The Tyrant Headmaster 8. The student master

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For all the previous episodes of The Tyrant Teacher, click here

Steve May slowly closed the door to the study behind him.

He stood blinking the tears. Tears of humiliation; tears of pain. His backside throbbed like crazy. A minute or two earlier it had been intense agony, but it was easing a little. It would be several hours before the pain went completely.

How he hated that school. He would gladly see it burn to the ground. All of it and the schoolmasters with it.

Slowly, he eased his way down the passageway. Every step he took was agony as the elastic at the bottom of his underpants cut into his blistered bottom. He limped downstairs and through the lower school passageways, hands gingerly touching his buttocks. He couldn’t help it; he desperately wanted to rub his scorching bottom. His eyes were still wet and blurry as he made for the bogs and a cubicle in which to hide for a few minutes, until he’d regained some composure.

He cried a bit more; his bum was throbbing madly and the pain was killing him.

That night, alone in his horrible furnished room, Steve wept into his pillow and nursed his scarred buttocks. He still had weeks to go until he would be allowed to leave St Septimius. How would he survive?


Four weeks earlier


Steve May’s progress was painstaking. He crossed the ivy-covered quadrangle, passed the mullioned-windows of the library and entered the clock tower. He had never been in such a place before. What kind of school was this?

At a snail’s pace, he climbed the stairs in search of Mr Fortescue’s study. “Study:” even the words they used here intimidated him. Study: what was wrong with office? That was a perfectly good word. Steve was in search of Mr Fortescue, the headmaster, the man who was to be his mentor for the next eight weeks, while he undertook his teaching practice.

He was not looking forward to this. Now, he had to prove that he really had the makings of a schoolteacher. Eight weeks was all the time he had. If he failed that was the end for him. But success meant qualification and “Steve May” would become “Mr May,” a junior teacher.

The school porter had told him the study was on the first floor. He found that easily enough and was scrutinising the nameplates on the oak-panelled doors when he stopped in his tracks. Beyond the door of the study at the far end of the corridor came a distinct sound. Swish! Thud. Swish! Thud.

His heart beat faster. Was that what he thought it was? His naturally pale face coloured up with embarrassment. He stopped, stood still, unsure what to do next. Suddenly the door of the study eased open and a boy, bulkier and taller than Steve, emerged. Steve’s attempt to avoid eye contact was a failure. The boy glared at him: his expression a mixture of pain and resentment.

The pain was born of being forced to drop his trousers and bend over a chair to allow Fortescue to swipe his cane across his stretched white underpants and the resentment was forged when this stranger witnessed that humiliation.

The sense of intimidation Steve already felt increased as he formed a slack fist and ever so lightly tapped on the study door. He half hoped Dr Fortescue would not hear the knock so Steve could withdraw and leave the school forever. He would tell his tutors at the teacher training institution that nobody had been expecting him at the school.

“Come in.” Rats! He had heard. There was no going back now for Steve May. He had arrived at St. Septimius and he would have to survive all that the school threw at him in the next two months.

He turned the handle and opened the door slightly as if he was trying not to be a nuisance and squeezed through the small gap he created between door and door jam.

Steve looked around the study. It was dominated by a huge desk, topped with green leather. Behind it was a window that overlooked the school grounds with its ivy-covered walls and mullioned windows.

The walls of the study were panelled in oak. A large open unlit, fire dominated one wall and two others had shelves and cabinets, including a tall thin cupboard with a smoked-glass front. A Chesterfield couch and two padded armchairs made up most of the furniture, but there

Standing against the wall was a wooden chair with a high back over which, Steve would one day discover, boys had to drape themselves when being caned. Behind this was a comfortable seating area where presumably Dr Fortescue held informal meetings. Steve’s eyes, however, were drawn to the object laid across the desk, a thin yellow stick with a curved handle: the cane.

“You must be May.” Dr Fortescue gave him a frosty glare making Steve feel like a naughty twelve-year-old schoolboy. The fact that the cane was resting on the desk did little to modify that. In his mind’s eye, he could see that resentful schoolboy stretched across the desk, bottom high. When Fortescue beckoned him with a crook of his finger to go and stand in front of his desk Steve was certain he was in for similar treatment.

He shuffled forward, eyes lowered. Steve had been overwhelmed from the moment he walked through the gates of St. Septimius. He had never seen such a place. He had attended a modest inner-city secondary modern school made of breeze-blocks and glass, far removed from the ancient buildings at St. SIGS.

Dr Fortescue’s glare fixed on Steve who intuitively stared down at his mud splattered shoes, terrified he might make eye contact with the headmaster. He shuffled from one foot to another in embarrassment.

Dr Fortescue had a red face with a heavy frown on his brow and his thin lips were set tightly. None of the boys were sure of his age; he probably looked older than he actually was. He was an intimidating man, as strong as an ox.

Fortescue did not like what he saw. Who was this pale-skinned scrawny creature dressed in a cheap suit from the Co-op, who stared at the carpet too petrified to even look at him? Who on earth thought he could become a schoolmaster? If he wore one of St Septimius blue-and-white blazers he might be mistaken for a sixth-former. Heavens! Put him in short trousers and he could pass as fifteen.

“So, you are May.”

Steve blushed scarlet. Was he expected to answer? He wasn’t at all certain.

“Well, answer me boy!” Already Dr Fortescue was treating his new “colleague” as if he were a disobedient pupil.

“Yes, Sir. Sorry Sir.”

Fortescue’s already ruddy complexion turned puce with rage. That lower-class accent! Where was this urchin from? Some industrial town in the Midlands: Wolverhampton? Walsall? How could he be expected to teach English, when he couldn’t even speak the language correctly?

He turned his back on Steve and stared out of the window. What was the world coming to? He blamed the new Socialist government. They wanted to abolish schools like St Septimius. Jealousy. Class envy, that’s what it was. The school had been forced to take scholarship boys from the working classes and now it was expected to take on this wretch as a student master. What next: admit West Indians? Independent schools were supposed to “give something back,” the Socialist, no crypto-Communist, Minister of Education had said. “Give something back”: what the hell did that mean?

Fortescue stared through the window. A bell rang in the distance and hundreds of schoolboys in St Septimius colours emerged from classrooms. Bloody Socialists, he thought, they want everybody to be the same.

He turned to May. “Get out of my sight and never come back,” is what he wanted to say. But he had been given his instructions by the school governors. He knew he had to deal with this person and his strangled vowels.

So, instead of throwing the tyke out on his ear, he did the next best thing. He sent him over to see Carruthers, the most junior of the English masters. Let him wet nurse the baby and he sincerely hoped he never had the displeasure to encounter this wretch and his shiny suit ever again.


Steve had been at the school for more than two weeks and was on the edge of despair. Carruthers was scarcely older than Steve himself and had not taken well to his task as babysitter. It had brought out his worst bullying tendencies: Carruthers was on the lowest rung of school-mastering and resented it; now, in Steve he had someone who was even lower down the pecking order.

He took an instant dislike to Steve from the moment he opened his mouth. He didn’t care that the new man was a considerable expert on the Romantic poets and Shakespeare’s tragedies: all he heard were his Black Country “strangled vowels.”

Carruthers would have left Steve to fend for himself if he hadn’t been given instructions by Dr Fortescue to “look after” him. Carruthers knew from painful experience that he must obey his headmaster at all times. Failure would mean a second humiliating visit to Fortescue’s study and Carruthers intended to avoid that at all costs.

Steve was assigned Sixth Form English classes, on the expectation that boys were older and responsible and would not make trouble for him. Alas, for poor Steve, that wasn’t to be. The boys might only eighteen year olds, but they were already well versed in snobbery; they knew their own sense of superiority and Mr May was most assuredly not of their class.

The boys went through the formalities: they stood, as they would for any master, when he entered the schoolroom and they called him “Sir”, but they had no respect for him at all and rather resented that he had been foisted upon them.

They called him the Queen of the May behind his back and made assertions that he was “queer,” even though they didn’t quite know what that meant. A particularly obnoxious boy called Jenkins led the charge. Jenkins was one of those boys who thought he was the class clown, and makes himself popular by always making his fellows laugh, but is in fact a bully. He and another boy had made up a poem about Steve that concentrated on the master’s assumed sexual behaviour.

Steve knew none of this but he did know that he had no rapport with his pupils and every class with them had become an ordeal for him.

Things were about to get even more humiliating. Every time he entered the schoolroom he felt he had been transported back two or three decades. The schoolroom consisted of about twenty wooden desks connected together so that pupils sat thigh to thigh on wooden benches. Along the top of the desks ran a groove for the pupil’s pens and pencils and each had an open inkwell.

A master would stand at the class at a blackboard and easel. To his left was a small desk for him to work at and behind it was a shelf for books.

The boys hated Mr May and wanted to make as much trouble for him as possible. Jenkins had made a plan. Each boy would make a paper dart and at a given signal as Steve chalked on the board they would simultaneously bombard him. It worked perfectly – at first.

Each boy surreptitiously tore a page from his exercise book and whenever Mr May turned his back, they would stealthily fold their paper until they had fashioned a serviceable paper airplane.

Then as Mr May was chalking a particularly difficult explanation on the board, Jenkins silently gave the command and a veritable air force of paper flew at the trainee schoolmaster. Some darts hit him about the body (at least one caught him on the back of the neck) while others made crash landings all around his feet.

“What? What? What is going on?” Steve spluttered.

Then, the schoolroom door flew open and Dr Fortescue stormed in. What back luck for the boys that he had been passing the classroom at the very moment the air force took flight and he had seen enough to know the boys were attacking the schoolmaster.

He might not have liked nor respected May, but Dr Fortescue knew it was his own duty to protect him and the dignity of all the schoolmasters at St Septimius from the savagery of their pupils.

The boys stood to attention as Dr Fortescue strode into the room, his face was puce in colour and he was sweating profusely. He seemed to be losing a struggle to retain his temper. The boys were fortunate he was not carrying a cane at the time (he almost always did when he patrolled the school corridors) for he might just have thrashed every backside in the classroom.

“This is disgusting behaviour,” he thundered. The silence from the boys was deafening, hardly one of them dared to breathe. All Steve could hear was the thump, thump, thump of his own heart bursting to get out of his chest. He was so miserable; made so by the boys’ air attack on him and compounded by his headmaster witnessing his incompetence in the schoolroom. He was close to tears as Dr Fortescue glared around the room, catching the eye of every single boy as he roared his disapproval.

“You will all return here at four o’clock this afternoon for detention.” With that he turned on his heels and burst through the door into the corridor, leaving a classroom full of shocked sixth-formers and one deeply humiliated trainee schoolmaster.


Shortly after four o’clock the boys assembled in the schoolroom for their detention. Some might have felt resentful since all the form was being punished for the misbehaviour of a few boys, but they did not show it. Schoolboys have an acute sense of injustice, but on this day they had a sense of solidarity that would made a trade union leader envious. They were united in their disdain for Mr May; if he could keep control of a class they wouldn’t be here now.

