Playing With Dicks – How boyhood experiments turn into teenage degeneracy – Chapter 02

Chapter 2 – Sleepovers – Jerking off with friends turns out to be so much fun, will it lead to anything else?

WARNING: For patient readers only! Please find Chapter 1 and start back at the beginning, you will be lost if you try to start here. Thanks for reading! xoxoxo

Playing With Dicks

How boyhood experiments turn into teenage degeneracy

Chapter 2 – Sleepover

It was getting pretty close to summer break one year, I was about to turn 12 years old in July, Matt had just turned 11 in May, and Jay was still 10 until his birthday in November. Apart from school which we all hated, those were good times those days. We had plenty of time and nice long days to play outside, we frequented the pool in our apartment complex, and school would be out for summer soon enough. As always we had our routine sleepovers almost every weekend, and on the rare occasion we’d even sleep over 2 nights in a row on Fridays and Saturdays. And soon enough we’d be having sleepovers pretty much every night all summer.

One night Matt and Jay were sleeping over at my place, and something had obviously put us in the mood for some mischief because as soon as we heard my parents go to bed we decided to play a little game of “truth or dare” in my dark bedroom. Even mentioning the name of the game brought up all kinds of implications, it was a well known fact that a good game of truth or dare usually ends up in some naughty taboo territory, that seemed to be the whole point. It was just an excuse to bring up some spicy topic not fit for normal polite conversation, a fun way to get awkward with your friends and try to embarrass each other, the truths often being more spicy than the dares. We didn’t know where we’d end up going with it, but we assumed we’d do a lot more truths than dares because we couldn’t do anything too loud and crazy late at night, we had to keep things quiet and pretend we’re asleep so we didn’t get in trouble for staying up. But we knew that sharing secrets was fun, and the more wild the secret, the more fun it might be. I had no idea what was about to happen, but I figured Matt and Jay both had similar ulterior motives as mine. We already knew pretty much everything else about each other at that point, so if we wanted to tread new ground and share new secrets then there was only one possible way this could go.

I don’t even remember who’s idea it was or how our game of truth or dare started, but it quickly became obvious that all three of us had been secretly thinking the same thing all along and we all had the exact same inspiration to play this naughty game. We had already talked a little bit about some of the interesting stuff we’d learned in sex education and theorized about stuff we still didn’t know, mostly relating to girls, but we’d never openly discussed masturbation and definitely never admitted to doing it. That night we were primed for it though, and by the rules of truth or dare we weren’t allowed to lie to each other.

It was a weird mix of nervousness and excitement as the question of masturbation came up immediately, like literally the first truth question. I don’t even remember who asked who or how the conversation started, but that doesn’t matter. But with the initial awkwardness of the question “do you masturbate?” out of the way, we were comfortable enough around each other that all 3 of us excitedly confessed to each other that we love to masturbate frequently, pretending you didn’t would be retarded. It all came out into the open so quickly and easily, like it shouldn’t have even been a such big deal to avoid the topic all this time. As nervous as it made us, it was actually quite a thrill to admit it for the first time ever to anyone and finally have an open and honest conversation about it, not counting the awkward lessons at school. It was so awkward to confess that we like stroking our dicks, but once that was firmly out in the open and we realized we’re all on the same page, it was a huge relief and then floodgates opened.

Under the guise of playing our stupid little game of truth or dare, we asked each other everything about how and when and where we each jack off, when and how we first discovered it and started out, what our favourite techniques are, how often we do it, and who are the hottest girls we like to think about when we go over the edge to orgasm. Suddenly it was such a rush to be openly admitting our dirty habits among ourselves, none of us had ever told anyone this kind of secret stuff before and it turned out to be a lot of fun just to even talk about it. I was right, turned out our little game of truth or dare was actually just an excuse to talk about sex and jacking off, and it definitely sparked quite a discussion.

