This is the story of my first time ever with a guy.
When I look back on it, I think that this whole time started at the night of my friends Bar Mitzvah. It this point, I was 12 and was about 5.5 feet tall. I was well built, had pretty strong legs and worked out regularly, so I had pretty big muscles. My friend, Josh, was 13, and a bit shorter than me. He was about 5 feet tall and had a sprinter's body. His parents had let him have a few friends over for a sleepover that night. At first it started out as a typical young kid's sleepover. We played video games, we drank soda, we played more video game, etc. I had been looking at every type of porn for about a year at this point, liking both pretty much the same, with a liking to gay porn better. So anyway, around midnight, Josh's parents went to bed. At this point, we were on a sugar high and were getting really horny. It started out with the three of us, myself, Josh, and our other friend, Chris, all striping down into our shirts and underwear. I remember that I was wearing blue boxer briefs, Chris was wearing blue-green boxers, and Josh was wearing red boxer briefs. At first we were just goofing around, daring each other to touch each others dicks through our underwear (mine was the main attraction as I was about 3.5 inches long hard at 12). Then, we started getting a little hornier, and started mooning each other, pulling down Chris's boxers to expose his butt, etc. And then suddenly, Josh dared me to hump his bare butt with my member. I jokingly said (but was really hoping) should I do my bare dick on his butt. He said no, just do it through your boxers. Well that wasn't going to stop me. Chris didn't want to see this, so he turned off the lights in the basement and Josh went onto the couch and put his butt in the air. Little did either of them know that as soon as the lights went out, I pulled my stiff member out and was getting ready to use it. I had seen anal sex before, but didn't know that you needed lubrication. So what happened was I rubbed my stiff member against his butt crack and started trying to force it in. At first he didn't say anything, but then suddenly he said to stop, that that was enough of that. So I quickly pulled my briefs up just as the lights were coming up. We didn't talk about it for the rest of the night, but I had to go the the "bathroom" about 10 minutes later. That was probably the very first time I had every done anything with a guy.
Fast forward 3 weeks later. I get a call from Josh again, asking if I wanted to have another sleepover at his house. I said sure and asked what time. I was planning on jacking off (by this time I was 13) but I half-expected something to happen, so I held off. When I got to Josh's, it was pretty much like any typical sleepover before. We had pizza, watched some crappy movie, and played video games until 12:30. While we were sitting there playing Super Smash Bros., Josh lost and then said that he was bored. So I said, well, what do you want to do? And he replied that he wanted to do something like what we had done 3 weeks ago. I thought about what we could do and thought about masturbating each other. So I suggested it to him, and he said that he didn't know what masturbation was (he is a REALLY sheltered kid). I said to him that I would show him, but he had to take off his shorts first. He said OK, but first he had to dim the lights. So I let him do that and he pulled down his shorts to reveal Hawaiian-themed boxers. I told him to sit next to me on the couch and to spread his legs apart. As he was sitting down, I noticed a slight poke in his boxers, signaling that it was a good time to start. So I said to him that masturbating was a way of making yourself feel good by rubbing your dick. He nodded and asked me to show him. I said alright and grabbed his dick through his boxers. I started rubbing the head with a few fingers and immediately began moaning. I rubbed his penis for about a minute (it felt about 2 inches long) and then stopped and said that THAT was masturbating. I told him that if he wanted me to do anything else, that he would have to do the same. So he reluctantly agreed and grabbed my hard dick and wrapped his hand around it. His first words were, Holy shit, your dick is HUGE! I laughed and said that I was lucky. So he slowly started jacking me off and I soon went back to doing it to him. We sat there for a good 10 minutes, slowly jacking each other off, until suddenly Josh said to stop, that he was going to pee. I said that that was the best part, but he wouldn't have it. He stopped jacking me off and pulled away. He went back over and turned on the lights. It was at this point that I noticed that he had a slight wet spot on his boxers. I said to him, come on, lets see it. He said see what. I replied, your dick. And he slowly pulled his boxers back to show me his dick. I had been right, it was only about 2 inches long and had a few scraggly hairs, but other than that, not much else. He suddenly pulled it up and explained that he had to go to the bathroom. I knew what he was doing in there, so I finshed off myself.
We didn't talk about it the next day, but a week later, I got another request for a sleepover. This time, I said that it should be at my house. So he came over, same formula, pizza, movie, video games, blah blah blah. At about 1, I said to Josh, do you want to do that thing again. And he said yeah, but this time, we should do it without boxers. As soon as he said that, my dick went rock hard. I managed to say OK without screaming, so we both pulled down our pants and boxers to reveal our rock hard dicks. He looked at mine and said, wow it really is huge. I replied that his was pretty big too, even though it wasn't. So we slowly started to jack each other off. We were both groaning and moaning and it was insane. It felt a hundred times better than doing it yourself. Suddenly I noticed that Josh's breathing had quickened and that he was thrusting his hips slightly. I looked over at him to see if he wanted to stop, but his eyes were shut. Suddenly his hips thrust forwards and out came the most cum I had ever seen in my life apart from my first time. It got all over him, his dick, my hand, everywhere. He slowly stopped and said that he had had enough. But I said, c'mon, you've still got to do me. So he said OK and jacked me off until I came. He was amazed at mine because it was way more than he had done. So there we were sitting there covered in cum, both having just given our first full handjob to another guy. We didn't say a word and instead just grabbed some tissues and cleaned ourselves up. We both went to bed and woke up the next morning and left.
