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


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