The first time I ever got really sexual with this girl that I really liked, I was a little reluctant.
I was 16, and I'd been on a couple of dates with this girl. She wanted to go parking, so we found a spot on an isolated dirt road, and we began making out. I fondled her breasts over her clothes, then unbuttoned her blouse and unhooked her bra. She seemed to want that, so I played with her nipples while we continued to make out.
By this time, the outline of my erect cock was clearly visible through my khakis, and she noticed. "That looks like it hurts," she said, reaching down to stroke it through my pants. I was suddenly nervous. What it she didn't like it? What if she laughed? Am I big enough?
She unzipped my pants, then reached through the fly of my briefs and pulled out my cock. "Oh, wow," she said, biting her lip. I guess my apprehension was misplaced. She started stroking it. I stopped her. "Hang on a second," I said, thinking of the mess that would result. I undid my belt and pants and slid them down, then pushed my cock through my fly and slipped the briefs down, pulling up my shirt. She resumed, and it wasn't long before I came. She later told me it was the first time she'd seen an ejaculation. I cleaned up with some tissues, then returned the favor, making her come twice before we had to get her home for curfew. Most of our dates ended up like that over the next few months.