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Transvestite - I'm the Real Bad Guy of the Series, John Ronald Brown
The first person to transition medically was probably Lily Elbe who did so in 1930 with the help of pioneering sexologist Magnus Hirschfeld. In addition to having an incredible name, Magnus was a homosexual himself and he had to hide being gay in order to practice medicine at the highest levels of German society. He established a career as a tireless advocate for LGB and particularly T individuals in Berlin.