Crossdressing a Life - Sex Stories

Crossdressing a Life

... times and we always had fun with each other.

After Kirsty I met my first admirer a lovely kind man who I have written about in the story My First Real Man.

Next, I chatted with a girl named Jenn, as neither of us could accommodate we arranged a car meet. We drove around for hours trying to find a secluded spot, finally we found one. I joined her in her car as soon as I had her cock in my mouth a police car came around the corner and we both got spooked and said our farewells. Not at all how I wanted the meet to go.

I sort of gave up on meeting after that. Until I was contacted by Carol. Carol was an older lady who was a widower but still had all her wife's clothes. In all her pictures she was wearing rather old fashioned but immaculate clothes. We met at her bungalow near York. After I changed, we were both fully dressed, Carol had net curtains up in all the rooms, so she left the curtains open. We were sat in her bedroom looking at sissy porn, when a lady postman knocked on the front door, which was right outside her bedroom window.

I don't know if it is common knowledge, but when you stand close to a window with net curtains you can see right into the room.

We both froze, I was panicking like mad, then Carol started to fondle my bottom. So, there we are two older transvestites stood about three feet away from a woman in her forties and I am being groped by a woman who should know better.

He asked me if before I left would I come on his cock and just pull ...

... his panties up, so after he had given me a blow job, that's exactly what I did, I wanked over his cock, pulled up his panties and told him to keep them on until the morning. I then changed into male mode and left.

I moved around a lot with work, I was living in Wales when I contacted a gurl called Lynda, she was in her mid-sixties and a very sexy gurl. Lynda informed me she had a boyfriend who visited her about once a month for sex and they had agreed that her boy pussy was his only, so anal sex was not on the menu, I agreed not to ask for anal which she thanked me for being so understanding.

We arranged to a meet at her place, I showered and was dressed in some sexy undies under my male clothes. On my way to Lynda's, I stopped at Tesco and bought myself a new silk blouse, a bottle wine, and some flowers.

I knocked on Lynda's door and when it opened there stood a full-figured lady dressed in a miniskirt and pink blouse, she had such a sexy smile. I stepped through the door and Lynda immediately kissed me. I gave her the flowers and wine and we chatted, then I went upstairs and changed into a miniskirt and my new blouse, I went downstairs, and Lynda just said "wow". We sat and ate a light meal together; I could not keep my eyes off this older sexy lady.

Once the meal was over, I caressed Lynda's nylon clad legs, I then stood over her and played with her nipples whilst we kissed.

We then moved to the sofa where we sat facing each other and continued kissing, I ...