Rory and Alistair 4: Young Ferguson

Rory and Alistair could never conform to boarding school life with its countless rules and regulations. Get up at seven, bed at nine-thirty. Don’t do that; don’t go there. The two eighteen-year-olds were more suited to the life of the boys in town.

They were oddities at the school. They were both in their final year at the school, but had never received any privileges. Although they were old enough to be in the sixth-form, they were treated by everyone, masters and fellow pupils alike, as juniors.

They were even required to dress like juniors. Only boys in the sixth-form were permitted to wear long trousers: it was seen as a badge of privilege. The two boys remained in short trousers and would do so until the day they left school.

They had one other characteristic that distinguished them: they were madly in lust with one another.

Previously in Rory and Alistair

Episode one

Episode two

Episode three

 Rory lay stark naked on his bed; his stiff cock in his fist. It was another scorching day. The heatwave was breaking all records. The weight of his body pressed his corrugated buttocks into the mattress. Six ugly red welts stood up on his otherwise creamy-white bum. Two were still very tender when he put any pressure on them.

It had been Six. Short trousers at the floor, white underpants at the knees. The eighteen-year-old had been bent over a hard wooden chair; palms down on the shiny seat. The new master Mr Macaulay was showing off. He was showing Rory and the other boys at Willadong Academy that he could. If he wanted to he could put a heavy whippy rattan cane across their bare arses and there was nothing – absolutely zilch – they could do about it. Such was the power of a schoolmaster.

Rory was no fool. He saw right through Mr Macaulay. The young master had said Rory was cheeky, insubordinate, rebellious, defiant and “sassy” – whatever that meant. It was as if Mr Macaulay had swallowed Roget’s Thesaurus. Mr Macaulay had made most of it up. He often didn’t obey the rules, it was true, but Rory had done nothing special to upset Mr Macaulay.

So six-of-the-best it had been. The young master was a fine cricketer. He knew how to slog a ball to the boundary. He used that strength to whip his cane into Rory’s bared bottom so fiercely it was as if he were trying to enter at one end of the buttocks and slice through them like a hot knife and butter, before exiting at the front. It had been one heck of a thrashing.

Mr Macaulay enjoyed every moment of it, Rory was quite certain of that. The master was probably at that very moment lying on his own bed wanking himself dry at the memory. Rory himself was close to orgasm. He wasn’t thinking of his caning, he had other pleasures on his mind. In a perfect world he would be fantasying about his boyfriend Alistair; the two eighteen year olds shared the same room and had sex at least once every day. But, despite Rory’s great affection for Alistair he never used his friend as wanking material.

Rory didn’t know the name of the star of his dream. It was a guy he had seen at Banjo’s record shop. Banjo’s was the closest the town of Willadong had to a “counter-culture” – it was where the young people – and some not so young – went to hang out and listen to the latest records from America. Recently they had spent a lot of time listening to some new guy called improbably Little Richard.

The young man Rory dreamed of always looked so sad; he had a permanent frown painted on his face. But his legs and oh that cute little bum encased in the tiniest pale green cotton shorts. How Rory would like to get inside those. Whoosh! He shot a load over his belly.

Only later as he cleaned himself up with a rag did he notice the time. It was past lock-up; where was his friend Alistair? Had something happened to him?

At that moment Alistair was trudging his way back to the school. His backside throbbed. The short trousers he was forced to wear as a “junior” boy chaffed against his raw buttocks. He was late for lock-up; the chances were he’d get a sound spanking from Pendleton, the Head of Wilson’s House. It wouldn’t be the first time he was forced to bend across the house captain’s knee for a dose of his hard wooden hairbrush across the bare arse. Pendleton wouldn’t care that Alistair’s bum was already on fire.

The eighteen-year-old grinned. What an afternoon it had been. Who would ever have predicted it? It had happened in Ferguson’s bottle shop. Old man Ferguson was typical of small shopkeepers – he had very few scruples. If a boy had cash, he would sell him liquor. No awkward questions about age were asked. Not all the seniors at Willadong Academy were angels. Many of them frequented Ferguson’s. Even Rory and Alistair – short trousers or no – were served there. So, that afternoon Alistair made his regular visit in search of a quarter bottle of whisky.

But the old man was not there. Instead, a younger version stood behind the counter. Alistair had never seen him before, but it didn’t take a genius to see he was Ferguson’s son – or, for he couldn’t have been older than about twenty, his grandson.

“Bells, please,” Alistair did not anticipate trouble; he was a cash-paying customer. He might not have expected trouble, but trouble he most certainly got. “You must be joking,” Young Ferguson rejoined, and then he positively sneered the next word, “sonny.”

Undeterred, Alistair repeated his liquor order. “Quarter bottle. Thanks.”

Young Ferguson looked Alistair up and down. From his thong encased feet to the top of his tousled hair. He saw an obvious schoolboy, dressed only in grey short trousers and an open-necked white shirt.

“I know you,” Young Ferguson leaned forward across the counter menacingly. “You’re from the Academy.” Alistair flushed. This wasn’t going to plan. “I’m getting on the phone right now. I’m calling your headmaster.”

The eighteen-year-old reeled. Headmaster! The stupid man meant it too. “B.. b.. but,” he blustered. “Yeah,” young Ferguson grinned. “It’ll be a right caning for you. Bare arsed, I shouldn’t wonder.” He was enjoying himself enormously.

A caning. Yes, Alistair thought, almost certainly. But there could be much worse to come, if the headmaster heard about his regular visits to the bottle shop. Alistair had been in so much trouble at school over the years, this might be the straw that breaks the camel’s back. This might be the time Dr Bruce, the headmaster, sent him packing. Expelled. Sent home in disgrace. No school examinations sat. No place at university. No good career to look forward to. All because of this idiot shopkeeper’s son.

Young Ferguson peered perceptively at the schoolboy standing before him. No boy wanted a flogging from the headmaster. He would do almost anything to avoid that. Young Ferguson had learnt as much in the weeks he had been standing in for his father.

“Of course,” he stretched his arms wide and then steepled his fingers, “I could deal with the matter myself.” He left the words hanging in the air. The silence in the small shop was deafening. Young Ferguson let the words sink in. He assumed Alistair was no fool. They were supposed to be a brainy bunch at Willadong Academy.

“Well?” Young Ferguson’s tongue shot out his mouth like a lizard’s. Then he ran the tip around both his lips, all the time staring intently at the youth in front of him. “What’s it to be? Me or the headmaster?”

Alistair couldn’t stop is eyelids blinking. What kind of choice was this? It had to be either a flogging and possible expulsion at the hands of Dr Bruce or some as yet unspecified treatment from the vile Young Ferguson. The heat in the small shop was oppressive; sweat poured down Alistair’s back. He could hardly breathe. Any moment now he might collapse on the floor in a faint.

His mouth was impossibly dry. There was not a single drop of saliva. Alistair could barely form the words he needed to say. “You,” was all he could croak.

