As a freshman in high school, a guy in one of my classes told me he could get me two lower level NBA basketball tickets for $40. I brought the money to school and met him at his car, but he didn't have the tickets and said he needed the money up front to go and get them from his uncle. I told him I didn't feel giving him the money without getting anything back, so he gave me 5 of his music CD's out of his car as colateral - (a couple ok ones like Aerosmith, Metallica, Slipknot, etc.) and I gave him the cash.
Unfortunately I never saw him at school again. $40 really wasn't that much, but it was a nice lesson to learn early on.
Anyone else remember their first time getting scammed or just a time you wish you had showed better judgment?