Dr Fortescue entered; glared at the class and pronounced. “You will tear a page out of your exercise book and each boy will write a two-page letter of apology to Mr May. I will read your missives and if your apology is not to my satisfaction, I will apply my cane to the seat of your trousers.”

With that he strutted from the room, in search of tea.

The boys started on the task. Two pages? How was a fellow expected to make a letter of apology run for two pages? What was there to say except: “I’m sorry.”

Many of the boys stared into space, chewing the end of their pens, hoping for inspiration. Others whispered to their neighbours as if that might stimulate thought.

Then Jenkins, the class joker, piped up. “Dear Mr May. I am sorry that you are a lousy schoolmaster.”

He was encouraged by the laughter this received.

“I am sorry that you are a tyke, who was born in Wolverhampton,” this said in a mock Black Country accent. The boys were appreciating the joke.

“Dear Mr May, I am sorry you are a homo.” The class was silent. Faces reddened. Jenkins had not expected this. All the boys thought May was queer, that’s why they nicknamed him Queen of the May.

“Jenkins!” Dr Fortescue had returned to the schoolroom, a cup of tea in one hand and his favourite cane in the other.

“Stand up boy!” Fortescue’s face had turned the colour of red wine. Boys of Dr Fortescue’s acquaintance knew this was a dangerous sign. Jenkins stumbled to his feet. Just as blood was rushing to the headmaster’s face, it was draining from Jenkins.

“What is the meaning of this!” Fortescue thundered, but he clearly did not expect an answer.

“Stand out in front of the class.”

Every boy in the room knew what was to happen next. Dr Fortescue’s punishments were always given in front of the class; the unfortunate boy would be called out to the front and given a real whacking. Once it was over the boy would be sent hobbling to his seat, finding it extremely difficult to let go of his stinging cheeks. Without fail he would at least have moist eyes; most would be in tears, even openly crying as they tried to sit down. Dr Fortescue would stand in front of the class with a satisfied smirk on his face watching and still wielding the cane. He would place the weapon back on the desk, in plain view, as a warning to everyone else, should they misbehave.

“Right Jenkins! Bend over the front desk backside facing the class.”

Reluctantly, the eighteen-year-old walked to the desk and bent over and waited for Dr Fortescue to begin. He sensed his grey trousers being tightened as the headmaster ensured they would offer the least protection to his bottom as possible.

Jenkins was no longer the class clown, he was a fool bent over with a class of sixth-formers staring intently at his bottom. The classroom was tense as they all waited for the caning to begin. Jenkins felt the cane tapping his backside and then it was gone. The next thing he heard a swish and his bottom was on fire.

Before he could recover the second stroke had landed, this took his breath away and by the third it was all he could do not to yell as the agony was so intense.

The fourth landed right at the bottom of his cheeks and Jenkins gulped tears. As the final two strokes fell in the same area he could no longer keep quiet and screamed out in pain, broken and humiliated in front of his classmates.

Dr Fortescue liked to examine a boy immediately he had caned him and ordered Jenkins to rise from the desk at once. As tears streamed down the teenager’s face, Dr Fortescue laid into him verbally. “Boy, I have gone easy on you this time, if I catch you again abusing Mr May your trousers and underpants will come down and Six will become Twelve. Is that understood?”

It was, but Jenkins did not have sufficient control of himself to say so.

“Back to your desk and complete your letter of apology.”

Then turning back to the class, Dr Fortescue added, “I shall return in twenty minutes’ time and I expect each one of you to have completed the letter of apology. Any boy who has not done so will get the same as Jenkins.”

With that he left the classroom to the sound of his own footsteps. For the next twenty minutes the classroom was in silence except for the gentle sobbing of one eighteen-year-old boy.


He had only been at St Septimius a short time but nothing could surprise Steve about the school. Dr Fortescue, his headmaster, expected him to bend over and offer up his arse for his cane, just as if he were one of his fourth-form pupils.

To Dr Fortescue it seemed the most natural thing in the world; he was in charge and he would brook no nonsense from this trainee schoolmaster, who had failed in all his duties in the schoolroom. He was utterly incompetent and if he expected a good report for his training officer at the end of his placement he had better get his backside in the air fast.

Dr Fortescue didn’t say any of this out loud, of course, but Steve knew that was what he meant. The only chance he had (and it might only be a slim chance) of becoming a junior schoolmaster was to let this bullying headmaster have his way.

Dr Fortescue opened one of the desk drawers and picked out a small bunch of keys which he carried across to a tall cupboard on the far side of the room. The cupboard was like a wardrobe with a metal rail running from side to side and there was a black schoolmaster’s cloak and an overcoat hanging from it on coat hangers. Then to one side, Steve saw several canes also suspended from this metal rail. They seemed to vary in length by only a few inches and one or two were thicker than the others.

“Very well, go to the cupboard and choose a cane and bring it to me.”

Slowly, Steve went over to the cupboard and looked at the array of canes inside. He looked back at Dr Fortescue questioningly. “The one you think you deserve.” he repeated. Finally, Steve took a breath and chose the thickest one, which was second longest. He held it almost reverentially as he passed it to his master. It was heavier than he thought, but easy to hold. Despite its thickness, it was very pliable.

Fortescue moved a high-backed chair from the corner of the room and set it down in front of his desk.

“Stand there.” It was a clear command as Dr Fortescue pointed to a spot on the rug. Steve shuffled his feet, reluctant to move, but deep down he knew he had no choice. For the sake of his future he had to be completely subservient to Dr Fortescue and anything the headmaster demanded of him he had to deliver.

“Trousers and underpants down.” Another cool command, delivered as if the instruction was the most natural thing in the world: a twenty-two-year-old trainee school teacher required to strip half naked to allow a man more than twice his age to flog his buttocks with a whippy rod.

Hesitatingly, Steve started to undo the belt of his trousers and then his trouser buttons. He half pushed and half pulled his suit trousers down just below his bottom.

“That’s no good boy. I want them down round your ankles.”

Steve blushed and pushed his trousers right down. He then seemed to freeze.

“Now your underpants,” Dr Fortescue gently reminded him. “Right down please.”

Steve summoned up the courage, grasped the waistband of his pants and in one slow, but steady movement, drew them down to meet his trousers. He had a long-tailed shirt so that action did not reveal his buttocks, other than a brief glimpse of the very lowest part.

“Please pull your shirt up so that your bottom is fully exposed.”

Steve obeyed pulling his shirt up and gathering it at the front. His bottom was round and pert.

“Bend over the chair boy,” he ordered, rattling through his rules for caning. “Head right down, I want you tight, bottom out more, legs slightly apart, hold the chair seat tightly. And stay there. If you move out of position I shall give you extra strokes.”

Steve bent with his legs stretched out at forty-five degrees behind him. The seat of the chair was cold to his hands. He could feel the back of it sticking in to his stomach. He felt very frightened.  He could hear a cane being swished. Then footsteps moving towards him. He felt intense embarrassment. He shut his eyes and gritted his teeth. This was going to hurt!

With a growl, Fortescue swiped the rod through the air and landed it with a heavy thwack across Steve’s bottom, pacing each stroke for maximum effect, giving him the full length of the cane and making sure that twelve strokes covered the whole of his bottom.

“Ow! Ow!” shrieked Steve, moving his bottom from side to side over the back of the chair as he tried to alleviate the sting, but the stick whipped and cracked to Dr Fortescue’s delight, dancing on his bare cheeks and painting pink stripes. His buttocks rocked from side to side as Steve wiggled his hips frantically, attempting to dissipate the pain.

The trainee teacher begged the headmaster for mercy as Dr Fortescue lashed his cane into his tight buttocks. His behind was throbbing with the pain of twelve strokes of the cane, but Fortescue wasn’t satisfied.

Suddenly, Fortescue stopped swiping his cane and began dementedly slapping his hard, rough hand into Steve’s welted buttocks. A rapid succession of sharp whacks covered almost every part of young Steve’s bare backside and upper thighs, leaving him panting noisily for breath and gulping back a flood of cries. He was sweating profusely, and his breathing was heavy, fast, gasping. His face and neck were red and strained and his mouth agape.

Dr Fortescue’s breathing was heavy, excited, uncontrolled. Then he stopped spanking Steve’s red-raw buttocks.

Steve could not be sure his punishment was at an end as he assumed Dr Fortescue would instruct him to stand when he was finished. When no instruction came, the twenty-two-year-old drew a deep breath and exhaled slowly and tentatively raised his head up just ten or twelve inches.

When he was not stopped, he took another deep breath and stood half upright, his hands gripping the top of the chair. Finally, he stood up on tiptoe and began gently exploring the damage caused to his bottom, trying to disperse the sting. Several tears trickled down his cheeks and he wiped them away with the back of his hand.

Dr Fortescue was motionless, Steve could not be sure, but the headmaster appeared to be in some kind of trance.

With a sharp intake of breath, Steve bent down and slowly hunted through the material that lay around his ankles as he sought the waistband of his pants. With a slight groan as he experienced once more the soreness of his bottom, he eased them up his legs. Equally as slowly he pulled up his trousers.

Dr Fortescue was battling to regain his composure, but failing. Steve started to run on the spot and jump up and down to help relieve the pain. Football commentators on TV are always talking about how players “run off” their injuries after they’ve been kicked about a bit on the pitch. In Steve’s case, it didn’t seem to work.

Seemingly lacking the power of speech, Dr Fortescue pointed to the door and whispered, “You had better go.”

Picture credit: The Magnet


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The Tyrant Headmaster 7: The field trip

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For previous episodes of The Tyrant Headmaster, click here

Mr. Tyler, the geography master, did not like it. Not one little bit. He was nearing retirement age, he didn’t want change. What couldn’t things be left alone. He was too old to learn new tricks.

“What’s up old man,” Jessop of History handed Tyler a cup of tea. “Why so glum?”

Tyler took the cup and sipped. “Urghhh.” It was lukewarm and stewed. With an unsteady hand, he put it down on the table.

“Field trip,” he wailed, and as if that was sufficient explanation he turned the pages of the Daily Express in search of the gossip column.

“And …?” Jessop was always amused when old Tyler had a bee in his bonnet and he wasn’t about to let the chance of some fun escape.

“There was a time when geography was all about capital cities and Norwegian timber exports,” Tyler groaned. “Now, it’s rivers and mountains,” his face contorted into a sneer, “and glaciers.”

Jessop grinned. “Ah, the new examination curriculum. So, what is it a fieldtrip?”

“The bloody Lake District,” Tyler spat out the words. A trip with the Upper Sixth Geography set. What in the world, he wondered, could be worse than that?

“Never mind old chap,” Jessop chortled, “think of it as a holiday.”

Tyler’s already ruddy face turned puce. “Holiday!” he roared. “It’s the Lake District, it’ll be cold, grey,” and he shuddered, “very wet.”

