The Tyrant Headmaster 5: Back in short trousers

Previous stories from The Tyrant Headmaster

The Boy in The Bar here.

A new beginning  here.

The prefects’ reckoning here.

Smoking on Saturday here.


The steam train chugged along the branch line on its way to town. Aboard making their daily journey from the villages were thirty-two boys heading for St Septimus Independent Grammar School.

One train took the boys to school in the morning; another brought them home in the afternoon. Most days the boys were the only passengers. Most days; but not every day.

What fun the boys had; jumping up and down on the seats and fighting, or poking their head out the window to shout at scarecrows and cows in the fields. Some sang rude songs, one about Dr Fortescue, the headmaster, was chanted with special enthusiasm.

The first-formers were the most boisterous. You could tell they were first-formers by the smart grey short trousers they wore. Shortly after he became headmaster Dr Fortsecue had decreed that all boys joining the first form must wear short trousers. Nobody much complained. The boys wore short trousers in their primary schools; they were used to them.

Dr Fortsecue was pleased his plan met with no opposition; it would fortify him for what was to come. The new first formers would continue to wear short trousers in the second form, and the third, and right up until they left the sixth-form aged eighteen. By the time he had finished every boy in the school from the most junior to the most senior would wear short trousers.

Dr Fortescue believed in short trousers. Proper trousers; not the cotton shorts people wore during the summer. The school uniform had authentic grey short trousers; just like the long trousers the boys presently wore, except they were tailored to just above the knee. Long socks completed the ensemble. He thought they looked delightful with the school’s blue-and-white blazer and cap.

Yes, the doctor enthused to his staff when he announced the school uniform change. The boys were children and they should be reminded of such. They would dress like children and respect their schoolmasters and other adults accordingly. Failure to do so would result in punishment. And like the Good Book said; that meant the rod, or more specifically three feet or more of whippy school cane.

Dr Fortescue gripped the telephone in his hand so tightly his knuckles had turned white. This contrasted distinctly with his face which was glowing bright red. His fury increased with every word his caller spoke.

At last, the call terminated, the headmaster slammed the receiver down with such force it bounced out of the cradle and landed on the top of his desk.

Outrageous! A disgrace! There will be hell to pay! How was such a thing possible? Boys from his school behaving like hooligans on the train. Guttersnipes. He wouldn’t expect the oiks at Gumshoe Lane Secondary Mod to behave this way.

Minutes later Mr Tavistock the deputy headmaster stood in front of the headmaster’s desk. He was an elderly man, close to the age of retirement, but that did not stop him feeling like a very naughty first-former while Dr Fortescue berated him about the boys’ behaviour.

At last, the headmaster’s rage subsided long enough for Tavistock to interject.

“We can easily find the boys’ names. The same ones use the train every day.”

“Do it!” roared the headmaster. “Every boy on that train must be thrashed. Get a list, instruct their housemasters. An exemplary caning for each one of them.”

Tavistock hesitated. Every boy? How could we be certain that all the boys were guilty? He opened his mouth the voice an objection.

“Go Tavistock, go!” the headmaster interjected. “Get the job done, man.”

With that the elderly deputy headmaster fled the study.

Two hours later Tony Sinclair and Alan Reid stood terrified before the headmaster’s desk. News had spread around school; all the boys on the train were to be thrashed by their housemaster. Every one; no exceptions. But that wasn’t entirely true. Not everyone would be caned by their housemaster. Sinclair and Reid, the only two prefects on the train, would get a special headmaster’s flogging.

“Shit,” Tony had said to Alan when the summons to the head’s study had been delivered. “We weren’t shouting and singing. Why are we to get a bowing?”

“We’re prefects,” his despondent friend replied. “He’d say we were supposed to stop them. That’s our job.”

“What, you think we should get our arses roasted for this? What the fuck were we supposed to do?”

Alan shrugged his shoulders. He loved being a prefect at St Septimus, his mother was so proud of him. But, and he dared not say this to his pal Tony, he was a little ashamed of himself that he didn’t try to calm the boys down.

“Come on,” Alan said with a confidence he did not really feel, “Let’s get this over with.”

Dr Fortescue was an elderly, tall, grim man. He glared at the two eighteen-year-olds who stood before him. His contempt for the wretched prefects was undisguised.

Alan had been correct. The headmaster wanted to blame them entirely for the hooliganism on the train. He jawed and jawed. “Disgrace to the school … no longer to be prefects … no better behaved than a first-former.”

Alan only half heard. He couldn’t concentrate on the lecture. His hands shook so violently he had to clasp them behind his back so that he looked like a minor member of the Royal Family. On and on, the headmaster lambasted the pair.

Next to him Tony stared blankly ahead. He could not meet the headmaster’s eye so concentrated on a spot on the wall over the old man’s left shoulder.

“Do you remember what I told the sixth-form last Wednesday?” The headmaster paused awaiting a reply. But none came. Neither boy had been listening. Suddenly Alan woke with a start. What? Had the headmaster asked him a question?

“Pah!” Dr Fortescue’s face blazed red. The impertinence of these boys. “I told you,” he said, answering his own question, “that if senior boys chose to behave like first-formers, they would be treated like first-formers.”

