A Night Out To Remember

A night out with Liz and Sue

I had known Sue for almost five years but had known Liz for a lot longer. We had met while she was still at school although I was four years older we still became good friends. After she left school I helped her with her college work and more importantly when she needed advice about boys and later girls. I helped her pass through that difficult stage when she was just discovering her sexuality. She soon became aware that although she liked boys she liked girls a whole lot more.

It was difficult because we lived in a small country town and everyone knew everyone else. She even lived with me for 6 months while she was trying to get a job. As she became more confident about her sexuality I started going with her to the big town 20 miles away where my parents still lived. We would go for a few drinks in the town centre bars and she would beg me to take her to one of the few gay bars. I went but would just sit back quietly drinking my beer while she would dance and chat with the people who were there.

Sometimes a guy would come over and ask me to dance or offer me a beer but I would just politely refuse and say "sorry I'm straight, I'm here with my friend." Most of the guys would apologize for bothering me and some would sit and chat for a while before going to look for someone else. I enjoyed the gay scene as everyone was friendly and there were never any problems.

It was in one of these bar where Liz met Sue and they hit it off straight away. They were like chalk and cheese, Liz is tall and well built with beautiful 36C tits and full hips. Sue was a lot shorter and slimmer with pert but small 34B tits. That was five years ago next Saturday and they were planning a big anniversary party.

During the last five years Liz had got a very good job in a big city about 60 miles away and Sue moved down with her and had found a job nursing in the local hospital. I had kept my old engineering job but had promised to go down and celebrate with them even promising I would be there whatever it took to do it.

Typically on Saturday morning, I had to work on a rush job that took longer to do than it should so had to ride down on the afternoon. I had been riding my motorbikes since I left school and now had a big fast bike so the 60 miles was no problem. No problem turned out to be "famous last words", I had barely got half way before it started to rain, one of those summer storms that last half an hour but dump enough water to swim in and I didn't bring my waterproofs. Then the ignition started to break down on the bike and by the time I had got the bike running again I was soaked.

I finally got to Liz and Sue's house a little after five and the party was supposed to start at seven. I opened my bag to get my party clothes out and to my horror found they were soaked too. Even worse everything was stained with mud and oil off the road. The only thing that wasn't wet was an old pair of shorts I had intended to use to sleep in.

Liz had planned to go to a gay nightclub after meeting her friends in the gay bar but it was a slightly up-market place and had a dress code on a Saturday and an old pair of oily jeans just weren't good enough. I said I would stay at her house while she went out with her friends but she wouldn't go out without her best and oldest friend with her. I wasn't going to let her stay in on her and Sue's fifth anniversary so there had to be a way for me to go with them.

My clothes were ruined and I needed to be reasonably well dressed to get in the nightclub. I said I didn't want to spoil her night out and would do anything to help. These were foolish words to say to Liz who had a sense of humour with a wicked edge to it. We already knew she could fit many of my clothes because she had borrowed most of them when she lived with me. A pair of jeans was no good as the dress code didn't allow them so we needed a decent pair of pants that didn't look too feminine. The same went for T-shirts, a nice shirt looking blouse would be ok.

We looked in her wardrobe and found nothing. There were lots of very feminine dresses and skirts, a few frilly blouses and little tops but nothing that could be mistaken for anything other than women's clothing. Sue's clothes were the same mixture of delicate girly tops and skirts. I was starting to lose interest in the whole idea when Liz obviously came up with a plan.

"If you don't mind wearing some of my clothes to go out then you shouldn't mind wearing any of my clothes." She said in a questioning tone.

"Well, I don't know, what do you have in mind?" I asked slightly confused by this sudden change in direction.

"You know I love you and would do anything for you." she said and now I was starting to worry about what she was thinking. She didn't normally begin by saying that unless she was going to ask me to do something she knew I wouldn't like. "Well you know we will go to the club and there are lots of weird people there so you wouldn't look unusual or strange. So I was thinking you could dress up and make it a kind of fancy dress party." I still wasn't sure what she meant but the alarm bells were starting to ring. "You know we are about the same size and almost everything in my wardrobe would fit you. With a bit of make up we could go as a drag queen or something."

