Gender, Sexuality and Its Expression
It is likely that there have always been gender dysphoric people but that it was only with medical advances that the approach changed. Because people could not have the physical transition it is hard to know to what extent they were. I know that different people have viewed Joan of Arc in various ways. The one writer who definitely wrote from a gender dysphoric, female to male point of view was Radcyffe Hall, in, 'The Well of Loneliness'. Virginia Wolf's 'Orlando' is also an interesting critique on gender. Some science fiction writers, like Ursula Le Gunn and Marion Zimmer Bradley also explore androgyny.
The arts have always been an area for the exploration of gender ambiguity. Recently, I saw some documentaries of 70s and 80s music and couldn't believe how feminine some of the men looked in bands like Sweet and Japan. And, of course there is Sam Smith, who couldn't be given a Brit award because they couldn't be fitted into the male or female vocalist categories.
In some societies there are alternative gender categories, like the Hijra in India and the berdache of North America. These groups incorporated those who had various physical intersex conditions and psychological ones, and the North Americans also spoke of some as being 'two spirit' people. It is possible to also see eunuchs as an alternative gender category. Their removal of the testicles was to enable singing not to change with the voice breaking, but it may also have been partly about androgyny.
The idea of androgyny may be the archetypal or mythical aspect of transgender. One Jungian writer, June Singer wrote a book on androgyny. However, she was not writing about transgender but mainly psychological androgyny. However, the transgender journey may be seen as connected to androgyny even though the person is wishing to change to resemble the opposite gender as far as possible. Cross dressers and non-binary may be seen clearly in relation to the idea of androgyny and the archetypal hermaphrodite.