His first cross-dressing experience...
After his first cross-dressing experience, a typical cross-dresser will more often than not, progress into one of three will known and well studied groups.
He will simply continue to experiment with women's clothes and makeup and crossdressing will never become anything more than a fetishism.
The second route would be spending extended periods of time dressed as a woman without wanting to be one, and it would never go beyond being a sort of mind game, and he wouldn't ever dream of surrendering his male persona.
The third route will lead him to the edge of trans-sexuality, in that he's want to live and to pass himself of as a woman for long periods of time, and the only real difference between these so-called "secondary" transsexuals, and the full blown kind is that the "secondary" kind have no strong desire to actually become a woman, and certainly wouldn't have their penises removed.