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Miss Cellania
8 Historical Crossdressers: Women in a Man’s World
by Miss Cellania - January 3, 2008 - 4:22 AM

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You may be familiar with the stories of Joan of Arc and Hua Mulan, but they are far from the only women who crossdressed in order to fill roles historically reserved for men.

1. Ann Bonny and 2. Mary Read

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Ann Bonny and Mary Read were 18th century pirates of the Caribbean. Irish-born Ann married a brigand named James Bonny as a teenager and moved from her home in South Carolina to the Caribbean, where she eloped with another pirate, Calico Jack Rackham. She dressed as a man to join his crew. Read was born in London and was passed off as a boy by her mother in order to collect child support from her dead half-brother’s grandparents. After a stint with the British military, she married a sailor and began living as a woman. Her husband died young, and the widow Read once again disguised herself as a man and joined the military. Upon leaving the service, she drifted into a pirate’s life. She met Ann Bonny while serving on Rackham’s ship, and they became close friends, guarding each other’s true identity. The entire pirate crew was captured in 1720, but Bonny and Read both won a stay of execution due to pregnancy. Read died in prison, possibly from childbirth complications. Bonny disappeared from court records. It is believed that her parents may have bought her freedom, but there are no official documents on her fate.

3. Hannah Snell

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Englishwoman Hannah Snell served in the Royal Marines for four years in the 18th century. She assumed the identity of her brother-in-law James Gray after her child died and her husband deserted her. Her unit was sent to capture a French colony in India in 1748, and she was wounded several times without her sex ever being discovered. She revealed her secret to her shipmates in 1750 and was granted an honorable discharge and eventually a pension! Snell made the most of her experience. She sold her story to a publisher, appeared on stage in uniform to tell her story, and opened a pub called The Female Warrior.

More recent women posing as men, after the jump.

4. Frances Clayton

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There are quite a few stories of women serving in the Civil War disguised as men. Estimates range from 150 to 400 such soldiers! Many distinguished themselves, and were even honored for their service after the war. One such hero was Frances L. Clayton, who wore men’s clothing to enlist in the Union Army with her husband. She was wounded three times in battle, and was even taken prisoner by the Confederacy. After her husband was killed, she confided her sex to her commanding officer and was granted an honorable discharge.

5. Charley Parkhurst

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Charley Parkhurst was known as one of the greatest stagecoach drivers of the Old West. Charley was short but strong, and even after retiring from driving, could outwork men half her age as a lumberjack. But after Charley died, those who had known “him” for years were shocked to discover Charley was a woman! Charlotte Darkey Parkhurst was born in New Hampshire in 1812. Dressed as a boy, Charley worked in stables and learned the craft of a driver. She built a reputation as a skilled driver, then fled to Georgia, possibly over the threat of exposure. She moved west to California in 1851, where she again built a reputation as a skilled and talented driver. At least once her secret was discovered, but those who knew kept it confidential to preserve her dignity. After her death in 1879, doctors not only discovered Charley’s sex, but announced that she had at sometime in her life given birth! (image credit: Val Hoover)

6. Dorothy Lawrence

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Dorothy Lawrence wanted to be a front line journalist during the first World War. Instead of enlisting under an assumed identity, she disguised herself as a British soldier and traveled to the front lines. She became a sapper with a mine-laying company! After ten days of laying mines, she became so nervous about her deception that she confessed to her commanding officer and was promptly arrested as a spy. Lawrence was forced to sign an affidavit agreeing not to write of her experiences, which defeated the entire purpose of her war effort. She actually did write of her experiences, but her story was not published in full until many years later. In 1925, Lawrence was committed to an insane asylum, where she lived until her death in 1964.

