It feels good to be able to share my experiences with others.
As I detailed in my other story, 'The First Time With a Friend,' my friend John introduced me to the world of mutual masturbation.
As I said earlier, I grew up with four siblings; two brothers and two sisters. I shared a room with my brothers, who I'll call James and Will. James was three years younger than I, and Will was only a year younger. I had just turned 14 when I started masturbating with John.
I was definitely a lot closer to Will than to James, probably because of the closeness of our ages, but also because we looked extraordinarily similar. In fact, people often said that if Will was taller, he could have been my twin. We both have dark-blond hair, blue eyes and pretty athletic builds (we both played soccer). I knew that Will was just as sexually flustered as I was because of the total lack of privacy in our house.
One day, about a month after I had begun my masturbation adventures, I came home from school early because Will had stayed home due to feeling sick that day. I walked into my room to find Will completely naked, jerking off on his bed, his eyes closed and a look of absolute bliss on his face.
I was shocked to see that, even though he was a year younger than I, Will had a bigger dick than me! He was nearly seven inches, compared to my six. I stood there for five minutes and waited for him to finish up. When he came, he literally blew cum all over himself.
For some reason, I decided to actually be nice to Will, and not embarrass him by walking in on him naked. I quietly crept back outside my house, waited ten or so minutes to give him time to clean up, and then went inside, slamming the door as loudly as I could and pretending like I had just gotten home. Will came out from the bedroom and pretended to be sick. I decided it was a big-brother moment and told him I wanted to talk to him.
I told Will that I knew he jerked off, and that I had just seen him do it. He was shocked because he thought I had come in after he finished. I told him that I didn't want to barge in on him naked or anything. We wound up having a long conversation about masturbation, and finally Will asked how and where I did it. I told him the truth and it shocked him. At first, he got really nervous and asked me if I was gay. I laughed and assured him that I definitely wasn't, which put his mind at ease. He then surprised me by saying that he would like to join in. Since we were so close, I thought it was a good idea and I told him I'd ask John.
The next day in school, I did just that, and asked John during first period. He also thought it was a good idea, but put a twist on it; he said we should make Will do some sort of initiation to be let in. I could kind of tell where he was going with this, and I told him okay; we'll make it up as we go along. He said we could come over that Friday and have a sleep over because his mom would not only be pulling her usual night shift, but the afternoon shift as well, because she was covering for a co-worker or something to that effect.
Friday rolled around quickly, and that evening, Will and I left for John's house. When we got there, John told us to come in. We ate and talked and 'stuff'.
After a while, John said, 'Will, you came here to jerk off. I know that, but first you must participate in a sort of initiation'.
Will was tremendously nervous (He must have thought it was going to be something painful). John retrieved his porn videos, popped them in the VCR and beckoned Will and I to join him there.
John and I sat down on the couch and John ordered Will to strip. Although he seemed really hesitant at first, Will eventually started taking off his clothes. Will then moved to cover his privates from us but John told him to stand at attention, or else he couldn't masturbate here.
Will still seemed really nervous and I just winked at him to try to get him to relax. However, he was still a bit unsure and this was evident by his very limp dick. John then ordered Will to turn around and face the TV. He did, and John told him to watch the movie, but not to touch his penis. Will quickly became mesmerized by the porno (I found out later that this was the first time he had seen porn) and slowly, his dick began to stiffen.
Within a few minutes, his penis was standing at full attention. Even I have to admit, my brother had a well-proportioned dick, with a nice big head, and a long shaft. After a few more minutes of watching, John ordered will to turn sideways so we could see him, and to start masturbating. Will immediately started wanking himself, and he looked like he was enjoying it. John then ordered him to stop, which Will did. It seemed he was really finally getting into this game.
John told me to get up, and then ordered will to undress us both. Will complied and within no time, we were all naked. John and I both sat down, and John told Will to sit between us. Just as I had been, Will was mesmerized by John's uncircumcised penis, and spent a few minutes staring at it. After laughing a bit, John told Will to masturbate both him and me at the same time. Will was shocked, and complained a bit at first. But John was adamant, and pretty soon, Will was sitting right between us jerking us off.
I have to say, it did feel good. Within no time, Will was getting really into it. He tried different grips and stuff on us, but always watched John's penis and the way the skin retracted. After about ten minutes of this, I was on the brink and came, blowing a huge load. John came seconds later, and we both sat there panting for a few minutes recovering.
By the time we recovered, Will was begging John to let him jerk off. However, John said that the initiation wasn't complete. He made poor Will sit there for another two hours, watching porno after porno without letting him jerk off. Finally, John said that he felt bad for Will, reached over, grabbed Will's cock and started pumping it. Will, being extremely horny, didn't care, and let John carry on. Within two minutes, Will blew a massive load, creating a huge mess on the floor. The orgasm was so strong that he dropped to his knees and just lay on the floor for a few minutes afterward.
After a little while, we cleaned up and went to bed. This was the beginning of our masturbation club. We had many more experiences, some of which I will detail in later entries.