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.

by Greenhower January 22, 2016

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

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

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

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

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

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