Housemaster’s Double Caning

z used drawing cane master (3)

A St Francis Independent Grammar School story. Click here for the full series.


“Da Silva in here now,” I heard the order barked out knowing my time had come, so I opened the door and entered the lion’s den.

I had been summoned to this room many times before. Nothing had changed since my last visit: a large bookcase stretched across the wall in front of me. To my left was a small couch where guests would sit, large stuffed chairs on either side. To my right was the housemaster’s huge mahogany desk, clean and tidy, and polished to perfection.

But, despite the abundance of furniture, all I could focus on was the prominent display behind the desk. Attached to the wall was a large wooden cabinet with a glass door. Through the glass I could see three crook-handled canes. They were light brown, slender, and slightly warped from years of use.

Mr Hill, my housemaster, was seated at his desk, dressed in his formal gown, with a dark suit under it.

“Stand there,” he pointed to a spot on the worn rug directly in front of his desk. I cannot ever remember in my seven years at the school having seen Mr Hill smile. This day was to be no exception. His steely grey-blue eyes glinted and he had a face like thunder. He was a man of few words. I was not entirely sure why I had been called to the study (I had broken a number of the school’s petty rules in recent weeks and any one of them might have resulted in a thrashing) but in no time my housemaster enlightened me.

“Well I know, even if you do not, boy. I know that you have not been concentrating on your work as an A-level student should. I know that you have been larking about with your pal Roehampton, whose work is almost as inadequate and unacceptable as yours.

“So I am going to make an example of you and give you a wake-up call. I am going to give you six of the very best – possibly the best you have ever had! Take off your blazer and hang it up over there.”

The housemaster had a reputation as a very fair but firm man and I knew better than to argue a point and anyway there was something about Mr Hill when he used that tone of voice that meant you gave him total obedience.

“Oh God! Another caning.” The thought raced through my mind as with my heart pounding in anticipation of the ordeal to come I slipped the blazer off my back and hanged it as instructed on a hook on the study door. The task completed I turned to once again face my punisher.

He had left his desk and placed the caning chair in the middle of the room. No one ever sat on this chair and there was no wear on the seat. However the varnish on the back, and on top of the front legs, was worn away by generations of boys bending over and holding on to the chair while they were caned.

“You know what to do,” he said. Yes, I remembered the procedure, even as I tried to forget what would come next. I had been in a similar position many times before. Without fuss I bent my athletic body prostrate across the chair presenting my eighteen-year-old buttocks tightly stretched inside snug fitting trousers to the housemaster.

Mr Hill rolled his sleeve up and took a springy cane from the selection in the glass-fronted cabinet. I could see him rubbing a piece of chalk up and down his cane as I waited for the first slash to cut into the taut grey trousers that were now spread over my small squatting bum.

Mr Hill flexed the cane a little and scythed it through the air. It made a fearsome noise. It reminded me of the many unhappy times I had spent in this study over the years.

I flinched as I felt him pull the end of my shirt out from under the waist-band of my trousers and all too soon the cane was tapping the middle of my buttocks. I kept telling myself that it was not going to be too bad, right up until I heard the crack then felt the fire sweep across my bum, Jesus he was going to rip my backside open.

He measured the rod out again, lower, pressing into the tight material of my trousers, before flogging it against me just as hard as the first, the retort of wood against cotton filling the air.

Even with all my experience, I could not have anticipated the pain, it was a hundred times worse than anything I had felt before. My eyes filled with tears, but I tried to remain calm, forcing myself to breathe while gripping tightly to the chair.

Then the third stroke thrashed hard into my poor bottom, I actually screamed and my body began to vibrate. The pain was intense, burning: unendurable.

“Control yourself boy. You have only had three strokes. I do not expect that racket,” Mr Hill admonished me as he raised the cane high into the air again and delivered Crack! the fourth cut. I screamed but held on as the agony built up. Then further pain as another crack announced the arrival of the fifth stroke. I was blubbering, pleading and screaming.

Despite my tormented state I could still feel the pressure of the cane pushing into the bottom of my buttocks as he lined up the sixth and last stroke. I know I was crying “No, please. No.” as the cane whistled into the allotted landing site with all the force that Mr Hill could put into it. As soon as it was done I stood up and my hands went to my bottom. I was in utter agony, tears were running everywhere, mainly due to the pain, but also as I was so ashamed that I could not have controlled myself better.

Mr Hill placed the cane back in the cabinet while I tried to check myself from giving my arse a rub, but my rear was burning and although I didn’t want to show it had hurt I knew I had failed miserably.

The housemaster was now sat at the desk filling in the punishment book, through my tears he passed the book and told me to initial it.

With no further ado he dismissed me from the study. Miserably, I hobbled towards the door, unhooked my blazer, and without waiting to get dressed properly, I left.

Mr Hill was so clinical in the way he had delivered the punishment I felt he had no heart, my backside was blazing and I could feel the welts raising on my skin but he was dismissing me as though he had just given me nothing more than directions to the railway station.

Once outside I clamped my hands onto my burning bottom and began to massage the sting. Never again I thought to myself as I headed off to my classroom. Never again; after nearly seven years at this school and countless canings I vowed it would be the last time.

I watched, as Da Silva, in obvious agony but determined not to show it, hobbled from my study. This boy was a problem. I fervently believe in corporal punishment. Beat a boy hard enough on his backside when he steps out of line and he won’t come back for more. The cane works, I know it. But, I suppose Da Silva is the exception that proves the rule: he is a recidivist, a repeat offender, and it is difficult to deal with a boy like that. The only option you have is to thrash him a little bit harder each time he bends over in front of you.

Or of course, repeat offenders can be ordered to take down their trousers to receive six across the underpants: or sometimes even across the bared buttocks. Here at St Francis Independent Grammar School, the governors only allow the headmaster to thrash a boy in such a manner, more’s the pity.

Some people say it was wrong to beat teenaged boys on their bared buttocks; some even suggest schoolmasters are “pederasts.”  Today there are “Progressives” who say we should abolish corporal punishment altogether.  What tommyrot: asking a schoolmaster to give up his cane! Where should we be then? If the cane were abolished the country should be in a state of anarchy within five years.

I was beaten on the bare myself at school. Yes, I admit it, I was a repeat offender. It did me no harm: it made me the man I am today. I was a smoker and had been given the standard Six on the trousers by my housemaster. It taught me a lesson, I can tell you, but a few weeks later I was caught puffing on a Woodbine behind the gymnasium and this time I was up in front of the Beak (as we called the headmaster, affectionately I’m sure, at my school).

I can remember it as if it had happened only this morning. It did not matter that I was a senior boy and at eighteen was due to leave the school in a matter of weeks. There was no big sermon; he and I both knew why I had been summoned to his study. It was confirmed that I had been beaten for a similar offence only weeks previously. In no time I was bent over a wing-backed armchair, my trousers and white cotton underpants at my thighs. The Beak folded back my shirt and grey short-sleeved pullover away from my buttocks until they rested on my shoulders. Then without further fuss he laid six stingers across the centre of my bare cheeks.

It hurt like hell, but schoolboys have a code of conduct and we resolved never to show our punisher that we were in pain. I tried my best, my level best, to be stoical, but after slash number two ripped my bum to shreds I was pounding my fists against the back of the armchair in agony. The heartless headmaster was not deterred and whipped the rattan cane down with great severity into my now bleeding rump.

I lost control and tears washed down my cheeks. My bum felt like I had sat in a coal fire and I left the study with the Beak’s words stinging in my ears, “If you are caught smoking again, it will be twelve strokes on the bare bottom.”

Twelve strokes? On the bare? Was he really permitted to give such a punishment, or was it just a tale he told to naughty schoolboys to stop them from re-offending?

Later as I sat in a lavatory pan of cold water, I vowed never to smoke again: and I never did. Well, not cigarettes: I took up my present tobacco habit (the gentleman’s pipe) five years later when I was up at the university.

I rose from behind my desk and replaced the caning chair to its resting place. I knew Roehampton, Da Silva’s partner in crime as it were, was even now waiting outside my study and the chair could have remained where it was for his thrashing, but I preferred to treat each boy before me equally: the ritual of placing the chair in position was part of the total caning experience (as marketing men might call it) for each boy.

I have a number of options for placing a boy when I cane him. I personally don’t favour the “traditional” position of boy bent down touching toes. It has the obvious advantage that you don’t need props (apart from the cane itself), but if you are properly to beat a boy you should always intend to cause the maximum pain possible, and in such circumstances it is only Christian to give him something to hold on to as he attempts to deal with his agony.

Usually, I have boys bend over the back of a large green leather armchair; the small ones can bend over an arm; while the taller, over the back. The seat cushion removes to reveal stout bars that the victims hold on to. It is both comfortable and very supportive, which means that they cannot move about and escape their just deserts.

Roehampton, my next client is eighteen years old, but, this will be his first caning. He only joined the school at the beginning of the third form (he is some kind of scholarship boy, I believe) and hitherto has managed to avoid corporal punishment. I cannot say whether this is because he is an exceptionally well-behaved boy, or he has just escaped detection for his misbehaviour.

This time he is well deserving of a caning. His academic work has been deteriorating and his subject masters inform me that he will almost certainly do badly in his examinations. In my experience I find this kind of thing happens at this time every year, so I have a purge. Boys in danger of failing are sent to me and I deal with them in the time-honoured fashion.

Was it the Romans who said that a boy’s ears are in his backside? If you want them to study and they will not, then you must force the issue. I don’t suppose any of the boys thank me for it (although some of them do literally say “Thank you, sir” as they hobble from my study) but I have no doubt it was my cane that got many schoolboys through their examinations and on to a half-decent university and beyond.

“Come in Roehampton!” I called from behind my desk. The door of the study inched open, but at first nobody entered. Then, Roehampton’s head appeared around the frame, followed at a snail’s pace by the rest of his body. His face was deathly white and he appeared on the verge of tears. Obviously, he had heard the ferocity of the caning his friend Da Silva had received and I had allowed ample time for the boy to pass on a blow-by-blow account of his thrashing. Roehampton would be expecting no less an ordeal for himself.

“Stand there boy,” I indicated the spot in front of my desk. I was surprised the carpet wasn’t more worn than it was by the scuff marks made by the shuffling feet of generations of naughty schoolboys.

He stood to attention so stiffly I wondered if he were a leading light in the school’s Officer Training Corps.

I never lectured boys if I could possibly avoid it, they came in bent over and took the required strokes then they quickly got up and left leaving the next boy to enter and so on till they had all been dealt with. But, I had to make it clear to Roehampton the gravity of his offence so I began my ritual sermon about unacceptable, disgraceful behaviour – totally unexpected of sixth-form boys who had examinations forthcoming and who needed good grades to secure a place at university.

Then I pronounced sentence: Six-of-the-best. Roehampton’s face had gone rather pale and his lips were trembling as if tears were not far away. “I really am sorry Sir. Please could you let me off this time?”

I suppressed a snort. By way of reply I walked in front of my desk and moved the caning chair into position. I have caned many boys in my time and almost without exception had to position a boy for his first caning. “Right boy, take your blazer off hang it up on the door and then come and stand behind this chair.” I pointed to the green leather chair as if there could be any doubt which one I meant. “Right, now bend over the chair, holding the bars with your hands,” I ordered sternly.

