I started out strictly as a top when I first dated ladyboys. Eventually I started to consider trying bottom but never did anything about it until one night I had too many beers and my ladyboy gf at the time was frustrated that I was having problems maintaining an erection. She rolled on top of me and forced her way inside my virgin ass. It hurt so much
and yet it was also pleasurable. I still top girls frequently, but I actually slightly prefer being bottom now.