Girlfriend: "dang boy keep it up you will have enough frequent flyer miles you can get one for free."
Generally speaking it involves any form of anal penetration with the penis.
One can either be the Pilot (giver) or the plane (reciever)
Generally speaking, being the "plane" is a derocitory term used in adolensant hetrosexual males
Use of Brown wings is more commanly reserved to males
Person2: Yeah, but you were the plane!
Person1: No way, pilot all the way, and with a chick!