When a guy/girl sticks his/her finger in one's ass and then gives them a fish hook with the same finger.
While I was fucking that bitch last night, I gave her a Rusty Scupper, it was awesome!
by Techfall December 4, 2008
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"Scupper stabber" - Slang for a gay man. A scupper is traditionally defined as an opening on the deck of a boat to allow runoff during heavy rains or large waves. Sometimes used to refer to similar drainage for a building.
"Dude, I was in a bar in Boston, when unbeknownst to me, a gay pride parade started marching by...when I walked out I surrounded by 1000's of friggin' scupper stabbers."
by Thor9 September 15, 2006
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Going back and forth between holes on a girl after she shits and while she's on the rag.
Jane's a freak and after she shit she asked me to give her a rusty scupper.
by R. Scupper September 8, 2007
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A bad ass, mo fo, biatch from the kid's book Scuppers the Sailor Dog by Margret Wise Brown who sails the deep green sea having many righteous adventures.
Scuppers the Sailor Dawg popped a cap in yo pirate ass.
by Bin Der Dun Dat August 29, 2008
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When your man fucks you on your period and gives you a bloody facial to finish
Ken: Baby you are so tight on your rag. I need to blow!

Barbie: Baby, pull it out and feed me your Bloody Scupper!
by JayAddie March 5, 2022
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A betting pool to determine which sailor can bring the ugliest woman back to the ship to be judged by the Officer of the Day (OOD).
Hey, we're having a Scupper Contest tonight. A dollar per man.
by Mackinaw83 February 26, 2017
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When a man removes his woman's colostomy bag and proceeds to give her a rimjob via her colostomy hole.
Dude! I was with this lady last night and she wanted me to give her the old Rusty Scupper! Laid her bag by the table and went to town, licking on that side hole!
by BusterHeiman July 1, 2021
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