I’ve published a short historical look at transgender or crossdresser Mary Jones, who was worked as a prostitute and was discovered in 1836 when she was put on trial for pick-pocketing her male clients. Called “the Man Monster” at the time, she received a relatively light amount of treatment given the time and the moral panic of the anti-abolitionist riots passing through New York City at the time. You may read more at the link above.