In late 1509, the political philosopher Niccolo Machiavelli, future author of The Prince, had a disturbing sexual encounter with a prostitute in Lombardy. He later described this incident in a letter to his good friend Luigi Guicciardini.

According to Machiavelli, he was “very horny without [his] wife” and was lured into the home of a washerwoman. Once inside she offered him the services of a woman with “a towel over her head and face”:

“I was now completely terrified, however since I was alone with her in the dark, I gave her a good hump. Even though I found her thighs flabby, her genitals greasy and her breath stinking a bit, my lust was so desperate that I went ahead and gave it to her anyway.”

When their liaison was over, Machiavelli managed to find a lamp and was able to shine a light on the woman:

“My God, she was so ugly that I almost dropped dead… a tuft of hair, half white and half black, the top of her head was bald which allowed you to see several lice taking a stroll… Her eyebrows were full of nits; one eye looked down and the other up. Her tear ducts were full of mucus… her nose was twisted into a peculiar shape, the nostrils were full of snot and one of them was half missing. Her mouth looked like Lorenzo de Medici’s, twisted on one side and drooling since she had no teeth to keep the saliva in her mouth. Her lip was covered with a thin but rather long moustache…”

When the woman spoke to him, Machiavelli was struck by her “stinking breath” and:

“…heaved so much that I vomited all over her.”

Letter from Machiavelli to Guicciardini, December 9th 1509. Content on this page is © Alpha History 2019-23. Content may not be republished without our express permission. For more information please refer to our Terms of Use or contact Alpha History.