T-Bar

"Wow what a game! We will be back right after this to break it all down. Stick around."

As the broadcast went to commercial I yawned. That had been one of the best basketball games I had watched in a long time but after regulation and then three overtimes I was getting sleepy. Glancing over at the clock I winced. It was well past one in the morning.

I reached over for the remote to turn the TV off when I heard a key in the lock of the front door of my apartment. Looking over from the couch I watched as my roommate Jamie came in. I was about to ask him how his date went when a tall, muscular guy followed him in. Never mind.

"Hey," Jamie said to me as they came in. He glanced over at the TV and then back at me. "You still watching a game?"

I pressed the power button on the remote control. "Nah, it just ended. I'm going to bed," I said. "I'll see you tomorrow."

"Goodnight," Jamie said as I started to walk towards my bedroom. When I glanced back at him he gave me a devilish smile and then winked as he nodded towards the guy behind him. I couldn't help but laugh.

As I closed my bedroom door behind me and got into bed I was still smiling at Jamie's shenanigans. He loved to brag about the hot guys he brought home but that was the first time he had done it in front of a guy. It fit right in with his playful personality though.

I turned off the lights and laid down. I was just drifting off to sleep when I heard Jamie's bed begin to squeak. Our bedrooms shared a thin wall so less than a minute later I was treated to the symphony of sounds of Jamie and his date having sex.

They lasted about ten minutes. At that point I heard two loud moans in quick succession and then the creaking of the bed stopped. With silence descending on the apartment I rolled over and pulled my blankets up to my chin. I fell asleep immediately.

Late the next morning I was sitting on the couch when the door to Jamie's room opened. He shuffled out, hair and clothes a disheveled mess, and slowly made his way towards me. Lowering himself down onto the couch next to me he let out a loud sigh.

"Someone had fun last night," I said with a smile.

"Yeah," Jamie said with a tired chuckle. "He was a lot of fun." After a pause he added, "and he had a really big dick."

I laughed. "Of course he did."

Jamie looked over at me. "How did you know?"

I rolled my eyes. "What was it Alex called you the other day?" I asked. "A 'size queen'?"

He laughed. "I never thought my straight roommate would know what a size queen is."

I shook my head. "You've told me so much about your sex life that I'm not sure I can be considered straight anymore," I said teasingly.

"Ooo," he cooed. "Does that mean you are thinking about switching teams?"

"You wish," I said with a smile. "Although based on how often you get laid versus how often I do maybe I do need to rethink my strategy," I joked.

"Well let me know if you want help setting up your Grindr profile," Jamie said playfully.

"Yeah, right after we set up your Tinder profile," I replied.

He laughed.

I loved our playful banter and it was great having a roommate that I could verbally spar with. Our dynamic was comfortable and fun and it had been like that since the day I moved in. We just seemed to get along.

There was a comfortable silence for a while and then Jamie said thoughtfully, "You know I've had sex with a woman before, right?"

I looked over at him with surprise. "No," I replied. "Did you really?"

"Yeah, I had a girlfriend in high school." He paused and then said, "unfortunately having sex with her just cemented for me that I was actually gay."

"Bummer," I said.

"It's ok. We became really good friends after that and she was actually the first person I came out to," Jamie said. "But at the time I felt really guilty because the only way I could cum was by thinking about the captain of the football team."

"That sucks," I said sympathetically. Then I smiled because I couldn't help but be amused by Jamie fantasizing about the captain of the football team.

He saw my reaction. "You think it's funny that I fantasized about a football player huh?" When I nodded he said, "I couldn't help it. They used to make us all take showers after gym. I had to look!"

I laughed.

"But it worked out," he said. "I see pictures of my ex and her beautiful family on Facebook all the time. Meanwhile I'm out here living my best gay life."

I smiled. "You sure are."

After Jamie's confession I started thinking about my own past and I decided to share something with him. "So," I started, "is it my turn to confess my youthful sexual experimentations?"

Jamie looked over at me with surprise. "If you have some then yes, absolutely!"

I smiled. "In college I jerked off with another guy."

He immediately sat up. "What? Really?"

"Yep," I answered. "More than once."

"Oh my God, tell me everything," Jamie said excitedly.

I laughed. "So there was this guy who lived in the same dorm as me and he loved downloading porn. Late one night he was showing me his latest downloads and I guess it was obvious that I was getting turned on. He suggested that since we were both going to jerk off later we should just do it together right then."