Resigned to his fate and clearly not prepared to beg further for mercy, Roehampton struggled to get into the requested position, while I went to the glass-fronted cabinet and selected a long brown dragon cane. I returned, bending it and whistling it through the air in practice strokes intending to send chills through the teenage boy.

I found him looking at me as he half leaned over the back of the chair as though checking this was how it was to be done. “Head nice and low please Roehampton,” I confirmed.

He grimaced and bent right down over the back of the chair. His firm bottom stretched his now very tight grey trousers, a point I was careful to observe as I positioned myself behind him.

“Stick your bottom out more, boy, hollow your back, legs slightly apart.”

I knew this was the boy’s first caning and I intended it to be memorable. “Roehampton when I cane I make sure it hurts. There is no point in giving a boy a beating if it doesn’t. I won’t lie to you, 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.”

It had the desired effect and tears started to flow freely before I had even cracked the first stroke against his tight backside. He was gripping the bars of the chair so tightly his knuckles must have ached.

I could see the outline of the lad’s buttocks under the trousers and his pants across the bottom nestling deep into the crack of his cheeks. I gripped the cane and took a few steps away. To calm down I took a few “air shots” before finally returning to stand to his left such that with my arm outstretched the cane tip lay half way across the cheek of his further buttock.

I watched him flinch slightly as the rattan touched the middle of his buttocks. I raised it slowly then, setting my face, brought it whistling down. It landed with a satisfying thwack right across the middle of his bottom.

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

The study was again filled with the sound of the cane swishing through the air, followed by that awful crack that signalled another searing bout of pain across his already sore bottom. I drew the cane back for another stroke. The teenager arched his back and screwed his face up as he experienced the smarting of yet another assault to his red raw bottom.

Despite the shocking pain, Roehampton had resolved to take the caning bravely and silently and did manage to hold in the scream for the first blow, and indeed the second, but when slash number three connected with the seat of his trousers he lost all control, his feet started to beat a frenzied tattoo, as his hips twisted and squirmed.

He desperately wanted to jump up and run from the study clutching his buttocks in both hands, but some schoolboy instinct kept him down. He was grateful that he had the rails of the chair to grip on to even though his hands were now grasping them so tightly his fingernails dug deeply into his palms.

The fourth branding was met with another scream and Roehampton was now audibly muttering: “No!” and “Please!” I stood back took aim again and the cane flashed through the air with a whoosh and the resulting blow snapped into Roehampton’s waiting backside with venom.

Bawling continuously, he waited for the final crack which I put right across the middle of his buttocks, angled, so that it crossed about three of the other cuts.

It took some time after the last stroke for him to realise the ordeal was over. “Yes,” I sighed. “That concludes your punishment, Roehampton. I hope you have learned your lesson.”

Like so many thrashed schoolboys before him, Roehampton remained slumped across the back of the chair, just trying to absorb the line of fire across his bottom. Nothing his pal Da Silva had said about being caned had prepared him for the pain or for the feeling that his bottom had being cut into slices and then set on fire.

“Up boy!” I commanded. Eventually his hands scrabbled for the arm of the chair and he pushed himself upright, panting and sobbing as I wrote the relevant entry in the punishment book. As I said previously I prefer a boy to take his caning and leave the study without fuss.

He danced on the spot, clutching the seat of his trousers. I knew beneath them there would be six vivid and very painful stripes decorating his hindquarters which would be felt every time the boy sat down for days serving as a constant reminder to study hard in future.

I offered him the punishment book to initial, which he did with great difficulty; his tears were still flowing freely.

“That will do for now,” I said quietly and correctly he took this as his cue to leave my study.


This story was first uploaded in August 2015

Picture credit: Unknown

More stories from Charles Hamilton II are on the MMSA website

Charles Hamilton the Second


How Many Strokes Will it Be?

z used cane holding (15)

Newbury wondered how many strokes it would be. He stood to attention, heart beating far too quickly, watching through rapidly blinking eyelids as the headmaster made his preparations. Dr Fortescue had been at the school less than two weeks. Already the boys had Christened him The Tyrant Headmaster.

Newbury sucked in a lung full of air. The room was stifling; not hot, but airless. Did the headmaster ever open the windows of his study? Dr Fortescue ruled the school with a rod of iron. No, that was not quite true, he ruled with rods of bamboos, Malacca, rattan and ash. Newbury stood in silence. Dr Fortescue busied himself at a cupboard. His collection of canes was extensive, he must select just the right one for the job in hand. He took one, dark yellow in colour, dense but whippy, three feet and more in length, a traditional crook handle. He swished it through the air, then flexed it between his hands. It was as if he had never met the rod’s acquaintance before. He peered at it intently, stone-faced; his white moustache bristled and his knitted white brows frowned.

Newbury licked his dry lips, waiting patiently. Dr Fortescue was an elderly man dressed in an old-fashioned, untidy academic gown. He was a commanding figure, rumour was he had once played prop forward in rugby. He was a tall, grim man and as strong as an ox. The senior boys of St Septimius could testify to that.

The headmaster had made it his business to raise standards from the moment he arrived. The school was going downhill, it needed drastic action. That was what the governors had told him when they appointed him. “Clean it up man,” were his orders. So, he started at the top, with the sixth-formers. Many of them, like Newbury, might be eighteen years old but they were still school pupils, still children. And they had better not forget that.

Newbury watched intently as the headmaster replaced the cane in the cupboard and selected another. To Newbury it looked exactly like the one he had returned, but the headmaster seemed to discover new properties it. He let it fly through empty air. It made a terrific swoosh! It looked like the one Dr Fortescue had used to thrash Rodriquez on his very first day at the school. Newbury blanched at the memory. Rodriquez prone across the table in front of the entire sixth-form, trousers down, buttock cheeks stretching his tight, white underpants and the headmaster flogging that very same Dragon cane into the firm young bum. Newbury clasped his hands behind his back to stop them shaking. The memory of his pal was all too recent.

The agony of the caning was so great Rodriquez had leapt to his feet. Two sixth-formers were ordered to hold him down, then the headmaster slowly bared Rodriquez’ bottom and whipped him with all his force. He had to be half-carried from the room at the end.

Newbury coughed dryly. Dr Fortescue had selected his weapon of choice, now he was making his preparations. The teenager took close note of how the headmaster’s arm muscles tensed as he picked up a heavy straight-backed chair and set it down in the centre of the room. His shoulder muscles tensed when he gripped a second chair and manoeuvred it so it stood back-to-back with the first. Satisfied they were in the required position, he ambled across to the bookcase and selected the first volume of the Encyclopaedia Britannica. It was a heavy book and several inches thick. He knew it would do the job in hand. He had no intention of reading it, he turned, walked across the study and set it down on the hard wooden seat of the first chair. Then he rested the cane on the top of his desk.

“Thieving Newbury,” Dr Fortescue snarled. “Such disgraceful behaviour.”

Newbury stared down at his shoes, embarrassed into silence. There was nothing he could say. He had been caught red-handed filching cigarettes from the corner shop. He wore his distinctive blue and white school blazer, there was no escape.

The headmaster frowned, his white whiskered quivered. “Theft is crime. You should go to court. You will have a record,” he leaned forward and Newbury recoiled. “There goes your place at university. Any hope of a decent career. You stupid, stupid boy.”

Tears formed behind Newbury’s eyes. Criminal record, a life ruined. It had never entered his head.

The headmaster paced the room slowly, tutting to himself; like so many schoolmasters he was a ham actor at heart. “But, Newbury,” he took hold of a hem of his gown and swished it across his body, rather like a magician about to complete a trick. “Help is at hand.” He straightened his back, shoved his shoulders forwards and (he liked to think) rather like his hero Winston Churchill, he barked, “Mr Scrimshaw, the shopkeeper, has agreed not to go to the police.”

Newbury’s heart skipped, this time with something approaching joy, not terror. “He will not press charges, if he is to be present at your beating.” The headmaster  strode to the door of an anteroom and with a flourish opened it. “Come in please, Mr Scrimshaw.”

A wizened man, hunchbacked, with a long sharp nose and pointed nose, shuffled into the room. His beaky eyes peered around the room as if he had transferred from a dark cave into a brightly-lit room. He stopped three feet in front of Newbury and very deliberately he examined the boy’s features as if ensuring that he was indeed the culprit who tried to make off with then Woodbines without payment.

“Please sit down Mr Scrimshaw,” the headmaster indicated a small comfortable armchair. Scrimshaw coughed a response and wheezing all the time settled himself down. He shifted his buttocks for comfort and leaned forward menacingly. He was making sure he had a perfect view of the drama about to unfold.

The headmaster picked up his cane and flexed it between his hands. “Whip him well Mr Headmaster, whip him well,” Spittle dribbled over Scrimshaw’s bottom lip. The headmaster’s eyebrows shot heavenwards, “Oh, I intend to Mr Scrimshaw, I intend to.” He turned toward Newbury and swished the cane through empty air, then pointed it at the two straight-backed chairs. “Stand there boy!”

Newbury clutched his hands behind his back, rather like the Duke of Edinburgh on a walk-about. Dr Fortescue stood close to him casting a show over the sixth-former’s body. Newbury caught the masculine aroma of stale whiskey, cigarette smoke and coal tar soap. “Lower your trousers and your underpants.” It was a simple, calm instruction. There was no need to engage in histrionics,  the headmaster was in charge, and he knew it.

Newbury turned his head slightly toward the headmaster, a look of incomprehension on his face. Dr Fortescue sneered, “Get on with it boy. Right down to the ankles, if you please.” Newbury’s head pounded, blood was rushing through his arteries to his temples. He felt unsteady on his feet. He gulped in air, afraid that he might faint to the floor. At last he got his shaking fingers to cooperate with his brain and the front of his trousers opened. He sensed Mr Scrimshaw lean forward in his chair.

Of their own accord the trousers slipped down his thighs and past his knees and settled in a puddle on top of his shoes. His white Y-front underpants were a little small and hugged the contours of his buttocks and cock. The musky aroma of the headmaster wafted into his nostrils. He gulped down saliva, slipped his thumbs into the waistband of his pants and guided them south. He had to bend his knees as he took them on their way, suddenly conscious that his bare bottom, crack and balls were on full display. A strange combination of a wheeze and a sneeze escaped Mr Scrimshaw’s mouth.

Newbury stood naked from the waist down, the long-ish tail of his shirt covering his privates and buttocks. The headmaster tapped his cane on the top of the encyclopaedia. “Lift up your shirt, kneel on the book and bend across the chairs.” Newbury stared at the cane in the headmaster’s right hand. It was about three feet in length, darkish yellow in colour and with the traditional crook handle. It was dense and had notches every three or so inches along its length. It was a terrific weapon, Newbury wondered if he might be permitted to stuff a handkerchief into his mouth.

“Over boy,” the headmaster’s patience was exhausted. He thwacked the cane across the book. Still, unsteady on his feet, Newbury gripped his shirt and hauled it up to his chest while simultaneously climbing onto the chair. The book was to rise his body so that his backside would be high, and as his body stretched across the chair backs, his buttocks would be at the correct height and angle to receive lashings into the underside (and most sensitive) part of the cheeks.

