Coffee Shop Girl

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Coffee Shop Girl. - A tale of envy, vengeance and subterfuge that turns into something quite extraordinary

Author’s note: This story was inspired by my very good friend and fellow author Talespin who told me about events in his life that have recently transpired. It is an erotic tale that requires some suspension of disbelief but is based very loosely on the lives of two real people. All writers crave encouragement and constructive criticism so feel free to do so.

Coffee Shop Girl

Carey Davenport sipped his coffee and looked at the want ads in the student paper. He was looking for part-time employment and not having much luck. Being a college student he couldn’t hold down a regular job and the jobs being advertised paid no better than the one he already had, flipping burgers at a multinational fast food chain. Minimum wage for slave labour.

Balwyn was a college town and well-paid casual work was snapped up very quickly. Most of the students worked part-time jobs to supplement their meagre stipends except for those who came from well-to-do families and there were very few of those at Balwyn College which wasn’t exactly Ivy League.

The surplus of young, eager, unskilled labour meant that business owners could pay pretty much whatever they wanted. Girls seemed to have more opportunities than boys, especially in the service industries. Would you rather be waited on by a pretty girl in a short skirt or an awkward young man just out of adolescence? It was a no-brainer and Carey had to admit that he was a little jealous.

Take this place for instance: pretty young girls wearing too much makeup, short skirts, angora sweaters a size too small or close-fitting blouses with one too many buttons undone, sheer pantyhose or opaque tights and block-heeled pumps. They flitted around the store in a miasma of perfume. There was nothing overtly sexual about them but they exuded sensuality and the customers obviously appreciated them.

Carey looked enviously at the tip jar on the counter. It was overflowing and most of the bills were tens with a smattering of twenties.

“Thank you sir; you are very generous,” a pretty little thing as smiled at a businessman who had dropped a sawbuck on her tray.

She sashayed away from the table, the business man’s eyes staring appreciatively at her trim ass.

Carey looked around the establishment. It was packed and most of the customers were men. There weren’t many college kids because the prices were exorbitant. The clientele was mostly business types, salesmen or tradesmen. Some lingered over their coffee reading papers or books, many had their noses buried in their phones and some had set up work stations, taking advantage of the free wifi. Most of them looked furtively at the college co-eds fluttering around the tables delivering food and beverages or bussing tables.

The coffee was good but it was pricey, as was everything on the menu, but that didn’t seem to affect the clientele. Carey began to seethe a little. It was unfair that these pretty little things were being used my management to draw in customers. He was also jealous of the attention that the waitresses seemed to pay to the more affluent customers.

There wasn’t a single male employee that Carey could see but maybe there were a few slobs out back working the grill or washing dishes, certainly not in front of house. This wasn’t the kind of place you lined up and ordered and waited for the barista to call your name when your beverage was ready. When customers ordered their coffee to go they were given a stick with a number on it and waited on stools set up next to a long bench that ran along the big glass windows and the girls delivered your to-go order.

This encouraged customers to tip the servers even if they were just getting takeout. The majority of the customers were met by a hostess who seated them at tables where they drank coffee from stoneware coffee mugs and ate sandwiches off elegant stoneware plates. After sitting there a while, taking his time sipping his overpriced brew Carey soon fathomed the business model.

“Excuse me?” Carey hailed one of the servers.

The pretty teenaged girl summed him up immediately: a fellow student who wouldn’t tip much and was taking up valuable realestate but she put on a false a smile and wandered over to him.

Carey was a very handsome young man. He was slim built and stood 5’9”, his long legs and snake-hips clad in black skinny jeans. His hair was ash blonde and shoulder length, his eyes emerald green, his cheekbones perfect and his lips sensual. The girl was obviously attracted to him despite his poverty. Her name badge read Kyla, a ditzy name for a ditzy girl.

“Yes sir?” she smiled sweetly at him but Carey knew that the smile was forced and that she was sizing him up.

“I was just wondering…doesn’t this place employ any men?” Carey asked.

Kyla’s smile turned into a frown.

“Well that’s a question for management,” she replied curtly.

“Can I ask you how well does the job pay?” Carey continued.

The girl’s frown deepened but Carey gave her his best smile and she melted a little.

“I’m just asking because I’m looking for work and most part time jobs for college kids suck,” Carey brushed his hair out his eyes, a trick he used to draw attention to his emerald green eyes that had melted many a girl’s heart.

“Look. I’m not supposed to say but the owner only employs women to work front of house. Apparently there is some loophole that allows him to do so, like Hooters. There are a few guys working out back but the real money is made by us servers. We’re paid well above minimum and the tips are very good,” the girl allowed, looking around a little nervously.

“That doesn’t seem fair,” Carey tried no to sound whiney.

The girl was obviously keen to move on and get on with her job. Carey had seen her stop and flirt with two besuited businessmen who had tipped her generously but she had little time for this college boy, despite his handsomeness.

“You know what. If you don’t like it, complain to your congressman or better yet… you're a pretty boy. Put on some makeup, a skirt and heels and apply for a job. They say pretty boys make pretty girls,” the young woman replied testily, the sarcasm heavy in her voice.

“If you're finished your coffee I request you move along because we have customers waiting,” she dismissed him and turned on her heels and strode away with a flick of her skirt.

Carey was seething. He dropped a one dollar tip next to his check and stormed out of the coffee shop.

Alone in his dorm he was still seething. He should be working on his first dissertation which was due at the end of the semester but instead he was drinking Jack and Coke. He’d stopped at a liquor store that played loose with the state liquor laws and used his false ID to buy the bottle. The newspaper was still open at the want ads. The Perky Brew was advertising for ’Hard working young women eighteen to twenty-two who are approachable, upbeat, and attentive to the needs of our customers.’

“Why not just write dumb sluts willing to shake their asses and rub their tits in the faces of our leering clientele”, Carey screwed up the newspaper and threw it across the tiny room.

Carey didn’t quite know what had got him so riled up about The Perky Brew. He wasn’t a warrior for social injustice, he was just angry that pretty young girls had the upper hand when it came to employment opportunities in the college town. He’d like to show them. To make the owner look stupid and expose his sexists work practices. The drunker he got the more outrageous his thoughts became.

Then he recalled what Kyla had said to him: Put on some makeup, a skirt and heels and apply for a job. They say pretty boys make pretty girls.

When Carey was eighteen he had gone through a brief Goth period mainly to try to get Goth girls. He’d adopted the homogeneous dress style, worn makeup and dyed his hair black. One night a couple of Goth girls had put him in drag before they attended a rave. He’d worn a black skirt, fishnet tights, a latticed blouse and heavy makeup with his hair teased out. His own boots had completed the look. It was more androgynous than femme but he did look more like a girl than a boy. He had vague recollections of making out with some of the young men whose sexuality was fluid.

The Goth fad had soon passed but he remembered that he did feel very feminine and had questioned his sexuality at the time. The memory of the rave had been repressed because he had partaken of mind-altering substances during the evening but now the memory emerged and fired his imagination. What if Carey became a ‘pretty girl’ and got a job at The Perky Brew and revealed himself to be male? That would show them!

Carey was just drunk enough to convince himself that it was a good idea.

Carey’s current squeeze, Vickie, was away for the week. The Balwyn Broncos football team cheerleaders were in a training camp prior to competing in a Varsity cheerleading competition. Vickie was a cheerleader and liked to show off her tanned, toned legs in rah-rah skirts and her perky tits in tight tops. Carey had no doubts that when on the road with the Balwyn Broncos Vickie played around with the football players; their relationship was casual with no expectation of exclusivity. He knew that Vickie was only attracted to him because of his handsomeness and his intelligence but she had a thing for jocks too.

The dorm was co-ed and Vickie lived three doors down. While he still had his drunken resolve Carey went down to her room and used the key she had given him to sneak into her room at night and opened the door. Her room smelled of her perfume, cosmetics and other feminine odours which had always delighted him some way. He took a suitcase and filled it with some of Vickie’s clothing and makeup and snuck back to his room but then he started feeling guilty and stupid. He left the suitcase unopened and crawled into bed. It was a dumb idea and he’d return Vickie’s clothes and makeup the next day.

But he didn’t.

Instead he wandered down to the Perky Brew to get a to-go coffee to nurse his hangover. The place was buzzing and the pretty girls pranced around the establishment smiling at the customers, flicking their skirts and flaunting their bodies. Carey’s jealousy and resentment returned and he took his coffee back to his dorm room.

Vickie had often remarked that she was jealous of his soft flawless skin, high cheekbones, his big eyes and sensuous mouth. In high school his slim build and effete looks had precluded him from joining the ranks of the jocks, motor heads and the roughhouse types, he’d skirted around with the Emos and artsy theatre majors mainly to get girls. But this was college and most of the students formed alliances based on their academic majors or common interests. Carey was more of a loner and he preferred it that way.

At nineteen Carey still hadn't grown in much facial hair and his single attempt at growing a goatee had been an abject failure. He shaved the few rouge hairs that sprouted on his chin about once a week. He put on his bathrobe and went down to the communal bathroom where he showered and cleaned his teeth. Returning to his room he plucked a couple of hairs from his face and two whispy bristles from his chest. Other than that his body was hairless.

Carey had used makeup during his flirtation with the Goth subculture but that style of makeup wouldn’t work for the Perky Brew. His loose affiliation with the theatre arts kids had landed him a couple of very small roles in minor productions so he was comfortable around cosmetics and being able to immerse himself in a role but he had never had to wear drag or present femme so he was no expert, but fifteen minutes of searching YouTube produced what he was looking for. He opened the makeup kit he had filched from Vickie’s dorm and followed the online makeup tutorial.

When he was finished Carey was amazed at the results. He hardly recognised the attractive young woman looking back at him from the mirror. The arched brows, the eyeliner, mascara and eyeshadow embellished his large green eyes. A light coating of rouge defined his slender nose and pronounced cheekbones and the lipstick plumped his lips into a seductive bow. Carey painted his fingernails the same colour red as his lipstick and admired the results. They looked so much sexier red rather than black.

He needed to do something about his hair but not much. His shoulder length ash blonde hair was his showpiece and he spent more than he could probably afford having it styled piecy, cut with short and longer layers to give a chic tousled appearance. He combed out the bangs and did his best to cut them level between the tops of his brows down to the tips of his lashes. Before he looked pretty, now he looked hot. Carey took a selfie to use as a template for future makeup endeavours.

Carey shucked out of his bathrobe and looked at the pile of Vickie’s clothing that he had dumped on his bed. He’d watched Vickie dress plenty of times and knew in what order he should dress. For cheerleading Vickie wore Peavey light suntan pantyhose that were sheer to the waist without the cotton gusset. Carey opened a pack and marvelled at the shiny, silky, smooth fabric. Vickie would let him play with her legs for hours sometimes as a prelude to sex when she wore her cheerleader costume and he adored the feel of the gossamer textile on her legs.

Carey recalled the last time they’d had sex in her room in this very dormitory. Vickie had returned from a Broncos game where she had been cheerleading. She was still wearing her bright yellow, tight-fitting cheerleader uniform. It clung to her lithe body accentuating her trim waist, her perky bosom and her pert buttocks, just like it was meant to do.

She was sweaty and the heavy makeup she wore under the stadium lights had run and her hair was teased out and dishevelled and it made her look sexy as all hell. The little skirt barely covered her ass and her long legs clad in the shimmering hose drew his attention. She had been drinking at the post game party and she was feeling amorous.

She had thrown her carrybag in the corner and flopped down on the bed, her legs akimbo. Vickie wore high-cut spandex polyester briefs that she called spankies under her cheerleader skirt. They had the golden horseshoe Bronco logo on the rear and were bright blue.

“You want some?” Vickie had run a red fingernail along the crotch seam of her spankies.

Carey had needed no further coaxing and dropped trou and fell on her.

The sex was hot, quick and messy. He had crushed his mouth on hers, further smearing her already smudged lipstick. Her mouth tasted of stale beer and something else that Carey thought might be semen but he didn’t want to think about. As he kissed her passionately he inhaled the scent of her sweat and the remnants of the perfume she had worn to the game.

Vickie knew that Carey loved the scent of Dior Poison but she refused to wear it out with him, instead wasting it by wearing it when she went cheerleading but Carey had more important things to think about right now. His cock was rubbing on her pantyhose-clad thighs and Vickie was wriggling and giggling underneath him, knowing that he loved to hump her when she wore her little yellow skirt and spandex bodice, she used that to her advantage.

He could feel her nipples harden under the tight lycra bodysuit and was sure he could smell her cunt. He pressed his cock into her spankies and felt the outline of her labia through the fabric of her briefs and pantyhose and Vickie wrapped her legs around him and held him close as she writhed beneath him.

She was hot and ready for it and Carey wondered if maybe one of the football players had got her that way and if that accounted for taste of semen on her breath. It didn’t matter. Carey’s cock was steely hard and Vickie had guided it inside her spankies and pressed it into her cunt.

She used her sharp fingernails to open the crotch of her Peaveys and his cock slid into her cunt like a sword into a well-oiled scabbard.

Vickie held him close with her legs wrapped around the small of his back, her arms enveloping his narrow shoulders and she began to fuck him. She knew that he adored the feel of her nylons on his skin and she scissored her legs against his flanks and bucked upwards to meet his frenzied thrusts. Her mouth was warm, wet and sloppy, her tongue slithering in his mouth.

Vickie could do this thing with her vagina where she was able to undulate it so that it gripped his engorged cock like a silken glove and milk him.

He exploded deep inside her, ramming his cock in and out of her clunge as she flailed and moaned beneath him, howling and groaning as her orgasm erupted. She clung to him, grinding her labia into his pubis so that it pressed on her clitoris, using him like a fuck-toy to meet her carnal needs.

