Crossdressing a Life - Sex Stories

Crossdressing a Life

... proceeded to massage me from head to toe. Having my legs massaged whilst wearing my stocking was a wonderful feeling. Jean then massaged my prostate whilst wanking my cock, I had a lovely finish.

I then moved to Swindon where I continued to look for other crossdressers, I had two meets with an older crossdresser, both were alright, but I was feeling under the weather at our first meet and only managed a blow job. Then at our second meet he was unwell, so we both dressed at just sat and chatted, I quite enjoyed a relaxed evening.

I then visited Swindon's Gay Sauna, the first time I went there were lots of gay men there, I watched some gay porn then watched a threesome with three young men. I met a crossdresser who was in a separate room on all fours. She had a big dildo in her and her balls were tied tightly with a thick nylon rope. As I fucked her with the dildo, she asked me to pull on the rope hanging from her balls, I did this, but she wanted the rope pulling much harder, I could not believe the pain she was letting me inflict on her.

On my second visit to Touch there was a good-looking man in the sex sling being fucked by a much older, but very well-built gentleman. As he reamed this man I watched and was totally turned on. Then I noticed the man in the sling had painted toenails, I was intrigued. When the fucking was over, I approached the man in the sling and mentioned his nails. He said he was sissy but did not like dressing for the sauna. We went into a ...

... private room and kissed. I lay on the bench, and he sucked my cock and played with my nipples, when I came in his mouth he just got up and left me, alone.

My next meet was with an escort who was a professional master.

We chatted briefly, then I asked sir for a meet. Master was in his sixties but still very handsome and was happy to meet me.

I arrived at sir's house early and was shown into the living room, we chatted and established my limits, I wanted to be punished but left unmarked.

Master said he understood, I was told to undress and wait for him, Master put a DVD on for me, it was a gay film with a twink in a public-school uniform being punished by an older man. Not my usual choice of porn, but it still turned me on. When master returned, he was stark naked, he had a lovely slim body with a fat semi hard cock. Master kissed me and played with my nipples. Then I was bent over the back of an armchair and punished with various implements, just to establish my pain threshold.

Master was very tactile, sliding his hands all over my body.

Then he knelt behind me and began to rim my boy hole, the feeling was unbelievable, I thought I was going to come right there. Then Master stood up and spanked me hard.

Following the spanking he placed a finger into me and fingered me so nicely I was moaning like a girl.

He followed his fingers with a sex toy, the feeling just got better and better.

The toy was removed, and he slowly pushed his cock into me, I was being ...