Here's a story about one of my best juvenile jack off experiences way back when I was 13.
I went to my best friend Tom's house to sleep over. It started when I first rang the doorbell. The first thing he said when he answered the door was, 'You hard?'
'Uh huh,' I said, moving to enter. But he blocked me. 'Let's see.'
I paused. I lowered my sleeping bag and overnight bag so as to block any neighbors from seeing - I hoped - and pulled down the elastic waistbands of my shorts and underwear. My terminally stiff boner boinged out. Tom regarded it a moment for effect.
'Ok, come on in,' he said, and turned away. I followed. Slightly annoyed at having to expose myself on the porch, I aggressively reached around from behind him and groped his crotch. He stumbled and made an undignified squeal while I got a good, brief grip on his penis. Yup, hard as a rock.
We were all ready to go because we had been planning this encounter for three days. Just two weeks before, I had jacked Tom to his very first orgasm. We were hanging around talking dirty after school, and it became apparent that he didn't know what masturbation was. In the course of explaining, we just happened to do each other.
Ever since that day, Tom was obsessed with jacking off and talked about it every day at school. Still, we hadn't had a chance to get back together until Tom learned, three days ago, that both his parents and his brother would be gone tonight. He invited me to sleep over, and we had agreed that we would spend the whole time jacking off together.
We went down to the basement rec room, and I set my stuff down. 'Be right back, I'll go get them,' he said as he ran back upstairs. He returned with a treasure worth more than gold to a horny 13 year old - his older brother's collection of dirty magazines.
We sat on the floor and began to devour the first issue, page by page. At that time, I had seen pictures of naked women a number of times, but I had none of my own. Oh, the pussies and titties we saw! We laughed and chatted through a couple of magazines while still clothed. Each page was turned in horny anticipation. I especially enjoyed those extra-hot pictures that were splattered with Tom's brother's cum stains.
Eventually, our shorts and underwear came off. We sat indian-style in our socks and t-shirts, boners sticking rigidly upwards. Both of us had started our pubescent penile growth spurts, but I was at least an inch ahead of him. I couldn't resist fondling myself, slyly I foolishly thought. But Tom saw and grabbed my wiener with both hands, saying 'geez, it's like king-kong over here!' Words I remember exactly to this day!
Still, we avoided stroking in earnest because be knew it would be over too soon. But I had had some thoughts on that subject. I explained: 'We jack each other off at the same time. But you're not allowed to go faster than the slowest guy.' We talked through the ramifications of this strategy, and decided to try it. Tom suggested that we should also both be situated so we were facing a real good bare-naked lady picture. This proved awkward sitting side-by-side, but Tom got an idea. 'Wait here,' he said, leaving.
He returned with a sheet music stand and some binder clips. We each selected our favorite image, and clipped the magazines up on opposite sides of the music stand. I picked a sweet hands-and-knees butt shot (semen streaked, of course), while Tom settled on a slutty spread-legged centerfold. We sat closely on opposite sides of the music stand so that our picture was completely filling our field of view. Upon cue, each took the other in his right hand.
I absolutely melted as the hand reached from under magazine and took me between its thumb and four fingers. But when I grabbed the penis on the other side, it involuntarily spasmed, and a left hand pulled away my right. I tried again, this time lightly with only three fingers - same result. After another pause I slowly, deftly laid two finger tips and a thumb on his shaft while his left hand hovered pensively. Finally, stillness.
We started to stroke each other, but Tom would only tolerate the lightest of motions. I was frustrated that he would also only reciprocate as much, but after all, it was my rule. So I made another: 'New rule: we both keep going until we've both cum.' (I think I wanted to make sure he didn't cum first and lose interest in finishing me.)
I was feeling all cool and superior that I could withstand so much more stimulation than Tom. I kidded myself that I would get bored, and consciously relaxed my penis muscle. For some reason, that song lyric ran through my head - 'Relax, don't do it when you want to come.'
Now I challenged myself to relax my penis completely for as long as I could. But I kept getting the sensation that I was not COMPLETELY relaxed. Yet, I discovered that I could always relax just a little more, creating the sensation of an ongoing tunnel of tingling sensitivity. The song was now stuck in my mind.
As my state of relaxation heightened, the light ministrations of Tom's fingertips bloomed in significance. I felt a tiny pearl of sex pleasure form in the deep base of my penis. I savored it nestling there, seemingly under the complete control of my voluntary relaxation, yet wildly chaotic. Under my concentration, it slowly snowballed into a rushing sensation that encompassed first my genitals, then my entire body.
Suddenly it dawned on me that I was in something of a predicament. I had slipped into a level of intense near-orgasmic stimulation that would be impossible to bear were I not completely relaxed. I knew that the slightest twitch of my cock muscles now would instantly send me spurting. Yet the tingling rush of relaxation pleasure would soon lead to the same place. I held the perfect bliss for second after second...
After an eternity of this pleasure, I suddenly re-noticed the huge picture that was right in front of my face. She was absolutely beautiful, coyly looking around while showing off her pert butt. I had an involuntary mental image of myself buried to the hilt in her sweet pussy. I was shooting huge volleys of cum deep inside her, just like the ones that covered the page.
That did it. The rushing pleasure turned into a delicious pandemonium of rushing fluid; a tidal wave of sperm swelled my seminal antechambers. I was making no end of fits and noises now, and Tom increased his tempo in response. But somehow I maintained my state of pure muscular relaxation and warded off the usual contractions. I had never done it this way before - and it brought pleasure beyond words.
Lacking muscular motive force, semen emerged from my penis tip in a low, continuous fountain. It poured out all over Tom's hand and onto my t-shirt. After a continuous stream that seemed to last several seconds, I lost my will to concentrate and launched the every last remaining drop of cum out of myself in a series of violent contractions. I added several gooey blobs to the babe in the picture along with Tom's brother's, and followed up with many moaning seconds of tender refractory oozing. 'Oh MAN was that awesome!!,' I couldn't help panting. Tom was obviously impressed: definitely the biggest and best jack off ever!
Next, my own rule was invoked against me again as I had to finish Tom off. It was it little weird, but kind of pleasant to do it while his slippery hand continued to manipulate my fading stiffy. It took a long time - I think that any slightly rough motion distracted him into 'starting over.' Finally he orgasmed and a single spherical droplet of completely clear ejaculate formed on the tip of penis. I dabbed it with my finger tip and played with it, making a glistening streamer between my thumb and forefinger.
We really did jack off for the whole evening and then again the next morning. I told Tom about the 'relax, don't do it' technique, but I don't think he really got it. He did go get a tape with the song from his brother's collection, and we listened to it over and over while we wanked each other. Ever actually listened to that song? It's all about jacking off and cumming!