Playing With Dicks – How boyhood experiments turn into teenage degeneracy – Chapter 06

Chapter 6 – The Dungeon – After a wild night of blowjobs and humping at Grant & Chris’s place, the secret club finds its awesome new headquarters.

WARNING: For patient readers only!

PLAYING WITH DICKS is a very long novel, for context please go back and start reading at chapter 1, you will be lost if you try and pick up the story from here. Or if you’d like to skip ahead, go to the recap at the beginning of the next section and start there, this book will be divided into standalone parts with summaries in between, clearly marked in the titles.

Playing With Dicks

How boyhood experiments turn into teenage degeneracy

Chapter 6 – The Dungeon

Grant and Chris had told us a little bit about their house, and we hadn’t even been there to visit before our sleepover, which was a little weird considering how good friends we’d all become since they’d moved to the neighbourhood. They lived with Grant’s mom and Chris’s dad who’d been together for for many years, and despite coming from broken families they seemed to have a steady happy thing going with the new family arrangements. Grant didn’t know his real dad, Chris occasionally saw his real mom, and I guess with child support and alimony helping out they were doing pretty well financially. They told us they had their own little living room in the basement which they called “The Dungeon” where we could do whatever we want, and they couldn’t wait to show us. Sometimes being children of divorce has its perks.

And when me and Matt and Jay finally got there that Saturday after dinner and saw their basement suite for the first time, we instantly wondered why they didn’t always have friends over and make it into a regular hangout. They had the sweetest setup we’d ever seen, their living arrangement was enough to make any guy jealous. If they invited people over more often or if their parents let them throw some parties they’d totally be the most popular guys with the coolest place everyone would want to hang out at. It was almost like they lived in their own separate suite in the house, might as well have had their own apartment.

They each had their own little bedrooms beside a decent sive living room, and down a short hallway they had their own big bathroom with a huge custom glass shower stall. It looked like the basement was set up as a studio room or mini bar by the previous owners, and it converted perfectly into their own little play room / living room / chill out area. Calling it “The Dungeon” was pretty accurate, it had a dark red carpet and they had cheesy posters of dragons and stuff on the walls. It was well furnished with shelves full of toys and books, a pair of small old mismatched sofas, a decent sized tv with plenty of movies and video games, they even had a brand new expensive computer on a desk in the corner. The tiny ground level windows up close to the ceiling gave it a nice cozy feel, and they had cool little lamps all over the place to brighten it up. There were even these cool spikey foam squares all over the walls and ceiling like it used to be a studio or something. For a lower middle class family they’d done quite well for themselves, and we would have loved to hang out there anytime – even if weren’t secretly planning on sucking each other’s dicks all night. It really was the coolest setup any of us had, and it made us pretty jealous of the two of them.

Matt and Jay and I were used to waiting until our parents were asleep before we started fooling around at our sleepovers, but Grant and Chris were so eager that they wanted to get things going right away. After we had met their parents upstairs and took the tour of the basement downstairs, we were all alone down there and they insisted that we’d be left alone and could easily get away with doing anything we wanted well before bedtime. The two of them did it all the time, never waiting to hide in their bedrooms after bedtime and fooling around right out in the open of their little living room. Their reasoning was that the door to the basement and stairs down were loud as fuck – we’d easily hear if their parents were coming with plenty of time to stop and compose ourselves. They were right, there was so much advance warning of anyone coming down to check on us that there was plenty we could get away with, and I was more worried about the fact that anyone could look inside through the uncovered ground level windows. But someone would have to trespass on their front yard and trample their landscaping to actually get a good look inside, and they kept insisting they’ve been getting away with fooling around down there since the day they moved in. They had a point, their little basement suite really was such a perfect spot for us to have some secret taboo fun. This was definitely going to be a night to remember.

