1 definition by Cut Master

Scamming the squirrel is slang for trying to coerse the opposite sex's sexual reproductive organs to have sexual intercourse with your sexual reproductive organs.

Or, for more of a vulgar definition - trying to get some pussy.
Dialogue between 2 friends:

Joey: "Matt, you scamming the squirrel?"

Matt: "Oh yea, I'm negotiating the terms right now!"
by Cut Master October 21, 2007
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