The boys took the news more cheerfully. They would be at an educational field centre; a schoolroom in the mountains. Any distraction from their dreary, mundane lives would be mightily welcomed.

“Do you think there will be girls there?” Jay Collins feigned indifference. His lack of access to the fairer sex was getting him down. Did masturbation really make you go blind? He hoped not, otherwise he would soon be walking with a white stick.

“One track mind, Collins” Bob Lender grinned. “I’m sure the Windermere Field Centre is really a hot bed of vice. Mountain treks by day, orgies by night. Cherries will undoubtedly be popped.”

Collins blushed. He hated it when the boys teased him. Was he really the only virgin in the Sixth-Form?

If there were girls at the field centre the boys never found them. Proprieties of the day ensured that boys-only schools visited one week and the girls another.

“Hard luck Collins,” Lender chuckled when the awful truth was revealed. “It’s back to the four-fingered shuffle for you.”

“Hey guys, guys!” Bertie Price rushed into the dormitory, breathless. He had news to impart. He loved it when he knew things that the others didn’t. “Guess what?”

Six eighteen-year-old boys groaned. It was going to be like a number of the Twenty Questions wireless programme.

“Animal, vegetable or mineral?” one squeaked.

“Animate or inanimate object,” another groaned.

“Well, if you don’t want to know?” Price sniffed, “Then I shan’t tell you.”

“Get on with it Pricey, you know you’re dying to tell us,” Lender genuinely did not care to hear but he wanted the pest to shut up.

“St. Tom’s,” Price was breathless. “They’re here.”

There was no need for further explanation.  He meant that a group of sixth-formers from St. Tom’s, a school housed in the locality of St. Septimius, were also resident at the camp.

The rivalry between the boys of the two schools was intense. St. Tom’s was an elite “public” school for the sons of the higher classes. St. Septimius, as an “Independent Grammar” was considered to be one rung below in the pecking order. Such social class distinctions were important in England. The boys of St. Septimius thought themselves the equals of their rivals in every way, but the chaps at St. Tom’s begged to differ.

“Well boys,” Lender stretched, “We need to devise a plan.”

The field centre was not so large that the chaps from St. Tom’s did not discover the existence of their rivals. They set about drawing their own campaign of action. It would have to happen at night. When everyone was in bed, they would have the centre to themselves. St. Tom’s was a boarding school; the chaps were well versed in japing after lights-out. A dormitory raid! They would climb in through the window, take the oiks from St. Septimius by surprise, rough them up a little, and steal their pillows for souvenirs. That would show them who was the boss.

Mr. Tyler was settling down for the night when he heard the first mysterious sound. It was excited voices. Somebody was out of bed. He glanced at his alarm clock; it was nearly ten o’clock, fifteen minutes after lights-out. Could it be burglars? Surely not; the education centre was remote and the nearest village was five miles away. It wasn’t his business, he thought, the centre had its own manager and caretaker, let them sort it out. He wrapped his dressing gown around his body; the dreadful room they had given him was draughty and he hadn’t been properly warm from the moment he had arrived.

The chaps from St. Tom’s didn’t get it all their own way. Their plan had leaked (there’s always one sneak at school) and when they clambered through the window they were greeted by a welcoming party. It is an old prison trick to take a towel and tie it in knots to make an effective weapon. This is especially so when it is whirled around the head at speed before connecting with the body of its target.

Biff! Bang! Bosh!

“Ouch! Gerroff! Yaroo!” the cries from the chaps at St. Tom’s were pitiful.

“Get that one with the specs!” Bob Lender was having the time of his life. “Give him what for!”

A knotted towel sent the spectacles flying, an ugly red mark instantly spread across the young man’s face.

“Oooofff” Another chap got a whack right in the belly. He sank to his knees, gasping for air.

Mr. Tyler heard none of this; his boys’ dormitory was some distance away. His peace was disturbed by a furious hammering on his bedroom door.

“Mr. Tyler, Mr. Tyler, please open up.”

The geography master recognised the irritated voice of Mr. Boston, the manager.

“Coming man, coming. Stop that infernal knocking,” Mr. Tyler was equally irritated.

He opened the door to be confronted by a red-faced, portly man. He wore a long mackintosh over his pyjamas.

“There’s been a riot,” he spat the words. “Your boys ….” He waved his arms about frantically. “I’ve never seen anything like it in all the years I’ve been here.” He added hysterically, “It’s a disgrace.”

It took some time before Mr. Boston calmed sufficiently to tell the story. Mr. Tyler listened, at first impassively, and then with mounting anger. When he was told about the smashed spectacles and bruised bodies, he became furious.

“Damn and blast!” he bellowed. He had known this trip would be a disaster. Why had he agreed to come? He took a huge deep breath, but it did nothing to control his anger. Boston was correct; his boys were a disgrace. They had let themselves and the school down. More importantly, they had humiliated himself. There could be only one recourse to action.

“Do you possess a cane by any chance?”

Mr. Boston looked blank, as if he hadn’t understood the question.”

“A cane, man,” Mr. Tyler had lost none of his fury. His arm rose and fell, imitating a cane as it swished through the air.

“Oh, sorry. No,” Mr. Jessop flushed at the image of eighteen-year-old schoolboys touching toes and being caned on the seat of their pyjamas. It’s what the blighters deserved, he thought. Out loud he said, “We rather leave that sort of thing to the schools.”

“Mmmm pity,” Mr. Tyler’s brows knitted. Corporal punishment must be administered, of that he was in no doubt. He sat on the edge of his bed and slipped his bedroom slippers on his feet. “Please take me to them, Mr. Boston.”

He found a subdued group of sixth-formers, sitting on beds, silently contemplating their fate. They stood as Mr. Tyler entered the dormitory. He glared around the room and then stared intently at each miscreant. Many of the teenagers could not meet his eye.

The schoolmaster’s fury had not dissipated. “Stand by your beds, all of you.” Soundlessly, they shuffled into position.

“Thank you, Mr. Boston, I think I can take it from here,” he nodded at the door. The centre manager’s glum look did not mask his disappointment.

Mr. Tyler turned his attention once more to the sixth-formers standing miserably before him. What possessed them to behave like small children. Each one of them was clearly a young adult. Several in the room would need to shave their beards before breakfast time. The baggy pyjama bottoms they wore did little to disguise the presence of genitalia.

He jawed and jawed them. “A disgrace to the school.” “Your parents would be ashamed.” “What would the headmaster say when he found out?” The sixth-formers took it with mounting embarrassment. This episode could end in only one way.

“Well, if you insist on behaving like small boys, you cannot complain if I treat you like small boys.” He picked up an old wooden straight-backed chair and set it down in the middle of the room. A dozen pairs of eyes burned into him as he sat, stooped down to remove a slipper from his right foot and spread his legs a little.

No boy dared look him in the eyes; had they done so they would have detected an unreadable gleam. The schoolmaster squeezed the bedroom slipper in his right hand before waving it in the general direction of the boys. “Lender, you first. Come here and bend over my knee.

“Oh, no, Sir.”

“Please, you can’t, Sir.”

“We’re sixth-form, Sir.”

The protests were predicable. Mr. Tyler cut them short.

“Would you rather I reported you to Dr. Fortescue? I am sure he will take a dim view that you have disgraced the school so publicly. I have no doubt he would convene a special school assembly to deal with you.”

He would do. Every boy in the room had no doubt at all about that. A public thrashing. Maybe even followed by suspension. No, matters had to take their course; this night, in the dormitory.

“Step forward, Lender.”

The eighteen-year-old’s face reddened. He had no choice. He must take a slippering. But, over the knee? That was just too humiliating

“Can’t I just bend over the end of the bed, Sir?” he implored.

“Pah! Don’t be absurd boy. If you want to behave like you are in a nursery, you must face the consequences.”

Lender shuffled forward. Bend over his knee? How was this done, exactly? Mr. Tyler was a shortish man and Lender was probably eight or nine inches taller. He stood to the schoolmaster’s left and looked down at his knees; they seemed a very long distance away.

“Come on boy, we don’t want to be here all night.”

Landers bent his own knees and leaned forward. He put his hands on the schoolmaster’s legs and eased his body down until his stomach rested on his bony legs. His own legs stretched behind him so his toes rested on the ground. He reached forward and placed the flat of his hands on the worn floorboards. He couldn’t see it, but his bottom rested at a forty-five-degree-angle ready to receive a spanking from the schoolmaster’s slipper.

But, Mr. Tyler was not yet ready. He had promised a “nursery” spanking and that was what he was going to deliver. An audible gasp echoed around the room when he gripped the waistband of Lender’s pyjama bottoms and tugged them, once, twice and three times until the teenager’s bottom was completely bared. Lender wriggled in protest, but the old man pressed his arm into the boy’s back. He was going nowhere. The movement sent the pyjamas slithering down his thighs until they came to rest at his knees. He was naked from his knee hollows to the small of his back.

Every boy in the room had a perfect view of his hairless bottom. Mr. Tyler, should he chose to, could see right into his crack. Nothing in Lender’s past life had been so humiliating. Not even the time he was caned bare-arsed in the headmaster’s study. Poor Lender soon found the slipper had a bite of its own, a stabbing ache rather than the vicious agony of the cane. The pain was slower to build up, but it did so nevertheless. The big supple slipper stung like crazy. Mr. Tyler spanked Lander’s bottom from side-to-side and up-and-down. His bottom was turning scarlet and his teeth were clenched and his eyes squeezed shut but his backside had not moved one inch.

“Up.” The spanking was over. For Lender, but not for Mr. Tyler. “Price. You next.” Over the next thirty minutes the old man put every sixth-former in the room through their paces. It was a very tired schoolmaster who retired to bed later that night. But, he slept the sleep of the Just.

Across the education centre grounds, six eighteen-year-olds took turns to lower their pyjama bottoms and bend over a bedstead for a searing six lashes of a Malacca cane administered on the naked haunches by an irate master. He had come on the fieldtrip prepared: St. Tom’s was after all a school for the sons of gentlemen.


Picture credit: The Hotspur



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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.


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The Tyrant Headmaster 4. Smoking on Saturday

The Tyrant Headmaster Dr Fortescue has set about taming his sixth-formers. Episode one is here. Episode two is here. Episode 3 is here

cane (35)

“Bend over.”


“Touch your toes boy.”

Mike Upton really resented this. He was in his housemaster’s study preparing to take six-of-the-best and he hadn’t broken any rule.

And he was eighteen years old, dammit.

Mike and his sixth-form pal Barry Turner had been seen smoking cigarettes in town on Saturday afternoon. Saturday afternoon. They weren’t at school. They weren’t in school uniform. They were on their way home from the cinema and smoked a cigarette.

So what! This wasn’t a boarding school, Mike thought, what he did at the weekends was his own business.

The legal age to smoke in this country was sixteen. Mike was eighteen. He was an adult for pity’s sake.

