A Colonial Ages pirate who would literally take down ships in the Central Americas in search for pineapples. A pineapple pirate was under the expression that the East India Trading Company had been smuggling coins and maps through the insides of pineapples. The pineapple pirates didn't last long as this fatal joke got the best of them. They were permanently extinguished when trying to pirate the ship "The Augury" who didn't have any pineapples, but lots and lots of guns.

Used to describe (generally female) imagery that's suggestive, but in a PG-13 sense rather than an R or above sense.