“Is the right answer,” Young Ferguson shouted over-enthusiastically, like a game show host on the radio. He sprang towards the shop door, locked it and turned the “Open” sign at the window to face the other way.

“Follow me,” he said as he breezed through the shop and entered a storeroom.  Miserably, Alistair followed behind. He stopped at the entrance of the room, astounded at what he saw. It was in most ways a typical storeroom for a small shop. There were some cases of booze and others with cigarettes. But dominating the room, right in the centre, were two crates stacked one on top of the other. And on the top of that was an old grey blanket. It was neatly rolled and laid out to make a cushion. It was a makeshift punishment block. It was the right height for a boy of Alistair’s size to bend across and offer up his backside for beating.

On the far wall, hanging from a large nail was a dark brown paddle. Alistair had never seen one before. Willadong Academy was a “caning school” – although some heads of house used a rubber-soled gym shoe. And, Pendleton, of course used his nanny’s hairbrush. This paddle was twenty inches long, about three-quarters of an inch thick and four inches wide. It had holes drilled in the blade end.

used paddle holes (5)

“Oh I see you’ve seen the paddle. It’s a real beauty, I can tell you.” Young Ferguson spoke as if he were showing his prisoner his new car. “Very effective. Stings like hell,” he grinned. “As you are about to find out.”

Alistair blanched. Even his deeply suntanned face could not disguise his concern.

“Yes,” Young Ferguson positively beamed, “I’ve taken the arses off a few of your school chums.” He swirled the words “school chums” around his mouth as if enjoying a fine wine. “You won’t sit down for a week,” he chuckled to himself. “Come on in, don’t stand at the door. I haven’t got all day. I’ve had to lock up the shop.”

Alistair shuffled forward. He was no stranger to corporal punishment. Sometimes it seemed his arse was permanently bruised. Just as the effects of one caning were wearing off; he was bent across a chair for another bowing. Such was his life at Willadong Academy.

“Come now,” Young Ferguson was enjoying himself immensely. “Stand by the block,” he said as he reached up to the wall and retrieved the paddle. It looked an awesome weapon in his small hands. He held it by the handle in his right fist and gently tap, tap, tapped it into the palm of his left hand. Alistair’s eyes followed it as it moved.

“C’mon, let’s have those trousers down. Pants too.”

Alistair couldn’t believe it. What would he tell Rory? That he tried to buy whisky as usual, but instead of old man Ferguson, he found his pervert son. And said perve demanded Alistair show him his bare arse so he could whack it black and blue with a heavy wooden paddle. Rory would never believe him. Until, he showed him the battered backside and the outline of the paddle reproduced dozens of times across his cheeks.

“Come on!” Young Ferguson raised his voice considerably. “Do you want me to come over there and take them down for you?” He would do. He had done precisely that with one lanky prefect only yesterday. The stupid boy had frozen to the spot with both terror and humiliation. He had howled the house down after only a couple of swats.

Alistair shot Young Ferguson a glance. It was one, he hoped, that showed his contempt for the pervert, tinged with just a little defiance.

“Watch your attitude, sonny,” Young Ferguson sneered. “Just remember I’m the one with the paddle in his hand and you’re the one about to show me your bare arse.”

Alistair, undid the button at the top of his short trousers. They had a half-elasticated waist so needed no belt. The shorts slipped down his thighs and gravity took them past his knees and to the floor. Young Ferguson gazed at the eighteen-year-old’s underpants. Alistair’s cock was not erect, but it still made a terrific bulge against the snug cotton.

He hitched his thumbs under the waistband and sent them to meet his short trousers in the puddle at his feet.

“Bend over.”

Alistair slipped his feet out of his thongs and stepped out of his shorts and pants. He was naked from the waist down. The top four buttons of his white short-sleeved shirt were unbuttoned, revealing his clearly-defined chest. It was as nut brown as the teenager’s face. He moved forward a couple of paces and positioned himself over the block. He had to stand on tiptoe so the palms of his hands could rest on the cold stone floor. His naked and vulnerable buttocks rested along the edge of the chest at a perfect angle to receive swats from the paddle.

It wasn’t necessary, because Alistair’s shirt tail had risen up his back, but Young Ferguson took hold of it and dragged it so that the shirt was now at the teenager’s shoulders. He was almost totally naked. Alistair was deeply suntanned across his whole body, except for a small area where swimming trunks had covered his buttocks, which was creamy-white. Ferguson ran his hand over Alistair’s cheeks, making gentle circular motions across the apex of each mound. The cheeks were tighter than some Young Ferguson had encountered in the past few days.

At last, he was ready to go. He lay the paddle across Alistair’s left cheek, raised it about two feet away from the flesh and brought it crashing down. It was all in the wrist action. Young Ferguson admired the red rectangle that instantly appeared. Alistair’s mouth opened and his lips formed an “owww,” but he uttered no sound.

By the fourth whack of the paddle, Alistair was starting to feel it. His bottom tingled. As the fifth and sixth blows landed he was surprised to find that the paddling was really hurting. The heat built into a terrific ache and each stinging new blow inflicted fresh torment. Involuntarily, his bottom wriggled and quivered.

Young Ferguson nailed Alistair’s bottom from one side to the other, up and down and down and up, taking the paddle under his cheeks and onto his thighs. That burned like the fires of hell. Young Ferguson whacked at ten second intervals. Suddenly, he stopped. Alistair lay across the chest unsure what to do next. At school the master would give a command. “Up,” or would say something like, “That’s it. It’s over,” but Young Ferguson remained silent. Then, Alistair felt his punisher’s hand caressing his backside. It reignited the pain in parts of his throbbing bum. Welts had risen and blood was trying to weep through where the paddle had repeatedly landed on the same spot.

At last Young Ferguson spoke; or rather, he croaked, “Okay. You’d better stand up.” Alistair hauled himself to a standing position. His bum ached like crazy. It had probably been one of the worst beatings he had ever endured. It had gone on and one. This had been no simple six-of-the-best. Six severe cuts and it was over. He hadn’t been counting, but he wouldn’t be surprised if the pervert had given him a hundred or more swats.

He retrieved his trousers and pants and very gingerly he dressed. Young Ferguson stood and watched him do it. He was wheezing, his body bent double. Alistair tried to see the front of his tormentor’s trousers, but Young Ferguson kept it hidden.

Without a word, Alistair left the storeroom. He knew Young Ferguson would not follow him. He wouldn’t return to the shop until he had masturbated. Alistair went behind the shop counter, found two quarter bottles of whisky and slid them into the pockets of his short trousers. He unlocked the door and left it wide open as he hurried down the street in the direction of school.

The prefects had given up waiting for latecomers. It was a lucky break. Alistair would not have been able to endure another spanking. He returned to his room to find his lover Rory naked on the bed, the cuts across his backside still raw.

“Macaulay,” he said in answer to a question Alistair had not asked. He rolled onto his stomach so his pal could have a better view. Alistair licked a finger and traced it across the six welts. “Pretty impressive,” he said cheerfully. “But, not a patch on this.”

