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.

In his fantasies Kyle wasn’t Kyle… he was Candi, or more correctly she was Candi. Candi was the feminine alter ego that Kyle had invented for himself and who he became when he secretly dressed in women’s clothing. Kyle crossdressed when he was alone in his room at college and still had the stash of feminine clothing that his mother had given in his bedroom at home.

Sharon was curious about Kyle and probed him gently about how he was settling at Joidale.

“I suppose being an all-male college it’s difficult to meet girls?” Sharon asked expectantly.

“There is a coed college nearby and the guys do pretty well there… or so they tell me,” Kyle sidestepped the question.

“But what about you Kyle?” Sharon continued to probe.

“Don’t patronise me Sharon. I know that you suspect I’m gay. I know that mom suspects I’m gay. You both know that I like to wear women’s clothing,” Kyle said indignantly.

There! It was out!

“Tell me about that. Do you just like to wear the clothes or is it something deeper?” Sharon asked, stroking her brother’s arm affectionately.

“You’re going to laugh. When I dress up I actually become someone else. I become Candi, this alter-ego I’ve created. She’s a sexy sassy gal but she’s smart too,” Kyle blushed deeply.

“But.. Candi… is a closely kept secret right? She has never been with a boy?” Sharon asked softly.

Kyle shook his head.

“Let me see Candi, maybe I can help her,” Sharon whispered.

Kyle was mortified. His own sister wanted to see him present as Candi. Kyle knew that his efforts at crossdressing were very amateurish. But… Sharon was offering her help. She hadn’t mocked him.

Candi walked into Sharon’s bedroom half an hour later, feeling scared but mostly embarrassed. Sharon tried not to laugh. Candi’s efforts at makeup and hair were pitiable but she saw potential. Candi had a nice figure and had inherited the Kennedy family bubble-butt just like his mother and sister and her legs were long and shapely. Sharon was always one to take up a challenge.

Candi was unsteady on her feet in the heels one size too big for her which she had purchased at a thrift store. She was blushing and felt awkward and not the least feminine. Sharon sensed her brother’s reticence and embarrassment and said nothing but led him to the chair in front of her vanity.

“Let me help you with your hair and makeup and then we will work on poise. Tomorrow we are going shopping and because you will be with me there will be no need to be embarrassed. If I can’t turn you into a proper lady by the end of spring break, I will have failed,” Sharon ran her fingers through her brother’s hair and was already thinking about how she was going to style it.

Candi smiled. Sharon hadn’t made fun of her and was willing to help. She felt safe.

One week later Candi walked into Sharon’s bedroom to make her debut. She had dressed herself, styled her own hair and applied her own makeup. Candi looked stunning in a ruched, figure-hugging, blue satin minidress, glossy fleshtone pantyhose, white four-inch high heels and her own shoulder-length, tousled, bleach-blonde hair. Her makeup was eighties heavy: smoky eyes, bold eyeshadow, her high cheekbones defined by blush and her sensuous lips enhanced with plum-red lipstick, which matched the nailpolish on her long nails.

Despite being flat-chested she looked adorable and sexy with her slim waist, voluptuous hips and buttocks, long legs and pretty face. Sharon was a little jealous in fact. She had Candi pose and then move around the room, admiring her stance, her gait and her feminine poise. In Sharon’s opinion Candi could pass as girl in most situations.

“Ok sister. You’ve got it. There’s not much else I can help you with, the rest is up to you,” Sharon circled Candi looking for faults but couldn’t find any.

“Thanks sis but I’m not sure I can do ‘the rest’ as you put it. I’m too scared and nervous to go out into the world like this,” Candi sighed.

“Which is why I am bringing the world to you. As you know, mom has gone to Vegas with her girlfriends for three days and we have the place to ourselves so I’ve invited some friends over,” Sharon smiled at Candi.

“I’m not sure if your girlfriends are ready for this,” Candi indicated her own body.

“Who said anything about girlfriends? I’ve invited Craig Whitnall and Mitch Donnelly over,” Sharon’s beaming smile was juxtaposed by Candi’s look of dread and concern.

Craig was Sharon’s current hometown squeeze but she’d admitted to Candi that it wasn’t anything serious and that they both played the field because they went to different colleges and were too young to commit to a serious relationship. Candi had no idea who Mitch Donnelly might be.

“What the fuck are you talking about?” Candi was incredulous that her sister would do such a thing.

“Mitch came out to Craig as bisexual a while ago and admitted that he has a thing for transvestites. Craig showed him a polaroid that I took of you dressed as Candi and Mitch nearly creamed his jeans. He’s hot for you honey,” Sharon winked at her new sister.

“You told me those pictures were only for us! Something for me to look back on. You shared those with your fucking boyfriend?” Candi was flabbergasted.

Just then the doorbell rang.

“Too late sugar. You told me that you have never been with a boy before but you are keen and curious. Mitch is handsome and has been warned not to push you any further than you are willing to go,” Sharon said jauntily as she skipped away to answer the door.

Candi found herself sitting on the couch next to a tall, goodlooking young man, three years her senior. She was nervous and didn’t know what to do with her hands so she clutched her drink and tried to keep up with the conversation whilst being overly aware that she was for all intents ‘out’ for the first time ever.

