Wikipedia says the practice of 'cross-dressing' is centuries old, but that the term itself is as recent as 1967 and came about as a protest against an older term, 'transvestitism', which I'm finding better describes me. I don't cross-dress because I'm role-playing, or gender-confused/gender-misassigned, or iconoclastic. I do it because it's sexually exciting.
By age 10 I knew --better, 'thought I knew'-- I was gay. By my mid-40's, married and with kids, I would have said 'bi' was a better description. Today, decades later, I don't much care what you call me. ("Just don't call me late for dinner.") To whom I could respond to sexually is no one's business but my own, and --when asked-- I'll checkmark whatever box seems appropriate at the time. But my sexual ambiguity means I can't truly "pass" if I find myself in either camp, because I don't share enough of their politics and proclivities. (And I really do think 'sexual orientation' --in the sense of 'lifestyle'-- is more political than hormonal.) As for trying to present as woman, that'd take more effort and expense than I'm willing to incur for the sake of an experiment, especially since it took me years to learn how to present as a working-class hard hat, and I never did truly succeed.
When I first got into working in the trades as a marine machinist --aka, ship's equipment mechanic-- I didn't even know enough about overhauling machinery to be able to change the oil in my car. But the one thing a good liberal arts education does teach --at least in the old days before colleges/universities became mostly just Marxist madrassas-- is how to learn, and job by job, skill by skill, I learned my craft and became one of the best marine mechanics on the west coast, with a sterling rep with the naval ship sups. But here's the real irony. Though my co-workers clearly respected my skills and work ethic and I could both walk the walk and talk the talk --literally-- they knew I wasn't really one of them, that I was "slumming" as my Mom would say, and that I didn't really share the whole of their reality.
Same-same was true the couple of years I taught the lower-division rhetoric series at a couple of 4-year colleges. Yeah, I could "pass" as an instructor, because I was drawing a paycheck as one and my students were out-performing those of my supposed colleagues when all students when tested at the quarter's end in common exams. But those instructors/professors "knew" I was just a blue-collar kid with a degree from a better university than they got admitted to, but who wasn't --and didn't wanted to be-- part of their club and social class.
I think the same is true --for me-- about this cross-dressing stuff. It's not an "essential" part of whomever I might be. It's just a bit of most harmless fun while I wait for water temps to warm up and for fishing season to begin again. About that, I'm serious, and about boat-building.
Arindam