Although it has been many years, I can recall in the Cub Scouts, a significant number of boys who took great pleasure, self included, in playing the female parts in various skits and plays. It was always the same group of boys who would volunteer to play the female parts, and would readily volunteer to dress up for any event, just for another chance to wear female clothing.
Fortunately, in my case, I did not have to depend only on the Cub Scouts for a chance to cross dress.
My point? I think many, if not all, of these boys were already dedicated cross dressers, for life.