Crossdressing a Life - Sex Stories

Crossdressing a Life

All characters in sexual situations are 18 years of age and older.

I am a 62-year-old lifelong crossdresser, I use various internet sites and I have told snippets of my story here and there, so I thought I would write them all in one place.

I joined the military, we used to go as a group to the base swimming pool and muck about. There were some Jordanian students there at the same time, they used to mess about with us in the pool, climbing on our backs and pushing us under. One of them took a shine to me and would always single me out, all of this was going on between friends at a time when homosexuality was still illegal in the military. One day my friend climbed on my back, and I realised his cock wasn't in his trunks, so as he pushed me under, I took his cock in my mouth it was only for a second, but I loved it, nothing else happened and although I saw him at the pool again, that was that. I did fantasise about what may have been.

Life moved on as normal until I met a girl who would become my wife. I told he of my love of nylons and one night as we left the pub, she slowly lifted her skirt and revealed she was wearing a white suspender belt and tan stockings, I was hooked. We used to meet in my room for sex and one night she brought two sets of stockings and suspenders we wore a set each and made love all night.

Once we were married, she would indulge my habit and on occasion would dress me then make my face up in full make up and put a wig on me. She didn't ...

... mind me dressing but, said that when I was in make-up and a wig I looked like my mother, and she did not like that. So, the make-up and wig just sort of stopped. We spent a few years dressing up for each other, but once she put some weight on, she was not keen on dressing-up herself.

When I discovered the internet everything changed. I still dressed for my wife, but I started chatting to other dressers online.

My first ever meet was with a gurl called Zoe, we chatted online for some time, she said I needed a girl's name, so I suggested she choose one for me and so Tiffany was born. Our first meet was a weekday lunch time, we met in a garden centre care park, chatted briefly, then I followed her to a remote location. Once there I got in her car, and we kissed. We both pulled down our trousers, Zoe was wearing Black Fishnet Stockings with sexy red panties under slacks and a dress shirt, I had on hold up stockings and sexy panties. We kissed and Zoe went straight for my cock, she sucked me so well, when I returned the favour Zoe had a fat cock with a large bulbous head, but the most surprising thing for me was her pre-come, there was loads, she was so wet, I licked it all up then sucked her to orgasm, she then returned to sucking me.

My second meet was with a lady called Pauline. Pauline was in her late sixties and lived in Newcastle. We chatted for a while and exchanged pictures. Pauline was a very tall slim elegant lady, who used to visit with a group of ladies in ...