Playing With Dicks – How boyhood experiments turn into teenage degeneracy – Chapter 01

Chapters 1 – Sex-ed – The spark that started years of secret taboo fun, from “show me yours, I’ll show you mine” to much, much more.

WARNING: For patient readers only!

PLAYING WITH DICKS is a very long novel I’ve been working on for a very long time, debuting right here for the first time. Check the word before you start reading, and know this is only one chapter of probably 20+, barely an introduction. The whole full length novel will be all the highlights of my sex life starting at a young age, from innocent boyhood experiments around 11 all the way through to wild teenage degeneracy around 16+, all written out in great detail so it’s properly documented. This is STILL A DRAFT and INCOMPLETE even though I’ve been writing and re-writing bits and pieces of it for years, so any and all criticism and editing advice is more than welcome as I try to wrestle this beast of a story into something readable.

This is a 100% true story about some very naughty boys (and a girl or 2), only names have been changed for anonymity, and conversations have been loosely paraphrased from my recollection. But I will tell you this happened in a random suburb of Vancouver BC back around the turn of the millennium. This is also largely based on a diary I have kept most of my life in which I documented most of my sexual encounters, so my obsession with writing about it goes all the way back to when it all happened. This is a sexual autobiography, everything you are about to read are real events from my past.

Thanks for reading! xoxoxo

Playing With Dicks

How boyhood experiments turn into teenage degeneracy

Chapter 1 – Sex Ed

For most of my childhood my family lived in a huge suburban apartment complex, and if it had been closer to the inner city some people might even call it a ghetto. But it was way out on the edge of suburbia and wasn’t all that dumpy or crime ridden, it was a surprisingly nice place even though it was definitely a low income neighbourhood. It was a lone group of apartment buildings among a sea of detached single family houses in the typical urban sprawl, and a lot of young families called it home because it was a cheap place to raise kids. There were playgrounds in the common yards, a beautiful park with some pretty wild forest right next door, a little private indoor pool for the tenants, and only a short walk to the nearby schools and a corner store across the street.

Because it was such an ideal place for young families, there were always tons of kids paying outside, even kids who didn’t live in the apartments came there to play on our playgrounds or meet up with all their friends or swim in our pool. And it was long enough ago that helicopter parenting wasn’t a huge thing yet, most parents let their kids roam free and play outside entirely unsupervised back then. It was a paradise of anarchy for youngsters compared to how some kids grow up these days, and it was where I met and started hanging out with my two best friends.

Matt was a few months younger than me and one grade below me in school, and we first hit it off and started hanging out when our parents became good friends with each other. Jay was a little over a year younger than me and also one grade below me, and we probably wouldn’t have hung out with him if our parents weren’t all friends with his and did a lot of socializing together. All three of us started out as kind of losers and social outcasts at school, so we all quickly became close friends despite being in different grades at school and not meeting organically like most friends do. With how often our parents all hung out, we didn’t have much choice but to become friends as we were forced to spend so much time together, so it was just blind luck that we ended up having tons in common and all three of us really hit it off.

The three of us were all pretty geeky kids, fairly smart for our ages and into all the same nerdy stuff. We liked the same shows and movies, we each had decent LEGO collections and video games we could borrow and trade with each other, and we loved hanging out together. It quickly turned into the kind of super close childhood friendship where we shared secrets and got into all kinds of mischief together, and soon the three of us were an inseparable trio of BFFs. Outside of school we did absolutely everything together.

Like so many kids at that age, one of our favourite things to do was having sleepovers. Since our parents were all close friends they let us have sleepovers almost every weekend, trading off who’s place we stayed at. For our parents it was like taking a little break from parenting, trading off who’d take care of us for an entire weekend while the rest of them had us out of their hair for a while, so they were all too eager to send us off and be rid of us on Friday and Saturday nights. We had so much fun spending weekends together and it quickly made our friendship even closer.