"Wow," Jamie said. "And you did it? How open minded of you."

"To be honest I was really nervous," I said. "But he was so laid back about the whole thing. He just whipped his dick out and started tugging on it. He was even cracking jokes about the scenes we watched. He made me feel comfortable enough that when he wanted to do it again the next weekend I was down."

"How many times did you do it?" Jamie asked with interest.

"Maybe six or seven times?" I said uncertainly. "Not sure." I suddenly smiled. "But you'll be interested to know that the last few times we helped each other out."

He raised one eyebrow.

"We jacked each other off."

"Hand jobs?!?!" Jamie exclaimed. He pretended to fan himself like an over-excited southern belle. "Well I never."

I laughed. "Yep, it was fun but before you ask that's as far as it went. No blow jobs or kissing or anything else. Just a couple of drunk dudes getting off to straight porn."

Jamie threw himself back on the couch. "This is amazing! I never would have guessed you did something like that before." He looked over at me with a smile. "Anything else I should know about?"

"Nope," I answered honestly. "That's it."

The following Friday I returned to the apartment after playing basketball with friends. When I walked in Jamie was sitting on the couch looking at his phone. I caught a brief glimpse of a naked male torso on his screen and I knew he was looking at either porn or Grindr. Same difference.

As I set my bag down next to the couch Jamie looked up. Seeing my basketball shorts and sweaty t-shirt he asked, "So how did your game go?"

"It was fine," I said. "We just played pickup." I took a drink of water. "And it was fun until this guy on the other team started taking things way too seriously. He must have outweighed me by a hundred pounds and-"

Jamie laughed. "Everyone outweighs you by a hundred pounds," he cut in. "How much do you weigh? One twenty? One thirty?"

I ignored his jab at my skinny physique. "Anyway," I said. "Because he outweighed me he just kept backing me down into the paint and then scoring."

"Isn't the point to score?" Jamie asked sarcastically.

"Yes, obviously," I said with exasperation. "But it's a pickup game. You're not supposed to just find a mismatch and keep exploiting it. The game is supposed to be fun."

"I'm sure it was fun... for him," Jamie said teasingly.

"Ugh, never mind," I said. I looked at the phone in his hand. "What's going on with you tonight?"

"You're looking at it," he said. "I'm just taking it easy tonight. Tomorrow night Alex and I are going out."

"That's cool," I said. "Where to?"

"We're going to this place called T-Bar," he answered.

When he didn't say anything else I looked over at him. He seemed to be looking at me expectantly.

"I don't know what that is," I admitted.

"It's a trans bar that also has dancing."

Once again he looked at me expectantly. Once again I didn't really know what to say. Was he going there to pick up trans men? I knew he wasn't attracted to women. I shrugged.

"Alex and I will be dressing up like women."

"Oh," I said. "Interesting. I didn't know you were into that."

"Well, I wasn't," Jamie said. "But I've always had a thing for makeup and then last year Alex and I went to this amazing drag show. The outfits were incredible and they inspired us to see what we could come up with."

He laughed. "Turns out neither of us knows how to sew very well," he said with a shake of his head. "So we just went shopping instead. Turns out women's clothes are super cute."

I laughed. "Who knew?" I said sarcastically.

"So yeah, we bought some outfits and we dressed up one night at Alex's place. It was a blast. I was surprised how much fun it was to put on makeup and prance around in a skirt. It wasn't something I had ever thought about doing before but I enjoyed it."

"After we had a few drinks Alex suggested we go out dancing. I wasn't sure about it but then he told me about a place he had heard of that catered to trans women and crossdressers. T-Bar."

"Cool," I said. "So you went?"

"Yeah," Jamie said with a smile. "And he was right. We fit right in."

I nodded. "So, lots of cute guys there?"

He laughed. "Usually there is. We've been a few times and it varies." He shook his head. "Man, straight guys are something else."

"What do you mean?" I asked.

"It's so fun flirting with them," Jamie said with a smile. "Alex and I just get to dance and have drinks bought for us."

"Sounds like fun," I said.

"Definitely. So yeah, I just wanted to let you know," Jamie said. "I didn't want you to be confused when two hot girls come out of my room tomorrow tonight."

I laughed. "Noted."

