Sweetheart, if you're transitioning, you're going to have to face the music one way or the other eventually and no time will make it easier so, when you feel confident enough in the direction that you're going in (and only when you're confident that this is for you), it's going to be time to decide whether to cut off your old life entirely or just come out to the world.
Personally, I just did it in a facebook post and let the chips fall where they decided to. I realize that, given your comments, I'm younger than you and the peer group that I have is probably more diverse/accepting than one for someone in your situation but I found a lot of support and encouragement in that regard. Sure some people disappeared but, that's going to happen one way or the other.