Hi! I'm a 59-year-old male cross-dresser. Am I also transgendered? Damned if I know. One of the reasons I'm here is to find out.
For as long as I can remember, I've wanted to dress like a girl, play with the girls, and generally be "one of the girls." Since I was 9 or 10, at least, and maybe earlier. In any case, it was way before puberty or any interest in sex. I suspect a lot of you are nodding your heads right now.

Once I hit 13 or so -- old enough that my parents would leave me alone in the house for an hour -- I tried on my mom's lingerie & dresses. Also typical, I suspect. I was careful, and/or lucky, and they never caught me at it. Also, I knew from the beginning that my girly desires were wrong, sick, evil, yadda, yadda, so I didn't tell
anyone about them.
Back in the 50's & early 60's, cross-dressing, sex-changes, homosexuality, etc, were taboo subjects. TV shows didn't use those themes, newspapers didn't mention them, high schools didn't have LGBT clubs, etc. As a result, although I grew up in a moderately liberal household in the suburbs of a major metropolitan area, until I was 16, I thought I was the only guy in the world who wanted to dress like a girl.
It was quite a shock to discover that I wasn't unique.
In high school, I wasn't obviously effeminate, so I didn't get teased about being "a fairy." Actually, I was an overweight, totally unathletic nerd, so my "friends" teased me about that instead.
Once I got to college, I hit the library for everything I could find about cross-dressing and sex changes (no internet in those days, kids!). I didn't talk to a counselor. Back then, colleges didn't encourage that sort of "counseling." And even if they had, I think they would have fed whatever I told them right back to my parents (no medical privacy laws).
Ultimately, I decided not to go for SRS, for a bunch of reasons. One was I didn't hate my body. While I didn't exactly think of myself as a guy, and I certainly would have preferred to have been born a girl, I didn't feel like a woman trapped in a man's body. I wasn't going to kill myself, or try DIY surgery, if I didn't get "the operation." Another was the difficulty, the expense, the grief it would put my parents through, yadda, yadda. A third was that I wasn't interested in guys. SRS clinics of the day only wanted to create "normal" women (back then, the DSM still defined homosexuality a mental disorder). A fourth was that, although that was the start of the feminist movement, men still had an easier time in my field (engineering). And a fifth was that I was afraid I'd be an ugly freak.
So I decided to live with my male identity, and I just fantasied about being a girl. Once I started living alone, I cross-dressed in private, a pattern I continue to this day. I don't go out in public, and my only contact with the CD/TG world is through anonymous forums like this. BTW, I'm sort-of passable. My body shape is okay (for a woman, I'm medium to large, but not plus sized, and I have a defined waist). But I have a lot of body hair (start with Steve Carell in the 40 Year Old Virgin, and double it), five o'clock shadow to rival Homer Simpson, thinning scalp hair, and a face that's politely described as "craggy." Yes, I could overcome those, but it would take a lot of work, and it hasn't seemed worth the effort. Or the pain.
(A full body waxing? Oh My God!)In some ways, I've been quite successful in my male identity. I've had steady jobs, colleagues respect my work, I don't abuse any substances, I don't engage in unsafe sexual practices, and I don't rack up big debts (although it helps that my tastes run to Payless, not Prada!).
But in other ways, I've been a total failure. While I have a lot of acquaintances, I have few (if any) friends. I didn't start dating until I was 24, and I've only dated sporadically since then. I've only had one or two
relationships. I've never married, obviously, and it's been a decade or more since I've dated (let alone been involved with) anyone. If I dropped dead at home, it could easily be weeks before anyone found my body.
I suspect a lot of that isolation is because I learned early on that I couldn't tell anyone about my deep, dark, evil secret.
One reason I'm here is that I'm approaching another cross-roads in my life: the R-word (*gasp!*). If I wanted to, this would be a perfect time for me to "come out of the closet" and stop living a lie. That is, transition. One of the things that attracts me to this site is there are a lot of older gals here, and I was hoping to learn from their experiences.