Variation 1: When a male's private part is so long or the shorts (and underwear) are so short, that the male private part dips below the bottom of underwear and is visible below the bottom hem.

Variation 2: When a man's private parts are so long that they dip into the water in a urinal.
Var 1: "Dude, you need longer shorts. You're weighing anchor."

Var 2: "Man, I hate when I weigh anchor. That urinal water is disgusting."
by PJeigh June 17, 2011
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While engaging in missionary style intercourse, the Male will insert his scrotum, entirely, into the anus of the Female to act as an anchor.
Sharonda gets so slippery you're gonna need to weigh anchor in that berth.
by Chaosfish March 22, 2019
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To Weigh Anchor in Poo Bay is another term to describe the plundering of an anus (male and or female) by some one who thinks they are a modern day Black Beard.
This works best, whilst wearing a pirate hat, or for the more extreme/adventurous "Weighing Anchor in Poo Bay" whilst having a parakeet on ones shoulder, which can end up in a very sticky situation...
Mac: I totally "Weighed Anchor in Poo Bay" last night! She loved it!

Ross: Sick! Did you try it with Becky's Parrot on your shoulder!?

Mac: Hells yea! she got abit pissed about the parrot shitting on her back though...
by ZOMGBBQ November 15, 2010
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