Being in new and unfamiliar territory we were hesitant to jump right in so quickly, but Grant and Chris kept insisting that it would be fine – they swore that fooled around out in their living room during the day all the time and it was never an issue. Matt and Jay and I were pretty nervous and not convinced, but they gave us a pretty hard sell on the idea anyway. Other than some of our secret outdoor spots the three of us had never fooled around somewhere we felt so open and exposed, and it felt super risky for some reason I couldn’t articulate. Not only was it a big open brightly lit room and we were we worried about their parents coming downstairs, and worst of all they didn’t even have blinds on the small windows above the sofas and anyone could easily see inside from their front yard. They swore up and down that none of that was an issue, saying they even tested how well you can see in from outside and said nobody could see in unless they actually pressed their face to the glass. It’s not like anyone was out in their yard to spy on us, and according to Grant and Chris we were just being paranoid and we were way less likely to get busted fooling around down there then in any of our riskier spots outside.

They made a pretty convincing point, we didn’t know their parents and were being too paranoid, they were well practiced and knew exactly what they could get away with. So it didn’t take much convincing, as soon as they were done showing us around they put the TV on for a distraction, and we all sat down and pulled our dicks out. First we started just jerking off, then jerking each other off, then as we really started getting horny we started sucking dicks all eager and enthusiastic, like we’d been dying to get back to it after hiding it from all the other guys we started the big circle jerks with that week.

I was still somewhat paranoid and kept my ears out expecting to hear someone come down the stairs, keeping my eyes on the uncovered windows expecting someone to appear there watching us. Something about it felt a little weird and almost too risky, but we just went for it anyway, and the longer we kept it up the more comfortable I slowly got.

As things started to get exciting, we decided to take a quick break long enough to unpack and set up our temporary beds. We rolled our pads and sleeping bags out on the floor of their little living room, and immediately got back to blowing each other. Only now we started spicing things up, we started doing 69, which was almost as much fun to watch as it was to do. I never realized how much watching each other and showing off part was such a huge factor in the fun of it all, but now that 5 of us were going at it there was more action to watch and a bigger audience to perform for. The way we were almost cheering each other on just encouraged us even more, everyone trying to outdo each other and suck dick longer and better. We ended up getting into a full on suck circle all going at it at the same time, with the TV still on as a distraction.

I was almost about to suggest we try squishing our dicks together and humping each other, the one and only thing me and Matt and Jay had tried but hadn’t told Grant and Chris about yet, and we had our beds out and ready anyway. But things came to a screeching halt when all of a sudden we heard the door open at the top of the stairs. We had exactly 14 stairs before whoever was coming down caught us in the act with dicks in our mouths. We all panicked and quickly stopped and covered up as the footsteps came our way, tucking our hard dicks back into our shorts and hurrying to pretend we were just finishing setting up the beds or something. We barely had a chance to spread out and act cool before Grant’s mom showed up and asked if we wanted a snack or anything before bedtime, they were making popcorn upstairs.

It was fucking nuts in my mind, my heart was racing because that was by far the closest call we’d ever had, we just barely dodged a bullet, literally seconds away from being caught red handed. But Grant and Chris played it off so cool and casual I couldn’t believe it, without skipping a beat they told her to bring some popcorn down, cold as ice like nothing was happening, just another average Saturday night for them. The way they so easily and instantly switched from sucking dick to acting normal was obviously a well practiced skill, and to them that wasn’t even close. When his mom turned to head back up the stairs, Grant just laughed it off like no big deal. So I tried not to make a big deal out of it either, even though it honestly kind of scared the shit out of me.

Luckily for me we had no choice but to stop and chill for a bit because there’d be a delivery of popcorn down the stairs in a few minutes, and we all re-composed ourselves and debated what to do. Popcorn gave us the idea to pick a movie to put on, so we browsed through their pretty sizeable collection and settled on some silly 90’s action comedy we’d all seen before. It was probably going to end up just being more background noise to fool around to eventually, but for the time being round 1 of sucking dick was done for the night.

