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sphincter sailor

somone who likes it up the butt... AKA butt pirate
justin beiber is such a sphincter sailor. he will love getting prison fucked
by southpaw365 May 2, 2014
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Creamy sailor

When a sailor is the target of a bukkake while on a naval vessel.
Shipmate- "I can't wait to get underway and be a creamy sailor."
by Dustykeith July 6, 2015
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russian sail boat

Tampon soaked in vodka and inserted in anus
Did you hear Johnny did a Russian sail boat last night
by Westsenecajohnny March 13, 2017
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Baked sail

Similar to a baked sale, a baked sai is a bake sale in which everyone is high and also is on a boat.
A. Did you hear about the baked sail week?
B. No
A. I was like tripping balls and we donated about 15$ to help fight cancer. And we were on a boat.
B. How much did it cost?
A. About 500$, and the cush was about 1,500$
B. Are you KIDDING ME? WHY THE FUCK DIDN'T YOU JUST DONATE THE MONEY IN THE FIRST PLACE
A. Because then I wouldn't have been able to say it was a baked sail
B. when are you gonna grow up and get a job?
A.You think you're better than me because you got accepted into college?
B. I overheard Clair tell my mom that she wishes I was her son and not you
A. No, you didn't
B. I did too, she said that all you ever do is spend the rest of your dad's life insurance
A. SHUT THE FUCK UP YOU PUSSY!
B. Soon the life insurance money is gonna whare out and your gonna have to face reality
A. At least my girlfriend doesn't sleep with the whole fucking town
B. TAKE THAT BACK
A. she is probably cheating on you right now!
B. Your mom said she wishes it was you instead of Bill
A. I fucked Sally
B. You did not you lying cunt
A. Yeah, here's her texts to me
B. You son of a bitch, ILL KILL YOU BASTERED!
A.where did you, get that knife?
B. DIE YOU JACKASS!
B. Oh no, what have I done? I have just committed a murder. I'm going to prison, My girlfriend, my house, my life, it's gone. Life is not worth living anymore. My girlfriend cheated on me, I killed my best friend, and now I'm going to spend the rest of my life in prison. I cant live like this. *cuts wrist.
by not-a-cult-leader May 4, 2018
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star sailor

one who sails the stars.
by Obeloskblue3 January 28, 2019
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Spicy sailor

A blow job that includes the girl sucking on ice and Fishermen's friends beforehand to give a "chilly" and tingly experience for both parties involved.
Yo man, Jessica gave me a spicy sailor last night, Game Changer.

Wtf is that, Some sort of drink?

Nah it's a blow job with ice and fishermen's friends taken prior to the main event.
by Alcoholic Gordan Ramsay March 13, 2019
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The Sailboat Technique

When an circumstanced male grips the tip of his foreskin, and the bottom of his ballsack and tugs in opposite direction, thus creating a triangle shape similar to the sail of a boat.
Dude bro 1: "My girlfriend caught me doing the sailboat technique, she hasn't talked to me in a week."
Dude bro 2: "Yarr, a captain always goes down with his ship.."
by drippy boy March 17, 2019
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