Kit, speaking from someone that is very hard to get to know sometimes, it's a HUGE relief when someone just comes out and says something. That could just be my personality... that I'd rather people not "dance around the bush" so to speak. Talking with my parents is hard sometimes too. Especially if it's something that I consider very personal.
All I'm saying is that I am pretty sure that he'll be supportive. Even if it takes a while for him to get used to the idea. So don't be scared.
What I'm curious about is have you talked with a counselor about this? I'm not saying that I don't support your decision... just that such a huge change in your physical appearance is not something to be taken lightly. And I have heard of people that went ahead and did it, only to regret it afterwards. (I met a girl that used to be a guy once... He regretted not thinking things through a bit. But she wasn't going back.) I have also heard that there are almost always some issues that need to be resolved before the person goes through with it.
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