We were watching the game one night at the bar where my sister worked when the bet was made. You see, I'm a makeup artist for movies and television and for this reason I have been the subject of a lot of teasing and insults by my roommate. My roommate isn't the most manly guy, in fact he is quite the opposite. He is short, skinny, and has never had a girlfriend in his life. Sure he acts tough and talks a big game, but that's all it is. Now you're probably wondering why I don't just move out or kick him out of the apartment. Believe me, I would love to, but rent is expensive and for now it's the best I can do. Also, as bad as he is, he's still the only friend I have in the city. We actually went to college together and when I moved to Los Angeles for my job, he had already been living here for a year. He invited me to be his roommate and not knowing anybody else in the city, I accepted his offer.
Now, as I was saying, we were at the bar watching the game, and as usual he was hitting on my sister. My sister of course had no interest in him and made this clear every time, but he persisted. He would ask her out constantly and she would always say no, but he never took the hint.
"Dude, your sister is so hot," he said as my sister walked off in disgust.
"Shit, man," I replied, "That's my sister."
We went back to watching the game and during the commercial, a teaser was shown for a movie I had worked on. The movie was about a guy who goes undercover as a girl to get a job. Now, a lot of people, including myself, thought the actor in the film passed very well as a woman, but my roommate was unconvinced.
"Dude, you can totally tell he's not a chick," he argued.
"You're just saying that because you know he's a guy," I challenged, "If you saw him for the first time as a girl, you would think he was a real chick."
"No, dude," he said, "You dress any guy like a chick and I can pick him out."
"You wanna bet?" I asked sensing an opportunity.
"Sure," he replied feeling pretty confident.
"OK," I said as my sister returned to the table with more beers, "If you win, you get a date with my sister. You OK with that, sis?"
"OK," she agreed.
"But," I continued, "if I win, you have to let me dress you up like a woman and spend the entire night at the bar in drag."
"You're on," my roommate said confidently, "I hope you wear something sexy on our date, babe."
My sister walked away in disgust and we began discussing the terms of the bet. Next weekend was the bar's usual ladies night. That night my roommate and I will come to the bar where I will have twenty guys made over into women. If he could pick out all twenty, then my sister would go out with him the following night. If he failed, he would come to the bar the next ladies night in drag.
The night of the bet had finally arrived and I had been busy that day transforming men into women. I purposely included a few guys who had no chance of passing to get my roommate to feel overconfident. He quickly picked these guys out the moment we entered the bar and sent them on their way. That was three men down, seventeen to go. We made our way through the bar and he quickly picked out five more. These guys were more convincing, but they each had features that gave them away. For some it was their hands, for others it was their jaw structure, and for another couple their Adam's apples gave them away.
There were now ten guys left and my roommate took a different approach to the situation. He walked up to several women and talked to them directly. He picked out five more men when their voices gave them away. Still, I wasn't nervous. The final five men were very convincing and even I would have a hard time picking them out. So my surprise, he was more observant than I gave him credit for and picked up on the tiniest subtleties. I don't know how he did it, but soon he was down to the last one. He wandered the bar for a while talking to every woman he saw. Finally, he was about to give up when a woman sat down close to him at the bar.
"Hi," he said to her, "Can I get you a drink?"
"Sure," she replied with a smile.
They began to talk and my roommate told her about the bet he had made with me. The woman asked him how he could tell which women were really men and he began to tell her what he looked for. Suddenly, his expression changed and a smile came over his face.
"Wait," he shouted, "You're a man!"
The woman threw her drink at him and walked away angrily as I sat by and watched. I said nothing as he began to rub his victory in my face.
"I'm looking forward to our date," he said to my sister as she looked at him angrily.
The next night, my sister showed up at our apartment wearing a little black dress and her highest pair of heels. My roommate was all over her as she tried to fight off his advances. I have to admit I felt bad for her and wished I didn't make her part of the bet.
"Let's just get this over with," she said.
They left in her car, since my roommate didn't have a car of his own, and I waited for them to come back. They returned a couple hours later and I watched as he pulled her to the couch and forced himself on her. She gave in and they began to kiss.
"Ugh, I know I'm going to regret this," she said, "Go to the bedroom and get undressed. I'll be in shortly."
My roommate ran to his room and stripped off all his clothes. He jumped on top of his bed and waited for my sister to return. When she finally entered the room, he stared in shock at what he saw. You see I don't actually have a sister, but I have a brother who loves cross-dressing. As far as our bet, I had been planning to make the bet long before that night.
It all started back in college. My brother was visiting and agreed to let me make him over as a girl. He is straight, but he also loves dressing up. Well, I had finished the makeover and we were having lunch when my future roommate showed up. I began to introduce my brother, but he was all over her before I could get a word out and we decided to go along with it. After college, my brother started working at the bar and the owner was cool with his cross-dressing so he started working as a girl. Even though he didn't live full-time as a woman, my roommate had never met him as my brother and was convinced he was a girl.
As my brother stood naked before him, no longer wearing his wig and prosthetics, my roommate realized he had lost the bet. He had been fooled and he knew it.
"Wait," he said, "You said there were only twenty?"
"There were," I responded, "The last one was a real woman. You blew your chance with her dude to go on a date with my brother."
Well, here we are back at the bar. My roommate is dressed up in the outfit my brother wore for the date and the guys here are all over him. What my roommate didn't know until tonight, is that tonight isn't ladies night. It's gay night and some of these guys have a thing for guys that look hot as chicks. I hope he has a good time.
Doug is a makeup artist who is working on a new film about a man that has to pose as a woman. Doug's roommate is convinced that no man could ever fully pass as a woman and that he could pick out any cross-dresser no matter how good they look. Doug, tired of his roommate's macho attitude, makes a bet with his roommate in which he will try to prove him wrong. If Doug's roommate wins, he will get a date with Doug's sister. If he loses, he must let Doug make him over into a woman and spend a night in drag at the bar where Doug's sister works.