Having this urge to crossdress was always a conflict. I knew that it was wrong (I had been told) but I couldn't help my desire to do it. It was a difficult age with hormones all over the place and still a child but becoming a man.
I can remember I had a cuddly toy on my bed. It was old and falling to bits but I used it to keep a pair of knickers in. At night I could take them out and wear them in bed. Still a child but sexually aware.
All sorts of contradictions were going through my head. If I wanted to dress as a woman I must be gay. But I didn't fancy other boys. Nobody to talk to or ask. I used to say to myself if I didn't get a girl friend then I must be gay. But I was paralysed by shyness which stopped me talking to girls. All the time I'm longing to be close to a girl and little did I realise that my crossdressing was a substitute for a girl friend. I was my own girl friend!
After I left school and started working my life changed.
I made some good friends and sport and alcohol took over. But also women!
In comparison to my peers I was probably late in losing my virginity. I was 18. I desperately wanted to but it meant getting a girl friend. I still found it difficult to talk to women I fancied but my crossdressing had waned.
I lost my virginity on an 18 to 30 holiday (that ages me lol). A girl sort of attached herself to me and well, the rest is history. God it was so good.
Through my 20s I had quite a few girl friends. Some of them married! In each case they did the running. I can only remember plucking up the courage to ask one girl out and that was at a night club after being given every signal she was interested. I had enough sex to keep me happy and my crossdressing stopped altogether. Reflecting on it I still found how some girls looked erotic but I didn't wear any women's clothes.
Sex was nearly always instigated by the woman. I always considered myself respectful and would never force myself on a girl. It had to be her choice no matter how much I wanted to have sex. Maybe I should have taken the lead but I was never one of those guys who would shag anything that moved. There was more to sex than getting my rocks off.
I was 28 when I got married. My future wife moved in about a year before we married and I had access to a whole new wardrobe. I did, on a few occasions borrow her stuff but it was not regular and only ever a quick session. Mainly just lingerie. I didn't dress to the extent I had when I was younger and it was just an aid to masturbation so didn't really register. It was maybe a handful of times in 7 or 8 year.
But then it returned with a vengeance in my late 30s. I'll cover this in part 3.
Katie x
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You can see where you're similar you two but also differ slightly
Looking forward to part 3