When it was over she had unceremoniously pushed him off her and told to go back to his room while she showered and changed and that night over pizza and beer he had wondered how long their relationship would last. She was a lousy girlfriend and he had to admit that he was a lousy boyfriend.

The images faded from his memory as he returned to the task at hand which was to find some of Vickie’s clothing that suited his purpose so that he could pretend that he was in some way just like her.

Having worn fishnet tights during his Goth period he knew how to put on the pantyhose but he was surprised at how wonderful the diaphanous hosiery felt against his skin. Fishnets felt scratchy and coarse while the Peaveys felt silky, delicate and lustrous. The gusset was tight around his buttocks and caressed his genitals which Carey kept shaved as was the current trend.

“God, they feel amazing. If I was girl I’d wear nylons every day,” Carey whispered as he ran his fingertips along the sheer fabric.

He rummaged through the assortment of underwear he had stolen from her room until he found what he was looking for and fished out a pair of pristine white, full-cut satin panties and shivered with delight as he slid them up his legs. The satin panties slid along the silky hose, eliciting sparklets of pleasure that Carey found quite wondrous. As he pulled them tight the bulge of his semi-hard penis tented the crotch and Carey knew he would have to do something about it.

While he waited for his tumescent member to deflate he used his old pal YouTube to find a tucking tutorial. He was not comfortable at first with his testes pushed up inside his inguinal canals but he gradually became used to it. He wrapped his penis in his empty scrotum and tucked it back along his perineum and pulled up the panties and pantyhose tight and snug to hold everything in place. He did this lying on his back on the bed and when he stood in front of the mirror he was amazed at what he saw.

He was looking at a tall, very pretty young woman who although she was flat chested, had a perfect Vee between her legs. Now Carey really believed that he could pull this charade off. He found a short A-line navy-blue skirt that fitted him perfectly and looked in the mirror and was very happy with what he saw. Now he had to deal with his upper body.

A lot of the girls that worked at the Perky Brew didn’t have big breasts. Most had small perky tits just like Vickie. He found a brassiere that fitted his slender frame and stuffed the cups with pantyhose. That would have to do for now. The straps of the bra cut into him a little and the B-cups were not the right consistency to stand up to tactile examination but the shape was about right. They would have to do for now and when he put on Vickie’s mauve satin blouse he presented a pleasing figure.

A very attractive nineteen year old girl stared back at him from the mirror. The obvious thing he was missing was shoes. In his drunken haste last night he had forgotten all about them. He also realised he didn’t have any jewellery or a purse or a handbag.

It was time to put his little charade to the test. He could hear people coming and going outside in the corridor and although Vickie’s room was only three doors down he would inevitability have to pass some fellow students. He set his resolve and opened the door to his dorm room and padded to Vickie’s room in his stocking feet. He received appreciative glances from a couple of boys who were gathered near the notice board and two girls giggled when they saw his stockinged feet, probably thinking that the girl was doing the walk of shame and had forgotten her heels.

Safely inside Vickie’s room Carey went through Vickie’s extensive shoe collection and found a pair of block-heeled pumps similar to those that the girls at the Perky Brew wore. He stuffed his feet into the shoes, the slippery pantyhose helping but the shoes were at least one size too small and squeezed his feet. In heels Carey was even taller and looked like a young Allison Janney with his blonde piecy hair but the heels were squeezing him painfully. He was about to admit defeat when Carey realised that he wouldn’t have to wear the shoes to and from The Perky Brew, just during the interview. If he got the job he could buy shoes that fit.

He rifled through Vickie’s jewellery drawer and found a box with a necklace, matching earrings and bracelets. They were cheap imitation silver which was probably why they were still in the box and relegated to the back of the drawer but they were perfect for him. He’d had both ears pierced in his early teens and the little drop earrings looked cute dangling from his lobes as did the necklace and bracelets around his neck and wrists.

He snatched up a cheap spaghetti-strapped purse and put the strap over his shoulder and looked at himself in the mirror. He was stunning. His clothes were not quite as well fitting as they should be but he looked like a very attractive young woman. All he needed now was to apply for the job.

Carey was fortunate that his name was gender neutral so he wouldn’t have to invent some fictitious name or have a problem when he had to present a social security card. Using his own name also meant that he would be unlikely to forget a pseudonym if he was under pressure.

Carey Davenport went online and submitted an application for a job as a waitress at the Perky Brew. The online application required the applicant to upload a full body shot and a face pic which Carey thought was very misogynist but wasn’t it the owner’s misogyny that Carey wanted to expose?

With the application submitted Carey relaxed and began to think seriously about what he was doing. He was now fully sober and his resolve was beginning to wane when his phone pinged. If Carey wanted the job she should present herself for an interview at The Perky Brew that very afternoon. The manager, one Desmond White, made it clear that there were plenty of applicants for the position and that Carey should be grateful that she was even being considered. It was hinted but never actually stated that she was top of the list because of her looks. Desmond White was careful to use words like poise, gracefulness, appeal, charm and presentably rather than actually commenting on her face and body.

Carey’s resolve returned and he spent the next few hours practicing walking and talking like a young woman and consciously used feminine gestures. Carey used the few acting skills he possessed to fully immerse himself in the role of Carey Davenport, a shy ingénue looking for work to help pay her way through college. He mentally became ‘Carey the college girl’ thinking of herself as a young woman. Carey was confident that he could pass as a girl. It would only be something Carey said or did, a slipup if you will, that would betray her true gender.

Walking to the Perky Brew proved liberating. At first Carey was self-conscious and afraid that she would be clocked despite the confidence she had felt in the dorm but the fear soon dissipated as she settled into just being herself. She noticed that she was being looked at appreciatively by most of the males she passed and her self-assurance blossomed. She was comfortable in her skin. She was Carey: long-legged, pretty co-ed, going for an interview for a job she desperately wanted.

Carey changed out of her sneakers at an outside table and put on her heels. Carey was thinking of herself in the feminine, mentally practicing her backstory, immersing herself in the role. When she had secured the job and worked for a while at the Perky Brew she would write an exposé and was already thinking about what the title of the piece should be. She took a deep breath and approached the entrance to the coffee shop.

When Carey told the hostess that she was here to see Desmond White the hostess pointed to a door next to the counter that had a sign on it reading Staff Only.

“You interviewing for a job Hun?” the hostess looked Carey up and down critically.

Carey nodded, too nervous to talk.

“Cat got your tongue? Well you are certainly dressed for the part,” the hostess, whose name badge read Clarice, said smacking her gum.

“Yes I’m looking for work,” she answered, her mouth dry.

“Well you gotta pretty mouth Hun. Hope you know how to use it if you want a job here,” Clarice chuckled.

Carey bristled. She sensed a little hostility coming from the hostess.

“I can yack it up with the rest of them when I need to. I’ve been here before and seen the wait-staff at work and I’ve read the ad. I understand that I’ll need to be able to be approachable, upbeat, and attentive to the needs of our customers; which I presume means flirting with the clientele,” she was grateful that Clarice had invoked her ire because it caused Carey’s confidence to return.

“Oh no. That’s all true but Desmond White will want you to do other things with your mouth other than just chat pithily,” Clarice opened the door and indicated for Carey to enter.

“Up the stairs, third door on the right,” she smiled sweetly at the naïve ingénue who Clarice knew was a lamb being led to the slaughter.

Carey just nodded and began to climb the stairs, hanging onto the handrail for support as she tottered on her heels. She was conscious that anyone coming up behind her would be able to see right up her skirt and rather than be discomfited by that she was actually a little excited by it.

Desmond White was a small middle-aged man wearing an expensive suit. He was balding with a comb-over, not exactly ugly but a little toad-like. He exuded confidence and his eyes crawled all over Carey’s body as soon as she entered his office. He sat behind his desk and inspected Carey like she was a prize sow. His office smelled of bourbon, cigarette smoke and cheap aftershave.

“Wow! You're a tall one aren’t you? Nice legs, trim butt, pretty face but not much in the tit department,” was how Desmond greeted Carey.

Carey blushed. She could almost feel Desmond’s eyes slithering over her anatomy. His gaze crawled along her legs, up to her waist, stopped briefly at her chest and then onto her face, finally engaging her green eyes which glowered with anger.

This was just what Carey had expected. The girls at the Perky Brew were subject to objectification by their boss and encouraged, or more likely required, to use their assets to flirt with the customers.

She locked her gaze on Desmond’s dull brown eyes trying her best to show determination but also scared that she might be exposed for what she was. All that aside, Carey was secretly flattered that this man found her attractive. It was one thing being able to pass as a girl, it was another to actually be desired and Carey felt a little confused but also a little thrilled.

“Spin for me hun, show me what you got,” Desmond growled.

She couldn’t believe that in this day and age a man would say this to a teenage girl but she understood the power dynamic. The girl needed the money and the man had the power.

Carey spun on her heels and her skirt rode up her thighs as she did so. She spun around three times and then stopped, a little dizzy.

Desmond had gotten out from behind his desk and was standing close to her. Without warning he put his hands on Carey’s hips and pulled her close.

“Don’t worry hun, I gotcha,” Desmond was pretending to help Carey keep her balance but really it was just an excuse to touch her.

She could smell bourbon and cigarettes on his breath and cheap cologne as his face closed in on hers. She felt powerless but also a little elated that Desmond hadn't seen through her ruse. As his lips closed on hers Carey vaguely recalled making out with the Goth guys at the rave. The memory was murky but she remembered how exciting and strangely feminine it had felt to be kissed and groped like that while she was dressed in drag.

There was something strangely intoxicating about being held close by this gross man who was pressing his lips to hers, his hands squeezing her ass, his boner pressing into her thigh. She should have been repulsed but instead she opened her lips and welcomed his tongue into her mouth.

Carey convinced herself that she was allowing her potential boss to feel her up so that she had conclusive evidence that she could use in the dissertation Carey Davenport would write about gender bias, misogyny and sexual harassment in the workplace and in particular in the little college town of Balwyn and specifically at the Perk Brew. She was already imagining the accolades she would receive when her paper was submitted. But for now she just had to grin and bear it. She would endure whatever she had to. Carey didn’t really like what Desmond was doing to her… did she?

Desmond's fingers slipped under her skirt and stroked her thighs and she delighted in the feel of his fingertips fluttering on her pantyhosed thighs. His fingers crawled upward as his kisses became more passionate. When his fingers brushed the front of her panties she baulked.

“Not my pussy. That’s out of bounds,” Carey snipped.

“Ok girly, I get it,” Desmond growled and his hands went to her buttocks and squeezed them instead.

“Is that better?” Desmond didn’t wait for a response as he crushed his lips against hers.

It was better. It was better because Desmond wouldn’t discover the secret in Carey’s panties and also because she actually enjoyed the feel of this slimy man’s fingers kneading her pantied buttocks. Carey pressed her body against Desmond convincing herself that she was doing so to garner more evidence that the Perky Brew was a toxic workplace, not because she was enjoying being kissed and pawed at by this toady tyrant.

“How bad do you want the job Hun?” Desmond broke the kiss and looked up into her face as she towered over him.

“What does that mean?” Carey played naive.

“I pay twenty dollars an hour which is well above minimum and my girls pool the tips. I don’t take a cut. But you’ve seen my business model. Sex sells and you need to be willing to flirt a little and show some T and A,” Desmond winked at her salaciously.

“I can do that,” Carey looked down into Desmond’s beady eyes and nodded.

“I also like to take a few liberties with my girls. Nothing they aren’t giving away for free to their boyfriends anyway but it, shall we say, cements our partnership,” Desmond grinned.

Carey wished she’d switched on the recording device on her phone and subconsciously kicked herself for not doing so. Desmond was a little drunk and his guard was down and he liable to say anything. Anyway it was time to shit or get off the pot as the more ribald might say, or time to cross the Rubicon as the more genteel might put it.

Carey leaned in and kissed Desmond, pushing her tongue into his mouth and then quickly withdrew it. Her hands were clasped behind his neck and she rubbed against him.

“Liberties are fine but my pussy is out of bounds,” Carey whispered and couldn’t believe that she was saying it.

Desmond chuckled and kissed her, his hands sliding up under her skirt and cupping her buttocks. Carey was amazed that in such a short space of time she had become such a floozy. She actually enjoyed feeling Desmond’s hand stroking her pantyhosed thighs and kneading her buttocks. It was something to do with wearing the clothes and pretending to be girl. She was incognito and everything she did while she was ‘Carey the girl’ would have no bearing on the sexual orientation of ‘Carey the boy’. They were two different people sharing the same body.

Carey felt her penis becoming uncomfortably tumescent between her legs. Only her tight pantyhose and panties kept it from springing forward. She kissed Desmond passionately and enjoyed being groped by him. This wasn’t too bad after all. Just a little flirting to secure her employment and she could write all about it in detail in her exposé.

But then Desmond removed his hands from under her skirt and put them on her shoulders and applied downward pressure. Carey had done this enough times with Vickie and other girlfriends before her to know what it meant.

Carey dropped to her knees feeling lightheaded. She knew that she didn’t have to do this. She had enough evidence already to expose Desmond White. She could go public with what she knew or probably even go to the campus police. But she knew it would be her word against his. There would be complications. Carey was a boy dressed as girl and had done so to deliberately to entrap Desmond White. Carey had seen enough porn on the internet to know the definition of a Trap.

Carey was presenting as female and she imagined that Desmond’s defence would be that what they did in his office was consensual or that it didn’t happen at all and that Carey had made the story up. Desmond would certainly not be lying when he claimed that he had no idea that Carey was really a boy. Not that that was particularly relevant but Carey knew that men like Desmond were practiced in escaping the consequences for their actions. She guessed that legally what she was doing was called entrapment.

No. Carey would have to do whatever was needed to get the job and ingratiate herself with the other waitresses and compile corroborative evidence.

