First Time

I have been a closet cross dresser for years and have often thought about being with a guy while dressed. I had to go out of town on business and I took my girl things with me. I got all dressed up in a short dress, five inch heels, garter belt, panties, bra with silicone breast forms, wig, and make up. I put an ad on a list and chatted with a guy for a bit. I asked him if he wanted to come to my hotel room and he did. When he got there, he called me a sissy and told me to get on my knees. I did and had my first time with a guy. I loved it and have done it a number of times since. Someday, I want to get all dressed up and go out on a date with a guy.

— Martin, 57

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