Mitch and Craig had arrived with pint of Jack Daniel’s and Sharon had provided Coke and ice and mixed everyone drinks while Candi tried to make herself look invisible and seriously considered running away to her room. But she didn’t. The reason that she hadn’t was because both Craig Whitnall and Mitch Donnelly had both been overly complimentary and attentive to Candi when they arrived. They both had the good sense not to refer to her using any male pronouns or make any comment tantamount to that they knew that it was Kyle hiding under the hair, makeup and clothes. They simply treated her like a girl. A girl named Candi.

Candi had taken a deep breath, accepted the compliments and put all thoughts of Kyle out of her mind and allowed Candi’s spirit to take over completely. She accepted her drink and slinked across the room to the couch without even having to consciously think about comporting herself in a feminine manner. It came naturally to her now that her sister had tutored her to do so. With her back to Mitch Donnelly she was unable to see that he was openly ogling her ass and her legs as she made her way across the loungeroom, her high heels click-clacking on the maple floor.

She froze when Mitch Donnelly sat down beside her, even though he left a respectable distance between them and made not a single advance. Candi tugged nervously at the hem of her dress and wished that she wasn’t wearing such a revealing garment; not that any of the dresses and skirts in her new wardrobe were any longer than what she was wearing. Sharon, Mitch and Craig were talking about college and what they might do after. Craig was sitting in the big easy chair where Babs usually sat and Sharon was nestled in his lap. She wasn’t dressed as flamboyantly as Candi: a black vinyl skirt, red satin low-cut blouse and taupe pantyhose. She’d kicked off her heels before plonking herself in Craig’s lap.

Craig was distractedly stroking Sharon’s leg and would nuzzle her neck when she was speaking. The sexual energy coming from them both was palpable making Candi feel a little uncomfortable and she had to admit, also a little jealous. Mitch had not made a move on Candi even though everyone in the room knew that he had been brought along specifically to do so.

“Candi is studying fine arts at Joidale College. She’s also head cheerleader and active in the student theatre program,” Sharon announced in an attempt to bring Candi into the conversation.

“I bet she looks foxy in her cheerleader outfit,” Mitch commented, keen to pay Candi another compliment.

Craig and Sharon smirked at each other knowingly and Candi wanted to curl up in ball with embarrassment. Mitch was obviously oblivious that Joidale was a male-only campus.

“She certainly looks foxy in that little ruched minidress, don’t you think Mitch?” Sharon helped Mitch cover his inadvertent faux pas.

“You look gorgeous Candi,” Mitch turned to face Candi and patted her knee.

“And on that note, Craig and I are retiring to my bedroom. You kids behave yourself… or don’t. We can get together for drinks again in a couple of hours,” Sharon leapt out of Craig’s lap and extended a hand and Craig took it and followed Sharon upstairs leaving Candi and Mitch alone in the loungeroom.

“Don’t worry I won’t bite. Craig has told me to watch my step with you. I fully understand that you are nervous and maybe even a little scared,” Mitch smiled at her and once again Candi was taken with his good looks.

“God! Is there anything that Sharon hasn’t told you both about me?” Candi was mortified.

“She hasn’t really told me much at all, just that this is your first time out. I have to say Candi that if I didn’t know better I’d swear that you were just another attractive young woman,” Mitch breathed.

“Fuck that didn’t come out right at all. What I meant to say was, I find you enchanting,” Mitch sidled a little closer to her.

Candi was breathless. Alone with a handsome young man for the first time and she didn’t know what to say to him. A fleeting recollection of her fantasy, where a boy would slide his hand under her skirt and do things to her that made her feel something very nice, crossed her mind and she tried to suppress it. It didn’t help that Mitch had scooted even closer and she could smell his cologne and hear him breathing and when she turned to face him she was once again taken with how handsome he was.

When he leaned in and pressed his lips to hers she thought she would faint. She realised that Mitch had decided that there had been enough talking, it was time to shit or get off the pot as Babs was want to say when her kids dithered. Candi had always wondered what it was like to kiss a boy and she closed her eyes and savoured the experience.

Mitch kissed her softly at first and she sat perfectly still and just enjoyed feeling Mitch’s lips pressed against hers. He slipped the tip of tongue into her mouth which caught her off guard but Mitch had slid his arm along the back of the couch and he cupped her shoulder as she instinctively shied away. He kissed her a little harder and slid his tongue all the way inside her mouth and his other hand sought and found her knee. Candi could have easily broken the embrace if she wished to do so but she relaxed and just let Mitch take the lead.

She tentatively sought Mitch’s tongue with the tip of her own and softly pressed her lips to his, returning the kiss and she felt Mitch smile and his hand began to stroke her knee. She mewled a little with the sensuality of it and leaned into the handsome young man, feeling his hard muscled torso under his shirt. Candi had never felt so feminine or so carnally excited. She had tucked her cock along her perineum, her pantyhose gusset holding it in place so that it didn’t spoil the silhouette of her dress and it was becoming engorged and uncomfortable.

With practiced finesse Mitch eased Candi down on the couch and lay beside her, kissing her, stroking her legs, gently petting her buttocks, his body pressed against hers. He wasn’t insistent or crude, rather he was tender and considerate. When he wasn’t kissing her he was whispering compliments in her ear, telling how attractive and alluring she was and how he had been stricken by her beauty when he first laid eyes on her.

Candi accepted his compliments and returned his kisses a little more confidently. Wasn’t this what she had aways dreamed of? Presenting sexy and enfemme and having a man desire her and cosset her? Her fantasy was becoming a reality. The reality of it was all the more real because she slowly became aware that Mitch was pressing his hard cock against her belly. Her own cock stirred painfully in her loins, demanding to be released from its nylon prison.