Or was it that Carey was surprised that she enjoyed being treated like a girl, being kissed and groped and caressed, and was actually inquisitive as to how it might feel to suck a cock while she was dressed as a girl? Either way she was in a perfect position to find out and the throbbing cock trapped between her legs betrayed her intentions.

Carey had been fellated enough times to know what he liked. It made sense that his female alter-ego would be able to mimic those actions and bring Desmond White to a satisfying climax and secure the job.

Carey dropped to her knees so that her head was level with Desmond’s crotch. She could hardly believe that she was doing it when her hands went to Desmond’s belt buckle and then his flies. She concentrated on her long red fingernails almost like she was having an out of body experience as she unzipped him.

Desmond lifted his gut out of the way to assist Carey as she pulled his trousers down. His pants bunched around his knees. His cock stood proud. It was rock-hard, long and slim with blue veins pulsing through the almost transparent silky skin. A single bead of silvery pre-ejaculate oozed from the pink glans.

It was mesmerising. Carey had caused this man to become concupiscent, a word she would use in her dissertation to send the readers scrambling for their dictionaries. It was her feminine mystique and her beauty that had made this man yearn for her and desire her. It was empowering and sexually provocative.

Carey collected the viscous bubble of precum and used it to lubricate his shaft as she began to masturbate him. Once again vague memories of the Goth rave drifted through her conscience. Had she done this before? She must have and suppressed the memory because she seemed adept at it. Her long fingers with those slut-red fingernails danced along Desmond’s turgid flesh causing him to shudder.

Desmond groaned; his eyes locked on the pretty young girl stroking his phallus.

Carey imagined what it would look like if someone was to suddenly burst into the office. A young college girl provocatively dressed, wearing heavy makeup, her skirt hiked up to reveal her pantyhosed thighs, her feet shod in high heels, masturbating the pudgy balding toad.

Taking Desmond's cock in her hand did not nauseate her as she expected it would. His cock was of generous proportions and felt smooth and silky to her touch. She did feel a little shocked that she had submitted so easily to his desires and that rather than being repulsed, she felt flattered and sexually charged.

Carey softly stroked Desmond's hard flesh making him moan with desire. She gripped it a little tighter and increased the pace using the little droplets of pre-seminal fluid leaking from the eye of his cock to lubricate the substantial organ. She bought her other hand into play and softly cupped his scrotum, gently squeezing and caressing it, making Desmond shudder. It was a trick that Vickie used on Carey and it was having the same effect on Desmond.

She worked on Desmond's cock expertly, bringing him closer and closer to extremis. It wasn't that difficult because she too possessed a penis and she knew how to manipulate it to achieve the greatest stimulation.

Desmond placed his hands on her head. There was nothing rough about the gesture. He was simply indicating his desire for her to use her mouth on him. She allowed him to guide her face into his crotch and she opened her lips and took him into her mouth. She was astounded that she allowed herself to do so without a single qualm.

Carey had been fellated often enough that she knew what to do. She worked her tongue on Desmond’s glans and slid her lips up and down the shaft. She continued to gently squeeze his scrotum and she made sure she looked up at him and kept eye contact while her red lips and velvety tongue worked the head of his penis. Carey felt like a whore but she felt no self-recrimination. She was doing what needed to be done to secure her employment. Wasn’t she?

Desmond looked down on the gorgeous young girl, her beautiful face framed by her ash blonde hair, her exotic eye makeup and brilliant green eyes looking up at him seductively as she used her ruby-red lips and soft tongue to stimulate his phallus. All of the girls in his employ had endured his overtures. One or two had even let him fuck them but most had refused to do anything other than let him feel them up or masturbate him. He had been able to convince a few, like Carey, to use their mouths on him. This nineteen-year-old girl was not the best at what she did but she was far from the worst.

Desmond liked to see the renitence on their faces when he came onto them. Those that refused his advances didn’t get hired and those that did got hired. It was that simple. He considered the waitresses that worked at the Perky Brew his concubines and the fact that they were willing to submit, even though Desmond knew that he repulsed them, somehow made it even more pleasurable.

Licking and sucking Desmond's cock was not as disgusting as Carey thought it would be and under different circumstances she might even have succumbed willingly, even eagerly if Desmond wasn’t some middle-aged toad. Carey imagined what it might be like to fellate one of the hunky football players that Vickie opened her legs for. It would be an experience to put in the ‘spank-bank’ and never tell anyone else about. But for now she concentrated on sucking off Desmond White.

Carey felt Desmond's cock begin to pulse and sensed his orgasm approaching. Desmond tried to push his cock all the way into her mouth but she began to gag and pushed against his thighs. She worked the shaft with her lips and slavered at his glans with her tongue while caressing his scrotal sac. As she felt extremis approaching she lapped at his fraenulum with the tip of her tongue and locked her lips around his throbbing shaft, feeling the veins engorge as his climax built.

Desmond gripped her head tighter and she was rewarded with a mouthful of steaming ejaculate. Freshets of the creamy issue gushed from his penis in long sustained spurts, filling her mouth to the extent that some of it dribbled from her lips and down her chin. Runnels of the glutinous milt dripped down onto her legs, soaking into her pantyhose.

The very lewdness and depravity of the act inspired Carey to almost ejaculate herself. She could feel her cock throbbing in her undergarments, caressed by the silky Peavies and satin panties. The musky taste of Desmond’s semen filled her mouth, the spicy aroma of his spend dribbling down her chin. The sensation of his warm dank spend spattering on her pantyhose was an incredibly arousing and ardent experience that surprised her.

“Ok kid you got the job,” Desmond pushed Carey’s face out of his groin and pulled up his pants.

He waddled over to his desk and tossed a box of tissues at Carey.

“Clean yourself up and go downstairs to see Clarice. She’ll put you on the roster and fill you in how we do things here,” Desmond opened a drawer and pulled out a pint of bourbon and took a hefty chug.

Carey dabbed at her face and her legs, soaking up Desmond's still warm secretions. She tossed the tissues in a metal trash receptacle beside his desk. Now that it was over she felt a little disgusted with herself but she rummaged in her handbag and found her social security card and put it on the desk.

“What the fuck am I gonna do with that?” Desmond took another swig at the bottle.

“Well you are employing me aren’t you?” Carey replied.

“Yes honey but you will be working off the books. You’ll pay no taxes and I won’t be reporting your salary. Is that ok with you?” Desmond’s eyes twinkled and Carey just nodded.

“Fix your lipstick and get the fuck outta here,” Desmond growled and began to sort through the pile of invoices in front of him.

Outside the office Carey used a small compact mirror to fix her makeup and lipstick. She brushed her hair and smoothed out her skirt and checked her pantyhose for runners. There weren’t any and Desmond’s cum stains weren’t obvious and were located under her skirt anyway. She put a hand under her skirt and adjusted her tuck. Her penis was still slightly tumescent but malleable.

She leaned against the wall barely able to stand because her legs were shaking. Carey could hardly believe what she had done. What had first begun as a stupid drunken contrivance to expose unfair work practices, fuelled by jealousy because pretty young girls had an unfair advantage in an oversupplied competitive employment market had somehow led to Carey becoming a crossdressing slattern. How was this even possible?

Carey dropped the compact, hair brush and cosmetics into her purse and put the spaghetti-straps over her shoulder. She picked up the tote bag containing her sneakers. Her feet were already hurting from wearing the high heels but she set her resolve and went down the stairs and found Clarice standing at the hostess station.

“Well, how did it go?” Clarice raised her brows.

“I got the job,” Carey replied, her voice a little husky.

“And did you use your mouth to clearly articulate how much you needed the job?” Clarice smirked.

Carey could feel her face burning as she blushed with shame.

“I’m just teasing you honey. Desmond has already called down and told me to put you on the roster. We all did what we had to, to get a job here,” Clarice nodded at the bevy of provocatively dressed young women flitting around the tables, waiting on the customers.

“Belle, take over my station while I get this girl sorted out,” Clarice called out to one of the older girls.

Carey guessed that Clarice was in her early twenties and Belle around the same age. They appeared to be oldest of the young women working at the Perky Brew.

There was another smaller office beside the kitchen and Clarice led Carey into it and told her to close the door and take a seat.

“Those heels are too small and you won’t last an hour on your feet here wearing them. Get something similar that fits. Other than that you seem to have the aesthetic this place requires. Show a lot of leg and keep your blouse open, although you don’t have much in the way of tits,” Clarice opened a ledger.

“Give me your ID so I can enter your details,” Clarice held out her hand and Carey handed over her social security card.

The card did not list her gender unlike her driver’s licence and college ID.

“You must have done good up there because Desmond told me to keep you off the books. Most of the girls working here are on a reportable income but those who Desmond takes a shine to get paid under the table,” Clarice explained as she wrote in the ledger.

“I see,” Carey said.

More evidence of wrongdoing to go into her project. Not only was Desmond White using unfair hiring practices, sexually manipulating his staff and forcing them to use their feminine wiles in the workplace, he was cooking the books.

“I don’t need to tell you to keep schtum. Your wage will more than compensate you for what you endure here. It’s not just the chauvinism, leering and inappropriate behaviour that you have to put up with, it’s actually very demanding work,” Clarice explained.

“But there are plenty of pretty girls out there who would be willing to do almost anything to take your place. The wages are more than fair and the tips are astronomical,” Clarice continued.

“It’s your job, besides waiting tables of course, to ensure that the tip jar gets filled. Flirting with the customers is encouraged. A little touch or fondle there is to be endured. Most of the girls have favourite customers who they allow to take a few liberties in exchange for big tips,” Clarice raised her brows waiting for Carey to comment or complain.

“After what I just did in the upstairs office, showing a little T and A, as Desmond White so eloquently put it, is nothing,” Carey replied.

“Good girl. You start tomorrow at eight. Does that fit in your schedule?” Clarice asked.

“Sure. Tomorrow is Sunday so I don’t have any classes or lectures,” Carey answered.

“I’ll show you the ropes tomorrow then and we’ll work out a roster that works around your academic timetable,” Clarice closed the ledger.

“See you tomorrow then,” Clarice stood and held out her hand and Carey shook it.

As Carey turned to the door Clarice asked one more question.

“One more thing. Did he clock you?” Clarice asked matter-of-factly.

Carey fell back into a chair in a state of shock.

“Don’t worry honey; I doubt anyone who hasn’t had experience with the transgender rainbow would clock you. My sister is Trans and I helped her in her early days. I’ll give you a few tips tomorrow. You're doing just fine already. I won’t say a word unless you want me to of course, your secret is safe with me,” Clarice placed a comforting hand on Carey’s shoulder.

“Now get your ass out of here and go buy some shoes that fit,” Clarice opened the door and Carey got to her feet.

“If it’s any consolation honey I’d fuck you myself if I was into girls,” she slapped Carey playfully on the rump as she walked out the door.

Carey did not remember leaving the Perky Brew, sitting at the outside table to change into her sneakers, nor the walk back to her dorm. Her head was swirling with confusing and conflicting thoughts.

Should she abandon the whole charade and give up the idea she had about writing her exposé? She could set the whole experience aside and pretend that it hadn't happened, just like she did after the rave. A simple phone call to Clarice Starr telling her that she was no longer interested in the job would solve everything.


There was something about dressing as a woman and adopting femininity as an alternative lifestyle to the one Carey had lived up until now that was intriguing and exciting. If she was honest with herself she was flattered that men found her attractive and seductive. There was something wickedly crude about letting Desmond White feel her up, kiss her and push her down on her knees before him. It was strangely liberating and intensely erotic.

And of course there was the fact that no one except Clarice Starr had clocked her.

At Balwyn College there were a few students who presented as non-binary. The gays and lesbians were well represented and out of the closet, most of them brandishing their sexuality openly. There may even be transgender students attending the college, up until now Carey had not given it any thought. A closet crossdresser would probably not be something extraordinary or unusual but Carey did not want her secret exposed.

Clinging to the notion that she was only doing what she was doing to substantiate her theory that the Perky Brew was a toxic work environment was drawing a long bow by any means. But as our friends across the pond were want to say: ‘in for a penny – in for a pound’. Carey knew that she was just justifying her new-found compulsion to crossdress but it was enough to tip the scales in favour of her continuing to do so.

While she still had the determination to do so Carey left the dorm and drove her ten-year-old Ford Taurus to the Balwyn Mall and went the ATM and withdrew three hundred dollars cash out of her meagre savings. According to Clarice she would soon be earning plenty of cash so she justified the expense and went on a shopping spree. That said, Carey found almost everything she needed at Walmart: skirts, tops, underwear, makeup, costume jewellery and even her new-found favourite Peavey pantyhose. She had to go to Payless Shoes to find two pairs of heels that fit.

Shopping as a girl was far more exciting than shopping as a boy. With her confidence in tact she had no qualms about entering the fitting rooms and trying on her clothes. The one precaution she took was to pay cash for everything so that her purchases could not be traced to Carey Davenport's credit card.

Back at the college dorm she unloaded her purchases and took them to her room. She could hardly wait to try on the ensembles she had purchased in the privacy of her room but there was a pressing chore that needed to be attended to. She used moisturised makeup wipes to take off her makeup and slipped out of her feminine attire. She felt a little reluctant to do so and watching the transformation from tall sexy college girl to a slender young man was disappointing but essential.

Carey the girl became Carey the boy and he packed up the clothing and other accoutrements he had ‘borrowed’ from Vickie into the suitcase with exception of the pantyhose and panties he had worn. He kept those because they were stained with evidence that he had worn them. He unlocked Vickie’s dorm room and carefully replaced everything back where he had found it; well as best he could remember. He put the suitcase away, locked up the room and went back to his own.

Carey used the ablutions to take a refreshing shower and back in his room Carey allowed his feminine alter-ego to take over and she spent the rest of the day practicing her makeup skills and trying on various outfits and perfecting feminine mannerisms. She had purchased four skirt and blouse combinations and thrown in a cocktail dress for good measure. Carey cleared a space in her wardrobe where she could keep all of her feminine requisites separate from her male clothing.

