This is a true story of the time that my brother, my friend, and I had our first sexual experience together. The only things I changed are our names. This is a very long story, but I didn't want to deprive you of details. After all, some of my favorite stories are the longest ones on here. I've been enjoying this site for nearly two years, so I thought it was time to give back to the community. Comments are appreciated, and I hope you enjoy.
Our first experience occurred on a very hot night in mid-June. My brother, Evan, was 13. I am Tom, and at the time I was 14. My friend, Ethan, who was also friends with Evan, was just a couple months younger than me. I'll start with the afternoon before that night, because that's when things got started. My family lived in a town where there weren't too many people. The houses were generally pretty large, and everyone had a lot of land. We weren't rich; that's just how the town was. My house had a big backyard. Behind a row of trees was another little area that had a pool and a fire pit. Each time I invited one of my friends over, we would set up a tent near the pool so we could cook hot dogs and swim, well away from the prying eyes of my parents. Its not like my parents were a problem, though. They always let us do our own thing whenever a friend was over.
Now, here's a little bit of background information so that you understand the story. I've always known that I'm bisexual though I seem to lean toward guys rather than girls. None of my friends knew this at the time, though my parents may have guessed. They knew I masturbated quite often, and both of them had caught me multiple times when I had been a little too careless. Whenever they saw what I was doing, they always said, "Come find me when you're done". They never really talked to me about it, but I didn't get the feeling that they would have been uncomfortable if I had told them that I was bisexual. They were very open-minded. My brother and I had a great relationship. We barely ever argued. There was barely a year between us, so we often saw each other as friends rather than brothers. We were in a small town without a whole lot of people, so we spent a lot of time playing around outside.
Being outside was a big fad back in those days. I was pretty sure my brother masturbated as much as me. He had actually walked in on me when I was 13, and while nothing happened between us, he could tell what I was doing. When we were outside playing in the woods near my house, we sometimes decided to go naked. This was especially common if we were going to swim later on. Nobody was around, so the chances of being seen were slim. And even if our parents saw us, they wouldn't have cared. As I said, they were open-minded about things like that (and still are). It was thrilling to be naked together, often running around playing some type of game while we had (at least) slight erections. However, nothing overly sexual occurred between Evan and I until the night Ethan stayed over. So now that I've bored you all to death with the back story, lets get on to the stuff I know you want to read about.
It was a very, very hot day in mid-June. I had just turned 14, and I invited my friend Ethan to have a sleepover. I secretly had a huge crush on Ethan. I'd never seen him naked before. He was about the same height as Evan and I, about 5. He had light, sand-colored hair that sometimes matched his normally sun-tanned body. My brother and I were pretty pale and brown-haired. We all were pretty slim and fairly athletic-looking from all the swimming we did. Ethan had bright blue eyes and his voice had just started becoming deeper, which sounded really seductive. However, I'd never gotten any indication from him that he was interested in guys.
Ethan came over during the afternoon. Evan was friends with him as well. Ethan and I were in 8th grade together, but Evan, who was in 7th grade, had gotten to know him outside of school. After Ethan arrived, we all played around outside. We set up the tent that we would be sleeping in near the pool, and then explored the woods some more (we all remained clothed, despite the extreme heat). When it was about 5pm, we decided to get in the pool to clean off before dinner. Ethan went inside to change into his swim trunks, and Evan and I changed outside by the pool. We stripped off in front of each other without blinking, because we were used to seeing each other naked. We stared at each others dicks for a moment (I specifically remember that his twitched I caught his eye and he smirked) and then pulled our swim trunks on. Ethan came back out, and we took turns jumping into the pool. We played around for a while, splashing water and whatnot, acting like kids. Evan lunged at Ethan to try and tackle him, and jumped onto his back. "Evan, get off"! Ethan yelled, pulling himself away while laughing. He pointed down. "Dude, look, you have a boner! I felt it"! I looked down, and sure enough I could see a good-size bulge in Evans swim trunks, oddly distorted in the water. Ethan lunged back at Evan and attempted to seize Evans trunks to pull them down. For a millisecond, I was super horny and then I heard my parents calling us in for dinner. Ethan and I laughed about Evans boner as we got out of the pool. He just covered himself up with a towel, smiled, and told us to shut up.
