As I said in my last story, I used to have a family friend whom I jacked off with. My other story, the first time we did it, took place before school ended. That summer we spent a lot of time hanging out and jacking off.
One time that really stands out in my mind was the second time that we did it. One day, he was over in the middle of the day. My parents got us burgers for lunch and we had sundaes too. Derek and I ate them downstairs where no one else was (our excuse was that we wanted to watch a different show). We were eating our ice creams when I casually asked him, 'You wanna jack off?'
He answered, just as casually, 'Sure.' We finished up our ice creams and then dropped trou. He grabbed my dick and his hand was still cold from the ice cream. It was a strange but very nice contrast to the warmth of my boner. He started rubbing and eventually I was at full mast.
'What's wrong with your cock?' he asked. Worried, I told him that nothing was wrong with it. 'It points weird.'
'No it doesn't,' I said, slightly offended.
'Yeah it does.' He showed me his erection which stood parallel to the ground. Mine, however, pointed straight at my face. I was slightly disconcerted by the fact that my penis was weird. 'Can you bend it straight?' he asked curiously. I showed him that indeed I could which is what I usually do to jack off anyway. 'Your dick is weird,' he said again.
'Well at least it's bigger than yours,' I threw at his face. It was true, I was probably at least half an inch bigger than his four-and-a-half inches.
'Whatever. Do you have any lube?' I pulled a can of vaseline I kept downstairs for just such occasions and we each smeared it over our dicks and went to town.
I was standing and he was sitting, so I found it amusing to poke him in the face with my penis every now and then. He would swat me away until finally he just grabbed it. Immediately I grabbed his. Nothing was said but we both knew what to do. I began to move my hand up and down his shaft while he stroked my dick like a pro. I didn't want a repeat of last time when I came immediately, so I suggest that I just give him a handjob, an idea he was all for.
I knelt down in front of him and began to stroke him. It took forever though. I quickly lost my boner because of the pain going through my arm from the constant up and down motions. About ten minutes later, he said he was close, pushed my hand off, and quietly dribbled cum into his hand.
'That took forever,' I complained. 'Why's it take forever? I don't take that long.'
'I don't know,' he said. 'It always does.' (I later found out why I lasted so much longer. Turns out he jacked off about 2-3 times a day while I did it every 2-3 days.) Then without warning he grabbed me and started to rub up and down. The feeling was indescribable and I quickly sank to the ground in ecstasy. I was just about to explode when we heard footsteps coming down the stairs. We quickly pulled on our pants and pretended that we had just been watching TV.
It was my dad. 'Your dad's here, Derek,' he said.
'Okay, thanks.' My dad left. 'I gotta go,' Derek said. I found this unacceptable.
'But I'm not finished!' I said belligerently.
'Cry about it,' he said with a shrug. Instead of crying, I whipped out my aching penis and pumped away. I erupted all over the towel on the ground in front of me, moaning the whole time. I stayed stooped over and panting for a few seconds until Derek said, 'Done yet?' and left upstairs. I pulled on my shorts and followed.
Jacking off together was something Derek and I did that entire summer. Most of the time we just did ourselves, but every now and then we would grab hold of each other and spray all over our hands. Remembering the feel of his hand on my dick still gets me going. In fact, it's got me going right now. I think I'll go take care of it.