For no other reason than she found it delightful, Carey had purchased a red babydoll satin and lace chemise nightgown and wore it to bed with matching red satin panties. As she lay in the dark she relived the day’s experiences, especially the events that had taken place in Desmond White’s office and was soon sporting a painful erection.

She shucked down the covers and popped her hard cock out of leghole of her panties and reached for the Peavey pantyhose and the panties she had worn that day.

She slipped her erect penis into the leg of the sheer garment and wrapped it tight around her penis and began to stoke it. She didn’t think about fucking Vickie as she masturbated. Instead she thought of some faceless but undoubtedly handsome stranger kissing her, holding her tight, taking her hand and putting it on his bloated manhood. The stranger pressed her down into the bed and climbed on top of her and was about to do something that Carey knew was very wrong but that was when she climaxed. A bubble of creamy white semen erupted through the taught nylon and the apparition dissipated.

Carey was concerned about where her thoughts had drifted to as lay on her side under the covers, curled up with her knees to her chest wrapped up tight and warm in her own dark cocoon. She felt both remorse and exhilaration. The need to climb out of bed and throw all of her feminine requisites into the skip in the car park was only kept in check because Carey’s feminine psyche was in control but that control was tenuous.

If she allowed Carey, the teenage boy to take control of her psyche that's exactly what would happen. She scissored her legs revelling in the feel of the negligée against her delicate flesh and decided that exploring her femininity and pursuing employment at the Perky Brew overrode the need she felt to purge and forget all about living a double life. She pushed down her emotions and finally drifted off to sleep.

Carey arrived at the Perky Brew promptly at eight in the morning. She was wearing a tartan pleated miniskirt, white silk blouse, flesh-toned pantyhose and black wedged high heels. Underneath she was wearing a magnolia coloured bra and panty set. The bra cups were stuffed with cheap pantyhose to give her bosom some shape.

The coffee shop was already busy and buzzing with the Sunday breakfast crowd. Some of them had spread out the Sunday papers on their tables and some had theirs heads buried in their devices, lifting their heads only to ogle the short skirted waitresses or flirt with them. The clientele was the same, mostly affluent men in their thirties and forties. The college kids were getting their coffee and donuts at the McCafe around the corner at less than half the price they would pay at the Perky Brew.

Carey had spent a lot of time in front of the mirror getting her makeup and hair just right, concentrating on the task to take her mind off her nervousness. She was still not convinced that what she was doing was right but she was committed. When she was dressing that morning, as soon as she started putting on her pantyhose and panties she started to feel better, almost serene. Watching herself transform into a pretty girl still fascinated her and along with the serenity, latent sexual energy burned in her groin.

“Glad to see that you’re punctual, come with me to the break room,” Clarice Starr was waiting for Carey at the door.

“Come in, close and lock the door please Carey,” Clarice said as they entered.

The break room was small with a table for four, a row of lockers, a sink and small refrigerator and not much else.

Clarice went over to a locker and took something out of her bag while Carey stood in the middle of the floor, her handbag over her shoulder, unsure if she should sit or remain standing.

Clarice came over and without warning brazenly squeezed Carey’s breasts.

“That just won’t do Carey. What do you have stuffed in there, pantyhose?” Clarice asked.

Carey just nodded feeling a little silly and ashamed.

Clarice produced the items she had taken from her bag and Carey just stared at them.

They were flesh-toned silicone breasts with realistic nipples.

“These are breastforms, sometimes called falsies. They are prosthetic breasts worn by women who have had a mastectomy, drag queens and of course crossdressers,” Clarice held out the breastforms and Carey took them.

“They will look realistic through the fabric of your bra and feel like the real thing through your clothing. These are B-cups which will suit your frame. They used to belong to my sister. I brought them for her when she came out to me as transgender. She’s since had all the surgeries and is now legally a woman living with a nice man in Wisconsin,” Clarice explained.

“Here,” without any compunction Clarice unbuttoned Carey’s blouse and opened it.

Clarice pulled out the balled up pantyhose and slipped the breastforms into the cups and then buttoned Carey’s blouse and allowed Carey to tuck her blouse back into her skirt. Clarice took Carey by the hand and led her to a full-length mirror that the staff used to check their appearance before they went into the shop.

Carey was surprised at the results. The shape of her chest was now perfect and matched her slim frame. The top three buttons of her blouse had been left undone which was how all of waitresses wore their blouses and shirts. Those who opted for angora sweaters wore them tight and low-cut. Carey was tempted to ask if it was compulsory for the waitresses to flash their tits and wear short skirts but the point was moot. Desmond White had made that fact perfectly clear yesterday in his office.

Carey looked at her reflection and could just make out the swell of her breasts through the gauzy fabric of her brassiere. The heft of them felt right and they behaved just like real breasts when she moved.

“Thank you Clarice, how much do I owe you?” Carey asked.

“Nothing provided you do your job and work hard. Like I said yesterday, your secret is safe with me but I can’t guarantee that some of the other girls won’t clock you. That’s all up to you… which reminds me…” Clarice reached out and lifted Carey’s skirt.

“Nice Vee. You seem to have gotten the hang of tucking,” Clarice audaciously stroked Carey’s pubis and Carey shivered at the touch.

“How long have you been crossdressing?” Clarice asked.

“I started recently,” Carey replied, deliberately being vague.

“Well you certainly are passable,” Clarice lowered the hem of Carey’s skirt.

She opened a locker and threw in the balled-up pantyhose and indicted that Carey should put her handbag in the locker then she locked it and gave Carey the key.

“Desmond doesn’t allow staff to have mobile phones in the shop and I don’t blame him. Most of these ditzes would spend all day on them if they could,” Clarice sighed.

“Ok, enough girl talk. Your application says you have experience in fast foods so you are not completely new to this,” Clarice was all business.

“I worked at the Scottish restaurant,” Carey replied and Clarice smiled at the joke.

“Well we are a lot more sophisticated than Mickey Dees,” Clarice smiled.

“Here, pin these to your blouse,” Clarice handed Carey a name bar with her name on it and a second broach to be worn underneath that read ‘trainee’.

While she helped Carey pin the name bars to her blouse she continued.

“I’ll double you up with Kyla today so you can learn the ropes,” Clarice opened the door and indicated that they should leave.

Carey remembered Kyla and wondered if she would recognise Carey as the handsome college boy who had grilled her about how well the girls in the coffee shop were being paid. It was Kyla who had had flippantly told Carey that if he wanted the job he should put on some makeup, a skirt and heels and apply because pretty boys make pretty girls. The irony was not lost on Carey.

Kyla didn’t seem to recognise Carey but it was clear that she not particularly happy to have to train the new girl but Kyla tried her best to be cordial and after giving Carey the once over she led her apprentice into the restaurant.

“The main restaurant is divided into four sections of six tables with one waitress assigned to each section. Then there is the to-go section,” Kyla indicated the section where customers were sitting on stools arranged along a long bench that ran along the big glass windows at the front of the restaurant, each customer had a stick with a number on it on the bench in front of them.

“One girl looks after the little outside dining area. Most girls don’t like it out there because it is a designated smoking area so Clarice usually assigns it to Debbie or Nora because they both smoke,” Kyla looked at Carey to ensure it was all sinking in and Carey nodded.

“The baristas work the main counter making the coffee and the short order cooks and busboys work in the kitchen out back. We place orders using these,” Kyla held up her leather-bound check pad.

“Even a dummy can do it. You simply put the table number at the top of the notepad’s page so you don’t forget the order. Write the number in the left margin of the page and leave three to four lines to write down the order. Continue numbering down the page for the number of people at the table,” Kyla explained.

“But you’ve worked in the food service industry before right?” Kyla asked.

“Yeah, sure,” Carey relied confidently; omitting that her experience was limited to flipping burgers and occasionally working the counter at Mickey Dees.

“Look this job is easy. Smile a lot. Get in close and let the customers feel special, flash your assets and don’t complain if one or two of them cop a feel. You’re no prude right? You can’t be if you’ve passed Desmond’s job interview,” Kyla winked salaciously.

“Come on. The best way to learn is to dive in the deep end,” Kyla led Carey to their assigned section and they went to work.

The rest of the morning flew by and Carey was so busy that she stopped worrying about being clocked. The Sunday morning rush was in full swing and Carey was more concerned with ensuring that she got the orders right and presenting herself as a happy smiling server. Most of the male customers openly ogled and some ‘accidently’ brushed up against her and one cheeky man actually stroked her leg.

It was obvious that most of the clientele were regulars and Kyla knew many by name and went out of her way to flirt with them.

“Remember, the nicer you are, the bigger the tip,” Kyla reminded Carey.

During their twenty minute break Clarice came into the break room and asked Kyla how Carey was working out.

“She’s getting the hang of it. It aint rocket science after all,” Kyla looked up from her phone and clacked her gum.

“Give me a minute with Carey please Kyla, she’ll join you directly,” Clarice nodded to the door and Kyla put her phone in her locker, refreshed her perfume, spat out her gum and went back to work.

“How is it working out for you Hun? Any concerns?” Clarice stroked Carey’s arm affectionately.

“It’s fine. Like Kyla said it aint rocket science,” Carey replied standing at her locker reaching for her handbag.

Kyla had told Carey to fix her makeup and refresh her perfume during the break because appearance was everything. Carey touched up her lipstick and sprayed herself liberally with perfume. She locked her locker and turned to face Clarice.

“And no one has clocked you?” Clarice frowned.

“To be honest I’ve been too busy to notice. In fact I’ve almost forgotten that I’m a man under these clothes and makeup,” Carey admitted.

“Oh, well that’s good but I’m sure you are Carey,” Clarice slipped a hand under Carey’s skirt and patted the front of her panties.

Carey blushed but it felt nice and her tucked penis twitched briefly.

“Just making sure your tuck is still tight,” Clarice winked at her and pushed Carey towards the door.

“I’ll see you after your shift,” Clarice said as she directed Carey back into the restaurant.

“Ok, you take the three back tables on your own and I’ll keep an eye on you. If you get flustered just give me a wave and I’ll come and help. You ready to fly solo?” Kyla asked, clearly impatient to rid herself of the rooky.

“Sure, let’s do this,” Carey replied but inside she was nervous.

Carey approached a table where four besuited men were sitting. She made sure that she got in close, smiled sweetly and chatted to them. She bent over the table to straighten the cutlery so that her blouse opened and her skirt rode up; a trick Kyla had taught her. One of the men audaciously slipped his hand under her skirt and copped a quick feel of her ass. Carey just smiled at him and took their order.

Next she attended to a man sitting in the back corner of the restaurant who she guessed was in his forties. He was sitting by himself tapping away at a laptop.

“Good afternoon sir, may I take your order?” Carey made sure that she sidled up close to the table.

“Just wait until I finish this sentence,” the man’s fingers tapped at the keyboard and then he finished with a flourish and looked up.

The man was not particularly striking but there was something about his face that was interesting and Carey thought he was uniquely handsome. This thought troubled Carey a little but she pushed it away and smiled sweetly at him. The man returned her smile but he didn’t immediately ogle her like most of the customers did. His eyes remained locked on hers.

“You're new,” he said with the confidence of someone who was a regular patron.

“Yes, I’m Carey,” she felt like her mouth was stuffed with cotton balls.

“Really?” the man looked pointedly at her name bar and Carey blushed at her stupidity.

“Of course you know that because it says so right here,” Carey pointed to her name bar, aware that the swell of her bosom was clearly visible through her open blouse.

“Well Carey welcome to the Perky Brew. I’m Lee and this is my table,” the man’s smile widened when Carey frowned.

“Of course I don’t own it but I always sit here in the corner. It’s quiet, the wifi is strong and I can write without being disturbed,” he elaborated.

“You’re a writer?” Carey felt stupid as soon as she said it.

“My Sunday brunch is two poached eggs on sourdough toast with linked sausage and a side of home fries and black coffee. Real coffee, none of that stuff the hipsters drink. No decaf, no syrups, no foam, no spices or any of that other wank; just a mug of the house roast,” Lee said glancing down at his laptop and editing something in the last sentence he had written.

“I like a man who knows what he wants,” Carey felt stupid as soon as she said it.

What was wrong with her? Why was she behaving like a dizzy schoolgirl around this man?

Lee glanced up and looked at Carey quizzically.

“Well you have my order,” he said dismissively.

Carey felt like a fool as she ripped the order off her pad and made her way to the counter.

With her back to him she couldn’t see that Lee was checking out her ass and legs as she walked away.

She served the four businessmen who once again ogled her and this time made some lewd comments about having a foursome with her and again she felt a hand slip under her skirt and fondle her ass. Anywhere else there would have been chaos as the waitress screamed blue murder, management stepped in and police intervention was considered. But here at the Perky Brew the pretty young waitresses were the customer’s playthings… so long as the customers tipped heavy. In any event Carey was a little flattered that the man found her attractive and relieved that her ruse was working. The four men ended up being very heavy tippers so the ends justified the means.

Returning to the counter Carey found Lee’s order was ready and she took it over to his table. Lee looked up when he heard the click-clack of her heels on the tile floor and watched her approach. There was something about this girl that pushed his buttons and it wasn’t just her good looks and coltish legs clad in those shimmery nylons. Lee was a leg man and preferred that his women wear hosiery although it wasn’t compulsory.

Carey wasn’t the prettiest girl in the shop nor did she have the best body. She was a little too tall, her breasts were small and her frame was a little lanky but those legs and that ass were to die for. But it wasn’t that. Like the rest of the girls she outwardly exuded sexuality but you could tell that she was new to it and a little uncomfortable in doing so. But it wasn’t that either. There was something unique about this young waitress that just intrigued him. Lee usually ignored the pretty little things flittering about the coffee shop and concentrated on his work but he kept looking up to find Carey and felt a little jealous when he saw one of the besuited men slip his hand under her skirt.

