-slip, a set of babydoll pyjamas, some nylons and some panties and I told him he could wear them only in the confines of his room and that he was never to touch your clothes again,” Babs whispered, shocking her only daughter.

“You know as well as I do that Kyle is more comfortable in the pursuit of feminine pursuits than male. He’s special that way and he will have to deal with the consequences as he grows up. I hope it’s just a phase that will pass but I doubt it. You know about Uncle Steve?” Babs looked her daughter in the eyes.

“Sure mom. Uncle Steve is gay and he had to move to California because of the family’s disapproval. Do you think Kyle is gay?” Sharon asked, considering the question not for the first time.

“I’ll just say this. I’m not going to stop Kyle becoming a cheerleader but you look out for him and you keep everything I’ve told you a secret,” Babs reached for her Kools, closing the conversation and dismissing her daughter.

Kyle was a hit. With his core body strength, dexterity and artistic ability he was able to introduce daring and complicated cheer routines into the cheerleader’s repertoire. Babs had a body-hugging jump suit made for him in the same colours as the girls cheerleader costumes. When Sharon left high school and went to college Kyle took on the role of head cheerleader and that final year the Brentfield High Warriors cheer squad went on to become state championships.

Kyle applied to several colleges but was rejected by most because, although he was accomplished in arts and literature, his core academic scores weren’t competitive. Luckily for him, despite being a single mother, Babs was able to put away a decent college fund and Kyle found a place at Joidale College, one of the few male-only colleges remaining. She was only able to achieve this because Kyle intended to undertake a fine arts degree and Joidale College was a liberal arts college and would supplement his college fund with a scholarship.

Kyle settled into college life and enjoyed theatre, drama, athletics and of course he became a cheerleader for the school’s football team. Sharon was head cheerleader at her college and they remained competitive even though they attended schools in different states.

Spring Break - 1985

Kyle and Sharon were both home from college for spring break. They discussed cheer routines, costumes and in Sharon’s case, boyfriends. By now, Kyle, with his eighteenth birthday behind him, was well aware that he was gay but had not come out and was reticent about doing so. He was attracted to boys but in a particular way. He imagined himself in a feminine role, dressed in a pretty dress or skirt and blouse, nylons and heels. He imagined kissing the boy with his lipsticked lips, his eyes enhanced by makeup, bathed in a miasma of perfume. The boy would slide his hand under Kyle’s skirt and do things that made him feel nice. Kyle didn’t know exactly what the boy did with his hands under there but it was at this point during his fantasy that he would ejaculate into the nylon stocking wrapped around his cock that he was using as a ‘cum-rag’. He loved the feel of silk, satin and nylon on his body, especially his cock.

 
There is more of this story...
The source of this story is Storiesonline

To read the complete story you need to be logged in:
Log In or
Register for a Free account (Why register?)

Get No-Registration Temporary Access*

* Allows you 3 stories to read in 24 hours.

 

WARNING! ADULT CONTENT...

Storiesonline is for adult entertainment only. By accessing this site you declare that you are of legal age and that you agree with our Terms of Service and Privacy Policy.


Log In