This is a partially true and partially fantasized story about me and my friend when we were in high school. It started when I was a freshman and he was in 8th grade.
My name is Cory and I'm straight, but I've always been a little curious about gay sex. That's where my friend comes into play.
Matt and I had always been close. We pretty much grew up together and did all the typical guy stuff. Sports, video games, all that. When I was a freshman, I came across my dad's playboy stash and immediately called Matt. He came over and we spent hours looking at them. A few weeks after that I discovered the joys of jacking off. I did it just about every night for a few months before I told Matt about it. When I told him about it, he thought it was pretty funny, but had never done it himself. I had found a porn tape, so I told him we should watch it then he should try it out. We popped it in for a bit, and after a while I knew he was ready. Being the self-conscious boys we were, he went into the bathroom to jack off for the first time. I kind of coached him from outside the door. It still makes me laugh to this day.
Anyway, from there, we got closer. We started watching porn together and jacking off inside our pants, then just going to the bathroom when we were "ready." Soon we forgot about the bathroom and just finished on a paper towel or napkin.
One night when I stayed over Matt's house, we were getting ready to go to sleep. We were in our sleeping bags in the dark, and we both decided we'd beat it before we went to sleep. A little into it, I told Matt about something I had read about...mutual masturbation. We ended up trying it. It was the greatest feeling having someone else touch me. From there, we did the mutual thing a lot.
Matt came over one night to chill in my jacuzzi. We were just sitting around enjoying the hot water when our teenage hormones got the best of us. Matt was kind of worried about doing it outside but eventually the thought of getting caught sounded erotic to us and we started beating it. After a few minutes we switched to out usual mutual routine. That's when something went off in my head and all of a sudden I went down on him. I was going to town on his dick before he could say anything. I could tell he really liked it because he started playing with my hair. Eventually he reached around and started pumping my cock. When I could tell he was getting close, I pulled off and finished him off with a hand job.
Before I could do anything he started going to town on me. He had my whole dick down his throat like an expert. As he was bobbing up and down, I started running my fingers through his hair. I reached around with one hand and started playing with his already hard again cock. With the other hand I started fingering his hole. He kind of jumped when he felt it, but really got into it and started pushing down on my hand. I was lost for a minute before realizing I was about to blow my load. Right as I pulled out of his mouth I started shooting.
I caught what cum I could in my hands. I looked at Matt and said I wasn't finished yet. I spread what cum I had over my dick and turned him around. He looked at me, and as is know, grabbed his ass cheeks and spread them apart. I lined my head up with his virgin hole and gently pushed it. I was having sex with my girlfriend at the time, but I have never felt anything like this before. As I entered him from behind I could tell it hurt. I reached around and grabbed his dick and started playing with it. Soon he forgot all about the pain and I was pumping in and out as fast as I could.
After a minute I sat down and he starting sitting up and down on my dick. He sat down on my dick and I held him down. As he sat there my dick was hitting his prostate, so I started really beating him good. When he said he was ready, I made him get on all fours when I fucked him hard. I continued pumping him as I was going in and out and we ended up cumming together. He went in the water and my cum was dripping out his ass. He looked me in the eyes and kissed me. We started making out until he broke the kiss and said let's do this more often. We've been best friends ever since.
This was my first time ever writing. If you liked what you read, email me at royalbh@hotmail.com