The interrogation and testimony of a male transvestite prostitute is found within the 14C Plea and Memoranda Rolls of the City of London (Boyd and Karras, Reference Boyd and Karras1995), the content of which has been re-ordered for the purposes of this article.
On 11 December 1394 in the presence of the Mayor and Aldermen, John Rykener, calling himself Eleanor and dressed as a woman, admitted ‘committing that detestable, unmentionable, and ignominious vice’ in women's clothing for money the previous Sunday night between 8 and 9 with John Britby – who said he thought Rykener was a woman.
Rykener swore that Elizabeth Brouderer first dressed him in women's clothing and called him Eleanor; and, Anna, a whore, taught him to have sex like a woman. In addition: the rector of Theydon Garnon had sex with him as a woman; at Oxford, for five weeks, in women's clothing and calling himself Eleanor, he worked as an embroideress, where he often had sex with three unsuspecting scholars; in Burford, at The Swan for six weeks, he had sex with two Franciscans, a Carmelite, and six foreign men, for a gold ring, 12 pence, 20 pence, and two shillings; in Beaconsfield, as a man, he had sex with Joan Matthew, and he had sex with two foreign Franciscans as a woman; and, returned to London, he confessed to the aforementioned vice in the lanes behind the Tower with a Sir John and two other chaplains. Furthermore, he often had sex as a man with nuns and women (married and otherwise) and as a woman with priests, how many he did not know, albeit he accommodated priests more readily than others because they gave him more.
Then, sexual immorality was under ecclesiastical jurisdiction, and prostitution and procuring were dealt with by city courts. In any event, leaving aside veracity, credulity, and legal, political and religious contexts, no record has emerged of the outcome of the case.
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