Love your observations and anaysis. To kick in a bit, I notice many trans people at the cutting edge of individuation today as they reject some gender stereotypes while embracing their gender. I edit dozens of stories a month by trans people and read more in the course of preparing my own stories, and I've been struck by that phenomenon, which can come at a cost to individual trans people.

Breaking gender stereotypes exists in strong tension with the need to "pass," which even if it's not a deep-seated desire can be quite important for safety reasons. I guess we mostly think of nonbinary folks as the strongest gender "rebels," but trans folks who strongly identify as one gender are often out on the frontier breaking gender rules too. (This can be controversial in some trans communities.)

Oh, and on the Roman sexual role thing, it's fascinating to me that it's come down almost intact (culturally, if not legally and religiously) in some Latin cultures. The effects are much less pronounced in the English-speaking world with our "buggery" traditions that strictly criminalized any form of male/male sex. But in societies closer in language and traditions to Rome, the distinction persisted into living memory.

It's not unusual to encounter Spanish, Portuguese, and Italian-speaking men who look with tolerance on men who penetrate other men but not on men who get penetrated. I think ideas about sexual identity are subsuming these cultural traditions, which I don't think are as strong as they used to be, but you still see them.

"He's not gay," said my Mexican buddy. "He just wanted a blow job." That's a confusing bit of cultural mingling, sexual identity colliding with much older concepts of acceptable sexual behavior.

But even in the English-speaking world, ideas about gender "betrayal" prop up homophobia. Having sex "like a woman" really is strongly stigmatized for men, even if we aren't as explicit about it as Latin-derived cultures are.