Grant’s mom was a real sweetie and brought us not only popcorn but drinks too, and seeing us settling in to watch our movie she said goodnight, told us not to stay up too late so we didn’t sleep in all day, and went back up the stairs for the night. As nice as she was, hopefully that was going to be the last time we saw her until the morning.

I don’t know if the sudden interruption had killed the mood for everyone else too, but we actually sat down to watch the movie and enjoyed it without getting distracted and playing with our dicks again. We were still all just normal friends too and liked doing normal shit together, so it didn’t have to be all dick all the time, we still had all night for that and suddenly weren’t in such a rush anymore.

But less than 2 hours later, by the time the credits rolled it was getting late and the whole house had fallen silent. The parents upstairs must have gone to bed because we didn’t hear them stirring about above us anymore, so now they were fully 2 floors away from us in their upstairs bedroom. Grant and Chris started getting pillows and blankets out of their rooms so they could sleep out on the sofas in the same room as us, abandoning their perfectly good comfy beds for the sake of making it a real sleepover. I don’t think any of us were planning on doing much sleeping anyway.

Chris said he was going to take a quick shower and started stripping down to his underwear, and Grant said it was a good idea and that he would take a shower as well. None of us had thought to bring our towels and stuff, so me and Matt and Jay didn’t really know what to say, feeling kinda stupid we weren’t prepared. It got even weirder when Chris took of into the bathroom, and instead of Grant waiting his turn like we assumed he meant, he actually went to follow right behind Chris like they were going to shower together or something. Only he stopped to ask us if we wanted to come too, they had plenty of towels to lend us if they wanted.

Ok, taking a shower at a friend’s place is one thing, but was he really asking us to go in there all at the same time as them? Was this part of their nightly ritual of fun? Because if so count me in, I gladly agreed to follow along too and started peeling my clothes off. Jay suddenly got all excited to go along too, even though he was shocked they even suggested it, and Matt still seemed hesitant about it but grudgingly decided to follow us too. What else was he going to do, sit out there all by himself and read the rest of the movie credits?

My heart started racing with excitement again and I almost started shivering from all the adrenaline as we stripped down to our underwear, me and Jay wearing our tighty wighties and everyone else in boxers. We grabbed our toothbrushes and things and we all piled into the big bathroom together. Chris got the shower going, took his boxer shorts off and stepped in, and Grant went over to the sink and started brushing his teeth so casual, like sharing the bathroom was just completely and entirely normal.

If you really think about it, if we hadn’t been sneaking around and sucking each others dicks, this wasn’t even remotely gay or even that weird and had every reason to be totally normal. Guys use communal bathrooms and showers all the time at school and public pools and stuff, how is doing it at home any different? Their bathroom was definitely more than big enough to share, even the shower was big enough to fit more than one person at a time, all that was missing was the cubicle walls around the toilet and a few urinals on the wall. Maybe this really was just completely normal and not even sexual to them, or at least it might have been if they weren’t secret cocksuckers just like us. But it was definitely a little weird for me and Matt and Jay, we definitely never shared a bathroom like this, never watched each other take a shower.

Chris didn’t even have a shower curtain to to hide behind and didn’t seem to care, the shower only had a clear glass partition and no actual door to close. We could all see him clear as day, and he washed up like an exhibitionist putting on a show, like he got a kick out of us staring at him. Suddenly our original trio felt like the inexperienced noobies for once, and we didn’t know what to do, I guess we were just going to wait and take turns or something? It was just such a awkward position to be in, but doing new crazy stuff like this was a total thrill ride and we were having way too much fun.

Jay got comfortable quicker than I did and said he had to pee, went over to the toilet, slid his underwear off onto the floor, and started pissing a good long piss. I thought I had to pee too but my dick was already starting to get hard and I didn’t think I could piss through a boner, so I went over to the sink to brush my teeth instead. Even Matt started easing up, and taking turns is basically what we ended up doing, brushing our teeth and using draining our bladders.

