Just some background, I'm 33 and entirely self supporting. I was visiting my parents over the holiday. I'm feeling my way forward with this whole thing, and I wanted to come out to them sometime soon as the secrecy was starting to get to me. Last night while we were finishing dessert after dinner I knew that it was now or never if I was going to do it this trip. So I had to will myself to do it, which made me very nervous, to the point where my mother asked if something was wrong. I sort of pushed it out, that I had wanted to be a girl since I was 10, that I had been in denial for a very long time and all of the negativity and self loathing that went along with it. They were shocked and had no idea. My father was sort of in shock about the whole thing and just kept repeating "you're a guy... you're a guy." and "there has to be something we can do so you can stay a man" My mother snapped out of it faster. I was very nervous so I don't remember exact details. They talked about how they love me and would support me in whatever I end up doing, and we hugged.
So the world didn't end, the ground didn't swallow me up, and I still have a family, so all in all it was a successful coming out. I was a little scared about my father since he took it really hard, but we talked again today and he seemed a bit better, he ended his phone call with "we love and support you."
One thing I didn't prepare for is just how weird having your parents talk to you about this is. I talked to my mother this morning and she did some googling (I knew she would) and started quoting Paul McHugh which was kind of annoying, though she seemed to be really put off by his ascerbic personality. It's just very weird that they are now a part of this.
Everyone's about to tell me how lucky I am and what great parents I have. And you're right I am and I do. That makes this hard for me, they're now going through their own version of what I went through when I had to come to grips with this, and its hard not to feel like I'm directly causing them this pain. They've been amazing to me and they don't deserve this.
One thing I did that I think helped a lot was that I never used any words that included trans. That way you don't bring up any preconceived notions, and the conversation is just about the fact that you're hurting and need their help.