My first jackin buddy was a great one!
I was in high school when my family moved to a nice house in Southern California. I was a regular masturbator between the sheets, and when we moved into our new house with a large yard, I discovered the thrill of masturbating outside, naked. At first I had few friends, and so would come home from school to an empty house (my mom worked, too), strip naked, and masturbate in the garden.
Our spanish-style house had a flat roof, and I went up there to lie naked and get a sun tan. Safe from intrusion, I went there frequently to masturbate, and my little spot there was stocked with lube and tissues and magazines. At about that time I discovered the fun of anal pleasure while masturbating, and I also stashed all the different toys I'd collected for that purpose, as well.
I've always been on the shy side, and so making new friends at school was a little slow and painful, and anyway I was enjoying masturbation like I'd never done before. The freedom to walk around naked, and to masturbate outdoors was tremendously enthralling, and so when I finally struck up a friendship with another boy, I naturally wanted to share it with him-I didn't think it would be strange or weird to reveal my secret garden delights. And so a few weeks after getting to know Bobby, I invited him over to my house after school.
I showed him around the house, and then out in the garden, and felt myself growing excited. I took him to a little arbor in the garden, and behind that, led him to a spot in some bushes.
'I like to jack off here when my mom's not home.'
'Oh cool,' Bobby said, 'I wish I had a yard like this.'
'Do you like to jack off?' I asked.
'Yeah, just at night, though, I think I'd be too scared to jack off outside. Somebody might see me.'
'Yeah, but it's safe here. Anyway, I have a place on the roof, too. Do you wanna see?'
Bobby and I climbed up to the roof, up above the garden, above the street, higher than any houses around, and hidden by the parapet wall. Over in the corner were a beach towel, and my little stash.
I always felt horny when I got up on the roof, and there with Bobby I had an overwhelming urge to get naked and play with my cock in front of him. I don't know if I even said anything to Bobby, or needed to-Bobby was feeling the same urge. In a heartbeat I was naked on the towel, spreading lube on my cock, and watching Bobby pull down his pants.
Bobby was a short guy, kind of small. If he were a girl you would say 'petite'. His cock and balls were large, bigger than mine, as large as any I remembered seeing in gym class. We both began masturbating. We hadn't talked about masturbation before that day, and hardly spoke about it then.
Somehow we knew instinctively that both of us loved to jack off more than about anything else, and our friendship, our attraction for each other, had been headed for this moment, naked and stiff in front of each other, from when we first spoke to each other after class.
My eyes were glued to his cock, his hand, his balls bouncing with each stroke, and I was filled with joy to be showing myself, to be stroking in front of him, to have another boy up on the roof, legs tense with pleasure, stiff cock and face intense with the same passion that I felt masturbating. Bobby was close to cumming, and move awkwardly closer to me, slight noises coming from his throat. He slid over, slid close to show me his cock, to cum for me, to show me his cum. His tip was wet with precum, and his cock filled my eyes, large, pink and purple head sticking out from his fist. Breathing faster and harder, we both were on the edge for what seemed forever until Bobby slipped moaning into orgasm, and cum began shooting from his dick onto me, and at the sight, I came too, hard and wild.
Bobby was my first jacking buddy, and I was his. Twice a week Bobby could come over to my house, and we'd go up to the roof, lay naked in the sun and masturbate. Perhaps the third or fourth time on the roof we did what came naturally, and stroked each other. It was awesome to feel another cock, another cock that loves to be stroked, in my hand. And Bobby shot TONS of cum, much more than I, and I was fascinated and thrilled with how hard he would shoot.
We did this regularly, laying out on the roof next to each other, facing or, sometimes, in each other's lap, legs wrapped around waists and cocks touching. Then sometimes, when I was sure my mom would not be home, we'd run naked downstairs and jack in the house-especially in front of the full length mirror. I guess we were mutual exhibitionists!
We jacked a whole lot together that year, and the next year a new high school opened and we were in separate schools, so it was harder to get together. We spent some Saturday afternoons on the roof, though, and also in some bushes near his house. He was such a great buddy, and I'll never forget the feel of his cock!