Now I was worried because I had already agreed to try on her clothes if there was any that was suitable and she had just made everything suitable. No matter how hard I tried to back out the two girls wouldn't let me.

"Come on, I would do it for you." Liz said in that tone that suggested I would have to find a really good excuse to get out of it. I didn't want to spoil their evening so I finally agreed.

First I had to get a shower and shave as I didn't what to look like a butch dyke as the girls put it. Liz said that while I got my shower they would find some suitable clothes. Then after I got dressed they would then finish with a little bit of make up. It all sounded so simple and painless but I was still not happy about being dressed as a woman in public.

The shower felt good after the long afternoon spent getting here and shaving my legs wasn't much more difficult than shaving my face. I didn't have that much other body hair but the girls insisted I shaved it too. The feeling of being completely hairless was a little exciting and now that I had started the rest of the plan didn't seem so bad.

The two girls had laid out a range of clothes for me to try. They decided that black was just too cliché and same went for white so it was a choice between the pink or pastel blue underwear. I liked the blue lace bra and panties set as the panties looked more comfortable than the pink thong and half-cup bra. The panties were more snug than I expected and when I tucked my cock between my legs and pulled them up, I found they held my cock in place, perfectly. The lacy front meant you could see my pubes but nothing else. The bra fitted nicely around my chest but because it was Liz's there was a lot of space in the cups I couldn't fill. Then Sue surprised me by giving me a pair of false tits.

"I like to pretend mine the same the size as hers when we go clubbing." She explained. Now the bra fitted perfect and the little panties hugged my ass very tightly. Next, came the stockings which were holdup style and flesh coloured with a nice lacy edge around the top. Standing there in just the bra, panties and stockings made me feel quite sexy but not ready to go out.

They did my makeup with just a little eye shadow and mascara around my eyes, a bit of blusher on my cheeks and deep red lipstick. They even painted my nails a bright red before they took me out of the bathroom back into the bedroom. The skirts they had picked out were in various shades of red, blue or yellow. Each one was short and tight fitting and after seeing Liz wearing them I knew they left little to the imagination. I wasn't sure I had the right figure to wear anything that short or tight. Liz then showed me a pale blue skirt that was cut at an angle so that it was longer on the right than the left that would swing and flow as I walked but Liz warned me that it was quite light and could blow up if I wasn't careful. I picked that skirt as it looked easier to walk in even though it showed most of my legs and barely covered the top of my stocking that my left leg was wrapped in.

I now needed a top to match the skirt and Sue said she had the perfect thing. The skirt had a very tight matching camisole top which was difficult for me to put on over the suddenly larger chest the bra and fake boobs gave me. It wasn't a very warm night so they gave me a short white silk jacket that only just reached the top of the skirt. Looking down over the top of my tits I could see my feet and nothing much in between without leaning forward.

They seemed happy with my choices although they wouldn't let me see myself in a mirror until they had finished the transformation. I was shown to a chair for my makeup and again Sue surprised me by bringing out a long brown wig.

"Sometimes we go out as twins." She explained to my unvoiced question.

"Oh, yes lets do that." Squealed, Liz in delight. "We can all go dressed nearly the same as each other and see what everyone says. We'll look like triplets."

"I'll go in the red skirt and you can go in the white one." Sue said in the same girlish voice. I hadn't heard them this excited for months and I didn't feel as bad as I stood there in a pale blue skirt, camisole, short white jacket, stockings and blue bra and panties set. They reappeared a few minutes later and they did look like sisters in their red and white skirts and matching tight tops, it didn't occur to me that might look the same as them. Liz found me a pair of not too high heeled shoes that "shouldn't hurt my feet too much" or so she said. They did their makeup and we were ready to go.

"Wait a minute I haven't seen myself yet, I want to know how bad I look." I had expected to look like someone out with friends in fancy dress but when I saw myself the impression I got was very different. I didn't want to look like a drag queen but the beautiful woman that stood in the mirror where I should have been was a real shock. I wasn't sure if this was a good idea because as a man in fancy dress nobody would chat me up but dressed like this I might try to chat myself up if it wasn't me. I was confused I just didn't expect to look this good.

