Sail close to the wind

verge on indecency, dishonesty, or disaster

Here's a sentence using "sail close to the wind":

The politician's campaign ads sailed close to the wind with their negative attacks on the opponent.

by Arminkshipper July 25, 2024

Sail boating

The act of farting against the scrotum during Anal sex, turning it into a spinnaker sail.

After a delicious taco Tuesday meal, she took me sail boating

by TeamCook January 21, 2019

Sex sails

A sexual play on the saying ‘wind in my sails’.

Ernie paused to turn up the television volume, which really took the wind out of my sex sails.

by Snake Lovin’ Gurl January 18, 2018

Sail Hypixel Guild

a good guild with active members

Oi mate I jusy joined the Sail Hypixel Guild, it's got lots of active, friendly members and it has decently low requirements, aswell as a decently high level!

by SailorStifi April 14, 2022

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 4, 2014

point of sail

point of sale: in an establishment that sells goods or services, the location at which payment for goods is made.

sail: the power harnessed by a sail or sails, or the use of this power for travel or transport.

point of sail: the location at which a sail harnesses power.

"Let's go to a 'point of sail'." - says a pirate

by [e-mail] February 9, 2013

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 9, 2022