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

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

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

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

Sailboat farts

When you're on a sailboat and you have no wind, so you fart to make the boat go.

toot toot
Sailboat farts

by Urban Cutester January 9, 2017

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