'I Wish I Were a Man'

In any discussion of war recruitment posters, those produced by Howard Chandler Christy for the US Navy in World War I are among the most interesting, at turns flirty and then playing on male insecurities: "Be a Man!" His best one, from 1917, is this gender-bender:

Henry Fielding (of Tom Jones fame) anonymously published a satirical pamphlet The Female Husband in 1746. It was based on a true story about a woman, Mary Hamilton, who lived as a man and had a number of lesbian marriages. One bride eventually caught on (ya think?) and Mary was convicted of fraud, not sexual immorality, let alone bigamy. She was punished with six months in prison and a public whipping. Fielding reveled in it as a pot-boiler and later it became a salacious play - the image below is from an 1813 edition:

Up top is a painting that surprised me when I first saw it: how did Jean Delville get away with this L'Ecole de Platon? It may be titled "The School of Plato" but it looks like Jesus and the Disciples in implicitly homosexual poses.

Reversing the gender-bending, there was the French diplomat and spy, the Chevalier d'Eon (Charles de Beaumont), who lived the first half of his life as a man, and the second half as a woman (c.f. Virginia Woolf's Orlando). In 1787, he fought the equally famous French "mulatto" Chevalier de Saint-Georges in a duel in London, probably to raise money. Whether he was dressed as a woman or a man, the cartoonists had a field day with it. Apparently "she" cheated but "he" won the duel.

For more gender-benders - try Tiresias who was both genders, or these chapters Pope Joan and George Sand and "Lili" at the bottom of this page or the murderess Eugenia Falleni.

Then there are the Borghese statues of Hermaphroditus, like this one below in the Louvre, which is said to be a Roman copy from the 2nd century CE after a Hellenistic original of the 2nd century BC.

The Borghese Galleries in Rome also have a 3rd century Standing Hermaphroditus, with a full erection greeting visitors. I think this is what I saw (photos were not permitted so I forget).