This was a defining moment in my jacking. It happened one warm Saturday afternoon at a secluded lake when I was 13.
I had been into masturbation for 3 years when I was 13, but was only comming for about 6 months. I was shy about doing it, and avoided talking with my friends although all of us knew that the others were masturbators. This was especially obvious to those of us who swam on the team which the club our parents belonged to formed for teenagers. As I'm sure all jackers know, if a boy is a heavy masturbator when his pecker contracts from exercise it looks puffy. This was obvious to all of the team when we showered after our daily workout. The swimmers were grouped by age, but the groups were mixed in the shower room. Bob, one of the older boys who was 15, began to talk to me after practice when we were showering, and we became quite friendly. His family had a pool at home, so I was invited to swim at his house. This became a more and more frequent event. One weekend when I slept over at his house, we were left to ourselves, and Bob suggested we swim naked. I agreed because we had seen each other naked many times. After we did about 20 laps, we stopped, and were leaning over the pool wall talking to each other when I noticed that Bob was letting one of the jets hit his pecker which was getting hard. When he noticed that I saw what he was doing, he asked why I didn't let a jet hit my pecker. Before I answered, I blushed, but my pecker got hard. The conversation continued.
'Don't be shy. All of us jack off,' said Bob.
'I have a problem doing it out here.'
'Nobody can see us.'
'I know, but, I'd rather not.'
'Come on, let's go inside.'
We got out of the pool, and I saw the biggest hardon I'd ever seen. Bob's penis must have been 8 inches long, easily being 2 inches longer than my 6. When we got into the changing room, Bob sat down on a couch, and began to fondle his pecker. He began by forming an O with his thumb and index finger, turning his hand over so that the O rested against the base of his pecker and pulling it along the shaft until it reached the head. He kept repeating this while I stared wide-eyed.
'What's the matter, don't you warm up before you jack off?' asked Bob.
'No, I just get at it.'
'You should warm up. Do what I'm doing.'
I did, but it didn't seem to add anything to my usual technique.
'Here, let me show you,' said Bob, and reached over and began stroking my pecker like he was milking a cow. It was a new sensation. My head began swelling and soon looked like a red mushroom.
'Keep going,' said Bob, and resumed milking his own shaft.
We must have done about 50 strokes when Bob went to a locker, got out a jar of vaseline, lubed his dick, and handed the jar to me. I lubed up, and we both began a rhythmic classic jacking stroke. Soon Bob was jacking with both hands, and after about 5 minutes started comming. It began with a steady stream of thin white fluid followed by orgasmic spasms. It was such a load, that I stopped and stared. He told me to keep going, and soon I followed him over the edge and into penis paradise. I had the greatest orgasm ever.
After we recovered, Bob asked me, 'How long have you been jacking off?'
'About three years.'
'How often do you do it?'
'2 or 3 times a day.'
'I could tell you are a serious jacker from the way your pecker looks after swimming practice. You should warm up before jacking every time.'
It was good advice.