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
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.
by Awesome Brandon March 19, 2006
Randy: Ohhhhhhh, I just got beat with sailboats against my two pair, worst beat of my life!!!
by Baker Rawlings January 26, 2006
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 4, 2014
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
blow-boaters, the worst kind of boaters humanly possible, make boating suck
We are sailboaters, so therefore we have to make sure there is enough blowing going on on our boat.
by blahxxblahxxblah 321456987 January 27, 2008