“Head down, bottom high,” Dr Fortescue intoned. Newbury wriggled into the required position and waited, conscious of his submissive position. His naked buttocks were twitching submissively, completely at the mercy of the powerful headmaster. There would be no mercy  that afternoon. Newbury was resigned to his fate.

Dr Fortescue stood a cane’s length from Newbury’s left side and began to saw the cane across the underside of the cheeks. He had beaten many buttocks in his career as an educator, the pair offered up to him now were quite typical. Newbury was well covered. He was in no way ‘fat’ but his bum has a certain amount of ‘give’ as the headmaster pressed his cane into the flesh as he took his aim. He tapped the cane smartly against a dimple that had formed under Newbury’s left cheek. The headmaster counted to five in his head, raised the cane high and with a strength nurtured over many years flogged the whippy rattan with maximum force across the centre of both cheeks. He was greeted by a thick dark pink line across the otherwise unblemished skin.

A hissing sound like a steam engine whistled through Newbury’s clenched teeth. He hands gripped the seat of the hard wooded seat. His back bucked, his head rose and fell. That hurt. That hurt a great deal. He heard the floorboards of the study creak as the headmaster paced. “Thank you Sir, may I have another,” Newbury spoke firmly. The headmaster paused pacing and glared. “What?” he did not say out loud. “I have never come across such a thing before. Such impertinence.” He took aim and the cane whistled as it flew though the air, the crack of rattan on stretched flesh bounced off the walls. Newbury repeated the buckling and the bouncing. This time a sharp yelp rang out. The headmaster paced.

“Thank you Sir. May I have another,” croaked this time. Dr Fortescue’s face, never clear at the best of times turned puce. “What!” again thought but unsaid. “Is he saying my flogging is not hurting? He can take anything I might offer?” The third lash struck across the top of the curves; there were now three livid red welts running almost parallel across Newbury’s buttocks. The headmaster had a terrific aim. He was (as it were) a master master. “Thank you Sir, may I have another.” The headmaster paced the floor, this time noticing Mr Scrimshaw was himself red of face. He was leaning forward elbows resting on knees stretching himself to get as close to Newbury’s prone body as possible without actually leaving his chair.

The headmaster tapped his cane ready for the fourth stroke. Perspiration soaked Newbury’s short hair, it looked as if he had just emerged from the swimming pool. The eighteen-year-old’s face was deathly pale. His knuckles were turning white, the muscles of his arms were taut as he gripped the chair for dear life. All saliva had drained from the headmaster’s mouth. He ran his tongue around it trying to make some moisture, tasting a tang of whisky. He took a deep breath, found his aim and whacked the cane across Newbury’s dimple. There was no yelp this time; the boy had shut his teeth together with such force he feared they might crack. The thumping at his temples had disappeared replaced with a light-headedness he had never experienced.

“Thank you Sir. Please may I have another,” his voice sounded as if had travelled from miles away. It did not sound to Newbury as if the words were his. The headmaster paced. Perplexed. Never in his life had a boy asked for more. By the fourth stroke many a boy – seniors as well as juniors – would be begging for mercy, promising to do anything if only the headmaster would stop the beating.

More pacing followed by more tapping. Swish! Crack! “Thank you Sir. Please may I have another.” The intense agony had started at the buttocks and then travelled up and down his legs; soon his whole body ached with pain. But by cut number five something unexpected happened. Newbury heard the swish, he felt the cane sink into his flesh and then … Nothing. There was no pain. The boy lay breathing heavily. Was his body now so numb that he was immune? “Thank you Sir. Please may I have another.”

The headmaster paced. Number six. Six-of-the-best. The very best. Dr Fortescue always finished on a high note. His special headmaster’s caning had already become infamous at the school. Newbury was not surprised to feel the headmaster alter his position. Now, instead of tapping the cane from left to right across the bared bum, he laid it in a diagonal from the bottom left to the top right of the buttocks. He let fly. A thick red line intersected the previously-laid five, reigniting and adding to the severe pain already inflicted. Newbury hung on. His mind was playing tricks. It was as if were floating on the ceiling looking down at himself submissively positioned across the chair, buttocks blazing. The headmaster, a little unsteady was at his cupboard replacing the cane along with his collection. Mr Scrimshaw rocked gently back and forth in his chair.

The headmaster sat at his desk, opened a drawer and pulled out a hard-covered exercise book. He fished in the inside pocket of his jacket and pulled out a pen. All this time Newbury lay still, trying to figure out this feeling. Was this how it felt to take drugs? The headmaster found a page in the book, wrote some words and closed it. Still seated he called to Newbury, “That’s it. Get up and get dressed.”

Newbury climbed from the chair and un-self-consciously massaged his buttocks. He swivelled his body and saw six impressive welts. Mr Scrimshaw stared at him intently as cautiously Newbury rubbed his index finger across the lines. His bum felt like corrugated cardboard. The headmaster sat back a little in his chair observing his senior pupil.

Newbury turned his back to Dr Fortescue then bent down to retrieve his underpants. It gave the headmaster an uninterrupted view of his savaged buttocks, his crack and hole and his ballsack. Newbury took a moment more than necessary to get his pants back in their rightful place. He turned and faced the headmaster’s desk. His cock was hard and fought against the already stretched cotton. He looked directly at the headmaster who could not return his gaze. Newbury pulled up his trousers and buttoned up.

And that was how Newbury came to worship Dr Fortescue with all his heart and soul.

Picture credit: Unknown


More stories involving The Tyrant Headmaster are here.


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More stories from Charles Hamilton II are on the MMSA website

 Charles Hamilton the Second


Don’t Knock it Until You’ve Tried

zused drawing paddle hold cane cupboard (1)

Jake stared at the message on the screen of his iPhone. Finn was late but on his way. Jake hated sitting in The Three Fishers on his own. The pub was heaving. It was a bit of a sleaze ball. They had begun drinking there when they were sixteen; they weren’t particular about who they served. A group of old queens at the bar scanned the room searching for fresh meat. Jake felt their stares burning his flesh.

He concentrated on his phone, swiping through the sports news. He didn’t hear the man at first. “Sorry,” he shouted leaning forward to hear what he was saying.

“I said, do you like being spanked?”

Jake frowned, had he heard the old man correctly?

The man edged closer and put his mouth close to Jake’s ear. “Would you let me spank you? Are you in to being spanked?”

Jake’s mouth opened and closed. He had heard all right that time. What sort of question was that? Who was this man? He didn’t seem drunk. High. Crazy.

“I have a house. Lots of toys,” the man smiled.

Jake took a long draw on his drink. Playing for time. Just a little frightened. Bodies pushed past his table. He looked across to the door. Should he leave? Where was Finn?

“I can spank you. Do you like to be spanked?” the man asked again as if it was the most natural question to ask a guy in the pub. (“Do you want a peanut?”)

Jake took another gulp of beer. Dutch courage. “Wor … wor ..” he began, trying to find the right word. How to say “fuck off” without making a scene? He looked the man in the face. It was a bright, open face. Not at all sinister. The guy was no threat. Jake laughed. “Jesus. Does anybody ever say ‘yes’?”

The man’s smile was genuine. “You’d be surprised. But, not for you then?”

Jake shook his head, “No thanks.”

“Oh well, enjoy your evening. But if you ever change your mind …. ” The man disappeared into the crowd.

Five minutes later Finn put two pints on the table in front of his pal. He took a long draught, downing half of the glass.

“You’ll never guess what’s just happened to me?” Jake said and when Finn ignored him, he told the story anyway.

“I guy came up to me and asked if he could take me home and spank me. Incredible!”

Finn took another gulp. Shrugged his shoulders. “About fifty, greasy hair, going a bit bald, bit of a Welsh accent?”

“You know him?”

“Name’s Paddy Price. Least that’s what he calls himself.”

“How do you know him?”

Finn smirked, “How’d ya think?”

It took a moment for the penny to drop. “You’ve been with him?”

Finn snorted, drank some more. “He has a big place on The Avenue. Must be loaded.”

Jake stared at his friend. The room seemed to be spinning. What was happening here? “What he paid you?”

Finn’s nostrils flared, “Fuck off, what do you take me for a rent boy?”

Jake recoiled, Finn was genuinely angry. “No, but,” he paused, uncertain whether he should say this. “But isn’t it gay?”

Finn frowned, Jake could be a right dickhead sometimes. “No.” He nodded at the iphone on the table. “Go online, everybody’s into it.”

Finn was right. Later in bed Jake surfed the net. They were all at it. Guys on girls. Girls on guys. Girls on girls. Guys on guys. An entire industry of adult spanking. In one video there was a guy looked a bit like Finn. He wasn’t, of course, but he was the same height, same basic shape; not fat, but cuddly.

He was supposed to be a junior schoolboy, short trousers, knee socks. The lot. He had been found smoking a cigarette. Then he had to take down his shorts and underpants and bend over the knee of another lad who was the head boy to get a spanking on the bare bottom.

In another one the same Finn-a-like (still a schoolboy in short trousers) is caught smoking. In these videos smoking is the biggest sin a schoolboy can commit. Its shorts and trousers down again. This time he’s over the back of an armchair for a dose of a whippy rattan school cane from the headmaster.

Jake slept so fitfully the duvet was soiled. He dreamt he was back at school and Finn was head boy and Jake was that boy getting his bare arse slapped.


Nearly two weeks later Jake walked purposively through the suburban streets. The Avenue was longer than he had anticipated, if he wasn’t careful he would be late for his appointment. Paddy Price had ben most helpful when after three tries Jake had at last tracked him down at the Three Fishers. Of course, they could meet, let us make an appointment. Is an evening good for you? It was as if they were arranging to meet for tea.

At last Jake found the house. It was a modern structure hidden behind a high wall and electronic gate. Away from prying eyes. He touched the intercom button and a cheerful voice greeted him With a whir the gate moved sideways and Jake squeezed through. Paddy Price was waiting at the door, a bright welcoming smile split his face.

They chatted amiably. Did he find the house all right? All the while Jake’s heart pounded. He had been waiting for this hour. Once Finn had introduced him to the joys of spanking videos Jake could not get enough. He sweated waiting for his chance. Oh to go across the back of a chair, or over the knee for an arse-whopping. His temples ached already at the prospect.

Paddy Price led the way upstairs. “I have a special room,” he grinned opening a large wood-panelled door. “It’s sound-proofed,” he said enigmatically. It was a large room, dominated by a huge beaten-up wooden desk. Along one wall were glass-fronted bookshelves. A black leather Chesterfield couch rested against another. A wardrobe with double doors was along a third. Two padded leather armchairs made up the rest of the furniture. Paddy Price gestured to one of them, “Sit down, please.” He noticed Jake’s wide eyes drink in the contents of the room. “Sometimes I use it as a headmaster’s study,” he explained. “Some people like to do role-play, you known blazers, school caps, shirt trousers, the works.”

