Rules of Masturbation
by Jason Kason



  1. For all boys (including sixth formers), masturbation is limited to stimulation of the penis. It is strictly forbidden for anyone to attempt to masturbate anally.


For years I read that rule as forbidding boys from masturbating ‘annually’. I thought maybe some guys had tried to curb their wanking to just once a year (allowing themselves a little Christmas treat perhaps?) and had ended up turning into total nutcases because of it.

When I was in the upper sixth, a boy in my year called Adrian Stanton told me what the rule really meant.  We all had single rooms by then – one of the few perks of being in the final year at the school – and for any boys who were so inclined, sexual relationships became far easier to conduct on the quiet.

Some boys coupled together to suck each other off.  While I did occasionally partake in a tit-for-tat blowjob when I was horny enough, I never had a regular partner and was never part of a ‘couple’ as such.

A few notorious boys – and we had two in my boarding house – got together for something far more taboo than cocksucking.  They weren’t talked about much and certainly weren’t openly derided for it, but we all knew that behind certain locked bedroom doors, such boys were indulging in what was quietly referred to as ‘brown-dicking’.

In my house it was widely assumed that Simon Rowley was brown-dicking Edward Poulton.  They’d been extremely close since third form and there were rumours that the housemaster had once caught them going at it around the back of his garage.  At the end of fifth form disco the two of them had danced together and a friend of a friend had said he’d once seen them having a full snog with each other at the back of the common room.

Such things were whispered about and chuckled over, but I don’t remember Rowley and Poulton being singled out in a belligerent way.  In a small school housing six hundred randy boys all pumped full of testosterone, the very air seemed saturated with sexual tension.  If a few enterprising souls had found a novel way of relieving that tension, then as long as they were fairly discreet about it I think the general consensus was good luck to them!

Not that I even knew what ‘brown-dicking’ meant – at least not during my first few years at the school.  I was just aware that certain boys were supposedly brown-dicking others and that for some obscure reason, that made the rest of us titter.

I think I must have been in the fifth form by the time I had the guts to ask a friend what brown-dicking actually meant.  His name was Stephen Hudson and I asked him during a cricket match when we were sitting on the sidelines waiting to bat.

“You know what it means,” he smirked.  “Everyone knows what brown-dicking is!”

“Except for me it would seem!”

He glanced around and lowered his voice.  “It’s what you call it when two boys have sex.”

“When two boys have sex?” I laughed.  “Don’t be stupid!  Boys can’t have sex with each other!”

“Of course they can!” he laughed back.  “They do it up the bum instead of using a fanny!”

“Do what up the bum?”

“Oh come on!” he kept laughing, amused by my naivety rather than making fun of me.  “You can’t tell me you don’t know how gay-boys do it!”

“I honestly don’t,” I shrugged.  “I never really thought about it to be honest.”

He moved closer to me and dropped his voice even lower so it was a conspiratorial whisper.  “They sperm off up each other’s arses!”

“Why on earth would they do that?” I asked, feeling mildly repulsed.

“For sex!” he hissed, sounding like he was getting exasperated.  “It’s like spunking up with your dick inside a fanny, only they do it to other lads and use the arsehole instead.”

“Oh right,” I replied.  “And do they try to think of it as a fanny?”

“Of course they don’t,” he whispered, his mouth cracking into a smile again.  “They like that they’re dumping a load of their junk up another boy’s bunghole – it makes them horny jizzing off up a hairy arse.”

“So that’s what Eddie Poulton does to Simon Rowley?”

“More like Rowley does it to Poulton,” he said.  “I reckon for those pair it’d have to be that way round.”

“Why would it be that way round?”

“Poulton’s more like a girl.  The girl one lets the boy one seed him up the shitter.”

That seemed reasonable.  Rowley was quite sporty – he was bowling right now – whereas Poulton was more of a ‘sensitive sort’ as teachers would call it.

“So why’s it called brown-dicking?” I asked.  I could be so dozy sometimes.

“Come on, dipstick, have a little think about it,” Hudson grinned. “Rowley’s dick slides up Poulton’s bumhole… and when it comes out…”

The penny dropped, and my face contorted into a wincing ‘ugh’.

I had so many more questions but I didn’t want to ask too many in case Hudson thought I was interested in doing some brown-dicking of my own.

And I wasn’t – really I wasn’t!  I was intrigued by the concept that some boys used their friends’ bums to jizz off up but I certainly wasn’t desperate enough to consider using such an unappealing orifice myself.

