Often used in cocky masculine conversation. Often found more humorous when talking in an overtly stereotypical Italian-American accent while making radical hand gestures up and down one's thigh in order to demonstrate it's size.
Bart: "How 'bout that little blond broad? You gonna hit that tonight?"
Johnny: "Oh, Bart! What'da you think?! You know I'm gonna go back to her place and give her my Chrysler Building!!! Ehhh...ohhh!"