The Chamber pot incident

The headmaster sat back in his plush leather chair contemplating the boy standing on the other side of his huge walnut desk.

Perry Dexter, aged eighteen, nearly six-feet tall, a senior sixth-former, captain of cricket, a prefect. And a thoroughly silly boy.

Dexter wore a white shirt, green-and-black striped tie and mid-grey short trousers. He had on leather sandals, but no socks. Eighteen years old and wearing short trousers. And they were real trousers. Properly tailored trousers that were short. Not the kind of shorts people wore to the beach. The headmaster knew that back in his homeland no self-respecting eighteen-year-old would wear short trousers to school. But here under the harsh African summer sun it made perfect sense. All the boys from the youngest to the most senior wore short trousers.

Dexter’s shorts were short and Dexter was tall, so they hardly covered much more than his buttocks and an inch or so of his thighs. The boy didn’t seem to mind. He wasn’t the only pupil at the school dressed like that.

Dexter posed the headmaster a problem. He needed to be punished, there was no doubt about that. But, he was a senior sixth-former, eighteen years old, an adult. How did one punish somebody like that?

The stupid boy had climbed on the roof of the clock tower and then shimmied up its steeple and deposited a chamber pot on the very top. It was dangerous, the fool could have easily fallen and broken his neck. It was a terrible example to set the younger boys.

It had all been so public. Everybody knew what he had done. The headmaster could not ignore it. It could not be brushed under the carpet. So, how could the boy be punished? It had never been much of a problem in the past. Sixth-formers were by and large well behaved. They were left to their own devices. No master would interfere with their lives.

But now? The headmaster had contemplated expelling the boy, or at least suspending him for a term. But, examinations were looming. If the boy missed classes, he would certainly fail them. Then what? No place at university. No lucrative career. And all because of a childish prank.

No. The headmaster had decided. Dexter would not be suspended or expelled. That left only one recourse to action. If the boy behaved like a child, he should be punished like a child. No matter how disagreeable it might be, it had to be done.

The headmaster had finished jawing the boy. It was now time to take action. He hauled himself out from his chair and walked in front of his desk. Dexter’s eyes followed him intently. The headmaster took hold of a low-backed armchair and swivelled it until its back faced into the centre of the room.

Then, to dispel any doubts about his intentions, he strode to a tall thin cupboard in one corner of the study. He opened the door. Dexter averted his eyes. He knew what was kept inside. He could hear a distinct rattle as several whippy rattan canes rolled around as the headmaster searched for just the right weapon.

Dexter was a sixth-former. This was a unique situation. It deserved something special to meet the occasion. The headmaster withdrew a long, stout Malacca cane. He held it between his hands and studied it closely, as if seeing it for the very first time.

It truly was the first time Dexter had seen the beast. It was more than three feet long and as thick as a boy’s finger. It had notches every three or four inches along its length. That was what made the cane so awesome. It would bruise a boy’s backside worse than any other of the canes in the headmaster’s considerable collection. When administered with vigour across bared buttocks it would tear the flesh to ribbons.

The headmaster turned to face Dexter and swiped the monstrous cane through empty air. It made a terrific swish as it travelled.

The headmaster pointed with his cane. “Please stand behind that chair.” A look of bewilderment spread across Dexter’s face. It was a handsome face with dark piercing brown eyes and elegant full lips. He was blessed with a gorgeous smile and when he grinned his whole face lit up. But, he was not smiling now. The cane? He, a sixth-former was to be caned? Had a sixth-former ever been caned by the headmaster in the whole history of the school?

He stood rooted to the spot. Unsure what to do. The headmaster’s clear icy blue eyes fixed a penetrating gaze on the boy. He was unaccustomed to this. A boy always obeyed the headmaster’s command. Without question.

“Dexter!” The headmaster’s craggy face scowled. He swished the cane once more. “To the chair boy.”

Hesitantly, Dexter shuffled the three or four paces needed to reach the chair. He stood behind it as instructed. It was an ordinary “easy” chair, modern in design. The kind you might see in an office or a home. Dexter was a tall boy and the apex of the chair was several inches lower than his waist. It had foam cushions, one on the back and another on the seat, covered in a heavy coarse bottle-green material. Its arms and legs were made of a light wood.

The headmaster swished the cane once more. “Let’s have those trousers down, Dexter.”

The eighteen-year-old turned his head towards his tormentor and opened his mouth to voice a protest. He caught sight of the awesome cane now tucked under the headmaster’s right arm and shut up. He did not want to antagonise the man. Besides, Dexter knew the reality. The headmaster was in charge and he, Dexter, had no choice but to obey. That was just how it was. That was how the universe was organised. The boy submitted to the master’s command.

He drew in a deep breath. Matters had to take their course. A caning on the underpants. It couldn’t hurt that much, surely? His short trousers had a half-elasticated waistband so he needed no belt. He unclasped the metal fastener at the top of his zipper, unzipped and let the trousers slither over his buttocks and down his thighs where gravity took them to rest on top of his brown sandals.

His white Y-front underpants fitted a little too snugly. It was clear to any observer that Dexter was no longer a small boy; he was a fully-grown man.


The headmaster slid the cane from his arm into his hand and tapped its tip across the back of the chair. “Bend over the chair, Dexter. Bend over.”