A few months later I was sitting on the loo having been excused from an RE lesson when I noticed, among all the other graffiti on the back of the door, that someone had scrawled ‘Daniel Parker bummed Lee Murray on the hiking trip’.  And there, below the assertion, was a crude drawing of the two boys en flagrante.

If I hadn’t had the chat with Stephen Hudson at the cricket match, I probably would have been completely oblivious to the message that was being conveyed.  First of all there was the word ‘bummed’ – was that the same as brown-dicking?  And then there was the drawing – was that how two boys would have sex together?

When Hudson had described gay sex, I’d assumed that the two boys would do it much the same way that a boy and girl would and in my mind that meant that face-to-face.  I’d imagined Eddie Poulton lying on his back with his legs wide open the way we drew lewd cartoons of girls in the back of our jotters, and Simon Rowley getting on top of him so that their chests were pressing together.

Now that I could see how Daniel Parker had supposedly ‘bummed’ Lee Murray during the trip to the Pyrenees, I figured that pairs of boys must have sex together in a different way to the way that I’d grown up thinking that boys and girls do it.  Boys – it seemed – did it from behind.

One boy, the ‘girl one’ as Hudson had described him, bent over on all-fours and pushed his arse right back.  The ‘boy one’ knelt upright behind his friend, holding onto him by the hips, and then I guessed there’d be a fair amount of thrusting and grunting before a sticky deposit was made up the splayed-open backside of the guy out front.

I wondered what would happen then – how would the boy who’d just let his friend jizz off up his arse get to fire off a decent load of his own.  From what Hudson had said it wasn’t just a matter of changing places, so perhaps it was usual for bummer to suck off the bummee straight afterwards as a way of saying a polite ‘thank you’.

It was curiously fascinating to find out how it worked when it was two boys having sex but, again, I wasn’t in any way sexually excited by the idea. Which is why what went on between me and Adrian Stanton for the best part of a year might come as something of a surprise.

It must have been the September we’d both started in the upper sixth and finally we had our own single rooms with lockable doors.  Stanton and I were in his room after supper one evening – still basking in all our new perks and privileges – and we got chatting about how we’d dodged all the many ‘Rules of Masturbation’ since we’d started at the school.

I told him how my dorm had always been jerk-off central after lights-out in spite of rule number one, and he told me how he’d flouted rule number four by wanking off into a hollowed-out pumpkin.

We’d had a great time swapping stories and describing our various near-misses, and then Stanton asked if I’d ever broken the last dictum on the list, the oddly-worded rule number eight.

“That stuff about annual masturbation?” I asked.  “I could never really work that one out.”

“It’s not annual masturbation, you wally,” he chortled.  “It’s anal masturbation.  It’s about wanking yourself off using your arse.”

“How are you supposed to do that?”

“You push stuff up it.  There’s a G-spot up there… a sort of nerve bundle or something… and it feels really good when you rub stuff up and down against it.”

I was feeling a bit confused.  “What’s a G-spot when it’s at home?”

“You know how when you rub your dick up and down it feels dead nice?”

I smiled and nodded.  I knew that very well.

“Well it’s the same with some weird nerve thing you’ve got up your arse,” he went on.  “When you rub it up and down, it makes you feel all tingly and sexy!”

Now you might be wondering why I didn’t link all this talk about bums being erogenous with the stuff that Hudson had told me and what I’d seen on the back of the toilet door.  But in my mind that earlier stuff had been about boys cumming up other boy’s arses; what Stanton was on about was to do with wanking yourself off using some special nerve thing up in your rectum. I’ll maintain until the day I die that to me the two things had seemed like they were worlds apart and indeed it had taken until the following May – a good eight months – for me to spot the connection.

Call me stupid if you like.  You’d probably have a point.

But in fairness to me, there’d been like two years between the Hudson conversation and the chat with Stanton and loads of stuff had happened in the meanwhile so I’ll keep telling myself that the parallels weren’t exactly leaping out waving hi-viz banners.

Anyway, I asked him, “So how do you rub it up and down if it’s up your arse?”

“You push something in and out of it… like your finger or something…”

“And that’s anal masturbation?”

He nodded.  “I think so.  You have wank your dick off like you normally would for it to have an effect… but it makes it feel so much better… makes you spew off so much more powerfully.”

“How do you know all this stuff?” I asked him.

“Promise you won’t tell anyone?” he asked back.

I nodded – everyone nods when someone asks them that – and he explained how when he’d been wanking off with some third former in a toilet cubicle, the other boy had shown him how to anally masturbate.

“How did he do that?” I enquired, my eyes wide with interest.

“He pushed his finger up me,” Stanton told me with a blush.