Jake nodded without enthusiasm. He had noticed in the videos how the “schoolboys” almost always wore short trousers. It did nothing for him personally. Paddy Price perched his ample buttocks on the edge of the desk. He smiled again. “Have you given any thought to tonight?” he asked. Jake gulped, he had thought of nothing else for days. It seemed for every waking moment (and some also while he was asleep).

Paddy Price pulled himself to his feet and ambled to the cupboard. He opened it with a flourish. Jake’s eyes popped. “Voila! My toys,” Paddy Price stepped to one side, giving his guest the full view. Dangling on hooks was an array of straps, paddles, canes and crops. “Something for everyone,” Paddy Price’s lips parted revealing yellowing teeth. “Oh and I have slippers and brushes too if you’d rather.”

The tip of Jake’s tongue poked out and he wetted his lips before clamping his top teeth over his bottom lip. He swallowed hard.

“Do you have a preference?” Paddy Price grinned, “Or would you prefer me to choose?” Jake sat and stared. Speechless. “Never mind,” Paddy Price resumed his spot on the desk, “We have plenty of time.”

They lapsed into amiable silence. Paddy Price was in no hurry. He adored breaking in “newbies”. H would go at Jake’s pace. “Of course,” he said mildly, “It is so much more fun if the discipline is a real punishment,” he noted Jake’s bafflement so continued, “Have you been naughty? Is there something you have done that is bad?” Paddy Price leaned forward hoping to entice his guest into confession.

Jake pondered. No, he thought, he hadn’t done anything that he could recall. Paddy Price flashed his smile once more, then laughed, “Oh, so we have a saint here, do we, ha, ha, ha.” Jake blushed but remained silent. “Have you taken any drugs? Smoked weed?” Paddy Price asked.

“Yes,” Jake replied unsteadily.

“Well, that’s bad. That’s against the law,” Paddy Price beamed. “You should be spanked for that.”

Jake blinked. Smoking weed, against the law? Of course, but he had honestly forgotten that. Everyone he knew smoked, all the time. The police never did anything about it.

“Right then lad,” Paddy Price’s smile had gone. He rose from the desk and paced across the room. “Stand up. Stand in front of my desk,” he barked as he sat himself down behind it. “Stand up straight. Stop slouching.”

Jake straightened his back and let his arms hang limply by his side.

“Look at me when I’m talking to you,” Paddy Price’s entire demeanour had changed. “I will not tolerate one of my boys using drugs. They are dangerous. They are against the law.” Jake nodded, uncertain how he should react. His heart was racing and he could feel blood rushing to his temples. Adrenalin was kicking in.

“What have you to say for yourself, boy?” Paddy Price had a script in his head. Jake mumbled, said nothing coherent, then clasping at straws he muttered, “Sorry,” and then after a moment’s further thought, he added the obligatory, “Sir.”

“Sorry!” Paddy Price’s voice rose an octave, “Sorry! You soon will be boy.” He rose from his chair and magisterially walked to the still-open cupboard. He paused, turned to Jake and barked, “Hang your jacket on the door.” He nodded to a hook. With damp palms, Jake slipped the jacket from his shoulders. He surprised himself at how much his hands shook.

He turned to face his master in tie to see Paddy Price pick out a cane from the cupboard and swish it through the air a couple of times. Then he held the two ends and flexed it gently testing it for whippiness. It curved easily. It was about a metre in length and as thick as a pencil. It looked just like the ones Jake had seen in the videos. It had notches along its length and the traditional curved handle. All saliva drained from Jake’s mouth.

“Boy when I cane I make sure it hurts. There is no point in giving you a beating if it doesn’t. I won’t lie to you, 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,” Paddy Price was enjoying himself. “Now, I want you to stand behind that armchair,” he swished the cane in the required direction so there could be no doubt what he meant. With legs of lead, Jake shuffled the three steps needed to comply with the order.

Paddy Price stood flexing his cane thoughtfully between his hands. “Lower your trousers,” he said sternly. Jake hesitated. His head was light, Paddy Price’s voice sounded as if it was travelling from a vast distance. Paddy Price tapped the end of the cane across the back of the padded armchair, making a series of dull thuds. As if in a trance, Jake fumbled to unbuckle his belt. His hands moved more freely as he slipped the fastener and unzipped his trousers. The weight of the belt and gravity made them slither down his thighs and rest at his knees. “All the way down,” Paddy Price growled. Jake stooped forward and pushed them to his ankles.

He straightened himself in time to hear Paddy Price intone, “Now, your underpants.” There was a thundering noise in Jake’s ears, his temples throbbed, his head ached. He looked down at his gleaming white Y-fronts; he had bought them specially for the occasion; all the boys in the videos wore them. He put his fingers in the waist band and peeled them down, exposing his cock and balls. He left them bunched just below his buttocks. Instinctively, he placed both hands at his from to hide his genitals. “Pah!” Paddy Price wheezed, unimpressed.

He swished the cane through empty air once more, it made a terrific whooshing noise as it flew. “Bend over the chair,” he touched the top of the armchair with the cane for emphasis. A feeling he had never felt before overwhelmed Jake; he could not be certain, was this fear? Or was it extreme excitement. He bent forward feeling his bottom tighten into a smooth curve. His bare buttocks were presented submissively over the back of the armchair.

“Head nice and low please boy.”

Jake’s thigh muscles and bottom tensed as he stretched his arms grasping the armchair’s cushion at the front. Paddy Price watched quietly as the teenager slithered into position. Then he gently took a grip of Jake’s underpants and tugged them so they fell to rest on top of his trousers. He was almost ready. Paddy Price heard Jake’s heavy wheezing and smiled. He lifted the nineteen-year-old’s shirt away from his backside, exposing me, so that his body was naked from the middle of his back to his ankles. Jake shivered; not with cold but fearful anticipation.

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

Jake pushed himself further down into the chair, raising his bottom well up for the cane.

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

“Yes, Sir,” Jake’s reply was muffled as his head was buried in the chair cushion.

Seconds passed. Only now did Jake realise his master had a perfect view of his crack and hole. And Finn had said there was nothing gay about this. Jake’s hole winked, opened and closed, his buttocks quivered, then clenched. Never in his life had he felt so vulnerable. Suddenly there was an enormous noise. The thwack of the cane landing on Jake’s backside echoed round the room. Jake hardly had time to recover from the shock when there was another crack which this time was immediately followed by an intense burning pain. He held his breath as the next stroke landed causing the pain to increase in a sickening wave.

Number four stuck and Jake hissed a whine. Mr Price continued, determined. Three more strokes landed each one lower than the previous, yet all in a band about three centimetres wide on the lower half of Jake’s bum. As the next stroke cracked across his poor sore seat Jake let out a roar, any restraint he may have had was gone. He could no longer see the chair for the tears filling his eyes. Jake closed his eyes and gritted his teeth and hung on to the chair, aware of nothing except the pain burning like a furnace in his bottom.

Raising his arm high Paddy Price brought the cane down with a full swing, landing in the middle of Jake’s bottom. He cried out and tossed my head, humped the back of the chair and swayed for a few moments. The next three strokes seemed to merge together. Jake was concentrating on staying bent over, in so much pain, and trying without success to stop the tears that were by now flowing down his cheeks.

He desperately wanted to but he did not stand up. Instead he remained bent over the caning chair offering his bottom for the next stroke, completely at the mercy of Paddy Price, who could make each stroke as severe as he wished and all Jake could do was accept it and then wait for the next.

Paddy Price was in his element, he was an expert caner, a master master if you will. He swished in yet another stroke across the very centre of Jake’s bum. Although he still stayed over the chair, his feet beat a frenzied dance, his hips twisted and squirmed.

Jake thought his head might explode; blood coursed through his arteries. His bottom felt like he had been sitting on a barbecue. His arse felt corrugated; welts criss-crossed his once creamy-white buttocks. He was certain some might be weeping blood. How many strokes had it been? Jake had not thought to count. What was certain was it was more than a simple six-of-the-best. Finally, Paddy Price walked over to the cupboard to replace the cane. Jake felt a terrific sense of relief that it was over but remained across the chair, breathing heavily and in great distress.

Paddy Price stood watching the teenager gasping for breath, like some beached dolphin. He had taken it well. “It’s over. You can get up now. I think you have learned your lesson, haven’t you?”

Jake slowly pushed himself back on his elbows and rose unsteadily. His legs felt weak and he had to lean on the desk before he got his balance. Tentatively at first, he touched then carefully clasped his raw buttocks and began kneading them, as though he could somehow squeeze the pain out. Only then did he see his rigid cock staring at a forty-five degree angle to reach the ceiling. His head was the clearest it had ever been, like an out-of-body experience. No amount of weed would ever give him a buzz like this.

Slowly, painfully, he pulled up his underpants, staining to get the soft white cotton to cover his cock. Still he massaged his injured rump as vigorously as he could.

Paddy Price slipped his arm around Jake’s shoulder for an instant, before propelling him towards the door, and out into the hallway. His eyes were still wet and blurry, but he found his way to the bathroom where he stayed for the few moments it needed for his cock to explode into a wodge of toilet paper.

“Come down, for a drink,” Paddy Price called, “When you’re quite ready of course.”


Picture credit: Unknown

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More stories from Charles Hamilton II are on the MMSA website

Charles Hamilton the Second

The Moped Gang

By Charles Hamilton II and Cayenne.

The headmaster leaned forward in his chair, rested his arms on his desk, clasped his hands together and stared intently at the five sixth-formers standing before him.  His unkempt moustache bristled as he sneered, “Well, well, well, Gentlemen, welcome! I seem to have convened an impromptu meeting of the Moped Gang!”

All five eighteen year olds stared blankly, trying with varying degrees of success to look unconcerned. It would be a lecture, of course. Mr Lynch would lambast them about their behaviour and send them on their way. Maybe with an essay to write, Why I should be a credit to the school, something like that.

The headmaster shook his head wearily. “The five lads from my school who have been terrorising the neighbourhood.” Juvenile delinquents, he told himself. They were mighty fortunate not to be up before the Magistrates’ Court. Out loud he said, “You have been inflicting your loutish behaviour all over the neighbourhood.”

He paused, waiting for a reaction. When none came, he carried on. “You have been riding those infernal mopeds disturbing all and sundry.” He suppressed a smile. Mopeds; bicycles with hairdryers for engines. Hardly the Hells Angels. Nonetheless the good name of the school was at stake. “You have been smoking and drinking and,” the headmaster shuddered at the thought, “urinating in most inappropriate places. The churchyard and the gardens of the Masonic Hall, I hear. And often you are foolish enough to do this in school uniform! You are a disgrace!”

Mr Lynch hauled himself to his feet. He was a stout man, some would say he was running to fat. At six feet, he was taller than any of the boys standing in his study. Five pairs of eyes watched him intently as he shuffled across the room towards a bookcase. It ran most of the length of one wall and had glass doors. The shelves were stacked with history text books. Mr Lynch liked to keep his hand in in the classroom. A tall thin cupboard divided the bookcase. He fumbled in his pocket for barely a moment before bringing out a key. His hand trembled as he inserted it in a lock and opened the cupboard. His body obscured the boys’ view but an unmistakable rattling sound revealed its contents.

Mr Lynch turned to face the delinquents. “It’s a shame that you are all eighteen and so too old for this cane of mine.  Isn’t that so, Smith?” The headmaster held the rod between his hands and flexed it.

