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

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!

by chappynyc September 20, 2018

Sailboating

Same concept as a motorboating (where you bury your face between a pair of boobs and vigorously shake your head from side to side) except sailboating is slower so you can take it the view.

I wanted to motorboat the girl, but her bazongas were so nice that I opted to slow down and ended up sailboating her instead.

by Lake Partiers May 4, 2021

Sailboating

The tender act of gently laying one's face against another's breasts. Akin to motorboating, but without the noise of the motorboat. Rather than revving your emotional engine, you're drifting peacefully upon emotional waters.

"After the week I had, all I wanted to do was go sailboating and forget my responsibilities."

by dAni5742 April 15, 2025

sail boating

the act of pressing you nose against a flat chested woman and just blowing

Did you motorboat sarah's friend last night? Nope, just went sail boating, there where no boobs!

by Touge_Drifter September 19, 2012

sailboarding

To use a piece of cloth(ex. bedsheet) and tie one end to your longboard, and to hold the other ends up with your hands.

Allows you to skateboard without needing to kick, as the wind pushes you.

Did you guys see that guy sailboarding down the road?

I used my extra bedsheet to sailboard yesterday.

by bombsite March 23, 2011

Sallyboating

Motorboating of the anus or cheeks of the buttocks.

Jacob: What did you do last night Brandon?
Brandon: I went SALLYBOATING all night, bro, with these totally hot babes.
Jacob: Oh, thats just nasty.

by saylboat December 13, 2010