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As far back as the Middle Ages, in Europe, sexworkers were represented as demons and monsters: female prostitutes were often considered succubi or vampires. In the 14th century, “demon streetwalkers were said to have been everywhere, painted, jeweled, seductively attired, and doing a thriving business among the clergy,” wrote Harry Benjamin, a modern historian and endocrinologist1. In America, the way sexworkers have been written about has been equally medieval. The very first American expose I’ve been able to find comes from 1836, when African-American, transgender prostitute Mary Jones (boy name: Peter Sewally) was arrested in full drag in connection with grand larceny. This charge stemmed from an incident on June 14th of that year, when Jones had sex in an alleyway with a wealthy white stranger, Robert Haslem. During their tryst, she lifted Haslem’s wallet. She hit the jackpot with that heist: Haslem claimed that his wallet had contained “ninety-nine dollars in Bank Bills” (equal to several thousand dollars of today’s currency) and “Omnibus Stage Tickets, worth about Two Dollars.”2 As a coup de grace, Mary cleverly replaced Haslem’s pocketbook with another man’s wallet.3

When Haslem discovered the theft, he notified a beat cop, constable Bowyer. Later that evening, Bowyer tracked Miss Jones down on her Bowery stroll. Acting the part of the trick, Bowyer entrapped her, pretending to go along with her suggestions. The constable followed Jones into the same alleyway near her Green Street lodgings, then arrested her. When he frisked her, he realized she was really a man. This alone, in fact, was a crime: it was illegal in most of the country to “dress to deceive,” in other words, to fake your gender. Miss Jones appeared for testimony in full drag, which had to have been ordered by a highly amused court, as masquerade laws would have prohibited such a display.4

The tabloids labeled Jones as The Man-Monster.5 She admitted to the court that she lived in a female brothel on Green Street, where she served as cook, cleaner, and hostess, among other duties. The Man-Monster sensation revealed the limits of 19th century American tolerance for male and transgender sexworkers. The public might have been tolerant of female prostitution, but certainly nothing that involved sodomy or cross-dressing. The Mary Jones case does show, however, that antebellum sexwork was very fluid. Boys, trans people, and women were often employed by the same houses and worked the same streets. Never mind that Mary had “always attended parties of the people of [her] own color dressed in this way.” This gender bending was, according to the media, monstrous.

New York tabloids reported the case to an eagerly appalled public. The Sun, claimed that:

The public’s hysterical interest over this case had more to do with the element of gender deception than prostitution. The media’s sensational coverage centered on Jones’ subversion of rigid social and economic hierarchies. Jonathon Ned Katz writes that Mary Jones was “working the race, class, sexuality, and gender systems to appropriate...a little of the wealth of white men.”7 Jones was ultimately sentenced to five years in a federal prison for stealing Haslem’s thick pocketbook. The naming and scandalizing of Mary Jones served as an early warning to sex clients to avoid the dark, magnetic, emasculating evil of sodomy.

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1. See Benjamin, Harry and R.E.L. Masters. Prostitution and Morality. The Julian Press, 1964, p. 169.

2. City and County of New York District Attorney Papers, 16 June 1836.

3. Katz, Jonathon Ned. “Coming to Terms: Conceptualizing Men’s Erotic and Affectional Relations With Men in the United States, 1820-1892.” In A Queer World (Martin Duberman, editor). New York University Press, 1997; pp. 227-8.