So, I'm maybe a few months from moving out and trying to make it on my own. When I first started thinking about transition, I thought I would wait until this time to start going by my chosen name and male pronouns, and stay in girl-mode around my parents until I was ready to tell them. I'm not sure I can wait anymore, though.
My parents are separated, and I live with my mom. I know she is at least aware that I've questioned my gender identity. Just a few weeks ago, we got into a conversation that went in the direction of gay marriage, and other such things. Long story short, she asked if I had any doubts about my 'sexuality' (she meant 'gender identity', but probably just doesn't know the difference) and felt like I wanted to be a boy. The question caught me off-guard, so after a bit of silence I answered "Sometimes." We haven't discussed it since.
My mom is not the most stereotypically feminine woman, and grew up in a very conservative family. She always hated having to wear dresses, act like a lady, things like that. She told me she understood my feelings, but it seems to me that she enjoys being female physically, just not having to act girly. I don't know if she knows anything about body dysphoria.
Anyway, she's in New York right now and left me to take care of the house for two weeks. I ordered a binder that should get here before she comes back. I plan on telling her when she gets home, somehow. Maybe just wearing the binder and see if she notices my tits are missing.
I'm nervous, obviously. My mom has always been tolerant and accepting of other people being different, but I've read many coming out stories where people expected to be accepting were not, and vice versa. She may be fine with someone else's kid being trans, but I don't know if she'd feel the same about me.