He grinned hugely as he whipped down his short trousers and underpants to show Rory his savaged arse. His efforts were greeted by Rory’s swelling cock. Alistair’s dick saluted in solidarity. “I’ll tell you about it later,” he wheezed as he knelt by the side of the bed and put his lips around the tip of Rory’s magnificent spear.

Other stories you might like

The Gaffer of the Academy: 1. Beginnings

The Spanking Vicar Part 1

The Tyrant Headmaster Episode 1


More stories from Charles Hamilton II are on the MMSA website


Charles Hamilton the Second

Mr Hennessey’s Boys 4. Timothy’s story

used master

Previously in Mr Hennessey’s Boys

Episode 1, Howard’s story

Episode 2, Noah’s story

Episode 3, Ethan’s story



Mr Hennessey has a stable of young men who for a price are willing to offer their backsides to corporal punishment enthusiasts. Here, Timothy goes back to the classroom …


“Boys like you need to be punished or you’ll never learn. Stand up Kennedy. This will be a lesson you’ll never forget.”

Mr Higgins waved his cane threateningly at me, almost in my face.

I scrapped back my chair and rose from my school desk and prepared for the order, “Bend over and touch your toes.”

I was in an actual classroom and Mr Higgins was a genuine schoolmaster and I’m pretty darn certain ‘Kennedy’ was a real schoolboy too.

Mr Higgins had put me in the detention class at [name redacted] an actual boarding school. The real pupils were on holiday and we seemed to have the building to ourselves. Higgins was a schoolmaster at the school. Either that or this was the most spectacularly blatant guerrilla movement ever. A stranger just moved into the classroom as if he had every legitimate right to be there.

I think Higgins had a beef against three pupils in particular. Maybe they gave him a hard time in his classroom and he couldn’t do a thing about it: corporal punishment having been abolished.

That evening I kicked off as ‘Turner’, found guilty of cheating in his history class test.

“Turner you will write out fifty times in your neatest handwriting, ‘I must not copy out the work of other boys in a test and then pass it off as my own.’”

It was incredibly tiring and by the end my wrist was as sore as it’s ever been; even after one of my marathon wanking sessions.

The classroom was a mixture of the old and the new. The lighting and air conditioning was definitely of ‘today’, but the school desks were from a time long gone by; those individual ones they had that opened from the front and had a hinge. As I was soon to discover the slope from the back to the front made an ideal platform for a schoolboy to bend across and offer his bum up for the kiss of the cane. Kiss? Who am I kidding? The SWOOSH! THWACK! OUCH!! of the cane I mean.

I was wearing an authentic blazer from the school, a rather natty royal blue number with yellow braiding. I rather admired it to be honest.

Mr Higgins had a traditional academic gown and again I’m pretty certain that it was the authentic one he probably wore in his daily life. The whippy rattan cane he was brandishing was the real deal too (I can give personal testimony to that), but I suspect it had to be taken out of mothballs for that evening, since caning in schools had been abolished a generation ago.

He looked through my lines and was dissatisfied.  “Pah! You call this neat handwriting, Turner?”

“Stand up and bring your chair with you.”

He took my straight backed wooden chair and put it against the back of another.

I climbed on one chair and bent over the combined backs and placed my hands palms down on the seat of the other. I’d never seen this position before, but it turned out it was all the fashion eighty or more years ago. It certainly placed my bum at the perfect angle for him to slash his cane into the seat of my trousers. Which he then proceeded to do.

They were six real stingers and I could feel the cane had made welts across my buttocks, but I’m pretty resilient and took it like a champion.

“Stand in the corner, Turner. Hands on head.”

That was end of part one.

There was no commercial break; I was just left standing, until Mr Higgins rearranged the furniture.

“Probert,” he called to me. “Sit in that desk.”

He then gave me a stern lecture about my misbehaviour in the history lesson. I was always playing the class fool.

“Take fifty lines. ‘I must always remember that nobody in the class is the least bit interested in my attempts at comedy.’”

It took me nearly an hour and by the end I was ready to soak my wrist in a bowl of cold water. Soon I’d be happy to bathe my arse there as well.

“Probert, you think you can make a fool of me, but you can’t. I am going to demonstrate that now. I am going to beat you like you have never been beaten before.” He said it with such conviction, I really felt sorry for the real Probert, whoever he was.

“Take down your trousers and bend over the desk.”

I hesitated. I figured that was expected of me. Trousers down? We were moving away from reality, here.

“Now, Probert. Do as you are told or I’ll double the number of strokes.”

I stood in front of the desk, let my trousers fall and leant across the desk. The sloping lid made a wonderful platform, presenting my bum as the highest part of my body. Mr Higgins pulled the waistband of my white underpants tight. I winced as the cotton rubbed against the raw welts left on my buttocks, courtesy of Turner.

He laid six strokes into me, at intervals of thirty seconds. I couldn’t see his face, but I knew he was relishing every cut of it. It genuinely hurt and by slash number four I was groaning, but I kept in position.

He left me hanging over the desk for what seemed like an age, while he admired my tight buttocks. I don’t know what was going through his mind; was he lusting after the genuine Probert, or me? To be honest, I’d rather not know; sometimes with the gentlemen it’s best not to.

After a session in the corner, Probert morphed into Kennedy. I never had the opportunity to meet the boy, but I rather wish I had. He must have really pissed Higgins off. The lecture went on for ever; his rudeness, insolence, impudence and disrespect of authority. Yep, Kennedy did not like Mr Higgins. I wonder what he would think about this crazy game being played out in his name?

We didn’t do lines this time but went straight to the action. “Stand up Kennedy. This will be a lesson you’ll never forget.”

I walked as instructed to the front of the room. “Boys,” Mr Higgins intoned to an imaginary class, “I want you all to witness this. I will not tolerate insolence and any one of you who has the audacity to take me on, will befall a similar fate.”

There was a glassy faraway look in his eye as he swished the cane through the air. I think he was beginning to lose it.

“Trousers and pants down, Kennedy. Bend over and touch your toes.”

As anyone who has ever heard that dreaded command knows, the bending over and touching toes isn’t the hard part. The hard part is staying down after the slash of the rattan has taken half your arse off. If you are bending over a chair or a desk, you have something to grab hold onto for dear life. But, when you are touching your toes, you are on your own.

My bum was still throbbing and quite scarred from my previous two canings, so when Mr Higgins flogged the first cut, and I do mean ‘flogged’ it into my bare buttocks, I yelped like a dog and shot up to clutch at my roasting cheeks.

“Over Kennedy. Don’t be a coward. Take it like a man,” he stressed the word “coward” in a way that sent a shiver down my spine. This guy truly hated Kennedy and wanted the real boy to be there that evening, but that was impossible, so I was to be his whipping boy instead.

I bent down again, grabbing hold of the trousers that were crumbled at my ankles. Slash two whipped against my arse, it came with such force I’m sure he was trying to cut my body in two.

