by israinpee January 22, 2014
When your friend from Waverly tells you a sad story about the past, you feel like you are riding on the "underground sailboat."
by Zaimejs September 9, 2017
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.
Travis: Yeah you'll wake up to me Sailboating you!
Jason: don't you mean.....nah nevermind.
by Greenhower November 17, 2015
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.
by chappynyc September 20, 2018
by allthemarbles May 30, 2015
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 5, 2021
“ there’s a sailboat in the window”
by Kpoop2316 December 5, 2020