Before my husband and I started dating back in high school, I knew he wore girl's jean which was pretty common among the "skater" kids. Most of them wore very unisex looking skinny jeans, but his always looked a little more fem, some didn't have back pockets or had a little design on them or whatever. But just the way they looked on him was different from all the other guys. Then one day I noticed he had panty lines. This was back when he was just a guy I had a crush on,
Anyway to speed this up a bit I got the nerve to talk to him after school one day, after some awkward small talk I just blurted out "You wear panties don't you?" I'm pretty sure I was more embarrassed then he was, but I could tell he was taken by surprised for a minute but he recovered and said " Umm yeah don't you?" then he smiled and I laughed, and watched him ride away on his skate board.
Well after a while we started dating and he told me he just wore the jeans and panties and aside from dressing as a girl for halloween once he never really thought about crossdressinng, and one night just for fun he put on one of my skirts and I did his make up, and it just kind of grew from that point.
Ok after all that the point of this thread before I rambled on so much is do you think he would have gone past jeans and panties if I never asked himi about it or if I wasn't with him holding his hand? Just something that I think about every once in a while, and would like to see what everyone thinks.