This story is from around 6 years ago. So my friend was sick and had been in bed for several days. One night it was particularly bad so I stayed over at his room to help attend to him and to make sure he didn't die alone in there.
It was very late at night and he couldn't sleep, just tossed and turned. I fell asleep on the couch, woke up about an hour later and he was still trying to get to sleep.
That's when it hit me-we hadn't masturbated together in quite a while (i.e. more than a day for us, at that age!). In fact, he probably hadn't shot any cum in two, maybe three days, I realized.
'Can't sleep?' I asked. 'Nope,' he muttered.
'Well,' I started, 'when's the last time you made your dick spit?' (We used to use funny phrases like that all the time, in private).
'I don't feel like it.'
'Oh come on. You know you can't sleep with all that jizz in you. You need an orgasm, and a big one.'
'It won't be any good. I feel like crap.'
I realized that he was right-if the way he would cum was through masturbation. That night I decided to break a barrier we had never gone beyond.
'Look-I'll do it for you. I've seen you jack off enough times to know how you do it with your foreskin.'
He didn't say anything. I stood up and walked towards his bed and sat down on the edge. He may have felt sick, but there was no way he could resist this! I pulled the bedsheets down. Sure enough his erection was growing and starting to poke out of the front of his boxers.
I grabbed his cock with one hand and started to stroke the skin up and down. It continued to harden. I pulled his tissue box nearby.
As he always did, I started by stroking the main part of the shaft, pulling the skin back and forth over the cockhead, slowly, feeling the cock harden more and more. I reached with the other hand and turned on a lamp so I could see his penis more clearly. I was going to do this by color. His penis head always started out as a pale pink/purple color, and gradually swells outwards (looking smooth and like a balloon), turning redder and redder. In the past he would only finally bring himself off when the head looked as shiny and red as a cherry.
About 7 minutes of stroking and his head was a nice shade of red but still not at that limit. He kept telling me to let him cum now, but I wanted to make sure he shot the biggest load possible. I'd alternate between stroking the shaft, the very tip of his head, and the ridge, which was slick with precum.
5 minutes of this and finally he looked ready to go. I pushed his foreskin back over his head, put my hand over the covered head and began to stroke quickly and firmly. He gasped, which came out more like a sick sounding rasp. I aimed his penis downward at a bunch of tissues I had in the other hand, and kept stroking.
The cumshot wasn't like any others he'd shown before. He grunted. A few small strands dribbled out of the end. Then nothing for 4 or 5 seconds, and then he grunted louder, his body jerked, and let out a very forceful shot. This shot was only medium in length, but very fat (looked 3 times wider than his piss hole). When it hit it made a loud splat and felt heavy in my hand. After that, a couple stray shots squirted out, but it was largely over. I'd always seen long strands of semen, but never a rocket like that. I still wonder how it came out like that. Looking at the tissue I could see he had actually let out an enormous load, easily twice the size of what he normally put out. I guess that concentrated cum rocket was like 3 giant shots in one.
Afterwards his entire body relaxed, I released his cock which flopped to the side of his leg. He sighed heavily. I didn't bother to clean off his penis, and I don't think he cared. He went right to sleep after that.
It was one of the hottest orgasms I'd ever seen, and I wanted to jack off right then and there, but I decided to save it for the morning. I went back to sleep.