But the shower was a different story. Instead of taking turns like we assumed they’d do, Grant being Grant just went ahead and peeled his boxers off and got into the shower along with his step brother before Chris was even done, and the two of them shared the spray of water side by side, ass cheek to ass cheek. The rest of us still stood there dumbfounded, until Chris finally finished and stepped out, nervously smiling at us with a huge erection as he grabbed a towel. Grant turned around and looked right at us through the glass, lathering his body up with soap, asking if anyone else was coming in as his dick stood up hard, pointing in our direction. There might have been only one shower head, but the glass stall was definitely big enough for all of us, so why not?

Jay was already naked so he stepped right in as soon as Grant invited us, and I wasn’t going to chicken out so I peeled my underwear off and followed right behind him. Grant politely made some room for us and stepped out of the stream of water so we could start washing up too, and ever the reluctant one, Matt got naked and slowly stepped into the shower after us. It still didn’t even feel all that sexual even though we all had diamond hard boners by then, and we really did take proper showers, trading time under the water and watching each other soap ourselves up. It was such a fun little bonus I wasn’t even expecting to get to all shower together, and I wished we all had this kind of confidence out in the public showers at the local pools. I wished public showers were like this and all boys would be so easy going about having boners around each other. If all boys were this cool about it then we’d never have to be nervous and shy being naked around each other, and spending time in change rooms would be way more fun!

It was a little nerve wracking to realize that Grant and Chris really were a lot more experienced than us in some ways, Grant really was starting to take the leadership role away from me, not just in their basement but with all those new recruits who’d joined in lately too. He was the main reason we managed to jerk off with almost every kid in the neighbourhood that week after all. On one hand I didn’t like not being in charge anymore, not knowing what’s coming next and not being able to set the pace – but on the other hand I loved being able to just follow along considering how casual and easygoing Grant was about being a total perverted faggot. It was nice not to have to be the one suggesting everything and having all the dirty ideas, and he was definitely better than me at goading everyone along into fulfilling his sick fantasies. I was really hoping he’d have plenty more perverted fantasies he was going to try and talk us into…

Chris was definitely way more of a silent type than his uninhibited step brother, but he was definitely just as much of a pervert as him and wasn’t the least but shy about it. While the other 4 of us were still in the shower not even fooling around yet and simply washing up, Chris stood there blatantly staring right at us as he started stroking his dick. He just stood there masturbating with one hand and drying himself off with the other, little mischievous grin on his face as he looked right at us. So far all the time in the bathroom together could have still been fairly innocent and non-sexual, but that facade started to fall as Chris started pleasuring himself to the sight of us 4 all naked and wet together in the shower. He seemed to be the one wanting to get things going that night, it was his idea to go take a shower after all. Maybe him and Grant already conspired, maybe they had this whole thing planned out before we even got there, and we were just playing into their hands.

Chris was even starting to go against all the excuses we told ourselves how we’re not really gay, the way he stood there thirstily admiring our bodies, staring at our hard dicks and pale butts as he jerked off and smiled. At first we had been telling ourselves that this was just all about the sexual thrill, we weren’t actually supposed to find each other attractive or think naked boys are hot, but that obviously wasn’t the case with him. It was almost awkward, but I liked the attention and got all excited as he checked my naked body out. Jay was having the time of his life too and kept smiling like an idiot throughout, obviously overjoyed and overwhelmed with so many hard dicks around him on all sides. It really was almost too much too fast, such a new interesting experience in an unfamiliar house.

