I've read stories here where people masturbate with their family members, and some were so unbelievable that they had me doubting whether the stories were actually true. I mean, I would never be lucky enough to come close to experiencing these types of situations....or would I??
Last year, my mom married this great guy who had a son a couple of years older than I was. During Christmas holidays last year, 'Donny' came home from college during his winter break. I hadn't really got to know him very well, but he took the time he had off from school and we did things together, to get to really know each other. I was an only child, and so was he, before the marriage, so both of us were excited about our being brothers. He quickly felt comfortable enough around me to take me into his room and show me his extensive porn video collection on his laptop. I told him I had my own stash of porn, and we watched and traded vids quite often. He asked me if I'd ever had sex before, and I told him I hadn't, except for a few groping sessions with some girls in the past. I am kind of a bookworm, and though I fantasize a lot about girls, I have never found myself in a situation where I felt comfortable enough to approach any of them about having sex. Therefore, I masturbate about twice a week to keep my balls from exploding. Donny made me feel much better about it when he told me he did the same thing. In fact, he said he preferred jacking off to intercourse with a girl.
As the days went on, we felt more and more at ease about revealing our most intimate secrets and even fantasies with each other. He asked me if I'd ever masturbated with anyone else, and I told him I hadn't. He looked me straight in the eyes and asked me point blank if I would want to strip naked with him and stroke each other off while looking at porn. I was shocked at first, then nervously laughed and told him that he was full of shit, and that he didn't have the guts to do it. He stood up and dropped his pants right to the floor, right in front of me, with his dick wagging, and dared me to join him! After some prodding (and some horseplay on the bed as he tried to force my pants off), I eventually got naked. We watched some really good cumshot compilation vids he had, and after I had remarked how impressed I was after seeing this one guy shoot a massive load on this skinny girl's face and hair, Donny told me his loads were at least that big. Hell...by this time I was really anxious to see what my step-brother's cumload was really like, so I asked if he would have his orgasm in front of me so I could see it. He said he would, but only if I stroked it out of him myself. After he told me he'd reciprocate after he was done, I agreed, and he stood on the bed as I knelt in front of him, and I reached out my hands and felt the first cock and balls I'd ever felt, other than my own! His cock was semi-hard, but it was still quite large, especially the thickness of the shaft. He put my little dick to shame, let me tell you! I proceeded to stroke his cock as he instructed, and he told me just how to do it to make it feel the best.
About five or so minutes later, Donny told me he was almost to the 'point of no return', and asked me to just let his cock rest on my open hand, and he started to slide his cock along my palm in a slow rhythm. It was drooling clear precum, and it soon made my palm slick as he slid his cock up and down. His eyes were closed, and his hands were rubbing both of his nipples. With a slow groan, his cock began spewing white cum in a steady stream, pooling up in my palm. After maybe ten seconds of this, the flow subsided, and I thought he was done. I mean, he had practically filled my hand with his thick cum, and I started to wipe it off with the sheets, but he quickly told me to get back to stroking him. I took my other hand and stroked his cock as he told me, and in a few seconds, he almost cried out, as his climax hit him hard! He sent ropes of his cum flying everywhere, even hitting me in the face! That was just too much excitement for me to take in, and without even touching myself, I began shooting my own load all over the sheets!
After it was all over, and we came down to earth, we marvelled at how awesome that experience was. I told him I had never seen anyone cum that much before, and asked if he'd had two orgasms. He told me he'd managed, over the years, to control his orgasm so that he was able to ejaculate without having an orgasm. Then he blew my mind! He told me the next time we ever masturbate together, he'd save up his cum for a few days before the event. He said he'd already jacked off once that day, and that he thought his cumload was a rather weak one. I looked at the mess he'd made on the sheets, and on me, and told him the next time, I was going to wear a raincoat....and we both laughed!