Sailing mishap 

Accident involving a sailing yacht.

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

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 !

Sailing the Red Sea by Dutchgit December 16, 2003

QUIT SAFING! 

A Term used By runescape players when Someone is pking and eating (safing) constantly throughout the duel

Person A . Gets hp down to 52 *eats* to 67 *eats* again to 75+ and repeats
Person B . "dude... QUIT SAFING!!"

QUIT SAFING! by pseudonym nim June 21, 2010

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.

sailing for cock 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!

sailing around the cape by Haley Mills February 13, 2009

sailing wait 

How many times a loaded ferry will travel to its destination and back before it it your turn to get on.

It's looks like it's about 3 sailing waits down at the ferry terminal.

sailing wait by SpiderRider3 June 5, 2010

The Ship is Sailing 

When you want 2 people to date you ship them, when they do end up dating, that’s when “the ship is sailing”

Hey! Did you hear that jack and Leslie are finally together?

No way! The ship is sailing!

The Ship is Sailing by MysteryLife13 January 9, 2021