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1.
When you shave your pubes and then let them grow for 2-3 weeks, you will start to get ruff prickles around your fanny that resemble the spikes on a pine apple. Then when you go to have sex with someone you do not warn them about it so they are scratched by your hairs, hence the Pineapple Surprise
"Ow Bitch yo fanny hairy" "Pineapple Surprise mother fucker"
by monkey lover237 December 05, 2013
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2.
Pineapple Surprise – Double Shot of Vodka with a pineapple mixer.

Usually consumed in the non-outside window facing pokie room at 9am on a Monday morning of a very dodgy seedy 24 hour PUB.
Oh my god bro... I was so hung to the jesus bone that I had to go and have a pineapple surprise just to tackle the fear before my Monday morning sales meeting.
by Big_Brando_Baby September 01, 2013
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