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Sailed the Delaware

When your hitting it from the back and stick a flag pole in her anus and put a leg on le bed.
I had this one night stand and I sailed the Delaware on this bitch
by Zebrasocks March 11, 2023
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messy sailor

A play on the stranger, in which the participant drops trow and places himself appropriately on a toilet bowl and then defecates. The participant then places his off-hand (the hand which he or she is not accustomed to wiping with) under his ass cheek until the blood in the hand has been restricted and the hand becomes numb. Unlike the stranger, the participant is not buffing the banana, but rather, attempts to wipe his ass with the numbed off-hand. If feces comes in direct contact through poor coordination or toilet paper misplacement, then the participant has become "messy sailor'd" and thus loses.
After tag-teaming Chavo's sister in the Home and Garden section, Jimbo and Pickles went to the K-Mart bathroom stalls and played a rousing game of messy sailor. Jimbo lost.
by Ginz June 23, 2008
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Related Words

Whale Sail

I was about to bang this fat chick and totally had to lift her whale sail to get to her poon.
by LPrez November 25, 2009
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soapy sailer

when you take a caution sign, put a mop in it, put a tissue on the top of the mop and put soap on the tissue and then put it in a public bathroom stall.
im gonna put a soapy sailer in that washroom
by firedude266 January 9, 2011
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hole sailor

A hole sailor is a fierce pirate who unlike a wholesaler, sails the world in search for the booty hole.
My god, Sharon is dating a total hole sailor again.
by XxHoleSailor69xX June 28, 2017
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Sandy Sailor(TM)

A Sandy Sailor is the same thing as a Sandy Seagull, however the male has foresight to protect his penis with a prophylactic. Therefore, ensuring the pleasurable experience for him upon insertion and a questionable experience for her.
I went to the beach on a romantic date with Nate snd he blessed me with a Sandy Sailor(TM); it was fantastic.
by callmemommy707 August 25, 2017
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french sailboat

When two or more males ejaculate into a fleshlight one after another. The fleshlight is not emptied before passing to next participant.
Hey Rich, this 6 pack of Smirnoff ice would go great with a French Sailboat tonight.
by Wad3th February 6, 2018
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