Number three was worse. I was howling like a wolf. If there had been anyone else in the building surely they would be running to the classroom to see who had been killed.

Was Mr Higgins still in control of himself? How could I be sure? I had never called off a session mid-way, but that evening I came pretty close.

I took the full six and was in some distress; so, it seemed, was Mr Higgins. His breathing was erratic and his eyes were rolling in the back of his head. I’d never seen anything like it before or since. Was he in ecstasy? Like those religious fellers who speak in tongues?

In extreme agony, I dressed myself and waited for him to come back to planet Earth, but he was in lunar orbit and wouldn’t be coming home for a long time yet. I felt the used bank notes in my pocket and realised there was nothing to keep me there. I collected my bag and left, still wearing the rather nice royal blue blazer.

My backside was twice its natural size and when I admired it in the mirror at home, there were eighteen very distinct welts; six of them were as thick as my finger. It wasn’t too bloody and after I gently massaged ointment into the wounds the agony slowly turned to a glowing throbbing.

It is a cliché of spanking stories that the punished boy is in so much pain that he has to sleep on his stomach at night and he can’t bear being touched by his bed clothes. It isn’t like that in real life in my experience, but that night for me it came mighty close.

That night I couldn’t sleep too well, not because of the pain in my buttocks, real though that was. I was tossing and turning trying to work out Mr Higgins. I was certain he really was a schoolmaster at that boarding school and Turner, Probert and Kennedy were real boys, either his current pupils or from his past. Had his session with me been some kind of exorcism for him?

I was intrigued by the man and I longed for him to contact me for another session. Months passed, the memory faded and I had to accept that I would never meet the man again.

Then, one summer’s day I got a call from my agent Hennessy. Mr Higgins asked did I mind letting him teach a friend the art of caning using my backside as his prop.

The man is bonkers, absolutely bonkers. I told Hennessey, Yes, I replied and arranged to meet Mr Higgins at his apartment.

But that’s another story.


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Trouble at the mall

The Gafffer of The Academy 2. In the chill of the night

The coach and the schoolmaster



Charles Hamilton the Second


Rory and Alistair Ep 3. The Headmaster

Rory and Alistair could never conform to boarding school life with its countless rules and regulations. Get up at seven, bed at nine-thirty. Don’t do that; don’t go there. The two eighteen-year-olds were more suited to the life of the boys in town.

They were oddities at the school. They were both in their final year at the school, but had never received any privileges. Although they were old enough to be in the sixth-form, they were treated by everyone, masters and fellow pupils alike, as juniors.

They were even required to dress like juniors. Only boys in the sixth-form were permitted to wear long trousers: it was seen as a badge of privilege. The two boys remained in short trousers and would do so until the day they left school.

They had one other characteristic that distinguished them: they were madly in lust with one another.

Episode 1 is here. Episode 2 is here


Rory and Alistair were late for roll call. A buttock blistering was almost inevitable. The only chance they had was if Anderson was on duty.

Anderson was one of the laziest prefects at Willadong Academy. He wouldn’t be bothered to chase around after them.

It was another scorching day. The heatwave was breaking all records. The boys had been to the town. It was their only escape from the dreary conformity of the school. They were eighteen years old, but were not considered “senior boys.” They had no sixth-form privileges and would never become prefects. They were too unconventional for a place like Willadong.

They had spent the afternoon at Banjo’s. Banjo’s was a music shop. No, it was more than that. It was an unofficial social centre; a lifeline for many of the youngsters in town. It wasn’t exactly out of bounds to the Academy boys. It didn’t have to be. The boys were so conditioned and so “snobbish” they wouldn’t have been seen dead at Banjo’s. It was a place for the townie oiks to go, not the sons of minor aristocracy and the professional classes.

Rory and Alistair loved Banjo’s. They stood out like sore thumbs. But, the boys and girls didn’t care about social status: as long as you “dug” the music. And Rory and Alistair did. They and a gang of teen-aged youngsters had spent the afternoon jiving to the latest imported records from America.

Now, drenched in sweat from head to toes, they slowly made their way home. As “juniors” at the school they were forced to wear short trousers as part of the school uniform. Only the most senior boys, the prefects, were allowed long trousers. Who cared? That was what Rory and Alistair thought. The heat was so oppressive who would want to wear heavy flannel bags?

They carried their white school shirts and had abandoned their long knee socks. Apart from the short trousers and the flip-flop thongs on their feet they were as good as naked. Rory and Alistair were athletes. They were mainstays of the cricket team and both were strong swimmers. Rory’s strapping chest was well-defined, betraying his developed upper-body strength. His legs were strong and they went all the way up to his muscular buttocks.

Alistair loved Rory’s body. He couldn’t get enough of it. At night he would sometimes sleep with his pal in his arms. Rory loved the attention, especially when Alistair would hawk great gobs of spit into his hand and work it up and down Rory’s shaft.

The two boys sauntered down the country road, arms across each other’s shoulders. They were nearly at the school. Soon they would know what fate awaited them.

Anderson wasn’t on duty. It was MacDougal. MacDougal was ambitious. He had an eye on the school captain’s badge next year. He wasn’t about to let anyone off roll call.

Much as he would have loved to put a cane across both their backsides, he wasn’t permitted to do so. It was a pity, MacDougal thought. It was high time the pair learnt they were part of the school. The rules applied to everyone, even them.

MacDougal was brightened by a piece of news he had. “Dr Bruce wants to see you,” he smiled wickedly. “In his study.” And for emphasis, he added, “Now.”

It could mean only one thing. Dr Bruce was the school’s headmaster. He rarely had much dealing with the boys; outside of the Latin classes he taught the seniors. A summons to the study could mean only one thing to a boy: a sound flogging was imminent.

Even Rory and Alistair had never had the privilege of receiving a headmaster’s beating. It seemed that was about to change. But why now? The boys discussed it as they trudged miserably through School Hall and up the stone stairs to the headmaster’s study.

“It can’t be about roll call,” Alistair frowned. Rory loved it when Alistair frowned. He had such a beautiful open face and when he was baffled, as now, he looked so vulnerable. If they were back in the privacy of their room he would have smothered his pal with kisses.

“No,” Rory agreed. “He wouldn’t be bothered about that. It’s beneath his dignity …”

The boys giggled. Dr Bruce was a pompous, vain man. No, he wouldn’t sully his hands with everyday disciplinary matters. The boys must have committed an almighty crime.

They reached the heavy oak door of the headmaster’s study. Suddenly, the enormity of their plight hit them. What ordeal awaited them on the other side of this door? They halted, neither of them wanted to knock.

“You do it,” Rory whispered.

“No, you,” Alistair’s dreamy brown eyes sparkled. He was in a playful mood.


“No, you.”

Knock, knock. Alistair’s grin was huge. His teeth sparkled. What if they were about to suffer a headmaster’s flogging. Who cared? They would go through the ordeal together. Brothers in arms.

“Enter!” The call from within the study was distinct. Rory turned the handle and opened the door.

