So I had a friend in high school who liked me, off and on, and I had always been curious about whether we should hook up or not. I was afraid to hurt his feelings or make it awkward, but I finally gave up my senior year and figured, fuck it, I'll wing it and see what happens.
We hung out after school on a Friday, and went and ate some fast food, went into a couple of stores, then just drove. He'd been flirting with me coyly up till this point, brushing against me at the record store, bumping elbows on the console, etc. But he wouldn't make any moves because he was under the assumption I was still unavailable. And he was shy as hell. His innocence amused me.
I finally took us to a city nearby where there was a popular parking spot down by a river. After I parked I turned off the lights, swapped CDs (something more appropriate than 12 Stones), and we talked for a while about unimportant shit. Sometimes in the silence I would lock eyes with him, hoping that maybe he'd get the idea and make a move first. I found the more we stared at each other, the more I felt like I was going to spontaneously combust; the look he gave me was smouldering, and I could tell he had desire behind his eyes. It was almost like he was trying to undress me with his eyes, but he didn't let them drift from my face, except when he would look away.
Each look made me a little hotter, and I finally turned off the heater, making a joke about fogging up the windows. When I looked back at him his face was as red as a tomato and he was trying not to look at me. I waited for a moment, then said his name out loud (Drew). He looked over at me, and I leaned in to kiss him. I almost lost my nerve after the first kiss, because of how gentle and sweet he was.
I went back in for a second try, and this time I made it rough; grabbed his face, and gave him a long, hard, bruising kiss. He responded faster than I expected, dropping his hands to my waist and kissing me just as hard. After a while, I straddled him in the passenger seat, eliciting a surprised gasp from him. I kissed him again, then went to his neck, and left a half dollar sized hickey and a few bite marks.
He groaned and shifted, trying to hide the bulge in his pants. I pressed my palm against his erection and listened to his groaning again. I undid his pants, pulled out his penis, which was already good and hard. He was about six inches and pretty thick. I gently rubbed the underside of his penis, circled his head with my fingers, teasing him some. I could feel his hands on my thighs squeezing and rubbing back and forth. I started to stroke his length, slowly increasing speed as his breathing became more labored. At one point I leaned in and whispered into his ear, 'You have no idea how long I've thought about this.' That elicited a moan and I heard him mumble, 'Oh god, don't stop, Lauren.' I kept stroking him, harder and harder, and he finally came, thick ropes that I cleaned up with some napkins.
He closed his eyes, adjusted himself, then opened his eyes to look at me again. I asked if that felt good and he laughed and said that yeah, it felt amazing. Then he looked at me with the simmering gaze again, put his hand at the waistband of my jeans and said, 'Now it's your turn.'