This is one of the oldest surviving recordings of a trans person.
Masoud El Amaratly (1897-1944) was an Iraqi trans singer who became famous in 1920s Baghdad for his folk music. He worked as a farmer before transitioning in his teens. The mustarjil, a term similar to trans man, then moved to the city and sang in cafΓ©s. A music agent discovered him there and his fame spread across West Asia.
Enjoy this 1925 recording of him singing the traditional Iraqi song, "Khadri al Chai" ("Please Make Tea"). Check out Ajam's website for more.