Scott was my best friend throughout my childhood and teens. We shared everything. So it was not surprising when we shared our cocks.
Many years ago, my best friend, Scott, and I were playing in his bedroom. We spent countless hours in each other's homes, so being in his bedroom was nothing unusual.
Except on this particular day, Scott asked me if I wanted to see something. Naively, I said "sure." With a big smile on his face, he turned around and lowered his pants and shorts so that I could see his beautiful pink butt. No one had ever shown me their butt before, so this was really exciting. He asked me if I wanted to touch it. Slowly, I inched forward and then reached out and touched his warm skin. I quickly withdrew my hand.
Scott pulled up his shorts and pants, and asked if he could see my butt. Seeing his was one thing, but showing him mine was quite another. I'd never even imagined doing something like this. But I decided that it wouldn't be fair to Scott, if he showed me his and I wouldn't show him mine.
So I turned around and lowered my own pants and shorts - my naked bottom in plain view. He asked if he could touch it. Somewhat reluctantly I said "okay." I could feel his smooth hand rub over my butt cheeks. It felt so good. I wanted him to continue, but we heard his mother call us down for lunch. So I quickly pulled up my clothes. And we went to eat lunch as if nothing had happened.
That was our first somewhat sexual encounter. Over the next couple of years, we continued to do show-me's from time to time. Mostly, we continued to show and touch each other's butts. But as time progressed, we finally showed each other our "wieners," as we called them. At this period of our lives, our wieners didn't do much - but it was fun to see each other's little penis and scrotum. We didn't touch then, just looked.
The next stage is our sexual exploration was fantasy. In our playtime, we used to imagine that we were swimming nude in a large creek that was near our subdivision. Sometimes we imagined that others were skinny dipping with us - his older brother and sister, or some of our other friends. This got me very aroused. I really wanted to do this, but alas, we never did.
Around 13 or so, we would horseplay quite a bit. One game we especially enjoyed was "tickle the wiener." It was exactly what you think it was - we would tickle each other silly, but particularly focus on each other's genitals. By this time, we were starting to get erections and it was really exciting to feel each other's wieners get hard.
By fourteen, we both had discovered masturbation. Initially, we didn't say anything to each other about our private sessions of jacking off. It was just that - a private activity. At first, my ejaculations scared me. I even wondered if I had broken my penis by playing with it! But soon enough I grew comfortable with it. Also, I found some sex ed books my parents had bought when they were first married. They had hidden them in the basement, but I stumbled upon them one day. I moved them to my room and hid them from my parents. One of the books talked about masturbation. It was then I learned that not only did guys do it - girls did too, but just in a different way.
One day, when my mom was out shopping with my little brother in tow, Scott was visiting and we were in my bedroom. At some point our talk turned to sex. He asked me if I rubbed my penis when it got hard. Not wanting to give anything away, I turned the question back on him. He readily admitted that he loved to rub his wiener. He especially loved it when the white stuff came out. At this point I confessed that I did it pretty often too. I also told him that I liked to use either vaseline or lotion when I rubbed my wiener.
Scott asked me how long my cock was. I told him that I didn't really know - that I had never measured it. He suggested that we play our old show-me game and see which one of us had the longest one. Since no one was at home, I agreed. We closed the curtains so no one would see us, then we pulled down our pants and shorts. Both our wieners were still pretty soft. Catching me off guard, Scott reached over and began to lightly tickle my scrotum. I became erect very quickly. So I returned the favor and began to play with his sack too. It had been a while since I had seen his penis. It was no longer a tiny little piece of skin, but a long rock hard rod, surrounded by his beautiful blond pubic hair.
Once we were both hard, we stepped toward each other to measure. It turns out that we were both about the same length, but his was definitely fatter. Scott then suggested we try something. He took my penis in his hand and pushed his penis forward and put them together, head to head. He called this "docking" - I would later learn that this was frotting. He then reached for the lotion that was sitting on my dresser. He squirted a gob of lotion in his hand and then began to stroke both our cocks which were still head to head. Back and forth, back and forth, he began to rub. He rubbed slowly at first, but quickly began to speed up. It felt so good - even better than when I did it alone. I loved that my cock was touching his. I loved that his hand was stroking my shaft. It felt so good that it was like my eyes rolled back into my head. I was in a trance.
Suddenly I felt that warm sensation like I was going to pee. "Scott," I yelled, "I think I'm cumming." "Me, too," he shouted back. He rubbed even more vigorously. We both began to grunt about the same time. Then I felt my hot cum shoot out of my cock. Scott followed also immediately after. Cum shot from both our holes onto each other's cocks, Scott's hand and each of our bellies. Our cocks dripped with cum. It was on the floor, our legs, everywhere. We quickly cleaned up in the bathroom which was next to my bedroom. We got dressed and agreed to tell no one about what had happened.
This was our first, real masturbation session, but it wasn't our last...