A week later, he called just to see if I wanted to hang out for the afternoon. I went over there and found out that his parents were going to the airport to pick up his brothers from college. So he and I went downstairs and stripped down completely. Then Josh said that he had heard of something before called oral sex. I knew exactly what this was, but decided to play dumb. He told me that it was when someone either got their dick sucked on or sucked another dick. He asked me if I wanted to try it with him. I said sure, why not. So I agreed to suck Josh's dick first. He sat down on the couch and I slowly moved my mouth towards his now 3 inch dick and then, all at once, engulfed it in my mouth. The taste of his cock was incredible. It was like a mixture of a non greasy sausage and a very slight salty taste. He started moaning and groaning. I kept on sucking. Suddenly after about 2 minutes, he said, oh God, I'm gonna cum! And he started thrusting his hips forward, and suddenly let out this high-pitched yelp and I felt the cum gush out of his cock. This was my first time ever tasting cum, and I have to say, it tasted great. It tasted a bit like unsweetened eggnog. So anyways, I let Josh cool down and told him that a promise was a promise. So I sat down and he kneeled down and started sucking on my cock. At first, he wasn't all that good, mainly because he couldn't get it down (it had grown and was almost 4.5 inches long by then) but he slowly found a way to get it in. That was probably the best feeling that I have ever had. It really is indescribable how it felt to have my dick sucked. But eventually after about 2 minutes, I came right inside of Josh's mouth, and he swallowed it all. We got really lucky, because right as we had both gotten our clothes on, his parents came back, and I had to go home.
Unfortunately, by this point, it was mid-November, just about to be winter time, and we lived on opposite ends of town, so it made it hard to do any sleepovers. But one night, about a week after Christmas, Josh said that he could have a sleepover at his house. I jumped at the idea of another night with Josh. So when I got over to his house, it was same routine. Around 10, Josh said that once his parents went to bed, he had something special. So around 12, his parents went to bed and he said that he would be right back. He went over to his brothers room and came out a minute later holding a bag from CVS and a DVD. I asked him what shitty DVD we were going to watch, and he said to just wait. He put the DVD in and hit play. He told me to turn around so he could get to a certain point. After about a minute, Josh told me to turn around. I did and was immediately hit with a video of two guys making out on a table. I looked over at Josh and he said that his brother had this in his room and that he had watched it and wanted to try some things. I already had a pretty good idea what "things" were, so I asked what. He said that he wanted to fuck me. I hid my enthusiasm pretty well and asked him if he knew how. He said that his brother had told him what to do and had even shown him how. So I said alright what do we do first, to which he replied, this. He reached over and grabbed my crotch and started rubbing it. Instinctivly, I reached for his. We sat down and just sat there rubbing each other's crotches. Then suddenly he stopped and stood up. He took off his shirt and his shorts to reveal a very tight pair of light blue briefs. I grabbed my shorts and yanked them down and took off my shirt and revealed to him my red boxers. He slowly sat down on my lap and leaned in closer to my face. I knew what was coming, so I opened my mouth and sure enough, his tongue slipped right into my mouth. I don't know how long we sat there just kissing, but eventually, I stopped and slowly pulled down his briefs. I revealed his penis, standing at attention, waiting to do anything. I slowly got down on my knees, but Josh said, no, no blowjobs. So, I knew exactly what that meant. I managed to stammer, do you want to fuck me? He nodded and grabbed the CVS bag and pulled out a thing of vaseline. He asked me do you know what to do, and I replied, of course. So he pulled down his briefs and got on the couch doggy style. I took a glob of vaseline and put it right up to his asshole. I slowly put it all around and then, with a huge glob on my finger, went into his ass with my finger. He started to push back, which was good and he was moaning a bit. After I was satisfied that he was lubricated, I grabbed my dick and started pushing it into him. At first, it didn't want to go in at all but suddenly it slid right in. He jumped at this a little bit, so I slowly pushed in and told him to push back just like earlier. Eventually, I got my entire dick into his ass. I slowly started to pull out and then push back in when I was about halfway out. I started off really slowly at first, but as I started to go towards cumming, I started to get faster and faster. The feeling was amazing. It was like my dick was surrounded by warm waterbeds, but a thousand times better. Suddenly, I was about to cum and I started to pull out, but Josh said to keep it in, he wanted to feel my cum in him. So I stayed in and came right inside of him. It was a huge amount, so when I pulled out, it started trickling down his ass and onto the couch. So I grabbed a cup and put it under his ass until it was all out. Then it was my turn. I had just had the biggest orgasm of my life and I was already rock hard again at the prospect of being fucked. I suddenly felt a glob of vaseline rubbing itself against my asshole. And then it slowly went in as Josh's finger went in. Then, he pulled his finger out. Suddenly, I felt his stiff member poking into me and slowly going in. I had never felt anything this good before in my life. There was only a slight amount of pain while he was going in but once he got all the way in, I relaxed and just let him fuck me. He started slow, like I did. The feeling was incredible, having his body slam into mine and feeling his bush right at the top of my ass. Suddenly after about 2 minutes, he started to go really fast and then all of a sudden I felt the most peculier feeling in my ass. It was like I had water up there and I realized that he had just came inside of me. It was an amazing feeling. We used the same cup to collect his cum from my ass. After my ass had been drained, we both went to take a shower together (there was a shower downstairs). We both started to soap each other up in order to wash the vaseline off of our dicks and out of our asses. We eventually did that and we were clean as whistles. We stepped out of the shower and dried off and then went back out. We finished up the night by 69ing each other until we came. Then we put back on our clothes and climbed into bed and went to sleep.
Please only positive comments, if you find this offensive, then why are you reading this. If I get good comments, I will tell you about the next sleepover, where we introduced his brother.