What is Asspilot?
1.
One who navigates the anal canal: a sodomist. "Asspilot" likens the sodomist to a maritime pilot familiar with local and dangerous waters; ports would retain pilots to go aboard foreign mercantile ships and to safely navigate them to dock or to an anchorage.
"Is he an asspilot?"
"He's gay, if that's what you're really asking."
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