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Craziest person you will ever meet. Smart, funny, loud in a good way, and harsh with the truth. If you need someone to help you with a murder sailyr is your girl. Hates people, especially children, and makes sure everyone knows it. Knows how to keep a secret, along with that like to look at people in disgust.
Person one: Have you seen the new girl she looks like a Sailyr
Person two: She probably is look how she looking at me.... with digust.
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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
Related Words

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.
messy sailor by Ginz June 23, 2008

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
soapy sailer by firedude266 January 9, 2011

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.

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.

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.
french sailboat by Wad3th February 6, 2018