Only the most cut throat of creatures land on the Shadow Mare, the ship that Captain Guld of the Diamond Dog pirates runs. However, there is one exception... The cabin boy. A lone boy from a town called Ponyville some how made his way onto the ship one night, and after being found the captain names this colt his personal cabin boy.

Or, at least that's what Pipsqueak imagined. Ever since his first Nightmare Night, he's been fascinated by pirates. But what happens when his imagination gets the better of him?