With high school, things changed a little because I had a little more alone time when I was trusted to hang out at the house alone while my mother drove my little sister to after-school activities. So I tried out some of my mom's old clothes - the ones in the attic that I knew she wouldn't be wearing anytime soon, if ever. It was comforting. But at the same time, I felt that it was very wrong, and I "knew" based on my reading that it was "abnormal". In other words, an urge I should fight and not let anyone know about.
In college, I met my future and current (and hopefully always) wife. She was not from the conservative midwest like me, came from a large rather liberal metropolitan area, and she had and accepted a family member who lived an alternative sexual lifestyle. I guess I was comfortable enough with her to slowly slip my secret. She, bizarrely, loved/loves me enough to accept that about me, though we agreed that expressing my femininity was something I'd just do in private. At the time, I thought that was enough, and besides, the thought of social ostracism from anyone else finding out frightened the heck out of me. As it turned out, I didn't even do much in private since we were soon busy with both college and babies, then grad school and toddlers. Eventually though, an odd confluence of events reignited the urge to be feminine. For unknown reasons, I developed gynecomastia - enlargement of breast tissue in a male. Unfortunately it was unilateral, and even today after being on hormones, one side is a little bigger than the other. I would joke that this was God's way of pissing on me - "You don't like the way I made you? You want to be more feminine? OK, here, have a breast. No, just the one. You don't like it? F**k you! " At about this time, my kids were getting older and more independent, and I again had a little tiny bit more time, so I began to dress again, mostly just wearing feminine underwear beneath my regular clothing. I doubt it looked attractive, but it made me feel better knowing that at least in some small part, I was acknowledging my "real self".
These days, the term "transgendered" is used in place of the older terms because it encompasses greater variety. No longer do professionals in the field consider gender as a binary, but rather as a continuum. In some ways, I think this is great and I applaud the idea that people can be very feminine men, or very masculine women. I think politically, this is a harder sell to the general public than the old "woman's brain trapped in a man's body" type of sexuality, but eventually, the more inclusive idea is the ultimate goal for acceptance. That said, I don't think of myself as a man with very feminine instincts or thoughts. I think of myself as a woman who has, for the last 42 years, played the role of a man to varying degrees of success out of genetic and social necessity. If (and that's a big "if") I were to transition, I wouldn't really want to be known as transgendered or transsexual, I'd want to simply be considered a woman. I know some people would say that's turning my back on my "sisters". I don't see it that way - I still support their right to feel however they feel about their gender - I just happen to still think in the old gender binary, and I don't want to be a former male or feminine male or transgendered m2f, or what-have-you. I just want to be a woman.