Dona Catalina de Erauso was also known as the Nun Lieutenant. She was born in 16th century Spain, and destined by her family for a nunnery. But she rebelled, and escaped at the age of 15 for a life of adventure. She managed to get to South America, where she became a soldier in the Spanish Military, where she was very successful until, after one too many brawls, she confessed her secret on her (she supposed) deathbed. The catholic church accepted her back into the convent (as she was still technically a virgin, despite many affairs with women), until she got sick of the convent life, and went back to adventuring in Spain.
She was born in San Sebastian, Spain, in 1592. She was part of a big family, and a younger daughter, so at the age of 4 she was sent to a nunnery. But at the age of 15, just as she was about to take her vows, she rebelled and escaped. She cut her hair, donned men’s clothing, and decided to seek her fortune. This was the time when Spain was conquering South America. There were enormous riches to be had there for an adventurer. So she became a cabin boy for a ship bound for the Indes, jumped ship in Panama, and ended up in Peru.
In Peru she found a job as a store manager. In the first of many ambiguous sexual encounters, she duelled with a relative of her employer, and as a solution, her employer suggested she marry his mistress (which would have kept both of them handily available for him). But she escaped to Lima where another encounter with a pretty woman led to trouble that Dona Catalina had to escape from quickly.
Luckily, the indigenous population in Chile was revolting, so the Spaniards needed soldiers. Dona Catalina enlisted, becoming a second Lieutenant and distinguishing herself in battle. She met up with one of her brothers there (who didn’t recognise her) and was generally very successful. Sadly though, after three years, she accidentally killed that brother in a duel. They were both seconds to others, and jumped into the fight on opposite sides when the fight started getting dangerous.
Dona Catalina was so devastated that she had killed her brother that she deserted the Army and wandered through the Andes from town to town, gambling, picking fights, and generally gaining a reputation as a serious outlaw. In Cuzco, getting into yet another brawl, she was seriously injured, and convinced she was dying. After receiving the Last Rites, she confessed her gender, and then astonishingly, recovered.
She fled, pursued both for being an outlaw, and for being a woman, until she surrendered to a local Bishop. He had her examined by midwives, who pronounced her both female, and a virgin, so she was placed back in a convent in Lima. Unfortunately communications were better than you might expect in the 17th century, and word came from Spain that she had never actually taken her vows as a nun, so she was tossed out of the convent.
She decided that Spain might be a better place for her, so set out for Spain, to be astonished by crowds hailing her everywhere she went. After a few false starts, she managed to get to Rome to appeal to the Pope for dispensation to continue dressing as a man, and to appeal to the King of Spain for a pension for her military service. Both appeals were successful, and she lived out her life back in South America (in New Mexico) as a mule driver, dying in 1650 at the age of 58.
Her memoirs were published in 1829 (allegedly written in 1626) and translated into English in 1908, with substantial corroborating documentation proving beyond doubt that she did really exist and that many of the bizarre things she claimed did really happen.
She was clearly a transvestite, and had many affairs with many willing women. But it is easy from this historical distance to interpret her life in ways that reflect your own view of a standard life for a woman back then. The most astonishing thing that Dona Catalina did was to live her own life, without regard for the box that women were put in at the time. She seems to have rebelled at every aspect of that box that was possible – dress, gender appearance, sexual relationships, violence, power, independence, religious freedom…
An amazing person, who took her own course through life, and enjoyed the adventure.
Note on pronouns: Different sources on Dona Catalina de Erauso use different pronouns. I have chosen to use the feminine: “she/her” despite the fact that she spent most of her life as a man.