It was a vast room. Despite the constant sunshine that shone in the world outside the study window, it was gloomy with dark oak bookshelves around three walls. A large desk, also made from oak, dominated the room and there were a number of small wooden chairs.

Two ancient horsehair armchairs were arranged around a small table. In the corner was a tall, thin, cupboard.

The study, indeed the entire school, was modelled on an ancient English public school. Such schools still existed, but Willadong seemed to be stuck in aspic; at around the year 1908.

Dr Bruce sat behind his desk dressed in a heavy three-piece suit. Perspiration ran from his hair and down the back of his neck. Usually, he wore a traditional academic gown and mortar-board cap, but even Dr Bruce had felt the need to abandon these garments to the heat.

Like so many boarding-school masters, he was of indeterminate age. His hair was grey and his face lined. The boys under his charge assumed he could easily have been seventy years old. Certainly, his attitude to the world around him was that of a very old man.

Dr Bruce had all the life experiences of a man who had lived in boarding schools his whole career. That didn’t deter him. He had the arrogance of a headmaster; of one who must be obeyed, by pupils and masters alike. His word was law. He was always right; even when so obviously he was not.

Rory and Alistair stood in front of the headmaster’s desk. Neither had yet guessed the purpose of their visit. One thing was certain to them. Whatever it was they had done, they would be leaving the study with very sore backsides indeed.

Dr Bruce sighed. It was as if he was personally carrying the troubles of the whole world on his shoulders.

“I have heard many things about you boys,” his clipped delivery was overly dramatic. Like headmasters throughout the ages and the whole world over, he was a bit of a ham.

Rory and Alistair stared down at their feet. What had he heard? Which of their numerous misdeeds had been brought to his attention?

“Many things,” he repeated himself. Then he paused for dramatic effect. “Disturbing things.”

He grimaced. “What do you have to say to that, eh, what?”

An uneasy silence pervaded the study, punctuated only by the heavy wheezing of the headmaster. He had the cough associated with a heavy smoker. At that moment he might have killed for a cigarette. And for a large glass of whisky.

“Look at me. Speak up, what do you have to say?”

Neither boy had the least idea what the headmaster meant.

Rory shrugged his shoulders. Alistair bit his bottom lip.

“How long have you been acting on these feelings?”

Alistair’s right eyebrow shot up, quizzically.

“Your friendship,” the headmaster coughed, “How long has it been going on?”

Rory stared at a spot on the window, behind the headmaster’s right shoulder. He couldn’t dare meet the old man’s eye.

Friendship? Rory pondered silently. How much did he know? But, he wasn’t about to ask him.

Headmasters, rather like the clergy, are among the most self-satisfied men on Earth. Dr Bruce had made his mind up. He was convinced he understood the situation perfectly. There could be no room for dispute.

He cleared his throat. “The world is a complicated place. You are young; merely children. This friendship you have is part of growing up.”

He paused to examine the faces of the two teenagers standing before him. They stared back, impassively. Undeterred by their blank expressions, Dr Bruce carried on.

“It is something that many boys of your age encounter. You might not understand that. These feelings will pass.”

Still Rory and Alistair stood emotionless. How had the headmaster found out? Who had been telling tales on them?

The answers to those questions would have to wait. The headmaster still had his duty to perform.

“But, these feelings are wrong. This is a serious smatter. It must stop.”

The headmaster rose from his large leather chair and moved in front of the desk and behind the boys. In unison Rory and Alistair swivelled their heads to follow his progress.

“Face the front!” he barked.

Although they could no longer watch the headmaster it was clear what he was doing. They heard a cupboard door open, and just as quickly it closed. Then there was an almighty whoosh! sound as the stale air in the study was parted.

“I am going to give each of you six strokes.” He swished the cane through the air once more.

“Turn and face me.”

He flexed the cane between his hands. It was a straight rod. Rory who was something of an expert in such matters thought it was nearly four feet long. It was denser than the canes other masters had used on him, but it easily bent into a perfect arc as the headmaster toyed with it.

“Stand by the bookcase.” Dr Bruce wobbled the cane to make sure the boys understood his instruction.

“Six-of-the-best,” the swished the cane through the air once more. It was a mightily whippy rod.

“You first MacDonald.”

Rory shuffled forward, uncertain what he was expected to do next. Should he arrange himself over the back of an armchair?

“Lower your trousers and underpants and bend over my desk.”

Jeez! Bare arsed. With that cane. The little beauty would certainly take his arse off, he was certain of that.

Seemingly impassive, but with his innards churning, Rory MacDonald breathed in a gulp of air. This would be the severest thrashing of his life. The first ever administered to him by the headmaster. At all costs he must act unperturbed.

Rory could hear the deep breathing of his pal behind him as calmly he unbuttoned his grey short trousers and let them slip down his legs. Then, making certain not to catch the headmaster’s eye as he did so, he put his thumbs in the waistband of his underpants.

With his short trousers and underpants safely at his feet, Rory lifted the tail of his sweat-soaked white shirt clear of the target area and lent forward over the desk, jutting his backside out as if to welcome the cane.

The headmaster could not fail to see that the boy’s buttocks were as nut brown as the rest of his suntanned body. He thought better than to raise it as an issue just yet.

He gripped the cane tightly and rather like a golfer might, he swung the whippy rod at speed across the very centre of Rory’s bum. It sank into the muscle, leaving behind a deep red line.

Rory’s eyes widened and he clenched his teeth hard. Swipe number two followed on swiftly. Another deep mark instantly appeared. Rory made no movement. He had spent five years so far at Willadong Academy. He had developed a high pain threshold.

He remained silent for slashes three and four. A thick line of blood oozed from a particularly deep wound. Rory’s body shuddered slightly, but he made no outward sign that he was in pain. He determined not to give the headmaster the satisfaction of knowing he had hurt him. And, he would not let himself down in front of his pal Alistair.

The headmaster had a righteous duty. It was to save Rory from himself. This flogging was a moral obligation. He stepped back a pace, raised the cane high, swivelled his body at the waist and brought it swishing down, deep into Rory’s buttocks. It fell across two previous cuts and the flesh opened.

Only the merest twitching of his legs showed that Rory felt that one: the agony was terrific. His bum felt as if it had swollen to twice its natural size. Lines of pain shot up and down his legs. The aching in his head was almost as bad as the throbbing in his buttocks.

The sixth and final swipe was aimed low; close to where the underside of the cheeks meets the thighs. Rory choked down the bile that had risen to the back of his throat. He gulped down great draughts of air. His heart raced.

When he rose from the desk, his face was almost as scarlet as his backside. His dead eyes shone. Gently, he pulled up his underpants and eased them over his buttocks. The white cotton immediately turned pink.

Soon his short trousers were in their rightful position and he shuffled across the study and waited, watching quietly as his great friend Alistair dropped his short trousers and pants, bent himself across the headmaster’s desk and prepared to endure the same ordeal.