Because we were such close friends we didn’t have any shame admitting anything, sharing all these secrets turned out to be quite exciting. Of course jacking off was nothing to be ashamed of, it’s actually the best kind of fun because it’s mischievous and taboo, and obviously all the cool kids are doing it even if nobody talks about it openly. We felt super mature for being able to discuss such a taboo topic without judging each other, and bringing it all out into the open just proved the level of trust we had among ourselves. And we were definitely all on the same page about it all – we weren’t even grudgingly admitting to our naughty habits under some guise of shame or embarrassment, instead we were downright boasting about it with pride, like a bragging contest – who jerked off the most often or in the riskiest places.

As we were bragging about when and where we each liked to jerk off, I told them I’d been sneakily masturbating right next to them at all our sleepovers, thinking it was no big deal and they’d probably admit to doing the same thing. But they couldn’t believe it – first Jay said he’d suspected me a few times but never said anything because he didn’t want to be awkward, and then Matt confessed he’d been doing the same thing, also secretly stroking his dick beside us all this time. Only he did a better job of hiding it because he’d seen what I was doing and already knew I was pleasuring myself. Jay was the only one who hadn’t already masturbated in the same room, or the only one who wouldn’t admit it.

I mean we weren’t really surprised or anything, but it was exciting to admit it to each other and not have to hide it anymore. Jay said he thought about jerking off at our sleepovers too, but didn’t have the guts to do what me and Matt had been doing, and that’s when things started getting interesting.

Still young enough to try and pull stupid childish power plays, I told them it’s my room my rules, and if they want to jerk off in my room then that’s okay, but masturbating is only allowed if we all let each other watch, pj’s down, dick out, light on, no hiding allowed. I wasn’t exempting myself from the rules, I was simultaneously kind of daring all 3 of us to do it, just dying to pull my dick out and show it off. They tried to play it off like I was being stupid and silly, but they couldn’t hide being just as excited about the idea as I was. At that point we’d barely even seen each other properly naked before, other than maybe some quick sneaky glances in the change room at the pool out of sheer curiosity. We’d grown out of the childhood innocence where nudity was freewheeling and omnipresent and not a big deal, and now we were at that shy preteen age when even changing around other guys got awkward. We’d barely even done the whole “show me yours and I’ll show you mine” thing close friends like us often do, and even though we were so close we’d never gotten over that childish nervousness about being naked around each other. Until that moment.

We were definitely curious to look at each other’s dicks and compare, and now we were skipping right ahead of just showing off. This wasn’t just a simple case of flashing each other our private parts, I was suggesting we skip right ahead to watching each other jerk off, and they were actually going for it. And I was shocked by how excited and shameless they were about it, like why the hell didn’t we do this sooner? I had been hoping for this reaction but didn’t expect them to be so open and forward about it. It was my fantasy that something like this might happen, but I was expecting I’d be the weird one with the dirty ideas and bold suggestions, to be stuck trying to convince my shy and hesitant younger friends to do something gay. I definitely wasn’t ready for both of them to be just as curious and perverted as I was, it was a better outcome than I could have hoped for.

Initially I thought I just wanted to get the awkward truth out of the way so we could comfortably masturbate around each other, but the two of them got so excited about the idea I suddenly had no clue where this might lead. Oh how quickly our game of truth or dare had turned into daring ourselves to jack off in front of each other. Not only did I want to see their dicks get hard and watch them jerk off, I couldn’t wait to show them mine and see their reactions. It was pretty clear that this game of truth or dare was going entirely sexual, and I think we were all simultaneously excited and a little worried where that might take us. What if this didn’t stop and we kept daring each other to go further? This was exactly the secretive mischief we loved getting into, but this one was more taboo than any of the other stuff we could have possibly gotten into trouble for. Like what if it turns out to be as fun as I think it will and we all accidentally end up faggots? I didn’t want to be gay, I didn’t think I was gay, but it was undeniable that I was getting hard just thinking about pulling my pajamas off.

It was dark in my bedroom as we sat around pondering what we were about to do, too dark to really see anything. It was my crazy idea and my rule I just made up, so I had to go first. So as we all agreed to pull our dicks one after another, I flicked on my little bedside lamp so we could actually see each other because that was the point after all, we actually wanted to see and were dying to compare our hard dicks.