By this point in the story, you're probably wondering where things are going and if you should simply abandon this long recollection. If that's what you're thinking, I sincerely hope you keep reading on for a bit longer, because all of what you've read so far is leading up to what happened that night.
After dinner, my family watched an old movie together. When it was over, Ethan, Evan, and I went outside. We were told to have the fire out by 11 so that we wouldn't burn the trees down. It was around 9 when we went outside, and it was pretty dark by then. We had the lights on in the backyard and by the pool so that we could see. We got the fire started and roasted some hot dogs. Each of us enjoyed several. Then Evan entertained us with a not-so-spooky ghost story that he had read in a book. Unfortunately I can't remember what it was about, except that it was corny. We played a bit more in the woods. They're actually pretty creepy at night, because you hear things creeping around but you can't see them. Ethan played some prank on Evan that made him get pretty upset, so we decided to go back to the tent. By that time it was 11, so we used some water from the pool to put the fire out. We turned off the lights and headed into the tent. It was still very warm out, and the heat from the recent fire was still present.
You could barely see in the tent since the lights were out. I peeled my t-shirt and pants off so that I was left in only my boxers. I heard Ethan and Evan do the same, and we lay down on the mattresses we had brought out from the house. They were placed about a foot apart from one another, so we could still talk. I was on the mattress in the middle. Being feet away from two boys who were nearly naked made me extremely horny. Ethan and Evan talked for a while, and I chimed in a bit. I was mainly daydreaming, thinking about what Ethan looked like naked. I wasn't really listening to what they were saying, but I realized my dick was pointing straight up, completely hard at 5.5. I felt the fly of my boxers give way, and I knew that my boner was completely exposed with nothing but the nights darkness covering it up. I wondered if Ethan and Evan would notice if I started masturbating slowly and quietly.
And then, without warning, I heard the lamp next to Evans mattress click on. I hadn't heard him say he wanted to get something from the house. I don't even remember what it was he wanted, because I had been in my own world while they were talking. But when he clicked the light on, both he and Ethan got a birds eye view of my rock hard dick and I was completely unprepared. That, right then, became the most embarrassing part of my life up to that point. It was a split-second after the light flipping on when I reacted. I instinctively reached for a blanket to cover myself up with but there wasn't one. I was so hard that my boxers couldn't go around my dick. I don't know how much time passed, probably just a couple seconds, before I realized that both my brother and friend were staring unashamedly at my dick, looks of glee on both of their faces. And so, with no other option left to me, I flipped myself over so that my dick dug into the mattress, out of sight. I was laying on my stomach. And then the overpowering humiliation set in. "Oh my god, oh my god", screamed Ethan, scrambling up from the bed and standing over me, a look of delight on his face. "It looks like he's humping the bed", Evan shouted, laughing as much as Ethan was. I noticed that both of them were getting boners as well. Tents were starting to form in their boxers. As embarrassed as I was, I was also getting a little horny. I decided to take a huge risk. "Oh, you like it"? I asked, my voice trembling, my face feeling as hot as an iron. And then I turned myself back over so that my dick flopped around onto my stomach, still sticking through my fly.
Both of them stared at it. To this day, I'm not quite sure why. If I had been in their place and they were in mine, I would never have made it so obvious that I wanted nothing more than to stare at their dick. I guessed that they stared because it was so big. However, as I learned later, mine wasn't the biggest so, as I said, I'm still not sure why they were so interested in me. However, them staring at me wasn't a problem; in fact, it just made me hornier; especially since I could see that both of them were getting pretty hard as well. The path to getting what I wanted was suddenly illuminated, and I decided to take my chances.
"Looks like you enjoy seeing my dick", I responded, putting a smirk on my face. "Since you've seen mine, its only fair that you show me yours". I didn't make it seem as though I'd already seen Evans dick hundreds of times. However, I had never seen it completely hard and I admit, I was just as interested at seeing Evans hard dick as Ethans. I was hoping that Evan wouldn't have a problem with taking his dick out, because that would help convince Ethan. I waited on the tips of my toes (not literally) for a response. They both glanced at each other, and then their eyes wandered down to the tents in their boxers. They seemed surprised; apparently they hadn't realized they had erections. "Well, I guess so", Evan said tentatively. Ethan and I both watched him anxiously.