Five minutes later, back at their room the two naked boys inspected the damage. Their buttocks had never been so scarified. They had no ointment, so they improvised. Alistair rolled his tongue around the inside of his mouth. Once it was heavy with saliva, he stuck it out and carefully, lovingly, washed his dear friend’s wounds.


Episode 4 is here


Other school-based stories you might like

New boy at school

A teenager’s tale


More stories from Charles Hamilton II are on the MMSA website

Charles Hamilton the Second


Rory and Alistair Ep 2.The junior schoolmaster

Rory and Alistair could never conform to boarding school life. The eighteen year olds were oddities at Willadong Academy. They were required to dress like juniors and would remain in short trousers until the day they left school. They had one other characteristic that distinguished them: they were madly in lust with one another.

Episode 1 is here

Alexander Macaulay the junior schoolmaster stalked the passageways of Willadong Academy, a cane tucked under his arm. He was determined it would see action before the afternoon was out.

It was Wednesday and at Willadong that was a time for compulsory sports. If Macaulay found a boy in the building that would be excuse enough. If no abstainer was to be found he could instigate a room search, seeking hidden contraband. Cigarettes and alcohol and much else besides were strictly banned at the school.

Alexander Macaulay was an unhappy young man. This was his second month at the school and things were not going well. He was twenty-four years old; and to many casual observers indistinguishable from the senior pupils. He stood no taller than five-feet-seven-inches and was lean and wiry. His smooth complexion was deeply suntanned but the thin straggly moustache he sported belied his age. He was a boy trying to be a man. He did not possess the “gravitas” required to be a schoolmaster and probably never would.

The tingling he still felt in his backside confirmed this. It had been the most humiliating moment of his life. Less than thirty minutes previously he had been in the study of Willadong’s senior master Mr Henderson; bent across a stout desk, trousers at his ankles. Henderson swiped nine hard cuts across the junior schoolmaster’s swaying buttocks.

Henderson said it was “attitude.” Macaulay must “buck up his ideas.” He must show he was worthy of the title, junior master at Willadong Academy. Until such a time, Macaulay must expect to be treated as if he were a pupil. “Trousers down, bend over.”

Now, Alexander Macaulay was on the prowl. Somebody must pay for his humiliation.

Rory and Alistair lay naked, entwined in each other’s arms. They had had sex enthusiastically, but inexpertly. Alistair’s cock was stiff at a forty-five degree angle. It was ready for round two.

Fresh weals decorated the buttocks of the two eighteen year olds. They were the handiwork of Mr Anderson, their housemaster. It had been six on the bare. They were repeat offenders.

The pain had gone now, but there was one deep cut across the very centre of Rory’s bum that was tender to touch. The cane had landed on the same spot twice. A slash that landed across the back of his thighs troubled Alistair. That should teach him not to wriggle about during a caning.

Some boys were not suited to boarding school life. Roy and Alistair were two of them. There were too many rules and restrictions. The two pals were not resentful. They had broken curfew – again. Rules were rules at Willadong and when they were broken a lad would expect to be showing his arse to a prefect or a master.

Rory freed himself from Alistair’s embrace and lay face down on the bed inviting his chum to inspect his wounds. The teenager licked his own index finger and gently used it to trace from one end to the other of the deep welt across Rory’s bum. It had once been a deep pink, but now was mauve. It would turn purple soon, and then over the next few days it would lighten to yellow and finally disappear.

Alistair created a spit ball in his mouth and washed his tongue with it. Then he licked Rory’s cut, sending a shiver through the teenager’s body and leaving a slime trial across the buttocks. Rory’s cock throbbed almost as much as his bottom had just after his thrashing.

In the distance the school clock struck three o’clock. The boys were missing compulsory cricket practice. Who cared? What was another spanking between friends?

Rory turned on his back and Alistair snuggled up beside him. They took hold of each other’s cocks and tugged.


It was Wednesday afternoon; sports and activities day at Willadong. Rory and Alistair were keen cricketers and part of the school XI team. They should have been with their fellows practising. It was a scorching hot day; like so many that summer. The cricketers were broiling so had left their whites behind in favour of the shortest cotton running shorts they could find. Some wore vests but most were bare-chested.

Cpt Cameron their PT instructor and cricket coach was not a happy man. He had been absent from the school and had engaged a man called Villiars from the village to stand in. Cricket was a gentleman’s game but the sixth-formers at Willadong had been far from gentlemen to Villiars. Willadong boys considered themselves superior to the common man and were not about to be ordered about by a village oik like Villiars.

But now Cameron was back and he did not like what Villairs had told him. Not one little bit.

That was why six eighteen-year-old cricketers were lined up in the pavilion facing Cameron. The PT instructor held a dirty-white plimsoll tightly in his right hand. It was a large slipper and rather worn on the sole. It had seen much action on the running track and also across the bending backsides of errant sixth-formers.

He devised a little ritual. The eighteen year olds stood in a line, backs to the wall. Then on command each one stepped forward three paces towards Cameron. They swivelled on their heels, lowered their white shorts (none were wearing underpants in that heat) and touched their toes; knees straight. Three of the six teenagers wore no shirt so were totally naked bent over obediently with their tight cotton shorts in a puddle at their feet. It was a typical schoolboy ritual; each one presenting himself submissively to his master.

Schoolboy cricketers come in many shapes and sizes. There is no requirement to have an “athletic” body; “big and meaty” could as easily fit the bill. Six sets of naked buttocks were displayed that afternoon: fat and squashy; large and firm; pert and pimply.

Cameron had the perfect view of each boy’s cock and balls and, of course, his crack. But the middle-aged ex-Army officer was not interested in any of that. Discipline and punishment were uppermost in his mind. He gripped the plimsoll tightly and whacked it down across flesh. Two spanks on the left cheek; followed by two on the right.

Then, the boy stood, pulled up his shorts and went back to the wall, to be replaced by the next boy.

And so it went on until all six teenagers had the dark pink outline of the slipper emblazoned across both buttocks.

It looked spectacular, but it didn’t really hurt. Not like four slashes from the headmaster’s special Malacca cane would have if he had learned of the boys’ discourtesy to Villiars.


Alexander Macaulay was despondent. Somebody must pay for his humiliation. He had searched the classrooms without success. No boy was to be found. Now, he made his way through the living quarters. Again, there was no sign of life.

He searched through the study rooms. The boys seemed to have very few personal possessions. For the sons of the wealthy they were very poor indeed, he concluded. The boys would have found the junior master’s naivety touching. They were wiser than that. No self-respecting boy would leave contraband in his room for prying eyes to find. It was secreted in cubbyholes and nooks and crannies across the school; places unknown to the likes of Alexander Macaulay.

He was close to the end of his tour. Only one passageway was left unexplored. The junior master let himself into an unlocked room. As with the others, there was not much there. He opened and closed cupboards and drawers. He was exasperated with himself: what had he expected to find?

