Weird History
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The Cross-Dressing Prostitute Who Got Caught Secretly Having Sex With Dozens Of Nuns - And Priests

Updated June 14, 2019 33.3k views11 items

Meet John Rykener, a medieval streetwalker who dressed as a woman and slept with nuns and priests. In a 14th-century document that was only discovered in 1995, Rykener admits to being with dozens of women and men — and he sometimes dressed as “Eleanor."

Cross-dressing harlot John Rykener was caught in a stall on Soper's Lane with a man named John in the middle of a “detestable unmentionable and ignominious vice.” He also robbed the clergyman of some of his gowns, did it with a monk for a gold ring, and "serviced" three chaplains behind a church.

Rykener’s case is a peek into this industry in the 14th century, revealing how “history’s oldest profession” was practiced in medieval England. 

  • Streetwalkers Were Everywhere In Medieval London, And A Working Gal Named Eleanor Was Just Trying To Make Her Way

    In the 14th century, "working girls" roamed the city of London. Officially, the red light districts had been closed in 1310 by King Edward II, but unofficially, the profession was big business in England’s largest city. The workers were supposed to stay on one street — Cock’s Lane — but in reality, nearly every tavern or street corner might be home to “fallen women.”

    And sometimes, fallen men. 

    In December of 1395, John Britby was walking along the high road of Cheap when he spotted a "lady of the evening" named Eleanor. He asked “if he could commit a libidinous act with her.” When she agreed, the pair hid away in a stall “to complete the act.” And then they were arrested.

  • Eleanor Was Actually John Rykener, A Cross-Dresser

    Photo: Unknown / Wikimedia Commons / Public Domain

    By then, Britby had realized that Eleanor was not a cis woman. The "lady of the evening" was actually John Rykener, a cross-dresser who had a long list of clients in England’s capital. Rykener’s life is a tantalizing glimpse into a hidden side of medieval Europe. 

    Rykener was trained by a woman named Anna, described as the harlot "of a former servant of Sir Thomas Blount.” She taught him “to practice this detestable vice in the manner of a woman.” Another woman, named Elizabeth, had dressed John in women’s clothing. And as Eleanor, Rykener had relations with a long roster of women and men, including nuns and priests.

  • Eleanor Would Be Used As A Bait And Switch On The Johns To Extort Them For Money

    Elizabeth, who taught Rykener to dress as a woman, also taught her daughter Alice. Elizabeth ran an elaborate con on the Johns, sending them to bed with Alice at night, but “making her leave early in the morning and showing them the said John Rykener dressed up in woman’s clothing.” 

    The plot was likely used to extort money. When Rykener appeared as Eleanor, Elizabeth would tell the conned men that “they had misbehaved with her.”

    It was not uncommon for mothers to initiate their daughters into the profession, playing the role of evil older woman preying on an innocent youth. Elizabeth seems to fit this pattern, based on Rykener’s testimony.

  • Rykener Did It With A Clergyman And Then Took His Gowns

    A clergyman named Phillip visited Rykener at Elizabeth’s house. Phillip was the rector of Theydon Garnon, a village in Essex. After Rykener “had [relations] with him as a woman,” he “took away two gowns of Phillip’s.” When Phillip demanded the gowns back, Rykener threatened to sue him.