The term refers to the Military Academy "West Point" and is usually used by the JROTC's unit local "Woo Poo Prodigy" which is a kid, usually highly arrogant, who is or will soon be signed on with the Academy.
Cadet 2: Who? The one going to Woo Poo?
Cadet 1: Yeah! Look at him, he has the Major kissing his ass! Literally!