After a few years in an orphanage of the Sisters of Mercy, O stole some clothes from a girl of the same size and took her certificate of domicile and ran off to Switzerland, where she found work as a nanny, and taught herself embroidery. When she was 16, a man tried to force himself on her and denounced her as a 'hermaphrodite'.
O moved to France and found work as an embroiderer. She also worked for a while as a man after a friend's boyfriend threatened to report her to the police. In 1882 O emigrated to New York, and again worked as an embroiderer. A co-worker forced himself on her, and discovering her body, used threats of calling the police to make her an involuntary sex partner. One day when he was away O dressed as a man and fled to Milwaukee and worked in a timber-yard and as a cook.
In 1885 O arrived in San Francisco, where cross-dressing had been a crime since 1863. As a man O became an itinerant bookseller, invested in property and began traveling for German newspapers. Indoors O, as a woman, helped with children, and provided accommodation for dance-hall women.
In 1905 O wrote to the new German magazine Mutterschutz (Mother Protection) enclosing an article re feminine boys and men:
"If he is raised as a girl, then he will lose all doubt and will be more stable in his girlishness, so that he will then never will ever want to become a man; if he forced to behave as a boy, then he will feel destroyed and will yearn for the time when he can make a living as maid or something like that".Despite that Mutterschutz advocated the equality of illegitimate children, legalization of abortion, and sexual education, it was not ready for this, and did not reply. O then wrote to Magnus Hirschfeld enclosing the rejected article. They corresponded and Jenny provided photographs for the 1912 supplement to Die Transvestiten.
- Magnus Hirschfeld. Die Transvestiten; ein Untersuchung uber den erotischen Verkleidungstrieb: mit umfangreichem casuistischen und historischen Material. Berlin: Pulvermacher, 1910. English translation by Michael A Lombardi-Nash. Tranvestites: The Erotic urge to Crossdress. Buffalo: Prometheus Books. 1991: s. 1991: Case 13: 83-93.
- Magnus Hirschfeld & Max Tilke. Der erotische Verkleidungstrieb (Die Transvestiten). Illustrierter Teil. A. Pulvermacher, 1912: plate XXII.
- Clare Sears. Arresting Dress: Cross-Dressing, Law, and Fascination in Nineteenth-Century San Francisco. Duke University Press, 2014: 73, 76, 78-80.
If born a century later Jenny would, quite likely, have been an early transitioner. She did as much as she did without estrogens, and probably had no way to find out that there were cities others than San Francisco that did not have such anti-cross-dressing laws.