But, Mr Alderson, like all the masters at St Septimus Independent Grammar School was a law to himself. It didn’t matter that Mike was an adult and could legally smoke and that he wasn’t at school, nor was he on his way to or from it.

Someone reported them to the school; Mike had no idea who that was. Why on earth would anyone do such a thing? Who would be bothered?

The word got to Alderson and that was that. As far as he was concerned the good name of St Septimus Independent Grammar School had been tarnished and that was all that mattered.

The boys could not be allowed to damage the reputation of St Septimus. Something had to be done to stop any repeat offence. A sharp caning would suffice.

Mike could not believe it when his form master had told him the report to the housemaster. There were jeers from classmates as he rose from his desk to leave the room. A summons usually meant only one thing: the boy was to get a bowing.

Mike was puzzled, he knew he hadn’t done anything to deserve a caning and was confident he was in no trouble.

So, he was astounded when Alderson confronted him about the smoking incident, lectured him for a few moments and announced a caning was to be administered.

Mike could only babble that it wasn’t fair, but Alderson was allowing no argument.

Mike didn’t know what to do, the situation was absurd. How could the housemaster want to beat him on the bottom for breaking a non-existent rule? He wanted to argue but instinctively knew it would be no good. The masters were the law here and if they wanted to cane Mike that was the end of the matter.

An alternative flashed through Mike’s mind. He could tell Alderson to “stuff it” and walk out the door. What Mike didn’t know was that’s exactly what Barry had said (well, not in exactly those words) half an hour previously. He was now at home contemplating the expulsion from school that would inevitably follow.

Mike was a pragmatist. A-level exams started in two weeks’ time and he couldn’t afford not to follow Alderson’s order.

Would a caning be so bad?  Wouldn’t it be over in thirty seconds? Would it hurt so very much? Probably it would, but it wouldn’t kill him, he thought.

Mike had never been caned. That would be unusual for a pupil at St Septimus where corporal punishment was widely used, but he had only joined the school last year when his family moved to the town.

Alderson walked the length of his study to a tall thin corner cupboard. He extracted a small key from the pocket of his waistcoat, unlocked the cupboard door and quickly extracted a whippy cane from within.

He turned to face Mike, who was witnessing the housemaster’s movements upside down, watching through his own outstretched legs.

Alderson took a few practice swipes with the cane as if to get its measure. It whistled as it sped through the air, sending shivers through Mike. As school canes go it wasn’t especially vicious. It was a little over three feet in length, and as thick as a pencil and had the traditional curved handle.

He grasped the cane with one hand below the handle and the other at the furthest end. Thoughtfully, he flexed the rod between his hands.

Mike was now in the required position. Legs apart, knees straight, fingers touching the toes of his shoes. Alderson eyed the boy’s backside. The grey trousers had stretched across Mike’s buttocks so tightly the outline of his Y-front underpants were clearly visible.

The housemaster lifted Mike’s blue-and-white blazer clear of the target area and prepared to start the thrashing.

“Brace yourself! I shall make these hurt, boy. You don’t dare let go of your toes if you know what’s good for you. If you move out of position, I will give you extra strokes.”

Alderson tapped with his cane as he took aim, raised it high in the air and then lashed it down to land with a thwack high on Mike’s bottom.

Mike was conscious of the cane patting his bottom. It disappeared and then landed, followed, after a brief interval, by an overwhelming sting.

“Oww! Gosh, oww!” Mike gasped, trying to keep his scorching bottom still after his first-ever stroke of the cane.

The cane tapped again and then with a swoosh! it landed in the same place as the first.

“Ow! Ow!” gasped Mike, moving his bottom from side to side as he tried to alleviate the sting. It took a lot of resolve for him to remain in position.

It hurt horribly. The stroke cut across his buttocks like a knife. He could have sworn he was bleeding.

Once again the cane sizzled across Mike’s upturned rear.

He cried out between gritted teeth. His back arched, his eyes closed and his face screwed up in pain as he felt the effect of the harshest blow yet. Tears were starting at the back of his eyes.

Then the rod whistled through the air and landed with a heavy thwack across the lower bottom where the cheeks meet the thigh.

His buttocks rocked from side to side as he wiggled his hips frantically, attempting to dissipate the pain.

Mike’s whole body tightened as the next stinging lash cracked across the soft mounds of his backside.

He waited for the final crack which was angled across the bum, crossing about three of the others.

After a half dozen strokes Mike was amazed that there was this much pain in the world: it didn’t seem that anything could hurt so much.

“Stand up boy.”

His behind was throbbing with the pain of six strokes of the cane.

Mike drew a deep breath and exhaled slowly as his head came up just ten or twelve inches. Another deep breath and the boy stood half upright, his hands gripping his knees. Finally, he stood up and his hands went to his bottom and he stood on tiptoe as he tried to disperse the sting. There were tears running down his nose.

“That concludes your punishment, Upton. I hope you have learned your lesson.”

Mike, still struggling to catch his breath, said nothing. It was a sickener to hear the housemaster, especially when he knew in his heart he was innocent.

Mike went painfully towards the door, paused and turned to look at Alderson, who had his back to him as he made another entry into the punishment book.

The throbbing in Mike Upton’s backside had subsided, but his indignation had not: who the hell did Alderson think he was? What right did he have to make him bend over and touch his toes so the pervert could lash a cane into his tight buttocks?

Mike sat on his bed. He had inspected the six dark red welts on his bum. He didn’t know what marks a caning was supposed to leave behind: he had never been caned before, nor had he seen the bum of a boy who had. Even so, he felt sure Alderson had probably laid it on with some vigour. The marks would remain for many days at least.

The pain had gone, but an ache returned when he sat down on a hard surface. He had winced when he sat down on a wooden chair at dinner time. He hoped his mum and dad hadn’t noticed his discomfort.

It was getting late; he had finished his homework and he lay back on his bed staring at the ceiling and stroking his todger. Jesus! he thought, a caning! The housemaster had caned him, an eighteen-year-old man. The reality of it just could not sink in.

He wondered about his friend Barry Turner. Mike now knew that Barry had refused to be beaten and had been sent home. It looked like he was going to be expelled. Bloody Hell, with only a couple of weeks to the exams, Barry must be crazy; why didn’t he just bend over and get it over with?

In the distance a telephone rang. He heard his mum answer it, followed by her footsteps as she approached his bedroom door.

“Mike, Barry is on the phone for you.”

Ten minutes later they were sitting in the bar of the King’s Head, each nursing a Double Diamond.

Mike wanted a cigarette, but since his caning he dared not light up. Who was it who had seen him and Barry on Saturday and why did they report them to the school? He felt he couldn’t trust anyone now, was he being spied on, even here at the pub? He had forgotten that if he could be beaten for smoking out of school, he could also get done for being in a pub.

The boys sipped at their beers. Mike waited. He knew that eventually Barry would tell him why he invited him out.

It was about school, of course.

“The letter said I would be expelled unless I went into school tomorrow and subjected myself to corporal punishment,” he said.

“Subjected myself to corporal punishment,” this time he sneered the words.

Mike was relieved. He hoped Barry would see sense and not ruin his chances of a university place.

“It wasn’t so bad,” he lied, referring to the caning he had received earlier it the day. In fact, it had hurt like Hell and, perhaps more than that it had injured his pride.

“What did your mum and dad say?”

“What did yours say?”

“I didn’t tell them. What’s the point?”

“My dad went mental. He said if I don’t go back to school, he’ll kick me out the house.”

Mike’s face betrayed his shock at the news.

“He doesn’t mean it, but it’ll be murder at home if I don’t.”

“Do it mate. Do it,” Mike was surprised by his own bluntness. “Go back to school, show Fortescue your arse, take your whacking and then tomorrow night you and me we’ll go out on the lash and get rat-arsed!”

Barry wouldn’t admit it, not even to himself, but that was what he wanted to hear: his friend telling him to go back and face the music. The thought of expulsion filled him with dread, even more than the knowledge that the thrashing he was going to get would be ten times worse than Mike’s. He knew Fortescue’s reputation: he was a vindictive sod and he would make Barry pay for his rebellion.

He took a long gulp of Double Diamond, “OK. I’ll go see the good doctor tomorrow for a tanning.”


It had been a fine early summer’s day and now with the time approaching 4 p.m., the sun shone into my study. Any minute now Barry Turner would be knocking on my door, ready to submit to my will. I had already decided I would deliver an exemplary flogging. I was no longer concerned about his original offence: boys a lot younger than Turner smoked. They knew it was against the rules and if they were caught they were beaten.

My concern now was the boy’s refusal to accept his deserved chastisement. He had stood up against his housemaster. It was wilful disobedience and that could not be tolerated. I had contemplated flogging him in front of the whole school. I very much wanted to do this, but I have in recent times become concerned about the bad publicity schools have received in the newspapers.

So, to avoid a bad press, I had decided to flog him in private: but I intended to deliver the most severe thrashing of my career. Of the many hundreds of canings I had administered over the years none would have been as awesome as this.

Exactly at 4 p.m., I heard a tapping on my study door. He had arrived.

“Enter,” it was a quiet command I did not intend to engage in histrionics.

The door opened and Turner entered. I have to record that he had made an effort with his appearance. His blue-and-white blazer was neatly pressed; his white shirt looked as if it was ready to star in a soap powder commercial. His dark grey trousers had creases so sharp they might cut you.

He was nervous as well he might be. He must have known that he would never forget this day no matter how long he lived.

I pointed to a rug in front of my desk. “There boy.”

He shuffled into position.

“I believe you have something to say to me.”

He had been instructed to offer me a formal abject apology. I intended to humiliate him: I would not allow him to believe he could get the better of me.

I put on my best blank expression as he launched into his prepared speech.

He spoke for about twenty seconds, staring intently at his shoes before he dried up.

“Is that all?”

What little colour he had in his face drained away.

“I am so very sorry for smoking in the street and I apologise most humbly for not submitting to Mr Alderson’s punishment.”

That was better.

“What would you like me to do now?” I asked.

He looked confused and lapsed into silence.

“What would you like me to do now?”

More silence. Turner had not expected this development.

“Would you like me to thrash you?”

His hands were shaking so much he clasped them behind his back to steady himself.

“I insist that you say it.”

He looked at me seeking pity, but I had none to give him.

“Say it.”

I could see him composing a few words in his head.

“Would you cane me.” Then as an afterthought he added, “Please.”

“No boy. That is not enough. You must ask that I thrash you on your bare buttocks as hard as I possibly can.” I was enjoying this very much indeed.

His breathing was shallow and I suspect all the saliva had by now drained from his mouth, but he managed to cough out the words.

“Would you beat me hard on my bare buttocks.”


He was petrified.

“Would you beat me hard on my bared buttocks, please, Sir.”

He repeated the words to my satisfaction.

“Of course, I shall.”

I moved across my study to the cupboard where I keep my canes.

“Hang your blazer on the door.”

While he did this I moved an armchair round, so that its back now faced the centre of the room.