I went first and slid my waistband down over my hips, and my dick sprung up hard as a rock. One by one Matt and Jay each slid their pajama bottoms down to reveal their hard little adolescent dicks, and we started taking a good close look at each other. All 3 of us were uncut so there was no weird circumcision discussion to have, and we all seemed to have pretty decent sized dicks for our age, maybe because we were all hard, maybe because our only comparison were the few soft dicks our age we’d seen. We obviously did a size comparison and mine was definitely the biggest, but only because I was the oldest, about to turn 12 and hitting puberty, almost year older than Matt, and a year and a half older than Jay. Matt’s was smaller than mine and Jay’s looked a tiny bit smaller than his, so it wasn’t like some dick measuring contest, we chocked it up to age difference. None of us had any pubic hair yet, and to me our smooth bald cocks looked so much better than any bushy hairy thing we’d seen on older dudes.

We rolled our foreskins down and checked out the heads of our dicks too, and then we actually started stroking our shafts and watching each other play with ourselves. We compared and discussed stroking techniques and other ways to do it, like humping your hand, and it was deviously exciting to be talking about this dirty stuff and jerking off openly. All three of us were so enthusiastic about it that I already began to wonder if this experiment might even lead to something more than just masturbating in front of each other. It was so exhilarating to be breaking taboos together and having some forbidden fun that there was no telling where it might lead. I was already seriously thinking about suggesting something crazy like giving each other hand jobs instead of just jacking off, but I was still too worried about acting like a faggot and didn’t want to suggest anything gay like actually touching each other’s dicks. I was super curious and would have been willing to try even more gay stuff than just hand jobs, but I didn’t dare admit any of that before I knew how Matt and Jay would feel about it. Rather than risk pushing things too far too fast and scaring them off with my weird gay thoughts, I decided to go with the flow and just see what they wanted to do. After all they did end up being way more enthusiastic about the whole thing than I ever expected, so why not see where they want to take it? Maybe one of them would suggest jerking each other off or even sucking dick before I worked up the guts to say it.

I kind of assumed and really hoped that Matt and Jay felt just like I did and had similar weird gay temptations, but if they did they were obviously even more nervous about it than I was, because they sure weren’t bringing it up either. As we sat around and watched each other jack off we were all probably thinking exactly the same thing, but we were all too scared of acting gay to even mention it. Just masturbating together was plenty gay enough, and we made sure to talk about girls we had crushes on and fantasized about, almost as over compensation for how gay jacking off together was. We talked about pussy and theorized how and when we’d ever be old enough or confident enough to get some, but interestingly we started playing off our little adventure as a different way to have fun until that finally happens one day. We were already planting seeds in our heads that it might be okay to be a little gay for a little while when it’s the easy way to have some dirty fun. Despite being fairly smart and tolerant kids and being very open minded, the social stigma on anything gay was still strong enough back then that we really didn’t want to be faggots. But on the other had there was something nervously exciting about it because it was even more taboo – why would anyone be gay of there wasn’t something fun about it? Because so far our tiny little taste of gayness made it all seem quite tempting, even just as a stand in for attention from girls.

Thankfully over the course of several minutes watching each other masturbate we actually talked through the inevitable awkwardness a bit and came to an agreement – none of us were gay so what we were doing couldn’t be gay, our excuse was that it’s just some mischievous fun for curiosity’s sake. As always we were just having fun doing something we’d been told not to do, knowing that there’s usually a correlation between how forbidden something is versus how fun it is. And even if it was a little gay it didn’t matter anyway because it would be our little secret. Nobody could make fun of us for acting like faggots because they’d never find out, so it didn’t even matter if what we were doing was totally and undeniably gay anyway. Most importantly of all we, we agreed to stay open minded and not judge each other for enjoying this minorly homoerotic activity. Even if one or more of us did turn out gay, that was fine too. All we were talking about was just a bit of masturbating together after all, it’s not like we actually thought we’d ever possibly do anything more hardcore like actually try having gay sex, so it was an easy excuse to make. Sure we were lying to ourselves thinking it wouldn’t lead to going at least a little bit further, but we could come up with justifications and excuses for any of our impulsive ideas those days. In the end it didn’t matter what anyone might think, nobody was going to know about any of this anyway, so all that mattered was our own thoughts and hang-ups about being gay or bi or whatever.

