The Luckiest Man

The Luckiest Man

I couldn’t believe it! The lights came on and Jen grinned mischievously at me and threatened to pull my wig off. Jen and Andrea were loving this. I was loving this but I was as scared as I could be.

This is not a work of fiction, this is a true story. One of those true stories that when you read it, it must be a work of fiction; the sort of fiction that comes under the heading Transvestite stories: fiction.

I was in a club in Brighton, near the pier, popular with not so serious clubbers, but an ordinary club all the same, open from 8:00 till 2:00am and I was in it sometime after nine with Jen and Andrea and I was completely dressed up and having the bizarrest and most exhilarating evening I had ever had.

It started like this. I’m 32 and married to a fantastic wife who is more or less tolerant of the fact I like to dress as a woman. Well, it was her birthday party and we were having a great laugh with loads of mates and I was chatting and having a laugh and circulating and found myself sitting next to our next door neighbour Jen and her friend Andrea. Jen and Andrea are great fun and up for anything and I’m not sure how we got round to it but suddenly and without my prompting I’m being invited out on a girl’s night out with Jen and Andrea dressed as a girl. “Go on, I dare you!” she chided in her Cardiff accent.

What! She can’t possibly know, can she? I’m paranoid, like most men I imagine, about letting it slip, about being found out, but how could she know? She can’t have. Andrea can’t have. But here is a plate put in front of me and a fantastic chance lay upon it.

In front of me. Asking to be snapped up. How could a girl refuse?

This was a Saturday and I had to wait for the following Friday and the week was agony under the weight of expectation tempered with the thought of the crushing disappointment if it didn’t happen. The wife? Oh yeah, Well I had to ask her permission and she knew that it was something I wanted to do so “Don’t worry, I’ll baby sit for Jen so you can go out.” In fact, she bought me some stockings and made the lovely, sexy and elegant elbow length gloves with a feather trim that I was pulling over my shaking hands as I got dressed in Jen’s bedroom the following Friday.

I had gone round there desperately trying to hide my enthusiasm and exploding Joy and Jen said “right then,”, upstairs, use my room and I’ll get you made up when you come down.” Gulp. No ceremony. No do you want to wimp out just go upstairs and get dressed!

So now I am walking tentatively down her stairs wearing a slightly tarty but dangerous outfit. First I had put in the black shiny bra that fitted very snugly and with a little padding gave a good representation of breasts, then very feminine cream suspenders with little frills and bows on. These were attached to the fresh black stockings that seemed painted on my legs and stopped the regulation distance from frilly, teasingly smooth black knickers that held me in place and felt so amazingly sexy. If they saw these then they’d know.



I put on the animal print top and then from my bag a dangerously short skirt that only just covered the stocking tops. I couldn’t believe this. I was about to walk down stairs and face two whistling, laughing women wearing the sort of clothes that had never left the safety of my house and present myself to them. The last touches were some Pat Butcher like jewellery and a pair of Lady DI high heels – a genuine mix of cheap tat and expensive shoes.

Their faces when I opened the door and tottered in were a picture – both Jen and Andrea were screaming with laughter as they sat me down and teased me and admired, jealously in Andrea’s case, my legs. They didn’t shave them, luckily I’m fair haired, but they did go to work on my face and cover me with silky foundation and lashings of mascara, lipstick, eye shadow etc. They were having more fun that I was. Finally the long blond wig I had brought from Transformation was placed on my head and arranged to look deliciously feminine and an overly generous spray of perfume was aimed at me and then I was ready. Ready for a night out with no keys, my money handed over, no male clothes, no surrender, total reliance on my two friends (why do women seem to love humiliating and titillating men like this) and no way home until they said so.


Who ever has been out for a walk dressed up will know that stomach knotting feeling of apprehension, especially when the seconds drag by as someone walks towards you, or drives past, but suddenly, no matter how “interesting” I looked no one was really paying me much attention. There was no way that I could be 100% disguised but people just weren’t paying me any attention – at least not to my face. The British sense of reserve is a wonderful thing.

And then before I really knew it the short drive was over and we were in the queue to get into the club, chatting and Joking and still no one seemed to pay me much attention and then I was paying for my entrance ticket and then walking into the bar and then “Well, hello there!”

The DJ had spotted me, oh yes, and to him I was a perfect target. “Look at the gorgeous girl who’s just walked in.” Ok, it’s roughly half eight and the place only had about a hundred people in it but that’s 200 hundred eyes staring at me. Oh my God. The fear instantly rose. There was a big bunch of guys at the bar already getting drunk. I expected to get through the night relatively unscathed but this could go anywhere.

Jen seized the moment perfectly and went up to him and said I had lost a bet on the England – Argentina World Cup football match and this was my punishment (if only you knew Jen, If only you knew.) an then the DJ got really mischievous – as did Jen as she conspired to win me a bottle of champagne from the DJ if I danced on the stage with her – IN FRONT OF EVERYONE. The wind from the smoke machine nearly raised the skirt to new heights as I was paraded on the stage and made to dance with Jen as

Andrea took photograph after photograph. It was then that the fire alarm went off and Jen decided that now might be a good time to pull my wig off. Jen! People from my work come to this place! But she resisted the temptation and I got my bottle of champers – but we could hardly drink it for laughing so much. Any tension I had left disappeared as the alcohol flowed and from then on it was non stop and I was on the dance floor, in the ladies toilet (when I needed to pee), in the arms of a Thai girl who thought I was very sexy (this is all true), back on stage with a hen night from Rayleigh, getting chatted up by a very excited gay bloke, dancing with Jen and Andrea and some other girls, having more make up and perfume applied and then, finally being allowed to relax and sit down with a more manly pint of beer at some time around 1:30 and then “I’m starving. Let’s go to the local store and get some food.” Said Jen.

This was getting bizarre and bizarrer still! By two thirty we were walking round the 24 hr store in Brighton in and out of the aisles while Jen looks for cheese and onion pasties and Andrea for some sandwiches and then having negotiated the giggling girl on the till who could only just find the composure to scan the items we had bought, I had to sit with the girls in full view of the late night shoppers while they sat and ate them. What a night for the staff of the store!

All the time, I was made to feel like a princess, but a naughty one who had to do what her wicked aunts demanded.


Finally, closer to three, I was dropped off home and we sat and giggled and laughed and recounted what an amazing night it was. If it were transvestite fiction I imagine this would be where the kinky sex scene would be put but there was none of that. Just a gentle end to a thrilling night.

My wife was so happy to see me home unmolested and un-beaten-up but she thought the whole thing was hilarious and wants to come out again next time. They’ll definitely be a next time, but maybe not to that club again.

Kim Shaw.

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