Liz and Sue dragged me out and hailed a taxi before I could think too much about what I was doing. I was in a straight bar having my first stiff drink before I realised I looked like one of three girls. All of us were getting looks off the guys in the bar but fortunately Liz finished her drink quickly and wanted to go to the next bar.

Four bars later and we finally arrived at the gay bar where we were meeting Liz and Sue's friends. I knew many of them as I had met most of them a few times over the last five years but none of them recognised me dressed like this. Liz introduced me as Jane a friend from school that was down from the old hometown for the night. So far the night had been a blur and now that we finally slowed down I could start to get my wits back. I was dressed as a beautiful woman in a gay bar miles from where I lived and everyone here seemed to think I was a school friend of Liz, a female friend of hers.

I then found my first unexpected problem when one of her pretty but very gay friends asked if I wanted to dance. Should I say I am gay or straight? When I was a man there was no problem because only the gay guys would hit on me but now I might get hit on by the lesbians or the various straight guys that always seemed to be there. I decided to be the opposite of whatever they were and try to everyone happy but at a distance.

My plan was working up until I met Garry. He had come with one of Liz's friends but had come late because he lived a short distance from the city in one of the small villages nearby. We were introduced by his sister who had been friends with Liz for years. I knew she was a lesbian so I had already told her that I wasn't gay to keep her from hitting on me but she now told her brother that I was straight.

He was nice looking and a little taller than me but he just chatted about simple things and never seemed to be trying to anything more. I had stopped drinking the hard stuff in favour of beer but only in half pint glasses and even then only very slowly, taking little sips instead of big mouthfuls. I was starting to like the handsome young man with his quick wit and pleasant conversation.

It was soon time to go to the nightclub and so we all gathered our things and for the first time I headed to the "little girl's room" with all the other women. Liz and Sue rushed over to me and whispered,

"We saw you talking with Garry and you were flirting with him!" I probably blushed but still denied everything. They giggled and said "of course you weren't" in a tone that said "yes you were." We got into the nightclub without any problems and Garry even paid for me. I found myself sitting in a quiet area of the club with Garry while everyone else went to dance. When he asked me to dance, I said yes without thinking, although, I may have thought it was a mistake if I had allowed myself to think too much at this point.

We danced for awhile and I found myself enjoying being treated like a girl but it still felt a little strange when I looked up and saw a guy instead of a girl as my dance partner. I could feel the dress move over my legs as I slowly danced to the music. I even started to admit to myself that it felt really good to feel so many things moving with me, my dress swished around my legs, the camisole was very tight but I could still feel the false boobs moving underneath it. I could feel the long hair of the wig swirling around my shoulders and the dangly earrings which Sue had insisted I wear, moved with the music.

I can't remember what music was playing but I do remember looking at his feet most of the time as I thought that was the proper thing to do for a girl and only very occasionally looking up at his body. Each time I caught myself looking at his strong legs or broad chest I would remind myself that he thought I was a girl and lower my gaze back to his feet. As we danced I found that I had to remind myself more often and even sometimes I caught myself looking at the bulge in his pants. What was I doing and what was I thinking looking at a man like that.

I couldn't believe I was standing there dressed as a girl dancing with a man and looking at his crotch. How did this evening get so out of hand? Then the music changed from the fast dance music that was popular in the clubs and bars to a slower romantic ballad style. I thought that it was time to go back to our drinks and chat some more but Garry simply took my hand and pulled me close to his chest. I surprised myself by not resisting and suddenly found myself pressed gently to his warm strong body. As we danced I became more comfortable with the situation and even started to enjoy it As we swayed to the music he moved a little closer and I even leaned towards him and it was then I felt something I definitely did not expect to feel pressing against my belly. It was his cock and although it was soft it still felt a lot bigger than I thought it would feel. I realised that I had actually thought about how big his cock was when I had looked at his crotch earlier and how it would feel pressed against me. I tried to pull away slightly but found I didn't want to. I liked the feel of this man's body and wanted to stay there for a little longer. I felt warm and safe even though I knew he thought I was someone else or at least something other than a man dressed in a pale blue dress and lace panties.

