I think I've always known. I've always felt out of place and masculine. I never had a name for it.
Growing up, I always identified with male characters in stories, and I had no idea why it felt so right, when trying to identify with the chicks always felt so wrong.
Around puberty I think I had the opposite reaction from a lot of guys here. I thought to myself "Thank God!" Maybe once I grow boobs I'll feel like a proper girl. Maybe once I have my period I'll feel like a proper girl. Eventually it became: Maybe when I have BIGGER boobs I'll feel like a proper girl. This spanned from age eleven until about twenty three. This constant feeling of needing to try harder and harder to feel "right."
I would see a pretty, confident girl in a dress... so I would by a dress like that. Not because I wanted to look like her, but because I wanted to feel like her. I wanted it to make sense so badly. Problem is, I would put on said dress, and feel like I was a in a disguise. I would grow my hair long, felt like I was in disguise.
When I was a teenager I got into the whole goth thing. I felt extremely at home because I could dress like a dude, and wear makeup without anyone bitching about my boy clothes. Just about the fact that they were black and "spooky" looking. Sophomore year of highschool I shaved my head. Greatest day of my life. Went to school and everyone ripped me a new one. How dare I, a girl, do such a thing.
Pfft. I still had no word for what was going on with me. I knew very little about anything trans. All I knew was the straight boys made me gag, and the gay ones wanted nothing to do with me aside from being friends. All I knew was that something was very out of place in my world, and nobody could tell me what it was. So I cut, and drank, and did any drug I could get my hands on.
I met a boy in highschool. A boy who, at the time I pegged as gay. I don't think he even knew it yet. He crushed on me day after day and practically worshiped the ground I walked on. I didn't actually date him for a few years, but he's the first non-straight guy I can remember being attracted to me. It was the biggest feeling in the world. I dated a few other guys who were teetering in closet land before him, and always dumped them because I had this weird feeling of being totally inadequate. Like I just wasn't QUITE what they wanted.
Still I had no idea what to call myself, so I just said that I was a weirdo, and left it at that.
Queue many more years of self abuse, depression, confusion, and overcompensation. I met my husband after a long string of unsuccessful relationships, each shorter than the last. The last being a guy who was twice my age who, though he fulfilled my want for a daddy type, made me feel clunky and uncomfortable.
Husband and I have had... our problems. Cheating (him, not me), drinking, drugs, uncertainty. But we've stuck together and talked things out, and all that is about six years in the past now.
Finally, THREE years ago, we were sitting in the living room watching some stupid movie with a friend of ours. We had this little notebook that the two of us were passing back and forth. Writing naughty little messages to each other and flirting like idiots. Finally I grabbed it, and proceeded to write a six page short story involving the two of us, a little consent play, and most importantly, I was a dude. The two characters in that original little story became the inspiration for a year long exploration of myself through writing. It only took a month to figure out what had been plaguing me my entire life.
The rest is messy history. Messier. Uncomfortable crap that I don't feel like going into now. I still feel like I'm drowning inside myself. I still get the odd suicidal urge, but at least I have a name for why I'm so unhappy now.
Woo.