one who's nutsack is so big they can use it as a sail on a boat
we got off the island because it was windy and Gene was an old bag sailor...
by genopetralli August 21, 2015
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1. A term used to describe a promiscuous sort-of-friend or acquaintance.
2. A seasoned lady of the night.
Rita: Did you hear what happened to Sally last night?

Marco: Yeah, she was hanging out with that one guy and ended up going home with him.
Rita: She's such a nut sailor, she did that two nights ago, too with some other guy.
by EhNoThanks January 31, 2014
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When you have a wet dream about a mermaid giving you head.
I had to change Blackbeard's wet woolen sheets this morning, because he said he had dreamt of the gorgeous sailors ghost sucker last night.
by Doncheadle11 August 12, 2011
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(n) 1. a woman with breast implants that goes thru boyfriends, looking for love, like a sailor goes thru rum on an all night binge. Usually due to a complex matrix of self-confidence, immaturity, promiscuity, and daddy issues.
-OMG, did you hear about (name)?

she cheated on her boyfriend.

--Again?! She kept sayin to me that this is the one.

- I know, right. They were together for like ever.

She changed after the operation.

-Ya, she's such a silicone sailor.
by Azn_707 February 7, 2010
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When the toilet paper is clean after a big shit. No evidence on the toilet paper
Wow that was a huge shit better wipe. .... wipes ass.... looks at toilet paper nothing there. ..... Good to go a Smooth Sailor.
by Murseh8r January 23, 2022
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An extreme slamming procedure in drug culture. A male who injects drugs, most commonly methamphetamine, into a vein in his penis slang: pencil" to induce a dopamine intoxication trance. To discover "unexplored waters" of the psyche slang: sailor. Considered a ritual by some participants, it is usually followed by immediate intercourse.
Client: How you like getting high?
Money Boy: I like pencil sailors.
Client: Intravenous?
Money Boy: Nods in the affirmative
Client aside: This rent boy is dangerous.
by rethinker May 6, 2019
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When the girl is giving you a blowjob you pull out when you cum and shoot her in the eye and when she gets up you kick her leg so she walks like she had a wooden leg and a shut eye like she has an eye patch
She looked like a sailor with a wooden leg after i was done with here
by Gabberke December 30, 2022
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