I can remember when I was young sneaking into my mothers room and trying on her stockings. I don't know why I started doing it but I can honestly say that I have a fetish for women in lingerie, especially stockings. Sometimes I would get dressed up with the works: heels, skirt, bra, stockings and whatever I could find. Then I would put on some make up. I liked to look in the mirror and pretend I was a chick, while posing and playing with my cock. As I got older I stopped playing with my mothers clothes, and once at a family party I found myself sneaking into my aunts bedroom, she is very attractive and had some sexy clothes. I rooted through the drawers and selected some stockings a bra and other things went into the bathroom stripped down and put on her clothes. I pulled out my cock through the side of the sexy thong and started playing with it. I fantasized in my head while playing with myself that I was fucking my aunt and reached down feeling the soft silky nylon of the stockings. My cock got even harder as I felt the stockings between my hand and my legs. Thinking of my aunt wearing the slutty things I had on I slid my finger into my ass which led me to a great cum, blasting it in the panties I had stolen.
On various other occasions I would steal clothes from some of my girl friends or the chicks I hung out with and use them to jerk off while thinking of that girl. Recently I was studying for an exam in a girls room and she said she wanted to take a shower so she left the room and with her room-mate gone I had freedom to look through her clothes. I found a pair of sexy panties and stripped down and put them on, got dressed and waited for her to come back. The thought of having her thong on while she was there turned me on and I had to hide my erection from her the whole time. When we were done studying I went back to my room and began jerking off to the thought of her. I took off the thong and sniffed the spot where her pussy would have been and it smelled great. I had a great orgasm and shot it all over my chest.
So as you can see my fascination with lingerie has led me to do some rather awkward things but when I do get the chance to jerk it with women's clothing I have intense orgasms.