“Two poached eggs on sourdough toast with linked sausage and a side of home fries and black coffee without the wank,” Carey set down Lee’s order with a smile.

Lee looked at his food and beverage and nodded approvingly.

“Thank you Carey. By the way, I have one question for you as newcomer. Is being felt up in the job description or is it something you just let men do because you crave attention,” Lee said dryly and regretted saying it immediately.

“Enjoy your brunch,” Carey blushed but she was fuming and she turned on her heels and walked away.

Lee felt like an ass and knew that it was jealousy that his caused his outburst. He would apologise when Carey returned to bus his table and leave her a good tip.

But Carey didn’t return. Clarice switched Carey to the to-go line and after that she put Carey in another section, her intent being to get Carey used to working as many sections in the coffee shop as possible on her first day so that she could begin working unsupervised as soon as possible. Desmond White allowed his new waitresses one day to learn on the job. After that they became earners or were shown the door.

Carey finished her shift and sat down with Clarice to review her performance.

“How was your first day?” Clarice asked.

Clarice had brought them both low-fat lattes in to-go cups and taken Carey out back to the delivery yard away from the customers so she could vape. They sat on milk crates and sipped the coffee.

“Pretty good I think. As expected, the customers are a little crude and handsy but I had been told to expect and tolerate that,” Carey admitted.

“You weren’t clocked?” Clarice blew out a long stream of cranberry grape vapour.

“No in fact quite the opposite. I was propositioned a few times and felt up plenty. The only customer that really made me uneasy was that man Lee who sits in the back corner,” Carey admitted.

“Really? Lee is one of the few men who come in here who doesn’t proposition the girls, ogle them or feel them up. He’s usually a total gentleman,” Clarice looked perplexed.

“He’s kinda cute and gives off that rugged, older man vibe,” Carey admitted.

“You think he’d make a good Daddy?” Clarice teased.

Carey blushed. She had not told Clarice how new she was to all this and she was still coming to terms with her new-found femininity and attraction to certain men.

Clarice took another hit on her vape and handed Carey a sheet of paper.

“Here is your work schedule based on the college timetable you gave me. It’s hectic I know but still leaves you plenty of time to study but not for much else. When you receive your first wage packet you won’t complain. Desmond explained that you will be paid cash right?” Clarice gave Carey a knowing look and Carey nodded.

“He’ll want you in his office now and then to pay for the privilege, you know what I mean?” Clarice touched Carey on the forearm.

“Stick to blowjobs or better yet fetch him off with your hands. Do not let him find out that you are Trans. Of course he legally can’t discriminate against transgender women but as you’ve already witnessed, Desmond White doesn’t play by the rules,” Clarice said sternly.

“You can keep the tits. See you tomorrow,” Clarice leaned in and kissed Carey’s cheek

As Carey walked back to the campus accommodation she thought about what Clarice had said. She had referred to Carey as ‘Trans’ a few times but Carey wasn’t transgender. She was just a crossdresser, a transvestite, a female impersonator whose motive for doing so was to expose the gender biased work practices in Balwyn and expose the awful misogynistic and sexual exploitation of the waitresses working at the Perky Brew.

When she got to her dorm Carey kicked off her heels and rubbed her feet. They ached from being on them all day and she knew that should remove her makeup and get out of her femme clothes but she didn’t want to. She felt comfortable in them. Instead she fired up her computer and began writing her exposé.

She lost track of time and when she came out of her reverie it was late and dark outside. She stripped and used moisturised facial wipes to remove her makeup and nailpolish remover on her fingernails and then something happened. There was some kind of psychic shift and Carey the girl became Carey the boy.

He looked at his naked body in the mirror. A handsome nineteen-year-old boy with a slim body, long legs and a bubble-butt looked back at him. He’d once been called a twink by a gay acquaintance and now he could see why. There were red patches on his chest where he’d sweated under the breastforms and skerricks of eyeliner and mascara around his eyes.

Carey put on a robe, took his toiletries and towel and headed down to the ablutions, feeling a pang of guilt as he walked past Vickie’s room. There was light under the door and he could hear Billie Eilish’s latest release being played a little too loudly for this time of night. He wondered if he should knock. They usually had catch-up sex when either of them had been away but he decided not to. He still reeked of perfume and wasn’t sure he’d got all the makeup off his face and Vickie was very observant.

He took his time in the shower and recalled the day’s bizarre events. He should probably stop working at the coffee shop right now. He didn’t know long he could carry off the ruse before he slipped up and was exposed. In hindsight maybe the purchases had been extravagant. Maybe he should ditch the clothes he’d worn and the makeup and try to return the rest of the clothing. Surely he had enough evidence to write his paper?

He’d think on it.

Carey didn’t wear the lace chemise to bed. He’d spent all day pretending to be a girl. He needed to get away from his alter-ego and start thinking like a man again. Carey tried thinking about the pretty young waitresses at the Perky Brew and about fucking Vickie in her cheerleader's costume but his mind kept flitting back to when Clarice Starr had slipped her hand under Carey Davenport’s skirt supposedly to check her tuck. Then he thought about his female alter ego’s fascination with Lee the writer. He thought about her in the third person but the bulge in his underpants betrayed his disposition. And of course he thought about Carey sucking Desmond White’s cock.

He tried to drive all thoughts out of his mind because he had a busy day tomorrow and he finally drifted off to sleep.

The next morning Carey had lectures to attend but he had the afternoon and evening shift at the Perky Brew and he was debating whether or not to turn up. It was unlikely Desmond or Clarice would come looking for him and anyway the mobile phone number and address he had used on his application had both been bogus.

He skipped lunch and went back to his dorm room and opened his wardrobe having finally decided that he would purge but as soon as he saw the skirts and blouses hanging up in the wardrobe his determination began to wane. Carey’s perfume lingered on the skirt and blouse she had worn the day before. He opened the drawer full of lingerie and hosiery and ran his fingertips across the delicate garments, delighting in the feel of them. Carey’s mind began to drift.

Carey found herself in front of the mirror, her face transformed by makeup. She was wearing bra, panties and pantyhose and fussing with her hair when she came out of her reverie and realised that she hadn’t consciously made the decision to transform; it had somehow just happened but she had no time to evaluate how because she would be late for her shift. She slipped into a black A-line miniskirt, pink satin blouse and put on her heels. Now she had shoes that fit she would not need to wear trainers to work. She accessorised, put the essentials in her purse and left the dorm.

Monday afternoon wasn’t as busy as the day before had been and Carey was given her own section to service. She spotted Lee in the back corner busily typing away on his laptop and she stayed clear of him and tended to the other customers in her section. She wasn’t harassed as much as she had been on Sunday and the day started out quite mundane.

But late in the afternoon the place began to fill with the usual crowd of business types, salesmen and tradesmen. The waitresses began their usual tikanga of flirting with the customers, flicking their skirts, blouses opened, bending over to ensure their assets were on display, chatting pithily, sometimes lewdly with the men, sometimes allowing themselves to be felt-up and of course, raking in the tips.

The four besuited men she had served yesterday were back and Clarice seated them in Carey’s section. Carey took a deep breath and went over to take their orders. The cheeky banter began immediately.

“Hey guys, it’s the new girl, aren’t we lucky,” one the men smiled wickedly at the others.

“I’m Carey and I’ll be your waitress gentlemen,” Carey flashed her best smile.

As she’d been coached, she stood as close to the table as possible and ensured that her blouse opened as she bent down to give them each a menu. She was confident that her prosthetic breasts looked realistic through her ivory satin and lace blouse.

“Carey hasn’t got much in the way of tits has she guys?” one of them commented.

“No but they're perky and she had a great ass and long legs,” another observed.

At any other establishment the men would have been shown the door and banned but this was the Perky Brew and the clientele paid exorbitant prices for their food and beverages and tipped heavily for the privilege of behaving like boors and treating the girls like chattels.

“Honey can you come over here and explain this dish to me?” the man who had felt her up yesterday asked.

He was sitting with his back to the wall, his three comrades partially blocking the view from the other patrons and Carey sidled up to him standing as close as she could. She knew that the man was going to take liberties with her and despite her trepidation, part of her welcomed it. It was somehow gratifying, knowing that she was so pretty and feminine that these idiots couldn’t tell that she wasn’t really a girl. But there was something else. She found it somehow carnally felicitous when she was spoken to and touched inappropriately.

“Yes sir, what can I help you with,” she bent down so that her face was close to his as they both studied the menu.

She could smell the booze on his breath and his expensive cologne and she was sure that he could smell her perfume. He was looking at her face not at the menu and when his hand touched her leg she sensed his breathing quicken.

“Does this come with fries or do I need to order them as a side,” he whispered, his finger pointing vaguely at the sandwich section of the menu.

Carey shuddered as the man began to stroke her leg. The feel of his manly fingers rubbing her flesh through her silky hose was delightfully decadent, especially knowing that the other three men were watching. She could feel their eyes on her body and see the excitement on their faces as the man slid his hand under her skirt.

“All the sandwiches come with fries and you have the option of two sides,” Carey explained, her voice barely a whisper.

She felt the man’s hand cup her buttock and begin to softly squeeze it. Yesterday she had let him cop a quick feel but now she was letting him knead her ass. She realised she was being complicit and any rebuke would be churlish.

“You know you are stunning Carey,” the man whispered as his hand slid from one buttock to the other.

“You know I’m young enough to be your daughter,” Carey whispered, rebuking him delicately.

“Jesus Jake, get your hand off her ass,” one his compatriots whispered nervously.

The restaurant was crowded but where the man was sitting facing out into the restaurant with his friends obstructing everyone else’s view, he was confident that no one was watching and he continued to stroke Carey’s bottom.

Carey had to admit that the sensation of Jake’s hand sliding her satin panties over her silky pantyhose was intensely arousing and she hoped that her tuck stayed in place as her cock began to bloat.

“Bullshit. No one can see and I think she likes it,” Jake grinned.

“Do you like it Carey?” Jake asked.

“See, the sides are listed here,” Carey continued, pointing at the menu, ignoring the question.

“I’ve got fifty bucks says Carey is wearing white panties,” Jake suddenly dug his fingers into her soft, yielding flesh and Carey winced but said nothing.

“Come on you guys. Lay out fifty each and let’s see if I’m right,” Jake chuckled.

“Are we really doing this?” one of them replied but he reached inside his coat for his wallet.

Carey saw the money pooled in the middle of the table and blanched.

“Come on Carey. That’s all yours if you prove me right,” Jake squeezed her bottom again.

Carey knew that what she was complicit. She should have taken Jake’s hand from under her skirt when he first copped a feel but instead she had stood steadfastly beside him while he stroked her legs and fondled her ass. The time for castigation had long past.

“I keep the money and you guys still have to tip,” Carey couldn’t believe the words were coming out of her mouth.

She glanced around the coffee shop and saw that no one was paying any particular attention to them. She was just another pretty waitress flirting with customers while she explained the menu, soliciting a bigger tip.

Carey took a deep breath and took the hem of her skirt in her fingers. She heard the men’s breathing become laboured as she slowly slid the hem of her skirt up her legs. Her coltish thighs, clad in the shimmery pantyhose were a delight to behold and she just knew that the men were becoming erect. She stopped with the hem resting just below her mons and smiled at the men salaciously. They all had their eyes locked on her legs. Two of them were sweating and all of them were breathing heavily, the beer and bourbon fumes clouding the air.

Carey lifted her skirt the final few inches to reveal her ivory satin panties with a pink bow in front and the men all gasped. She allowed them a few seconds to take in the vista but when Jake reached for the perfect Vee between her legs she dropped her skirt.

“Thank you gentlemen. So that’s Reuben’s all round with a side of slaw and onion rings, and black coffee. I’ll be right back with your orders,” Carey snatched the cash off the table and walked away leaving the men stunned and silent.

She could hardly believe what she had just done and she too was breathing heavily and was a little unsteady on her feet. She was uncomfortably tumescent, her cock pressed against her perineum threatening to break free of its satin and nylon trap.

She wrote down the order and dropped it at the kitchen window and hurried to the break room. She locked the cash in her locker and stood there quivering, flushed with anxiety and sexual energy. Where had this brazenness come from? Had Carey found another side to her personality? Was she indeed a slut?

She had no time to ponder this dilemma and she went back out to work her section, aware that the four businessmen were watching her every move.

When she delivered the order to their table Jake beckoned her over.

“I’ll give you five hundred dollars if you meet me outside in the parking lot after your shift,” he pleaded and Carey could see the desperation in his eyes.

“No thank you sir. Enjoy your meal gentlemen,” Carey smiled sweetly and calmly walked away but her heart was racing.

“Time for your break Carey; Kyla will take over your section,” Clarice caught Carey on her way to deliver an order to the barista.

Clarice led Carey out into the delivery yard and took her vape out of her purse.

“You're playing a dangerous game,” Clarice blew a plume of vapour into the air.

“Both you and Desmond have made it perfectly clear that we are to flirt with the customers and let them take a few liberties,” Carey blushed but she was also a little pissed.

“Oh, I've nothing but admiration for your performance but you have a special secret that you need to keep,” Clarice smiled conspiratorially.

“Those rubes had no idea. That man Jake actually offered me five hundred bucks to meet him after work,” Carey countered.

“Ok. I know some of the girls see customers outside of work. A girl’s gotta do what girl’s gotta do to make ends meet but you don’t have that option. Are you living full-time as a girl?” Clarice asked.

Carey was caught unaware by the question but she scrambled.

“I’m still coming to terms with my gender and sexuality issues. I’m not yet fully committed to transitioning,” she lied.

