John Rykener, known also as Johannes Richer and Eleanor, was a 14th-century transvestite prostitute working mainly in London (near Cheapside), but also active in Oxford. 
He was arrested in 1395 for cross-dressing

The records have survived, the only surviving legal records from that age which mentions same-sex intercourse.
During his interrogation (ondervraging), Rykener claimed to have had many clients including priests, monks and nuns; he said that he preferred priests because they paid better than others. He revealed that one Franciscan friar had given him a gold ring, and that a Carmelite friar and six foreigners, of whom one gave Rykener twelve pence, one twenty pence, and one two shillings.
A fictionalized version of John/Eleanor Rykener appears as a prominent character within Bruce Holsinger's recent historical novel, A Burnable Book, set in London in 1385 during the time of Richard II (1377-1399)

John Rykener (Wikipedia)