“Err, yes, Sir,” Smith blustered.

The headmaster swiped the cane through thin air. “Too old for this cane, Passey?”

“Yes, Sir.” Passey stared intently at the cane. It was a little over three feet long with a curved handle.

Swish! The cane flew again. “Too old, Wilkinson?”

“Yes indeed, Sir,” the lad coughed nervously, sensing some kind of trap.

Mr Lynch took a step forward, leaning into a thin, lanky boy. “And how about you, Jenkin, just turned eighteen, I believe, so too old for this cane of mine?”

“Yes, Sir, Mr. Lynch, Sir.” Jenkin returned the headmaster’s gaze. He wished he would just get on with it. An essay. A detention even. He wanted to get away, the Moped Gang had a meet that evening.

Mr Lynch swivelled on his left heel. “And finally, we get to you, Davies.”

“Yes Sir?” a short, stocky boy narrowed his eyes. He didn’t understand the tone in the headmaster’s voice.

“You’re a little bit different from the others here, aren’t you?”

“I am, Sir?” He felt his cheeks flush, what was the Old Man talking about?

“Oh yes! You may be eighteen like the others here, but I understand that your father beats you regularly. With a cane just like this!” He swiped it twice through the air for emphasis. “He told me all about it when we were at the Model Railway Club. We are both members, you see.  He’s the life and soul of the club, old ‘Deltic’ Davies, you know. He often tells us he’s had to get his cane out.”

Jenkin suppressed a snort. The cane, from his dad, he thought. Wait until he told the other sixth-formers. Davies’ face reddened with embarrassment and shame.  He felt no shame being up before the headmaster, but for the Old Man to know he was caned at home; that was unbearable.  And now, the shame that his friends had just found out about it too.

But there was more. The shame that his father played trains! Diesel trains too. And Dad was friends with headmaster. That had to be the worst! No, wait! Did the headmaster know that Davies had his trousers at his ankles and his underpants at his knees as he bent across the dining room table for lashes from Dad’s cane across his bared bottom?

What if all of that became public? It would be the end for Davies. How could he remain leader of the Moped gang? Davies stared at his scuffed shoes. He couldn’t look the headmaster in the eye. Neither could he look at his mates. He knew inwardly they were smirking. He wouldn’t hear the end of it once the headmaster released them from his study.

Mr Lynch flexed his cane some more, he tapped it gently against his right leg, then he swished it through the air again. He knew he was an old ham. This was supposed to intimidate a boy. Usually it worked. But maybe not this time, he thought. Davies’ face was scarlet, but the other four seemed unconcerned.

“So we’re all agreed that you are all too old for this cane of mine?” Mr Lynch’s moustache quivered as he bared his yellow teeth in a smile. There was a murmur of agreement from the boys.  Davies sighed a little too loudly and the headmaster shot him a withering look.

“I have decided,” the headmaster continued, “that you are right. At eighteen, you are all much too old for this cane.  For this junior cane.” He swiped it through the air again. It made a terrific Whoosh! as it travelled. “No, what you lads need is the senior cane. Just right for your sturdy rumps! Jenkin! Go and ask Miss Glossop for the senior cane. Here, you can take this junior one back with you.”

Wilkinson had been right, the headmaster had been playing them for fools, and they were trapped in his game. Jenkin took hold of the cane. It was surprisingly light. He had never seen a cane up close before. Brocklehurst Grammar was a traditional school – traditional curriculum, uniform, sports, religion and above all traditional discipline. And, that meant the whippy, crook-handled rattan cane. Could there be any boy in the sixth-form who had not offered his stretched backside to a master for a stinging six-of-the-best at some time during his school career? Jenkin was an exception; he had only joined the school the previous year after his father moved to the town with his job. This would be Jenkin’s first caning; an experience he did not relish.

Miss Glossop, the headmaster’s secretary, sat in an anteroom perched over her typewriter. Her long, thin nose and shiny black hair made her look like a crow. Jenkin shuddered as he handed the cane over. “He didn’t use it then? I’m surprised!” she barked disdainfully. If she had her way all five boys would be in front of a school assembly bent across a long table while the headmaster flogged their naked buttocks. And, she, Miss Glossop, would be seated in the front row.

“He was very annoyed. Is he going to expel you?” she asked.

“No, no, nothing like that. At least I hope not. He told me to ask you for the senior cane.”

“Ah, of course!” Absent-mindedly, she ran the tip of her tongue across her bottom lip, leaving behind a trail of spittle. “That makes sense. He really is annoyed with you then. The senior one is reserved for the wickedest of the wicked. You bad lads!”

She rose from her swivel chair and sashayed to a tall metal locker at the far end of the room. Jenkin watched mesmerised as her bottom wiggled suggestively. She unlocked the locker and withdrew the cane. Just as the headmaster had done, she flexed the rod between her hands. Blood rushed to Jenkin’s cock. A sudden vision of himself bent across Miss Glossop’s desk, trousers and pants at the floor, made the cock stiffen. Hurriedly he clasped his hands together and held them in front of his balls.

“Here it is then. The senior model. Extra painful.” Miss Glossop narrowed her eyes and handed the stick over. “Be sure to tell the headmaster that there are a couple more in stock in case this one breaks.”

“Err, will do Miss Glossop,” he blustered. He took the cane, unsure how to handle it. It was a little longer and thicker than the junior cane. At first he took it be the curved handle and let it fall by his side. It was long enough to touch the ground and reminded him of a walking stick. That didn’t seem right, so then he gripped it half way down. It was a sturdy rod with notches every four inches or so along its length. It was awesome; it would pack one heck of a punch. For one absurd moment he thought of Charlie Chaplin and how the clown would twirl his cane in the silent movies.

“You’d better be getting back,” Miss Glossop said grumpily. Jenkin jerked back into life, tucked the cane under his arm rather like a sergeant-major did and returned to the headmaster’s study.

“You four,” the headmaster waved his arm, “stand and face the bookcase.” He watched as the teenagers shuffled into place, no longer unconcerned. “Jenkin,” he pointed with the cane to a worn armchair. “Bend over.” Manufacturers called these chairs “comfy” or “comfortable”  chairs but Mr Lynch was determined that Jenkin’ visit would be anything but comfortable. The chair was old and worn. The material on the apex of the back was shiny with age. How many boys had contributed to that, Jenkin wondered.

“Bend over, lad,” the headmaster had had his little joke with the boys, now he was anxious to get on with it; the sixth-formers less so. Jenkin stood a foot or so away from the back of the chair. How exactly was this done? He took a deep breath rubbed the palms of his hands together and reluctantly fell forward, rather like a diver going into an icy pond. Jenkin was so small and the chair so tall, that his stomach rested easily on the top of the chair’s back. He felt his pale-grey trousers ride up his buttocks. He couldn’t see himself, but he was sure the material had separated his cheeks.

“Legs further apart. Up higher.” It was a calm command and Jenkin obeyed without question and struggled to get into the requested position. “Head nice and low, please.” Now, his bottom was resting at a perfect angle to receive a thrashing from the headmaster. Jenkin gripped the seat cushion and closed his eyes. He had never been caned before and nor ever spoken to a boy who had been. His previous school had been quite liberal and corporal punishment was unheard of. His buttock cheeks clenched. He had not meant to do this, it was as if his body was trying to find a natural way to protect him from the pain ahead.

“Relax lad. Relax.” The headmaster “sawed” his cane across the underside of Jenkin’s now upturned bottom. He was finding his spot, taking his aim. Jenkin’s firm bottom stretched his now very tight grey trousers, a point the headmaster was careful to observe as he positioned himself behind him.

“Stick your bottom out more, lad, hollow your back. Mr Lynch knew this was Jenkin’s first caning and he intended it to be memorable. “Jenkin when I cane I make sure it hurts. There is no point in giving a boy a beating if it doesn’t. I won’t lie to you, 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.”

It had the desired effect and tears started to dampen Jenkin’s eyes before the first stroke had cracked against his tight backside. He gripped the chair cushion so tightly his knuckles ached.

The headmaster grasped the cane and took two steps away. To calm down he took a few “air shots” before finally returning to stand to Jenkin’s left. Then, with his arm outstretched he lay the cane tip half way across the cheek of the teenager’s further buttock. Jenkin flinched slightly as the rattan touched the middle of his bum. The headmaster raised it slowly then brought it whistling down. It landed with a satisfying thwack right across the cheeks.

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

The study was again filled with the sound of the cane swishing through the air, followed by that awful crack that signalled another searing bout of pain across his already sore bottom. The headmaster drew the cane back for another stroke. Jenkin arched his back and screwed his face up as he experienced the smarting of yet another assault to his now red-raw bottom.

Despite the shocking pain, Jenkin resolved to take the caning bravely and silently; he didn’t want to show himself up in front of his mates. But when slash number three connected with the seat of his trousers he lost all control, his feet beat a frenzied tattoo, as his hips twisted and squirmed. He desperately wanted to jump up and run from the study clutching his buttocks in both hands, but some schoolboy instinct kept him down. He was grateful that he had the chair cushion to grip, even though his hands were now grasping it so tightly his fingernails dug deeply.

The next swipe was greeted with a howl and Jenkin was now audibly muttering: “No!” and “Please!” But there was to be no mercy in the study that afternoon. Mr Lynch stood back, took aim again and the cane flashed through the air with a whoosh and the resulting blow snapped into Jenkin’s waiting backside with venom.

A river of tears cascaded down Jenkin’s face as he waited, heart thumping madly, for the final crack which the headmaster put right across the middle of his buttocks, angled, so that it crossed about three of the other cuts.

It took some time after the last stroke for Jenkin to realise the ordeal was over. “Yes,” the headmaster sighed. “That concludes your punishment, Jenkin. I hope you have learned your lesson.”

Like so many thrashed schoolboys before him, Jenkin remained slumped across the back of the chair, just trying to absorb the line of fire across his bum. Nothing had prepared him for the pain or for the feeling that his bottom had being cut into slices and then set on fire.

“Up lad!” the headmaster commanded, “We haven’t got all day.” With great difficulty, Jenkin’s hands scrabbled for the arm of the chair and he pushed himself upright, panting and sobbing. He danced on the spot, clutching the seat of his trousers. Even through the material he could feel the six vivid and very painful stripes decorating his hindquarters.

“Stand and face the bookcase,” the headmaster intoned. “Wilkinson, take his place.”


Thirty minutes later Owen Davies steered his moped through the gate of a large detached house. Home. The intense pain from his caning had dissolved into a dull ache, but the hard seat of his Honda had set the welts on his bum throbbing. He kicked the stand on his bike and left it standing by the door of the house. The Moped Gang were meeting later.

He opened the front door to find his brother Dai standing, waiting for him in the hallway. A supercilious grin slit the twenty-year-old’s face. “Who’s been a naughty little boy then?” he chirped in the sing-song voice of a child as he swished an imaginary cane through the air. Owen grimaced. This was the last thing he needed.

“I got a phone call from your headmaster,” Dai’s grin broadened. “He wanted to speak to Dad, but I told him he was at that toy train convention until Saturday.”

