10 Historical Figures Who Masqueraded as Members of the Opposite Sex

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Posted in Bizarre | History by on November 22nd, 2011

Across time and culture, humanity has divided roles and responsibilities by gender. While today — in the Western world at least — these roles are not so rigid, in times past they were unassailable. Even so, for some, practical considerations or personal aspirations meant that they had to abandon the role that their chromosomes dictated and take on the identity of the opposite sex.

10. Frieda Belinfante

Frieda Belinfante was an accomplished cellist in Amsterdam and was active in the Dutch Resistance during World War II, forging documents for Jews and bombing the population registry to hinder the Nazi capture of “undesirables.” After the bombing, she was forced into hiding. Disguised as a man for six months, she traveled through Belgium and France to safety in neutral Switzerland. When the war ended, she returned to the Netherlands to discover that she was one of only two survivors of her resistance group. Following the war, she emigrated to the U.S. and resumed her musical career.

9. Amantine Aurore Lucile Dupin (a.k.a. George Sand)

The first female French novelist to become well known, Dupin took on the male pen name of George Sand and also began to dress as a man. She maintained that men’s clothing was more comfortable and practical and used her disguise to enjoy practices that women could not, such as public smoking and attending events from which women were barred. Her transgressions against the upper-class social code cost her some of the privileges she had enjoyed as a result of being a baroness. It seems to have been a trade she was happy to make.

8. Catalina de Erauso

In 17th-century Spain, Catalina de Erauso was forced to enter a convent. Rather than accepting her lot, she escaped, disguised herself as a man and went to America. She took on the name Alonso Díaz Ramírez de Guzmán and joined the Spanish Army. Her disguise was so successful that even her own brother did not recognize her when he served as her captain. She was a brave and bold soldier, rising to the rank of lieutenant. Her life as a man ended when she was wounded in a fight and confessed to a bishop, thinking she was close to death. She survived, however, causing a huge scandal, but her fame prevented any punishment. The pope gave her a dispensation to wear men’s clothes and she rejoined the army where she served until she died.

7. Saint Marina (a.k.a. Mary of Alexandria)

In the 6th century BC, Mary of Alexandria’s mother died. When her father decided to enter a monastery, she put forth the case that she would go with him, disguised as a boy, in order to save her soul as well as his. Convinced, he changed his daughter’s name and the pair went to live in the monastery. Mary stayed in the monastery after her father’s death, maintaining her disguise even when she was accused of impregnating an inn keeper’s daughter. She raised the child as her own for ten years until she was allowed to re-enter the monastery, with severe penalties and restrictions imposed for her “sin.” At forty years of age, she became severely ill and died — and her true sex was finally discovered. The inn keeper’s daughter was reportedly tormented by the devil for her lies.

6. Dorothy Lawrence

In 1914, English-born reporter Dorothy Lawrence was living in Paris, desperate to report World War I from the front lines. Two English soldiers she met in a cafe gifted her with a uniform, so she disguised herself as a man and used forged identity papers to make her way to the Somme. There, she worked laying mines. After ten days, she became ill, and fearing that she would be exposed and cause trouble for those who had aided her, she turned herself in to her commander. She was arrested and interrogated by six generals and 20 officers. Much confusion was caused by her ignorance of the use of the term “camp follower,” which meant prostitute. Fearing that more women would emulate her if the story got out, the Army banned Lawrence from writing about her experiences and sent her back to London. It was only years later that her true story was discovered by historians.

5. Deborah Sampson

While a number of women fought in the American Revolution disguised as men, Deborah Sampson was the first known American woman to have done so. She disguised herself as “Robert Shurtlieff” and enlisted in the Continental Army in 1778. Fearing she had been recognized, she did not report for duty, but successfully enlisted again in 1782. She was wounded in her thigh and forehead in her first battle and, anxious about being discovered, begged to be allowed to die. She was, however, taken to the hospital where her head was tended to, but then left in order to treat her leg herself. This she did with a penknife and sewing needle, but only removed one of the musket balls embedded in her thigh — the other remaining in her leg for life. While still in the army, she became ill, and a doctor discovered her secret but did not betray her. She was honorably discharged on October 25, 1783. Sampson later married and had three children. She spent much of her later years in an ultimately successful fight for equality in back pay and army pensions that she had been denied for being a woman.

4. Charles-Geneviève-Louis-Auguste-André-Timothée d’Éon de Beaumont

D’Éon de Beaumont was a French diplomat from the 18th century who spent 49 years living as a man and 33 years living as a woman. He claimed to have been born female and raised as a boy to provide his father with an heir. He became a spy and journeyed to Russia, where he may have disguised himself as a woman and served as the Empress’ maid of honor. Later in his life D’Eon claimed to be anatomically female and began to dress in women’s clothing. At his death, he was discovered to be anatomically male, although he may have suffered from a hormonal disorder.

3. Hua Mulan

The Disney movie Mulan, as well as many other Chinese stories, have been inspired by the tale of Hua Mulan. The ancient Chinese poem the “Ballad of Mulan” describes her exploits. It is believed that the poem’s events took place between the fourth and sixth centuries. Mulan took her father’s place in the army, fighting as a man for 12 years and receiving many commendations. However, upon completing her service, she refused any honors and instead returned home to a quiet retirement.

2. Shi Pei Pu

The inspiration for the play M. Butterfly, Shi Pei Pu was a opera singer from China who worked as a spy. For 20 years, he conducted an affair with a member of staff at the French Embassy. Throughout this affair, he maintained his disguise as a woman, at one point even convincing the Frenchman, Boursicot, that they had had a child. Ironically, Shi told Boursicot that he was in fact masquerading as a man to please his father! Between 1969 and 1979, Boursicot provided over 500 confidential documents to the Chinese authorities. In 1983, a year after Boursicot brought Shi and their child to France, the ruse was discovered. Upon being informed of Shi’s sex, Boursicot attempted suicide. They were both tried for espionage and sentenced to six years in prison. Shi was released in 1987 and resumed his life as an opera singer.

1. Billy Tipton

Dorothy Tipton became involved in jazz in high school, taking on her father’s nickname, “Billy,” as she began a music career. Originally, Tipton only used the male persona professionally, but by 1940 was living full time as a man, with only a few cousins knowing his true history. She became a well-known band leader and jazz performer, retiring in the 1970s due to arthritis. Throughout Tipton’s life, she had relationships with women, with many of them unaware of her sex at birth. Tipton told her partners that she had been in a car accident, injuring her genitalia and requiring that she bind her ribs. In 1960, she began a relationship with Kitty Kelly. They adopted three sons but separated late in the 1970s. It was only at her death in 1989 that Tipton’s sons discovered that she had been born anatomically female.

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