Candi had always adored the feeling of sheer nylon on her flesh and when Mitch circled the pads of his first and second fingers on her knee, gently caressing her pantyhose, igniting freshets of pleasure Candi had only dreamed of, she purred like a contented cat. When his hand began a slow but determined journey up her thigh and slid under her skirt she became a little skittish but she didn’t bat it away. When his fingertips caressed the crease where her legs joined her torso she shuddered with the wantonness that suddenly erupted and when his fingers drifted almost wraithlike across the front of her panties she thought that she might pass out.

Finding nothing there Mitch’s fingers continued their journey and he smiled around a deep kiss when they circled the spongy protuberance in the crotch of Candi’s panties lying along her perineum. He stroked the phallic bulge, his fingertips tracing the outline of the shaft to the sensitive fraenulum causing Candi to wriggle against him and gasp into his mouth when he circled it with his fingertips and then he fondled the plum-like glans and this time Candi actually yelped. Mitch could feel the slippery puddle of pre-ejaculate that had seeped through her pantyhose and panties.

Mitch traced his fingers along the front of her panties and then slipped his hand inside the waistband of her panties and pantyhose, the elastic cincture clawing his wrists as he searched for her cock, found it and freed it from between her legs. He lay her phallus snug against her pubis and extracted his hand and resumed stroking the appendage through the layers of nylon and satin. Candi purred like a kitten, snuggling against Mitch and kissing him deeply.

Mitch took Candi’s hand and placed it in his lap and she suddenly realised that she had been neglecting him. She was new to this but common sense told her that when someone lovingly masturbates you, you should return the favour. She struggled a little with his zip, the button on the waistband on his trousers and his belt buckle but Mitch was patient. He knew that it was Candi’s first time and he wanted her to experience it fully without him helping her too much. He had the decency to lift his ass off the couch a little so that Candi could pull his pants and his underwear down so that she had full access to his genitals.

Candi tentatively took Mitch’s cock in her hand. He was already semierect. She marvelled at the feel of the velvety flesh covering his shaft, it was smooth and silky with little veins running along the length of it that pulsed with his lifeblood. As she worked her hand up and down the appendage she felt it grow to full tumescence and in addition to sexually stimulating her, she felt a perception of accomplishment. It was she who had caused this older man to become erect and lustful. Mitch began to kiss her with greater intensity and stroked her cock a little harder and faster through her panties as Candi whipped her hand up and down Mitch’s steely organ.

She felt the delectable sensations in her genitals begin to escalate as Mitch gripped her cock firmly, encasing it in the satin and nylon of her panties and pantyhose, the frisson of the satin gliding over the lustrous nylon in which her throbbing, leaking cock was sheathed releasing freshets of pleasure that she knew would soon bring her to climax. Mitch’s mouth was needily clamped on hers, his lips crushing, his tongue demanding, his body pressed against her, his cock throbbing in her hand.

She stroked him harder and faster and returned his needy kisses. They were both panting into each other’s mouths, Mitch’s free hand was scouring her thighs, her free hand cupped Mitch’s scrotum while she frantically whipped the other up and down his tender organ, feeling it pulse and throb, feeling the precum leak from the head in an almost continual stream.

Mitch suddenly tensed and she felt his cock judder and then abruptly erupt. Candi felt Mitch’s scalding jism splash onto her wrist, then spatter on her leg. The dank, sweet and sour stench of fresh semen assailed her nostrils as she felt his issue spray on her arm, her belly and her leg. His cock quivered in her hand and her fingers were sticky with his seed. Mitch yanked on her painfully erect penis trapped in its silken prison and Candi felt a wave of glorious release as she creamed her panties.

They orgasmed together, pawing at each other, milking each other’s cocks, kissing frantically, trying to suck the essence out of each other as they writhed together on the couch in a blissful paroxysm of carnal pleasure.

Sharon had crept downstairs and was watching them through the slightly ajar hallway door, her fingers under her skirt and inside her panties, circling her clitoris, her vagina clotted with Craig’s jism. She smiled to herself and felt an even greater sense of accomplishment. She had helped her ‘sister’ lose her virginity. She padded away back to her bedroom where Craig waited for her. She needed him to fuck her a second time because watching Candi and Mitch had reignited her desire.

Candi and Mitch lay in each others arms in post-orgasmic bliss. Their kisses were less frantic, almost tender and they smiled at each other between the kisses. Mitch stroked Candi’s hair and gazed into her bright green eyes.

“How was it?” he asked.

Remarkable, magnificent, wondrous, amazing, astounding, incredible, stunning, astonishing, were words that crossed Candi’s mind but she didn’t want to sound naïve.

“It was nice,” she whispered.

Mitch just smiled knowingly at her.

“I need to go upstairs and change and put my dress in the wash otherwise it will stain,” Candi said meekly, looking for a way to extract herself from Mitch’s embrace.

The bloom that accompanied her first sexual encounter was fading and she started to feel guilty about it. She was experiencing a little regret and angst.

Mitch did not try to stop her when Candi extricated herself from his embrace. He just tugged at his pants while Candi held the skirts of her ruched satin minidress away from her lap. The dress was already blemished with little wet patches where Mitch’s semen had soaked into the fabric and puddles of his spunk were congealing on the legs of her pantyhose. Her panties were a swamp of curdled jism. She felt a little demeaned as she made her way upstairs holding her dress like that.