He grabbed the edges of his waistband and pulled. He had trouble getting it down because he was hard, but hey, maybe elastics made to get around more than just your waist, haha. He managed to get his boxers down, and out popped his 13 year old dick. As I knew, it was circumcised just like mine. He had a bit of brown hair around the base of his dick, and a couple of strands around his tight balls. None of this was new, but the size of his dick was. It was around 5. Not quite as long as mine, but just as thick, and nearly identical in color. Evan looked up at Ethan nervously, looking for his reaction, but Ethan was busy staring with what looked like hunger at both of our dicks. I raised my eyebrows at him. Still taking in the sight of our dicks, he too pulled down his red boxers. And out came the most beautiful penis I have had the privilege of seeing in my entire life. It was basically like all other penises, but knowing that it was attached to someone I had envisioned naked for a long time was what made it special. He was circumcised, and 6 inches long the longest out of all of us, even though I was older than him. The head of his dick was red and puffy. His balls hung low, and they were a good size. The light hair around his dick matched the hair on his head. It seemed as though he regularly washed it and took good care of it, although that could just be my memory making it seem even better than it really was.
And there we stood, three naked, horny teenagers, alone in a tent, fully erect, where nobody would ever see us for at least 7 hours. So what do you think we did? What happened next went far beyond what I had ever dreamed of doing with Ethan, or any boy for that matter. I have no idea how long Evan and Ethan stood over me with their erections a foot from my face. We all were staring at each other, trying to get an idea of what each person wanted to do.
Surprisingly, Ethan was the first to speak, saying that our dicks were nearly identical. "Yeah, look", I said, and I got up and stood face to face with Evan so that our dicks were in front of each other. Ethan got between us and looked them over. "Evan, you're a little shorter, but they're really about the same". Ethan was just looking at them, but I could tell he wanted more. "You can touch them", I said, trying to get the tremble out of my voice. Evan looked at me, his eyes alive with genuine excitement. This was the first sexual experience either of us had had.
Down on his knees, Ethan took one dick in each hand. He seemed a little nervous at first, but worked up his courage pretty quickly. He examined both of our heads and shafts very closely, pulled on my pubic hair, and cupped Evans balls. Ethan's boner hung below, just as hard as ours. Evans dick twitched when Ethan poked the head. His seemed prone to twitching. Mine didn't seem to twitch much at all. Evan loved having his dick looked at, and I did too. I had been dreaming about something like this for so long, but I'd never imagined my brother being part of it. Having him there with me made it ten times more exciting. This was new for both of us, and since we were so close, it seemed natural to share this first experience in each others company.
Ethan suddenly stood up, and his boner swayed back and forth. I looked at him, and all he did was nod. That was all I needed. I got down and examined Ethan's dick, with Evan right there too. Together we noticed that his foreskin was a little looser than ours was. His head was really squishy and plump, and a light coating of hair went around his balls and dick. I squeezed his balls, causing Ethan to jump. Evan played a bit more with his dick. He was really interested in how loose Ethan's foreskin was, even though he was circumcised. He kept pulling the foreskin back and forth. He was basically masturbating him. I was so horny that I nearly melted when Ethan spoke.
"Do you guys want to go outside"? He asked. We both looked up at him, and I could tell that Evan was disappointed. Clearly he wanted more to happen. I was disappointed as well as confused, until Ethan said, "Have you ever tried skinny dipping"? "Sure"! Evan said enthusiastically, jumping up. I was happy as long as we all remained naked and didn't get caught, so I agreed. Evan opened up the tent flap, and we went outside, leaving our boxers and the light in the tent. We could barely see anything. I decided to go ahead and turn the pool lights on since there was next to no chance of our parents looking out of the windows at this time of night. And if they had, the trees would have blocked us from view. Yay for trees! We could see pretty well with the pool lights on.
We climbed up the ladder one by one. Evan went first, and having his ass inches from my face was the biggest turn on so far that night. Evan jumped in first, and I went in second. Ethan joined us third. I had been worried that the water might be too cold, but fortunately the extremely warm night had kept the water temperature the same. I was wondering if Ethan just wanted to swim around for a bit. Luckily, he wasted no time in swimming right over to us. I could just tell that it was going to be a great night. Ethan grabbed our dicks underwater. I was in heaven, and clearly Evan was too. Ethan slowly started jerking us off. We were inches apart from each other anyway, so it just felt natural to lean forward so that all of us were touching. I can't even describe the emotions running through me as Ethan slowly jerked us off. Evan was breathing hard, and I could feel his hot breath on my neck. I turned my head to him, and saw that his eyes were closed. I was so horny that I decided to surprise him.