But that didn’t mean we easily got over those hang-ups right away, we’d barely done anything and none of us had any idea how far the other two wanted to push things. Even if we were all thinking the same thing, none of us were brave enough to bring it up as we just kept on sitting there and slowly masturbating. We all stroked our shafts so slowly and carefully that we weren’t even really jacking off, we were more just playing with ourselves and killing time as we talked, slowly rolling our foreskins up and down and enjoying the show. We talked about how awesome orgasms felt but we were in no rush to get there, we were having too much fun to want to stop. We ended up edging ourselves for a good long while, not wanting to go over the edge too fast and spoil the exciting mood. And I think we were also worried about the crash after orgasm and didn’t want to get hit with some guilt or regret in that moment. It was like we were teasing ourselves, thrilled about sharing some deep dark secrets for the first time and having some incredibly naughty fun, but still too scared to explore just how deep those secrets and strange desires might go, only barely poking past our comfort zone.

This went on for what felt like quite a while, and the whole time we were sitting there slowly playing with our dicks I kept thinking how I could possibly suggest pushing things a bit further without sounding like I’m gay. The more I looked at their hard dicks the more tempted I was to want to touch them and trade some hand jobs, or maybe even try something crazier than that. But I couldn’t think of an easy way to broach such a serious topic even though we were all sitting there playing with ourselves, and I just hoped that one of them might bring it up first. With how curious the three of us were I was fairly sure that both of them at least considered trying something a little more gay than just jacking off, but none of us had the guts to bring it up.

Being so caught up with trying not to act gay, it seemed clear that nothing too crazy was going to happen that night. Just jacking off together was a new and exciting enough thrill that there was no need to try and push things too far. If we ever wanted to try something even dirtier there’d be plenty of other sleepovers to give it a shot. So that night we just kept playing with ourselves until it got too hard to keep edging and holding back our orgasms. We’d managed to keep it going for what felt like quite a while, and eventually we couldn’t hold back anymore.

Acting surprisingly enthusiastic about everything, Jay suddenly said he was about to have an orgasm and he pushed himself over the edge without any hesitation. Me and Matt watched intently as Jay grabbed his dick harder and started stroking faster and faster, and it was fascinating to see as his whole body tensed up and he shivered. His orgasm seemed to last forever as he started breathing heavy, and he kept powering through it going faster and faster. When it was over he finally relaxed and laid there with his dick throbbing hard and twitching, and he didn’t even cover himself up. He just laid there out of breath and relaxing with his dick still out and hard as ever.

All three of us were still just a bit too young to actually ejaculate, so thankfully there was no sloppy mess of cum to have to worry about cleaning up. That was another thing we’d learned all about in sex education, so we knew we’d have to deal with squirting cum and wet dreams at some point soon in our lives, and for the time being we were just happy we were young enough not to have to worry about it yet. But not being able to shoot any cum didn’t mean we couldn’t have amazingly powerful orgasms, and I got excited as I quickly felt one coming on myself. After watching Jay finish himself off I was so turned on that I couldn’t hold back anymore, so I told the guys I was about to finish next.

As I felt that familiar tingle start working its way through my body I still couldn’t even believe what we were doing. Sure it was pretty tame compared to some of the dirty gay fantasies I was starting to have those days, but pushing myself over the edge as my two best friends watched me jack off was such an amazing new thrill. It was such a new and unusual feeling that my orgasm came on slow and was shockingly powerful, and my whole body tensed up and my toes curled over as I pushed myself past the point of no return. After edging for quite a while it felt like it was taking forever, and I stroked my dick harder and faster as I pushed through the single longest and most amazing orgasm of my entire life up until that point. My mind blanked out as the pulsing twitches took over, and I almost couldn’t breathe until the feeling eventually slowly started to fade. It felt absolutely amazing, and it was crazy that two best friends were watching it from a few feet away.

