By the time I told my wife's family, I'd already been on HRT for 6 months or so, my hair was getting longer, etc. So some of them pretty much guessed what I was about to say, and yet some were still surprised. But I never did the "Bill on friday, Betty on monday" sudden change thing, so I think THAT really helped ease everyone into what was happening. I just let the HRT do it's magic, and slooooowly evolved into Kate when no one was looking, lol. By the time I was fulltime, the whole issue was boring old news to everyone.
I came out by calling some people, telling some in person, and emailing others. Some people I sent a copy of "True Selves." Some I emailed a long explanation of GID I had written up. Some I showed my Carry Letter.
If I had a Do Over, I wouldn't have made such a big deal out of it. No one really cared about the details, they just wanted to know that I was happier and really wanted/needed to do this. I wouldn't explain GID, I wouldn't get into explanations of birth defects and all that justifying, apologetic stuff which just makes it sound like *I* don't believe it's OK to do. I'd just say, "I've been changing my sex for a few months now, I'm changing my name to Kate soon, and I'll be living as her for the rest of my life." If they then had reasonable questions about the process, I'd answer them. If they questioned my DOING the process, I'd politely avoid getting tangled up in that... it's not there place to question me.
Neighbors and professional contacts I didn't tell until it was pretty obvious what I was doing, so they knew already when I said, "Oh by the way, I'm Kate now." And none of them cared beyond congratulating me.
My own parents were impossible though. They hadn't seen me (still haven't), so there was no way to cushion it. After I told them, I sent them "True Selves." I don't think they read much of it. I try to discuss it, but neither of them wants to talk about it or see me. We talk on the phone, but we have to avoid The Subject.
~Kate~