“And did it feel dead nice?”

“I came buckets, Kason.  I swear to God, I’ve never spunked off as much as I did that night!”

“Haven’t you tried it again?” I asked him.  “Haven’t you done it on your own… with your own finger?”

“That’s the thing,” he said, “it only feels good when someone else is doing it.  When I’ve tried it on myself, it doesn’t really do much for me.”

I nodded, fascinated.  This was all making complete sense to me.  When Dominic Holden had sucked me off during breaktime, the feel of his finger on my arsehole had made my cock shoot its muck down his throat.  I’d tried doing the same thing myself – had butt-fingered myself as deep as I could next time I’d been able to wank off in private – but it didn’t feel as good as having Holden’s finger back there.

“So this anal masturbation thing,” I said, “do you think it’s something someone else has to do to you for it to work properly?”

“I reckon so, yeah,” he said.

I hesitated, not sure how to phrase what I wanted to suggest.  But then I bit the bullet and said, “Do you want to try it on me?”

I expected Stanton to laugh and say something like, “You’re not actually asking me to stick my finger up your arse?”  If he had I was going to laugh back and pretend that I’d got the wrong end of the stick.  That I’d thought he’d said something about a third former fingering him and was just playing along to be part of the joke.

I’m not totally stupid, see?

But he didn’t laugh.  He said back, “It might be a bit weird, but we could give it a go…”

And I replied, “If you do it me, I’ll do it to you.  If one of us is going to break rule number eight, might as well both be hung for it!”

He smiled and nodded.  “Pull your trousers and pants down… lean over my desk.”

I did as he’d said, showing him my bare, spotty bum and asked him, “Are you really sure you want to do this, buddy?”

“I don’t want to,” he smirked, “but if you’re offering to do me… the feel of what that third former did in the john was totally out of this world, Kason!”

I stuck my arse out for him and he licked his middle finger before using it to find my little clenched hole and inserting it slowly up into my rectum.

“It feels weird,” I told him.  “I’m not sure that I like it…”

“Has it made you hard?” he asked.  “Is your dick on full crank?”

“No… to be honest, it’s kind of withered away… I reckon it thinks this is some sort of medical exam.”

He laughed at that and then suggested, “Maybe if I work my finger in and out a bit, it’ll get you horny.”

“Is that how it worked with you?” I asked him.

“Not really,” he said, “we were already wanking off so I was horny to start with.”

“Okay, well let’s try it… this couldn’t feel anymore weird than it does already.”

He pushed his finger in and out of my bum and I asked him, “What the hell is that godawful smell?”

“Er… I’m fingering your arse, Kason… what do you think is making a stink?”

“Oh,” I said.  “Sorry about that.”

“Look, forget about the smell… how is this feeling for you?”

“Still weird,” I told him, “I can’t really get into it.”

“Well, look,” he offered, “there’s something else I could maybe try…”

“What’s that?” I asked.  “This really isn’t working.”

“When I said that third former used his finger, I wasn’t exactly telling you the whole story…”

“What did he use, then?  His thumb?”

Several boys had pushed their thumbs against my bumhole when they’d been sucking me off and it had usually brought me off.

“No,” Stanton said, “he used his dick.”

“His dick?” I asked.  Again, the cogs weren’t for turning.

“Yeah… he had quite a thick one and it felt really sexy when he slid it in and out…”

“And that’s what made you cum buckets?”

He smiled and nodded.  “You know how when you shit out a big turd, it’s a lot thicker than a finger?  I mean, mine usually is…”

“Okay…?” I faltered.  Why was he suddenly talking about shitting?

“And when it’s a really wide one… a massive log-sized shit… it feels kind of tingly when it slides out… makes your dick start twitching…”

I blushed and nodded.  Sometimes I grew a full boner from the feel of an especially thick dump pushing its way out of my arse.

He smirked and went on, “So I reckon you need a pretty thick circumference to make anal masturbation work…”

“So you want to push your dick up my chuff-hole?”

“No, I’m offering to anally masturbate you…. I just reckon it works best with something thicker than a finger.”

“I dunno, Stanton… won’t it be a bit weird…?”

“Don’t be daft!” he chuckled.  “I’m just going to wank your bum off by rubbing your G-spot with my dick… I’m not going to spunk off up your arse!”

“I dunno…” I repeated.

“We’ll give it a go… and if it doesn’t feel right, we’ll stop, okay?”

I wavered, still far from convinced.

“Come on, we’ve trashed every other rule in the hand-book,” he laughed. “Might as well break rule number eight!”