Matt was the only one who still seemed a little nervous and hesitant about the situation, so he was actually the next one to get back out of the shower after a quick 2 minute rinse, leaving just me and Jay and Grant in there. He started drying himself off obviously feeling a bit awkward, looking like he was ready to leave the bathroom and head to bed. But Grant had other ideas, and he asked us if we wanted to start playing with our dicks right then and there in the shower where it’s fun, or if we wanted to head back to the boring living room, obviously implying his preference. I would have been cool either way, but since I’d never even fooled around in the shower with Matt or Jay before I couldn’t resist the temptation, none of us could. When we planned this sleepover I never imagined we’d all end up playing in the shower together, I could hardly believe it was happening! I was so jealous that this was how Grant and Chris lived every day, and so were Matt and Jay because we all stuck around to see where this was headed.

That’s when the discussion about grinding our dicks together and humping finally came up. Grant was all eager to show us how to press our dicks together and hump like it was some new cool thing we hadn’t done before, so we had to tell them that of course we’d tried that before, and he wasn’t even surprised. It was such a logical thing it was weird we hadn’t even brought it up yet, and the only new part about it was that we usually humped laying down in bed, never tried it in the shower before, obviously.

But that’s what Grant wanted to do, and I was more than happy to volunteer myself for him to grind against. Jay seemed almost disappointed that I beat him to it, so he stood there and watched as me and Grant stepped up to each other face to face, carefully lined our dicks up vertical between our bellies and squished them together. We pressed our hips and torsos together and started pumping and thrusting, and the way our wet skin slid against each other under the spray of hot water felt amazing. I guess you couldn’t even call it dry humping anymore, and the wet slippery sensation was way better than doing it bone dry in bed. No need to worry about pushing too hard or stretching some skin the wrong way, everything just slipped and slid and felt great.

Chris just kept standing there happily stroking his dick and watching, but Jay noticed that Matt was looking a little left out and stepped out of the shower to join him. Still soaking wet, Jay stopped Matt from drying himself and backed his ass up against the countertop, pressed their cocks together as he trapped him there, and started grinding against him. Now that we were all clean and done showering anyway, Grant finally turned the water off but kept humping me standing in the stall. He pressed my naked body right up back to the clear glass, giving everyone a good look at my bare butt cheeks squeezing and pulsating against the glass as we rubbed our dicks together. I looked over my shoulder and everyone was watching everyone go at it, and the big mirror gave us all kinds of extra views of ourselves and the action we’d never seen before. It was pretty crowded with 5 of us in there, but it looked like 10 of with reflection.

This was the wildest thing I’d ever done, our craziest most risky bit of fooling around by far. All 5 of us totally naked, hiding in the bathroom together, not even a care in the world about getting busted apparently. The paranoid part of me kept thinking what the fuck would happen if one of their parents came downstairs only to find the living room and both bedrooms empty, what wild excuse we could possibly make up for all of us being naked in the bathroom together.

There were only two possible explanations why Grant and Chris were so comfortable doing wild shit like this and could be so sure we’d get away with it – either their parents already knew the two of them openly shared bath time together like they were still little kids or something, and it was normal enough in their household that the same uninhibited attitude extended to us as guests too. But that would only make sense if we were still 5 years old and needed adult supervision in the bath, nobody shares the bathroom like this at this age! So it must have been the much more likely explanation that they were just certain enough their parents wouldn’t come downstairs after bedtime. Even though their little dungeon was arguably the safest place for us to fool around, it still felt like they had to push the limits and take the biggest possible risks we could get away with.

We quickly started taking turns and switching off who got to hump who so we all had a try, and as if the situation wasn’t already exciting enough, a few minutes later Grant finally broke the ice on the last huge taboo subject we still hadn’t dared talk about up until that point. We were barely starting to talk about what else we wanted to do that night, and he dropped the bomb of a topic on us like it was so casual and no big deal.

“So, did you guys ever think about trying anal?” Grant asked, still somehow sounding cool even tho it was the gayest thing we’d ever heard anyone say. It was exactly what I had been too scared to bring up but always wanted to know, and I got another fresh adrenaline rush trying to think of a way to answer. All this time I’d been hoping one of them would be brave enough to bring it up, but it was still such a shock to hear him actually say it, and I didn’t know if I should be excited or scared. I wanted to tell him I’d been dying to try and beg him to teach us all about it, but I held my tongue, not wanting to speak for Matt or Jay, I didn’t even know what they’d think. But I had to say something because neither of them wanted to answer.

