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1.
A pegboy was a young man kept on pirate ships by pirates. This young man was forced to sit on a large wooden peg...all the time. Anyway, this was done so that whenever a pirate wanted to drop his anchor (so to speak) he'd have no problem.
Come here pegboy, I want some of those sweet cheeks.
by Dirty Sanchez August 27, 2003
375 120
 
2.
1. In seafaring, a young male sailor in Her Majesty's Navy, usually of slender disposition who was designated to sit on a peg to keep his anus loose for penetration by the other sailors.
2. In more modern times, a derogatory term denoting a sissy, a fag, or a feminine sailor.
After a long day swabbing the decks, a visit to Billy the peg boy proved to be quite relaxing and enjoyable for Captain Wollingsworth.
by Steven February 28, 2005
175 71
 
3.
a receiver of anal intercourse; someone assuming an unfair share of a burden
Rodney had to drive everyone there AND back, and got no money for gas. He was the pegboy of this fiasco.
by Nigga B April 25, 2003
159 70
 
4.
A young male prostitute, refering to an alleged (and most certainly apocryphal) naval practice of enlisting a young boy solely for the sexual gratification of the crew, and seating him on a peg to keep him "loose."
I usually "drop my anchor" in the peg boy
by Baraldo Rossini November 29, 2006
63 24