When did I first crossdress? Hmm good question. Maybe I'll answer like Bill Clinton - depends on what your definition of crossdressing is. Definitely in my early teen years, I developed a strong panty fetish and I borrowed my sister's and mother's nylon briefs whenever I could. I may have even put on a bra from time to time but all of these experiences were very quick with one goal in mind. I do remember though being fascinated with the small advertisements that were in the back pages of Penthouse and Hustler for a place called Michael Salem's TV boutique. So, curiosity was definitely there.
Then in college, a girlfriend left a pair of panties and pantyhose and I did not bother to return them until I had tried on both. I remember the feel of the pantyhose and it was - well, you all know - great. After that, my opportunities were few and it was not until I got out of college and I was living in an apartment on my own that I first bought my own lingerie. First just panties, then a bra and soon after, the whole range of lingerie inclusing garter belt, stockings, slips, camis, etc. I think at that point i had probably "crossed over" Even though I have purged many times since due to moves, marriage, kids, etc, I keep coming back.