In December 1394, John Britby, on a visit to London from Yorkshire, approached a woman on Cheapside. After a short negotiation, she agreed to have sex with him in exchange for money. The two removed to a side alley, where they were then arrested by the authorities for “committing that detestable unmentionable and ignominious vice” – presumably, sodomy. The problem was not that the woman was a sex worker – this was a valid way to earn a living in a medieval city for a woman. The problem was that the woman was, biologically, a man.
The story of Eleanor Rykener (born John), was only uncovered in the 1990s after a re-translation of the London Plea and Memoranda Rolls (the civic records of Medieval London). Previous translations of the folios had only summarised the contents, rather than exposing the full details.
In the account, Britby confessed to having fully believed Rykener to be a woman, hence the approach and commission for employment. Rykener then tells of their journey into dressing as a woman, and how they were trained as a sex worker. The testament continues with Rykener describing their employment in Oxford the previous summer, where they worked part-time as an embroideress, the other half of their time serving both men and women for sexual labour. Clients ranged from nobility and foreign dignitaries, to priests, monks, and nuns. Rykener even noted a preference to working with the clergy, as they paid more!
We do not have the records for the outcome of the trial, but the account is unusual in several ways itself. First, crimes of a sexual nature, especially sodomy, were usually prosecuted by the church, whereas these were civic records. This would imply that this case was larger than that of sexual deviance – perhaps as a way of uncovering church corruption itself, as Rykener lists many clergy among their clientele. We also do not have the corresponding church records for this time period, so we cannot clarify if the case was doubly prosecuted.