Owen moved towards the stairs, intent on ignoring his annoying brother. He wanted to get to his bedroom for a close look at his bum.

“So,” Dai blocked his brother’s way, “he told me all about you and your Moped Gang. Six-of-the-best, eh?” He swiped the imaginary cane again. “You naughty, naughty little boy.”

“Piss off,” Owen sneered. He hated his brother. Always had done. Owen was the bright boy in the family. Dai wasn’t clever enough to go to grammar school. He left Gumshoe Lane Secondary Modern aged sixteen. How Owen despised him. Thick as two short planks. A waste of space.

“Of course,” Dai jeered, “When Dad finds out you’ll get another caning.” His arm flew through the air again. “And,” Dai was enjoying himself and he wanted his little brother to know it. “What was it Dad said last time?” He poked the underside of his chin with an index finger, pretending that he was thinking. “Oh yes, I remember.” Owen clenched his fists, for two pins he’d sock his brother on the jaw. He knew what Dad had said.

“He said if you got into any more trouble on that phut-phut he’d confiscate it and sell it. Then where would you be little brother?” Dai reached out and ruffled Owen’s hair. “You’ll be on the bus like the rest of the kids.”

Owen stood devastated. Dai was right. That was what Dad had said. He would do it too. A bare-arsed caning and no moped. That bike was his life. He was the leader of a gang. It made him feel really important. The other guys actually looked up to him. Now what would happen? He knew only too well; no bike, no gang, no life.

“Of course,” Dai spread his arms wide like a market trader offering a bargain to passers-by, “Dad need never know.” He grinned and stared intently at his little brother. Dai had a plan. One that he would really enjoy putting into action. “What’d’ya say little brother?”

Owen sucked in air. What the hell was Dai talking about? Why did he have to behave like an idiot all the time?

“What the fuck are you talking about?” he spat. He hated his brother. Owen couldn’t wait until the autumn when he could leave the house and go away to university. His imbecile brother would probably have to live at home the rest of his life.

Dai shrugged his shoulders and showed Owen the palms of his hands. “A little plan, dear brother,” he said in a mocking accent that made his brother’s skin crawl.

Owen hated himself for doing it, but he asked none-the-less, “What plan?”

“Ha,” Dai spoke in that mocking voice again. “Now, he wants to know. Now, he asks me ‘What is the plan’”?

“Oh, for fuck’s sake, I want to go out,” Owen pushed past his brother and started toward the stairs. Fearful, he might have missed his chance Dai said in a rush, “I won’t tell Dad your headmaster called. I’ll cane you instead.” Owen stopped in his tracks and turned. The surprised expression on his face asked “What?”

Dai took a deep breath, “You’ll get to keep your moped.”

The room span. Owen gripped the banister rail for support. His mouth opened, but before he could tell his brother once more to “fuck off” he shut it tight. He should not be too hasty. That bike was his life. There was only one way for him to keep it. His head spun. This could not be happening. If he let his brother cane him he got to keep the bike.

Thinking about it later, Owen could hardly believe he spoke the next words, “You promise you won’t tell Dad?” Dai’s cold blue eyes blazed, “Scout’s honour,” he said and waved two fingers in the air. “All right,” Owen whispered.

“Good-oh!” Dai smiled broadly. “We must do it now, my shift at the Wimpy starts at five-thirty.” Gingerly Owen rubbed his fingertips across the seat of his trousers. His bum still ached from the headmaster’s caning. Now, he had to let his obnoxious brother beat him on the bare bottom. He would rip it to shreds. He grimaced. You couldn’t make it up, he thought.

Owen watched Dai rush up the stairs and fling open the door to Dad’s bedroom and enter. Moments later he came out crestfallen. “The wardrobe’s locked.” He let the importance of his message hang in the air. Owen needed no explanation. Dad kept his canes in that wardrobe, if they couldn’t get it open there was nothing to beat him with. He would lose his moped after all.

Owen sighed, “Can we get a cane someplace else?”

Dai snapped his fingers to indicate a thought had come to him. “Of course, let’s go round the neighbours and ask if anyone can lend us a cane,” he said sarcastically.

Owen sneered. “All right, but there must be a way round this.”

Dai did the snapping of the fingers thing again. This time he was serious, “It doesn’t have to be a cane. I can spank you.” When Owen looked doubtful, he added, “You know, over the knee, like a little boy.”

Owen blanched. It would have been mortifying enough to go over the dining room table for a caning, but over-the-knee to have his bare bottom spanked; that was too much. Dai read his brother’s mind. He wasn’t about to let this chance to thoroughly humiliate his brother pass. “You’ll get to keep the moped,” he reminded him.

That was enough. It was the only way. With his heart pounding and temples throbbing, Owen nodded his assent.

“Good-oh,” Dai brightened up. “Go wait in the sitting room. I’ll fetch something.” Sorrowfully, Owen trudged across the hallway. Seconds later Dai bounded down the stairs brandishing a heavy wooden clothes brush. He bounced into the sitting room, noting with delight the gloomy expression on his kid brother’s face. He picked up a large armless chair that lay against a wall and plonked it down in the centre of the room. He sat down, spread his legs wide and, waving the brush wildly, called across to Owen. “Come here you naughty little boy.”

Owen grimaced. How he would like to smash his fist into Dai’s smug face. He stood and glared. Dai’s smirk was undisguised. “Come on, let’s get on with this.” He snapped his fingers and pointed to a spot on the carpet close to his right knee. “Stand there.” Owen refused to look at his brother as he shuffled the three paces it needed to take up the position.

Dai sucked in a lungful of air. His eyes sparkled. “Trousers down, little man. Trousers down.” Owen avoided his brother’s gaze and instead concentrated his attention on the far wall. He had never really noticed the painting that hung there before. Some modern art thing. All oranges and reds. It looked like the artist was having a fit when he painted it. Owen stared hard at the picture as he reached for his belt buckle. He was surprised how little his fingers fumbled as they loosened the belt, popped the button at the waistband and pulled the zipper. His pale-grey trousers slid down his thighs unaided and snagged at his knees.

“Ha!” Dai smirked, “White Y-fronts, I forgot your snob school made you wear those. Do they do a pants inspection every morning?” He laughed aloud. Owen sucked on his cheek, determined not to raise to his brother’s bait. “Pants down. All the way,” Dai pointed at Owen’s feet. The eighteen-year-old closed his eyes tight. Think about the moped, he said to himself. If you let him do this you keep the bike. He tucked his thumbs under the elasticated waistband of his pants and guided them south.

Dai tapped the brush against the palm of his left hand. “Bend over my knee, you naughty boy.” I’ll get you for this one day you bastard, Owen told himself as he guided himself across his brother’s lap. Owen was short and squat while Dai was tall and lanky and the boy fitted perfectly. He spread his arms wide and placed his palms flat into the deep-pile carpet. Behind him his toes merely brushed the ground. His bottom was raised against Dai’s right thigh, at a perfect angle for the brush. A cool breeze from the open window behind him caressed his naked legs.

Owen felt his brother pull the tail of his shirt up the small of his back until it bunched at his shoulders. “Woweee!” Dai exploded with glee. Implanted across his brother’s bared buttocks were six distinct welts. “Your headmaster has given you a good set of marks.” He put the index finger of his right hand into his mouth and soaked it in saliva. Then, carefully he traced along each cut with the fingertip. Owen shuddered as the pain in each welt reignited. Dai cupped his hand and roughly rubbed it first across the left buttock and then the right. “It feels like corrugated cardboard back here.” He didn’t try to hide the fun he was having.

Owen shut his eyes. He couldn’t see, but he guessed his brother had a perfect view of his crack and could even see up his hole. He could die from embarrassment. This will soon be over, he reassured himself. Then I can go out on my moped and lead a gang who respect me.

Dai tested the brush in his hand for weight. It was about a foot long with an oval-shaped head three inches wide. It’s primary purpose was to keep clothes clean but it also made a splendid spanking implement. Dai tapped the brush against the centre of Owen’s left buttock so that it fell across three of the cane marks. “This should set them on fire again,” he grinned as he smacked the wood down hard. There was a dull thud as the brush connected with Owen’s firm flesh, followed by an elongated hiss of air escaping through pursed lips; it sounded like a steam train settling down. Owen’s body shook; he raised himself an inch off his brother’s lap and his legs flailed. “No you don’t buster,” Dai gripped Owen around the waist. “You’re not going anywhere.” Satisfied his younger brother was firmly secured he hammered the brush across Owen’s bum. It was like machine gun fire. Rat-a-tat-tat; rat-a-tat-tat. Within seconds every square inch of Owen’s bottom was on fire, from the top of the curves, across the mounds themselves and into the ultra-sensitive underside, the part of the bum that connected with the chair when you sat down.

Even without the cane wounds this would have been a severe spanking. The relatively small area of shiny polished wood attacked his tender buttocks. Owen wriggled and writhed; he waved his arms around; he kicked his legs; his head flailed to left and right and then up and down (just like a horse does when he neighs) as his brother pounded away. The agony in his backside was intense. He gave up and gave in completely, hanging and dangling over his brother’s knees, his squalling taking over, as he gasped, choked, sobbed, and shook. He felt the fiery blistering on his bottom driving him to still deeper wailing and weeping.

This encouraged Dai to renewed vigour. Owen’s legs thrashed about so much he kicked his trousers across the room and the struggle continued so greatly that long before his brother had finished the bare-bottomed spanking the white briefs dangled from his left ankle.

Owen wrestled to escape the relentless torrent of increasing pain that had set his buttocks ablaze. He fought to escape from the very firm grip of his brother’s left arm around his waist. He pleaded, begged, promised and threatened endlessly between his gulps and his gasping for breath. But to no avail.

Dai hadn’t known he possessed such strength: not only was he able to pin his rowdy eighteen-year-old brother in place across his knees, face down, bared bottom high, he continued to batter his buttocks with the brush.  He pounded away at the boy for almost another five minutes, Owen struggled and pleaded but his brother continued; he was having too much fun to stop just yet.

He was so engrossed in his task and Owen so overcome with pain and indignity that neither heard the gentle burr outside in the drive. Four moped riders stared in astonishment through the open window.  They saw that their gang leader had just had his second humiliating beating of the day.

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Charles Hamilton the Second

Fake News #13

z used fake adult schoolboy shorts cane desk (5)


Residents welcome new ‘adult school’

EXCLUSIVE Brocklehurst Bugle

Residents in a leafy suburb of Brocklehurst have welcomed an “adult school” that has just opened in their street.

It is the brainchild of a 65-year-old retired civil servant who calls himself “Mr. Quelch” after the schoolmaster in the famous Billy Bunter stories.

He has built a full-sized classroom on the back of his detached house in The Avenue. It has 15 authentic school desks from the 1950s, an old-fashioned blackboard and easel and a globe that has more than half the countries coloured in pink.

Behind a heavy oak desk is a glass-fronted cabinet. Dangling inside from their crook handles are an assortment of whippy rattan canes.

Mr. Quelch told the Brocklehurst Bugle in an interview the idea was for people over the age of 18 to experience life as a schoolboy in the 1950s. Pupils will be expected to wear a school uniform that includes a red blazer with white trimming, grey short trousers and knee socks.

