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When you stretch out your ballsack into a cup, pour in a shot of rum, and have a girl take the shot
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If you own a sailboat, it's the wind in your sails.
Yea were gonna head out today, hurricane Wendy left us with plenty of sailboat fuel.
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A sexual act in which a Male/Female defecates on themselves with their legs closed and leaning over an object. Followed by a partner Male/Female that urinates on the fecal matter; causing the feces to slide down between their legs like a Poop Sailboat.
Mr. Van Den Berg's Poop Sailboat caused a rash down the back of his legs, that was visible while he wore shorts.
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When one sneaks onto one of their friends boats, and proceed to wipe their ass all over the sail and/or deck
You hear about what happened in the port? Someone got a ripened sailboat.
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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.
A deeper way to express love or affection. Sailboat is regarded a higher form of love than that expressed in the word "love".
I ⛵️ (sailboat emoji) you
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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.."