The next night I was watching a basketball game on TV when I heard a knock at the door. When I walked over and opened it I saw Jamie's friend Alex. He was pretty average in height with a thin frame and thick, dark hair. In his right hand he carried a large duffel bag.

"Hey Alex, come on in," I said as I stepped back. "I think Jamie's in the shower but he said you can go ahead and start getting ready in his room."

"Thanks," Alex said with a nod as he shut the door behind himself and started towards Jamie's room. Halfway there he looked back at me. "Did Jamie tell you what we are doing tonight?"

I smiled. "Yes he did."

He smiled back. "Get ready to be blown away!"

I laughed as he headed into Jamie's room and then I went back to watching the game. More than an hour passed then I heard the door to Jamie's room open. I looked over as Jamie emerged, fully transformed.

Jamie sashayed out wearing a pink wig, tight grey top and a short white skirt. I didn't know where Jamie had learned to put on makeup but her cheeks, eyes and lips all had noticeable changes. Perhaps it was applied a little heavy but I was impressed by how much Jamie looked like a woman. I found myself automatically switching to female pronouns in my head when I looked at her.

"Hey roomie," she said with mock seduction.

I laughed. "You look great," I said seriously.

Alex appeared a few seconds later dressed in a bright red, low cut dress. Her wig was blonde. She wasn't quite as passable as Jamie but in a dark club or bar it probably didn't matter. I complimented her too.

"Come on Alex, let's do a shot before we go," Jamie said.

She poured them each a shot of tequila and they quickly downed it. After that they fussed over their wigs and complimented each other's outfits. As they slung purses over their shoulders I smiled. I was thoroughly enjoying this new side of Jamie.

"Ride's here," Jamie said with a look down at her phone.

Alex nodded and then they both walked towards the front door. Perhaps aware that I was watching they both swayed their hips in an exaggerated manner. As they existed the apartment Jamie looked back over her shoulder.

"Don't wait up," she said seductively.

I laughed again as the door closed. Jamie was in rare form. I had seen him flirt with guys before but this was a whole other level. I was happy for them as it looked like they were going to have a lot of fun.

The next day I awoke early and went out to run some errands in the morning. When I returned to the apartment Jamie was laying on the couch watching TV. As I took a seat next to him I noticed he was back in his regular clothes. He looked exhausted.

"Late night?" I asked.

He smiled wearily. "Yeah, but it was so fun."

"What was his name?" I asked playfully.

That made him chuckle. "Brian." After a pause he whispered, "God bless straight boys."

I laughed and then a question occurred to me. "So which do you prefer," I asked. "Straight guys or gay guys?"

"Gay guys," he answered immediately. "Straight boys are fun but they usually don't know how to fuck. They just want to shove it in and pound away. Good anal requires more finesse than that." He rubbed his butt as if remembering a particularly rough session.

That made me laugh. "Well, I'm sorry to hear that your unskilled straight hookup didn't know how to put his penis in your gay ass."

Jamie laughed loudly. "Thanks," he said sarcastically. "But I do love straight boys. The ones who like trans women are very..." he trailed off as he searched for the right word. "Persistent." He smiled. "And in some ways that kind of attention is intoxicating."

"I'll bet," I said.

"Sometimes I just wish they wanted more than sex," he said. "Every straight guy I've brought home basically runs out the door as soon as they cum."

"That sucks," I said sympathetically.

"Oh well," Jamie said. "Price I pay."

Over the next few months I saw Jamie and Alex dress up like women at least ten times. The day after Jamie would always tell me about the fun they had and the guys they hooked up with. At one point I asked him if dressing up was going to be a more permanent thing for him but he just laughed and said that he was only having fun with it.

One Thursday night Jamie and I were hanging out at our apartment. I was watching basketball and Jamie sat next to me looking at his phone. The one time I looked over to see what he was doing I saw a picture of an erect penis on his phone so I tried to keep my attention on the game.

"What are you up to this weekend?" He asked conversationally.

"Not much," I answered. "I'm going to happy hour tomorrow with some coworkers but the rest of the weekend is free. How about you?"

"I have a date tomorrow night with this guy I've been chatting with. Should be fun," he said with a smile. "And then Saturday night I thought about going to T-Bar."

"Sounds like fun," I said.

"It would be," he said, "but Alex can't go." He looked over at me and asked casually, "do you want to come with me?"