I swished the cane through the air a couple of times and then held the two ends and flexed it gently testing it for whippiness. It curved nicely in my hands.

Turner turned to face me once again, eyeing with dread both the cane in my hands and the armchair.

“Turner when I cane I make sure it hurts. There is no point in giving you a beating if it doesn’t. Your backside will be on fire and you will be sore for a few days. The marks will last about two weeks but you will live. You will not return for another beating and will learn from this experience.”

He mumbled something that I couldn’t quite hear and before I even ordered him to take down his trousers and underpants, tears were flowing down his face.


Dr Fortescue stood as I began to unbuckle my belt. I unzipped and let my trousers fall to my ankles. Putting my fingers in the waistband, I peeled my underpants down letting them fall on top of my trousers.

Dr Fortescue swished the cane through the air. If his intention was to intimidate me, he had succeeded.

“Bend over the chair,” he touched the top of the armchair with the cane for emphasis.

In terror I bent forward; my bottom, a little wobbly when I was standing, tightened into a smooth curve. My bare buttocks were presented submissively over the back of the armchair, my trousers and underpants bunched around my ankles.

“Head nice and low please Turner.”

My thigh muscles and bottom tensed as I stretched my arms out grasping the armchair’s cushion at the front. I felt Dr Fortescue lift my shirt from my backside, exposing me, both to his eyes and to the air of the room. My body was naked from the middle of my back to my ankles. This made me shiver slightly; not with cold so much as fearful anticipation.

“Keep very still, boy and push your head right down into the cushion.”

I pushed myself further down into the chair, raising my bottom well up for the cane.

“Don’t forget, Turner, don’t move around too much or you will get extra strokes.”

“Yes, Sir,” my reply was muffled as my head was buried in the chair cushion.

Seconds seem to pass. I was feeling very vulnerable as I imagined him eying up his target and I fidgeted my legs. Suddenly there was an enormous noise. The sound of the cane landing on my backside echoed round the room. I hardly had time to recover from the shock when there was another crack which this time was immediately followed by an intense burning pain. I held my breath as the next stroke landed causing the pain to increase in a sickening wave.

Number four stuck and I let out a whine. Dr Fortescue continued, determined to make me pay for my rebellion. Three more strokes landed, each one lower than the previous, yet all in a one-inch band on the lower half of my bum.

As the next stroke cracked across my poor sore seat I let out a roar, any restraint I may have had was gone. I could no longer see the chair for the tears filling my eyes.

I closed my eyes and gritted my teeth and hung on to the chair. I was aware of nothing except the pain burning like a furnace in my bottom.

Raising his arm high Dr Fortescue brought the cane down with a full swing, landing in the middle of my bottom. I cried out and tossed my head, swaying for a few moments.

The next three strokes seemed to merge together. I was concentrating on staying bent over, in so much pain, and trying without success to stop the tears that were by now flowing down my cheeks.

I desperately wanted to but I did not stand up. Instead I remained bent over the caning chair offering my bottom for the next stroke. I was completely at the mercy of the headmaster, who could make each stroke as severe as he wished and I would have to accept it and then wait for the next.

He swished in yet another stroke across the very centre of my bottom. Though I still stayed over the chair, my feet beat a frenzied dance, and my hips twisted and squirmed.

The caning seemed to go on forever, but finally I heard Dr Fortescue walk over to the cupboard and replace the cane. I felt a terrific sense of relief that it was over but I remained across the chair, breathing heavily and in great distress.

Dr Fortescue gave me time to recover a little. “It’s over. You can get up now. I think you have learned your lesson, haven’t you?”

I slowly pushed myself back on my elbows as I got unsteadily up. My legs felt weak and I had to lean on the chair before I really got my balance. Tentatively at first, I touched then carefully clasped my raw and ravaged buttocks and began kneading them, as though I could somehow squeeze the pain out.

Slowly, painfully, I pulled up my underpants and trousers. I was more or less in control of my feelings now, and was massaging my injured rump as vigorously as I could, still trying to rub away the pain.

Dr Fortescue slipped his arm around my shoulder for an instant, before propelling me towards the door, where I collected my blazer. He opened the door and pushed me out into the hallway. My eyes were still wet and blurry, but I found my way to the toilet where I stayed for a few minutes until I’d regained some composure. I cried a bit more; my bum was throbbing madly and the pain was killing me.

I limped out of the school gates and walked through the streets in a trance. I caught a bus that would take me home, hoping the driver would not ask why I was standing when so many seats were free.


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Charles Hamilton the Second

The Tyrant Headmaster 3. The prefects’ reckoning

The Tyrant Headmaster Dr Fortescue has set about taming his sixth-formers. Episode one is here. Episode two is here.


Bob Lender looked down at the seat cushion inches in front of his face. It was patterned in greens and browns. Autumnal colours.

He concentrated carefully. He needed to focus on something. Such as the large, round, greasy, indentation. Hundreds, possibly thousands, of posteriors had contributed to the dent. It was an old chair. It had seen much action.

He gripped the cushion edge tightly. Waiting.

His heavy grey trousers were at a puddle at his feet. His grubby off-white underpants hovered at his shins. His school shirt was bunched at his shoulders, neatly tucked away from the target area.

He couldn’t have felt more self-conscious. Embarrassed. Humiliated, even. His bare buttocks were on full view to the room.

He was not alone. Tony Brown and Keith Green stood facing the bookcase; hands on head. Waiting their turn.

A cool gust of wind brushed his naked haunches. The study window was slightly ajar. The sounds of schoolchildren talking, some laughing, wafted in on the breeze.

He could feel the headmaster’s cane pressing into his flesh. Dr Fortescue was finding his spot. Taking his aim. Preparing himself. It would be any moment now.

The previous day

The prefects shuffled into the room. Dr Fortescue and his new regime had been the talk of the whole school, from the lowliest junior to the most senior School Captain. The headmaster was a “new broom” and they were to be his sweepings.

There were sixteen prefects in the school and each eighteen-year-old boy made it his business to arrive for the meeting with the Beak on time.

They rose respectfully from their seats when Dr Fortescue burst through the door, his gown flapping behind him.

They looked with interest and curiosity at the man who had taken the helm of the school and who had already started to make trouble.

He was an elderly, tall, grim man, but he stood erect. He looked to be as strong as a mule. He had shown as much when he whipped Rodriquez the day before.

He was not a man to be trifled with. He would not budge a single inch out of his way. He was not to be resisted.

His icy gaze was fixed on the prefects. “I am your new headmaster and the school governors have asked that I make changes,” he spoke in a steady monotone. The “ham actor” had been put on hold.

“I find there is a great amount of slacking and idleness in this school. I am going to make great changes in that respect.”

He stared hard at the boys. They were easily intimidated. None was brave enough to return the stare.

But there was an audible groan, from somewhere near the back of the room.

“What was that? Who made that noise?”

There was no reply.

“The boy who uttered that sound is commanded to step out. Show yourself!” he thundered.

Still no one stirred.

“Who was it!” Dr Fortescue could feel a panic rising. Was this a rebellion? Were the prefects about to turn on him?

“I order the boy to stand!”

The order was not obeyed.

Dr Fortescue could not lose this battle. If the sixth-form could not be controlled, his time at the school would be a failure.

“Very well,” he said menacingly, “I order the boy sitting next to that boy to point him out to me.”

The gasp was audible.

No boy could ever split on a fellow. It was impossible.

Dr Fortescue grew crimson with anger.

“This is obviously an organised conspiracy to show disrespect to your new headmaster. For this disrespect I shall punish you all.”

Sixteen teenagers could not disguise their astonishment. But, there was worse to follow.

He paused for dramatic effect. “The whole prefect body will attend at my study this afternoon at four o’clock and I shall cane every boy.”

He swept up his academic gown. “That is all for the present.”

And, he exited the room, leaving behind a room full of bewildered prefects.

Only when left alone could they express their indignation.



“Can he do this?”

“We’re the Sixth-Form.”

“I don’t think we should stand for it,” Keith Green piped up.

“What can you do?” Bob Lender asked.

“Nothing much,” was the general consensus.

“We’ll see about that,” Tony Brown huffed indignantly.

“You’d better not let the Beak hear you,” a boy at the back said.

There was a great deal of angry talk about it, but when it came to the actual point of refusing to go to the headmaster’s study, most of the prefects caved in.

Four o’clock came around too quickly for the prefects.

“Come on,” Dave Axford, who had an eye on the vacant School Captain’s badge, said, “We’d better get on with it. We don’t want to keep the Beak waiting.”

“Yes, come on,” Bertie Price agreed. “But Axy, you’re going in first,” he smiled.

The prefects formed a crocodile and almost marched upon the headmaster’s study. But, this was no belligerent protest; the boys had acquiesced to meekly accept their canings.

Dave and Bertie led the way. The prefects settled themselves. But they were still indignant. A caning; at their age. It was unheard of. Many wished to God their parents, or worse, their brothers, never found out. It was humiliating enough to be beaten without the world and his wife knowing about it.

Axford wrapped his knuckles on the door and dragging Bertie with him, both boys fell into the headmaster’s study.

Dr Fortescue had prepared. He had several thin canes lying across his desk top in readiness; in case one split during the prolonged beating he intended.

His hard cold eyes fixed on Axford.

“I shall give you four strokes each. Hold out your hand.”

Axford hesitated. Only juniors were caned on hand. What was this blasted Beak trying to say? He and his fellows were expecting at least “six-of-the-best” across the backside. They had all talked about it and agreed it would be a “result” if they were allowed to keep their trousers on.

Gingerly, the prefect held out his hand.

Dr Fortescue rose to the occasion. He measured the distance with a keen eye and brought the cane down with a sharp slash.

Axford’s jaw set hard. He held back the cry of pain that rose to his lips. But only just.

The headmaster watched him with an unpleasant eye. Slash. The second landed. Axford’s ruddy face turned quite pale.

“Other hand.”

The punishment was repeated. Axford bent double like a penknife as tingling pain shot from his palm up and down his arm.

He resisted the temptation to kick the headmaster in the shin as retaliation.

He didn’t. Instead, he quietly left the study.

Price raised his hand for the kiss of the cane. Swipe! The yowl that escaped from between Bertie’s lips was terrific. So were the three that followed.

“Go!” Dr Fortescue barked. “Send in the next boy.”

None of the prefects was keen to take his place. But, that afternoon the headmaster caned thirteen of them.

Dr Fortescue might be new to the school, but he knew how many prefects he had. Three were missing.

The next afternoon

The three eighteen-year-old prefects had intended arguing that sixth-formers could not be caned. It was unheard of. But the headmaster had already proved them wrong on that. Where else could they retreat?

“But we’ve done nothing wrong, Sir,” Keith Green protested. “You can’t punish us.”

The headmaster’s eyes blazed with fury. “You disobeyed the instructions of your headmaster. For that you deserve a caning.”

The three boys shuffled their feet nervously. This was not going as planned.

