I was about 14 at the time. I went to my friend's house for a regular sleep over. We both started playing video games, like normal 14 year olds. At the time I knew I was not gay. But I always had that small urge that made me curious. I was still a bit new to masturbation. This was also the time I discovered porn. I would masturbate at least twice a day. I just loved the feeling of the cum dripping down my penis.
The day went on and finally came to an end. We both started watching a movie he put on. He had bunk beds, but we were both on the bottom bed. I started to get an erection and I really needed to masturbate. Through the whole movie, my penis was rock hard.
The movie had ended, and my friend was asleep. I was still up, and my erection would not go away. I just could not take it anymore. I got up, went on his computer, and started watching porn. The volume of the laptop was still loud from the movie. As soon as I started watching, my friend woke up. I had my penis in my hand, and we both looked at each other. He told me, 'your penis is pretty big, do you want to compare sizes?' So he took off his pants, and got a ruler. His measured five inches, while mine measured six inches. Without any hesitation, he grabbed my penis and started rubbing the head. It felt so good. With his other hand he guided my hand to his penis. It felt so warm and I started stroking it. I could feel my heart pounding. I told him I was about to cum, and he just went faster and faster. I cummed all over his hand. He wiped some on his penis. This made it easier for me to masturbate him. He cummed all over my hand, and some dripped down on the floor. He them asked 'ever try anal masturbation?' and I replied, 'no I never had.' I wanted to try it though, and I told him I wanted to. He got out some lotion, put some on his hand, and began fingering my anus. It felt so good. My erection was still hard, and I cummed again all over the floor.
We both fell asleep. In the morning he told me if I ever needed help masturbating, come sleep over at his house. It became a regular thing. I enjoyed every minute of it.