The 6 Biggest Badasses Who Lived As The Opposite Sex

6 Billy Tipton

Billy Tipton was a jazz musician from the 30s through the 60s, and like most jazz musicians of that era, a partier and a womanizer. Unlike most jazz musicians of that era, he was also biologically a woman.

Born as Dorothy Tipton, she got into jazz in high school but was forbidden from joining the school band because girls weren't allowed. Because of this continuing pattern of prejudice against women in jazz, and because she liked getting it on with women, she began to dress like a man. At first it was just to fool people for jazz gigs, but she dug it so much that she completely became "Billy Tipton" and declared herself a member of the penis club. Sex change surgery being several decades in the future, Billy tied down his boobs and stuffed his pants.

Incredibly, "he" got away with this through a long-term relationship with a girl. And then another one. And another. Tipton had five long term relationships in his life, and got by each time by claiming that a car accident had coincidentally mutilated both his man parts and his chest, which explained his chest bandages and why they always had to try unconventional sex methods.

A few close cousins may have known about his/her double life, and possibly some of his lovers, but you know who didn't?

Tipton's children.

OK, they were adopted. But still, they didn't have a clue until the 74-year-old Tipton was wheeled into the hospital, dying of an untreated ulcer. In the course of attempted lifesaving treatment, something either popped out, or failed to pop out, or both, and Tipton's son William got the surprise of his life.

After Billy Tipton died, the story went public, and since this was 1989, people were generally more impressed than scandalized. That is how you keep a fucking secret.

5 Shi Pei Pu

French diplomat Bernard Bouriscot went to China in the 1960s hoping for his first sexual encounter with a woman, and got halfway there with Shi Pei Pu, a male Chinese opera singer who pretended to be female.

Obviously the question on your mind is how you can make it all the way through sex convinced that your cross-dressing lover actually has a vagina. You might even speculate that Bouriscot was just closeted and liked having the "I swore he was a girl" thing as cover. You'll be even more confused when you find out that right before Bouriscot was about to leave the country and stay gone for a few years, his cross-dressing lover Shi insisted "she" was pregnant.

Bouriscot, apparently happy to learn that everything he heard in biology class was wrong, left for his trip and stayed gone for four years. When he came back, Shi had a four-year-old kid.

This raises another obvious question: What the fuck was Shi possibly up to with this impossibly complicated charade, and the answer is that he was a spy. A really fucking good one, apparently.

Even when Bouriscot lost sexual interest in Shi, he still kept the two in his life because he wanted to be responsible to his "son" and the "mother" of his "son." While Shi obviously had to make a lot of excuses as to why he had no boobs and why Bouriscot couldn't put anything in his vagina, it is also pretty obvious that these excuses probably didn't have to be very good. In any case, Shi and the Chinese government basically got all the secret documents they could hope for from the diplomat.

Twenty-some years into the relationship, Bouriscot made the mistake of bringing his "family" back to Paris, and thus bringing his cross-dressing lover into contact with less stupid French people. They got suspicious, investigated the relationship, and had a look at Shi's private parts. Both men were convicted of espionage.

Bouriscot tried to kill himself to escape the humiliation but instead ended up being played by Jeremy Irons in a David Cronenberg movie based on a Broadway play about his life. The guy never could get a break.

4 Marina the Monk

The story of Marina the Monk is an old legend, so it's hard to be sure which part is fact or fiction. She was eventually made a Saint by the Cahtholic church, who generally don't go out of their way to associate themselves with cross-dressing, so we'll go ahead and take their word for it on this one. The story goes that when Marina's father decided to go be a monk, she shaved off her hair and joined him. Monks were obviously male-only, but they wear baggy robes and aren't in the habit of poking about at each other's genitals (at least in the more respectable orders) so she got away with it pretty easily for a while.

However, one day she went on a monk business trip and had to stay at an inn. She had the bad luck to be there when the innkeeper's daughter was getting it on with a visiting soldier, and neither of them used protection because it hadn't been invented yet. When the innkeeper's daughter found out she was pregnant, the soldier was long gone, so she blamed it on the cute young smooth-faced monk that had also been staying there.

