Pussy Sailing

a term that means looking for girls/pussies.
looking for wiling girls to have sex.

"Man, It's been a rough week."
"Yes, we should go pussy sailing."
"Indeed"

by De Jay Hemmingston January 18, 2010

Sailing on the Pumpkin Tide

Refers to becoming drunk while alone in order to enhance one's creative process. Probably originated in the webcomic Problem Slueth.

Person 1: Can you come over tonight?
Person 2: No, I've had some ideas rolling around so tonight is going to be for sailing on the pumpkin tide.

by Analog_man June 18, 2011

sailing

A sport that includes leaping over centerboard housing every time you tack causing lots of bruises and cuts on your legs; especially in a 420 (by the way - it's a type of boat - nothing to do with pot dumbasses) and if you are lucky enough not to be cut or bruised on your legs you probably have a concussion from being too slow to duck during a tack or gybe.

Sailing is the best sport EVERRR

by Sailor_Savvy September 3, 2007

Sailing mishap

Accident involving a sailing yacht.

"You look the same age to me."
"I'M FIVE YEARS OLDER AND IN COLLEGE!!!"
SAILING MISHAP!!!!

by Snake January 16, 2005

Sailing the Red Sea

Shagging a girl that has her period.

" If that means I have to sail the Red Sea that so be it but I need a shag now !

by Dutchgit December 16, 2003

sailing for cock

sailing for cock

v. the act of sailing the high seas for a delicious cock

This act is especially common at frat halloween parties where many females are dressed as slutty sailors. These skanks are clearly not sailing a boat, ergo they are sailing for a nice cock to ride.

Emily was sailing for cock last night, but luckily captain Buckalas was there to give it to her.

by Fast Ed December 10, 2009

sailing around the cape

When a man or woman performs oral sex on a female partner by starting at the clitoris then slowly working the tongue completely around to end up on the anus.

My boyfriend munched my rug so passionately last night and even licked me from my clitoris all the way to my asshole. I just LOVE it when he goes sailing around the cape!

by Haley Mills February 13, 2009