“So I’m guessing you are enrolled at the college as a male and living as female outside of your classes. I’m not here to take your inventory Carey. I watched my sister battle her dysphoria. Just make sure that you are not outed until you are ready to be. This is not really a safe place to work for someone like you,” Clarice patted Carey’s shoulder.

“Are you firing me? I figure that if I can work here and pass as a woman then it will give me the confidence I need to progress,” Carey told a half-truth.

“I’m not going to fire you honey, just be careful, that's all I'm saying,” Clarice put her vape back in her purse.

“Now go and grab a coffee, take your break and fix your makeup,” Clarice opened the back door to the coffee shop.

Then it struck Carey.

“How do you know what I just did?” Carey asked.

“I know everything Carey,” Clarice smiled sweetly.

Carey looked confused.

“We have cameras honey. The hostess station and Desmond’s office have a live feed. If Desmond has seen what you just did, don’t be surprised if he demands your presence in his office a little sooner than you expected,” Clarice’s smile turned into a grin and Carey swallowed as she went back inside.

“Hey, those guys tipped twenty bucks each. Did you give one of them a handjob?” Kyla jested as she handed Carey’s section back to her.

Carey worked her shift and besides the leering, the inappropriate comments and the odd improper fondle here and there it was business as usual. She was making good tips and garnering more evidence for her paper. She was thinking that if she saw out the week it would provide more credibility for her exposé when she submitted it. Besides, she deserved her share of the tips when they were finally divvied up didn’t she?

She was pondering if she was just justifying to herself an excuse to keep presenting herself as female, enjoying wearing the clothes and makeup, titillating men, relishing the almost constant state of arousal and excitement. Then she saw Lee raise his hand and wave at her.

Carey sashayed over to his table to take his order and as she approached she looked at him critically. There was something about his face that she found fascinating. He had sandy hair that was stylishly tousled, watery blue eyes, sensuous lips and was unconventionally handsome in that his cheekbones were prominent, his face long, his jaw narrow and the bridge of his nose was broad. He reminded her of the British actor Benedict Cumberbatch. He was wearing tan chinos and a faded chambray shirt with the cuffs rolled up. A khaki sports coat hung over the back of his chair.

Carey was deliberately cool with him, remembering how he had chided her yesterday about allowing herself to be felt up. For some reason she hoped that he had not witnessed her performance when she allowed Jake to feel her up and her skirt lifting display for Jake and his buddies.

“Yes sir, can I take your order?” she asked impassively.

“Before you do I’d like to apologise for what I said to you yesterday. It was inappropriate and churlish,” he said, his eyes locked on hers.

Carey couldn’t help but smile.

“It’s ok sir. You come here almost every day I’m told, so you know that the clientele take liberties that would not be condoned elsewhere,” she replied.

“Yes but your business is your business. I know that you girls work hard to make a buck to help support your way through college. And please, call me Lee,” he gave her a smile that made her heart flutter.

Carey was confused. Why was she fascinated by this older man? She was supposed to be a man masquerading as a woman garnering insight and information to support a written assignment, not some bimbo in a short skirt feeling weak-kneed and smitten.

“Ok Lee, what can I get you?” Carey asked giving him a brilliant smile.

“Just coffee please. You know how I like it,” he returned her smile.

Carey wrote down the order and turned away and made her way to the barista. She did not know that Lee was following her with his eyes.

“You dummy! You should have engaged with her more,” Lee whispered to himself.

Lee still couldn’t understand what so fascinated him about Carey. She was really no different to the other girls who flittered around the coffee shop in their short skirts and heels with their tits out. He found them rather banal and ditzy, flirting with the clientele to pump up their tips. He suspected that some of the girls met up with customers outside of work because he’d seen them being driven away at quitting time.

There was just something about this tall, long-legged, small breasted young woman that captured his imagination. There was no doubt that she was pretty… but all the waitresses were pretty and he’d never once come onto them. He watched the way she walked, not quite as confident as the others, like a young gazelle finding her feet. Her pert bottom in the little A-line skirt drew his attention and those long nylon-sheathed pins gave him a hardon that was quite uncomfortable.

Carey returned with his coffee.

“Black house roast with no hipster wank,” Carey smiled at him as she put the coffee down on the table.

“May I ask what perfume you are wearing?” Lee felt like a chump as soon as he said it.

He was behaving just like all the other older men flirting with the young waitresses, offering insipid pickup lines.

“It’s a knock off of Dior Poison which is my favourite perfume but I can’t afford the real thing. It’s a generic brand I found at Walmart,” Carey admitted.

Carey did indeed love the fragrance of Dior Poison and had purchased a small bottle at great expense for Vickie who had told him that it was passé and old fashioned. She hardly ever wore it and Carey wished that he’d stolen it from her room when he’d rifled through her things but she didn’t want Vickie to find it missing.

“Well I find it delightful,” Lee stirred his coffee unnecessarily because he took it black without sugar.

“Anything else?” Carey was keen to move on because she still felt a little resentful about what Lee had said to her yesterday and she was uncomfortable with her attraction to him.

Lee tried desperately to think of a reason to keep Carey engaged. He just wanted her near him but he could think of nothing. Lee shook his head and Carey moved away to serve other customers.

At the end of her shift Carey collected her purse from her locker. She smiled at the thought of the illicit cash inside it. She made her way to the front door and was about to open it when she saw Jake parked at the curb right outside. The engine of his BMW coupe was running and he was staring intently at the door to the Perky Brew. Carey turned to the hostess station but Clarice had left and been replaced by a stern-faced young woman who she didn’t know.

She considered going over to the new hostess and explaining her dilemma but what would she say? That she’d let the man repeatedly fondle her ass and today she had shown him and his friends her undergarments in exchange for cash and now he was waiting outside for her?

Then she looked up and saw that Lee was looking her way and she went over to his table. He had packed up his laptop and put it in a battered leather tote. He was putting on his jacket and was getting ready to leave. He seemed delighted to see Carey and she pressed her advantage.

“Can I ask you a huge favour?” she asked Lee.

He looked at her quizzically and she continued.

“There is a guy outside. He’s a real jerk and he propositioned me and… well I might have done something to encourage him… but anyway I don’t want to have to engage with him so I was wondering if you would escort me outside?” Carey gave him what she hoped was a doe-eyed pleading look.

“Of course I can,” Lee flung his satchel over his shoulder and indicated that she should lead the way.

“There is a back entrance through the delivery yard but it’s locked and alarmed and staff are forbidden to use it,” Carey began to ramble.

“Is Desmond White afraid that his harem is going to steal the coffee beans or something,” Lee’s joke fell flat and Carey led the way to the door with Lee’s eyes locked firmly on her trim ass.

The new hostess gave Carey a knowing look and Carey shook her head but the hostess just grinned at her thinking that Carey had picked up a generous older man like so many of the other waitresses did. Carey didn’t feel like explaining and she just brushed past the hostess and stepped outside.

The passenger door to Jake’s two-door ‘penis-extension’ sports car opened and he beckoned her. Carey ignored him and sidled up to Lee.

“Fucking slut!” Jake called out, slammed the door and drove off in a haze of exhaust and screeching tires.

“What was that about?” Lee asked.

“He’s the jerk who propositioned me,” Carey explained.

There was something comforting about walking close beside Lee that Carey couldn’t explain but it was pleasant and she felt a warm glow in her belly.

“Maybe I better do this so that if he returns he’ll know to back off,” Lee slipped his arm around Carey’s waist.

Carey stood 5'11" in heels and Lee was only 5'7" and quite a bit older than Carey. They might have looked like a father and daughter to passers-by but then Carey put her head on Lee’s shoulder.

“Just so he thinks I’m your girl if he returns,” Carey whispered in Lee’s ear.

The whisper of her breath in his hair, the closeness of her trim body and the scent of her perfume excited Lee. He knew that he shouldn’t be attracted to this teenage girl but he couldn’t help himself. He felt an uncomfortable stiffness in his groin. Her words echoed through his mind: ‘I’m your girl’.

Lee came to a halt next to a 1970 Ford Mustang. It was a 302 V8 finished in deep impact blue with chrome wheels and had been lovingly restored.

“This is me,” Lee said.

Carey didn’t want Lee to take his arm from around her and she leaned into him a little.

“Thank you Lee,” Carey whispered and kissed his cheek softly.

Her lips felt like butterflies caressing his face and Lee felt both elated and foolish. She probably thought he was an old man… a cranky old man at that because he had been so caustic with her the day before.

“Can I give you a ride?” the words slipped out of Lee’s mouth before he could stop them.

“I’d be delighted,” Carey replied but she too was bewildered as to why she would say yes.

Lee opened the door for her and he tried not to look at her thighs as her short skirt rode up when she folded herself into the seat. He caught a glimpse of her ivory satin panties that took his breath away. Carey knew that she should pull down the hem of her skirt and demonstrate some decorum but she left it riding high on her thighs.

‘What am I thinking?’ Carey thought to herself as Lee tossed his tote in the back and climbed in the driver’s seat.

“This is great car,” she said, as Lee fired up the engine.

“I like it,” Lee replied.

Both of them felt a little foolish and Carey was confused. What was she doing in the car of an older man whom she had only met the day before? What was she doing with any man for that matter? She wasn’t a real woman despite how she felt and thought about herself. This could only end badly but she smiled at Jake and when he smiled back at her the warmth in her belly began to spread.

“You wanna go for a drive?” Lee blushed when he asked.

“It’s night time Lee,” Carey answered.

“Well yes,” Lee relied awkwardly.

Lee felt like Humbert to Carey’s Lolita. He knew that he was steering into dangerous waters with this young college girl but she fascinated him for some reason that he couldn’t quite put his finger on and he hadn't been able to get her out his thoughts after he had first met her. Lee hung around the Perky Brew like it was his second home but he had gone there today specifically hoping that Carey might be working and hoped that he might be able to engage with her. Now here she was sitting in his car and he couldn’t believe it.

Carey sensed Lee’s unease. She felt it too. She had begun to increasingly recall the memory of making out with the young, sexuality fluid men at the rave she had attended during her ‘Goth period’ when Carey’s girlfriends had crossdressed him. He was eighteen at the time and troubled about his gender and sexuality and after the incident Carey had repressed the memories and given up the Goth lifestyle, which to be fair, he had only adopted to score with the Goth girls.

But the memories had resurfaced as soon as Carey started to crossdress. Carey recalled the tentative kisses that had somehow become passionate, the bungling and fumbling when one of the young men had slipped his hand under her skirt and stroked her cock through her panties. The flustered impatience as she had unzipped him and returned the favour, her black nailpolished fingers sliding up and down his delicate flesh until her hand was sticky with his warm glutinous emissions. The shame and self-recriminations that followed that had forced the memories deep into her subconscious.

Then there was the incident in Desmond White’s office, where despite his toad-like countenance, she had submitted to his kisses and caresses and degraded herself by dropping to her knees and taking him in her mouth. What was happening to her?

“Well Balwyn is pretty at night,” Carey whispered, shaking away the memories.

The words slipped out of her mouth before she knew that she was saying them.

They drove in silence for a while, Lee trying to concentrate on the road instead of looking down at Carey’s long coltish legs clad in shimmery nylons. His head was spinning and all he could think about was the closeness of this gorgeous teenage girl. Her scent seemed to have inundated the air in the car, her warmth seemed to emanate from her body and he could still feel the soft caress of her hair on his face and the lingering sweetness of her lips on his cheek. He was rock hard in his chinos and his cock was throbbing like a sock full of grasshoppers.

“Tell me about yourself Lee,” Carey turned to face him and was once again struck by his unusual handsomeness.

“What is there to say? I’m a jack of all trades, master of none. I’m a photographer, an audio engineer and a person who spins narratives and fables of fantasy from the cloth of imagination and language. I’m a creator of mythology and a chronicler of the unreal,” Lee smiled and Carey returned the smile.

“I guessed that you were a writer,” Carey patted Lee’s thigh comfortingly.

“I’m writing a short dissertation for one my college courses. Maybe I should get you to look at it when I’ve finished the first draft?” Carey patted his thigh again and Lee appreciated the intimacy.

“Go on,” Lee could listen to Carey talk for ever.

Her voice was sultry and musical, deeper than one would expect for a girl her age but it was also very sexy.

Carey suddenly had an epiphany. She would come clean to Lee. He would more than likely be repulsed by her but he might also find her intriguing. Lee could be a valuable asset that she could use to help write her exposé.

“I have to tell you something Lee. Do you think you can pull over?” Carey asked.

They were driving along a country road on the outskirts of Balwyn, the lights of the town twinkling below them as they crested the top of a hill. Lee pulled into a turnout and parked facing the vista of Balwyn spread out below them. When he killed the headlights they were alone in the dark. The reflected city lights were mirrored in Carey’s emerald green eyes which seemed to sparkle in the dark. Her hand still rested lightly on Lee’s thigh.

“I’m not really a girl Lee. I know that I look like a girl and I certainly feel like a girl, at least some of the time anyway. Like now for instance,” Carey whispered in the dark.

Lee’s brow furrowed.

“I don’t understand Carey. That is I think I do understand because there is something about you that has been troubling… no that’s not the right word… intriguing me. I sensed you were different somehow… that you were special,” Lee admitted.

“Look, I know you must think I’m a freak or a pervert or a charlatan or whatever but…” Carey never got to finish her sentence.

Lee leaned in and kissed her.

The kiss was soft and comforting and so different to the awkward teeth-clattering, tongue-wriggling sloppy kisses she had exchanged with the Goth boys and nothing like the almost rapey cossetting she had endured during Desmond White’s advances.

This was different. Carey was kissing a man that she yearned to kiss. A man who had entered her dreams. A man she thought would be repulsed by her but was now kissing her tenderly without the wantonness and lechery she had felt when she had kissed other men.

She sensed that this was right, despite the feelings deep inside her that it was wrong.

