Mar 10, 2009

X-Dressing History

I've done a pretty good job of blocking out a lot of my cross-dressing history.

Like many things in my life, I tend to only remember the most embarassing or awkward moments...

I was 18 and having a graduation party. One of the guests left her bathing suit in the downstairs bathroom. (Just because it's so improbable, I'll announce that her name was Candi. No, I kid you not. Remarkably, she didn't become a stripper, though she had the body for it.) I don't know what possessed me but I put on the still-damp suit, squeezing myself into it. Seeing myself in her garment really turned me on, especially the way it conformed to my crotch and emphasized my now-hard cock. So, yes, I masturbated; rubbing myself through the stretchy bathing suit material. Afterwards, I washed and dried her suit for her and gave it back the next time I saw her. I don't know why but I always liked knowing that she wasn't aware of what I did in her clothes...

While visiting a friend in West Virgina, I spotted her panties in the bathroom and stole them. I'd heard that female genitals have a nice scent and had never smelled it before (I was 19). I stuffed them in my pocket, transferred them to my bag, and waited until I got home to partake in her odor. It was strong but, damn, it was nice. Later I'd find myself wrapping those panties around my penis as I'd masturbate and, eventually, I put them on to see what they felt like. These weren't any kind of "sexy, dainty" underthings. They were the white cotton variety that Elvis liked.

Somehow I came into possession of one of my co-worker's brassieres. I think it was during a party in which there was a lot of drinking. Again, this was around the time I was 19. The bra didn't do much for me, sexually, though I did try it on once and masturbate while it was draped across my chest (she was far smaller than me and I couldn't have put it on if I tried). I seem to remember falling asleep while this was on and my step-father waking me up the next morning. Pretty darn sure he saw me with it on but he never said anything. The man barely talked to me, ever. I'm sure this was just one more black mark against me.

Otherwise, I stayed fairly clear of cross-dressing for many years. I always enjoyed the transformation stories I read in different dirty magazines but it would be years before I'd be dolled up. I'm still interested in feminization but it just doesn't happen as often as I'd like.

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