I smiled.  “Okay… but just stick it in and I’ll see what it feels like…”

I turned around again and he hitched his trousers and underpants down a bit.  Nothing happened so I glanced over my shoulder to see him frantically wanking his knob off to get it hard.  It reminded me of a school trip to the zoo I’d once gone on, when I’d seen a monkey hunched like he was, jerking its little dick off.

“That’s about got it,” he said after about a minute of vigorous masturbation.  He snorted up a thick wad of mucus and gobbed it down onto his semi-hard prick.  He smeared it all over the head and shaft, getting it slippery enough, and then shuffled up behind me to try and push it up my arse.

“Is this going to hurt?” I asked, feeling his slimy bell-end against my pucker.

“Of course it won’t,” he assured me.  “I bet you’ve shat out big thick turds that were fatter than my dick!”

He was right on that score, so maybe this wouldn’t be as bad as I feared.

I leaned forwards, supporting myself against the top of his desk, and he slid his cock slowly up my bum.  To my amazement, it felt extremely nice and I felt my own dick start to stiffen and lengthen as his pushed against the squeeze of my butt muscles.

“God, I’m getting hard!” I gasped.

He chuckled into the back of my ear.  “I told you it felt dead sexy!”

Once his cock was right up me and I could feel his hairy bollocks tickling the backs of my legs, he eased it slowly out again and then started working it back and forth.

My cock rapidly swelled bigger and rose upwards between my legs, like a sausage-shaped balloon being quickly inflated.  I wrapped my fingers around it and started jerking myself off, loving the sensation of having a thick tube sliding up and down inside me.

“How’s it feel to be anally masturbated, Kason?” he asked with an audible leer.

“Bloody amazing,” I panted, pushing my arse back against his thrusts. “That G-spot thing’s making my nuts really tingle!”

He laughed and really went for it inside me, ramming his cock against whatever nerve bundle was up my backside and making me shudder and whimper until within seconds I was flinging spunk all over his desk.

“Oh Jesus – that’s my Chemistry homework, you plonker!” he laughed, still sliding his dick in and out as mine emptied itself all over his papers.

“Sorry,” I managed to grunt, seeing stars from how my orgasm had been so intense.  Then I fell forward onto his desk, feeling like I was going to faint, as his cock slid out of me with a loud sloppy fart.

When I’d eventually recovered – I actually thought I was going to have to ask him to fetch me a glass of water – we hitched our trousers back up and opened his window to get rid of the strong shitty smell.

We sat on his bed and he smiled at how red my face was.

I said, “That was totally out of this world!  I can see why they’d make a rule about it… they hate us having fun!”

“You have so got to do me!” he chuckled.

“There’s no way my dick’s going to be good for anything tonight!”

“Yeah, it’s a bit annoying we can’t go one after the other… but maybe next time, you can do me?”

“Of course, bud!  We could take it in turns…”

And that’s what we did for the next eight months: one night Stanton would anally masturbate me, the next we’d swap places and I would use my dick to wank off the G-spot up his bum.

I didn’t really like doing it to him if I’m honest.  His arse stunk really nasty and I would end up with his slimy crud under my foreskin.  But having his dick up me more than made up for such unpleasantness and some nights I’d be crying out in ecstasy at the feel of the ridge on his cock head working back and forth up inside my bum tunnel.

I think that’s why I never associated what Stanton and I were doing with the way that Rowley and Poulton were having sex together.  Everyone whispered about those pair being ‘bum-chums’ and if Rowley’s door was ever locked boys would snigger that he was in there doing Poulton up the arse, but as strange as it may seem, I saw no connection between any of that and the fact that Adrian Stanton and I were wanking off with each other’s dicks sliding in and out of each other.

Perhaps it was because we always called the fun we were having ‘anal masturbation’ or ‘doing a rule number eight’.  Or more likely it was because our pleasure was borne from having an orgasm with something lodged up our backsides – neither of us ever climaxed with our dicks up inside the other.  Stephen Hudson had described gay sex as one boy ‘sperming off’ up another boy’s bum and I think that definition had engrained itself into my brain at the exclusion of other possibilities.

So it took until the following May, after the two of us had been going at it almost nightly, for the truth to finally hit home that we doing something more significant than just wanking each other’s bums off.

It was the night before half term and most of the boarding house was empty. All the younger boys had already been collected by parents and there were just a scattering of sixth formers hanging around to catch the early train the following morning.  On our corridor, only me and Stanton remained.  I think that’s why we were more brazen than we normally were: we did it in the nude and on his squeaky bed.

