The Luckiest Man

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.

By Kim Shaw

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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.

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If you enjoyed reading this feature, you may also be interested in reading the following related features: First Night; High Heels and Shoes.

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