Idly he pushed a textbook across a desk. The corner of a picture poked out from between its pages. He tugged it free. It was a page ripped from a magazine. A picture. A captivating photograph.

Two young men, in their twenties, standing side by side grinned at the camera. They had their arms around each other’s shoulders. They were sailors. At least they wore sailors’ hats on the backs of their heads, but little else besides. Only the shortest of denim shorts. The waistbands were unbuttoned and their zippers lowered, enticingly. Their chests were hairless and stomachs tight and flat.

The boy on the right was particularly enchanting. His dark curly hair fell across his forehead emphasising his dreamy brown eyes.

Carefully, Macaulay folded the picture and tucked it into his pocket. Then, fearing he might be caught, he tip-toed from the room.

There was now only one room left unvisited.

Voices. He could hear voices from behind the door. Success. Finally. His afternoon would not be wasted.

Had the junior master been less junior; he would have recognised the room, if not necessarily the voices of its occupants. And, he would have known better than to burst open the door without warning.

Rory and Alistair lay naked. Spent. Breathing hard. Their exertions had been great. Semen covered each boy’s stomach.

Alexander Macaulay stood in the doorway startled. Instinctively, his eyes focused on Alistair’s cock. The junior master had seen nothing like it before. It was flaccid and limp, but even relaxed it was an awesome specimen. And uncut. He had never before seen an uncut cock.

Macaulay blushed deeply. His mouth opened and closed, but he could not get words to form.

Rory raised himself to a sitting position. He stared at the intruder to his room. He only vaguely knew the identity of the stranger. The cane tucked under the junior master’s arm confirmed he was trouble.

“Wha.. wha…?” Macaulay tried again to speak, aware that he could not stop gaping at the two naked sixth-formers before him. One of them, not the one with the huge cock, reminded him of the boy in the picture.

Rory flashed a grin, his dark brown eyes sparkled, but he said nothing, silenced by the sight of the bulge now growing in the front of the visitor’s trousers.

Alistair had seen it too. The caller was quite attractive in a nerdy shy way, he thought.

The junior schoolmaster slipped the cane from his arm into his hand, as if ready for disciplinary action.

Rory roared with laughter.

Macaulay stood rooted, unsure what to do next. He watched as Alistair sat up and the two boys embraced; just like the two sailors. The throbbing in his pants was excruciating.

Alistair giggled, “Don’t stand there all day. Get your clothes off. You can squeeze between us.”

He stopped short, felled by the Macaulay’s face of thunder. The junior schoolmaster wanted revenge for his earlier humiliation. Now he was going to get it.

“No!” He had found his voice at last. He might have been a schoolmaster for only two months, but he understood and relished the power he had over the two teenagers. They must submit to his cane. The consequences of refusal would be dire: a flogging from the headmaster and possible expulsion from the school.

Macaulay swished the cane through the air. He stared Alistair in the eye and slowly and deliberately said, “Let’s have you on your feet and over that chair.” He wobbled the cane at a small straight-backed chair.

To his delight, the boys rose from the bed without question. Alistair clutched the chair and placed it in the centre of the room.

Macaulay’s heart raced. He had never felt such power before. The boys would submit to his will. He watched Alistair make the preparations and start to bend his body over the chair.

No, Macaulay thought. I’ll do the cute one first.

“You,” he pointed at Rory, realising that he didn’t know the names of either boy before him. “You first.”

Rory smiled. It nearly broke the schoolmaster’s young heart.

Rory didn’t fit in at Willadong Academy. It did not suit his personality, but he rarely resented the treatment he received at the school. He broke the rules, he got punished and life went on.

But, not this time. Rory was not a man of the world, but he understood enough. The throbbing cock beneath the schoolmaster’s trousers did not lie. Macaulay was about to beat him on the bared backside for his own sexual gratification. Later, the schoolmaster would pleasure himself while he relived this afternoon in his head.

Rory despised Macaulay for his hypocrisy. He would thrash him and his friend for fooling around. Yet, the schoolmaster so clearly wanted him.

Even before Rory gripped the hard wooden seat, he had devised a plan. Later, sometime soon, he would entice the schoolmaster to a dark secluded part of the school. He knew many such places. Macaulay wouldn’t be able to resist. It wouldn’t take long. A schoolmaster. Sex. A male pupil. There was no need to spell it out.

Rory closed his eyes, clamped his teeth shut and offered up his already corrugated buttocks to the lash of the cane.


Episode three will be published Friday 19 February 2016


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The Gafffer of The Academy 2. In the chill of the night

Kevin revisits his old school

The old boys


More stories from Charles Hamilton II are on the MMSA website

 Charles Hamilton the Second

Rory and Alistair Ep 1. The Head Prefect

Rory MacDonald eased down the handle of the dormitory door with his elbow. His arms were full of cricketing gear and he feared one of the bats was about to tumble to the ground.

He was sweltering in the ninety-degree heat. Would this heat-wave never end? In an ungainly fashion he had the door open and stepped inside. He flashed one of his trademark grins; it split his face in two. In front of him was his best friend Alistair. The eighteen-year-old lay face down on the bed snoozing. He was dead to the world – and totally naked.

Quietly so as not to wake his chum, Rory let the cricket gear fall on to his own bed. Then he sat down and gazed in admiration at Alistair’s body. He was a fine-limbed athletic boy; about five-feet-eight in height. He was hairless on his chest face and buttocks and there was merely down on his legs.

Rory shook his head in amazement. Alistair’s arse and thighs were covered in awesome blue-black bruises. Even from across the room the boy could see the distinctive oval-shaped mark left behind by the hairbrush, which clearly had been applied with some vigour.

Rory looked at his watch; it was time they both got going. He hauled himself from the bed and crossed the room so that he stood towering over his friend. Come on Alistair, he thought, we have a date in town.

Then puckering his lips and leaning forward he planted a wet kiss in the centre of Alistair’s firm left buttock.

The boy awoke like a princess in a fairy-tale.

“Ouch! That hurt,” he grinned.

“Ouch! That hurt,” his friend replied satirically, mocking Alistair’s tone. Both boys exchanged huge grins, puckered up and kissed each other on the lips.

“Pendleton?” Rory asked, nodding at his friends toasted buttocks.

“Who else?” Alistair’s grin never faded. He was not about to let his recent ordeal upset him.

Pendleton was the Head of Wilson’s House. And Pendleton had his own way of instilling discipline among his charges. All the boys who were Head of their House at Willadong Academy were allowed to inflict corporal punishment. There was no set law, but by custom and practice the rattan cane was the instrument of choice. Some Head of Houses used a rubber-soled gym shoe on the youngest of the boys.

Only Pendleton used a hairbrush, applied to a boy’s bared bottom while he was draped across the lap of the Head of House. And, Pendleton did not care about age and seniority. He would just as easily take eighteen-year-old Alistair Crombie across his knee as the most junior fag in the school.

Alistair and Rory were oddities at the school. They were both in their final year at the school, but had never received any privileges. Although they were old enough to be in the sixth-form, they were treated by everyone, masters and fellow pupils alike, as juniors.