Mr Quelch said, “We have real lessons in a number of subjects and the pupils are expected to behave themselves properly at all times.”

Those who do not will receive corporal punishment.

“I will pull down a boy’s short trousers and underpants and put him across my knee for a spanking on his bare bottom. I also have a leather taws, a plimsoll and, of course, the dreaded rattan cane. Which of these I use will depend on the degree of a boy’s naughtiness.”

Mr. Quelch has also decked out one of the six bedrooms in his house as a “headmaster’s study”.

He said, “At the end of the day each boy will be summoned to the headmaster’s study where he will have to explain his bad behaviour. I will administer six-of-the-best. This could be on the seat of the short trousers, the underpants or the bare bottom depending the severity of the offences.”

Mr. Quelch said he had already run two school days and there was a waiting list for two more next month. He also “deals with” naughty boys on a one-on-one basis in his headmaster’s study, by appointment.

The new adult school is a hit with neighbours. Mr. Ernie Flynn, aged 52, an accountant, who lives opposite Mr. Quelch told the Bugle, “What a jolly good idea. It sounds like a lot of fun. I can’t wait to sign up for a day.”

Mr. Eric Sloop, aged 45, a shop manager, of The Avenue, told the Bugle he hoped Mr. Quelch would expand his activities and deal with some real life trouble-makers. “I can think of a few louts who hang around Widdicombe Woods drinking and whatnot who would benefit from a stiff trousers-down, bare-bottomed caning,” he ejaculated.

To arrange a visit contact Mr. Quelch on _______________

Picture credit: Unknown

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Charles Hamilton the Second

A ritual played out

z used Three Fishers climbing fence (2)

You walk slowly across the quadrangle, hands defiantly dug deep into trouser pockets. You are taking your time. The summons was for four o’clock. You won’t be late, but you have no desire to arrive early.

A cold breeze bites. The snow has turned to slush beneath your feet. You enter the building. Legend has it that parts of it dates back to the seventeenth century. A narrow stone staircase winds upwards. You concentrate on your feet. The stairs are slippery with the snow. You don’t want to turn your ankle. The House rugby final is on Saturday, you wouldn’t want to miss taking part in that.

You halt when you reach the passageway. You check your blue-and-red hooped cap is straight on your head. You fasten the buttons on your blazer. It is coloured blue and has red braiding around the collar, cuffs and pockets. You sigh inwardly. There’s no other blazer like it. Everyone can recognise a St Tom’s boy. More’s the pity, you think.

Not far to walk now. You know the way. This isn’t the first time you’ve made this journey. You hope it will be the last. You’ve arrived. You pause in front of the heavy oak door. The letters on the notice reading “Headmaster” are fading. It is part of school tradition. The study has been here for centuries. You take a deep breath, count to ten, compose yourself. You rap your knuckles on the door with a confidence you don’t really feel.

“Come!” An imperious voice beyond the door calls. You breathe deeply again and with an unsteady hand turn the large brass handle. The door is heavy and it takes some of your strength to open it. Dr Winstanley, the headmaster, is seated at his desk. He looks up and growls at you. “Hurry up and close the door.” A fire is roaring in the grate, but the room is still deathly cold.

The headmaster waves his arm. He points to a spot on the rug  in front of him. “There boy!” You shuffle forward, stand hands clenched behind your back, head bowed. “Look at me boy!” the headmaster barks. You jerk your head upwards.

Dr Winstanley is an elderly, portly man. His head is nearly entirely bald except for a tuft at each temple. His face is florid and his jowls drop low. Depending on how he holds his head he has three or four chins. You notice his tweed suit is a little battered. A waistcoat stretches across his ample belly.

You see he is not wearing his academic gown and mortar-board cap; the very symbol of the English schoolmaster. They hang on a coat stand in a corner to the left of the headmaster’s desk.

“Baxter,” the headmaster intones. You know he is about to jaw you. You know why you have been summoned to the study. You know what is going to happen. You wish he would just get on with it. He does not. He tells you that you were spotted last evening in the public bar of the Three Fishers Hotel. What do you have to say about that?

You mumble. You accept you have been caught. You don’t tell him that you tried to make your escape undetected by climbing the rickety fence that encloses the pub’s carpark. You don’t tell him that you landed right in front of Harrison, the school captain. You don’t say that you often visit The Three Fishers as do many of the sixth-form. You are eighteen years old and you can legally enter pubs. If St Tom’s were not a boarding school the headmaster would have no right to punish you for being there.

You say none of these things. For you know there is no point doing so. None at all. You have broken the rules. You must accept punishment. You may console yourself that many times in the past you and your pals drank in the pub undetected. You are uncomplaining. You win some; you lose some.

You know that when the headmaster has finished lambasting you it will be your turn to speak. You have prepared a little speech. You accept you are in the wrong. You apologise. That is how it must be. The headmaster has all the power and you have none. You do not tell him it is absurd for the headmaster to beat you. You do not tell him you are an adult and you should be treated as one.

With all speeches over, the headmaster commands you to take off your cap and blazer and hang them on the coat stand. As you do this you see three crook-handled canes in the part of coat stand reserved for walking sticks and umbrellas. They are of slightly different lengths and thicknesses. At different times in your school career you have felt each of them across your stretched backside. Which will it be this time?

You resume your position on the faded rug in front of the headmaster’s desk. You watch as he lifts his considerably bulk from the chair and waddles across to the coat stand. You see clearly he has already made up his mind which of the canes he will use on you. It is the longest and the thickest of the three. It is dark yellow in colour and you can see it has notches every three or four inches along its length. You watch as he flexes it between his hands as if testing the rod for the every first time. Then he swishes it through the air. You can see how very dense, yet whippy, it is. It is an awesome specimen and you know it will be extremely painful.

The headmaster wobbles the cane at you. You don’t have time to reflect on the efficacy of corporal punishment in schools. If you did you would remember your father once told you that public schools such as St Tom’s existed to educate future leaders. Boys had to learn to obey orders and how to give them. They had to be taught the consequences of rule-breaking. A caning was a thoroughly painful way to remind a boy of his duty. The beating was over in moments (although the cuts and bruises might remain for weeks) and everyone was able to get on with their lives.

You watch impassively as the headmaster puts his cane down on his desk and takes hold of a small leather chair. He swivels it so that the back faces into the room. You take a deep draught of air into your lungs. You know he is almost ready. Only one further detail needs to be determined.

“Lower your trousers,” the headmaster barks. You breathe deeply again. It is to be on the underpants. You know this was not unexpected. You are a senior boy and you are not an infrequent visitor to this study; you expected a thrashing and you expected it to be exemplary. You take no comfort in the fact that until recently boys could be beaten on the bared buttocks. That practice stopped after an unfortunate court case involving a school elsewhere in the county.

You resolve to take your medicine with as much dignity as the situation allows. You will obey the headmaster’s every command. You tug at your belt and loosen the buckle. There are five buttons in total keeping your trousers closed. You struggle to get a good grip on the lower two in the fly, but eventually the front of your bags flap open. You wriggle your hips and simultaneously push down with your hands and your trousers slither down your thighs and snag at the knees. You spread your legs slightly and they continue their journey and puddle on your shoes. Your white shirt covers your buttocks at the rear and your cock and bulls at the front so that your white cotton Y-front underpants are hidden from view.

You hear the headmaster intone, “Stand by the back of the chair. Lift up your shirt, bend over.” You shuffle like a penguin to the required place and grip your shirt by both sides. You lift it so that it almost reaches your chin, then you fall forward. The first thing you notice is the musty smell of the chair seat. It is a combination of dust and body odour. The second thing is the heat from the roaring fire. You are close to the open grate and your legs are scorching.

You hear the headmaster taking up position behind you. He is swishing the cane through the air. It makes a terrific sound as it flies. You bury your face in the cushion and clasp your hands together, as if in prayer. You know this is going to hurt. You feel the cane “sawing” against the underside of your buttocks. Then it stops. The headmaster grips the waistband of your underpants and tugs so hard you feel the cotton cloth ride up your crack. You know the cheeks have been separated and there is a canyon between them. The headmaster now has a terrific target.

You feel the cane tapping against your stretched flesh. Any moment now. You know this will hurt greatly, but you have been here before. You know you can take it. You suck in your breath and hold it. The cane is lifted away from your bottom, there is an almighty whoosh! as it scatters air in its path, followed by a resounding crack as it connects with your bottom. It takes a second before the astonishing agony registers. You hack out a dry cough. You know you always do this. Other boys hiss as air rushes from their lungs through half-closed teeth. Others yelp; some yell. You are very proud of your ability to take a beating. That first stroke hurt like crazy. You can feel a thick line has already formed across your bum. It feels like the headmaster has pressed a white-hot wire into your flesh.

You hold your breath once more and wait for the second lash. You correctly predict it will land a little lower than the first. When it does you scrunch your eyes shut and increase pressure on your clasped hands. Now, you have a burning stripe across the lower half of your buttocks. You know the headmaster is an expert with the cane. You rather admire him for it. His aim is impeccable. He can land six strokes in a band no wider than an inch. If he choses no stroke will land on top of another. You know a boy is well advised to keep his bottom perfectly still while the headmaster goes about his duty. If he does not, a stroke might land on top of an existing cut and the resulting agony would be excruciating.

Your bottom throbs and despite your best effort your cheeks quiver and you wriggle your hips. “Steady boy,” the headmaster’s voice seems to come from a very long distance. You dig your elbows into the back of the leather chair and brace yourself. The cane flogs deep into your flesh before bouncing off. You cough louder this time. You feel the pain mounting. It radiates across both buttocks and travels up and down your legs. Your temples pulsate.

Your knees buckle and you make a great effort to straighten them. You hips gyrate and your stomach moves up and down over the apex of the chair. You know the headmaster is waiting for you to steady yourself once more before he lets fly again. You raise your bottom high. It is as if you are saying, “Go on. Do your worst.”

The headmaster lands two strokes. Crack!-crack! The shock of the first made you lift your bum. It put the headmaster off his aim and the second has landed diagonally across three of your welts. You hiss like a steam engine. Your legs march up and down on the floorboards. You shake your head up and down, and to the left and right.

You hear the headmaster’s footsteps. He is pacing the study, waiting for you to absorb the pain. You sense he is no hurry. You are determined not to let yourself down. Your heartrate is off the scale. Sweat soaks the back of your neck. It feels as if your underpants have stuck to your bottom.  You fear your welts are bleeding. You feel like you have sat in the fire grate.

With a monumental effort you grip hold of the seat cushion, spread your legs wide, raise your bottom high over the chair and wait. You feel the cane “sawing” across the underside of the buttocks. The headmaster is finding the “sit-spot”. This is the part of the bottom that connects with the chair when you sit down. You know if he slices you there the pain will reignite each time you sit down for a week.

Whoosh! Crack! Bingo! Right on target. You do the foot stomping and the hip wriggling and the head banging all over again. You hack the dry cough, expel air from your lungs. Blood courses though your body at the speed of sound. Your bum is on fire. Your head feels like it is about to explode.

You hear the headmaster return the cane to the coat stand. “You may stand up boy.”

