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."
1. One who controls the ass during anal sex. Typically used in reference to gay males. "Pilot" implies that this is a master of anal sex.
2. A person that is tailgating you on the freeway.
Come over here and fuck me in the ass you Ass Pilot.
*looking in rearview mirror*
Get off my ass you fucking Ass Pilot!!!