True stroy about my friend Rob. I know it sounds crazy that my friend did not know how to jack off but I think he was telling me the truth. If not, at least we had a good time that day & he suckered me in.
My buddy Rob was visiting one day during summer break. He lived on a farm not too far from our town & I usually saw him only at school. We were sitting in the backyard when Rob asked me if I heard about another guy at school jacking off in the showers. I said no & we laughed about it.
Then Rob asked me what jacking off meant. I thought he was joking with me so I gave him a stupid answer. I soon understood he really did not know.
I was not the type to laugh at him so I started to tell him it was when your cock gets hard & you role the skin up & down until you cum. He had no idea at all about what I was saying & I still could not believe it.
I asked him if he ever cum before & he said he did not think so. I asked about wet dreams, he said maybe but was not sure. I started to wonder if he still had dry ejaculations but he was one year older so I thought he should be squirting by now.
I was starting to get real hard talking about jacking so much, then I had a great idea. I asked Rob if he wanted me to show him how to do it & he said yes. Now I was in all the way with no backing out. I said follow me then we walked down the street to a closed factory where I would sometimes go to masturbate outside.
Out behind the factory was a grassy area where we could not be seen from the street. I sat down on the grass then Rob sat in front of me.
Rob asked why we were there & I told him I liked being naked outside when jacking off sometimes & he just said, 'cool'. I stood back up then dropped all my clothes off to the ground. I sat back down with my stiff cock pointing to the sky.
I was real turned on to be showing Rob how to jack off. I also felt he should know how at his age. I took my right hand & made a circle the size of my cock. I said this is how you should start if you have not done it before. I circled my cock just below the head then started moving up & down. I asked him if he too had just a samll bit of foreskin like me & he said yes. As I kept moving the skin up & down I pointed out how you can't go very high because of not having enough skin. I told him I also used vasoline that I took from my parents bathroom & explained that a gob of greasy vasoline felt nice on your cock because you could stroke it all over instead of just under the head.
I kept it up then that wonderful feeling of cuming started. I told him I was starting to cum & when this happened he should let go of his cock like I just did & wait for the feeling to go away then start again. Rob watched my cock as it moved to every beat of my heart. He asked why did my cock move like it did & I told him. All he said was a long 'waaaaow'.
I was enjoying my teaching time so much then I asked if he wanted to see how to do it with the vasoline. He said yes again so I stopped & put my hard cock in my pants to one side & got dressed. We went back to my house where I knew we would be ok for short time still. Nobody was home for about an hour more.
We went to my room where I hid my vasoline. I locked my bedroom door & opened the window to hear if my mom came home. I got naked again & sat on the floor in front of Rob. I popped off the lube top, scooped out a gob on my fingers then coverd my hard cock end to end.
I told him this was my favorite way to do it & it may be his too. I started stroking nice long full pumps now while Rob watched closely. After a moment he asked when I would cum & I said soon. I came close to squirting once more then stopped while my cock again did it's heart beat dance. I started stoking again & told Rob this time I would not stop when the feeling started & he should get ready.
I slowed my hand pace down to a very slow but steady speed. I still did not want this to end but at the same time I was craving an good cum.
Soon after I knew it was building so I told him to watch now becasue this time I was not stopping. I started to stroke my cock just a bit faster then I was getting close to where I could not stop. I said ok her it is then squirted out a nice few squirts of cum into the air. Rob watched me with a blank look as I kept bucking into my hand even after the squirting stopped.
Once I was done Rob asked if he would also squirt like that. As I was wiping off myself & the floor I asked why does he not try now. I said I would be there to guide him if he needed then he would know how to do it for sure. Of course it was an excuse for me to watch him jack off but I did want him to learn properly too.
Rob did not say a word then just started to get undressed. I sat back waiting to see his hard cock at any moment. He left his underwear for last then out came his cock hard as a metal pipe. I held out the vasoline & he said he wanted to try without it first like I did.
Rob had a bit more foresking than I did & I remarked how I must have had a doctor that did not want me to jack off much then laughed.
Rob started to jack right away & he looked like he had done it before. He said nothing, just jacked away then I asked him how good did it feel. He said it felt pretty good but not great yet. Then I held out the vasoline & he scooped out a bunch. He spread it around like I did then started to stroke again. He only made about 5 full stroked before telling me that it felt real good now. I was getting hard again & scooped out some more for me then went right back to my own cock. I told him to stop when he felt like he was going to sneeze in his cock area. A few seconds later he stopped & then a huge smile came over his face. He said I think it was coming. his slippery cock was moving to his heart beat now too & I told him it must be. I kept stroking without stopping because I had just came so I could enjoy lots of jacking. Rob started jacking again then asked if he should cum soon. I said yes then I heard a car in the driveway. I jumped up to see my mom's car pulling in. We both jumped wiping vasoline all over our bodies to get it off then as fast as we could got dressed. As mom came in the house we were walking outside. I said we would be back soon then she stopped us to help carry groceries.
We each grabbed some bags & they were sliding out of our hands, still slippery from jacking off. Once we were done we flew down the driveway. We made our way back to the old factory then got naked & both stroked our cocks again. This time we were both standing up & after just a few moments Rob said I think it's coming. I told him to keep going then he gave a little noise & started squirting cum for the first time. He squirted real far, much farther than I did. He let go of his cock while still squirting & I said no don't stop so he started again. He only gave about another ten stroked then stopped again saying that was such a great feeling. I showed him how far he squirted & how it was father than me.
I kept stroking my cock for about four more minutes & I explained how it would take a bit more harder & longer jacking to cum the second time. I kept going then my second orgasm came hard while I danced around with just a bit of cum squirting out but for a long long time. Rob asked why I was moving like that & I explained that the second cum can feel better than the first some times. He said he could not wait to do it again.
Later that night Rob called me on the phone to say he came again three more times after he went home & his cock was getting sore. He was whispering in the phone so nobody would hear.
I had jerked off all the rest of that day then into the night as much as I could just thinking about how I had taught Rob to masturbate. My cock was also tender after that day but it was so well worth it.