Thanks to the good Jesuits of Fordham University, we know about this very busy cross-dressing male prostitute back in 1395:

On the 11th of December in the 18th year of the reign of Richard II, there were brought into the presence of John Fressh, Mayor, and the Aldermen of the City of London John Britby of the county of York and John Rykener, calling himself Eleanor, having been detected in women’s clothing, who were found last Sunday night between the hours of 8 and 9 by certain officials of the city lying by a certain stall in Soper’s Lane committing that detestable unmentionable and ignominious vice.

In a separate examination held before the Mayor and Aldermen about the occurrence, John Britby confessed that he was passing through the high road of Cheap on Sunday between the abovementioned hours and accosted John Rykener, dressed up as a woman, thinking he was a woman, asking him as he would a woman if he could commit a libidinous act with her. Requesting money for his labor, Rykener consented, and they went together to the aforesaid stall to complete the act, and were captured there during these detestable wrongdoings by the officials and taken to prison. And John Rykener, brought here in woman’s clothing and questioned about this matter, acknowledged himself to have done everything just as John Britby had confessed.

Rykener was also asked who had taught him to exercise this vice, and for how long and in what places and with what persons, masculine or feminine, he had committed that libidinous and unspeakable act. He swore willingly on his soul that a certain Anna, the whore of a former servant of Sir Thomas Blount, first taught him to practice this detestable vice in the manner of a woman. He further said that a certain Elizabeth Bronderer first dressed him in women’s clothing; she also brought her daughter Alice to diverse men for the sake of lust, placing her with those men in their beds at night without light, making her leave early in the morning and showing them the said John Rykener dressed up in women’s clothing, calling him Eleanor and saying that they had misbehaved with her.

He further said that certain Phillip, rector of Theydon Garnon, had sex with him as with a woman in Elizabeth Bronderer’s honse outside Bishopsgate, at which time Rykener took away two gowns of Phillip’s, and when Phillip requested them from Rykener he said that he was the wife of a certain man and that if Phillip wished to ask for them back he would make his husband bring suit against him.

Rykener further confessed that for five weeks before the feast of St. Michael’s last he was staying at Oxford, and there, in women’s clothing and calling himself Eleanor, worked as an embroideress; and there in the marsh three unsuspecting scholars — of whom one was named Sir William Foxlee, another Sir John, and the third Sir Walter — practiced the abominable vice with him often. John Rykener further confessed that on Friday before the feast of St. Michael he came to Burford in Oxfordshire and there dwelt with a certain John Clerk at the Swan in the capacity of tapster for the next six weeks, during which time two Franciscans, one named Brother Michael and the other Brother John, who gave him a gold ring, and one Carmelite friar and six foreign men committed the above-said vice with him, of whom one gave Rykener twelve pence, one twenty pence, and one two shillings.

Rykener further confessed that he went to Beaconsfield and there, as a man, had sex with a certain Joan, daughter of John Matthew, and also there two foreign Franciscans had sex with him as a woman. John Rykener also confessed that after his last return to London a certain Sir John, once chaplain at the Church of St. Margaret Pattens, and two other chaplains committed with him the aforementioned vice in the lanes behind St. Katherine’s Church by the Tower of London. Rykener further said that he often had sex as a man with many nuns and also had sex as a man with many women both married and otherwise, how many he did not know. Rykener further confessed that many priests had committed that vice with him as a woman, how many he did not know, and said that he accommodated priests more readily than other people because they wished to give him more than others.

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