7. Billy Tipton

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Billy Tipton was a jazz musician who played piano and saxophone. Born in 1914 as Dorothy Lucille Tipton, she was denied a spot in her high school band because she was a girl. Billy was already a professional musician when she began dressing as a man to better blend in with the other musicians, and by 1940 presented herself as a man both publicly and privately. While playing with various bands, she had long-term relationships with several women who never knew her true sex. Although Billy never legally married, she adopted three sons with stripper Kitty Oakes. Neither Oakes nor their sons knew Tipton’s sex until her death in 1989, at age 74.

8. Norah Vincent

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Journalist Norah Vincent went undercover for 18 months as Ned Vincent to discover what the world looked like through a man’s eyes. The result was the book Self-Made Man, and some insights she didn’t expect. You can read an excerpt from the book here.

PS: See the comment section for a note on the usage of the words “sex” and “gender”.

Comments (21)
  1. Interesting subject, great post. :)

  2. I would like to say that this is a great post. I’m a professional crossdresser. Never for anything that noble, but I have been a Drag King in the South East US for over 5 years now.

    I have to say one thing, and its a personal pet peeve of mine.

    Your use of the word Gender is incorrect. Gender, like in languages, denotes masculine or feminine. Not male or female like most assume. Male/Female would be sex not gender. Therefore you can have a masculine gender, and still have a female sex.

    I don’t know why America has that all screwy, most other countries seem to have it set straight. Even people in the medical profession have it skewed. “Gender reassignment surgery” doesn’t reassign gender, it changes sex.

    Sex is between the legs, gender is between the ears.

  3. #2 Sara-

    That is a pet peeve of mine also. I think people are just afraid to use the word sex. It’s pretty silly.

  4. Sara, thanks for the clarification. I wasn’t too sure about the word usage, and what I read about it was confusing. I’ll try to get that corrected.

  5. Neat post. Two questions though. Anyone know what the phrase “drove stage over my madonna” means, on Charley Parkhurst’s gravestone?

    And second, any idea why Dorothy Lawrence went into an insane asylum? Was it because people thought she was crazy because of the cross-dressing, or was she really crazy? People got thrown in the asylums those days for the craziest (heh) reasons; more times than not they were totally sane. Ya’ll should do a post on old insane asylums… I’m fascinated.

  6. Molly, what I read of Lawrence said that the commitment had to do with a rape charge, unrelated to the war. A case of “he said, she said”, apparently.

    I think the gravestone says Mt. Madonna, but I don’t know where that is.

  7. I’m glad I wasn’t the only one bothered by it. Thanks Sarah!

    Also thanks Miss C!

    Still love the post though. Something you may find interesting is reading The First Man-Made Man. True story.

  8. Mt. Madonna is a notoriously difficult traverse in what is now Santa Clara, CA.

  9. Mt. Madonna is a notoriously difficult mountain traverse in what is now Santa Clara County, CA. near the SF Bay Area.

  10. Fascinating….

  11. Another woman in a man’s world? how about John Edwards?

  12. how do women fake the penis? I mean sure you can use prostetics but can that accually be how a real penis feels?

  13. Paul, except for Billy Tipton, this was probably not an issue for these women. They just kept private. Tipton claimed old injuries, which also explained the chest-binding.

  14. Very interesting article. I remember hearing about Norah Vincent a few years ago and meaning to read the book. I’ll pick it up and check it out.

  15. ref. Paul’s question, there are now some extrememly “lifelike” phalluses in terms of both look and feel. Keep in mind that 50 years ago many people never really saw their partner naked, even during sex, and that made the subterfuge much easier.

  16. I’m still confused as how you can hide being a female from your partner. I’m having images of strap-ons going through my head

  17. The famous pirate queen Grace O’Malley also started out cross-dressing as a boy on her father’s pirate ships.

  18. Hello there, Are these pictures copyright or can i be free to use the one on dorothy lawrence? please e-mail me A.S.A.P

  19. I’ve read about some of these women in an “Uncle John’s Bathroom Reader”.

  20. No one else noticed that n°2 is missing?

  21. Yay, The real meaning of \gender\ is getting out in America albeit slowly.

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