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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.
That's where you put it in her twat then finish in her mouth
Sure, I know your sister! We frequently sail up to Ottawa together.
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!