Sailboating 

The art of coercing a monkey to blow his load into you mouth so you can get high off his jizz.

Bill and Jerry like to go sailboating in the jungles of Costa Rica, because they prefer the old fashion way of getting stoned.

Sailboating by Agent O November 15, 2010

Sailboating 

Much classier than motorboating. To gently blow on a woman's nipples.

Nothing puts Amanda in the mood like sailboating.

Sailboating by BarrettAll November 27, 2011

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.

Sailboating by Bob Wylie December 7, 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

Sailboating by Mypenisisapizza November 23, 2014

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."

sailboating 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.

Sailboating by Greenhower January 22, 2016

Sailboating 

As opposed to the pedestrian act of motorboating, sailboating, shuts off the motor and gets back to nature. First, you drop anchor in preparation for a little sunset rose and cheese. The captain puts his or her face down between the butt cheeks. Whilst the first mate uncorks the wine and cuts the cheese, you just let the wind blow across your face and through your hair enjoying all that nature has to offer.

Chad took up Thadeus on his offer to go sailboating...they had a great time!

Sailboating by chappynyc September 20, 2018