The boy shuffled a few inches forward. Took a deep breath and laid himself across the chair.  He was so tall and the chair so small that his stomach cleared the top of the chair by several inches. He held tightly to the wooden arms.

The headmaster took up his position to the left and slightly behind the boy. He laid his cane across the middle of the boy’s underpants. But something was not quite right. No, the headmaster thought, this would not do.

“Lean further forward, Dexter. Take hold of the front of the seat cushion.”

The sixth-former manoeuvred himself forward. Now, his back was arched and his buttocks were presented more tightly. But the headmaster was still not satisfied. He took hold of the tail of the boy’s gleaming white shirt and gently folded it, once and then twice. Now, several inches of Dexter’s hairless back were displayed and the shirt was well away from the target area.

Next, the headmaster gripped the waistband of the Y-fronts. Dexter drew in breath sharply. “Dear God,” he thought, “the Beak’s pulling my pants down. He’s going to cane me on the bare.”

But he was not. Instead, the headmaster pulled the underpants tightly. It had the effect of lifting and separating each buttock. The boy’s crack showed as a deep ridge down the centre of the underpants. Now, they fitted like a second skin. They would afford him no protection. As far as pain was concerned, he might as well be presenting himself bare-arsed for his thrashing.

The headmaster had been a keen cricketer all his life and he swiped the first stroke into Dexter’s backside with the same ferocity he would use sending a ball to the boundary. The impact surprised the boy and he rocked backwards and forwards while simultaneously gripping the chair cushion for dear life and screwing up his eyes in a futile attempt to absorb the pain.

If the first stroke was a “four” to the boundary, the second was a “six.” The headmaster used an uppercut to enter the boy’s buttocks in the fleshy underside and tried to exit somewhere near the top of the globes. Dexter rose on his toes, hunched his shoulders, closed his eyes and gurned his face by closing his top lip over his lower.

The headmaster waited patiently for Dexter to settle. Already, he could see two clear lines running parallel across the boy’s tight white underpants. Beneath the cotton, there would be a strip of raw flesh at least an inch wide throbbing like crazy.

Dexter thumped the chair’s cushion with a clenched fist and howled when the third swipe struck him. It was low, right where the bum cheeks met the thigh. The cane had bypassed the underpants altogether and struck bare flesh. A vivid red mark instantly appeared. Sweat drenched the boy’s shirt. His heart was thumping like he had just won a one-hundred-yards race at an Olympic record. He wriggled his hips, pushed his bottom further out. Hopped on one foot, then the other.

“Steady boy. Steady.” It was a curt command and one that the headmaster expected to be obeyed. He did not take kindly to boys who did not accept a thrashing stoically.

Dexter summoned up all his powers of concentration. He would take this caning like a man. He simply would.

Number four landed higher, but with no less ferocity. The headmaster beat carpets with less force. Dexter smashed his head from side to side, as a horse might when avoiding being bridled. The pain which had started in every nerve end of his posterior now travelled up and down his legs. His knees buckled, the soles of his sandals slipped against the carpet beneath his feet.

The headmaster believed that a “headmaster’s caning” should be awesome. A boy would never wish to return to the headmaster’s study. It would be an experience he would not forget for the rest of his life.

He moved his position slightly and placed the cane across Dexter’s buttocks so that it lay diagonally from the bottom left corner to the top right. Then with a powerful forearm jab he brought it swishing down across the four cuts already aching across the boy’s bum. It brought each of them to life once more and added its own bite to his ferociously burning bottom.

Dexter gripped his head in his hands; his face contorted like a gargoyle. His hips swayed. His mouth opened and closed silently, like a goldfish.

The headmaster laid the cane for the final time across the boy’s buttocks. This time from bottom right to top left. Swipe! There was now a perfect “X” across Dexter’s rear end. He repeated his military dance, stamping his feet up and down. His buttocks sashayed. His back arched. He gulped in draughts of air. He couldn’t breathe, the furnish blazing across his buttocks had quite literally taken his breath away.

The headmaster paused, watching the boy carefully. Dexter’s bottom appeared swollen. There were clear cane marks across the seat of his underpants. It looked like welts had already risen. Yes, the headmaster told himself, it was a job well done.

“You may rise, Dexter,” it was a pompous, haughty command.

Slowly, the boy released his grip on the chair and straightened his back. His short trousers remained at his feet. Even without touching his behind, the boy knew it had the texture of leather. Never in his life had he experienced such agony before, not even when he was nine years old and fell off his bicycle and fractured his wrist.

His beautiful brown eyes shone. They were washed with tears, but he was not actually, technically, crying. He would be able to make that claim later when recounting his ordeal to the other chaps.

He bent down and retrieved his trousers. He hissed slightly as the pain reignited as he pulled them across his buttocks.

The headmaster completed an entry in the punishment book and passed it across his desk for the boy to sign. Dexter flashed him one of his most impish grins. He did not resent the beating he had just endured. He had been a damn fool, he knew that. The headmaster had no choice but to thrash him severely. It was what he deserved.

In any case, he thought, as he exited the study. He would be a hero twice over with his chums when they inspected his wounds. First, for climbing the clock tower and leaving the chamber pot and second for being the first sixth-former in history to take a headmaster’s whopping.

Picture credit: Sting Pictures

Other stories you might like


The old boys

The boys in the mailroom

Professor Paddle


 More stories from Charles Hamilton II are on the MMSA website


Charles Hamilton the Second

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