Charley Wilson

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Charley Wilson (née Catherine Coombes, born 1834) lived as a man for over 40 years.

He worked at various trades, but in 1887 fell on hard times and was obliged to live as a man in a London workhouse.[1][2]

But another source claims that Wilson went to America and became an outlaw:

"Charley Wilson, better known as 'Little Britches', born in 1834 in Britain, was a cattle thief from the Indian Nation of Oklahoma. ... he lived as a man for over 40 years till he had to move into a facility for the elderly at age 63, where authorities forced him to dress as a woman. Charley is listed as 'one of the most famous female outlaws ever to strap on a six gun' despite his masculine dress and choice of male name."[3]

References

  1. Jason Cromwell, Transmen and FTMs: Identities, Bodies, Genders, and Sexualities, University of Illinois, 1999, page 78, quoting Thompson, 1974.
  2. Susan Stryker and Stephen Whittle (editors) The Transgender Studies Reader, Routledge, 2013
  3. https://www.pinterest.com/pin/472878029596363797/. Accessed: 2015-05-02. (Archived by WebCite® at http://www.webcitation.org/6YEDVDV8V)