"Jesus, Dean..." He had half the mind to argue against this, say that he was not going to tell a single damn thing, but... "Her name was Cindy, I was sixteen or so and we'd been hanging out for awhile. When I told her we were about to up and move again, she invited me over to her house and..." Well, she gave him a going away that he wasn't going to forget anytime soon, but it had consequently made him pretty unpleasant to be around because they'd had something good going. She was pretty and smart, funny... and Dad wouldn't even let him finish up the school year.

"The best? I don't know, Dean... There were a couple chicks back at Stanford that were- really impressive. I went with this one girl for a little bit, Melissa. I guess her." And his brother might not believe it, but Sam hadn't spent his entire time with his nose shoved in a book, even if he never reached his brother's level of hooking up. "Kinkiest thing... Uh, I never really did the bondage thing, Dean, or half the crap we've ever done together. Been convinced to hook up in a bathroom stall after a few too many drinks. That was pretty kinky, I guess."