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 18, 2019
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A sexual maneuver where one goes to the corner of the room and does handstand push-ups whilst someone else sodomizes a six-year-old.
Me and my boy Oscar Pendleton totally Michigan sailboated last night with his little cousin.
by marblegoggles August 23, 2010
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Rubber-less anal sex or a person associated on the receiving end of mentioned acts.
'' That girl is a sailboat no rudder"
by toonies July 1, 2010
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A conjunction of a robust mullet and its wearer on a skateboard or other wheeled vehicle, usually on a very windy day.
Steve: You're here early today, Jethro.

Jethro: I left at the normal time, but I rode in on my Sioux City Sailboat.
Steve: How are you going to get home. The forecast calls for almost no wind this afternoon.
Jethro: Well fuck my sister! *thinks real hard* Can you give me a lift?
Steve: No! You haven't bathed in weeks!!
by b-dob December 9, 2009
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A man and a woman pierce their scrotum and labia minora together using a pair of 5 gauge surgical steel rings and then attempt to perform intercourse.
My girlfriend and I just went to Berkley last Tuesday to get our junk pierced and decided to take a ride on the old San Bernardino Sailboat when we got home. It was fun.
by rectacular March 26, 2008
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A sailboat - sail boat, is a boat that driven by sails. Some have 1 sail others 2 sails or more. Thoses that aresearching for a sail boat, used or a new boat, visits the scandinavian website www.scanboat.com where they will find sail boats from all over Europe and especially from Scandinavia.
As Sailboat - sail boat you will find fx. Maxi, Bavaria, Albin boats, Dehler, Swan, Jeanneau, Beneteau etc.
by scanboat December 4, 2011
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The man sits with his legs stretched out. The woman sits opposite the man and places her hips onto him and spreads her legs wide apart. The man puts both hands under either her lower back or legs and draws her to him.
John: My wife wants a new sex position tonight and I'm out of ideas.
Jake: How about the Sailboat tea grinding mill? It's a rare position. I use it sometime with my wife and she loves it.
John: Never heard of it, but I'll give it a shot.
by WouldntYouLike2Know August 18, 2013
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