She heard the rattle of bedsprings and moans of sexual congress as she passed Sharon’s room and she blushed. In a way it felt a little incestual that she and her sister were having sex at the same time in the same house. Candi’s cock was still semi-hard and her genitals were still aflame with desire but she also felt an overwhelming guilt and she didn’t know why. She hadn’t done anything wrong. She was free, single and over eighteen and had noting to be ashamed about.

Candi stood at the foot of her bed and lifted her dress over her head and let it fall to the floor. She would spot clean the semen stains and wash it on the gentle cycle. She suddenly became aware that Mitch Donnelly was standing in the doorway, leaning against the doorjamb, studying her. He was holding a paper sack. Candi had mistakenly thought that Mitch was hitching up his pants when she left him on the couch but in fact he had been taking them off and was now naked, his cock hard again, jutting out of his groin like a steel pole.

He was openly ogling her as she stood there dressed only in her glossy fleshtone pantyhose, white four-inch high heels, panties and brassiere. She self-consciously put her arms across her flat chest and Mitch smiled at the gesture and feasted his eyes on her slim waist, voluptuous hips and buttocks, long legs and pretty face. Her makeup was smudged and her hair tousled but that only served to make her look sexier.

“We haven’t finished Candi. You’ve still so much more to learn,” Mitch stepped into the room and closed the door, putting the paper sack down on the dresser..

She was frozen in place and unable to stop Mitch from closing in on her and easing her backwards towards the bed. She felt the baseboard of the bed against the backs of her legs and then Mitch lowered her onto the coverlet and lay on top of her.

“Put your arms around me and lift your legs. Wrap them around my body and rub your pantyhose against my skin,” Mitch whispered in her ear and then his lips found hers and all of Candi’s misgivings dissipated.

She met his tongue with hers and put her hands on his shoulders and wrapped her legs around his waist and scissored them against his flesh. His cock pressed against hers through the layers of silky fabric and she became immediately erect. Mitch humped away at her, his kisses becoming frantic and his breathing laboured. She very much enjoyed the feel of Mitch’s penis thrusting back forth along the length of her own stiff organ. She was already wet down there from her previous orgasm and the rivulets of precum dribbling from their cocks made it even wetter.

Candi adored the feeling of Mitch’s body lying on top of her: his muscled arms and shoulders, his flat belly, his strong legs juxtaposed to her tiny frame, slim waist and Rubenesque hips and buttocks. Her long, silken-sheathed legs wrapped around him, her high heels scratching at the small of his back, her long fingernails scouring his shoulders as she encouraged him to hump her harder. She imagined this is what it must feel like to be fucked.

Mitch must have been reading her mind because he slipped a hand between their bodies and guided his cock between Candi’s legs and slipped it inside her panties so that it pressed against her puckered bud, the gossamer fabric of her sheer-to-the-waist pantyhose the only barrier.

Candi froze and Mitch broke the kiss and stared into her eyes, his face a study of concentration. Then he broke into a smile that lit up his handsome face.

“You’re not ready for that yet,” he chuckled and Candi did not appreciate his self assured attitude.

“But you are ready for this,” Mitch broke free of her embrace and his face began a journey from her neck down to her groin, all the way licking, kissing and nipping at her sensitive places.

When he stopped with his head between her legs Candi was a burning ball of wantonness and desire. When he ripped out the crotch of her pantyhose with his teeth she gasped. When he took her swollen appendage into his mouth she moaned.

Mitch used his mouth expertly on Candi’s phallus, sometimes lapping gently at the sensitive frenulum and glans and sometimes taking all of it in his mouth and sucking on it with his lips, making Candi squirm and writhe on the bed begging for release, taking her to the edge and then backing off.

He spat her cock after a few minutes and climbed back on top of her.

“I hope you were paying attention because now it’s your turn to do it to me,” he kissed her passionately and then lifted Candi to her feet and lay on the bed with his crotch positioned on the edge.

“Get on your knees and suck me,” Mitch growled.

Candi didn’t really like this side of Mitch; the dominating, overbearing side, but she was excited to be sucking her first cock and eager to see what it was like. She duly got on her knees between Mitch’s legs and began to fellate him. Mimicking Mitch’s actions she sucked, lapped and tongued Mitch’s penis and was rewarded with a constant dribble of sweet precum which she swallowed willingly.

Mitch was groaning and moaning as Candi used her lips to suckle his shaft while her tongue lapped at his glans. She cupped and gently fondled his scrotum and Mitch expressed his appreciation by tangling his fingers in her hair so he could hold her head and fuck her mouth. Candi found this quite stimulating and sucked gleefully on his cock while she searched out her own swollen, aching member.

Mitch gripped her head and forced his cock all the way inside her mouth and Candi felt it quiver and she knew that it was about to erupt. She slavered at the bloated organ whilst furiously stroking her own penis. When Mitch filled her mouth with his creamy milt she experienced a sympathetic orgasm and sprayed her seed onto the bedspread as she dutifully swallowed Mitch’s musky semen.

When she had sucked every drop of jism from Mitch’s cock she spat it out and lay down beside him on the bed, both of them breathing raggedly, physically exhausted.

“So… how did you find your first time?” Mitch finally broke the silence.

He rolled over and cuddled Candi, gently teasing her tangled hair from her face and kissing her softly.

“I know it’s cliché to say it, but it was awesome,” Candi admitted.

A gentle tapping on the door broke their reverie.

“Get a move on Mitch, we have to go,” it was Craig Whitnall who had obviously finished his tryst with Sharon Kennedy.

