The Bartender

Alex looked down at his drink, that his hands were cupped around the small glass. He had delicate, small hands, that belonged to a girl's, not a man's. Yet, he was, on a Friday night, at a small, dingy bar. Earlier, he got dumped by his girlfriend, telling Alex he was far too prettier to be with a girl, and instead, Alex should date other men.

Alex was always in such predicaments, mostly because of his girlish face, skinny body and overall small frame and build. He was never able to gain any weight, despite being in his late thirties. Even back when he way younger he was regularly mistaken for being a girl, since his body was smaller than that of a girl's. Even in his thirties, his body is that of a young girl's, in spite of possessing what muscles he had, but not by much. 

A welding mechanic by day, Alex is often praised for his work, despite his feminine facial features, and he gets mocked mainly for his girlish looks. One day, he decided to have a few drinks by himself at a local dive bar, to get away from his coworkers, and a very rough breakup.

He looked at his small drink once more. His small, delicate hands still clasped around the glass as he's looking down at his drink, and the table. Soon, he saw a pair of legs that looked like they went forever, before disappearing into some Converse shoes.

"Need a hand there?" the girl asked, wearing a tube-top style shirt, revealing a small belly resembling a muffin top over her worn distressed denim cutoff shorts, that were audaciously cut near her crotch area. Alex looked at the server girl's shorts for a while, before looking up at her.

"Can I help you there?" she demanded once more, moving her mouth in a chewing manner, as if though she was chewing on a gum, but nothing was present in her mouth.

"Uh, nothing for the time being." Alex says, returning his gaze back to the girl's slender, long legs once more. He felt his boner growing in his pants, but luckily, no one would be able to notice.

"You look really pretty. I thought you were a girl there for almost a second. I'll come back in a minute." With that, she quickly scampered away, not helping Alex, only leaving him even more puzzled, as he swirled his remaining drink in the shot glass.

At least she has gorgeous legs... he thought, still swirling the glass. Soon, the girl came back, with what is assumed to be the bar's owner and manager. He was middle-aged, balding, and wore a vest with a little bow tie beneath his double chin, and crisp black dress pants, topped off with shoes that shined.

"I want to give you a job. It's not much, and it's only for Friday and Saturday nights. I could use a new girl around here once more." the man says, eyeing Alex, as if reading the small man's mind. He bowed, then said quietly: "I hope you're trans."

Alex was shocked. Never did he imagine he would be one. He's simply a blue collar worker, doing welding in a shop not too far from where he was drinking, and he's there mostly to get the bitterness of a bad breakup of his girlfriend. The girl waved, and slyly smiled, as she moved her slight pot-belly like a belly dancer would. That was it for Alex, and he cummed in his jeans. Luckily, he wore black pants, otherwise; what unimaginable horrors would come about if he peed on himself in this circumstance?

Alex always crossdressed as a girl, mostly to take pictures and post them to his forum, where he would hit it off to the comments about his body, and especially his long legs. He knew his wouldn't compare to the girl's, or so he thought. She leaned over, and whispered in his ear:

"We're a trans friendly business. He's the manager, and he saw right away he wanted you to join our club too." Alex blushed. As mentioned, Alex only dressed for his cameras; this was going to be something new for him, as he never really dressed in public before.

And now, the manager wants him to dress like a girl full-time, especially on Friday and Saturday nights.

Only problem was, his coworkers also come here to drink and flirt with the girls in the bar, and other girly men like himself. He was already hard at that thought, but eventually, he agreed, and needed to change into his outfit. Alex quickly ran to his car, and dug around in his bag for his 'girly' outfits, which consisted of a t shirt, black blazer, ripped denim shorts he swiped from his ex-girlfriend, and one of her pairs of Converse. He quickly got changed, but got aroused as he felt the hard, dried cum at the hem of the shorts, where he masturbated until he came, and ejaculated into the shorts. Even through his erection, it was completely unnoticeable even as he wore the daringly short shorts, and tried his best not to come again, even as his very tiny penis was throbbing against the fabric of his former girlfriend's shorts. He wanted to masturbate right then and there, as he got into complete character, like he has done lots of times before. He took off his baseball cap, revealing shoulder-length hair, and tied a small part of his hair so that he resembled a bratty girl wearing a blazer jacket, t shirt, denim shorts and Converse shoes while not wearing any socks. He has done so a few times, only to masturbate what it felt like to wear Converse without socks, and to arouse his fellow foot loving followers.

