Sailboating

The male equivalent to motorboating, where a woman puts her head between a man's legs and moves her face side to side resulting in the man's penis (or "boom") coming about, so to speak.

I told Gladys to get down there and start sailboating me. She manned my jib all night long.

by Bob Wylie December 7, 2011

Sailboat - sail boat

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

Sailboating

When a man places a strap on backwards as to be able to have sex with two women. The women straddle him from alternate sides while linking hands over the mans shoulders creating a triangle shape. When the legs and as are both linked the man stands creating the shape of a mast and sail. He then has sex with the two women.

I need to work on my leg strength if I want to do some sailboating tomorrow night

by Mypenisisapizza November 23, 2014

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 7, 2011

Sailboatin

When you talk about someone coming over and talkin to yo dime piece then they do

I was chillin with this bitch and i saw a dude creepin so i started sailboatin and said this nigs gonna come over here and talk to you, and he did.

by young co September 16, 2010

sailboating

Sailboating is the act of very very very slowly dragging and flaccid penis across someone's face.

"I love sailboating with my boyfriend. it's the softest 5 minutes of my life."

by allthemarbles June 1, 2015

Sailboating

When one partner spreads the other partners scrotum with both hands forming a "sail", then performs a raspberry by blowing on the scrotum with lips pursed thus creating vibrations.

Jason: If I fall asleep and start snoring, wake me up and I'll go to bed.
Travis: Yeah you'll wake up to me Sailboating you!
Jason: don't you mean.....nah nevermind.

by Greenhower January 22, 2016