Alan’s startled face betrayed his own thoughts.

“Well Reid,” the headmaster dripped sarcasm. “You appear to have woken up at last. What did I say would be the consequences?”

Alan knew exactly what the headmaster meant. All the sixth-formers had roared with laughter at the absurdity of the idea. Laughed that is once they were out of the earshot of Dr Fortescue.

“Sh… sh..” Alan couldn’t get the words out.

“Come on boy!” the headmaster spat. “What did I tell you?”

The trembling sixth-former took a gulp of breath and blurted, “You said we’d be made to dress like the first-formers. We’d be made to wear short trousers.” He caught the glare of the headmaster’s icy blue eyes and added hastily, “Sir.”

“Yes,” the headmaster barked, “and that is precisely what will happen to you two.” He waited for the news to sink in, delighted that both of the eighteen-year-old pupils shuffling their feet on the worn rug had paled significantly. Then he added, with much malevolence, “You will report to matron immediately who will supply each of you with a pair of short trousers.”

The headmaster had prepared a little speech. “You will wear them at all times in school and also on your journey to and from home. I shall give you each a letter to take home to your parents to explain the situation.”

Alan turned to his friend Tony, but the boy deliberately avoided eye contact. Wear short trousers. All the time. With the first-formers at school and on the train. This was too humiliating for words.

It was as if the headmaster could read the boy’s mind.

“You only have yourselves to blame. Now, off with you. Go see Matron. Then return to my study immediately for an exemplary thrashing.”


It had only taken a moment. Matron seemed to be expecting them. She had already selected their clothes. Dolefully, Alan slipped off his shoes, unbuckled the belt on his trousers and let them fall to his ankles. He sat on a hard wooden chair to tug them off his feet. He glanced over at his new grey school short trousers. When, he pondered silently, would he ever see his long trousers again.

Tony picked up his own pair of short trousers. They were very smart, he had to admit. He stepped into them and pulled them up tight. They fitted very well indeed. They fell to about an inch above his knee. The waist was elastic and could stretch comfortably around him. It was as if they had been tailor-made. He pulled up the long grey socks and his transformation was complete. Tony Sinclair, aged eighteen, sixth-former and until minutes ago a school prefect, now reduced to looking like a junior.

He glanced across at Alan. He too had completed his change. “C’mon,” Tony said, “We’d better get a shift on, we don’t want to keep the Beak waiting.”

Alan would have been very content at keeping the headmaster waiting. He did not want to leave the sanctity of Matron’s office. The moment the two left the whole school would see their indignity. He could not bear that and nor did he think he could take the headmaster’s promised “exemplary” thrashing.

The boys watched with terror as the headmaster slipped off his tattered academic gown and draped it on a hook on the door, then took off his suit jacket and hung that up too. He was determined to show he meant business.

He might be elderly, but Dr Fortescue stood tall and erect. He strode purposefully across his study, opened a door to his cabinet and without looking reached his hand inside. He knew exactly what he wanted. The hand emerged seconds later gripping a fearsome Malacca cane. He turned around and clutching the cane by its distinctive brown leather handgrip he swished the rod through the air.

Two pairs of eyes transfixed on the cane. Both boys had been caned before; Tony Sinclair many times, it was that kind of school. But neither had ever confronted such a terrifying instrument of punishment. Unlike most school canes, the rod had no crooked handle, instead it was almost entirely straight, although there was a slight warp half way down its length; the result of much use against the stretched backsides of errant senior schoolboys.

The headmaster flexed the cane between his hands, deliberately to intimidate the two boys before him. It worked. They saw a rod more than three feet in length and as thick as a man’s little finger. Along its length at three or four inch intervals were hard knotted rings. It was these that made the Malacca so awesome; even if a boy wore regulation school trousers and underpants this little beauty in the right hands could rip a backside to shreds.

Dr Fortescue paced up and down the open space in the centre of the study, lecturing the two eighteen-year-olds about his disgust at their behaviour, flexing the cane the whole time. The boys’ heads bowed lower and lower, their hands now clasped behind their backs, as though trying to protect their bottoms from the imminent whipping.

“Reid,” the headmaster growled. “Take that chair and place it in the centre of the room.” He pointed at an old, worn wooden chair. It had a straight back and no arms. The teenager, his heart thumping, moved the two steps it took to cross the room and gripped the chair by its shiny seat. It was heavier than he had expected and he had difficulty man-handling it into the required position.

“Turn it so that its back faces you.” Dr Fortescue was enjoying himself. Sometimes he loved to make the miscreants prepare the setting of their own punishment; it added greatly to the tension of the occasion.

Satisfied that the chair was suitably situated, the headmaster swished his cane through the air once more, this time pointing it at his desk. “Take off your blazers and place them on my desk.” He swiped the cane once more in case there was any doubt where he meant.

Saliva dried in the doctor’s mouth as he watched the two boys disrobe. He especially noticed how much Tony Sinclair’s hands trembled as he tried and at first failed to undo the three buttons on his blazer. Each boy wore a shining white school shirt; their mothers must have been very proud of them. But, a patch of sweat on Tony Sinclair’s back rather spoilt the effect.

