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5.
sort of like motorboating, but you instead of placing your face in between the breasts, one just leans back and "blows the wind into a girls sails" aka breasts less awakward and easier to do in public
hey jess, can i motorboat you?
no way! we're in the middle of a bar, but you can sailboat me!
blow away!
by J BOMMBZ January 27, 2010
8 6
 
1.
A fully strected out ballsack, resembeling the sail on a sailboat.
I cant believe he showed your mom the sailboat.
by tom clancey February 10, 2004
33 17
 
2.
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
18 10
 
3.
pocket fours in texas hold'em
Randy: Ohhhhhhh, I just got beat with sailboats against my two pair, worst beat of my life!!!
by Baker Rawlings January 26, 2006
11 4
 
4.
it's like the eiffel tower, but it's where a guy lays down on the floor, one girl sitting on his face, the other on his dick and the girls high five, thus making the triangular sail shape.
We should totally sailboat that dude
by Awesome Brandon March 18, 2006
20 15
 
6.
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
2 1
 
7.
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
2 2