I leaned my head forward, and kissed Evan on the lips. His eyes opened immediately but he didn't pull his head back. Instead he leaned forward, and we starting making out in front of Ethan. I could see out of the corner of my eye that Ethan had a huge grin on his face. He was obviously enjoying seeing two brothers kissing like there was no tomorrow. I felt Evans tongue poke my lips. I slowed down for just a second and looked at him. He was so into it that I wasn't quite sure if he had done it on accident. However, as he kissed me harder and forced his tongue into my mouth, I could tell it was intentional. We french kissed in front of Ethan, whose jacking was becoming faster and harder. I was in oblivion; I was happier than I had ever been before. And then I could feel my dick starting to twitch, which only happened when I was about to cum. I could also tell that Evans breath was getting faster. I couldn't let it end so quickly. So as much as hated to, I broke off the kiss and told Ethan it was his turn. He stopped jacking us off and looked happier than ever.
We swam over to the pool ladder. Ethan sat down on the top rung so that his dick was right in front of us. Evan and I were right next to each other, and as soon as Ethan said he was ready, we went for it. Evan fondled Ethan's balls and played with his pubic hair while I grabbed his dick and started jacking him off. Ethan closed his eyes and rolled his head back. I could tell he was really enjoying it. With my other hand, I reached down and started rubbing Evans ass. He responded by rubbing mine in return, taking his hands off of Ethan. I felt him run his fingers along my crack. I'd fingered myself before, but never had I imagined someone else doing it for me (especially not my brother). I pushed back against his fingers when they stopped right at my hole, and that was all the permission he needed. He got behind me, and I felt his index finger slowly slide into me. He stuck it in as far as it would go. How did he know so much about this? I wondered. (I later found out that he'd gotten a small stash of porn magazines from a school friend). He started going faster, and then pushed a second finger in me. That was all I could take, so I told him no more so that he wouldn't try for three. I noticed that my ass seemed much tighter in water than it normally was. It was then that I realized I'd forgotten about Ethan.
I looked back around and saw that his eyes were still closed. His dick was bulging, and there was a small drop of pre-cum right on the tip. I'm sure you know, you sometimes act without thinking when you're horny. Well, I was past horny. I was horny as hell. So, without thinking much about what Ethan's reaction would be, I brought my head forward and licked the pre-cum off. It tasted a little salty, but that may have been the chlorine from the pool. I looked up and saw that Ethan's eyes were wide open, but he was grinning. "Suck it", he said in a strangled voice. I looked down at his dick, and it looked more inviting than ever. So, without hesitation, I wrapped my mouth around his dick and started to suck. I could get about 4, maybe 5 inches in without feeling like I was going to choke. However, that didn't seem to matter to Ethan. He let out a huge moan and lay back so that his back was resting on the top of the ladder. It was awesome sucking his dick while my brother was fingering me. I went faster and faster and Ethan started breathing harder.
Evan had finally realized what was going on. He stopped fingering me and said, "Dude, let me try"! He pulled me away (much to my disappointment) and jerked Ethan's dick for a minute before taking it in his mouth. Seeing my brother sucking a dick nearly made me cum right there. I decided to do what Evan had done for me, got behind him, and grabbed his ass cheeks. They were smooth and beautiful, especially with the light reflecting off of the water still on them. I played with his cheeks for a little while before taking my finger and pushing it up inside him. His ass was extremely tight, and I was afraid of hurting him, so I only went in a couple inches. I never used more than one finger. He was happy as could be though, and I could feel his whole body moving up and down as he sucked Ethan's dick. Ethan moaned some more, and it was a second before I realized that he was cumming.