For the first little while when we were still very young, those sleepovers were as innocent as they could be. We’d hang out and play video games or watch movies late into the evening, then be grudgingly sent to bed at bedtime only to stay awake talking quietly about anything and everything late into the night. It was those late nights talking ourselves to sleep when we started sharing our deepest secrets and really started to bond, and little did we know what it would eventually turn into.

As far back as I can remember I’d kind of always known how to masturbate. I must have discovered it at a ridiculously young age because I don’t remember a time when I didn’t know how to rub my dick just right to get that amazing feeling of orgasm, and I was doing it regularly before I was even old enough to understand what was going on. But between the age of 7 and 9 it all slowly started to make sense, and we even started learning all about erections and masturbation and orgasms in overly detailed sex-ed classes at school.

I knew enough to keep my masturbating to myself, but I loved rubbing my dick so much that I would pleasure myself in bed every single night, and often in the bath or shower as well. In bed I’d usually hump my hand laying face down, rubbing my shaft and thinking about fucking hot girls. In the shower I taught myself how to stroke my cock as it was growing longer, and I’d imagine myself getting blowjobs from all my crushes. I was so obsessed with it that it became a nightly routine and I almost needed to have a nice big orgasm just to fall asleep, and I loved fantasizing about all kinds of dirty stuff while pleasuring myself in bed at night. Quite often I’d even linger in bed in the mornings to jerk off before starting my day, which is real easy when you’re still so young you can’t even squirt cum yet and don’t have to worry about making a mess. As soon as I was old enough that I knew what I was doing and that it was kind of “dirty” or whatever, that only made me enjoy my secret hobby even more. I’d had just enough of “the talk” and sex-ed to know it wasn’t anything to be ashamed of, just something to keep entirely to yourself. I was a masturbation feind and never felt one bit guilty about it, not even in those moments of clarity right after giving myself a powerful orgasm.

And since I was becoming so obsessed with masturbating every night, the worst part of the regular sleepovers with Matt and Jay was the lack of privacy for my nightly jerk off session. Not being able rub one out in bed right before going to sleep was annoying as hell. Sure our parents would always leave us alone after bedtime and didn’t even bother checking in on us, but I was too scared of my best friends catching me to try and jerk off in the same room as them. As close friends as the three of us were, I didn’t want them to make fun of me, I didn’t know what they’d think if they busted me pleasuring myself. Even though deep down I knew it wasn’t anything to be ashamed of and that Matt and Jay probably masturbated just as much as I do, it was still something a bit too shameful to admit, not something I ever imagined we’d ever talk openly about let alone do around each other. As fun as our sleepovers were, it did kind of suck not to be able to have my normal nightly routine of pleasuring myself before falling asleep.

But I was such a horny kid that the temptation was too much to handle, and it got to a point where I couldn’t resist. Whenever I sprung a boner while laying in bed it eventually became impossible not to touch myself, even with my best friends laying next to me, and I started thinking I could get away with a quick wank as long as I was subtle enough that Matt and Jay wouldn’t notice. So at some point when I was probably 10 or 11, I started quietly and secretly masturbating in the dark at our sleepovers – but at only whenever I thought they had fallen asleep before me. I was extra careful not to be obvious about it in case they were still awake so they didn’t catch me, and it ended up being a whole new thrill to rub my dick all the way to orgasm with my two best friends lying next to me, clueless to what I was doing. That added risk factor of potentially getting caught made it a lot more exciting than normal jerking off on my own, and that realization was the beginning of an ever escalating risk tolerance and thrill seeking.

It was so fun to get away with it while they were so close by, so much fun in fact that I started getting a little more daring and risky with it as time went on. After while of getting away with it and my friends not even realizing what I was doing, I got more confident and I wasn’t even waiting for them to fall asleep anymore. I’d just slowly and subtly jerk off under my blanket in the dark as we layed there and talked, hoping they didn’t notice what was going on, and they still didn’t clue in. The craziest part was pushing myself over the edge and having an orgasm while we chatted about whatever, trying not to breathe too funny to give myself away. And sometimes I couldn’t help but wonder if they noticed what I was doing but just didn’t say anything, or if they might even be doing the same thing. I kind of assumed they liked to mastubate too – it’s supposed to be common knowledge that all guys jerk off, and maybe we were all hiding the same secret. Maybe they wanted to jerk off too and we were all being too chickenshit to admit it. But if jerking off is just a normal nightly routine for healthy boys, why are we hiding it from each other?

