My Masturbation Journey

I also taught my new talent to my best friend, who lived about a mile from me.  We frequently slept over at each other's houses, which gave us opportunities to see each other naked and play with our little weenies as we changed into pajamas.  So, after my experience with my neighbor, I began to think about initiating my best friend.  The next time we slept over at his house, we slept in his sister’s upstairs bedroom, which was vacant while she was away at college.  The privacy emboldened me to ask him if he knew how to jack off.  He didn’t but was eager to learn.  We took off our pajama bottoms, and he copied me as I did the deed.  My cumshot was still small, but I described the amazing feeling that went with it.  He continued to rub up and down, but despite his best efforts, he said he wasn’t feeling anything special.  I urged him to keep going, but he still couldn’t get there.  Apparently, he kept trying in the weeks that followed.  One day, he called me and said he had done it in the bathtub and got that “feeling” I had told him about. 

We continued to masturbate together through junior high and into high school, when our interest in girls kicked in.  During a sleepover at my house, we showered together and played “sword fight” with our erections.  I wanted to jack off in the shower, but he wisely suggested we wait and do it in bed.  One night we slept in the guest apartment behind his garage.  I tried to persuade him to do it when we went stripped down for bed, but he wasn’t in the mood.  The next morning, however, he awoke with morning wood and announced, “I want to get naked and beat off!” I readily agreed.  On another occasion, we were playing basketball in his backyard, and we went into the garage apartment to pee.  While watching each other, we both got hard and ended up jacking off.  Around this time, I also learned that my friend had been jacking off with a neighbor our age who tried to get me to do it with him.  What I really wanted was for the three of us jack together, but it never happened. 

Our sleepovers stopped when we were in high school, but after I got my driver’s license we masturbated together once during a long car trip.  I started it by rubbing him through his pants until he couldn’t resist taking over.  We were allowed to drive to the lake by ourselves and use my family’s boat.  A storage room on the dock gave us privacy to change into our swimsuits and more opportunities to beat off.  One summer at the lake, we went out in the boat, jumped in the water with ski belts on, took off our bathing suits, and watched each other masturbate underwater.

Eventually, an unspoken homophobia brought our masturbation sessions to an end.  My friend had started dating and was reluctant to jack off together.  But we had one last session when we roomed together at a conference.  While getting ready for bed, I showed him my hard-on and asked if he wanted to do it.  He wanted to but didn’t think he should.  When I suggested that he could let me jack him off, he decided that was somehow okay.  It was the only time I ever masturbated him to orgasm.

Earlier, while still in junior high, I had one more encounter with my cousin.  At yet another family gathering, he and I masturbated together in my grandmother's attic.  I was fascinated by his red pubic hair and by the fact that he masturbated to orgasm without ever becoming fully erect.