Also peg-boy, pegboy. The Straight Dope: 'First, terminology. I’ve seen peg = “copulate�? in a 1902 slang dictionary, and it’s easy to believe the expression was common long before that. But the earliest usage of peg boy cited in the Oxford English Dictionary is from Playboy’s Book of Forbidden Words by Robert Anton Wilson (1972), perhaps not the most reliable source. Wilson writes: “A ‘peg-boy’ is a young male who prostitutes himself to homosexuals; ‘peg-house’, a homosexual brothel. There is an unsubstantiated story that boys in East Indian peg-houses were required to sit on pegs between customers, giving them permanently dilated anuses.�? Whatever you say, Bob.'