Story of my first mutual masturbation experience when I was 14
As a 14 yr old boy I was perpetually horny. A friend of a friend that summer had stumbled across a stash of porn magazines (not sure where or how he got his hand on them) and it quickly became known to several of us that they were being kept hidden underneath a footbridge on the other side of town. One day I ventured over with a group of friends and we found a trash bag filled with these magazines, and we spent the better part of the afternoon devouring our first-ever views of naked women in various poses (mostly they were Playboy and Penthouse magazines, but a few graphic ones as well). While I'm sure my friends were as horny and hard as I was, no 'circle jerk' or masturbation contest took place. We all took off for home later in the day, and it would probably be safe to say all of us ended up wildly masturbating in our rooms that night before we went to sleep (I know I did!).
A few days later, early in the morning, I pedaled my bike back to the bridge and no one was there. My plan was to 'steal' a few of the magazines to take home with me for my own personal viewing pleasure. I picked two of the better ones out of the pile, stuffed them down the front of my jeans, and hopped on my bike and went home (ever try riding a bike 3 miles with an erection and two magazines stuffed down the front of your pants? It ain't easy...).
When I got home my dad had already left for work, but my mom was home all day and her car was in the driveway. I dumped my bike in the driveway and headed through my backyard towards the woods behind our house (we had about 5 acres of woods back there we would play in all the time). As I was walking through the yard a kid from up the block, Scott, was riding by on his bike and shouted at me, asking me what I was up to. Scott was about 12 at the time (two grades below me) and I knew him, but we didn't really hang out that much together. I told him I was going for a walk in the woods and he asked if he could come. I was a little peeved because I had planned on finding a secluded spot to look at the magazines and jerk off but I told him he could come along (hoping he'd leave after a little while so I could 'do my thing').
We walked down the main path in the woods for a couple of hundred yards, and I figured it would be cool to show Scott the magazines. I stopped and told him I had something really excellent to show him, and he couldn't tell anyone about it. I pulled the magazines out of my pants and handed him one, and he had the same reaction I had the first time I had seen them a few days before: surprise, shock, amusement and excitement all wrapped into one. We commented on the size of the 'tits' of the women in one magazine (it featured only large breasted women) and talked about what it must be like to see and feel a real girl's tits and pussy. I showed him the magazine I had that had pictures of full intercourse and oral sex (no orgasm shots though). I was hornier than hell just looking at the pictures and was dying to jerk off and I looked at Scott and was pretty sure by glancing at his shorts that he had a hard on like me. I wondered if he masturbated yet.
I figured that since he was looking at the magazines he wasn't going to leave anytime soon so I decided to just ask him. He looked at me like I had 2 heads when I casually said, 'So, do you jerk off?' He was like, what's that. I told him that's what guys do when they're horny, and it feels really good. I told him I did it sometimes, and when I saw pictures of naked girls I got horny, like now. He was pretty much, oh, OK and that was it and he kept looking at the magazine. So I told him that I could show him how to do it if he wanted he said he didn't know, it sounded kind of queer. I assured him it wasn't queer, that it was cool and it would be fun. So finally he said OK, and I told him we should go a little bit deeper in the woods so no one would catch us.
We walked about 50 yards off the main path to a little clearing where me and some other friends would play cards sometimes. It had a few huge logs in kind of a semi circle for seats, and a bunch of stones in a circle that we would make a fire in. I sat on one log and Scott sat on the one right next to me. I didn't say anything and just started to rub myself right through my shorts and underwear while looking at the pictures. I told Scott it felt really good and he should try it. He put his hand on the front of his pants and he started rubbing and I asked him if it felt good and he replied really softly, 'Yeah...' I told him it's better when your pants are off and I stood up and unsnapped my shorts and pulled them and my underwear down to my ankles. He just stared at my cock as I sat back down on the log (not terribly comfortable but I didn't care). I spread my knees apart a little, which gave Scott a complete view of my erection and balls, and I started to jerk real slowly. I sighed a little bit and told him how great it felt and he should try it. He told me maybe in a little bit, and he kept rubbing himself through his pants while alternating glances back and forth between my cock and the magazine he was holding.
