The Chevalier d’Eon (1728-1810) lived the first half of his life as a man and the second as a woman. Until age 49 d’Eon served as a diplomat and soldier in Louis XV’s France, fighting in the Seven Years’ War and spying in London for the king.
But in 1771 he claimed he was physically a woman and asked to be recognized as such. The government agreed, even financing a new wardrobe, and the chevalier spent his remaining 33 years as a woman, participating in fencing tournaments and even offering to lead a division of women soldiers against the Habsburgs.
Doctors who examined him after death discovered that his body was anatomically male.