They were even required to dress like juniors. Only boys in the sixth-form were permitted to wear long trousers: it was seen as a badge of privilege. The two boys remained in short trousers and would do so until the day they left school. Not that they cared. Temperatures rarely fell below eighty degrees for most of the year; let the “privileged” sixth-formers swelter in their heavy flannel trousers, it was much better to be free to the wind in short trousers.

A short-sleeved white shirt completed the summer uniform at Willadong. Mostly boys did not wear ties or even socks. They would run bare-footed around the school buildings and slip into thongs when outside.

Rory and Alistair could never conform to boarding school life with its myriad rules and regulations. Get up at seven, bed at nine-thirty. Don’t do that; don’t go there. They were more suited to the life of the boys in town. They had made many friends in Woolverton and how they envied them their freedoms. None of the teenagers they knew had fathers who would order them to bend across the armchair for six stingers from a whippy cane because they were out of bed at midnight.

Alistair’s blazing bottom was the result of one such adventure. Bored and unable to sleep, he had climbed through the window and taken himself for a walk. He committed no mischief; he disturbed no boy’s sleep; all he did was to enjoy the moonlight and the clear warm air of midnight.

He was spotted and in the usual matter of course he was reported to Pendleton. Pendleton was not such a huge fellow. He probably was an inch taller than Alistair, but a little thicker set. The Head of House was a fine cricketer and could slog a cricket ball way over the boundary. He had great upper body strength which he put to good use with the hairbrush.

This was not even the first time the eighteen-year-old had been across Pendleton’s knee. The first time he had been ordered to unbuckle his belt and pull down his short trousers, he had been bewildered. He had expected the standard six-of-the-best on the seat; probably whipped in with some force; everyone knew that Pendleton was a bit of a bully. But, to be ordered to go across the prefect’s knee like he was six years old was a shock.

Alistair had no choice. The alternative would have been a visit to the headmaster’s study and a thrashing of a lifetime, almost certainly bare arsed and no doubt with the awesome Malacca cane. That could take a boy’s backside off, leaving him in considerable pain for many days.

No, unconventional though it was, Alistair had to submit himself to Pendleton.

The hairbrush had once belonged to his nanny. Pendleton had felt its sting across his own bared bottom many times until when at the age of eight he was sent off to prep school. The hairbrush was the only memento he had of nanny; he stole it from her room the day he found her dead in her bed.

The over-the-knee bare-bottom spanking hurt like crazy, but it was nothing like getting the cane; even when wearing trousers and underpants. Alistair supposed the ordeal was meant to humiliate him. If so, Pendleton had chosen the wrong boy. He dropped his short trousers and unbidden stepped out of them. Then perfecting an air of unconcern, he put his thumbs in the waistband of his pants and lowered them down his thighs and let them fall to his feet, then he stepped out of them too and kicked them a few feet behind him. He now stood naked from the waist down in front of his would-be tormentor.

Alistair was very proud of his body and was not ashamed to be seen naked. His pal Rory was one of his greatest admirers and often they would compliment one another on their anatomy. Rory, for one, had a very distinctive penis; it must have been almost the only uncut specimen in the whole school.

Rory had no idea what was going through Pendleton’s mind as he draped himself across the boy’s legs, lowered his head so he was almost kissing the carpet and keeping his own knees straight, raised his taut athletic buttocks high to receive his spanking.

Wow! Pendleton was in a frenzy. Had some demon taken possession of him? Relentlessly he whacked the heavy oval hairbrush up and down into and across both buttocks. With no respite between smacks, he covered every square inch of buttocks and thighs inside thirty seconds and then he just kept on whacking and whacking.

Alistair had never been spanked like this before, so he was not sure how much it was supposed to hurt. It did considerably, but to his puzzlement he found the pain increased rapidly with the first few dozen slaps and then plateaued. He had gone through some king of pain barrier. After a time, he could feel the heavy wood crunch into his globes but each additional whack did not increase the pain.

The teenager sucked in his breath and waited as patiently as he could in the circumstances for Pendleton to complete his task.

He was beaten quite literally black-and-blue. But, even as he climbed back into his underpants and short trousers Alistair realised the pain had subsided, leaving behind a gentle throb that quickly turned to a warm glow. Some parts of his bum, especially the bit where the cheeks met the thighs were tender to the touch and he might feel the spanking for some time when he sat down on a hard surface.

Pendleton was a young man of few words and he dismissed Alistair without benefit of a lecture. As he exited the study, Alistair turned and flashing his sparking white teeth, he grinned, “Thank you Pendleton, I enjoyed that. I hope you did too.” Then he closed the door and ran down the passageway in case the Head of House had resolved to drag him back inside for a repeat performance.


Episode 2 is here.


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Six of the best caning stories 1. The sixth-formers

The padded armchair

Murph in the headmaster’s study

More stories from Charles Hamilton II are on the MMSA website

Charles Hamilton the Second

COMING SOON: Rory and Alistair of Willadong Academy

Meet Rory and Alistair. They could never conform to boarding school life with its countless rules and regulations. Get up at seven, bed at nine-thirty. Don’t do that; don’t go there. The two eighteen-year-olds were more suited to the life of the boys in town.

They were oddities at the school. They were both in their final year at the school, but had never received any privileges. Although they were old enough to be in the sixth-form, they were treated by everyone, masters and fellow pupils alike, as juniors.

They were even required to dress like juniors. Only boys in the sixth-form were permitted to wear long trousers: it was seen as a badge of privilege. The two boys remained in short trousers and would do so until the day they left school.

They had one other characteristic that distinguished them: they were madly in lust with one another.

Starting Monday 15 February 2016 and continuing on Wednesday 17 and Friday 19 February; three episodes from the life of Rory and Alistair of Willadong Academy.


Episode 1. Alistair goes over the knee of House Captain Pendleton for a severe dose of the hairbrush. Will the punishment stop the eighteen-year-old from climbing out of the window at night?

Episode 2. A frustrated junior schoolmaster needs to cane some arse. He prowls the school but all the boys are out at cricket. Except Rory and Alistair. They are in their room in each other’s’ arms and the schoolmaster is getting ever closer.

Episode 3. The headmaster has his own cure for Rory and Alistair’s ‘affliction.’ There’s nothing that a sound thrashing can’t cure. Or can it?


Seemingly impassive, but with his innards churning, Rory MacDonald breathed in a gulp of air. This would be the severest thrashing of his life. The first ever administered to him by the headmaster. At all costs he must act unperturbed.

Rory could hear the deep breathing of his pal behind him as calmly he unbuttoned his grey short trousers and let them slip down his legs. Then, making certain not to catch the headmaster’s eye as he did so, he put his thumbs in the waistband of his underpants.

With his short trousers and underpants safely at his feet, Rory lifted the tail of his sweat-soaked white shirt clear of the target area and lent forward over the desk, jutting his backside out as if to welcome the cane.

  • Extract from episode 3