The girl is upside down with her head hanging off the bed/couch and she is giving the boy a blowjob. When he cums she keeps it in her mouth and proceeds to spray it all over his body, hence the topping on the cake.
Boy1: dude, why are you all sticky?
Boy2: girlfriend tried something new, the upside down pineapple cake!
Boy1: you need to end that relationship asap.
Boy2: girlfriend tried something new, the upside down pineapple cake!
Boy1: you need to end that relationship asap.
by angelD2010 March 09, 2009
by Beeg Yoshi October 17, 2017
“A Pineapple a day keeps the worries away” While not a popular expression it was first cited in the Hawaiian travel magazine “Aloha Days” in 1965. Since that time it has come into wider usage throughout the islands and the west coast.
by Loveallthepineapples April 19, 2018
by Jeffo 1223123 November 08, 2016
A question that is purely innocent but sounds very perverted. It is used in a conversation between friends when they feel like making other people feel awkward. Can be answered with "Yes, you may lick my pineapple" or "no but you may lick my (other fruit)".
Kayla: "Amy, can I lick your pineapple?"
Amy: "No, but you may lick my cantalope."
Marla: "Dakota, can I lick your pineapple?"
Dakota: "Yes, you may lick my pineapple."
(Random Person): "What?!"
Amy: "No, but you may lick my cantalope."
Marla: "Dakota, can I lick your pineapple?"
Dakota: "Yes, you may lick my pineapple."
(Random Person): "What?!"
by MayILikeYourPineapple? June 24, 2011
euphemism for cunnilingus
by KellyG September 24, 2006
my boyfriend pineapple upside down caked me the other night so i pineapple upside down cake revenged him while having sex
by hehe124 August 11, 2010