This peculiarly midwestern saying actually means "tight-fisted," as referring to money. It seems to be closely related to the saying "so crooked he has to screw his socks on in the morning," said of someone who is untrustworthy or corrupt.
In gay usage, it refers to someone particularly inexperienced (or, paradoxically, remarkably talented) at getting fucked. It was introduced onto the channel by Ziddy as a heretofore unrevealed detail of his I only wanted a piece of cheese, goddamit! story.