By then, we’d discovered different ways to improve our enjoyment when we did a rule number eight together.  We’d found it worked better when the one having his G-spot jabbed bent forwards to open his bum up fully, and when the one behind grabbed his partner’s hips as leverage it delivered a much deeper and more satisfying masturbatory experience.

So on this particular night, just before the summer half term break, it was my turn to have my bum wanked off.  We were both hot and sweaty, noisily going at it on Stanton’s bed, with me on all-fours and Stanton kneeling upright behind me.

I was in heaven, feeling him hold tightly onto my hips while his cock drove relentlessly in and out of my big gaping arsehole.  We’d put a towel on his bed to catch my jizz when it started spraying all over, and we writhed together on top of it, Stanton’s muscles flexing as he pounded his hips hard and fast against my buttocks.

I turned to him, grinning up at his red flushed face over my shoulder, and he smiled back down at me, loving that we could let rip like this without other boys overhearing us.

Both panting noisily, I managed to gasp, “Really give it to me… ram it really hard up my arse!”

He leered back at me and pulled my hips back towards him, slamming his manhood as roughly as he could through my big swollen hole.  Our two big pairs of nuts were swinging low underneath us and thumping into each other, and he drove his cock deeper up me than he’d ever managed before, making me squawk with delight and fart noisily around his shaft.

I was just about to grab my own dribbling erection and start jerking it in time with frantic pumping of Stanton’s, when suddenly he stopped and said: “I don’t think I locked the door!”

I laughed at that, pleased to be able to catch my breath for a few seconds before our relentless rhythm resumed, and said, “Leave it open… the housemaster might walk in on us!”

Stanton laughed back.  “I reckon he’d soon walk out again, the stink your arse is kicking out!”

I turned to smirk up at him.  Wanking another boy’s bum off with your dick was always really smelly.  It was the reason I preferred to do it in his room rather than my own.

“Even so,” I chortled, “he’ll wonder what the hell we’re doing!”

Stanton smirked broadly and said – and how I’ve wished so many times that he hadn’t – “He’ll probably think we’re bumming!”

I chuckled over my shoulder at him, might have even said something like “Don’t be stupid,” before I suddenly remembered the lewd drawing on the back of the toilet door and realised that Stanton and I were in exactly the same position as the two boys on the hiking trip.

This wasn’t just some exotic form of masturbation: this was proper gay sex and we were taking turns to bugger each other.

I pulled off him, clambered off the bed and gasped, “Bloody hell, Stanton! We are bumming… that’s exactly what we’re doing!”

He just grinned over at me, his slimy cock still arching upwards in front of his belly, and seemed to think I was joking.  “Don’t be a div, Kason! I’m just anally masturbating you!”

“Don’t call it that!” I snapped, grabbing my underpants.  “We’ve been butt-fucking each other!  That’s what it’s called!”

He swivelled around to face me, still with his cock at full mast as if hoping somehow I might get back on the bed with him, and said, “Come on, don’t be so serious… it’s not like we’re gay or anything!”

“But it’s gay sex, Stanton – we’ve been brown-dicking each other!”

“How the hell is it anything like brown-dicking?” he asked.

I looked at his cock, streaked with the gunge from my arse, and finding that it articulated everything I couldn’t, pointed an accusatory finger towards it.

He stared down at it too, throbbing upwards with the big head of it smeared in shit, and then looked back at me more serious, his cheeks colouring as scarlet as mine probably were.

We didn’t say very much to each other after that night but at the end of term, on graduation day, he split from his parents to come across to me wearing his best formal suit.

“Look, I’m sorry,” he said, and put his hand out to shake mine.  “I just didn’t think.”

I smiled at him and grabbed his hand to squeeze it, before replying, “I’m sorry too.  I guess we both got carried away.”

Sitting here in my kitchen, twenty-odd years later, I can’t understand why the realisation that Stanton and I were having gay sex had such an upsetting effect on me back then.  I guess I had very narrow views about what was sexually acceptable and what wasn’t and in my eighteen-year-old mind, what Stanton and I were doing had clearly crossed the line.

Or perhaps I realised I enjoyed it way too much!

These days, I’ve become a lot more embracing in my attitudes towards sex, and have formed the belief that that since you only get one dick in life, you might as well have as much fun as you can with it.  And if find you like jerking it off while you’re getting shagged up your bum, why not just enjoy the ride instead of beating yourself up about it?

Having reminded myself how exciting it had been at school to break all the ‘Rules of Masturbation’, I decided that now, in my forties, I’d have fun breaking them again.  And once I was through with doing that, I’d think up some new rules of masturbation all of my own, and have even more fun breaking those too.


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