Sailboat

When you put your penis in a girl and you have your friend jump on a bed to create a wave like movement
Hey Jesse, I just bought a new waterbed... do you mind sailboating for me and Nina?
by Mr. Big Putt August 18, 2019
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Sailboat

A sexual act that requires 3 people. 2 girls, & 1 dude. The guy lays down on his back and one girl gets on his penis and the other girl gets on his mouth. They are facing each other and give each other a high 10 giving the illusion of a sailboat.
Becky & Tanya Sailboated the hell out of Steve.
by BigDaddyK82 November 04, 2014
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Sailboat

A version of motorboating where you blow on a girls tits.
Last night I got her bra off and started to sailboat her tits.
by ktrain11 July 18, 2009
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Sailboat

A dick trick.

The man's (or she-man's) penis is wrapped underneath the ball sack till the penis is pulled perpendicular to the body. This is the "boat." Note, the balls remain behind the dick. Then, the scrotum is then stretched into a triangle where base is held against the penis. Note, the top requires pinching the scrotum and pulling up hard, which can be enjoyable or painful. This is the sail. When completed, the penis sailboat appears to be cruising at about 3 knots across the pubis. It's very popular and appropriate for most parties.
Hey, this party needs a kick, should I bust out a sailboat?

Cody's balls are so big his sailboat would be hella' fast.

I was surprised how much she liked my sailboat trick, then she let me dock my boat in her lady bay.
by ucla sailor January 03, 2012
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Sailboat

Friend 1: "Yo, come check out my sailboat after school?"
Friend 2: "Fuck No!"
Friend 1: "Oh. But i just put a new finish on it."
Friend 2: "Maybe."
by Gary Flongtard December 07, 2011
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SailBoat

A fully strected out ballsack, resembeling the sail on a sailboat.
I cant believe he showed your mom the sailboat.
by tom clancey February 11, 2004
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sailboats

Randy: Ohhhhhhh, I just got beat with sailboats against my two pair, worst beat of my life!!!
by Baker Rawlings January 26, 2006
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