Volume 01 - Dirty Shorts

Ashley turned and walked into the bar. He looked around, but no one was showing him any interest. He knew they’d probably heard his yelling, but he was glad to see they didn’t care. It was probably a normal thing here, people yelling and hurling insults. His altercation with Tiny not causing any extra scrutiny would certainly make the night easier; he didn’t need people looking at him too closely. If anyone noticed he wasn’t a real woman, he’d be fortunate if they only kicked his ass. Ashley was confident however, that no one would catch on to the fact he was really a man. He spent hours getting ready for this and was positive he could pull it off; he even perfected his squeaky bimbo voice and had been practicing his airhead giggle for weeks.
    He rarely did drag but certainly enjoyed it on occasion. Mostly, he liked wearing high heels and wore them any chance he got. It was a lot of work doing full drag. Ashley was lucky to have natural curves and a shapely ass, so he didn’t need to worry about padding around the hips. It was easy for him to stuff a small, B cup bra and use a little makeup to silhouette his chest, making it appear like he had a luscious rack. The hair was easy, throw on his favorite wig and style it a little if needed. Ashley preferred not to think about the unpleasantness that was dick tucking ; tucking was a painful bitch. It’s not easy being a queen.
    Tonight was about proving he could pass for a real woman. Ashley thought back to a few weeks ago, when he went out with some friends while in drag. His friend, Jared, kept saying he would never be able to pass as a woman, but that didn’t stop him from trying to feel up under Ashley’s skirt. Ashley had made it clear he needed a man, one who was big and capable of holding him down and wasn’t afraid of fucking him good and hard; a man who wasn’t intimidated by Ashley’s height when he wore high-heels.
    At the time, Ashley said it wasn’t about looking like a real woman but about how he felt when he dressed up as one. Which was total bullshit; all Ashley really wanted was to wear the high heels out dancing. But, no one would understand that. His gay friends were fine with him dressing in drag, but if he simply wore high heels while dressed as a man, they would ask all kinds of questions and act like he was a freak for having a fetish for wearing woman’s shoes.
    So, by the end of tonight, he was going to prove Jared wrong, or so he hoped. Moving forward with his plan, he walked up to the bar and ordered a drink. Thankfully, the bartender didn’t ask for any identification or he would have had to come up with some excuse for how he must have left it somewhere. Ashley picked up his drink and headed for a booth along the wall where the bar’s weak lighting was even lower. The dim light would make it harder for anyone to notice anything odd about him, like that he had a penis tucked between his legs, for example, but it would also make it harder for him to check his makeup.

    ****

    Rick sat at the bar, facing the door, drinking his beer. He subtly watched as the pretty little redhead adjusted the short skirt before strutting up to the bar. Well, not so little , he thought to himself. Wearing those come-fuck-me heels, Gorgeous was probably just a couple inches shorter than Rick. The shoes were black with pointed open toes. Rick could see those sexy toes were painted the same deep red as the hair flowing down to broad shoulders. If Rick hadn’t already noticed an Adam’s apple, he would have known it was a man from those muscular shoulders alone; women just didn’t have shoulders like that. Of course, no straight man would notice those things either, because they would be staring at that chest. Wearing a skin tight, low cut, black top with a padded bra and chest makeup; it looked like he was stacked. Rick had to examine closely to make sure the guy didn’t have implants, his chest looked so real.
    Rick watched as he took his drink over to a booth in the shadows along the back wall. Such a fine ass barely covered by the black leather miniskirt. An ass Rick wanted to get to know better. And those legs, damn Rick was hard just imagining those legs wrapped around his waist. The high heels made his shapely muscles stand out as they flowed up into his perfect ass. Rick first noticed two things about a person: a fine ass and a personality. One without the other just didn’t work for him. He already noticed that tight, round ass came