“Yesterday, I caned thirteen of your colleagues. They attended at my study as instructed. They took their punishment like men.” Dr Fortescue’s face coloured. “You three boys did not. And for that you will receive an exemplary beating.”

“B..” Tony Brown started to protest but the steely glare of Dr Fortescue silenced him immediately.

“I shall cane each of you severely. As both a punishment for your wrongdoing and also to serve as a warning to others. I will not tolerate such behaviour.”

Green blushed deeply. There were tears welling behind his eyes.

The headmaster waved his hand. “You will lower your trousers and underpants and bend over that chair.”




All three prefects voiced their protest. The cane. On the bare.

“Silence!” Fortescue thundered. “I will brook no defiance.”

“Bbbbb…” the mumbling of dissent continued.

“You will obey my instruction. Or you will leave the school this minute.” He glared at each boy in turn, daring them to defy him.

“Then we’ll see what happens to do. Expelled pupils do not easily secure places at university.”

Dr Fortescue turned his back on the miserable prefects and strode the length of his study until he reached a tall thin cabinet in one corner. It was not locked. He pulled at the door and stood to one side, ensuring the three rebellious prefects had a perfect view of its contents.

Brown glanced at Lender and Green in horror. Green could only stare down at his feet. It was an awesome array of punishment canes. Some were thick and others thin. At least three were with curved handles and one had duct tape wrapped around one end to form a grip.

The good doctor delved inside the cabinet. He felt hot stares burn into the back of his neck. The headmaster always enjoyed the drama of such occasions. The canes rattled in the confined space of the cupboard.

He chose one. It was more than three feet in length, straight and as thick as his little finger. He showed it to the three boys he was about to thrash and flexed it between his hands. Despite its thickness, it made a perfect bow. He was delighted to watch Green’s face drain of all colour.

Seemingly believing that the cane would not deliver the appropriate severity of punishment, Dr Fortescue replaced it and after much rustling, he selected another.

This one was dark yellow in colour and was slightly longer than its discarded companion. It had the “traditional” crooked handle of the school cane. Dr Fortescue swished it through the air, testing its suppleness. The prefects could be under no illusion: it was a mightily whippy rod. It would deliver a very painful caning across trousers and underpants. On the naked buttocks it would be excruciating.

Satisfied with the ability of his choice to perform its task, Dr Fortescue closed the cabinet door and turned his full attention to the three prefects standing abjectly before him.

He was ready. There was no more to be said.

“You boys,” he barked at Brown and Green, “Face the bookcase.”

They did so in an instant

“You,” he roared at Lender. The wretched boy jumped. The headmaster wobbled the cane in front of Lender’s face. “You first. Trousers, pants down. Over the chair.”

Bob Lender stood his ground. Rooted like a tree. This could not possibly be happening. Not to him. A sixth-former. A prefect. He was eighteen years old. An adult.

Swish! The cane flew through empty air, creating an almighty swooshing sound as it went. “Please, don’t make me ask you twice,” Dr Fortescue growled menacingly.

Reluctantly, Lender shuffled a few paces forward toward the armchair. Dolefully, he turned to the headmaster, his eyes pleading. Dr Fortescue had a heart of stone. Nothing would deter him from his mission.

“Quickly boy. I haven’t got all day.”

Bob Lender tried to exchange glances with his two companions. Perhaps if they acted in unison they could do something. Could they overpower the tyrant of a headmaster? Neither boy could bear to look at him. In this moment he was on his own.

Bob stared into the middle distance. There was a photograph of the school rugby XV on the wall. He studied the faces of the boys in the front row as with fumbling fingers, he released his belt and unzipped his trousers. They fell to his knees.

Once again he stood rooted. One of the boys in the photograph had his eyes tightly closed. Another flashed an inane grin, from ear-to-ear.

“Underpants down, boy,” the headmaster’s command seemed faint. As if it had drifted in on the wind from hundreds of yards away.

As if on autopilot, Bob hitched his thumbs into the waistband of the pants and pushed them down; slowly. First over his hips, then down his buttocks. At last they slipped of their own accord down his thighs.

Once again, he could not move. The dreamlike quality of the moment troubled him. Was this really he, Bob Lender, standing in the middle of the headmaster’s study with his naked bum and his private parts on display?

Thwack! Dr Fortescue brought the cane crashing down across the back of the armchair. “Stop this nonsense. Bend over. Now,” Fortescue’s fury was not faked. “Or you will get extra strokes.”

Bob Lender took an almighty swallow of air, fell forward and clutched the seat cushion for all he was worth.

“Legs further apart. Bottom higher.”

Bob wriggled his hips.

Fortescue gripped the tail of the boy’s shirt and folded it up his back.

He stood back, cane in hand. He tapped it across the centre of Bob Lender’s naked buttocks.

Dr Fortescue had caned many backsides. Sixth-form buttocks were a speciality with him. As eighteen-year-old bums went, Bob’s was typical. He was no athlete; he never played games. He didn’t run or swim. His buttocks were not made firm and muscular from exercise. Nor were they yet much affected by a diet of beer and pub pies. That would happen sooner rather than later.

Bob’s buttocks tightened somewhat when he was in a bending position. Dr Fortescue pressed his cane into the flesh testing its “give” and noted carefully how far it sank. Then, without warning, he raised the stick to about shoulder height and whacked it at speed into the boy’s bare bum.

Bob’s eyes popped and his mouth gaped open and quickly closed. The pain sank into his haunches, but he made no sound.

Thwip! Number two followed, twenty seconds later. The teenager closed his eyes tightly and shook his head. His face was scarlet. His bum was turning a deep shade of pink.

Number three fell lower. Bob bunched his fingers into fists and punched them into the hard seat cushion. “Sssssss!” air escaped through his lips. The pain was increasing. It started on the crown of his bum and travelled up and down his legs. It hurt like crazy, but so far he made no sound.

His resolve not to let the foul Fortescue know he had been hurt was broken by the fifth cut. The headmaster made no concession to the lack of clothing on the boy’s behind. Each stroke had been a swipe. It was as if the headmaster was beating a carpet.

Bob Lender let out a yelp, so shrill that his two companions swivelled on their heels to see what had happened.

Green’s jaw gaped open. He had a perfect view of his friend’s scarred backside. The once creamy-white cheeks had been slashed by five cuts of the cane. Distinct marks ran in almost perfect parallel from left to right. Two cuts looked particularly deep. Blood was starting to weep.

Bob Lender stamped his feet up and down and wriggled his hips. It made no difference. The agony was overwhelming. He was spent. He couldn’t take any more of this bare-bottomed thrashing.

Keith Green watched in awe as the headmaster changed his stance slightly. The headmaster’s stare troubled Keith. He couldn’t quite make it out. It wasn’t blank and distant. It might have been the look of anger, but the boy was certain the headmaster was beyond that. This whipping was cold and calculated. It wasn’t in the heat of rage.

Then he got it. The look in Dr Fortescue’s eyes. He was enjoying himself.

The headmaster tapped the cane diagonally across Bob Lender’s cheeks and brought it down with considerable force across the five welts already embedded in the boy’s rear.

Lender shrieked as each of the previous cuts was brought back to life. Tears flowed down his cheeks. The tempo of the military marching doubled. Keith banged his head up and down against the seat cushion, but nothing, nothing at all, could ease the agony.

Fortescue took a pace or two back and from that distance he admired his handiwork. Before him he saw a pair of lacerated buttocks. The cuts would be painful for some time to come. The sixth-former would find it unpleasant to sit on a hard surface for the rest of the day. The bleeding would stop within minutes, but the welts and bruises would be with him for many days.

Bob’s sobbing had eased, but tears still drenched his face.

It was, Fortescue concluded silently, a job well done.

“Stand up.”

Bob didn’t need telling twice. He shot to his feet and within seconds he was once again dressed.

Solemnly, Dr Fortescue swished the cane.

“You,” he pointed at Keith Green. “Take his place.”

Right or wrong, the headmaster of the school had to be obeyed. But there was rebellion in Green’s dogged look. But he realised the futility of such a contest, Dr Fortescue would always win.

Slowly, Keith Green released his trousers, slipped down his pants and bent over the chair.

Swish, swish, swish! Fortescue laid it on. He put plenty of beef into those swishes. They rang around the study. Keith had to clench his teeth hard back a yell. Unlike his pal Bob, he had greater success. Swish, swish, swish!

It was a tremendous “six” and every one of them a swipe.

Keith’s face was as scarlet as his buttocks when Fortescue had finished.

Then it was Brown’s turn to show humility. With a dismal face he bared his backside and offered it up to the headmaster.

The cane rose and fell in a succession of cuts that sounded like pistol-shots. It was as thorough a licking as Fortescue had administered to Brown’s companions. And such a licking as Brown had never experienced before.

He yelled and he howled and he squirmed and he roared, and still the cane swiped and swiped.

Dr Fortescue laid down the cane at last. He was quite tired with his exertions.

With the prefects dismissed, the new headmaster settled down in the armchair that had just held their prostrate bodies. What a start it had been to his new school career. Every prefect had felt the sting of his cane. They knew he meant business.

Next, he would make a start on the rest of the sixth-form. But that could wait until tomorrow.

On his way back to the hotel he stopped off to buy a half-bottle of “Teachers” whisky. The name on the label always made him smile ruefully. Back in his lonely room, its contents induced a fitful and fretful sleep.

The Tyrant Headmaster, episode 4 Smoking on Saturday is here

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Charles Hamilton the Second

The Tyrant Headmaster 2. A new beginning

cane (39)

Dr Fortescue is the new headmaster at St Septimus Independent Grammar School. It is his first day, but the previous night he had been confronted by a sixth-former in his school uniform drinking in a hotel bar. Now read on.

Episode 1 is here

Peter Rodriquez was bemused. A junior boy had delivered the message: he was to report to the headmaster’s study immediately after the end of last class. Then, the young whipper-snapper grinning from ear to ear proceeded to slash his arm through the air in parody of a cane swishing down upon a boy’s bottom.

The boy might be on to something, Peter thought. Why else was a chap summoned to the head’s study except for a bowing? But, Peter had not done anything wrong, and beside this was the head’s first day at the school; why would the Beak want to see him?

It had taken Dr Fortescue no time at all to identify the boy in the bar. The school records included photographs of every boy. It was a very nice picture; Peter Rodriquez had a very warm smile. But it would be a different part of the boy’s body that would be warm by the time the headmaster had finished with him.

St Septimus Independent Grammar School dated from sometime in the seventeen-hundreds. It was a traditional school: traditional teaching methods, traditional sports, traditional school uniform and traditional discipline. It was a boys-only independent fee-paying grammar school with delusions that it was an elite public school.

Dr Fortescue was very pleased with his new study; it afforded him the status that he felt he deserved. It was set in the clock tower with narrow stone steps leading to it. He especially loved his huge desk, topped with green leather. Behind it was a window that overlooked the school grounds with its ivy-covered walls and mullioned windows.

