Some insignificant dress up play in both parenst cloths as a child, but that was just a kid being a kid
There was the opportunistic trying on of some female garment that was available and fit during my adult life. Some use of nail polish when home alone. No big deal.
There was the grab of the cross dressers hall pass in high school: doing theater. Class skits at pep rallies. This was just part of the slap stick, a parody. But, at least I got to wear a dress and try to walk in heels. But that was just the class clown twisting his ankle for the school to see.
The birth of Kelly, my femme side, happened much later. I seized the opportunity to book a day of femininity at a local make over service. The first hour I was terrified because I was still that class clown putting on girl stuff. Then one time I looked in the mirror and didn’t see the clown. I saw Kelly. The rest of the day, I had a lot of fun. At the end of the day I could truly say that for the first time all the desires I could never quite get rid of had been satisfied (at least temporarily). [The next day I plunged into a angst filled pink fog, but I want to be upbeat here and will save that for other posts].
It was magical. But really it was just the opposite of a good illusion. A stage magician makes the audience believe that he has turned something ordinary into extraordinary. What happened is that the audience (me) believed that the extraordinary (a dude in women’s trappings) was the ordinary (a woman). A not terribly attractive woman, perhaps. But we can work on that, and have fun doing it.
I learned a couple things.
First, for me it is the whole package. Underdressing or sporting some jewelry or mowing the lawn while wearing lipstick is not going to placate my needs. I got to get completely decked out.
Second, it is important for me to pass. Even if I am the only one that will see me. When I do that, then I am happy.