T-Bar

That's when I realized my biggest concern. I was worried that I would look bad. There weren't a lot of things I was scared of but I hated being embarrassed. I knew I wouldn't know anyone at T-Bar who would judge me but I wanted to feel comfortable enough to go out in public.

I thought about what Jamie said about making me look passable. He seemed to really believe that he could do it. Yeah, I was thin and I lacked overt masculine features like a strong jawline but it was gonna take a lot more than that to make me look like a woman. But I trusted Jamie so I made my decision.

"Fine, I'll do it," I said reluctantly.

Jamie clapped his hands. "Yay! This is gonna be great." He looked me up and down. "I can't wait to dress you up."

I looked over at him. "Nothing slutty," I said warningly.

He looked over at me innocently. "Of course not," he said but then a smile crept across his face.

"I'm serious," I said.

"I know," he said earnestly. "Don't worry, it will be tasteful."

I couldn't believe what I had just agreed to.

The next night I went out after work with some coworkers. We had half-priced drinks at the restaurant bar across the street from our office while we tried not to talk shop. I wasn't really that close with anyone so once a few people started leaving I joined them. When I got home the apartment was empty.

After watching basketball on TV for a while I went to bed. As I lay down I thought about T-Bar. Jamie had told me a lot about it but I still didn't quite know what to expect. And the fact that I would be dressed like a woman was making it hard to know what the experience would be like.

I was starting to get a little nervous about dressing up. Jamie had said that he would take care of everything but I couldn't help wondering what it would be like. Would it feel weird wearing makeup? Would I have to walk in heels?

After thinking about it for a while I laughed at myself. It didn't matter. I wasn't dressing up to impress anyone, I was doing it to have a good time with my roommate. I promised myself that I would try and relax and have fun with it. I fell asleep quickly after that.

When I woke up the next morning I felt good. I took my time waking up and by the time I got out of bed I heard Jamie's bed start squeaking. Laughing to myself I used the bathroom and then sat back down on my bed and looked at my phone. I tried to focus on what I was reading but by then the squeaking was pretty loud and I could hear moaning.

I don't know how long they lasted but finally the squeaking stopped. About ten minutes later I heard the front door of our apartment open and close. Getting off my bed I walked out into the living room.

Jamie was standing in the kitchen. He was wearing a tank top and shorts and had a glass of water in his hand. When he saw me he smiled.

"Did we wake you up?" He asked.

"No," I replied. "I was already awake. But I guess this means I don't have to ask you how your date went."

"Nope," Jamie said. After a pause he smiled and said, "are you ready for tonight?"

I laughed. "Sure," I said nonchalantly.

"Oh come on," he teased. "You're more excited than that."

I smiled. "Ok, fine. I'm a little excited," I said honestly.

"Good because I already have your whole outfit picked out," he said eagerly. "Wanna see?"

"Ok."

Jamie went to his room and came back a few minutes later. In his arms was a pile of women's clothes. As he set everything down on the coffee table I had a brief moment of consternation but I was able to quickly shake it off.

Jamie lifted up a black bra. "This is called a pocket bra. It has little pouches in the front where I can add some inserts to give you a small bust." Picking up the underwear he added, "and these are your panties. They are a little smaller than the ones I wear because of your skinny ass."

I laughed at his teasing as I looked at the plain black panties in his hand. I couldn't help but breathe a sigh of relief that it wasn't a thong. So far so good as far as I was concerned.

"For your outfit I went with a skirt and crop top set," Jamie said as he picked them up. "I know plaid skirts are cliché but with your long, skinny legs it will look good on you. Plus it goes well with this top."

I looked them over. The most important thing to me was that the skirt didn't look too short. Plus, the crop top had long sleeves so at least I wouldn't be showing off that much skin.

"Not bad," I said. "You kept your word about it not being slutty."

Jamie smiled. "See? I told you to trust me." He looked down at my legs. "Once you shave you'll be good to go."

"Hold up," I said immediately. "I'm not shaving my legs."

Jamie gave me a withering look. "Come on, you have to. You can't go out with hairy legs."

I shook my head. "If the guys I play basketball with see my legs shaved I'll never hear the end of it," I said seriously. As a compromise I added, "I'm willing to shave my chest hair but just not an area of my body that my friends can see when we play ball."