The walls of the study were panelled in oak. A large open, as yet unlit, fire dominated one wall and two others had shelves and cabinets, including a tall thin cupboard with a smoked-glass front. A Chesterfield couch and two padded armchairs made up most of the furniture, but there were also two straight-backed chairs leaning against one wall.

As he sat at his magnificent desk, he pondered the past. Which of the many choices of furniture had been his predecessor’s favourite? Did he prefer to have a boy over the desk; or the armchair, or the vast Chesterfield? It would, of course, depend somewhat on the size of the boy.

Rodriquez was a tallish boy, Dr Fortescue recalled, he could easily drape himself over any piece of furniture in the room.

The tall thin cabinet contained an array of punishment instruments. The good doctor only used the cane himself; it was the only instrument that a headmaster should use. A thrashing by the Beak had to be awesome, something to be feared by the boys. That was why he would not be using the leather taws or white rubber-soled gym shoe that he had discovered in the cabinet.

The array of canes was impressive, but not complete. There were seven assorted rods, some with the traditional crook-handle; most were made of rattan and two were dragon canes. The dragons would be ideal for beating older boys; but there was something special missing. Dr Fortescue had intended thrashing Rodriquez with a Malacca cane. The Malacca was no bigger or thicker than any of the other canes in the cabinet; but it was denser. Typically, a Malacca would have notches every three inches or so along its lengths. These notches would cut into the flesh and leave severe bruises and welts; even when applied to a boy’s bottom covered with trousers and underpants. When applied “trousers down,” even on the underpants, it would rip at the meat of the buttocks. A boy would carry the marks of such a thrashing for at least a couple of weeks and sitting down would be a painful business for many days following the beating.

Dr Fortescue was disappointed that no Malacca was available, but he was not despondent. He had several such canes and soon they would arrive with his personal belongings at the headmaster’s house he had inherited with his new position.

The school day over, Rodriquez slowly made the trip to the headmaster’s study. He still had no idea why he had been summoned. He knocked gently on the heavy oak door of the study and waited for the call to enter.

Rodriquez looked as resplendent this afternoon as he had in the bar. In addition to his blue-and-white blazer and clinging grey trousers, he wore on his head the official school cap, which emphasised the boy’s dark brown eyes and olive skin.

Unbidden, he shuffled into a positon in front of the headmaster’s desk, clasped his hands behind his back and stared down at the slightly worn rug beneath his feet. He noticed, for the first time, that his shoes were scuffed and needed polishing.

The boy stood in silence. Dr Fortescue looked at him stone-faced; his white moustache bristled and his knitted white brows frowned. “Do you not remember me?”

Rodriquez raised his eyes from the floor to look at the headmaster. What he saw was an elderly man dressed in a rather old-fashioned academic gown, seated behind his huge desk. Even sat down he seemed a commanding figure. When the headmaster later stood from his chair Rodriquez would see a tall, grim man. And, he was strong as an ox, as could be testified every time he swiped down a cane across a boy’s backside.

Mr Fortescue realised for the first time that the wretched teenager before him genuinely did not recognise him.

“Let me jog your memory. The bar of the George Hotel, last evening.” The boy’s shocked reaction delighted the headmaster. Now, he would make him suffer.

Dr Fortescue recapped their previous encounter: the smoking, the drinking and the rudeness.

“So, Rodriquez what do you have to say for yourself?” the headmaster inquired smugly. He had the boy just where he wanted him. He would dismiss all pleas for clemency. The boy would receive an exemplary thrashing.

“All the boys do it, Sir,” Rodriquez spoke confidently, “Well a lot of them that is. We are eighteen, one or two of the chaps are nineteen.”

This is not what Dr Fortescue wanted to hear.

“You tell me Rodriquez that many of the sixth-form boys hang around bars drinking and smoking. And they do this while wearing the uniform of St Septimus?” the shriek in his voice betrayed his incredulity. He could not believe that guttersnipes from the town’s secondary modern school would behave this way. It was behaviour totally unacceptable for grammar school boys.

“Well, yes, Sir,” until this moment it had not occurred to the boy that his behaviour was abnormal. Sixth-formers had been visiting pubs for years. And as for smoking; there was a special area close to the maintenance huts where senior boys went. He assumed all the masters knew this and they simply ignored it.

Rodriquez did not say this to the headmaster; he was not the brightest boy at the school, but he could see that things were going to change with the new Beak.

Dr Fortescue summed up the situation swiftly. He had thought that Rodriquez’s smoking and drinking had been the isolated behaviour of one boy. Now, he realised there was an epidemic; boys all over town were besmirching the good name of St Septimus. He had to put a stop to it and swiftly.

He had intended thrashing Rodriquez that afternoon in the privacy of the headmaster’s study, but now his plan must change. The boy must be made an example of. His fellow drinkers and smokers must learn the consequences of their own behaviour.

That was why the following lunchtime the entire sixth-form was called to the prefect’s room.

The doctor, like so many schoolmasters, was a bit of a ham actor and he laid into the boys. “Such behaviour is despicable. It is intolerable,” he stretched out each syllable for what he imagined was dramatic effect. In fact, the boys thought he sounded absurd, but they dared not snigger. Dr Fortescue had complete control over them and they knew the lunchtime would not end happily.

“Smoking is banned. Pubs are out of bounds. At all times. Whether you are in school uniform or not.”

An audible sigh came from the back of the room.

“Who did that? Who was it!” the headmaster barked. Toby Justice, a frequent smoker and drinker, ducked his head low, hoping that the good doctor had not spotted the culprit.

“Pah!” Dr Fortescue was in no mood for dissent. “That is my final word on the matter. No smoking and no drinking. If any boy is caught in these activities I shall consider it to be a breach of the headmaster’s direct instruction, and I shall not hesitate in thrashing that boy with the utmost severity!”

“But, Sir, Dr Fortescue, Sir,” a tall fair haired boy rose to his feet. “You can’t do that. Sixth-formers can’t be caned.”

The headmaster’s jaw dropped. “What did you say? Who are you boy!” he roared.

The fair-haired boy blushed scarlet. He hadn’t expected this.

“Please Sir,” he whimpered, his confidence evaporated. “I’m Turner, the School Captain.”

Dr Fortescue took a deep breath and let rip. “The School Captain,” he bellowed. “Not any more. How dare you contradict your headmaster!”

“But, Sir.”

“Silence. Do you want to join Rodriquez? You are stripped of your privileges. I shall choose a new School Captain. Someone more suited to the position.”

Slowly, deeply humiliated, Turner returned to his seat.

One or two sixth-formers visibly blanched. Who was this man? Could he do such a thing? But, they already knew the answer. St Septimus was an “independent” school and the headmaster had the authority, invested in him by the governors, to do just that. And more.

Then, he turned his attention to Rodriquez. All the assembled boys knew he had been caught red-handed by the headmaster. It was not fair, they all thought it, Rodriquez had not been warned of the new rules. Why should he be beaten?

They all thought it, but not one boy dared voice a protest. Instinctively they knew Dr Fortescue was quite capable of flogging each and every one of them; and assuredly he would do that if just one of them squeaked up.

Dr Fortescue picked up a dragon cane he had placed strategically on a long wooden table. It was the most awesome of the collection he had inherited. He was disappointed that one of his prized Malacca canes was not in his hand, but he would deliver a sound thrashing nonetheless.

He swished the cane in Rodriquez’s direction. “Rodriquez; lower your trousers and bend over the table.”

There was an audible gasp. Nobody had expected this. Blood drained from Rodriquez’s olive-coloured face and his beautiful dark brown eyes began to water. He had expected a caning, and a severe one at that, but he had been caned before; he knew it would hurt like buggery, but it would not kill him. He did not mind too much being beaten in front of his sixth-form pals. They all agreed he did not deserve his thrashing; they were on his side. He would be a hero at the end of it all, and the good doctor would be universally despised.

But, trousers down. Rodriquez hated being seen naked. Changing for the gym classes that were compulsory at the school, even for sixth-formers, was for him a terrible ordeal. He feared the fellows would think his prick was tiny.

“Come on Rodriquez, we haven’t got all day. Afternoon school will start soon,” Dr Fortescue’s words dripped with sarcasm.

Every pair of eyes in the room stared intently as the eighteen-year-old schoolboy fumbled with the belt of his trousers. They fitted Rodriquez perfectly and he did not really need a belt. Soon it was loosened and with trembling hands the boy started on the buttons on his fly. One, two, three, four, slowly each button was unfastened. Then with the weight of the wide leather belt and the force of gravity the mid-grey trousers slipped down the boy’s thighs, past his knees and came to rest at his shins.

“Stand the other side of the table and bend forward.” Dr Fortescue had two choices; he could force Rodriquez to go across the table so that his audience would see the boy’s face and witness every grimace, yelp and moan the poor boy made. Or, he could have Rodriquez face the opposite direction with his bottom pointed at his fellow sixth-formers so that they might get a full view of the whippy cane crashing into the boy’s stretched cotton underpants. They would also see Rodriquez’s feet stomping up and down and his body writhing in agony as slash after slash bit deep into his pert bottom.

So, with his bum on full view, Rodriquez lowered himself over the table.

“Lie flat on the table, keep your feet apart.”

Rodriquez did as instructed, thankful that he was not positioned to see his audience. He could now close his eyes, grit his teeth and pretend that he and the headmaster were alone in the Beak’s study.

Dr Fortescue took hold of Rodriquez’s crisp white shirt and pushed it up the boy’s back. Then, he tugged at the waistband of the already tight white cotton Y-front underpants until all wrinkles were removed from the cloth. He hesitated a moment to admire the contrast of Rodriquez’s smooth olive skin against the gleaming white of his clothes.

Rodriquez felt the tap, tap, taping of the cane against his stretched bottom. The headmaster was taking his aim. The miserable boy screwed his eyes tight and with his arms outstretched ahead of him he gripped the far edge of the table.

He heard the swoosh and the crack of the cane a second to two before he felt the searing pain. The headmaster had laid a stroke with the utmost force right across the centre of both cheeks. At first the boy felt nothing, but then it was as if the man had pressed a white hot wire into his flesh.

All the wind was pushed out of Rodriquez’s body. He wanted to yell and scream but all he would do was wheeze. Tears already rushed from his beautiful dark brown eyes. His feet marched up and down on the spot like some demented soldier on sentry duty,

A pause. It seemed like an eternity to Rodriquez, but it was only twenty seconds. Dr Fortescue knew this because he was counting the time in his head. Then swipe! crash! The headmaster put all his beef into stroke number two. It landed about a quarter of an inch below the first. None of his audience was awarding marks, but later they would all agree that the good doctor was an expert with the cane. None of them would want to be on the receiving end of a Fortescue flogging.

Rodriquez’s body jerked and he lifted himself off the table top; his hands sprung to his backside and he bent over double, as simultaneously he wailed and rubbed away at his scorched flesh.