“Sharon has invited me over again tomorrow evening. No need to wear a dress, just wear some sexy lingerie and heels. Use this and get ready for your next lesson,” Mitch snatched up the small package he had carried into the bedroom and dropped it in Candi’s lap.

He kissed her almost savagely on the mouth and left without another word.

Candi lay on the bed and considered what had just happened to her. She liked most of the things that Mitch had done to her and that she done to him but was not enamoured by his dictatorial attitude. He was treating her like she was his pupil. But then when she thought about it, she supposed that was exactly what she was. Apparently Sharon had invited Mitch Donnely around to their house again tomorrow to further Candi’s education and the lessons would continue.

A smile crossed Sarah’s face and then she peeked into the paper sack.

The Next Evening

“Are ready honey?” Mitch Donnely’s glans pressed against Candi’s pink puckered bud which was glistening with the slippery emollient known as KY Jelly.

She was wearing a red peignoir, almost transparent nylon stockings clipped to the lace garters of her suspender belt, her feet shod in red ‘fuck-me’ pumps, her sun-bleached locks stylishly tousled, her makeup heavy and dramatic. The thong of the red satin G-string had been eased aside so that Mitch’s cock had unfettered access to her anus. She was on her back with her legs open. The missionary position. But Candi felt anything but missionary with her ankles resting on Mitch’s shoulders, his hands gripping her thighs. A pillow had been placed in the small of her back to lift her ass off the mattress to make things all the more easier.

She felt vulnerable, excited and a little scared.

After Mitch had left yesterday Candi had opened the package and found a tube of KY Jelly and a contraption consisting of a white hard plastic hollow tube attached to a red rubber squeegee bulb. She blushed when she realised what it was and what she supposed to do with it. Before she could think too long and hard about the significance of the douche and the water-based personal lubricant the door to her room burst open and Sharon entered looking both excited and anxious.

Candi snatched at the coverlet and quickly pulled it over her body to hide her cum-spattered lingerie and pantyhose and the contents of the package. Her sister was still wearing the black vinyl skirt. Her red satin blouse was open and her brassiere was missing, her supple breasts swinging freely. Her taupe pantyhose were laddered and her hair was bedraggled and her makeup ruined. She looked exactly what she was: a young woman who had been vigorously fucked several times.

“Soooo… how was it? Tell me all about it, you hussy,” Sharon leapt on the bed and snuggled up to Candi.

Candi blushed but she told Sharon everything that had happened between her and Mitch but she didn’t mention the package and what was in it. There were some things that were a little too personal to share.

Sharon did not tell Candi that she had crept downstairs and had been watching Candi and Mitch canoodle on the couch through the slightly ajar hallway door. It was more exciting listening to her ‘sister’ tell her about her first sexual encounter.

“So you invited Craig and Mitch around again tomorrow evening without even talking to me about it?” Candi said a little sulkily.

“I did nothing of the sort! I’m going out with Denny Harris and you will have the place all to yourself with Mitch. I can call and cancel if you like?” Sharon gave Candi a conspiratorial grin.

Candi just smiled back at her sister and shook her head.

“Ok young lady, you better shower and change. Make sure you wash this dress as soon as possible otherwise it will be ruined. You know that semen stains are nearly impossible to get out once they dry,” Sharon toed Candi’s rucked satin dress and wrinkled her nose.

“And hurry up, I need to shower and change too,” Sharon skipped out of Candi’s room.

That morning Candi had been full of trepidation but also excitement and when Sharon left to meet up with Denny Harris, Candi went into the bathroom and used the douche. The experience was neither pleasant nor unpleasant, it was merely a necessity. She checked for any rogue hairs on her smooth face and body, took a shower and went back to her bedroom and began to put on her makeup. She recalled what Mitch had told her: just wear some sexy lingerie and heels and she had dressed accordingly.

Candi had to admit that although she was enjoying being educated by Mitch, she found him rather domineering and autocratic and she wondered if that was how most men treated women. Once she had dressed and applied the finishing touches: polishing her nails, spraying perfume, checking her hair one last time, she went downstairs and made herself a drink and watched the clock.

When she greeted Mitch at the door she could tell that he appreciated the efforts she had gone to present herself alluring. His hands were all over her and he kissed her passionately whilst directing her up the stairs and to the bedroom. He tore off his clothes and led Candi to the bed where there was some rudimentary foreplay and a little fellatio but it obvious what Mitch really wanted.

He jammed the pillow under the small of Candi’s back, eased aside the thong and lubricated her sphincter then climbed on top of her.

Candi nodded yes to the question ‘are you ready’ and Mitch’s handsome face broke into a beatific grin.

“I’m going to deflower you now honey. It might hurt a little a first but don’t worry it’s going to be wonderful,” Mitch gazed down into Candi’s emerald green eyes then he pressed his lips against hers and kissed her as he began to push.

Candi suppressed a groan as Mitch’s cock dilated her sphincter and slipped inside her anus. The pain wasn’t sharp, rather a dull ache which stopped when Mitch’s glans penetrated her tight ring and he stopped pushing. He allowed Candi to get used to accommodating his engorged rod and when he thought she was ready he began to push again, stopping when she winced and then proceeding when she smiled up at him that she was ok. He watched her eyes widen with wonder as his glans pressed on her prostate and looked down to see dribbles of precum staining her panties.