Jamie looked at me for a long time and then sighed. "Fine," he said dramatically. "I guess I can try to find you some panty hose or some leggings or..." He trailed off but then said, "Aha," as he turned and practically ran back into his room.

He returned a minute later carrying something black in his hands. When he got close he unfurled it to show me two long, black socks. They must have been almost two feet long.

"I forgot I had these," he said with a smile. "Here, try them on."

I took them from him and quickly put them on. They were actually pretty comfortable and they came up above my knees. I bent my legs and the elastic at the top of the sock seemed to do a good job holding it in place.

"Nice!" Jamie said excitedly as he looked at me. "That will work. Now all you have to do is shave your legs above the top of the socks."

I opened my mouth to protest but Jamie quickly added, "I've seen your basketball shorts and they go down past your knees. You said you are willing to shave any part of your body that your straight friends can't see."

I thought about going back on what I said but ultimately I decided to just let him have this. He was right that my friends wouldn't see that. I nodded.

"Great! Then you just have to shave your chest, armpits, face and pubes and you should be good to go." He smiled at me. "I told you this was gonna be fun!"

"Wait," I said. "Why do I have to shave my whole body? Nobody is gonna see any of that."

"It's part of the outfit," Jamie replied matter-of-factly.

I rolled my eyes. "How is shaving my balls part of the outfit?"

Jamie didn't say anything for a few seconds. Finally he said, "it's part of the experience." He sighed. "Look, you don't have to. I'll understand if you have a date coming up and you don't want her to see your body shaved. But if not I hope you'll consider shaving. It will make wearing this outfit that much more enjoyable."

I nodded but didn't answer. As I took off the socks and gave them back to Jamie I thought about what he said. If he really thought shaving my body hair would enhance the experience then I figured that I should at least consider it. Besides, I didn't have any dates coming up and I had promised myself to just relax and have fun.

After Jaime returned all the clothes to his room we sat down on the couch together. He told me all about his date the night before and how good the sex was. After that we just hung out and watched TV while we looked at our phones. In the late afternoon I decided to stop being lazy and go for a run.

After I got back and cooled down it was time to clean up. I stripped down in the bathroom and looked at my thin, naked body in the mirror. I wasn't the hairiest guy but if I shaved I would still have my work cut out for me. Deciding on a whim to go ahead and do as Jamie asked I opened the cabinet to get out my hair clippers.

I shaved the top part of my legs, my small patch of chest hair, my armpits, and as much around my dick and balls as I could with the clippers. Then I stepped into the shower. I used my razor to shave my face and then the parts of my body that I had prepped. The hardest part was shaving my balls and around my ass. It took a long time.

When I stepped out of the shower it felt strange to have almost no body hair. I could feel the cool air on my bare skin and it gave me goose bumps. Putting on some underwear I immediately noticed the difference in how it felt against my skin. I didn't hate it.

After I threw on a t-shirt and shorts I went to the kitchen and grabbed something to eat. I noticed that Jamie's door was closed and I figured that he was also starting to get ready. After eating I turned on the TV and half-watched an old sitcom while I looked at my phone. About an hour later I heard Jamie's door open.

I looked over to see Jamie wrapped in a large towel and wearing a pink wig. I immediately switched pronouns in my head as she smiled and said, "come on in sweetie. It's time to make you look pretty."

I laughed as I got up off the couch and walked over. As I entered Jamie's room I was immediately struck by the amount of feminine clothes on the bed and the plethora of makeup on the dresser. It looked like a teenage girl's room.

Jamie laughed when she saw my face. "Go ahead and take your shirt off and then have a seat," she said as she gestured towards the chair set up in front of the mirror.

I removed my shirt and sat down. Jamie immediately noticed my bare chest and smiled. "You shaved," she said happily.

"Well, someone said it was all part of the experience," I replied playfully.

"You're gonna love it," she said confidently as she ran her fingers through my short hair.

Brushing my hair back Jamie fitting a cap over my head. She then placed a shoulder length black wig on top of that and used some kind of glue to secure it to my scalp. The process took a lot longer than I thought it would.

