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
Get the Sailboatingmug. 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 April 19, 2018
Get the underground sailboatmug. The act of peeing on a piece of toilet paper from the dry part of the bowl down to the toilet into the water and across the bowl setting it in its maiden and final voyage
by Sklpkl May 30, 2025
Get the the golden sailboatmug. 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
Get the Sailboatingmug.