Sorry if this is too long, but I’ve been thinking about this one a lot lately…
One of my earliest crossdressing memories is also directly tied to one of the first and possibly most intense orgasms of my life. I’m not exactly proud of the sneaking around, but I used to slip into my sister’s bedroom when no one was home and I would try on all her bras and panties and sometimes her dresses, and I would dance around in front of the mirror admiring how sexy I felt in all these forbidden things. It wasn’t exactly a sexual thing, although I did try out poses I had seen in my stepfather’s playboy magazines, sometimes draping myself in a blanket or a towel with my legs spread in my sister’s pantyhose to seem more seductive or whatever.
I don’t know, I was young and clumsy, and one afternoon during the summer when I knew I was lucky enough to be alone for most of the day, I grabbed a towel and went into my sister’s room and grabbed her new two-piece swimsuit that I had been dying to try on. It was blue and had a little ruched back to it that made my ass look incredible, and maybe it was boredom and the summer heat or the fact that I knew no one would be home for several hours, but I just said screw it and walked out to my backyard to get a tan wearing my sister’s blue bikini.