Goodness I’ve had the very same thoughts several times. “What if I would have……” when I was younger.
I had access and many opportunities to dress than I do now. I think I have a pretty good idea of where I would have ended up, and it’s not in the situation I am in today. I do love what we have, our family, wonderful kids. (Younger adults now), and I would not change that.
But again, at 17 or so, I had this job at an opera house, where I had access to amazing undergarments and was able to take advantage of that. I even had fantasies of getting caught (at work), as I had time to “play” as it were, when others were not around.
I would have been in a completely different world today.
As far as older crossdressers go, I find the resources for us are very limited. Most of what is out this is geared to a much younger generation. That is a good thing, but I’d like to have more.