I laughed. Looking over at him I saw that he was serious. "Umm, I don't think so," I said gently. "It's not really my scene."

"It wasn't my scene until a few months ago," Jamie responded.

"That's different," I said. "You like guys."

"Yes," he said. "But you don't have to like guys to go there with me. It could just be a fun night out with your roommate. We've gone out to bars together before."

That was true, we had gone to bars together before. Including a gay bar. But this was different. With him dressed up like a girl and me dressed as a guy it might look like we were together or something. I didn't want to cramp his style.

"I don't know," I said. "I don't want to get in your way."

Jamie looked confused. "You won't get in my way," he said. "Just the opposite."

I wasn't quite sure what that meant but as long as he didn't think I would cock-block him then that was fine. I assumed he just planned on ditching me when he met a guy he wanted to hook up with but that was also fine. I could just go home at that point.

I actually considered going. I thought about the time he dragged me to a gay bar and how it ended up being a really fun night. One guy did hit on me but Jamie was there to quickly shut it down. The rest of the night was just drinking and having a good time. If going with him to T-Bar was like that then perhaps I should go.

And speaking of T-Bar, I had to admit to myself that I was a little curious about it. Was there really a whole bar full of trans women? After seeing Jamie and Alex dressed up I wondered how attractive I would find the women there. Not that I wanted to take anyone home but I was curious.

I shrugged. "Alright, why not?" I said.

Jamie's face lit up. "So you'll go?"

"Yeah, I'll go," I said.

Jamie's enthusiastic reaction made me smile. He did a little fist pump and then he practically knocked me over when he hugged me. Sitting back he just sat there smiling at me. He seemed to be contemplating something as his face slowly took on a thoughtful look. Finally he nodded.

"You're gonna make a cute girl," Jamie said.

"What?" I said immediately. "Wait, no," I said distressingly as I put my hands up. "I'm not dressing up like a girl."

Jamie looked confused. "Why not?"

I barked a laugh at the absurdity of his question. "Because I'm not going there to pick up guys," I answered. I thought we had already discussed that.

"Just because you are dressed like a girl doesn't mean you have to pick up guys," Jamie said. "Besides, it will be much harder for me to find a hookup if you go as a guy. But if you go as a girl..."

I looked at him with exasperation. "I'm not dressing up just to make it easier for you to get laid."

"Come on," Jamie said pleadingly, "I need a wingman. Sorry, wing-woman," he corrected with a smile. "Most of the guys there come with a friend so I just need you to be a distraction."

I arched my eyebrow quizzically.

"Not that kind of distraction," Jamie said with a laugh. "Just let him buy you a drink while I work my magic on his friend."

I wasn't sure how I felt about letting a guy buy me drinks. I wouldn't want to give him the wrong idea. Shaking my head I said, "I don't know Jamie. That seems like a lot. Can't I just go as a guy?"

He sighed. "Come on, it will be so much better if you dress up with me. My favorite part about going to T-Bar is dancing with Alex and acting like girlfriends. It would be a totally different vibe if you went like that," Jamie said as he motioned to my clothes.

I looked down. I could understand Jamie's point but I was resistant. "You realize it won't work, right?" I said. When Jamie looked confused I clarified. "Trying to make me look like a girl."

He looked at me seriously. "Yes it will," Jamie said confidently. "With your skinny body I can think of ten different outfits that would look good on you. And your face is definitely cute enough. I honestly don't think I'll have a lot of trouble making you look passable."

I shook my head in disbelief.

"But the important thing is that it doesn't matter," Jamie said. "It doesn't matter how good you look. I want you to dress up because it will be more fun that way. For both of us."

I sighed.

After a pause Jamie smiled and said, "besides, no matter what you look like there is no chance that you will be the ugliest girl there. Some of them don't even try." He mimed stroking a beard.

I actually laughed at that.

"So come on," Jamie said. "It will be fun. I promise I'll take care of everything and you can just enjoy yourself." He smiled at me. "Will you let me dress you up? Please please please?"

I looked at his pleading face. How did Jamie make even the most ridiculous idea seem reasonable? He had somehow reframed dressing up as a woman as only a means to having a fun night out. It was incredible.

I couldn't believe it but once again I found myself considering it. I didn't have anything against dressing up per se but it just wasn't something I had ever wanted to do. I mean sure, women's clothes could look sexy, but I just never wondered what they would look like on me.