Still being so young and inexperienced, it was almost weird that neither me nor Jay had any kind of post-orgasm shame or guilty feelings about what we had just done. We all knew about the refractory period and heard about the instant regret that sometimes kicks in right after a good dirty session of jacking off, but I can honestly say I never got that feeling. You’d expect it to kick in even harder after doing something as shameful as jerking off in front of guys, but it just never happened. I only ever felt a little tired and smugly satisfied after a good masturbation session, never ashamed or dirty or regretful, and this was no different. But since this was a lot crazier than jacking off alone we knew it was a risk going in, we just didn’t really care, so it was a pleasant surprise not to switch to being disgusted with ourselves after the fact. We were just happy our little experiment was so much fun, and even right after having such a powerful orgasm I was still horny enough that I really wanted to see Matt finally finish himself off as well. Following Jay’s lead I didn’t even cover my dick after my orgasm, and the two of us sat there with our dicks still out and hard, encouraging Matt to go for it and have an orgasm too. Even in that strange post-orgasm mindset it was all super exciting to watch, and we almost couldn’t believe what we were doing. It wasn’t hard to stay excited when the whole thing was more about adrenaline fueled thrill seeking than any kind of real sexual satisfaction. The orgasms were just a bonus, the real fun was the thrill of doing exactly what we were told not to do and discovering that taboo equals fun.

Either Matt was still pretty far from coming or he was just more nervous than either of us, because it seemed to be taking forever for him to get there. But he was definitely horny and not nervous enough to stop, and he kept on stroking his dick harder and faster. With me and Jay staring at him it took a few more minutes until he was about to go over the edge too, and eventually it happened. He didn’t even need to say anything as he got closer and closer, we could see how his body was tensing up as he finally reached his orgasm. His dick twitched and throbbed in his hand as he took several deep breaths and then it was all over. He sighed a big sigh of relief and that was that, all three of us had just watched each other have big awesome orgasms. This had turned out to be such an awesome idea, and we were rather proud of ourselves for being so bold and open with each other.

Luckily Matt didn’t seem to feel any shame either in that post orgasmic brain fog, and we all had a little giggle at the silliness of what we’d just done. It was a pretty weird feeling and still exciting even after the fact, and we were all surprised with how amazing our orgasms felt. It was like the added taboo of jacking off with friends made it feel even better on top of all the nervous excitement, so without having to say it, we knew we’d be doing it again at the next sleepover. Whatever it was that we’d just discovered, it was definitely going to become our favourite new secret hobby and all our sleepovers were going to be a lot more fun from here on out. This experience had really proven just how close and trusting our 3-way BFF relationship truly was, and with our pact of secrecy we now shared a bond unlike anything else. It was so awesome to know that we could share our dirty secret hobby among ourselves without judgment – initially all I wanted was to be able to jerk off at our sleepovers without having to hide it, but now we’d accidentally discovered that jerking off together out in the open actually made it way more fun for whatever reason.

Still excited but feeling a little worn out, we covered ourselves back up and laid there almost in shock over what had just happened. We tried to go to bed but we were too wound up to fall asleep right away. And still worried about trying not to act too gay, we left it at that and changed the topic of conversation as we tried to sleep. I remained super curious and tempted by the thought of potentially taking things even further, but we were done for the night and I’d have to save my crazy ideas for next time. For all I knew Matt and Jay might have even been thinking the same thing, but I guess we’d all had enough for one night, and we did eventually go to sleep without any more mischief happening. But deep down I think we knew that this was just the start of something that could lead to places that we never thought we’d go.

🔞 Candy.AI 🔥 AI Sex Chat - Roleplay, Erotic Stories, Try for Free 🕹️

Please, Rate This Story:

(average: 3.76 out of 17 votes)