Urban Sail

When a breeze kicks up and your umbrella becomes either uncontrollable, inverts itself in your hands, or flies from your grip.

Synonyms: urban kite, umbrella sail, umbrella kite

"Umbrellas are a pain in the ass. Sure, they protect your head and shoulders from the rain, but the second the slightest breeze kicks up, you suddenly find yourself the unwitting mast for an urban sail that, best case scenario, inverts itself in your hands, and worst case scenario, flies from your grip, whips down the street and spears the Pope in the neck." - Tracy V.

Source: Cracked.com, Tracy V. (Invictus99)

by notfeelingcreative June 04, 2014

Dirt sailing

When a man takes his erect penis and in a smooth "sailing" motion runs it along the butthole of a prone person.

The other day Kenny tied a little sail to his dick and went dirt sailing before throwing a piece of eight on her back!

by Habberstamp July 10, 2022

sails fine

Shit that rides smooth. Good shit. Smooth sailing.

Sails fine, man.

by Neverendbro December 15, 2010

Sets your sail

"Set your sail" is a way of say something excites someone.

Ex. Good looking men set my sail.
Ex. What ever sets your sail!

by Young and Fun July 05, 2018

cum sailed

A woman that gives a blowjob to everyone in the room all in a line.

Bitch, you totaly cum sailed that party the other night!

by Yermum69n June 26, 2017

Sail the porch

To spend long periods of time on one's front porch. Usually involves music, conversation and some form of inebriates. May also involve food, especially food produced from a grill.

I'm just planning to sail the porch tonight, you can come hang, too.

by tehamahreha February 28, 2009

Mud Sailing

When you pee and take a shit at the same time. Most notably when you have food poisoning or had a beefy 5 layer burrito from Taco Bell.

Dude how's your stomach? Bro I been mud sailing all day from that burrito.

by Jermeiser February 03, 2016