The kiss lingered and Lee was close to breaking away from her, sensing that he had done something wrong. Her lips were soft and yielding, her perfume intoxicating, her beauty irresistible but she was young, and her gender was indeterminate. Carey had told him she felt like a girl but she wasn’t really was she? But even with this newfound knowledge Lee still desired her. In fact her unique exoticness made him want her even more. He was far from the shore and unsure of himself.

But then Carey’s lips opened slightly and he felt the tip of her tongue slip into his mouth and the bulge in his pants throbbed more intensely. He reached for her clumsily, the console between them getting in the way. Carey put her arms around Lee and allowed herself to be pulled into his arms.

“I’m not sure if what we are doing is right. I’m so much older than you and I’m not sure that you are thinking straight or that you are sure of yourself. I don’t want you doing something you might regret later,” Lee broke the kiss and his speech was breathless.

Carey sensed Lee’s reticence. She felt it herself. But she also knew that if she didn’t explore the feelings she had for this man she might regret it for the rest of her life.

“Climb in the back seat with me and let’s see what happens. If either of us begin to feel uncomfortable or discomfited we can stop. You can drop me off at my dorm and I’ll just be that girl in the coffee shop that you found interesting but turned out to be disappointing,” Carey searched Lee’s eyes for any hesitancy or reluctance.

Carey was incredulous that she was being so brazen and bold. She wasn't sure that she was thinking straight but she knew what she wanted right now in this very minute and that’s all that mattered.

Without any further conversation Carey clamoured into the back seat. The exercise was cumbersome and undignified but Lee didn’t mind at all because he got a good look up her skirt and what he saw delighted and excited him. Those ivory satin panties clung to the perfect globes of her ass and those long legs sheathed in the delicate, diaphanous pantyhose seemed to go on forever.

Lee joined her in the back seat and pulled her to him and kissed her. This time there was nothing nuanced or subtle about the kiss. It was raw and ribald, their tongue’s entwined and their lips locked together as they pawed at each other.

Carey reclined on the back seat as best she could; her long frame did not permit her to lie fully prone so she wrapped her legs around Lee’s. Lee unbuttoned her blouse and when he reached inside Carey put her hand on his wrist to stop him progressing further.

“They're not real,” she whispered, feeling ashamed.

“I don’t care Carey. I want to feel the real you,” Lee looked deeply into her eyes in the dark as his fingers slipped into her bra.

He gently extracted the breastforms and put them aside and his fingers stroked her little buds, her nipples hardening to his touch. Carey gasped as Lee stroked her meagre bosom and caressed her small but tactile nipples.

Little ringlets of pleasure radiated from the sensitive nubbins and Carey felt her cock become harder. It was uncomfortable, trapped along her perineum inside her panties and hose.

But not for long.

Lee kissed her passionately and his hands slid down her body and slipped under her skirt. He stroked her silken-clad legs and he shuddered as he kissed her. His fingers had finally found those long coltish legs that he had dreamed of touching and he wasn’t disappointed. Carey began to quiver and sigh as Lee took his time exploring her legs, his hand sliding all the way down to her knees and then slowly crawled up her thighs. He stroked the crease where her legs joined her torso and Carey moaned.

This was like a dream. She had never felt so aroused, so wanted, so appreciated, so desired. She could feel his hard cock pressing against her. She felt the heat of it. She felt it quiver. She didn’t know if it was her imagination or if it was real but it released a wantonness in her that could not be denied.

When Lee cupped her buttocks and gently kneaded them she thought she might prematurely ejaculate. Her cock was fully engorged and begging or release. She reached for Lee’s zipper and the sound of it opening was almost deafening in the silence of the car. They didn’t need background music; they were making their own.

Their sighs, their moans, their hisses and Carey’s giggles were a symphony of lust and rapture. Carey was not a teenage boy dressed in ladies clothing, she was Lolita and Lee was Humbert. That was how they both felt, even as Lee slipped his hand inside her panties and freed her cock from between her legs. It tented her pantyhose and Lee stroked the engorged member through the diaphanous fabric, feeling beads of pre-ejaculate dampen the nylon.

Carey had Lee’s bloated rod in her hands and she was softly caressing it. Feeling the power of his shaft cloaked in the delicate smooth flesh, the little veins running along the sides of it pulsing in her fingers, the spongy mass of his glans, the dribbles of precum leaking from the eye.

Their kisses became more impassioned and Carey pushed Lee’s pants down and he struggled to climb on top of her with his chinos tangled around his ankles so Carey opened her legs wide to make it easier. Lee pushed up her skirt and pressed his cock against hers and began to rut. The feel of Lee’s cock pressing against hers through the layers of satin and nylon was like nothing she had ever experienced.

Lee gasped as he felt his cock press against Carey’s panty-shrouded member. He didn’t feel like he was doing anything perverted. He didn’t have an inclination for men or boys. Carey was a young beautiful woman. She smelled like a woman, she felt like a woman, she tasted like a woman… she was a woman. A beautiful young woman who just happened to present exotically different and he loved her for it.

Carey lifted her legs and wrapped them around Lee’s hairy, muscled thighs and pulled him close. She clasped her arms around his neck and kissed him deeply. The feel of his cock rubbing against hers was incredibly arousing. Lee groaned as his cock slid up and down the wispy, ethereal material of her panties. He felt her steely phallus inside the gossamer sheath quiver and a freshet of pre-ejaculate oozed from her rod. Her panties were sodden with their juices.

Carey rubbed her legs along Lee’s thighs and lifted her buttocks off the seat to press her cock harder against Lee’s shaft as she felt a momentous orgasm begin to erupt. She nipped his lips, then crushed her mouth against his and quivered as her body convulsed in an orgasmic explosion of passion and pleasure.

Lee felt Carey shudder in his arms as her cock began to convulse and then the creamy, warmth of her spend soaking through her panties as she climaxed. Lee came right along with her, grinding his quivering cock against hers as he ejaculated. Their semen comingled and became a pool of slippery, musky of milt. The stench of it filled the car and drove them both into a frenzied paroxysm of frottage as they clung to each other, kissing, groping and gasping. Carey slipped her hands inside Lee’s shirt and dragged her red-pantied nails cruelly, passionately and lovingly down his back.

Lee lay on top of Carey as their convulsions slowly subsided and their kisses became less frenzied and more tender. Lee stroked Carey’s face and looked into her eyes adoringly. There was no shame or regret. Their raw passion had subsided and become something the neither of them had words for and were both too scared to articulate.

They lay like that. Like any other two lovers who had slipped into the back seat of their car to grab a moment of illicit pleasure.

“What have we done?” Lee finally whispered.

“We’ve done nothing wrong Lee. Do you regret it?” Carey sensed the hesitancy in Lee’s voice.

He looked down at her lovingly and kissed the side of her mouth tenderly.

“Regret it? It was the most amazing experience I’ve ever had,” Lee kissed her again full on the lips.

“What about you? Do you regret it?” Lee searched Carey’s eyes looking for remorse.

“Lee, it was incredible. I’ve never felt anything like it either. If I didn’t have classes tomorrow I’d toss your keys out the window so we would have to stay in here until dawn,” Carey giggled.

She had never felt more like a young woman than she did now. This was no charade. This was something else that she would need to ruminate over later but right now she wanted to enjoy the pleasure, contentment and satisfaction that she felt lying under this handsome older man.

So they lay like that until the practicalities of the situation dictated otherwise. Their legs began to cramp, their semen cooled and a chill filled the air that not even the warmth of their bodies could counter. It had been awkward climbing into the cramped back seat of the car but the acrobatics as they disentangled themselves and cleaned themselves up and dressed was twice as embarrassing and uncomfortable and they both felt a little sheepishness as they did so.

Lee gave Carey a handkerchief so she could soak up the semen as best she could. She patted her panties until they were dry enough not to stain her skirt then she wriggled her ass in the seat as she pulled the hem down. She slipped the breastforms back into her brassiere and buttoned her blouse and only then turned on the interior light so she could fix her makeup. When she was finished she looked presentable, even if her panties felt a little squishy.

Lee had managed to pull up his pants and zip his fly without the same theatrics and he’d climbed back in the driver’s seat to give Carey some privacy while she tucked.

Carey checked her phone and found six missed calls from Vickie and as many texts. She slipped her phone back in her purse thanking the powers that be that she had switched it to silent when she started her shift at the Perky Brew and hadn't bothered switching it back when she took it from her locker. She couldn’t deal with Vickie right now.

Lee helped her into the front passenger seat and they drove back to Balwyn college in awkward silence, both of them with so much to say to each other but neither of them knowing how to say it.

Carey kissed Lee on the lips before she climbed out the car.

“See you tomorrow?” Carey asked.

It was a question not a statement.

They had both had time to cool off and neither of them was sure how the other felt about what they had done.

“You betcha,” Lee replied.

Feeling his response was a little trite, Lee continued.

“Are you ok Carey?” he asked, his concern genuine.

“Oh honey, I’ve never felt better,” Carey leaned in through the door and kissed Lee on the cheek.

She felt like she was floating on air as she made her way to her dorm, resisting the urge to skip.

Carey slept in the red babydoll satin and lace chemise nightgown that night still in full makeup and wearing her cum-soaked panties and pantyhose. She wanted to feel Lee’s essence on her body and the musky scent of him while she slept and dreamed of him.

Her dreams were ribald and during the evening she had a nocturnal emission which further soaked her panties. In the dream Lee was making love to her and she was clinging to him, moaning like a slattern.

The next morning she had to deal with the practicalities of being a closet crossdresser. She removed her makeup and nailpolish and changed into boy pyjamas and put on shower shoes to go down to the bathroom. During this transformation Carey’s conscience shifted and he was no longer Carey the young woman, he became Carey the young man.

While he used the ablutions Carey considered what had happened yesterday. His alter ego was becoming quite the slut and she was also developing deep feelings for Lee. This was not the plan when he ‘created’ Carey the waitress. She was supposed to be a tool he used to garner information to substantiate his thesis. She had been invented as a means to spite the advantaged, entitled, overly favoured, pretty little hussies who worked at the Perky Brew, not to become one herself.

Also he had Vickie to contend with.

Her texts were becoming vitriolic. He was avoiding Vickie because Vickie had texted him that she had heard rumours that Carey had a new girl in his life. Carey smiled ironically at that but he couldn’t keep avoiding her.

He attended his classes and blew off a seminar that held little interest for him and he went back to the dorm and worked on his paper. He would leave out the part about Carey and Lee’s backseat shenanigans but leave Lee in the dissertation under a pseudonym as proof that even a seasoned mature professional man could be hoodwinked into believing that a young man could pass as a young woman.

When he transformed into Carey the girl, the shift in Carey’s psyche from male to female was almost seamless and instantaneous. Carey was not only very comfortable thinking and presenting femme, she was beginning to prefer it and as she walked to the Perky Brew she contemplated the significance of that.

Carey was not working the section where Lee had set up his little nest but she was keen to talk to him. She wasn’t embarrassed about what had happened in the back seat of Lee’s Mustang but she was keen to pick Lee’s brain. She needed to know exactly what was going on between them. Did they have a relationship or was Carey going to be his dirty little secret, his occasional tranny fling?

The problem was that the Perky Brew was doing a roaring trade and between taking orders, delivering food and beverages, bussing tables and engaging in playful banter and slapping away roving hands, she just couldn’t get away from her section.

Lee saw that Carey was too busy to come over and chat. He would need to get inventive if he wanted to converse with her.

When Carey saw that Lee was packing up to leave she went over to his table and Lee looked up at her and smiled and slipped her a hand-written note.

‘Bring your dissertation to my place tonight and I’ll review it for you. Maybe we can get cosy after,’ the message read.

“What are we high schoolers passing notes in class now?” Carey said to herself as read Lee’s missive.

Lee had written his address at the bottom of the note and Carey’s heart was thumping. She could guess what Lee meant by getting cosy and her mind was in turmoil at the thought of it. So far her sex life had consisted of fellating Desmond White and engaging in frottage with Lee, did she want to go ‘all the way’?

Carey could think of nothing else during her shift. Part of her was terrified and part of her was fascinated and enthralled with the idea. She stopped at a couple of specialty stores on the way back to her dorm. She had made up her mind.

Carey opened the box containing the anal douche and read the instructions. She realised that as unpleasant as it seemed, it was essential that she use the device if things were going to progress the way she thought they were. She’d been on several online porn sites and the crossdressers in the videos she had watched certainly seemed to enjoy being fucked and she was determined to find out if it was as pleasant as it looked.

She took the device and a tube of lubricant down to the ablutions and did what was necessary then she returned to her room, fixed her makeup, dressed and put the other purchases she had made into a carrybag and left the dorm. She used Google Maps to find Lee’s place which turned out to be a ground floor studio apartment. His highly recognisable vehicle was parked outside. She parked in the space beside it, grabbed her purse and the carry bag and walked up to the door and knocked.

Lee greeted her with a huge smile and he looked her over appreciatively. They kissed and before Lee could take any liberties Carey slipped out of his grasp. She took a printed copy of her draft dissertation out of her carry bag and pushed into Lee’s hands.

“Is that the bedroom through there?” she pointed to a short hallway.

Lee just nodded, feeling a little perplexed.

“Start reading. I’ll be out in a jiffy,” Carey picked up her purse and her carrybag and sauntered off to the bedroom.

Lee read some of Carey’s dissertation. It was either a masterpiece or the ramblings of a psychotic nutcase depending on your point of view. Carey’s thesis that pretty young college girls were so overly advantaged that male students were almost unemployable didn’t really stand up to thorough examination. It was obviously written out of spite and envy.

But the part where Carey wrote about her own experiences being able to pass as a young woman and dupe her employer, her co-workers and customers was fascinating. The supposition that the young women were trading sexual favours and allowing themselves to be molested to secure their employment and bump up their tips was explosive.

