It started kind of strange. I am or at least was Len or Lenny – Leonard to my mother – a guy in my early 20s, kind of short and slender. I had a sister, Karen who was a few years older than me. She’d had a nasty breakup with a fiancé, and stayed with me for a while when she was trying to put her life back together.
It was a bit inconvenient, since I just had a one bedroom place, and not all that big. Being a nice little brother, I let her have the bed, while I slept on the sofa. She had a ton of clothes and more than filled my closet, leaving little room for my clothes. Beyond that, we had to share one tiny bathroom, in shifts, since there was no way we were going to be in there at the same time – too small and too weird.
Karen stayed with me for about six months before getting her own place and moving out. Her place was smaller than mine, so while she took most of her stuff, she had more clothes than she had room for in the new place. She didn’t want to donate them, so she asked if she could leave them at my place until she could afford a bigger place. Again, being a nice brother, I let her do it.
Karen left behind all manner of things, skirts, dresses, blouses, bras, panties, shoes, makeup, and all that. After I while I got fascinated with it, which I guess was my first mistake. I started by just touching some of the clothes. I was a pretty nerdy guy who could never get anywhere with women, so even touching the clothes was a turn-on.
I started by just touching her clothes while touching myself, then jerking off until I came. I progressed to smelling the clothes and draping some of them over my head while doing myself. After a time, that didn’t turn me on the way it once did, so I even began putting on some of her clothes. That seemed to be a bigger turn-on and her clothes seemed to fit, since we were almost the same size.
As time went on, I’d dress up completely in Karen’s clothes for my self-abuse sessions, and even left them on after I’d cum. I began to play with it all a little bit and even began to use some of the makeup she’d left behind. I’d pad her bras with socks or whatever, put on panties, a skirt, blouse, and shoes, then brush my hair in a more feminine style and learned how to do my makeup.
It all seemed innocent. I was in my place, by myself, using it all as part of self-stimulation. Hell, I needed to get off too, and there were no girls willing to help me. Before long, I’d come home from work, dress up all girly, and prance around my apartment before getting myself off. I’d even wear one of Karen’s old nighties to bed afterward.
I had a few friends who I’d hang out with occasionally. One of them, who I’d known since high school was Matt. He was always the popular sort, never had any problem getting girls, and often seemed to have one or more hanging off him. He’d take me along as a wingman sometimes, though I never managed to get any girls out of it.
One night he and I were drinking, and I’d had more than I should have, and we began talking. He started telling me about how he got some chick to let him finger her in public in a restaurant. He said they’d also gone to a movie theater, sat way in back, and she hiked up her skirt, sat on his lap, and fucked him in the theater during the movie.
“Hey, Lenny, what’s the kinkiest thing you’ve even done?”
“Shit, Matt, I can’t get girls to do ordinary shit with me, much less anything kinky.”
“Come on, guy, you must have done something just a little bit out there.”
As I said, I’d had too much to drink, and I confessed to dressing up in my sister’s clothes to jerk off.