“Why? Have you guys tried it?” I asked back, using the classic deflection technique of turning the question back around on them.

“Well, umm, yeah we sort of tried,” Grant replied slowly, “aren’t you guys curious? You seriously never tried?”

“We never tried,” I said, “but it sounds fun to me, I kinda always wanted too, have you guys actually done it?” I asked nervously. Matt and Jay looked at me in shock, surprised I never confessed that to them, but they never brought it up and I suddenly didn’t care what they thought, I wasn’t going to lie to Grant and fuck this chance up.

“We tried it a few times a while ago,” Grant admitted, and he went on hesitantly, “but we never figured out how to actually stick it in properly.” Chris nodded silently, and I was still so shocked I didn’t know what to say. I was excited to hear they’d been a lot more adventurous than us and actually tried fucking, but at the same time it was disappointing to hear they didn’t actually figure how to do it. It couldn’t be that difficult, could it?

I told Grant I’d try it with them if they wanted to try again, and Jay was curious enough he said he would try it too, and we started wondering if we could maybe figure it out between all of us. Except Matt apparently though, we’d finally pushed things too far for him and he said we were crazy. He immediately brought up the first most obvious concern anyone should have about putting anything inside their ass, but he didn’t seem completely disgusted by the whole idea either, at least not if there might be a workaround for that.

We knew nothing about the actual logistics of anal sex, but Grant was clever enough to tell him that’s why we should try in the bathroom, everything is right here if it goes wrong and you gotta clean up. I didn’t even care at that point, I was already sold on the idea and was ready to ask who goes first. Jay was ready to give it a shot too, but the best Matt could do was say he’d watch us try and then make his mind up about it. His hesitation didn’t matter though, this idea was finally disgusting enough that his attitude was understandable. It didn’t matter if he was going to try it or not, we weren’t going to let our obsession with keeping everything all fair and even all the time stop us from this exciting of an experiment.

The only thing left to do was decide who should try with who, and Grant said since he and Chris already tried, me and Jay should go first because we never did it before. And not trying to offend Jay, but since his dick was a bit smaller it might fit easier. Suddenly it was all on me, my hole had to be the first one we try and penetrate, which was totally fair since I was the most curious and eager. So I nervously asked Grant and Chris is they knew what we should do, but they were flying as blind as we were and the only advice Grant had is that I should just bend over and spread my ass cheeks, like duh.

Almost shaking with excitement, I went over to the counter and did what I was told, bending forward toward the mirror and spreading my legs. Jay looked at me in the mirror with an expression of “holy shit I can’t believe we’re doing this” on his face as he stepped up behind me, hard little dick in one hand. Everyone gathered around real close to watch as he brought his cock within thrusting distance of my hole, and he gently tried to push the tip of his dick in. My ass clenched and I flinched the instant I felt the tiny bit of pressure on my hole, it just felt way too weird. But it didn’t hurt, so I told him to try again, and he pushed a little harder. This time I actually felt the hard round shape of his cock head try to open my hole and sneak in, but I flinched even harder and it still didn’t work.

His dick was just slipping up or down my ass crack instead of going in my hole, but I didn’t give up and tried to relax, desperate to make it work. We failed at a few more tries, then he finally seemed to get the alignment just right and it felt like it actually slipped in for a fraction of a second, but he pulled back and said it didn’t feel right. It was hard to tell, it was such a weird sensation and didn’t exactly feel good for me either. So we gave up and I told Jay to switch spots with me, I wanted to try on him, maybe that would work.