After about 3 minutes he stood up without saying anything and unzipped his shorts and pulled them down, leaving him standing there in his t-shirt and underpants. His cock was pressed against his underwear, and he hesitated before he finally pulled them down too. His cock was a lot smaller than mine, and he only had a little bit of pubic hair around it, but he was just as hard as I was. He sat back down and grabbed it awkwardly, squeezing it and pulling on it very hard - it actually looked painful to me. I told his he should do it like me, and I showed him how I did it more gently and slowly. In no time he got the hang of it and told me I was right, it DID feel really good. I told him if he did it long enough he would come, and he wanted to know what that was. I told him it was sperm, an orgasm, and he said he understood. So we sat there jerking and looking at the pictures for a few minutes, mostly in silence, until I said I heard it was awesome when someone else played with your dick - it's called a hand job. Again he said that sounded queer, and I told him it was only queer if guys kissed and stuck their dicks in each others butts and that lots of times guys gave each other hand jobs and it wasn't queer (I didn't know if that was true or not, but I wanted to find out what it was like to have someone else jerk me off).
I must have been convincing, and he must have been totally horny, because he pretty quickly said, OK let's try it. I didn't want him to change his mind so I immediately moved over right next to him on his log (hopping because my pants were around my ankles hahaha). There we were, our pants and underwear around our ankles with raging boners sitting next to each other, each holding a porn magazine. He was on my left, I was on his right. I closed up my magazine and dropped it on the ground. I very nervously moved my hand over towards Scott's lap and as I did he leaned back with both hands propped on the log. His cock was sticking straight up and when I took it in my left hand I noticed two things immediately: it was very warm, and the skin was very smooth (he was cut, like me). I started to jerk him up and down, and it felt weird at first but really cool too. He let out a long sigh and said, 'Oh man that feels so awesome'. He stared at my hand pumping his cock for a few seconds and his breathing got faster. I didn't want him to come before me so I told him to do me too.
He leaned forward a bit, and moved closer to me, our hips almost touching. Before I knew it his hand was on my cock. He was right - it felt unbelievably good. Much better than my own hand, the best thing I had ever felt in my life. He jerked me off like an expert, and it didn't take us long to fall into a rhythm. I was on the verge of coming, so I stopped jerking him and leaned back like he had done earlier, with my hands braced against the log I was sitting on. I told him to do it faster and not to stop and he did, and then I was coming. The first shot squirted pretty high and plopped on the leaves in front of us; Scott stopped momentarily (I think he was surprised at what was happening) and I quickly told him to keep going. I sent out a few more smaller spurts onto the leaves, and then my come kept bubbling and drizzling down my cock onto his hand and wrist. When I was done he looked at his hand and told me that was disgusting, and I said no, not really. I told him to just wipe it on my underwear and he did and we both laughed. I told him I would do him now until he shot too and he just sat back again. Even though I didn't really feel like it then (because I had already come) I started to jerk him off and in no time his hips were bucking and he was panting almost like a dog. He said he felt like he had to pee and I knew he was close, that he would be coming any minute. When he groaned a minute later he shot a little bit; it was nothing like mine, just a little liquid, mostly clear. Some if it landed on his t-shirt and the rest just kind of leaked onto my hand. When he was coming he was literally pumping my fist with his dick like it was a pussy and groaning really loud. It was pretty funny. When he was done he told me it was awesome and he couldn't wait to do it again.
Over the next 2 summers he and I got together to jerk off about 6 more times in the same spot, and one time did it with 2 other guys at the same time. Our 'gang' split up in later years because a bunch of kids moved, but I will always cherish those naughty moments of my young teenage years.