Chevalier D'Eon

Here's an entertaining passage from J. S. Goldstein's War and Gender: How Gender Shapes the War System and Vice Versa;

Commonalities across cultures do not prevent individuals from breaking the mold, either. For example, the fluidity of male gender roles around war is illustrated by Chevalier D'Eon in the eighteenth century. He had a successful military and diplomatic career, and then - as a public personality, prominent in the press - hinted and finally confessed that he was a woman in male disguise. She then lived her last three decades in women's clothing - forbidden to cross-dress as a man, by order of the French king. Nonetheless, D'Eon's autopsy found "unquestionably male" genitalia. His decision... "[made] because he deeply admired the moral character of women and wanted to live as one of them"