My first time with a friend, just last night!
First, before I start, I want to say that ever since I started jacking off I have always wanted to do it with a friend. Particularly one of my best friends Andy. I do not love Andy in a romantic sense, but I can not deny that he is attractive. Last night I finally got to live out my fantasy with Andy. And we both agree it will be the first time of many to come.
It all started a month ago. I invited Andy to come over to my house for the night, not only because it was something to do. But because I also had some brand new porn that we both wanted badly to watch. We stayed up late reading stories on this site and others until my parents went to bed. Then we snuck to the living room and put in the new DVD. Even before the DVD started we were horny as hell from reading the hot stories on this site, but after an hour of watching porn on the TV me and Andy were ready to burst. We went back up to my room and got down to our boxers. I was surprised to see how large the bulge in Andy's boxers was. We were just about to jack it together when he said he didn't feel comfortable with doing it and went to the bathroom to get off by himself. After we had both taken several turns in the bathroom, I asked him if he would ever jack off with me; to which he replied, 'Yes, next time.'
Over the next month I called him every weekend and asked him if he could spend the night, but wither he was busy camping or going out with his family, or I was similarly engaged. Finally after a month of waiting, we finally had a weekend where both our families weren't doing anything. Much like the time before, we stayed up late and watched porn. Andy knew that at some point tonight we were going to do it, and he kept nervously shifting his dick in his pants. After about two hours of watching porn and talking about girls we liked and sex, he said he wanted to jack off with me now. Needless to say, I was excited.
Before we started, he made me promise I wouldn't tell anyone about this unless he said so, and he also made me promise that we would get naked under the covers of my bed first before we started. We got under the covers, and at the same time took off our pyjama bottoms, and then our boxers. At that moment we paused at the wonderful feeling of our dicks being freed from our underwear, and enjoyed the heat we could feel radiating from each others rods. I asked him if he was ready and he nodded nervously. We pulled back the covers and exposed ourselves. We complemented each other on the size and girth of our cocks, and compared from every angle. His was about 5 3/4 inches long, but 5 around, mine was 6 1/4 long and 4 3/4 around. He then asked me nervously if he could touch mine, I said yes, but only if I could touch his. We gently, and then more firmly grasped each others cocks. This was the first time I had ever touched a dick except my own and I was surprised at how hard it felt. I then asked if I could jack him off, but he said not tonight. After we were done feeling each other we set to work on our own rods. As we proceeded we told each other different methods we used and tried them out. As we continued we grew hot and sticky, the earthy scent of our jacking filling our nostrils. Between moans and gasped we described to each other what we were feeling. After about 20 minutes of wonderful jacking, we decided to go in for the orgasm. Our speed and grip changed as we went down the homestretch of pleasure. With a shudder and a moan I reached my climax and shot my load all over my chest, I was surprised by how little there was, maybe I had just been nervous. About thirty seconds later all the muscles in Andy's body flexed at once, he groaned and shot his cum, there was more from him than from me, and he hit himself right below the face. We lay on my bed in the haze of satisfaction that comes after a good jack. After a while we cleaned up and went to sleep, but this was not to be the last incident of the night.
Four hours later I awoke to Andy returning from the bathroom, I asked him what he had been doing, and he said he had been peeing. I told him I bet you were jacking off, and he said he hadn't been, but he was about to. I looked at him for a minute, not quite getting what he had said. Then it became clear, there was no nervousness this time, we whipped of our clothes and proceeded to enter another wonderful session of jacking. This time we were a little more adventurous. We layed close together on my bed, our throbbing cocks almost touching. Occasionally we would accidentally hit each other, and a short moan would usually come right after. Once again I asked Andy if he wanted to jack each other off, but he said no again. We resumed jacking, talking dirty and low, and soon started to feel the build up to orgasm. Andy then told me he wanted to do it one at a time, so the other could watch, and said he would go first. I slowed down my stroking and watched him slowly and tenderly approach orgasm, once again I witnessed the muscles in his body tense, and he let out a gasp, and a small dribble of semen. He wiped it off and then got into position to watch me shoot. I couldn't believe how amazing what was happening was, and as I approached orgasm, I thanked Andy for doing this with me. Not soon after he settled down to watch, I was right on the edge, after a few more strokes I was over, and the pleasure ripped through my body. I shot two thick ropes onto my face, and many more onto my chest. I gasped and shuddered as I was consumed by the feeling. After what seemed like an eternity of intense pleasure, I relaxed. Andy was amazed at how much I had just shot, he said it was something out of a porn. I was completely drained from my orgasm, and I asked him to wipe off the semen, which he did. We talked for the next ten minutes about how great it was that we had this to share with each other, and agreed to do it as much as possible. I'll be sure to write down all those stories on this site.
Well, that's it, hope it turned you on as much as it did for me to write it down. If you can, jack off with a friend, its something you HAVE to try at least one, chances are your friends want to do it too, their just too scared to ask.