Crossdressing a Life - Sex Stories

Crossdressing a Life

... He was a big man slightly overweight with a big belly and barrel chest. I walked straight up to him and kissed him; he kissed me back and we both started exploring each other's bodies. I sucked his nipples and then knelt on the floor and sucked his big fat cock. He led me to his bedroom, and I lay on my belly so he could spank me, then he lay on the bed, and I sucked him to completion.

One day I was bored, I was wearing stockings and panties under my jeans and decided to look for a cottage. I stopped at some toilets north of Amble and went in to pretend to have a piss. There was a chap inside who asked me if I wanted some fun. I agreed and we went behind the toilet block. We kissed then both dropped our trousers, he did not comment on my choice of underwear, just proceeded to give me a wonderful blow job, when I came in his mouth, he just spat my come onto the floor. He then asked me to wank him, I offered to blow him, but he said no. So, I then wanked him off and pointed his come to land where he had spat mine. Afterwards he told me he was not into the crossdressing thing but went ahead with our meet as he was so horny.

I started to correspond with a crossdresser in Ashington called Davina, we seemed to hit it off. A meet was arranged at her home. When I arrived, Davina was fully dressed and made up. She looked sexy. I was introduced to Davina's wife and after a brief chat I was shown into the downstairs bathroom so I could change, I had girly undies on under my male ...

... clothes, so I changed into a miniskirt and frilly white blouse. When I returned to the living room, Davina just said "wow" then her wife very kindly told me I looked very nice.

Davina kissed me and asked if I was ready to go upstairs.

Once upstairs we got straight to it, Davina had told me in our correspondence that once she got going, she went at it like a steam train. We made love to each other I fucked her first, then she fucked me. Davina wasn't wrong, she fucked me on my back then doggy style, I had never experienced anything like it before, she was so good though.

I was left in no doubt that I had been fucked.

We went back to the living room and chatted, then I changed, and it wasn't until later that Davina informed me, I had left my white frilly blouse on the back of her bathroom door. I should have gone back for a return meet, but the opportunity never arose.

I then met another admirer called bear. He liked to meet outdoors, so we met in a church yard. I had my now usual choice of underwear on, and we met at the agreed time we had a long kiss and a cuddle before giving each other a lovely blow job. He even showed me around a nearby cottage.

Then I went for another visit to Jeans. This time I asked if she minded me wearing stockings during my visit, she assured me this would be fine. Upon arrival I was shown into her massage room and stripped down to my black hold up stockings.

Jean came in and was again wearing hold up stockings and panties, she ...