According to H.H.'s own account, his parents died when he was young. He left school and Germany, and worked his way to the US as a ship's boy.
In New York he became a musician, a flautist, but was unable to find a place in a men’s orchestra. However, presenting as female, H.H. was engaged by a women’s band and chorus (Damenkapelle). She travelled for several years with this band as a flute player, without being read.
Eventually, H.H. left this post, but she felt so natural in female clothes that she continued so. She worked in succession as a chambermaid, a soda-seller, a waitress, and a buffet-maid. She then joined a circus, and advanced quickly from an extra to performing as an equestrian acrobat. A fall from the horse, which stretched a tendon, put an end to this. However she then became a female musical clown in the circus, and later formed a singing group with other women, in which she sang the second voice.
In later life, back in Germany H.H. worked as a Damenimitator.
Dr W.S. commented that H.H. was "A very strong character, when dressed as a man he was almost tough. Not at all sweet or affective. Dressed as a woman, as he now preferred on the street, he was graceful, amiable, and so confident that one would hardly believe his story."
- Dr. med. W.S. "Vom Weibmann auf der Bühne". Jahrbuch für sexuelle Zwischenstufen, 3, 1901: 313-325. Online.
- Vern L. Bullough & Bonnie Bullough. Cross Dressing, Sex, and Gender. University of Philadelphia Press 1993: 223n16,
Possible she was one of the lucky few like Rachel Harlow or April Ashley who appear female even before attempting transition.
I hope that H.H. getting a job only in a female band does not imply lower standards in female orchestras. Just as likely is that as an immigrant, H.H. was not accepted by the male musician unions.
Would a cis male disguise as female in this way to get a job and keep up the disguise day and night (when travelling) for several years? While such a situation is a common trope in fiction, and also in cross-dreaming, I am not able to find a real-life example of such, However if H.H. were trans she would be delighted with the opportunity.