Emperor Hadrian

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Though he is now known for the massive, eponymous wall he constructed that defined the boundaries of Roman Britain, it took more for Hadrian to earn his place as one of the Five Good Emperors of Rome. Machiavelli hypothesized that Hadrian’s adoption was the key to his benevolent dictatorship, which was marked by a patronage of the arts and a scaling back of conquered territories. His philhellenism (obsession with Greece) spawned the revival of the beard as a fashion choice, which endured among the Romans for generations after his death. This is not to suggest that his reign was without bloodshed: his occupation of Roman Judaea was especially nasty, and rife with anti-Jewish policies.

As with all figures from historical Rome who engaged in same-sex relationships, Hadrian’s sexual orientation is difficult to translate into a modern paradigm. Online sources vary on how much interest he had in women, but he is known to have had such a close bond with a male youth, Antinous, that upon the teenager’s death from drowning, Hadrian mourned by erecting a city – and a cult – in his honor. Due to the ambiguity, he is tagged ‘bisexual’, ‘gay’, and ‘pederasty’.

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Megillos

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Megillos is a fictional character created by Lucian, a second century Assyrian rhetorician, as part of his Dialogues of the Courtesans series. One sex worker tells another of a pair of clients she’d had who she assumed were both women. However, over the course of the transaction, one had removed a wig, and insisted that he was a man despite having “a body entirely like that of all women”; when the courtesan argued with him, he rebuked her, saying, “Don’t you effeminate me!” The two of them, along with the remaining woman (Demonassa, Megillos’ wife), then had sex, which the courtesan, ashamed of the encounter, refuses to speak to her colleague about in any detail.

Though commonly described as a lesbian story (including here, where the full translated text is stored), Megillos’ self-expressed identity as a man means that the story better fits a transgender mold. For a longer scholarly takedown of the linguistic evidence, see here.