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.

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!

sails fine

Shit that rides smooth. Good shit. Smooth sailing.

Sails fine, man.

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!

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!

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.

Full Sail

1. Extremely impressive or awe-inspiring.
2. Having a high level of commitment to something you are passionate about.

3. Giving one's absolute best, putting in the work and staying focused.

Synonym: balls out
Antonym: mid

We're going full sail on the marketing project with an increased budget and specialists.

Have you seen Jack's new gaming set up? It's full sail.