My first adventures as a transvestite Sex Stories for free – Y2 Stories

When I discoved the pleasures of having sex dressed as a woman.

One day when I was 17 or 19, a man who had picked me up and taken me to his home asked me to undress then handed me one of his wife’s dresses and a wig. He wanted to fuck me dressed as his wife. I saw no problem with that, so I did what he asked. We went into his bedroom and stripped off himself. I took his reasonably sized cock in my mouth and started sucking it. He told me to get on my belly, and he climbed on top and pushed his cock up me un-lubricated. He then spent the next 15 minutes buggering me as hard and rough as he could, grabbing parts of my body and making them bruise, hurting me as much as he could. I realised that what he was doing was giving me a hate-fuck in place of his wife.

When he finished, he asked me for the dress and wig back, and I got dressed and left. Later that night I contemplated how getting fucked dressed as a woman made me feel. I had sucked and been fucked by hundreds of men by then, but being dressed as a woman added an added frisson to it. In the following weeks I acquired a few dresses from a charity shop, a wig, and some basic make-up. Despite being very nervous I started taking walks in the neighbourhood dressed as a woman. It was interesting; sometimes when I was walking a car would beep it’s horn and I would pretend not to hear it and turn down a side street. What I got out of it was a form of exhibitionism. It was great.

I still went out most evenings to the cruising spots and public toilets, where I would never be short of men wanting to use me. A few times I wore a dress and wig, but most men wanted to strip me naked and bugger me as usual, so I gave up going there in drag. My transvestite adventures were shelved until some year later.