I was born long ago enough that the word "transsexual" is power-packed with dark innuendo.
I grew up in a conservative home. I was the first of three children. I have no memories of any tell-tale experiences as a young child, but that may be because I have very few memories indeed from that time. My home was a very unhappy one. If I did exhibit any such tendencies, my father would have done everything he could think of to drive them away; and he would have done it with love and a heart full of sorrow. He was a very good man with definite ideas.
I don't remember this; but my mother once told me that, when I was quite young, she found me in the bathtub, a razor in my hand, blood streaming down my leg. I smiled broadly and said, "Look at me! I'm shaving!" or some such thing. After I came out to myself, it struck me that I had chosen to imitate her shaving, and not my father.
I had no clue that I was trans for a very long time. In retrospect, there were plenty of signs. My heroes in life were almost exclusively women. I adored Chris Evert. I used to think I adored her because she was so beautiful, so talented and such a lady; today, I realize I wanted to
be her. It's interesting that I couldn't admit that to myself at the time, which suggests that something, sometime had scared me away from identifying with women – even to myself.
When I was 12, something went wrong. I felt like I was losing my mind. I didn't know how else to describe it. I was terrified. My father, being a professional man, did the educated thing; he sent me to a child psychiatrist. I spent the summer seeing Dr. S, once a week, and remember virtually nothing of the experience. In later years, I thought it was curious that this had happened when it did, at the onset of puberty. I suspected something hormonal had been involved; but still, knowing nothing of the relationship between testosterone and dysphoria for us girls, the possibility of being trans never occurred to me.
Throughout my life, people have wondered if I was gay. This always amused me greatly, since I felt no attraction to men. I had the odd "homosexual fantasy" when I was 14, which most heterosexual males experience at one time or another in their lives; but I liked girls. I think the first time I was asked if I was gay was also when I was 14. Much later in life, I had a close friend who never said anything like this to me; but when he died his widow told me he had sworn, up, down and sideways, that I was gay, gay, gay. Several years after that, my wife and I were regular visitors at the home of a gay male couple in our neighborhood, and, one day, they told me, deadly serious, that I was the "gayest straight man" they had ever met, and they didn't understand it.
This "gay" connection seems to be a common experience for trans women before they come out; I've read several other accounts like mine.
I think I was in my late 30s when I saw my first lesbian film, John Sayles' "Lianna" (1982). I was spellbound. I discovered that I connected with this genre very deeply, for reasons I could not explain. As the years went by, I amassed a respectable collection of films in this genre, and branched out into what little there was in television: the 5th season of "Ellen," and "The L Word." It was "The L Word" that introduced me to the concept of the "male lesbian." Naturally, the term intrigued me, because I thought it might explain what was going on with me. I investigated and learned that "male lesbian" is a euphemism for a "love shy male." It's more complicated than that. There is a list of characteristics that are typical; if you check it out, you'll probably suspect that a "love shy male" is probably a trans woman who just hasn't come out to herself yet, at least some of the time. Most of the items on the list were true of me, including the wish I had been born female, the belief that I would have been happier and able to be more myself as a woman, wanting only female children, etc. So, I provisionally classified myself as such a person. And, since there didn't seem to be anything I could do with this knowledge, I put it on the shelf, taking it out again from time to time to re-examine it.
It was on one of these occasions, when I was about 50, that I had a watershed experience. I was taking another look at my "male lesbian" status, and it occurred to me to ask myself, "Well, if I
could be a woman, what woman would I want to be?" And I knew. I didn't even have to consider it. The answer popped immediately into my mind – and I was in orbit. I stayed there for about four days. The thought of being this woman produced what I now know was gender euphoria. I didn't know it then. All I knew was how incredibly happy I was, thinking of being this woman.
I shared some of these things with my wife, who, as it happened, was a straight ally and board member at the local LGBT center. She shared some of what I told her with someone she knew there – a trans man. He suggested that I might be transgender. She relayed his suggestion to me, and I blew it off. Silly me. I could have known
ten years sooner than I did.
I think I have written separately how I finally knew. I was investigating my "strong feminine side" that I had always known I had, with the intention of bringing it to the surface and integrating it with the rest of my conscious personality. It's pretty standard psych stuff. One thing led to another; and, about six weeks into my investigation, I knew. Three months before my 60th birthday.
Better late than never!

And, let me say, coming out to myself and transitioning have been the greatest experiences of my life. How could they not be? I'm finally myself, after a lifetime of trying to be someone else. If anyone reading this has any doubts about taking the plunge, my advice is to go forward and not look back. Nothing is worth denying who you are.