'What do you mean, you can't jerk off?'
As a thirteen year old active masturbator, I considered this 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 you 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.
'What happens when you rub your dick?'
'It gets 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 some 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 house and headed for my parents' bedroom. I thought we might lie down next to each other so 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 couple of wary seconds. Even though he was older than me, we were nearly the same 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 skinny, young, flat-chested 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. He still had the face of a boy, not a man, fleshy for how skinny he was, with hazel green eyes, a strong nose and thin mouth. My head was chubbier, with dark, curly hair, usually very short. Though not doing it today, Mike had a tendency to hang his head and slouch, a dour teenager, all hair and turned down mouth. When he smiled, he stood up straighter and combed his hair back with his hand. I appreciated both sides of him, experiencing those teenage mood swings myself, often hourly. Mike was definitely hairier than me all over, varying from fuzzy blond over his arms to light brown around his crotch. I'd already checked out his dick when we were changing and it looked a lot like mine. 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 complied, lying down on the left 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 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 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, I noticed Mike had started to rock 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 boner, 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 fine, sensing he was getting ready to shoot. I asked Mike if he felt warm inside. 'Fuck, yeah,' was his reply. Wanting him to have the experience 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. After 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, speckling his chest and forming 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 back down. Once more 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.
I got up off the edge of the bed, where I'd remained the entire time, and I went into my parents' bathroom to grab a towel. Back in the bedroom, I found Mike continuing to rub his dick but his head was again up and he wore a broad grin. I gave him the towel and he cleaned himself up. 'That,' he said as he got up on an elbow, pushing his hair off his forehead, 'was totally bitchin'. Wow, man, thank you, thank you for helping me with that. Fu-uck.' Even though he was was obviously very happy, I wondered why he didn't seem totally overcome by the experience. The first time I climaxed, it was like going into a magnificent new room in my house that I'd never seen before. To me, that first orgasm was overwhelming to the point of life changing. Not seemingly for Mike. There is a difference between looking happy and being ecstatic. Once more I wondered if Mike had orchestrated this whole thing. Was this really the first time for him or did he just want to jerk off with another guy?
Leaving me barely enough time to consider this fleeting thought, Mike told me it was now my turn to beat off. Cool. I lay down next to him on his left, toward the center of the bed, and started yanking on my dick, already hard from what had just occurred. With it his turn to watch, he was fully involved now. At one point he asked me if he could jerk me off like I had him. Who me, object? Rolling over onto his side, his hand replaced mine. I got up on my elbows, better to watch my dick getting stroked by someone else. This was two steps beyond mind-boggling. The source of my greatest pleasure, jerking off, had never felt this good before. Too quickly I was ready to cum and took back the jack. Sometimes more of a dribbler, this time I blasted. Moaning, I got spunk all over my belly. I grabbed the towel and wiped it off.
We stayed there naked on the bed for a while, talking little but instead taking time to accept what we'd just done. I'm sure we both said that it was awesome, because it had been.
But then Mike got up and went into my mother's closet. We'd previously explored her underwear drawer and he came back with a flesh colored bra and white panties. Slipping into the panties and putting his arms through the bra, he said he wanted to play mommy and daddy. What in the fuck was this? I was confused and uncomfortable, especially when he lay down on top of me and rubbed his body against mine. As it had remained unclasped, Mike told me to remove the bra. Instead, I pushed him off. This was not my fantasy at all. I got up and started to get dressed. Taken aback, Mike asked me to stop. No, that's incorrect: Mike begged me to stop. We didn't have to play mommy and daddy, he said. Maybe we could just jerk off again? He'd like to try that one more time. I paused and sat in a chair. 'All right,' I said, 'but take that stuff off. That's just plain wrong.' Sorry, Mike, I never wanted to have sex with my mom, or even her clothes.
But I liked the idea of sex with Mike. I once more slipped off my Jockey shorts and we resumed our positions on the bed, me lying closely to Mike's left. We propped pillows under our heads so we could see better, or in other words, watch each other jerk off. We started simultaneously this time, both playing with our own dicks, getting hard, but soon, with only a quick glance at each other, our arms crossed and we traded the jack. This was heaven. It felt so strange to be jacking another cock while my own was being yanked. His dick felt something like mine but his hand on my dick was nothing like my own. It was as if Mike was speaking Japanese yet I understood every word. It felt really good but was also awkward. Our arms constantly bumped each other. We couldn't keep a tempo. Plus Mike seemed to have trouble getting a good grip with his left hand. That I understood. Eventually Mike stopped jacking me and lay back as I continued to stroke him, more firmly and with a sharper rhythm. As I picked up the beat, he started breathing hard and wiggling around much more than just a few moments earlier. He had no problem cumming through my jack. Again he shot a lot. Mike was a squirter. I got his spunk all over my fist and one of his shots landed on my chest. Returning to earth, Mike once more rotated onto his side so he could jack me back with his right hand. He had a confident, man's grip on my cock, swiftly going up and down it, making sure he both caught its tip and hit my pelvic bone. Smiling from the inside out, I'd never been happier. Nobody had ever rubbed my erect dick before this afternoon. I wanted this to last all day. Instead, I came quickly by Mike's hand, this time with my normal dribble all over his fingers after a couple of quick spurts. Laughing, Mike wiped his hand and my sperm on my stomach. I reached over and pressed my sticky fingers against his chest. By this point we were both laughing as we began a brief naked wrestle on the bed. Our dicks rubbed together and nobody cared.
When it was over, we got off the bed and cleaned up for the last time, going into my parents' bathroom and using a wet wash cloth in addition to our new favorite towel. We then got dressed and straightened up the bathroom and bedroom. It was time for Mike to leave. My mom would be home soon.