John Rykener’s Confession
Many conservative Catholic pundits–and our former pope, Benedict XVI–are quick to blame Vatican II and secular society for loosened sexual morals, and fluid notions of gender and gender roles. Influenced by this permissive culture, they argue, clergy and religious began to relax their own attitudes on sex and homosexuality. But is this situation as “new” as the pundits and pope suggest?
In London in December 1394, John Rykener was arrested for having sex with another man. He was dressed like a woman when he was caught in the act of “committing that detestable unmentionable and ignominious vice.” In his confession, he said that he had been cross-dressing for months, and worked as a prostitute, servicing both men and women. He called himself “Eleanor.” In addition to prostitution, he supported himself by working as an embroideress. The woman who taught him to embroider also introduced him to prostitution. 
John Rykener worked as a prostitute in London, Oxford and Burford. He confessed to having sex with many people, including nuns and married and unmarried women. He said that he did not charge women for sex. He also had sex with lots of men: students, married men, clerical officials, priests, Franciscans and Carmelites. Rykener “accommodated priests more readily than other people because they wished to give him more.” In addition to money, one Franciscan brother gave Rykener a gold ring. He “also confessed that after (his) last return to London a certain Sir John, once chaplain at the Church of St. Margaret Patterns, and two other chaplains committed with him the aforementioned vice in the lanes behind St. Katherine’s Church by the Tower of London.”
Sound familiar?
There is no record of what became of John Rykener, or if he was prosecuted for sodomy in Church courts.
The the entire confession here.
John Rykener appears in Bruce Holsinger’s 2014 novel, A Burnable Book.
John/Eleanor Rykener’s confession was listed in the Plea and Memoranda Roll for the Corporation of London in 1395. The document was unearthed by Sheila Lindenbaum and edited by David Lorenzo Boyd and Ruth Mazo Karrar in 1995. It was published in A Journal of Gay and Lesbian Studies, Vol. 1, pp. 459-465.