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.
I was pretty nervous about neighbors seeing, but I figured they’d have to look into the backyard to be able to notice me, so I just layed out in the back hoping the sun would burn an imprint of her swimsuit onto my body so I could enjoy the tan lines later. I had tucked myself back so I could appreciate the flat POV, and I guess I was way more into the whole thing than I realized judging my how difficult it was for me to hide my excitement and still be able to lie down comfortably on my towel. I kept tucking it back and I guess it was from the pressure of me pushing back and the excitement of actually being outside in a bikini, because for some reason I just couldn’t hold on any longer and out of nowhere I just started to cum all over myself and my sister’s new swimsuit!
Don’t get me wrong, I had made myself cum once before, but it definitely wasn’t a normal thing I had started doing yet, and I was freaking the fuck out about what I was going to do. So there I am lying on a towel in my backyard and I’ve just made a mess of myself and have no idea how I got so turned on so quickly. And I didn’t go inside, at least not right away. I don’t know why, but I just stayed there for a few minutes all out of breath running through in my head what had just happened. I didn’t even know what a hands-free orgasm or any of that was yet, but looking back on it, I had somehow managed to cum just from sunbathing.
I did finally go back inside, and I handwashed her swimsuit bottom and stuck it in the dryer before anyone got home, but wearing panties took on a whole new excitement after that and I’ll always look back to that summer as a unexpectedly defining moment!
Source: reddit.com/r/gonewildstories/comments/909u61/tm_wearing_my_sisters_bikini_and_my_first