I think my parents knew something was off about me. My dad did everything he could to remind me, every day, for years, that I was a boy, and telling me how to act like a boy, look like a boy, talk like a boy, pushing me into doing boy things. If I tried to swerve into something even remotely feminine, I'd just get checked right back into line. After my parents divorced, I was in counselling for a while, and I actually said something to my counselor about feeling like a girl. She didn't really seem to think it was that big of a deal, and we never really talked about it, again.
I'd have this surface up again in 2001, but I was in such a deep self-denial about it that I'd tell people I was simply going through a goth phase. After 9/11, when people got seriously spooked over every little thing, I was basically given the big intervention by the church folk, who didn't take kindly to the all the black makeup and hair dye. No one every said anything about cross dressing. They thought I was going down this Marilyn Manson path. So I gave up. Tossed the makeup and the fishnets, removed the nail polish, bleached out my hair, and went back into full repression.
There was a few things I did sexually that felt very tied into my feminine identity with a girlfriend I had, also in 2001. It didn't go well. She kind of only did it because she thought if she did, I'd turn around and become the man she wanted in bed. All it did was hurt and make me feel even more uncomfortable and alienated. She didn't even care, she wasn't gentle or loving about it. And I still feel horribly stupid for ever trusting her with this, because she just kept using it as a weapon against me throughout our relationship.
Looking back, it all makes so much sense, now, but it was never anything I could have picked out on my own then. Maybe because I was young, but also because trans awareness was so... nonexistent. I think that if I had been born a decade later, I'd have been able to piece this together sooner, have a better chance of expressing how I really felt to that one councilor when I was 13 and was able to say, maybe for the first time to anyone, that I felt like a girl.