Rolandino Roncaglia: After his wife died of the plague in 1347, started wearing female dresses and prostituting himself. Rolandino had a female look, voice and mannerisms, though he was biologically a man. Because of his appearance, many people considered Rolandino to be a woman.
Rolandino Ronchaia, arrested in 1354 in Venice, was possibly intersexed, or at least quite feminine in appearance. Although he was married to a woman, he claimed that he “never knew her or any other woman carnally, because he never had any carnal appetite, and his virile member could never become erect…and since he was feminine in face, voice, and behavior, even though he did not have a female orifice and had the member and testicles of a man, many people thought him to be a woman because of his external features.” He also had “breasts like a woman.” He therefore dressed as a woman and became a prostitute. When he had sex with men he “hid his member, which never became erect. In modern terms Rolandino might be considered intersexed or transgendered rather than homosexual. He saw himself more as playing a woman’s role than as being attracted sexually to men. 
Kicked Out of Heaven Vol. I
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The Untold History of The White Races cir. 700 – 1700 a.d.
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NPR: 2 Women Charged With Sexual Battery Of Trans Woman In North Carolina Bar.