“Get back down Rodriquez. Now!”

The miserable boy might not have heard the command, so great was his agony and his desire to try to rub it from his buttocks. In any case, he did not obey the good doctor’s command.

“You boy. And you!” Dr Fortescue pointed at random to two sixth-formers close by. “Each of you take one of his arms and hold him down across the table.”

Rodriquez put up no resistance and in seconds he was restrained across the table. The headmaster was pleased that his command had been obeyed. He was no fool; he knew he was vastly outnumbered by the boys in the room; if they chose to they could have prevented this spectacle from taking place.

Dr Fortescue was delighted that he had them under his total control.

“Now, Rodriquez,” he gripped the top of the boy’s underpants, “As an extra punishment for standing up, let us remove these.” So saying, he pulled the crisp white pants down so they lay bunched just below the crease where the cheeks meet the thighs.

Two dark red cuts were clearly visible, even to the boys at the back of the room. The whipping had been vicious. Poor Rodriquez was already cut to shreds and he was only two strokes into the punishment. And, the next four would be delivered across the unprotected naked buttocks.

With Rodriquez’s buttocks now bared, Dr Fortescue was able to pick his next spot with accuracy. He whipped in the dragon cane just below cut number two. Rodriquez had tremendous strength and it took the combined weight of both boys to restrain his movements. An ugly thick weal immediately appeared on the once olive-smooth cheek. Rodriquez screamed with the agony and saliva poured from his throat to join the tears and the snot had was already being evacuated from his body.

Swipe! Number four was high, right at the top of the globes, which until now had been untouched by the fierce rod. Rodriquez’s body jerked and then went still. In alarm, one of the boys let go of his hold.

“Take hold. He is all right,” Dr Fortescue barked.

Terrified, the boy resumed his grip and the headmaster brought down cut number five. It sliced across the crease of the boy’s bottom and he let out an almighty moan and kicked his legs. His breathing was shallow, but he was conscious.

Number six. Dr Fortescue believed a headmaster’s caning must be awesome. He had his own method to ensure this was so. He moved his position slightly and tapped the cane across the buttocks. Just these small movements sent shock waves through Rodriquez’s body. But that was as nothing to what came next.

The headmaster raised the cane to above shoulder height and with all the force he could muster (which was considerable) he brought the rod flogging down at a diagonal, so that the lash crossed over the five deep throbbing cuts that already decorated Rodriquez’s bottom.

The agony was intense. Despite his weakened state, the sixth-former let out the most blood-curdling yell. It could be heard throughout the building and into the quadrangle below. Then Rodriquez lay, still held securely, face-down across the table and sobbed and sobbed his guts up. Vomit rose from the pit of his stomach and he just managed to gulp it back to stop it flooding from his throat.

The room was silent. Only the pitiful sobs of Rodriquez broke it. Not one boy in the room knew what to say. Their new headmaster had demonstrated his total control over them.

In time, Dr Fortescue nodded to the two sixth-formers on security guard. It was their cue to release the wretched Rodriquez. Slowly, he raised himself from the table to a standing position. His legs were weak and he stumbled, but grasped the table’s edge to stop his fall. His was regaining some of his breath, but had to stand, hands on knees, while his body started the long process of recovery.

This bending position allowed each boy in the room a perfect view of the ripped buttocks. There were six thick red cuts and blood was beginning to seep from wounds created where the diagonal lash intersected with the others. No one in that room could be in any doubt; the same punishment would be meted out to any boy who dared to disobey the new headmaster.

One boy had taken it upon himself to help Rodriquez to dress. Dr Fortescue had a sneaking suspicion that this was the boy who had joined Rodriquez at the bar last evening. He could not be certain, but he would investigate later.

Tenderly, the boy pulled up his friend’s underpants and trousers. It was obvious that the touch of the cloth against the wounds caused Rodriquez some distress. But that could not be avoided; the alternative was for the miserable boy to leave the room naked from the waist down.

Dr Fortescue himself took deep breaths. The effort of the severe bare-bottomed caning had taken its toll on him a little. He would need to retire to his study for a reviving gin and tonic.

Peter Rodriquez, his arm around the shoulder of his friend, was escorted, limping from the room.

The headmaster waited another twenty seconds before declaring, “That is over. Please vacate the room immediately.”

And, in total silence, the sixth-form boys did just that.

Episode three of The Tyrant Headmaster is here

Other stories you might like

The Gaffer of the Academy: 1. Beginnings

The run

Pyjama bottoms down. Bend over

A punch in the face


More stories from Charles Hamilton II are on the MMSA website

Charles Hamilton the Second

The Tyrant Headmaster 1. The boy at the bar

The man sat hiding behind his newspaper. His second large gin and tonic was nearly drained. Sitting at the bar, his back to the man, was the mysterious boy.

He wore a distinctive blue-and-white blazer. He was obviously a schoolboy; almost certainly a sixth-former. The man could just make out the outline of the boy’s school cap in his blazer pocket. In his hand the boy held a beer.

They were the only customers at the George. The boy was in energetic conversation with the barman, a youth probably no older than himself.

Who was this boy? The lighting in the bar was not good. From where he sat the man thought the boy might be a little Indian. Or did he have some Spanish in him? Italian perhaps? The boy’s jet black, almost blue, wavy hair was cut short exposing a longish slim neck. Was he an athlete? He seemed to have quite a muscular back.

Suddenly the boy stood up from his stool and leaned across the bar. What a terrific sight. His mid-grey school trousers clung to the outline of his legs which went all the way up to tight muscular buttocks. Oh yes, the man thought, very spankable.

The boy found the book of matches he was searching for and he reached into the inside pocket of his blazer and extracted a cigarette, put it between his lips and confidently lit it.

Dear God, the man thought, a child drinking and smoking, in broad daylight and in his school uniform. That was the problem with schoolchildren these days, he thought, they think they are grown up. They are not: they are children and they should be treated like such. If he had his way boys would wear short trousers until the day they left school, even if that was at eighteen. Short trousers reminded a boy he was exactly that: a child, not grown up. He should behave like a child; he should respect his elders and betters and submit at all times to authority.

The boy would look great in short trousers and knee socks. They would show off his legs and bottom to perfection.

The man’s thoughts were interrupted by the sound of giggling. The boy and the barman were sharing a joke. Were they talking about him? Had they spotted him ogling the boy’s bum?

He dived behind his newspaper and pretended to read, but he could not ignore what he had seen; this gorgeous sixth-form schoolboy in full school uniform drinking and smoking before his very eyes. And, the teenager was not even trying to hide. The man thought he would at least have taken his distinctive blazer off and put it in a bag.

He remembered a story he had seen in a newspaper the other month. One of the Sunday scandal sheets reported that a group of boys from a public school (that is an elite private boarding school) had sneaked off one evening and gone to a pub. They were spotted and reported to the headmaster, who proceeded to award the boys six-of-the -best with his whippy rattan cane. Most of the boys were eighteen years old, and one was nineteen, but that did not deter the headmaster from his duty.

The newspaper did not report whether the thrashing was given “trousers up” or “trousers down,” but the man expected that white cotton underpants, or even bare flesh, had been on show in the study that day.

The man hated staying in hotels on his own; it was boring and there was nothing to do except drink. He picked up his empty glass and took it to the bar.

“Same again, Sir?” The barman was rather delicious too. He wore black trousers with a high waistband and a sparkling red waistcoat; a combination that showed off his flat, firm buttocks.

The man had just completed a long tiresome railway journey and he had not eaten for several hours. The gin was beginning to go to his head.

He stood and waited for the barman to perform his drink mixing duties and tried not to eye-up the boy sitting beside him; but failed.

“Good afternoon, Sir,” the boy in the blue blazer was embarrassed by the attention he was getting and flushed a little.

The accent was pure “English received.” He sounded like a minor member of the British Royal Family.

The man stumbled on his reply. Close up he could see the boy’s sparkling dark brown eyes and his very-kissable full lips. His skin was a little olive in colour. Perhaps he was English, but from somewhere he had a little Mediterranean blood.

“Sir,” he called me “Sir,” the man thought. At least he was not some guttersnipe lout.

“Good afternoon,” he replied. The following silence was intense. Neither man nor boy knew what to do next.

The man filled in the silence. “That’s a very distinctive blazer you are wearing. Is it some kind of sporting club?”

The boy smiled. His olive face and dark brown eyes shone. His lips parted into a wide smile. “Oh, no. It’s St Septimus Independent Grammar School,” he said with great emphasis on the word “Independent.”

Ye Gods! The man thought. He is not even trying to hide where he is from.

The boy was very proud of his school. “It is the most prestigious school in the whole county,” he beamed.

The man’s jaw quite literally dropped. St Septimus Independent Grammar School. The most prestigious in the county.

“Well,” he retorted tartly, “If it is the most prestigious school, why are you besmirching its name by drinking and smoking in public while wearing its uniform.”

The boy bristled. He did not expect to be spoken to like this by a drunken old man.

“What are you doing here? Are you even old enough to drink alcohol?”

The boy and barman exchanged glances. The barman’s look said, “Leave it alone,” but the boy could not.

“Frankly, Sir,” he said with mock politeness. “I don’t think that has anything whatsoever to do with you. Now, why don’t you take your drink and return to your newspaper.”

“Nothing to do with me. Nothing to do with me,” the man thought it twice for emphasis. “We shall see about that young man.”

He picked up his gin and tonic and returned to his table. At that moment another young man, about the boy’s age, but not dressed in school uniform, arrived and the two of them fell into relaxed conversation.

Fuming, the man gulped on his drink and unsteadily returned to his newspaper. He spent the next few moments imagining the boy in his blue-and-white blazer and clinging trousers bent across any one of the many large padded leather armchairs in the bar. Once he had the boy over the high bar stool and then again he was bent across the bar itself. Finally, in his imagination, the boy was bent touching toes in the middle of the bar. In all his imaginations and whatever position the boy was in, there was always the man himself swishing a stout cane before flogging it into the boy’s stretched buttocks.

Two hours later the man sat on the edge of his bed. The hotel room was spinning a little. He had taken wine with his meal and now he told himself he should collapse into bed. He could not get that boy out of his head. Even now, he imagined the boy draped across the armchair in his room; only this time the boy’s trousers and underpants were at his ankles and the man was lashing the cane with such force that blood was seeping from the resulting wounds.

The man’s penis stiffened. He was not proud of this. When this happened in the past, he found a facecloth dampened with cold water placed in the strategic spot usually dealt with the swelling. This night, however, he would use hand relief.

Eventually, he rolled into bed. He needed a good night’s sleep. He needed to be fresh in the morning. Tomorrow was his first day as the new headmaster at St Septimus Independent Grammar School.

Episode two of The Tyrant Headmaster s here

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Six of the best caning stories 6. Unfinished business

High school reunion

The cartoonist’s painful memory


More stories from Charles Hamilton II are on the MMSA website


Charles Hamilton the Second