Candi had never felt anything that felt so wonderfully painful. Her sphincter seared a little as it stretched to accommodate Mitch’s swollen organ and her anus ached dully as it distended when his cock filled the snug void. A warm, rippling sensation unlike anything she had ever experienced radiated from her prostate. Mitch was fully inside her, his scrotum swinging back and forth against her perineum. He was smiling down at her.

“Are you ok darling?” he asked.

“Sure. Just take your time. It’s a little painful but I like it,” Candi whispered.

Mitch kissed Candi and thrust his tongue into her mouth as he slowly began to fuck her, easing his engorged cock almost all of the way out of her anus and then slowly pushing it back inside her. Mitch fought off his orgasm, wanting to enjoy every scintilla of delight as he took Candi’s anal virginity. He could feel her responding under him. She was kissing him back with unbridled passion, her arms locked under his shoulders and she had lowered her legs and wrapped them around his waist, pulling him close to her each time he thrust.

The intensity of Candi’s responses increased proportionally to the quickening of Mitch’s thrusts. Her sphincter was a fiery ring emitting sparklets of delight as Mitch’s cock slid in and out of it. Her anus radiated intoxicating freshets of carnal pleasure and her prostate throbbed with a deep satisfying resonance. Her cock was hard and each time Mitch thrust forward his belly rubbed against her aching organ causing her to saturate her panties with pre-ejaculate. From his laboured breathing and forceful jabs Candi could tell that Mitch was close to extremis.

She too was close to orgasm, her whole body was an incandescent reservoir of sexual delight. Waves of pleasure propagated from her rectum which coalesced with the intense tingling coming from her penis and then washed over her whole body, inciting Candi to utter profane words of encouragement as Mitch hammered away at her virgin asshole. She scoured her legs along his delicate flawless flesh knowing that the feel of her silky nylons would encourage him to fuck her harder and faster.

He groaned into her mouth and his body tensed as he slammed his cock all the way inside her and Candi felt it pulse and tremble. She orgasmed right along with him, her cock pressed against his body, the material of her satin panties stimulating her throbbing appendage as she squirted her essences into the fabric. She felt Mitch’s cock judder as he inseminated her, his hot viscous milt filling her anus which was in turn was undulating, milking every drop of semen from his scrotal sac.

As their orgasms flowered, the two lovers gripped each other almost viciously as they kissed. They clawed, scratched and pounded their bodies against each other. Mitch was gripping Candi’s buttocks as he slammed his cock in and out of her. Candi frantically scissored her thighs against his flanks and raked her nails down his back, encouraging him to ravish her, to fuck her into orgasmic bliss. Mitch could feel Candi’s hot slithery spend smearing his belly as her ejaculate burst through the front of her panties and anointed his flesh. He was happy that he had made her orgasm at the same time as he had.

After what seemed like an eternity Candi came down from her orgasmic high and was content to lie under Mitch with his cock still inside her while they kissed and stroked each other affectionately.

“Well… how was it?” Mitch gazed sown into Candi’s pretty eyes

“Is awesomer a word?” Candi giggled.

“Next time do me doggy,” she looked up at him, her face a picture lasciviousness.

“Who says there will be a next time?” Mitch teased.

“Oh, there will be a next time Mitch. I can feel you becoming fully hard again inside me. You want me and I’m going to let you have me. Now get off me and I’ll get on my hands and knees so you can go really deep,” Candi wriggled underneath him seeing the yearning in his eyes.

This was the moment Candi realised that the power in this relationship was vested in her. Mitch wanted her so badly that she could sense if. She was the pretty young woman who Mitch desperately wanted to posses and Candi knew that there would be others after Mitch. Lots of others. But she would decide who, where and when the boys who desired her got to sample her delights.

When Sharon came home from her date she wanted to know everything and Candi told her. It felt a little incestuous discussing her sex life with her sister but Sharon just listened with awe and fascination as Candi told her about how wonderful it felt losing her virginity.

“I get guys asking me for anal all the time. It’s like they’re fixated on it. Personally I’m not a fan and I have a perfectly serviceable vagina so I don’t understand why they want to fuck me in the ass. But you have different equipment so I guess you find it more pleasurable,” Sharon quipped.

Sharon could see that she might have gone a little too far so she changed the subject.

“Hey! Cheer up. I have a present for you,” Sharon leapt off Candi’s bed and went to her bedroom and returned a few seconds later.

Sharon held up a cheerleader uniform hanging from a plastic clothes hanger and Candi got off the bed to take a closer look. The uniform consisted of a red body-hugging lycra top and blue pleated micro miniskirt. In her other hand Sharon held a pair of red spandex spankies. The uniform was in the Joidale College colours. Kyle had a bodysuit in the same colours that he and his all-male cheer squad wore when performing.

“Try it on, I want to see you in it,” Sharon said enthusiastically.

Candi took the skirt, top and spankies from Sharon and inspected them. They were very well made and Candi was sure that they would fit.

“Wait, I almost forgot!” Sharon ran back to her room and returned with a package containing a pair of stoned fishnet tights.

“Wear a pair of glossy fleshtone pantyhose underneath the fishnets and your legs will look amazing,” Sharon seemed more excited than Candi.

Sharon was correct however. When Candi came into Sharon’s bedroom dressed in the cute little cheerleader uniform, her long legs swathed in glossy hose with the sparkly, rhinestoned, fishnets over she looked incredible. Candi had put her hair in a ponytail and wore dramatic theatrical makeup.

“Wow! You look so good! Are you tucked?” Sharon smiled cheekily.

