I don't plan to come out to a lot of people - four tops and I'm halfway there.
The first person I told was my long time friend James, a f2m transgendered person who has recently (within the past 18 months) come out himself. I don't know if it was his courage that inspired me to come out myself, but he definitely has led the way. Without him and his support I may still be in the closet with everything.
The second person I told was my most recent ex-wife. We have no children together, but it was still risky as she has contact with some of my family and we are both involved in a civic organization with which my outing could cause problems. While she was a bit taken back, she seems to be comfortable with the revelation. I did lay the groundwork for it, though, with many different sexual interests I've divulged to her over the years. This was the revelation that tied everything together.
The remaining two are a woman I know through James and another crossdresser I know at work. The latter I met in an on-line chat room. We hung out for a while, nothing sexual, but then when I got married again five years ago we lost touch. I sent him an email but haven't heard back from him. I'm not worried about that since he could be on vacation or not checking his email. It would be very discouraging if he has lost interest in cross-dressing. I would wonder if I would lose interests myself and with all the money I'll be spending to shape my body and then clothe it, I would be really upset.