The song changed and in that moment as one finished and next began, he lowered his head and I looked up and our lips met. It was a tentative kiss at first but when I didn't pull away the kiss became more romantic and then passionate. I didn't want it to begin and had been dreading the awkward moment when he would try but that was before the slow dance and now I didn't want it to end. We kissed for what seemed like forever but it was only a few moments. The kiss had a strange effect on me and I seemed to melt in his arms, the effect on him was probably predictable but it still took my breath away. I felt his cock start to grow in his pants and push more against my panty covered skin just above where my cock was being held captive between my legs. I was very conscious of the slow movements as his cock began to wake from its slumber. Each heartbeat made it harden a little more, my heartbeat increased with each little twitch of that long piece of flesh I had not seen but was getting to know better as it continued to press against me. I was getting excited at the idea that I had made him excited and that his excitement was sexual as well. I had a funny feeling in the pit of my stomach and the hairs on my arms had they still been there would have stood on end. I'm sure I was blushing and I was definitely feeling a bit warm as the bulge kept getting bigger.

A question popped into my head, "could I actually fancy this guy, did I find him attractive? What would I do if he wanted to take this further as his cock told me he was thinking of doing?" it was now hard and pressed against leaving little doubt that the kiss had given him the desire to go further than the goodnight peck I had been willing to give just a few minutes earlier. Now I was actually thinking about a much longer kiss that I hoped would be just moments away but once again the music changed back to the faster dance stuff they had played earlier and we decided to sit back down.

I guess from Liz's expression that see had seen me on the dance floor and was shocked at my behaviour but I didn't care as it was her fault I was dressed like this but as I turned the corner of the bar I saw myself in one of the many mirrors that covered the walls. My dress and camisole were almost transparent in the UV lights that had been switched on during the slow music. My bra and panties were clearly visible through the dress luckily the bra and panties were not effected by the lights and remained opaque despite being almost nothing but lace. My figure looked even better than before, my tits and my ass were fantastic and I did look very sexy. Suddenly I felt so sexy and desirable that Garry would be a lucky man if he could have me but if he asked, I would have done whatever he wanted.

I was so horny that I wanted to see that bulge instead of feeling it through his pants and touch it with my hands not just have it pressed against my stomach. He said he was going to the toilet and I sat down next to the girls and I took a sip of my drink before being dragged off to the ladies by Liz and Sue.

"What are you doing?" asked Liz with a smile, "I think you more than fancy him. I think you want to find a quiet place to...." She left the last few words hang in the air without saying them and she was right, I did.

"I thought you were straight." Sue added to an already confused situation. "And I thought he was straight too."

"Yes I know, this is going to be a disaster no matter how I do it." I moaned as the reality of it all come rushing back to me. I looked into the mirror on the wall and saw a beautiful young woman with firm breasts and a tight waist but below that I knew was a cock that wasn't going to disappear for a few hours and make everything easier. Even as I thought this I was still remembering the feel of his cock and I even tried to picture the size and shape of it. The harder I tried not to think about it the worse it got.

We left the toilets and went to sit back in our seats just as Garry came back from the bar with fresh drinks. Instead of sitting opposite me as he had been before, he sat next to me. He gave everyone their drinks and handed mine to me with a smile that had me blushing again. As we chatted I felt his hand brush my leg a few times before it settled just above my knee. Garry was sitting on my left and the skirt had slid up and was an inch or two above where his hand was. He moved in his seat to face me a little more and as he did his hand moved more than the two inches to the hem of my dress. The feel of his hand moving over the stockings was electric and when it reached the bare skin above the lace trim at the top I almost forgot what he would find in place of the cunt he was expecting to find. I almost didn't stop his hand in time but finally put my hand on his before it was too late and said, "Not here." I knew I should have something like NO, stop it, don't do that or something more definite and less vague than not here but that's what came out of my mouth.