Candi lifted her pleated skirt and revealed a perfect Vee in the front of her spankies.

“Can you perform like that?” Sharon asked.

Candi felt a little self-conscious but Sharon had been the one to teach Candi her first cheerleading routines so she tried a few out. She found that she could, jump, strut, cartwheel, tumble, kick, pike and perform as well as, if not better, than when she wore her male cheerleader costume. She finished with a slow split, then catapulted up to the standing position and finished with a dramatic shablam.

Sharon clapped her hands together enthusiastically to show her appreciation.

“It’s a shame that you can’t perform dressed like that at Joidale. You would be an instant hit and some of those straight college boys might get ideas that they shouldn’t,” Sharon said offhandedly but the wheels in Candi’s head were already spinning.

Joidale College, Massachusetts – 1985

Candi drove most of the way to Joidale dressed enfemme in cutoff shorts, tube top, pantyhose and pleaser heels. She stopped five miles from the college, removed her makeup and female apparel and adopted her Kyle persona. Throughout the journey she had been scheming and plotting.

Whilst Kyle was breezing through his way through his drama studies he was struggling with most other subjects and falling below a B average meant losing his scholarship. Being the head cheerleader he was popular with the jocks, and the academia majors liked him too, but popularity did not translate into academic merit.

He put is plan into action at the next cheerleader training session. Jaws dropped and some students even gasped when Candi strutted out onto the stadium field dressed in her red body-hugging lycra top, blue pleated micro miniskirt, sheer-to-the-waist flesh-toned pantyhose with the stoned fishnet tights worn over, her hair in a ponytail, wearing theatrical makeup. Before anyone could say anything she ordered her squad to go through their pyramid routine which they did although they were dumbfounded. When everyone on the field witnessed Candi at the apex of the pyramid they were astounded. She looked amazing and her performance had been dazzling. She was a star!

It was after that routine that the football coach and several faculty members shut down training and led Candi to the coach’s office. Candi could feel the bemusement and in some cases downright anger coming from the teaching staff who were astonished at what they had just witnessed.

“Ok, before you start, think about this. My sister dressed me up in her cheerleader costume as a lark and got me to perform some cheers with her and her friends. We were really good and then I thought how novel it would be if the head cheerleader of our all-male squad was a girl. Not a real girl of course but me dressed as a girl,” Candi took a deep breath and continued.

“We are an all-male college so we can’t use a real girl but you can imagine how intrigued everyone is going to be to see me perform as Candi, a name I have chosen because it’s close to Kyle. It will be a crowd-pleaser, increase attendance and bemuse the opposition,” Candi waited a beat for the faculty members to respond.

They argued amongst themselves going back and forth. The haters were dead against it but Candi was surprised to find an equal number of the faculty were in favour of Candi’s proposal.

“Lookie here! I’m head coach and it’s my boys that the cheer squad support. I think Kyle’s… or is it Candi’s, concept is novel and a great idea. I say we try it for a while and see how it goes,” Coach Ingram growled.

And that was that. The rest of faculty rolled over and agreed to try it out with caveat that the ground announcer specify that ‘Candi’ was in fact Kyle Kennedy performing in drag. The first part of Candi’s plan had come to fruition.

Candi became an instant hit and the stands were packed to see her perform. First there was the novelty factor, many people were curious to see a boy dressed as a girl who looked so realistically feminine. Cheerleaders and football fans from nearby colleges and high schools came to see her perform and to witness the intricate routines that Candi had choreographed that put her out front as the star of the halftime show. And of course Candi was intensely aware that some of the boys were attracted to her, although they would never admit it.

Candi had been given four weeks to prove to the faculty and the Dean that her brainchild would not bring the school into disrepute or make the cheer squad or football team a laughingstock. The collegiate papers and local press were generally positive, there were no scathing reviews and their stories centred around the novelty of Candi performing enfemme and the brilliance of her performances rather than expressing a view that what she was doing was in any way lewd. The alumni, teaching staff and student body remained divided but over time they grudgingly accepted that Candi’s performances were a drawcard at the stadium and eventually most of her detractors lost interest in the subject.

But not all were in favour. Candi knew that several members of the faculty were set against her but she thought that Coach Ingram was on her side and had noticed the appreciative glances he cast her way. It was time to cement Candi’s position as head cheerleader.

It was Friday evening after the big game with the stands empty, the stadium lights extinguished, the supporters and players carousing in the local bars. Coach Ingram sat in his cramped office with his feet on the desk drinking scotch and smoking a stogie satisfied with his team’s performance but thinking of how they could improve when Candi entered, a miasma of perfume announcing her presence.

The Coach looked up from his playbook a little surprised to see her and not for the first time had to remind himself that it was not some pretty coed standing before him but Kyle Kennedy dressed as girl. He couldn’t help but let his eyes roam over her lithe body, broad shoulders, trim waist, curvy hips, perky ass and those incredibly long legs. He knew that her pert breasts had to be prosthesis of some sort but that was of little consequence to him. The only distracting feature was that, although there was no evidence of it, Candi was packing a pecker somewhere in those tights.

She had let her hair down and it was damp from the shower, her pretty face framed by her tousled blonde locks. Her makeup was fresh and no longer theatrical, rather it was dramatic and emphasised her glacial green eyes, sharp cheekbones and full lips, more fashion model than cheerleader. Her tunic was fresh, not stained by perspiration from her performance that evening and even a troglodyte like Leonard Ingram understood that Candi had showered and changed after the game… but for what reason? Why was she presenting as Candi and not as Kyle?