“Hey, you know this piece needs…” Lee was about to offer some thoughts and criticism about Carey’s exposé when he heard her enter the room but when he looked up he became speechless.

Carey had teased out her hair and applied heavy makeup so that she looked downright slutty. She was leaning against the door jamb wearing a black satin full-slip, black fully-fashioned stockings and black patent leather pumps with four-inch heels. Her back was arched, one leg was thrust forward and her red-lipsticked lips were pouting sexily.

Lee was instantly hard and he dropped the dissertation on the coffee table and got to his feet. He walked briskly across the room and lunged for Carey but she slipped away from him, giggling provocatively as she skipped down the short hallway and disappeared into the bedroom.

Lee found her lying seductively on the bed and he couldn’t take his eyes off her as he stripped naked.

Carey looked at Lee’s impressive manhood and wandered if she had made the right decision but she was so sexually charged there was no turning back. She wasn’t wearing her bra and her tiny nipples produced two little points in the satin gown. She hadn’t tucked either and her cock was tenting her full-cut red nylon panties.

She had dimmed the lights and sprayed herself liberally with perfume and Lee stood at the foot of the bed taking in her splendour and inhaling her exotic scent.

Carey wagged a finger at him, her long red fingernail a beacon that lured him to her. He fell on her, pressing her into the bed with his weight and Carey sighed with contentment. Their lips crushed against each other and their tongues intertwined. They made no attempt to draw out the foreplay; they were both wracked with lust.

Carey reached for Lee’s cock and found it turgid and throbbing. She stroked it and felt the power of it in her fingers. She cupped his scrotum and caressed it, drawing her long nails along the furrowed flesh and then she returned her hand to his steely manhood.

Lee slid his hands along Carey’s body, the satin garment sliding captivatingly across her soft, smooth flesh. He brushed her nipples and she gasped but his hand continued their journey down her body. He drifted his fingertips across the front of her panties and felt her cock quiver but his hand proceeded downwards to her legs.

The ultra-sheer stockings felt like a diaphanous sheath enswathing her legs. He ran his fingers up and down her thighs, tracing the backseams, circling the dark welts, toying with her garter clasps. He lifted Carey’s fingers from his manhood and slid his cock between her thighs so that he could feel the translucent hosiery on his sensitive skin.

Carey felt his sturdy appendage gliding along her stocking-sheathed thighs and she closed them tight around it, delighting in the feel of his cock humping her legs as he kissed her with unconditional passion. She wrapped her arms around him and pulled him tight, wanting to feel his body pressing against hers. She wanted to feel his longing for her, his need for her, experience his unbridled passion.

Lee’s cock ground against her legs, trapped between her thighs. His lips crushed hers, his tongue fluttered in her mouth. She could feel the heat of his bloated, pulsing organ on her delicate flesh, her own cock was quivering in anticipation of what was to come next.

Carey put out her hand, her fingers scrambling on the nightstand, searching for the tube of emollient she had placed there. She found the tube of KY Jelly, the cap already removed, ready for this exact moment.

She opened her legs wide and Lee sensed her need. He tugged at her panties but she batted his hand away. She adored the feel of the gossamer nylon garment cloaking her buttocks, scrotum and penis. She slathered Lee’s cock with the lubricious gel and guided his cock inside one of the leg openings of her panties and nestled his glans in her sphincter.

Carey grabbed a pillow and pushed it under the arch of her back and lifted her buttocks and opened her legs.

She clasped her hands behind Lee’s neck and looked up lovingly into his eyes.

“Take me Lee,” she whispered and locked her lips on his and thrust upward as Lee pressed his manhood into her sphincter.

Carey suppressed a scream when Lee’s fleshy glans pierced her tight orifice. She bit his lip and held him tight and Lee sensed that he had hurt her and he stopped.

“No! I want you inside me Lee. Make love to me,” Carey whispered and she pushed upward a little and an inch of Lee’s cock slid inside her tight channel.

Lee kissed her passionately and she mewed and moaned into his mouth as he slowly impaled her on his throbbing cock. The tight sheath of her anus girdled his penis. The feel of her body shrouded in the satin slip, her gossamer-clad legs scissoring on his flesh, the silky nylon gusset of her panties cosseting his scrotum when he was fully inside her was overwhelmingly pleasurable. He couldn’t thrust because he knew he would orgasm, he was at the peak of extremis.

When the pain subsided, circlets of pleasure radiated from Carey’s tight sphincter, her anus felt delightfully full and a deep resonant decadence began to emanate from her prostate. Lee’s belly pressed against her hard penis trapped in her nylon panties causing it to throb and leak a continual stream of pre-ejaculate.

Carey had never felt so sexually aroused and she too was on the brink of climax.

“Fuck me,” Carey whispered into Lee’s ear and she nipped his earlobe to encourage him.

Lee sought Carey’s lips and he drove his tongue into her mouth as he withdrew his penis and then drove it into her rectum. Carey chafed her legs against Lee’s flanks, knowing that her gossamer nylons would excite him further. The feel of Carey’s legs on his sides, her tight anus clasping his cock, her satin-shrouded body pressing against and her bruised lips pressing on his drove Lee into a paroxysm of lust.

He jackhammered his cock in and out of Carey’s tight channel as she clung to him, rising to meet his thrusts, biting his lips, raking her nails down his back, spurring him with her high heels.

They climaxed together.

Carey felt her anus begin to spasm, her prostate begin to reverberate, her scrotum contracted and her penis shuddered as she orgasmed. It was like nothing she ever felt before and she clung to Lee and drove her body into his, encouraging him to fuck her harder.

Lee felt Carey begin to convulse beneath him, her breathing was ragged, her face was screwed up with divine bliss and he felt the warm wet dampness on his belly as she flooded her panties.

Lee pushed his cock into Carey as far as it would go and ejaculated. Carey felt Lee’s cock quiver and then suddenly her anus was filled with her lover’s creamy milt. It dribbled into the cleft of her buttocks and soaked into the welts of her stockings.

Lee could feel Carey’s rectum milking him, extracting his seed as the warm glow of extremis became an overwhelming pleasure vortex that took his breath away,

They lay in each other’s arms, kissing and canoodling but neither of them spoke. Lee’s cock was still buried in Carey’s anus and he did not want to remove it. It felt like it belonged there. When he finally did try to extract his still engorged member from Carey’s tight sheath she tightened her sphincter and trapped him inside her.

“No! Don’t take it out. Do that again,” Carey grinned up at him, her dishevelled hair and ruined makeup making her look like a whore.

When Carey left Lee’s place early the next morning she was unsteady on her feet as she walked to her car. They had spent most of the night fucking and her ass was sore and her legs shaky, but in good way. She’d brushed her hair into the piecy style she favoured, her makeup was perfect but no longer sluttish and she was wearing the tartan pleated miniskirt, white silk blouse, flesh-toned pantyhose and black wedged high heels that she had worn to the Perky Brew on her fist day.

She drove back to Balwyn College feeling content and confident but also a little confused. She would drop off the carry bag containing the now semen-soaked shift, black stockings and red nylon panties and garter belt and the fuck-me heels. She would work the breakfast shift at the Perky Brew and attend afternoon lectures.

The door to Carey’s room flew open and Vickie stormed in slamming the door behind her. Carey had forgotten that Vickie had a key to her dorm.

“You fucking bitch!” Vickie flew at Carey with her claws extended and her teeth gnashing.

Carey narrowly avoided being scratched and bitten as they fell onto the bed and wrestled.

“You leave my boyfriend alone you fucking slut!” Vickie’s face was inches from Carey’s.

Carey gripped Vickie’s wrists and locked her legs around Vickie’s waist to prevent her from kicking and scratching.

“Vickie! Vickie! Vickie! It’s not what you think,” Carey cried out.

Suddenly Vickie stopped struggling and fighting. She leaned away from Carey so she could see her face properly.

“Carey?” Vickie was dumbstruck.

“Carey! What the fuck? I heard rumours that some tall hot chick was visiting you in your dorm and then I saw her enter your room and… and… what the fuck? What are you playing at?” Vickie’s astonishment was vanishing.

It was being replaced by repulsiveness and animosity.

“Are you some sort of fag? Are you a fucking homo or something?” Vickie recoiled and climbed off the bed.

Before Carey could answer Vickie unloaded a further fusillade of vitriol.

“No, you look too good! This isn’t some prank or fetish. You’ve perfected that look,” Vickie flung open Carey’s wardrobe and saw the female apparel hanging on the rod and the shoes on the floor.

“How long have you been doing this? Have you been sucking cock and bending over, you freak? Have you been sucking off football players and then using those lips to kiss me?” Vickie turned back to Carey.

As usual it was all about Vickie. She was the one being victimised. She was the one being duped. Her outrage was justified because she was Vickie and Vickie was the star of her own show and everyone else was an extra.

Vickie had never thought to ask Carey why she was presenting the way she was. Was Carey gender dysphoric? Did Carey need help? Did Carey need support? No! Carey had duped Vickie and Vickie was not to be duped.

“Who else knows? Are people laughing at me behind my back because my boyfriend is a crossdressing cocksucker?” Vickie’s pretty face had become ugly with rage.

Suddenly her face turned sly and evil.

“Well fuck you Carey! The Broncos defensive line tag-teamed me while I was away at the Varsity cheerleading competition last week. Those boys had nice big hard cocks and I took them all. I pulled a train Carey, and I didn’t think about your scrawny faggot ass for a single instant,” Vickie raged.

“Vickie let me explain,” Carey tried to interject.

“Explain what Carey? That you’re a man trapped in a woman’s body? That you have irresistible urges? What Carey? How do you explain your duplicitousness?” Vickie put her hands on her hips and glared at Carey.

Carey opened her mouth to try to explain how she had started crossdressing to spite young women just like Vickie but then it had become something else and that Vickie was right about Carey questioning her gender identity.

But then Carey realised that she didn’t need to. What was happening to her was personal. She was on her own journey of discovery that had nothing to with Vickie.

Carey just smiled at Vickie as she stood up and smoothed out her skirt and blouse.

“Did the tight end give you one in your tight end?” Carey smiled sweetly at Vickie.

At first Vickie didn’t get the sarcasm but then it dawned on her and the rage returned to her face.

“I’m going to out you, you faggot! I’m going to tell everyone that Carey Davenport is a crossdressing, cock-sucking, bum boy!” Vickie hissed.

“You know what? Go ahead. I don’t care anymore. I’m tired of hiding in the shadows,” Carey sighed.

“Fuck you Carey Davenport. Feel free to suck a few cocks in the car park on your way to class today because everyone is going to know you are a tranny faggot!” Vickie screeched and then she yanked open the door and stormed into the corridor.

Carey just stood there enjoying the silence. She was glad that it was finally out in the open. Then she started to laugh.


Carey turned up to her lectures that afternoon presenting femme. Nothing outrageous, just tight skinny jeans, a comfortable raw cotton bohemian blouse and low heels. Her makeup was subdued but highlighted her feminine attributes and her hair was styled piecy.

She was prepared to be jeered at, made fun of and maybe even pushed around a little but the opposite occurred. Carey received only compliments and encouragement from her fellow students and a cute boy even slipped her his phone number.

Vickie on the other hand had been suspended pending the outcome of a tribunal to determine if her enrolment at Balwyn College would be terminated on the basis of hate speech, bullying and harassment. She had made good on her threat to out Carey to as many people as possible but her plan had backfired horribly. All she had done was garner support and sympathy for Carey and found herself in front of the student disciplinary committee.

Carey turned up for work at the Perky Brew the next day dressed provocatively as usual and was surprised that most of the girls supported her. News travelled fast around Balwyn College. She dreaded having to front Desmond White but she would cross that bridge when she came to it.

Clarice Starr followed her into the break room.

“So you’re out. I know the courage that takes. You go girl!” Clarice slapped Carey on the ass playfully.

“Does Desmond know?” Carey asked.

“He does and he doesn’t care. In fact he thinks you might attract a certain kind of clientele. Your job is safe but don’t be surprised if his curiosity gets the better of him and he asks to see you in his office sometime soon,” Clarice gave Carey a knowing look.

“Well I guess I’ll just have to deal with that eventuality when it arrives,” Carey sighed.

“Am I working my usual section?” she asked as she put her purse in her locker and locked it.

“Sure, if you want. Like I said… you go girl. Your shift starts in five minutes,” Clarice left Carey alone and returned to the hostess station.

As soon as she started her shift Carey sidled up to Lee’s table. She looked around and saw that no one was looking so she leaned in and kissed him quickly.

“Do you still have the copy of the exposé I gave you?” she asked and Lee nodded.

“Shred it. I’m not gonna submit it. I’ll come around to your place after work. Make sure you have clean sheets on the bed,” Carey said matter-of-factly.

“Clean sheets?” Lee looked perplexed.

“Boyfriends always have clean sheets on their bed when their girlfriend comes to visit,” Carey smiled at Lee cheekily.

“Wait? I’m your boyfriend now?” Lee looked even more perplexed.

“Sure you are. We have a lot to talk about,” Carey leaned in and kissed him again and then she went back to work.

The End

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Well done!

bryony marsh's picture

That was a fun story of self-discovery. It could have turned abusive, but in the end (accidental pun, honest) it was about empowerment and a better life. Very nice.

Sugar and Spiiice – TG Fiction by Bryony Marsh

You Excel Yourself

joannebarbarella's picture

This little tale has all your trademarks, including the sexual escapades, but it also has your excellent writing skills.

I hope Carey and Lee find true love.

Sexually charged

KateElizabethSuhr13's picture

I was thinking in the beginning when Carey mentioned entrapment that it wasn't entrapment since Desmond was planning to do that to any young woman he found to be sexy and desperate for a job but by the end of the story I too was sexually charged. I don't find men attractive to the point of being their girlfriend but the idea of a man making me feel like a sexy woman does have its turnons.