4Marina 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.
Also they carry sweet daggers.
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.
Then when she died, they had to dress her for burial and found out she was a woman. Then they all felt like dicks.
3Catalina 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 brought about feelings that were strange and deeply confusing.
She may possibly have been the smoothest talker of that era in both the Old World and the New.