"What's with the glue?" I asked Jamie at one point. "Can't you just place the wig on my head and call it a day?"

She shook her head. "It will just fall off if I do that," she replied with exasperation. "Trust me, I know." She laughed. "The first guy I ever brought home freaked out when my wig slipped off mid-blowjob."

"Well I don't have to worry about-"

Jamie cut me off. "Just let me handle it sweetie. You'll look good, I promise."

I nodded as Jamie finished and then went to work on my face. She plucked a few stray eyebrow hairs and then began applying makeup. Once she obscured my perpetual five o'clock shadow with something she called concealer, she mostly focused on my eyes and lips. Drawing on them, apply glittery powder, all of which she said would make them look bigger and make my face look more feminine.

It took quite a while but when she was done I looked at myself in the mirror. I was surprised at the result. The changes to my face were subtle but effective. With the long hair and makeup, my whole face appeared thinner and softer than it ever had before. My eyes became the focus as they looked larger and darker. I didn't know if I could actually pass as a woman but I definitely looked more like one.

"Wow, great job," I told Jamie.

She smiled. "I knew you'd make a cute girl," she said. "I just hope the guy I want doesn't want you instead."

I laughed. "You didn't do that good of a job," I teased.

She laughed. "Alright, let's get you dressed."

As I stood up and turned towards the bed Jamie looped the black bra around my chest. I put my arms through the straps as she hooked it together in the back. It felt a little tight but it wasn't uncomfortable. I looked down to see it flat against my chest.

"Here, let's try these," Jamie said as she slid two thin, flesh colored forms into the front pockets of the bra. "I gave you my smallest inserts because big boobs would look weird on your skinny frame."

I nodded and then adjusted them. Cupping the front of the bra I marveled at the way it felt. Soft and pliable yet firm. They felt a lot like real breasts.

"Feeling yourself up already huh?" Jamie teased. "I guess it's true when straight guys say that if they had boobs they would just play with them all day."

I laughed as I reached forward and picked up the black panties off the bed. Suddenly they looked smaller than I remembered and I wondered if they would fit. I began to pull down my shorts and underwear but then I stopped and looked back over my shoulder at Jamie.

Before I could say anything she smiled and said, "go ahead. It's just us girls here."

I barked a laugh as I slipped my shorts and underwear off and stepped into the panties. While I pulled them up Jamie described how I should tuck my dick back to keep it secure. Following her instructions I trapped my cock between my legs and slid the panties up. When I was done I had to admit how nice the soft material felt against my shaved skin.

Jamie then handed me the red, white and black plaid skirt. "This should be tight around your waist and then flare out over your hips," she said. "Your waist is skinny enough that it might even make it look like you have curves."

I stepped into the skirt and slid it up to my waist. Initially I had trouble snapping the buttons together because I was wearing it too low on my hips. Sliding it up a little higher Jamie helped me secure it in place. It was also a little tighter than I expected.

Taking a breath I looked over at her. "Is this what women have to deal with?"

Jamie laughed as she handed me the long sleeve crop top. "Women's fashion is all about sacrifice."

After putting the top on and then the long black socks I turned and looked in the mirror. I had to give Jamie a lot of credit, I looked pretty good. I liked the look of being well covered except for a few strips of exposed skin across my flat stomach and between the socks and the skirt. Overall I was impressed.

"Wow," I said with surprise in my voice. I turned and looked at Jamie. "I look a lot better than I thought was possible."

She smiled at me. "I'm glad you like it." She looked me up and down and said, "I think you look amazing. Tonight is gonna be so fun!"

Stepping over to her bed Jamie quickly removed her towel. I quickly looked away but I got a glimpse of her small shaved cock as she slipped on her own set of panties and bra. A tight yellow dress followed with a wide black belt and then she sat down to do her own makeup.

While Jamie finished getting ready I looked at myself in the mirror again. Jamie was right that the school girl look was cliché but it really seemed to accentuate and highlight my skinny body. My legs looked longer, my torso looked thinner and my bare neck had a more obvious slope to it. No one had ever called me sexy before but perhaps in this outfit it might be possible.

