New Year's Eve

I have read this site for a long time, but this is my first submission.

Clark and I had been friends for a long time, though I'm not sure how. We were as different as two people can be. He was outgoing and athletic, while I was introverted and not coordinated in the slightest. But somehow we became best friends and stayed that way for a long time. We each had other friends who were more similar to ourselves, but we still remained close.

Clark was a cute kid, who turned into a "hot" teenager, who became a ridiculously good looking man. I had messed around a few times with one of my other friends, so I really wanted to make something happen with Clark.

I spent at least a year trying to. We'd play stupid truth or dare, where the truths weren't too special because we knew everything about each other, but all of my dares lent themselves to somehow seeing him naked. But it never worked. A dare to put his dick in a milk bottle happened, but he wouldn't let me see. A dare to sit naked for three minutes happened, but I had to sit on the other side of the chair where I couldn't see him. Finally, one time we had a Penthouse and I could see the outline of his cock in his basketball shorts. I dared him to show me his dick because I "didn't believe the girls were making him hard." He started to pull his shorts down, but only showed me the base of his penis.

During this year, I was so horny that every time we'd have a sleepover I would have a wet dream. I would wake up at some point after an intense dream, and my boxers and myself would be covered in cum. I'd have to sneak up from the basement to the bathroom to clean it all off and then go back to bed like nothing happened in the morning.

Then, there came New Year's Eve, and he spent the night. We slept in my basement on a pull-out couch. Somewhere after midnight, our talk turned sexual. I told him about the things my other friend and I had done, and could tell he was getting horny. He was asking a lot of questions and seemed intrigued. I finally told him I'd show him mine if he'd show me his. He warily agreed to this. We were under the covers, so we both pulled our boxers down and counted to three before pushing the covers down. He had lots of dark hair around his dick and he was about six inches long. Mine had light brown hair and was seven inches. His dick curved up towards his abs, while mine is straight as an arrow. After checking each other out, he pulled the covers back up. 

I asked if I could touch his, and again, he agreed reluctantly. I reached for him under the covers and found his hair-covered legs. I worked my way up to his pubes and felt the heat emanating from his cock. I touched it up and down and started to caress it. He slowly reached out for mine, eventually feeling the length of it. We were both breathing heavy and my heart was racing. His cock felt so good, warm and soft, yet rigid. I felt his spongey head and down to his balls. He did the same for me.

I then said it felt really good if he climbed on top of me and we grinded our cocks into each other. He climbed over on top of me, with the covers still over us, and placed his dick next to mine. He didn't quite get it, as he put all his weight on me instead of just grinding our crotches. That didn't last long, and he flopped back over on his side.

I asked him if I could jerk him off, and once again, he took a minute. He said yes, but we had to turn the light off. I was saddened, as I wanted to look at his dick while I beat him off, but I turned off the lamp next to the bed. He had rolled toward me, and I reached out for his dick again. I found his stomach and worked my way down to his cock. It was hard as can be and pulsing along with his heart. I slowly started to jerk him off, taking my time to enjoy this too. My dick was like stone and screaming for attention, but I didn't dare push this. I thought there'd be a chance for that another time. There was no noise but his heavy breathing and the sound of my arm moving under the covers. I kept a steady pace and could feel his dick start to get harder. I knew he was getting close, so I sped up my rhythm. I felt his dick start to pulsate, and I knew he was cumming. He made some small noises and convulsed along with his cock. When he calmed down some, I let go of him.

I was expecting a total mess on the sheets, but when I felt around, there was no sticky mess. I quickly turned on the light to see where it had gone, but couldn't find any cum. I was just left confused. Many years later, thanks to Solo Touch, I realized that he had a dry orgasm. At the time, I didn't know that was a thing, as I had been cumming for a while.

Looking back, I assume that is the reason he didn't want to get naked and experiment. At the time, I just kept getting mixed signals and thought he wasn't interested in doing it with me.

This was the only time the two of us did something together alone. He still brings it up every once in a while just to make me blush.