Urban Dictionary: 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

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 03, 2014

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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 02, 2012

sail boat

when you take the toilet paper that you wiped your ass with and put it on someones face while they are sleeping.

man!!! did you see Raymond give Sam a sail boat last night? It was fucking awesome!!!!!

by Shadow44_z December 25, 2008

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Sailboat

The mans penis

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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