When I first started seeing my shrink about my gender identity issues and told him I wanted to attempt transition again he suggested that I first try wearing women's knickers under my men's clothing. Y'know, "ease into it". I kind of felt that was absurd advice. He was talking to someone who had previously cross dressed on and off as part of my first attempt for close to two years. "Yeah, doc, I already know what wearing ladies undies feels like, sheesh". Also I don't think I could bring myself to wear any female clothing under my male clothing. It's probably odd, but it's just the way I felt.