“What do you mean, you can’t jerk off?”
As a thirteen year old active masturbator, this seemed impossible. “I mean just that,” was Mike’s quiet reply. He stopped looking at me. “When I play with my dick, nothing happens.”
But Mike was over a year older than me. Of course he must be able to jerk off. I said, “You mean nothing comes out?” Mike mumbled that was the case. I was confused. I had seen Mike naked when we’d changed into our swim trunks in his room, his family having a pool. “But you’re…I mean, everything is normal down there, right?”
“I bet I’m bigger than you are,” Mike snapped back. “And I guess I’ve had wet dreams. I’ve felt sticky stuff in my underwear when I wake up. I just can’t do it to myself.” I was impressed. I’d never had a wet dream although I’d read about them in my Boy Scout Handbook.
Asking Mike what happened when he rubbed his dick, he replied it got hard and then nothing. “Do you do it like this?” making a circle with my thumb and forefinger and moving it up and down.
“No, I usually just rub it with my hand,” holding his open palm down and waving it above his jeans.
“Well, you’re not doing it right.” I was the expert.
“Will you show me how?”
Would I! Beating off was my current favorite thing to do in life. I jerked off multiple times each day. Of course usually I was in my bed or behind a locked bathroom door, but I had also jacked off with friends in Boy Scouts. I’d done it occasionally with a few of my buds on camping trips, either in a tent at night or by finding a secluded place away from camp. My earlier telling Mike about one of these events lead to this conversation. My Scouting jack off sessions had been quick and solo. None of us had to be taught how to jerk off. Exciting and new, I’d love to help Mike learn to do it.
We left the screened-in back porch of my home and headed into my parents’ bedroom. I thought we might lie down next to each other and their double bed made more sense than my single. With my sister at college, Dad at work and Mom doing 1960s mom things, we were alone. I told Mike to take off his clothes. Hesitating, he told me I’d have to strip, too. I agreed, suspecting I’d be naked soon enough anyway. Deliberately we removed our t-shirts, shoes, socks and jeans. We both wore white Jockey underwear. Mike was back to looking me in the eye. “Ready?”
“Yes,” I said, removing my underwear. As Mike did the same, we stopped and stared at each other for a bit. Even though he was older than me, we were similar in height, with Mike only an inch or two taller. He was broader, deeper and stronger than I was, the age difference showing up there. Otherwise Mike was a typical flat-chested young skinny boy while I was maybe fifteen pounds overweight. Call it baby fat. Mike’s dirty blond hair, straight and long for the mid ‘60s, was parted on the right and always falling across his forehead. Mine was dark, curly and usually very short. He was definitely hairier than me all over, varying from fuzzy blond over his arms to light brown around his crotch. I would soon discover Mike had really hairy balls. Nervous, both of us were still soft. “Lie down on the bed and get a boner,” I told him.
Mike did as I asked, lying down on the left hand side of the bed where my dad normally slept. Holding his head up and looking down his body, Mike played with his flaccid dick, both with a single hand and in-between his two hands, rubbing them together as if he was making a clay snake. Soon the cobra arose. He continued to rub his dick with his open palm. “See, nothing happens. Stuff should come out, right?”
“Yes, white sperm. How do you feel? Do you feel tingly inside?”
“No, should I?”
“Try this.” Again, I made a circle with my fingers. “Rub up and down your dick this way.” Mike did as I asked but after only a minute or two, he stopped.
“See, it just doesn’t work for me.”
“You give up too easily. You’ve got to keep going.” Mike went back to jacking his hard dick but stopped again a short time later.
“You’re wrong. I’ve tried doing this before for hours! I’m just not able to jack off.” Exasperated, Mike threw his head back and his arms to the bed.
“Maybe I can.” I reached down and started stroking his dick. For the first time, my hand touched an erect cock not my own. There was no resistance from Mike. Somehow I knew he wanted this to happen. I sat down on the edge of the bed next to his legs and continued to jerk him off. He had raised his head to watch the action, his own hands now rubbing his chest. Breathing more heavily, after a while his head fell back again with his eyes closed. Speeding up the beat, Mike rocked a bit back and forth. He may not be tingling but I sure was, experiencing so many new things as I jacked my best friend’s dick: the warmth of his hardon, the hard edge of his cap as my forefinger crossed it at the top of my stroke, with smaller ridges under his skin slipping past my fingers as they went up and down, even this strange angle of grabbing a cock from below rather than above. I went on high alert, taking it all in. With time I realized that sure enough, Mike’s dick worked just like mine, sensing it was getting ready to shoot. I asked Mike if he felt warm inside. “Fuck, yeah,” was his reply. Wanting Mike to have the pleasure of bringing himself to his first orgasm, I stopped and told him to take over. Mike did so with vehemence, tugging mightily at his dick. In a minute or two, Mike made a series of clipped grunts, ending in a long one as cum flew over his chest. Still being yanked furiously, Mike’s cock shot multiple strings of semen, which speckled his chest and formed pools on his stomach. Having brought his head up off the bed, he looked like he was in pain. His face started to relax as he slowed down his beat and laid his head down. Back to rubbing the underside of his dick with his hand, Mike continued to leak cum. His breathing no longer sounded like he was panting but instead was long and steady. The room was quiet and still. Wow. I wish I could squirt like that.
Keep up the good work Undie. 
And it was Southern California, the other part of the country from you, to answer your question.
).
) just wanted to say i didn't post because i honestly can't remember, then after reading a few entries i decided it was because i don't ejaculate the experience wasn't memorable enough. Then i read your post and decided it must just be that i'm wired wrong!!!!. pick which ever one seems most likely
