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.


Other school stories you might like


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

Murph in the headmaster’s study

New boy at school




More stories from Charles Hamilton II are on the MMSA website


Charles Hamilton the Second

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