Candi closed and locked the door, the gesture not lost on Coach Ingram. She turned her back to him and bent down and picked up a pencil off the floor taking an overly long time to do so. She was not wearing her stoned fishnets or glossy tights but fleshtone sheer-to-the-waist pantyhose. Nor was she wearing her spankies. The Coach had magnificent view of her ass clad in almost transparent pink nylon panties. He admired her long shapely legs and his cock began to stiffen.

“You must have dropped this,” Candi sauntered over to his desk and dropped the pencil next to his playbook and put a finger in her mouth and sucked on it seductively.

Forty year old Leonard Ingram had been quietly let go from his last coaching position at a coed college in California two years previously for allegedly having inappropriate relations with at least two female students. To be fair, neither of the girls were minors and neither of them had lodged complaints but he’d been caught in a compromising position with one of the cheerleaders.

Nothing explicitly sexual was taking place but the coach had his hand on the girl’s thigh and she had her hand outside the front of his tracksuit pants. His resignation had been accepted with the caveat that no record of the allegations be put on his résumé. He had taken the position of Coach at Joidale because he had a thing for pretty coeds and didn’t want to be tempted again.

“What are you doing here?” Coach Ingram growled, clearing his throat.

“Well the four week trial period is over and the faculty will decide if I can continue to perform as Candi on Monday. As coach of the football team your say will likely sway the faculty and I was wondering if there is anything I can do to garner your support,” Candi gave Leonard a beatific smile.

“Is that what the little performance with the pencil was all about? Let me tell you something Candi. If you were a real girl you would be in real trouble right now because you are just my type. But pretty and sexy as you are, you are not a girl, so don’t think your little performance is going to sway me one iota,” the coach said, knowing that he was telling a half-truth.

“But I look like a girl, see,” Candi hiked up her little pleated skirt and gave the coach an unobstructed view of the perfect Vee in the front of her panties.

“How the fuck do you do that?” Coach Ingram could not take his eyes off Candi’s pubis.

“You don’t want to know Coach. I might not have a pussy but I have a warm wet mouth and my ass is to die for,” Candi spun around and exposed her perky buttocks.

“Have you ever fucked a girl up the ass Coach? It’s a lot tighter than any pussy you have ever fucked,” Candi turned to face the coach and gave him her best seductive smile.

What happened next was better than anything Candi could have hoped for. She was hoping to get away with giving Leonard Ingram a blowjob to both secure his support and if necessary blackmail him into endorsing her quest.

Coach Ingram leapt from his seat, crushing out his cigar as he did so. He picked Candi’s petite body up in his strong arms and dropped her down on his desk. He was a handsome man with thick wavy hair, deep dark eyes and a muscled physique and when he leaned down and pressed his mouth to Candi’s she didn’t mind one little bit despite the taste of scotch and tobacco on his breath.

“You little hussy!” he hissed as he forced her legs open and stood between them.

His pulled his tracksuit pants down to his knees along with his underwear exposing an impressive organ that was semi-erect. He closed his mouth on Candi’s and slipped his tongue into her mouth and his hands fondled her thighs.

“I don’t want to see it or touch it,” Leonard hissed as his hands worked their way up Candi’s legs.

“You won’t have to. Just pretend I’m a girl and nothing I do or say will spoil the illusion,” Candi whispered as she reached for his member and improved his erection.

She rubbed his cock against her pantyhosed legs knowing that the gossamer nylons would stimulate the sensitive nerves of his fraenulum and glans. She felt a dribble of precum soak into her nylons and the coach groaned into her mouth as his fingers sought her crotch. Candi eased aside the gusset of her panties and using a long, manicured bright red fingernail she opened a hole next to the seam of her pantyhose.

“Let me do it,” she whimpered when the coach began to stab his cock into her groin.

She guided his erect penis between buttocks and lodged the glans in her sphincter and was thankful that she had lubricated herself just in case, when Leonard Ingram drove his cock all the way inside her tight asshole. He kissed her fervidly as he humped her, his thrusts hard and fast, his hands clenching her panty-clad buttocks to prevent her sliding across the tabletop. Candi wrapped her legs around him and held him close, returning his kisses, wriggling her ass to encourage him.

It was over as quickly as it began. Coach Ingram roared like a bullock as he jackhammered his cock in and out of Candi’s tight anus, expressing his issue inside her, his semen further lubricating her tight passage. The ‘thwok’ ‘thwok’ ‘thwok’ sounds of his pubis banging against her buttocks and thighs as he inseminated her filled the silence along with his groans and moans.

Candi came quietly in her panties, her cock still bent painfully against her taint. The coach’s steely hard, thick cock stretching her sphincter and banging against her prostate induced a spontaneous and unwanted orgasm. She was confident that the Coach wouldn’t notice the puddle of semen in the back of her panties and her cock was still effectively tucked. She did not want to spoil the illusion that she was a girl for Leonard.

The aftermath was a little awkward but it was agreed that the coach would give Candi his full support at the faculty meeting on Monday and in return Candi would reward him with sexual favours at least once a week for doing so.

Later in her dorm room Candi sat at her desk, her panties still moist from Coach Ingram’s semen leaking from her ass comingling with her own ejaculatory emissions, and started making a list of students who were performing exceptionally well academically whom Candi had noticed had taken more than passing interest in her.

At the top of the list were Peter Longmire and Robert Carlyle.

The End
(or is it?)