Marina was in a bit of a bind, but was so set on staying with her dad that she decided to just man up and take responsibility for the baby. The monastery expelled her for getting another woman pregnant with her penis, and she lived outside the gates as a beggar taking care of the kid.

She was so nice about it, though (she was a saint, after all) that the monks let her back in after a few years, but only allowed her to perform the lowliest menial tasks. She raised her illegitimate child (though actually we have no idea what the proper term for their relationship would be) to adulthood, and he became a monk as well.

3 Catalina de Erauso

All right, we don't to be jerks here, but looking at the picture up there we're thinking this probably was not one of the more difficult disguises to pull off.

Catalina de Erauso was a Spanish woman in the 1600s who felt that life was too boring for Spanish women in the 1600s. When her family decided she was to be a nun, that was the last straw and she bolted, looking for adventure in the New World.

Under the name "Francisco de Loyola," she fought as a Spanish soldier, and like most soldiers, gambled, dueled, drank and broke hearts. Noble families everywhere tried to set their daughters up with this dashing young fellow, and she strung them along for all the cash and sex she could get before bolting.

Sooner or later, the game was going to be up, and the canny Catalina decided to beat them to the punch by finding a sympathetic powerful man, a bishop in particular, and giving him her side of the story. The end result was that in return for fooling everyone and running away to fight, drink and screw like a man, and telling everyone about it, she returned to Spain a hero and was commended by the king and even the Pope.

She may possibly have been the smoothest talker of that era in both the Old World and the New.

2 Chevalier d'Eon

Yes, the Chevalier d'Eon was so androgynous the Japanese were compelled to make an anime about him.

The Chevalier, who dressed and acted like a man, was part of an elite French spy corps reporting directly to Louis XV. "He" carried out successful infiltration and spy missions in the Russian court and in England as interim French ambassador.

When a new French ambassador arrived, he did his best to undermine d'Eon as part of a power play, and d'Eon retaliated by publishing a load of French spy secrets while holding back the best ones as a threat. This kept him safe personally but ended his spy career.

Now in retirement, he felt free to let out his big secret: he had been a woman the whole time.

The government was cool with this but demanded that he start dressing as a woman, and he said he was cool with this if the government paid for it, which they did. He went on to have more adventures, participating in the American Revolution, publishing his memoirs and trying to start up a division of women soldiers.

Why did we keep referring to d'Eon as "he" after he came out as a cross-dressing woman? Well, that's the kicker.

After he died, they found out he had a penis the whole time. So... he was what you might call a double crossdresser.

1 Charley Parkhurst

Charley Parkhurst was one of the Old West's legendary characters, maybe because he fit the part so well: Charley was a grizzled old one-eyed stagecoach driver, fearless and hard-boiled. He was also, as you can probably guess, a lady.

Charlotte Parkhurst was an orphaned girl who grew up working in stables and eventually stuck to boys' clothing so she could keep on that path. In Charley's long and adventurous career, she had quite a few close calls, possibly due to the difficulty of hiding her "graciously endowed" rack (as described by the attending physician upon death).

Yet, she managed to keep it up by moving to another location when exposed, or when her likable personality caused friends to cover up for her.

Along the way, she lost an eye to a horse kick or a rattlesnake bite, became the first woman known to vote in a presidential election (52 years before women were granted the vote), became one of Wells Fargo's top stage drivers, and turned to lumberjacking and running a stage business after she retired.

When she died of cancer, the attending physician commented on his breasts, as mentioned above, and also dropped a bomb when he said "further examination revealed that old 'Cock-eyed Charley' had given birth to a child." Holy shit! How the hell did she explain away that year of her life, and why the hell hasn't somebody made a sitcom about it?

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For more badass spies, check out 5 Spies with Bigger Balls Than James Bond. Or find out about some soldiers who went above and beyond the call of ass-kicking duty, in 5 Real Life Soldiers Who Make Rambo Look Like a Pussy.

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