Coffee Shop Girl

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. Please read Talespin's stories here on Literotica and provide him with some feedback. All writers crave encouragement and constructive criticism.

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

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.