I was a sophmore in college. My best friend Don who was a senior, and I were driving around in his car talking about girls at school that we thought were hot. Somehow our discussions always ended up talking about girls and the sex we wanted to have but weren't. It was just another Saturday night where we hoped, but really already knew that we weren't going to meet any girls that would be interested in a couple horny guys.
Don had been at a party the previous day and said that someone gave him a gag gift - a small jar of KY jelly. He had it in the car and showed it to me. Maybe it was my nervousness but I thought it was the funnies thing I ever saw. After we both laughed, we had a minute or two of awkward silence as we drove. Then he broke the ice. In a really unsure, nervous voice he asked if I ever used it. Seeing that he was clearly uncomfortable asking me, I didn't want to embarrass him more so I said, "no but I'm sure it's pretty cool."
Right away he said that of course he never tried it either but agreed that it would probably be fun. Then he asked the question that in retrospect could have either ruined our great friendship, or brought us into a completely new one. He again took a real leap of faith and asked, "do you want to try it?"
My heart was pounding in my chest and the only thing I could get out of my mouth was "like how?"
"You put a little on your hand when your jacking off... wanna try it?"
He had made his intentions perfectly clear and it was now up to me to say yes or no. Before I could really think (or maybe before I tried to think), I blurted out, "yeah, definitely."
I'm pretty sure he had already planned this out. We drove to the street behind his parent's house. It was a new development and only half of the street had houses. We parked at the end of the street where there were just wooded lots. We walked down a few lots and he led me to a spot in the middle of the trees that was pretty well hidden. It was an early fall night, but the sky was clear and the air was getting cool, so we both had jackets on. There was a large log on the ground that we sat on.