My advice... well, the first bit is don't 'tell' anyone...just do it. The second bit is, do it when its fun for the other person. Pick a party or fun event where costumes are required and just show your image. Later, if you want to explain anything, at least they have seen you.... so the shock factor is gone. As for transitioning...no idea, I just like to CD sometimes, but I can tell you it took many years to decide I'm happy where I am. I can say by trying it, you learn what to do and I can tell you, your mind can sway pretty far each way when your experience is limited.