I've got very cool brother...
This happened when I was 13. It was my birthday, and that night my dad came in to give me the birds and bees speech. Being 13, I knew, or thought I knew, a lot, so the 'talk' was more of him answering my many questions: where to put what, what to expect, why I was always hard, etc. He told me there was a way to relieve my constant wood. Telling me masturbation was normal, and that everyone, including him, did it. I wasn't that far into puberty, but I had tried to repeat what I'd heard friends talking about, with no results other than a sore adolescent dick. My dad told me he would have my older brother, who was 16, talk to me more about it.
Later that night, my brother, Brian, comes into my room. He's got a jar of Vaseline, some tissue, and a couple of porn magazines in his hands, and before I could say anything, Brian pulls his shirt and his boxers off, revealing a semi-hard cock, which, after a few quick tugs was sticking straight out. He dangled the tissue over it. We're not a modest family, and I'd seen Brian naked and with a boner, but this was different.
'Hey Little Man, Dad told me to give you a lesson.'
'Like this?' I protested.
'It's alright. It's how I learned. John (our older brother) taught me the same way. Take off those tighty whiteys,' Brian said emphatically as I reluctantly stripped.
Brian's dick was so much longer than mine; thicker, too, and his balls were triple my size, hanging low. He had a lot more hair around his shaft than the little bit I was sprouting. Brian was probably almost 6' tall, blonde hair, and fairly muscular.
'When will I get that big?' I said, pointing to Brian's now engorged cock which he was rubbing.
'Bro, I was probably smaller than you when I was your age. Don't worry, you'll grow. All the guys in the family are packing. John's almost 8 inches. I'm over 6 and a half inches and will probably grow some more,' Brian assured me. 'Average is only 5' or so.' With that, he buried the head of his tool in the Vaseline, sat down on the bed, and then started stroking as he handed me the lube. 'Just do what I do.'
He would make 3 strokes up and down the shaft, then around the head 3 times, with little variation. I mimicked every stroke on my own dick. By now, I was feeling a sensation that I had never had. Brian explained that some guys don't always use lube, but that he liked it better if his dick was real slick. He explained how to visualize screwing the women in the magazines, told me about some good porn websites, and how to sometimes just use your imagination to get yourself off.
'You may not be able to cum yet,' said Brian. 'I hope so, as that's the best part.'
Brian was now stroking with his left hand and using his right to squeeze his ample ball sack, which I noticed even had hair on it! Every now and then, he would rub his chest, nipples, and thighs. I continued to do everything he did.
'I want you to know,' Brian said 'they say 98% of all guys jack off, and I think the other 2% are just lying. You can be sure your friends are or will soon be doing this. It's perfectly natural, and don't be shy about experimenting with some of them. It doesn't make you gay. I jack off with a couple of friends all the time.'
After that, he stopped talking for a few minutes as he started stroking his cock harder.
'Ok, I'm about to cum,' Brian moaned. He arched his back and started rubbing the head of his cock in his palm furiously. The head of his dick was red by now. He then started pounding at it with both hands and started thrusting his hips. Suddenly, he slowed down, lay back on the bed, yelled 'It's a gusher!' and shot cum all over his chest and stomach.
'Keep stroking, let's see if you can do that.' he moaned.
I was stroking furiously, and soon felt my balls tighten, my dick head swelled even larger, and I felt an aching sensation in my thighs. Suddenly, I release a small stream of clear jizz, nothing near the volume of Brian's solid white juice. After another small thrust of cum, it's over, and I felt the extreme exhilaration of my first orgasm.
'Awesome!' Brian yelled. He wasn't the only one who thought it was awesome!
Brian, obviously proud of himself, and already rock hard again, goes for another round. So did I. This one took us both a lot more time, and Brian showed me even more techniques. After that night, I've masturbated at least once a day, sometimes more. Brian jacks off a lot, too, and, now that I've gotten older, we 'lend a hand' to each other 3-4 times a week. Happy Jacking-do it often!