For a preteen boy, I started thinking about it more than I should have. And then when we started getting more of that new age sex education in school, I started obsessing about it like crazy.

Around that adolescent age masturbation is so awesome that it was pretty obvious everyone must be doing it, but no normal boy that age would ever admit openly or talk about. It felt so good and was so addictive that I assumed that everybody would be doing it, and that’s exactly what our sex-ed classes taught us anyway, just confirming what I already knew. All our teachers told us the same thing about masturbating in a weirdly affirming way, how it’s a normal and natural part of growing up and everyone does it, even as adults, so we shouldn’t feel ashamed about it at all – just enjoy how good it feels, but for decency’s sake keep it to yourself. I still remember the line my 7th grade teacher used, saying that there’s two types of guys – those who admit they like to masturbate, and those who are lying. It was so awkward to hear from a male authority figure, because with one hilarious line he’d not only subtly confessed that he likes to jerk off in front of his class, but he also outed all us boys as masturbators in front of all our friends and all the girls, and somehow made it seem cool at the same time. It helped that we had the “cool” teacher who everyone loved and hung on his every word.

Some parts of those sex-ed lessons were borderline inappropriate for kids around our age, even teaching us how bathtime and bedtime were the best times to have some privacy to pleasure ourselves, and even teaching both sexes about the different basic techniques how to stroke your dick or rub your pussy, right there in the co-ed class of 6th or 7th graders, boys and girls all learning together almost too openly. It was among the first wave of these more progressive sex-ed programs, and I don’t think our parents realized what they were even teaching us, or the overly positive encouraging way they taught it. We even had the anonymous Q&A box where you could write your wildest or stupidest sex related questions without any judgment, and our teacher answered them all. I remember sitting through those awkward courses and being just as fascinated by my classmates’ reactions as I was by the learning material itself. And they left out just enough detail to leave us all super curious about what else there was to know about sex, and I got a little obsessive thinking about it.

I can almost understand why some parents think sex-ed goes too far, almost like some kind of grooming. Maybe those lessons were almost too graphic and went into too much detail, because any kid who’d never thought about masturbating before that point sure knew how to after those lessons. And co-ed with all the boys and girls mixed together, it was like they were teaching us boys how to finger bang chicks and girls how to give hand jobs, in 7th grade. The way masturbation was framed like everyone does it totally robbed all us of any excuses to pretend we were too innocent or prudish to jack off, making it seem like somehow you’re the weird one if you DON’T try it. We even learned about the refractory period after orgasm, all while teaching us that there should be absolutely no shame in it and we should never feel bad for exploring our own bodies. The emphasis on not shaming was so strong they were already teaching us how to mentally deal with post nut clarity, telling us there’s no reason to feel guilty about it after the fact.

Some parents would be horrified to know what we were learning, but to us it was all absolutely amazing and the taboos around it made it so exciting to learn about. It definitely piqued curiosity and anyone too scared or ashamed about it would easily be inspired to try pleasuring themselves after learning so much and being told it’s just a normal thing that everyone does. Despite the overly detailed and graphic nature of those lessons, it didn’t change how taboo so much of the subject matter was, and they drilled it into our heads to keep our private lives private and how sex is definitely to be saved for when we’re older and find the right person etc etc. All the stranger danger and how not to get molested lessons were in there too, but it was everything else we learned that made the taboo world of sex seem so dangerously appealing. Supposedly we were just being taught for our own good so we didn’t go learning from the wrong sources, like as if we were mature enough to just file the information away and then stop thinking about it too much. Kids are gonna do what kids are gonna do, which is obsess and experiment and push boundaries.