"Don't stop", he grunted. My brother went as fast as he could, his wet hair flying all over the place. "Fuck, fuck, fuck"! He thrust his dick into Evans mouth, and though I couldn't see the cum, I assumed that it was pouring out of his dick. Sure enough, after Ethan panted heavily, Evan opened up his mouth, put his finger inside, and pulled out a little string of cum. "That was awesome", Evan said, and he sucked it off of his finger. Ethan looked exhausted. He lay spread out like a star on the top ladder rung for what seemed like several minutes. "Was that fun"? I asked Evan. "Absolutely", he said, grinning and blushing just a little. "Want me to do you"? he asked. I jumped with glee. "Sure", I said. Ethan recovered himself and got up. "How about we finish up in the tent"? Ethan asked. "Okay, will you suck us"? I asked him back. "Definitely".
We dried off using our boxers that were still in the tent. Still nude, we all plopped down on my mattress. I couldn't wait. Obviously Evan couldn't either, because the second I turned to him, he grabbed my dick and sucked away. It was so much better than masturbating. Ethan lay down next to Evan, and tentatively pulled at Evans dick for a moment. He looked a little nervous, but he probably felt that he needed to return the favor, so he slowly stuck the head of Evans dick into his mouth, then the shaft. Evan moaned as he continued sucking my dick, and at the same time, he reached under me and started to finger my ass again. All of the feelings built up inside of me, and I knew I was about to cum. "Keep going", I said, and Evan sped up. Ethan sped up on Evans dick as well. I felt my balls tighten. "Suck it, please fuck"! I shouted, as I shot several ropes of cum into my brothers mouth. I felt euphoric there was nothing else like it. Evan kept sucking me, clearly wanting to get every drop of cum out of my dick. I felt like I was going to have a heart attack though. You know how sensitive your dick is right after you cum. I had to pull away, because Evan showed no sign of stopping. He let out a moan too, along with a whole string of swear words, as Ethan worked his head up and down Evans dick. I kissed him as he came, and I could taste a salty something on his tongue. Evan's breathing slowed down, and I could tell he had cum. Ethan pulled his head up, gasping for air. Who knew how long he'd held his breath as Evan came. "That was awesome"! Evan shouted.
Ethan grinned at me, and I could tell that the night wasn't over yet. All of us remained naked, talking about what we'd just done. Our dicks were hard again in no time. "I think its time for Tom to taste some cum", Ethan said. "Yeah, nobody's cum in your mouth yet"! Evan said, laughing at me. "Okay I'll do you both", I said.
Note: I considered ending the story here, but decided since I'd already gone this far I might as well finish it up. I pushed them back against the mattress, right next to each other. Their dicks were both pointing straight up, and they looked very excited. They looked at each other, and Evan leaned his head forward and started making out with Ethan. I didn't wait to see more I just went down on their dicks. I started with Ethans, and switched back and forth between them every couple minutes. I could fit about all of Evans dick in my mouth, but I wasn't comfortable stuffing my throat with Ethans yet. They lasted quite a while, probably 15 minutes (a long time for two boys getting their dicks sucked. Keep in mind they had just cum minutes previously). Ethan came first, and while not a whole lot of cum shot into my mouth, it tasted a little saltier than the pre-cum I had tasted in the pool. I sucked it all up, and Ethan moaned. I then finished up my brother, who starting swearing again as he came. A good glob shot to the back of my throat, and I swallowed it eagerly. I looked up at them, and they had huge grins plastered over both their faces.
By that time, it was around 2:30am. However, none of us were tired in the slightest Ill end my story there. For the rest of the night, we continued jacking each other off (no more oral after that point, though). However, that was just the first of many, many experiences between Ethan, Evan, and I. Plus, after this sleepover, the relationship between Evan and I reached a whole new level. I think our parents knew what we did together, but we didn't mind. We didn't go a day without cumming together. Evan was always horny, and he never missed a chance to give me a blowjob.
By the way, shortly after this story took place, all three of us came out to each other as bisexual. As if we didn't know! Many of the experiences between Evan and I took place in the woods after the sleepover. We'd always been used to being naked in there, so now that we knew we were open to having sex, it felt natural to do it there. I cant even begin to guess how many orgasms Evan and I had in those woods.
Depending on the feedback I get on this story, I may write stories about our other masturbation sessions. They continued for many years, and still happen occasionally today. My family still owns that land, so whenever we are there, Evan and I normally cum at least once together to bring back old memories (and to create new ones). We are both in our 30s now. If you made it through this entire story, I applaud you! I sincerely hope you enjoyed it as much as I did. Please let me know what you thought of the story, and if you'd like me to write more. Happy jacking!