But not tonight, even as it took a lot of power to contain his masturbation urge to do so, as he entered the bar once more. No one took notice of Alex at first, until one man took a look at "her." Her long, lean, and exposed legs were visible for all to see, as Alex strolled casually to the counter, where he was guided on how to mix and serve orders for customers. 

And, he learned pretty quickly, taking customers orders, mixing them in a professional manner as if he's done it before, but it was his first time, and his first night. Alex quickly took the girl role as 'she' took orders from the people at the tables, and cleaning. Even as patrons doused Alex's legs, he wasn't fazed. In fact, he seemed to be enjoying every moment of it, and his boner was erect, but luckily, no one was able to see it, even as Alex was uncontrollably coming in his shorts, the warm liquid running down his slender and long, toned legs, and into his Converse. His legs glowed with the liquid as he walked around, his cum dripping and swinging from the bottom of the shorts, but to the discerning eye, the cum drips blended in perfectly with the ripped threads of his shorts. His shorts were drenched with beer from patrons, so no one knew he had peed on himself, and it only had been thirty minutes since he started working as a crossdressing bartender. 

A fellow trans worker pointed to Alex's thigh, and he looked down, to be greeted to a thick white cream clinging to his left thigh, while a longer thread hung from the middle of the original thread that hung below Alex's shorts hem. Luckily for him, he was behind the counter once more, and that thick white cream had laid itself against Alex's ankle now, while still running down. His bare feet inside the Converse were now soaked, both from the patrons pouring their beer on his legs, and the semen, and squished as he walked about, and he was getting fantasies about his feet as he squished about, wriggling his toes in the dark confines of his shoes.

The night was only getting longer, and soon, his heart dropped. He recognized a couple of men in his department. He knew he would be dead meat of anyone found out he was dressed like this, but he calmed down, and took their orders. One of his coworkers pinched his butt, making him squeal a little, and jumped in a playful manner, which was unlike him to do so. And, out of nowhere, another of his coworker pulls on his belt, before grabbing his shorts, and at the same time, stuffs a large amount of dollar bills into his shorts, before letting him go. He felt the dollar bills being squished next to his tiny erection as the larger folded bills were pushed next to his tiny erection.

For the most part, Alex enjoyed his time behind the counter, serving and mixing drinks, where he can hide his tiny erection as he does so. The dollar bills were hiding his bulges well, and hiding his 'tips' all the while he kept serving, with each new customer stuffing more than he could carry in his shorts for the night. There was nothing Ale could do, as he imagined the dollars getting wet from his secretions beneath the shorts, and his girl panties, as more of his secretions leaked beneath the hem of his shorts. When the night was over, Alex knew he had to deal with the smelly and crusty aftermath of what he was going through, and sure enough, more of his sticky secretions dripped out of his shorts, onto his legs, his Converse, and even onto the bar's floor and carpets. His Converse had painted mosaics of prior dried secretions when he did photography sessions in dark alleyways, and now, they're covered even more, as he walked all night, serving customers and taking their tips.

With the night now ending, Alex carefully took out his money, and laying them out on the pool table, some were still wet with semen, and urine, as he began counting how much he got in that single night. In total, he got far more than his day's wage at his current welding job. And he's hoping this would be his only time cross-dressing for the bar.

Soon, other girls gave him their share of their tips, and even one of the girls stuffed some more dollars down into his shorts, by putting her hand down in there as well, making sure the dollars stay in his shorts, and panties by carefully placing the dollars next to his crotch and fully erect, but tiny, penis, and using his panties to secure it. All the while keeping eye contact with Alex, and smiling at him.

The night was now officially over, and Alex, even though he's tired, took photos in a dark alley, before he finally called it a night.