So he bent over the counter and I got behind him, and he reached back to hold his ass cheeks apart as I looked down to line my dick up with his tight little pink hole. I carefully made contact barely touching my tip and trying to center it as best as I could, and just that little tickle already made Jay squirm. He tried to calm himself down as I tried to push my dick into him, but we failed just the same way. He flinched, his hole was too tight, my dick kept slipping off track one way or another – for something that sounded so simple, fucking each other in the ass was surprisingly difficult and elusive.

We quickly realized we weren’t doing something quite right and that it wasn’t going to work, so we took a break to watch Grant and Chris try again on each other. They said it was a long time since they last tried and had since gave up on it, and even though they hadn’t learned anything new since then they were at least motivated to try again, especially now with us there to impress. So Chris let Grant try and fuck him first, and just watching them get into position was the wildest thing I’d ever seen. Once again I was just shocked, couldn’t even believe what I was seeing or doing. A group of five 10 to 12 year old boys all trying to fuck each other, nobody ever imagines stuff like this ever happens, yet there we were doing it just for the fun of it.

They gave it a good try but Chris was way too tight and sensitive , I watched so close and carefully I swore I almost saw the tip of Grant’s dick go a little bit inside him, but they didn’t get any further than we did. They tried even more than we did, but it just wasn’t working and Chris actually told Grant to stop. With Matt still unwilling to even try unless we figured it out, we had one last chance for them to trade places and hopefully make progress. So far the 4 of us weren’t exactly doing a good job selling the idea to our 5th and most nervous friend.

The two of them nervously switched spots, and the whole vibe seemed to change a bit like we were all kind of on the same level again now that we were in uncharted territory together. None of us had taken it this far and succeeded before so experience didn’t matter, and other than Matt we all seemed desperate to make it happen. So Grant bent over and spread his cheeks for Chris, and they lined it up and gave it a try.

At first it wasn’t working for them either, but then suddenly Chris seemed to line things up just right and pushed a little too hard, almost violently like he was getting Grant back for hurting him, and we all watched as his dick actually penetrated and halfway disappeared inside into his hole. Grant winced and flinched harder than any of us and told him to pull out, so Chris backed off. It was pretty obvious it didn’t feel great, but it was the closest any of us had gotten. That tiny bit of progress was enough to encourage them to try a few more times, but it just wasn’t working, as soon as Chris pushed his head in a tiny bit Grant would tell him to stop. They quickly gave up too when they realized Grant was just too tense, and we didn’t know where to go from there.

It was a weird mix of emotions. Excited that we had the balls to even try it, but devastated that we failed and couldn’t figure out something that sounded so simple, the first one of our experiments that didn’t work out… Worried that we’d never figure it out or have the balls to try again, but hopeful that this was just a hiccup and a sign of more experiments to come… Not sure if I wanted to keep trying, or just give it a rest… I mean we’d kind of figured it out because there were definitely some quick little short penetrations happening and that was encouraging, but it was disappointing that it was uncomfortable enough that we all kind of chickened out. There had to be some trick to it we didn’t know or something, but we weren’t willing to put in the work to try and blindly figure it out.

We agreed to forget about it for now, and we finished drying off from the shower. It wasn’t as much of a mood killer as it could have been, maybe a bit of vindication for Matt, and we played it cool and agreed to head to bed. Not to sleep, but back to the beds in the living room room where it was dry and comfy and soft and cozy.

The whole anal thing went on the side burner and we started having an absolutely wild and crazy night despite it. We didn’t put any pj’s on and I don’t think Grant or Chris even had any, and we all went back to the living room still totally naked with our dicks all rock hard. We immediately started sucking each other’s dicks, not giving a shit or not even realizing we’d just been prodding each other’s butts with them, already going ass to mouth without even figuring out the anal part first. We picked up where we left off earlier that night when Grant’s mom interrupted us, and we did a bunch of 69s and switching partners, until we ended up in one big suck circle again.

