Andy opened the large carrier bag that Tom had dropped off earlier, and dropped the contents onto his bed. He hadn't realised how excited he would be to wear the clothes that he had been given. In the bag were pink panties, pink suspender belt, pink stockings, pick bra, along with a black party dress and handbag. They all looked about the right size for Andy. Until now he had never thought about dressing like this, never dreamt of it, but this looked so exciting. And felt so exciting. Of course he had played with his sister's panties a few times, and with his mother's. But here was a complete sexy outfit for him to wear, out, in town. He was nervous, almost to the point of pulling out, but the excitement was keeping him going. He began to remove his clothes to get changed. This evening he was going to be Andrea, not Andy...............
It had all started a couple of weeks before.
Tom and his best friend Luke worked in the local sports centre. They had been friends of a long time, and people liked them. Both were over six foot, sporty, good looking lads in their mid twenties. Tom had fair hair, Luke black hair. Both muscular. Both played rugby for a local club. They were general workers at the sports centre -- cleaning, manning the reception, sometimes helping in the weights room. They were popular, friendly guys. Both of them had at different times had girlfriends, and there were always girls willing to be with them. Quite a few had been members of the sports centre, and on the odd occasion they had done a threesome together with some kinky hot woman -- generally a married member of the centre who was getting bored with her husband.
Also at the centre was one of the personal trainers -- Bill. Bill was a bit older, always with new ideas, always trying to make an extra penny with some sort of scheme or plan. And he had told Tom and Luke about his latest madcap scheme -- trannyoke! He had seen it mentioned on the internet, and fancied a go at running it. The idea -- hire a bar midweek, have a tranny as host, and do Kareoke! And of course, try to get as many trannies along as possible. Bill wasn't stupid -- he knew several people in the trans community, and thought it was a group he could tap into to make some extra money.
Bill had talked Luke and Tom into coming along for his opening evening. Wednesday evenings were quiet, so Luke and Tom didn't need much convincing. It'd be a good laugh, and if they had a couple of drinks they could sing as badly as the rest of them! Bill sold them the tickets, but then broke the bombshell. "You have to bring a tranny with you." He said it jokingly, and they knew it wasn't essential, but again they thought it would be a good laugh if they could find someone.
Luke and Tom talked about it, and thought about who they could get to dress up for the evening. Brothers were out. Other people at work were out. Friends at the rugby club were out. They needed someone they could ask who wouldn't go and tell everyone if they didn't want to do it.
Then Tom had the suggestion: Andy. His cousin. Luke had met Andy, and knew they had their man. Andy was 19, slim, and had grown his black hair long. He was a student, studying art history. He was friendly, quiet. Maybe he would.......
Tom had asked him, and after a bit of encouragement agreed -- as long as it was just a bit of a laugh. He idolised Tom, and had liked Luke when he had met him. Tom had promised to find the right clothes for Andy, and had scrounged from family members, sisters, friends and got an outfit ready for Andy to wear. He had also got his sister Susie to agree to do some make-up for him as well.
There had just been one odd incident that had set Tom and Luke thinking. They had been looking on the internet for the sort of thing a tranny might wear. They had ended up on a porn site, where two guys were having sex with a tranny, who looked very feminine in clothes and make-up. On the surface they had laughed at it, but Tom had jerked off later imagining it was him and Luke having sex with the tranny. Luke had also found the video a turn on, and had even given a hint when he said to Tom jokingly: "we'll have to give that a go one day.......," the comment seeming to pass quickly.
The day came, the evening after work for Tom and Luke, after college for Andy. Tom and Luke felt excited, but not as excited as Andy.
So Andy removed his clothes and began to dress himself. He put on the pink lacy panties -- they were a bit of a stretch over his cock, but he felt comfortable when they were on properly. It took a few minutes to get the stockings and suspender straps right. He wasn't sure whether they should inside or outside the panties. He settled for inside. He put on the bra -- it was tight, but it was okay. He put on the dress, found the zip difficult but managed to do it up. He had insisted on flat shoes -- and they had found a pair of black slip on female sandals. He looked at himself in a mirror and thought he didn't look much like a woman.
Susie came, and did his make-up. Bright red lipstick. Eye-liner. Other powders and creams he didn't understand. He looked in the mirror and there was someone who could be a woman looking out at him. Susie had been very encouraging that he looked amazing. She left -- he still had half an hour before Tom and Luke were going to collect him.
It was about nine when Luke and Tom had turned up. When they saw Andy -- Andrea as he now called himself, and told Tom and Luke to call him -- Tom smiled, Luke wolf-whistled. Neither has come across a tranny before, and here was a really hot shemale in front of them. Of at least -- Andy dressed as a woman, and looking very sexy.
When they arrived at the pub there were already several people there, including a number of men gorgeously dressed. Andrea thought he looked as good as any. He -- no, she was really nervous, walking into a public space dressed so sexily. The three headed towards a table with a corner bench. They got Andrea to sit in the corner on the bench and Luke sat next to her. Tom got some drinks in, then Bill came over with a couple of friends and sat at the table as well. It was when one of them looked at Andrea, smiled, and said "mmmm, you're a sexy little minx," that Andrea felt worst, or best. She went bright red, and demurely turned to the side. It was then that Tom returned with the drinks and sat the other side of Andrea from Luke.
Bill's friend -- Andrea quickly learnt he was called Tony - turned to Tom and spoke. "You didn't tell me you knew such a hot little cow as this one here."
