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

sailboat in the window

A statement made to bring attention to a person who hallucinants throughout the day

“ there’s a sailboat in the window”

by Kpoop2316 December 5, 2020

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

douche sailboat

Exceeding the limits of being a douche canoe but not douche yacht level quite yet.

"You're a douche sailboat Chad"

by israinpee January 23, 2014

underground sailboat

When your friend from Waverly tells you a sad story about the past, you feel like you are riding on the "underground sailboat."

Thanks for bringing up that trip to Malmo, now I'm all chilling on the underground sailboat!

by Zaimejs April 19, 2018

The Sailboat

When you take a shower curtain rod and put it in the girls ass with the shower curtain still attached while you’re fucking her from behind causing the shower curtain to flap wind.

I rode her like the sailboat.

by ACSailer April 26, 2025