I was living with a girl friend who was very adventurous sexually. and we were very competetive, daring each other to do things and neither of us wanting to back down from these dares. The one night she had put on a new lingerie set and was showing herself off to me and asking how she looked. I told her she looked fantastic and said good thing no one else can she. she said that if any one else saw her they would be shocked senseless. as an idle comment I said so you would let someone else see you. this was imedialy taken up as a dare. she said so spit it out what shall I do. after a quick think I said. walk to the end of the street and back, no running jut normal pace to the end and back. she said she would do it and sure enough she did the walk. as it was very late there was little chance of anyone being in the quiet street where we lived.
on her return she gave me a dare. she said, I did it. now you do it.
no wat I was going to back down. I said no problem doing the walk in my underwear.
she said no.
do the walk in this set of underwear.
I had to think for a second but I could not back down so I stripped and put on her red panties, bra, suspender belt and stockings. her high heels were far too small for me.
she went over the rules again, walk all the way there and back no running.
I began my slow walk and was enjoying the feel of the clothes and the taboo idea of wearing them. my cock so stiff in the panties I had to touch myself a little as I walked.
almost at the end of the street I was about to turn and walk back when she let out the loudest wolf whistle.
I had to follow the rules and keep walking slow. I dont know if any of the neighbours were looking out of their windows at my but that thought turned me on even more.
when I got back inside the house I was going to take of the undies but my girl friend said keep them on.
I did keep them on all night and for some time in the morning.
she liked seeing me in them and I loved wearing them. a switch had been flipped in my head which would never reset.

When I was younger, I remember looking at the Big Sears catalog, Coming across the Stockings and Garters and foundation wear. It was a instance turn on for me. And later on , I found myself home alone . I snooped in my moms things and found a garter belt and some stockings, I could not help myself, I slipped them out and hid then under my mattress , Later that night , I put them on and my cock got hard before I got it all on and stockings hooked....

I was around 12--14 best I can remember, But I was hooked!! It was just super Hot and few days later I added one of her pointed bras I don't remember the size, But just a nice size tit she had, I seen her topless once and she had great nipples ... But now with the all white garter belt and bra , suntan stockings. I jerked my young man cock till it was nearly black and blue!! But Damn it felt wonderful and made me super crazy horny to wear it..... So I guess the Sears Robuck Catalog Compelled me to enjoy cross dressing . I'm early 60 now and it still is a huge turn on for me.....

Nothings compels me to dress, I do it whenever I want to. I like to wear black nylon stockings, panties, garter belt, bra and high heels....this gives me a hard cock which I usually jerk off