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John Cabbot sailed for England but was not originally a captain. He was first a male prostitute who sold himself to dirty old men to pay for his schooling. While he was a male prostitute, he had a "pimp" named Reginald Nathan. He was the first known "pimp" of the time, but only delt with male prostitutes. Cabbot was also know to walk the town in the nude to draw men into his cabin and have his way with them. It was said that he made wooded sex toys and forcibly shoved the items up the mens' rectums.

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Q: Italian sea captain who sailed for England?
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