There are some interesting historical instances of 'trans' people or artistic themes through history. With men dressing as women, its usually presented as a kink for gay men, or used for laughs. Aristophanes wrote an ancient Greek comedy Thesmophoriausae which makes fun of an actual male crossdresser and playwright Agathon. Or you have Hijiras in India or Bacha Bazi.
In historical cases of woman acting as men, it was a woman either disguising herself as a male to trick people into giving her male status or an actual cultural tradition of giving a woman some male status. Albanian sworn virgins or bacha posh in Afghanistan or African tribes like the Nuer who pick daughters to act as 'sons' when there aren't any sons available. So it isn't a sexual kink, but instead a way for a woman to get power or a family to gain an extra 'son'
There is an interesting myth recorded in Ovid's Metamorphoses about a girl who was raised as a boy since birth with only her mom knowing the truth. When she falls in love with her arranged bride she prays to Venus the penis fairy and gets magically made into a boy just in time for the wedding.
All of these are very interesting to study. Humans are, and will always be, fascinated by genders and gender roles. And that is the most dangerous thing about it. Breaking 'gender norms' is a quick and easy way to become special. And in OUR culture, the special kid is always the winner.
So now we're passing out titty skittles to all the little kids who want to feel like special winners.