The problem is, the subject had been taboo for a long time, and rarely did people write down their thoughts or address the issue in the past. I'm sure there were people who suffered from Gender Disphoria in centuries past, but they weren't really sure what it was, and couldn't talk about it publicly, since it was a subject that disturbed a lot of people in the old days, particularly in Western culture.
The movie "The Danish Girl" touches on this a bit in the Edwardian Era/Jazz Age, where they talk about a real-life man who wished to change his sex. From what little we have to go on, often they would deliberately live in small neighborhoods or enclaves (usually areas where other closeted LGBT members hung out) where they might find more acceptance. Some would live a double life, pretending to be normal part of the time, and living as the gender they wanted in secret over in these enclaves.
An example of these unique neighborhoods would be Greenwich Village in New York City; another would be Castro Street in San Francisco, a third would be West Hollywood in Los Angeles. Other cities around the world had them too, which is one reason you find more LGBT people in cities to this day; because it's easier for them to find more people like them in cities, as opposed to suburbs and rural areas. There are a few who got favor in royal courts in times past and would be allowed to cross-dress because it was seen as entertaining or a novelty to the courtiers, despite many courtiers or visitors finding it strange.
There might be more historical information, but I didn't bother to look.
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