The sleepy hollow is when you have a very drunk, passed out girl in your bed. Instead of being the nice guy you normally are, you proceed to insert your penis into each and every hole. While coming to realize she was a complete and utter slut (every hole felt like a hot dog down the hallway). At this point you come to understand she fell asleep in your bed for that reason.
Nathan Pridemore decided to take full advantage of a freshman girl only to realize she was a sleepy hollow.