After all that, even at that young age, deep down I knew that Matt and Jay both probably loved jacking off as much as I did, we just didn’t have the guts to admit it to each other. We kept it to ourselves like the well behaved boys we were, fully aware how inappropriate even talking about it together would be. All 3 of us still had pretty conservative parents and not too lax of an upbringing, especially for that neighbourhood, and we were among the “good kids”, smart for our age and well behaved as far as our parents knew. So for the most part we did what we were told at first – we learned, we filed the information away, and assumed we’d never have any real sexual experiences until we got older and got girlfriends. Plus we were all supposedly straight, and even mentioning anything about it would be gay and weird, right? It was just this weird unspoken thing, we all knew jerking off is awesome and that we all do it, we just don’t talk about it, that’s too awkward, too gay.

But me, Matt and Jay were becoming such close friends and shared in so much other mischievous fun that I was tempted to open up to them about it. Even though they were a grade below me in school I knew they’d had basically all the same sex-ed lessons I remembered from the year before. And so much of the basic education we’d gotten was so focused on telling us what not to do, keeping your private parts private, saying no to any sexual contact, waiting til we’re grown up etc. The fact that we weren’t even supposed to talk about anything remotely sexual only made me want to do it more. Since learning and talking about sex was so exciting in class, maybe it’d be fun to keep talking and explore the idea with my two best friends. Because it really did start seeming stupid to be too shy to jack off next to each other at our sleepovers, knowing we all probably wanted to, but were just too scared to admit it. If we all did it and all had the same secret, then what’s the point of pretending we don’t, punishing ourselves by not having the guts to just jack off in the same room. If doing it alone is so much fun then maybe doing it with friends will be even more fun, and way more of a thrill because it’s forbidden.

I really hoped my two best friends felt the same way, because even though I knew I wasn’t gay, some part of me really did want to see their dicks get hard and watch how they pleasure themselves. I already knew how secretly jerking off next to them made it way more exciting for me, so maybe just admitting it and doing it openly would be even more of a thrill for all of us. It didn’t even have to be a big thing or be gay in any way, I just wanted to be able to jerk off without hiding it. After all we shared pretty much everything and knew all of each other’s deepest darkest secrets already, and the most fun we ever had hanging out was all the mischievous fun we got into together. It was a recipe for something devious to happen, all we needed was some courage.

I began fantasizing about showing Matt and Jay my dick and letting them watch me jack off, and I wondered if they’d ever admit to having the same curiosity. Pretty soon I was getting horny enough that I almost wished they would catch me in the act stroking my dick at one of our sleepovers and maybe something fun might come of it, but I was still too scared to talk openly about my weird almost gay seeming desires. That was probably the only thing stopping me at that point – admitting you like to masturbate is one thing, but I didn’t want to look gay by being so damn curious and bringing it up around my male friends. I didn’t want to look like a faggot so I didn’t have the guts to bring it up, and that’s why I wished they’d just catch me in the act and see what happens. I sure didn’t feel gay or have any kind of romantic feelings or crushes on any guys, I really was just extremely curious and horny and excited about something so taboo.

Not everything we knew about sex came from our basic sex-ed classes either, and just through exposure to pop culture we already knew a lot more about being gay than anyone our age probably should. I was also dangerously curious about all that gay stuff we’d all heard about, I didn’t even care about whatever social stigma might be attached to it, and since the topic of homosexuality was only glossed over in our sex-ed classes, it only further piqued my interest and was the most intriguing taboo of them all. I just wanted to know what all the fuss is about and why being gay was such a big deal – even though it was so frowned upon by all our peers, I couldn’t help but wonder if it might secretly be awesome. I desperately wanted to know if my two best friends felt the same way at all, and boys being boys I’d find out soon enough.

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

Please, Rate This Story:

(average: 3.95 out of 19 votes)