“Stand there both of you.” Once again the cane moved at speed through empty air. This time the headmaster swished the rod in the direction of the study wall and two dejected sixth-formers shuffled across the carpet.

“You first Reid. Stand behind the chair, bend over the back and grasp the seat. Head down low, buttocks out.”

Alan Reid blinked with relief. He almost smiled. Bend over the chair, the head had said. Phew! He had been promised an “exemplary” thrashing. Surely, that meant trousers and pants down: bare arsed.

Quickly, before the headmaster could change he mind, the boy took three paces forward, hesitated for a mere moment and stretched over the back of the wooden chair.

“Pah!” the headmaster thought to himself. “The boy does not seem to be overly concerned about the whipping he is about to receive. Well we shall see about that”

Dr Fortescue took a step back to get a full view of the teenager bending before him. Reid was a tall lad, easily six feet, and rather lanky. The short trousers that he now wore fitted him well at the waist, but they were made for a much shorter boy. They fell to about three inches above the knee and in the bending-over position they rode much higher up his thighs. The smart short trousers encased Reid’s jutting and rather full bottom beautifully, offering the headmaster a wonderful target to attack.

Dr Fortescue hovered the cane over the middle of the former prefect’s awaiting buttocks and draw it back and up so that it came level with his right shoulder. The headmaster was an expert with the cane; after all he had developed his technique over many years. It was a simple matter of motion and energy needing a flick of the wrist just a fraction of a second before the cane struck into the waiting bottom.

It was a stroke of tremendous force that landed straight across Reid’s prominent backside. There was an audible intake of breath: he felt it even if he managed to avoid moving or screaming. There was an equally audible intake of breath from Sinclair who was standing by watching his friend receive what was undoubtedly going to be the thrashing of his lifetime.

This might not be a bare-bottomed thrashing, but the Malacca cane easily sliced through layers of trousers and underpants. The agony in the boy’s bum was intense, even after only a single stroke.

The headmaster raised the cane high and lashed it firmly across the quivering posterior. As he removed it another thick line formed underneath the boy’s tight white underpants.

He left the most severe of the strokes until the fourth and fifth. There was more force in number five and Reid howled, stood up straight and clutched his brutalised bottom. Tears flowed down his flushed cheeks and a trail of snot dribbled from his nose.

The headmaster glared in silence. It took the wretched sixth-former a minute, but he got his breath back and forced himself to bend over for the final stroke.

The head took a bit of a run up whipping the cane down hard, Reid yelled as the last stroke whipped hard into his under bottom where the bum meets the thighs; the most sensitive part of a boy’s anatomy that is exposed during a caning. It would ensure he was reminded of his punishment every time he sat down for a few days.

“You may stand Reid.” The headmaster atoned haughtily. The boy leapt to his feet rubbed away at his bum and slid his arm across his face to clear the tears and snot and then with eyes cast down resumed his spot at the wall.

used school shorts after (3)
He rubbed away at his bum

“Sinclair. Take his place.”

Moments later Tony was admiring the seat of the wooden chair from a very close distance. It was an ancient chair and much of the varnish on the seat had been removed by years of wear. The sides that he gripped tightly were completely bare wood. How many dozens (hundreds?) of boys had contributed to this over the years?

Dr Fortescue held his cane tightly and began to take his aim. The boy seemed stoical, his breathing was heavy as must be expected in the circumstances, but he held his bottom up steadily awaiting the first lash of the Beak’s cane.

The headmaster respected boys who accepted without fuss that they must be punished for their faults and that their backsides should pay under the rod to atone for their transgressions.

He expected a pupil to bend over when instructed and to present his behind unflinchingly. But, the headmaster also wanted the boy’s bottom to vibrate and quiver as the cheeks reddened. That would testify to his own skillful prowess with the cane. But, he knew a caning was a contest: the headmaster must inflict considerable pain and, however much the boy bending before him accepted he deserved his beating, the boy would try to show he did not feel it.

If that had been Sinclair’s intention, he failed miserably. He was in tears after the second stroke. His bottom danced under the strokes of the cane and twice the headmaster was forced to remind him not to struggle. The threat of extra strokes made him comply. After the full six strokes had been given, he lay sobbing over the chair, wheezing for breath. He was a very sorry boy. Which, the headmaster knew without a shadow of doubt, was what he should be.

The double beating over, the headmaster sat down and placed the cane on the desk and filled in the punishment book. Both boys had recovered sufficiently from their ordeal to take the pen when offered and signed their names. The throbbing in their backside was intense, but tears and snot had ceased to flow.

The headmaster stood and walked across the study to return his cane to its resting place. Without looking at the boys, he ordered “Return to class,” and within seconds they were gone. The first ordeal of the afternoon was over. The caning had been delivered and received. Now, the two eighteen-year-olds had to return to class dressed in their smart short trousers to suffer the mockery of their fellow sixth-formers.


Other stories you might like.

The Gaffer of the Academy: 1. Beginnings

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The dope smoker


More stories from Charles Hamilton II are on the MMSA website


Charles Hamilton the Second

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