I secretly wore panties and lingerie when I was a teenager, but became more open about crossdressing in college.  And it was sometime after college that I first had sex with a man; however, I was not in women’s clothes for my first encounter.  After that I decided that that I really wanted to be a Sissy, and have a man make me his woman, and smear my lipstick with his cock then slide my panties off to fuck my sissy pussy!