Like most of the sissies on here, I grew up playing in my sister's things when I was young, which probably led to my naughty fetish of raiding closets for things to play in, especially as a smaller, fit guy. When I was in college, I started wanting to experiment more, and posted my first ad on Craigslist, looking for an attached man who's wife or gf's things I could play in. It didn't take long before a man in his early 40s contacted me; he presented the perfect scenario. His wife traveled often for work, and he wanted me to come over and play dress up for him! After a while of talking, I finally gathered the courage to visit. He had his wifes little thong and bra waiting for me when I got there, which I slipped on nervously. He had me get on my knees and service him, which made my sissy clitty oh so wet in her things. I couldn't stop playing with myself as he pumped his hard 8" cock in my sissy mouth, while I was on my knees in his wife's things. He ended up cumming all over my face, at which point, I came all over the floor. I never got to play with him again, but needless to say, this has been my favorite sorts of scenarios to play out ever since, and I even kept some pictures in her bra and panties for my personal pleasure ;).