My Masturbation Journey

It wasn't long before I had an opportunity to share my discovery with my next-door neighbor.  One afternoon, we were alone in my house, playing in my bedroom (was my mother at the store?).  I asked him if he had heard about "jacking off."  Like me, he had heard it mentioned but didn't have a clear idea of what it was. We had never been naked together before, but I offered to demonstrate if he would copy what I did.  He willingly pulled his pants down, revealing his little hard-on, and rubbed his penis vigorously. He watched intently as I brought myself to orgasm and was fascinated by my cum.  Since he hadn’t started puberty, I couldn't tell whether he reached a climax. But he obviously enjoyed it — the next day he came over after school and asked if we could do it again!  I don’t remember where we went, but we found a secluded place in the neighborhood and beat off together.  That was the start of several years of frequent mutual masturbation — in the woods, in a culvert under the railroad tracks, in backyard tents, in the tool shed and the garage attic.  My neighbor’s enthusiastic participation was sadly inhibited by his mother who, when she suspected he had been playing with himself, forced him to drop his pants so she could inspect his penis for evidence.  (Unfortunately for him, his penis got quite red when he jacked off and stayed that way for a while after.)  He also shared a bedroom with a younger brother who loved to tattle on him.  So, when we were able to get away for some fun, jacking off was high on his list of things to do.

After we became regular jack-off partners, we "taught" the boy across the street while up in his tree house. My next-door neighbor had climbed up on top of the tree house, and when I followed him to see what he was doing, he told me he really needed to masturbate.  His parents had left him with a babysitter while they went to a football game, so he didn’t need to worry about “inspections.”  I warned him that he was more exposed on the roof than he would be inside the tree house, but before we went inside, I asked him if he was already stiff and squeezed the hard-on that was visible in his jeans.  We went down into the tree house and invited the other boy to join us.  My JO partner taught him to beat off while I worked on myself.  The memory of the two of them masturbating together while I shot my cum out the tree house window is still one of my go-to fantasies.

Our JO sessions came to an end in high school, but we had two chance encounters years later when I was in college. We ran into each other first at a nearby lake where we could stand in the swimming area submerged to the neck.  By that time, I was engaged in heavy petting with my first serious girlfriend (see Part 4) and could describe the fun of playing with her breasts and pussy, as well as her hand-jobs.  That conversation, of course, worked both of us up into a frenzy as we played with ourselves underwater, so we separately slipped off and met at a restroom and jacked off at adjacent urinals.  Two years later we had a similar experience at a local swimming pool.  We talked quietly in the pool about sex and masturbation until we managed to slip away to an empty restroom and masturbate again. By then we were both fully matured and produced generous cumshots.  Despite all the years of beating off together, we only rarely played with each other’s penises, and never engaged in oral activities.