Finally Jamie stood up and unlocked her phone. "Quit staring at yourself," she said. When I quickly stepped away from the mirror she laughed. "Let's take a few pictures and then I'll get us a ride."

Jamie played photographer and had me pose in a bunch of different positions. Sitting, standing, looking back over my shoulder, smiling, serious, even sexy. I couldn't keep a straight face for the last one. After that we took some selfies together. It was actually pretty fun and it ended with us both making goofy faces and laughing.

After that Jamie handed me some shoes and a small purse to match her own. She helped me fill the purse with what I would need: my phone, ID, credit card, keys and some makeup just in case. Slipping on the adjustable flats and then hanging the purse on my shoulder I was ready to go.

Jamie opened an app on her phone and requested a ride. When she was done she turned to me and said, "Ok, the car will be here in five minutes. Shots before we go?"

I smiled. "Yes! I definitely need that if I'm going to go out in public like this."

I got out two shot glass while Jamie grabbed the tequila. She filled up the glasses and then she picked one up. "Last thing before we go," she said with a serious look at me. "What's your girl name?"

I froze as I started to pick up the other shot glass. I actually hadn't given any thought to what female name I was going to use. Staring down at the shot in my hand I racked my brain for a suitable name. For some reason I couldn't come up with anything.

Jamie laughed and then said, "ok, let me help. Who was the hottest girl at your school?"

I thought about it briefly. "There were a few. Natalie and Gwen. Oh, and Ava."

"Do any of those names work?" She asked.

I smiled. "Ava."

She smiled back. "Beautiful. Watch out boys, here come Jamie and Ava." I laughed as she raised her glass. "Cheers!"

By the time our ride arrived I felt a warmth spreading through me from the alcohol. Walking outside I felt the cool night breeze on the top of my exposed legs and across my bare midsection for the first time and I laughed giddily. I still couldn't believe I was actually going.

We hopped in the back seat of the car and greeted the driver. I wasn't sure he spoke English as he just nodded and started driving. Jamie and I chatted together and she took the opportunity to school me in how to act more like a woman: take smaller steps when I walk, close and cross my legs when I sit down, etc. I nodded along but I knew I probably wouldn't remember any of it.

In no time we arrived. The sign over the door said 'T-BAR' in bright red neon lights but otherwise it was a nondescript building in a rather drab business district. Most of the surrounding stores were closed except for the liquor store on the corner. I quickly followed Jamie as she walked towards the large overweight man sitting on a bar stool next to the front door.

"ID," he said with disinterest.

I had a brief moment of trepidation as I handed him my driver's license. What if he questioned me about the disparity between the photo and how I currently looked? But then I remembering that this was a trans bar and he probably saw that all the time. Sure enough he barely glanced at it and in seconds we were past him and into the bar.

As we entered the dimly lit space I looked around. My first impression was that it was exactly like most bars I had been to. Two bartenders stood behind the bar to our left and straight ahead against the back wall was a sizable dance floor. TVs were mounted on the walls and table and chairs were spread throughout.

I was surprised by how crowded it was. Quite a few people were in line at the bar and twenty or so more were on the dance floor. The rest were standing or sitting around tables talking. As I quickly scanned the crowd one thing stood out to me.

A lot of guys were looking at me and Jamie. Most were openly checking us out while a few others were trying to be more discreet. It was a little disconcerting. No one had ever looked at me with obvious lust before and I honestly didn't know how to react. It made me uncomfortable while also being a little flattering.

My gaze was drawn to my right and a long bench along the wall where I noticed lots of women sitting. They were all dressed to the nines: cocktail dresses, short skirts, revealing tops, hair and makeup done expertly. It looked like a fashion show was about to break out.

"Those are the working girls," Jamie whispered into my ear when she saw where I was looking.

"Huh?" I said with confusion.

"The girls sitting along the wall. They are sex workers."

As I processed that information Jamie hooked her arm through mine and began pulling me towards the bar. "Come on," she said excitedly. "Let's get a drink."

As we got in line at the bar I looked at the people around us. Most of the women seemed to be amateurs like me and Jamie. Some of them had clearly put a lot of effort into their looks and it showed. It was a mix in terms of being passable, a few were obviously guys but a lot of others would have definitely fooled me.