One by one we started making each other cum, nice easy dry orgasms in each other’s mouths, and it didn’t take long because we were already super horny and worked up from fooling around in the bathroom. Whoever came first would just duck out of the circle, and we’d tighten up to 4, then 3, and not that it was a contest but me and Chris ended up lasting the longest, ending up in a 69. We pushed each over the edge at almost the same time, pretty close to simultaneously making each other cum as everyone else kept watching.

After that we lounged around all naked, almost starting to sweat from all the effort as we all recovered for a little while, but our dicks didn’t even get soft and we all somehow managed to stay horny. Me and Chris had barely finished sucking each other off before Jay crawled on top of Grant and started humping him, and barely a few minutes later we were all taking turns humping each other, immediately going for another round. Even Matt was back in his element and loving every second of it, and we were so numbed from sucking each other off that the humping went on for a good long time.

Some more blowjobs entered the mix eventually too, we liked how a slippery wet dick felt when we were grinding our shafts together and took full advantage of that. We were having so much fun that we didn’t even bring the topic of anal back up, even though the trick we needed to figure it out was staring us right in the face.

After another round of making each other cum either by humping or with our mouths, it was finally late enough to call it a night and go to bed for real. As one last final challenge of the night, Grant and Chris said they had been sleeping naked lately and dared us to all do the same. So we all crawled into our sleeping bags in the nude, and tried to fall asleep. I just hoped by bag wouldn’t unzip and I wouldn’t roll halfway out during the night only for one of their parents to come down in the morning and see my bare ass or dick.

It took a while for us to calm down enough to fall asleep, and as we drifted off we casually chatted and fantasized about the rest of the secret club and all the wild theoretical scenarios we’d love to get into. We wondered if we should try to get all the other boys to try sucking dick too and who among them might actually be into it. We talked about girls a bunch and theorized about pussy and getting laid, like we had to reiterate and we weren’t gay and this was all just some fun or practice along the way or whatever. We tried to justify it all as no big deal, but in our minds we knew there was something more to this, and things were bound to keep going and get even wilder. That night was so much fun that of course we were going to pick up right where we left off as soon as we could.

The next morning only confirmed that as I woke up to find Grant on top of Chris, both naked and uncovered, already humping and grinding each other on the sofa. It seemed like an excessively risky way to deal with morning wood, and Matt and Jay were being a lot more careful just laying there jerking off and watching them. It felt weird being the last one to wake up and open my eyes to them already fooling around without me, I was almost mad they didn’t wake me up, wondering what I’d missed. But I was more horny than angry as I rubbed the sleep out of my eyes, and after a bit of a morning stretch I gladly unzipped my sleeping bag wide open and started stroking my dick too. What a crazy cool way to wake up!

The sound of footsteps above us meant their parents were awake by then, so I was a little worried that Grant’s mom would come down to check on us soon, but I was getting used to following their lead, and if they weren’t worried about it I figured I shouldn’t worry either. The two of them must have been humping for a while by then because Chris came quick, then Grant got off him and finished himself off a few seconds later. That left me, Matt and Jay still playing with ourselves but too nervous to try anything other than jerking off, so we all sped up and quickly and quietly finished ourselves off, like we were more interested in killing our morning boners than actually having some fun with it. But it was fun anyway and an interesting way to start the day, setting the mood for the whole rest of the weekend.

We eventually put some clothes on and went upstairs for breakfast, and it was a bit weird hanging out with their parents and trying to act normal after everything that had happened. It was the most permissive household we’d ever encountered, the amount of freedom Grant and Chris had was unusual for their age, and they were the coolest friends to have because of it. After we finished breakfast and before the 5 of us went to go take off gallivanting through the neighbourhood, their parents told us that we were welcome back over there anytime. Even though we were stoked to go play outside by then, I really hoped that their house would become our default hangout. Because as far as running a secret gay sex club for all the boys, that little dungeon of a basement suite would sure make the perfect headquarters.

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