You heave yourself to your feet. You desperately want to clutch your scolding bottom. You have just enough self-control not to. The headmaster has thrashed you well but you don’t want to give him the satisfaction of knowing this. Gingerly, you pull up your trousers and button up. As you retrieve your cap and blazer, the headmaster opens the punishment book, finds the correct page and enters your details.

You are now fully dressed. The headmaster stands, approaches you and offers his hand. You shake. You are gentlemen. You hobble from the study and with difficulty make your way down the stone stairs. Back in the quadrangle you see it is snowing again. Ruefully, you rub your backside. The throbbing is intense. For one mad moment you consider whipping down your trousers and pants to sit down in the snow. You smile and make your way towards your study.

There is still one part of the ritual to play out. In a moment you will display your wounds to your chums and together you will discuss the headmaster’s prowess. You award him a maximum ten points.

You know that within a few hours the pain will have vanished. The marks will last for many days; some maybe for weeks. Six-of-the-best; such is the lot of the schoolboy. You hold no resentment. You broke the rules and you got caught. You also know that once the dust has settled you will be back at the Three Fishers propping up the bar.


Picture credit: The Magnet

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Charles Hamilton the Second


Room 414

z used otk white pants prefect youngsters sting (2)

Well Winchester, the Head Boy said to me, we can do this one of two ways. Either you can do a detention and miss going to the cup semi-final this evening or you can go across my knee for a jolly good spanking.

My heart raced and my face burned. Had I heard correctly? Taylor the Head Boy and Captain of just about every sport we played at the school was offering to take me over his knee for a spanking.

I was eighteen years old at the time and I couldn’t remember the first time I dreamed of being taken over the knee for a spanking. Mostly I fantasied about my Uncle Roy. He was married to my Mother’s sister and often visited our council flat when his lorry driving took him to our district. He was a massive man, probably six-and-a-half-feet tall. I was a dwarf beside him. He towered more than head and shoulders above me. He was thickly built with powerful arms. I would masturbate at night imagining I was in my bedroom in my pyjamas and suddenly Uncle Roy would burst into the room. I never cared what naughtiness I was supposed to have displayed. I just saw Uncle Roy rip the bedclothes off my body and then gripping me by one wrist he hauled me to my feet before sitting down on the bed and dragging me face down over his lap. I was powerless.

Then Uncle Roy would take hold of the elasticated waistband of my pyjama bottoms and quite slowly tug them down over my buttocks and leave them bunched at the thighs. Now, with my arse suitably bared and in position he would slap me with the palm of his hand. It was as big and as heavy as a shovel and in no time I was bucking across his knee. It was at about this time that in real life I would ejaculate at speed into a wodge of lavatory paper.

I was stunned when Taylor made his offer. Here was someone else who was into spanking. Had I been so naïve to think I was the only one? I blustered with embarrassment, so Taylor put his proposition to me again. He would have known how much I wanted to go to the football match. This was the first time our local team had reached the semi-final of anything. Tickets were as rare as hens’ teeth – and I had one. How could I not go to the match. No, doing a detention was out of the question.

I looked Taylor in the face as in my mind I formulated my response. I didn’t want to sound too eager. He had a bright, open face and although he was the same age as me I don’t believe he had started shaving. The term “baby-faced” fitted him perfectly. He stood stony-eyed, I couldn’t read his mind. Did he know of my inclinations? Was there something about my overall demeanour that gave me away? How had he plucked up the courage to expose his own desires?

Perhaps I should explain that corporal punishment in schools had been made illegal some years before. Mine was not one of those schools from ancient history where prefects had the power to cane or whatnot younger boys. I doubt if any dads spanked their sons at home. Corporal punishment was simply unheard of.

Taylor shuffled his feet impatiently. I couldn’t tell how desperately (or not) he wanted me to choose to go over his knee. We were standing in the corridor not far from the sixth-form common room, I swivelled on my heels to make sure we were perfectly alone and no one could hear us. I sucked in air, run my tongue over my bottom lip and croaked my reply. I’ll go for the spanking.

Taylor seemed unfazed by my answer. I’ll see you after school at three-thirty. In the common room, he said before he sauntered away. I stood rooted. My hear beat so fast I thought I might be sick. Two hours to wait. My first-ever spanking. A bell rang in the distance. Heck, how would I get through double Geography?

Don’t ask me what the lesson was about, I don’t have the slightest idea. I was excellent at geography and ended up with an A-star at A-level but my enthusiasm for the subject paled beside my fervour to be spanked. My how the hands crawled on the clock that afternoon. At last the bell rang; the school day was over. I couldn’t get to the common room fast enough. It was crowded, of course, with boys and girls emptying their lockers. I hung back, waiting eagerly for them to leave.

But where was Taylor? Usually, he was as enthusiastic to get away as the rest of us. Why wasn’t he here. My heart skipped. Had he changed his mind? Had the enormity of what he proposed sank in? Did he regret opening himself up to me in this way? Was he scared we might get caught?

After about ten minutes I was the only one left in the room. I slouched in a chair and flicked through the pages of the Brocklehurst Bugle (could there be a more boring local rag than that?) I was about to give up and leave. I still needed to go home and change before catching the train for the match. Dejected, I packed my books in my locker and made for the door.

Outside a few yards down the corridor was Taylor. Where do you think you’re going? He frowned. I gabbled in reply that I thought he had changed his mind. He grunted, no way. A deal was a deal, he said. He held up a key he was carrying. It was for Room 414, he said. I knew this to be a classroom on the top floor of the building. Nobody would see us there.

He led the way. I truly felt like a naughty boy and kept two paces behind Taylor. This happened twenty-five years ago and I don’t remember what was going through my mind as we took the stairs. The school was deserted, that I can recall. I suppose it must have felt very unreal. We reached the classroom and Taylor unlocked the door. It was a typical classroom of its time. There were tables that seated up to six pupils and at the front was a whiteboard and a desk for the teacher. The walls were covered with brightly-coloured pictures and posters.

I stood uneasily. How was this meant to play out? I didn’t have the slightest idea. I need not have worried, Taylor took control. He fetched one of the straight-backed chairs and put it down in a space close to one wall. Without looking at me, he sat himself down. I hovered close by. In my fantasises I was sometimes beaten by a headmaster. The scenario was that I was a pupil in a posh public school some long time back in history. The headmaster wore a black academic gown and a mortar-board cap. He swished a whippy curve-handled rattan cane.

In those dreams, I would be told to take off my blazer and stand behind a large leather chair. Or sometimes it would be by the headmaster’s desk. On his curt command I would fumble with my belt and undo my trousers. I would let them down to my knees. Then on further instruction I would bend over and offer up my bottom to the cane. In those dreams I always wore white cotton Y-front pants. I wore similar underpants in real life, although they were deeply unfashionable by this time.

Taylor had settled himself and seemed ready to go. He said very little. I was still incapable of reading that beautiful face of his. Taking the initiative, I slipped off my jacket and put it on a table nearby. I stood maybe two feet to Taylor’s left waiting for his instruction. I could see that he had not brought any implement with him. It would be impossible for him to find an whippy cane, of course, but he might have been able to come up with a rubber-soled plimsoll, that other staple of schoolboy punishment from days gone by. At a pinch he might have borrowed a hairbrush from one of the girls, or, who knows?, there was always his belt.

It seemed none of these were to be used. My spanking would be by the palm of his hand alone. Clearly, he did not possess the build or the strength on my Uncle Roy, so I did not expect my punishment to be very painful. He spoke almost for the first time since we entered the classroom. Bend over my knee, he said. Oh, those words. How many times in the years since then has my heart sped at that command? To be instructed to present my backside to a dominant male, to submit to discipline.

I hesitated a moment. How was this done precisely? In my dream Uncle Roy dragged me from bed and manhandled me over his knee. With Taylor, I would have to present myself submissively. It was as if I were saying yes I have been a naughty boy and I deserve to be punished, please Taylor spank my bottom for me. I moved forward closer to his parted legs, then paused. I don’t think I had planned what happened next. It came to me on the spur of the moment. With trembling hands I unbuckled my belt, unbuttoned at the waist and pulled my zipper. The weight of my leather belt sent my pale-grey trousers hurtling to my feet. I leaned forward, stretched out my arms in front of me to break my fall and bent over Taylor’s knee.

We were much the same height and build and I fitted into his body rather well. I placed my palms flat against the floor and with my knees slightly bent the toes of my shoes reached the ground behind me. This way my bottom was positioned over his knee at a good angle for spanking. I couldn’t see Taylor’s expression. He hadn’t expected this turn of events. Me, in my underwear submissively waiting for him to spank me. I am sure his breathing got heavier the moment my trousers hit my feet.

I stared at the parquet flooring. It was scratched and worn and it hadn’t felt the sweep of a broom for some considerable time. Taylor was composing himself. I felt him take hold of the tail of my shirt and push it away from my bum, leaving an area of naked flesh on my lower back. I knew that my underpants fitted me well, but that did not deter Taylor from taking hold of the elasticated waist and pulling so that the cotton was now like a second skin. I felt the pants dig deep into my crack so that each cheek was nicely separated.

Taylor placed the palm of his hand on my left buttock, holding it there for longer than strictly necessary for him to find his aim. He put his other hand in the small of my back to prevent me moving. Then he spanked me. People say the first time is always special. The first kiss, the first sex, the first marriage. So it was with my first spanking. Taylor had some strength in his arm, he was after all one of the school’s most accomplished sportsmen. He spanked me at speed, as my bum absorbed the hurt of one slap another spank immediately followed. It was like machinegun fire.

The pain, such as it was, was not intense; a hand-spanking on an eighteen-yea-old’s bottom covered with cotton underpants could never be severe. But, Taylor warmed up my arse good and proper. My heartbeat was off the scale and my temples throbbed like crazy. On and on he slapped his hand into my tight buttocks. My cock first twitched and then stood at fall attention, like a soldier on guard duty. Taylor must have felt it digging into his thigh and this encouraged him in his efforts. He spanked harder and faster than before.

I feared at any moment I would shoot a load into my underpants. Taylor’s own pale-grey school trousers would be stained. Let him explain that to his mother at home. My breathing was strained: huff-huff-huff. Any time now.

We were both too involved in ourselves to hear the classroom door open. We did catch the strangulated gasp of the school janitor and the clang as the metal bucket fell from his grasp. Taylor released his grip on me and I shot to my feet, the tentpole in the front of my pants pointing at the janitor. He turned on his feet and leaving behind his bucket the janitor rushed down the corridor.

I pulled up my trousers. My head was remarkably clear, it felt as if I were looking down on the room from some height. Taylor remained seated. It was clear to me that his cock was raging as much as mine. The silence in the room was deafening. We could not describe to one another the pleasure we had experienced together. Nor, could we share our fear about what the janitor might say or do.

At last Taylor spoke. He told me to hurry home or I would miss the football match. I left him alone. As I made my way down a deserted corridor, I saw Alderton, a fellow sixth-former, walking toward me. He gave me a cheeky wink but said nothing as he passed. I stood and watched him enter room 414.


Picture credit: Sting Pictures

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More stories from Charles Hamilton II are on the MMSA website


Charles Hamilton the Second