Dreams of spanking

z used bed solo white pants erect cody furguson (1)

Dean lays on his bed staring at the erect cock stretching the front of his cotton underpants. It happens every morning. Regular as clockwork. As day follows night. He dreams of spanking. He has never been spanked. The cane was abolished at school years ago and dads generally don’t take the belt to their sons, no matter how unruly they behave.

He is not concerned why he fantasises about spanking, but he is sad that he is too shy to tell anyone about it. Sometimes he likes to think of bad things he has really done and imagines the punishment he should suffer. Like the other week when he got so drunk at the student union bar and staggered home so out of control he lurched over a garden fence and heaved up two stomach-fulls of vomit into the flowerbed. In his imagination, Dean was bent across the dining room table, jeans and pants at the knees, while the house owner lashed his naked buttocks with a switch he cut especially.

Dean drinks a lot. The other day he rode his moped while drunk. It was a stupid, irresponsible act. Somebody could have been killed. Any magistrate worth his salt would have sentenced him to a birching. Dean sees himself stripped naked from the waist down, tied to a wooden frame. His shirt is bunched up at his shoulders. One prison officer grips a bundle of twenty-four birch twigs bound together with tape. It has been soaking overnight in a metal bucket full of brine. Droplets fall from the birch as he swishes it through the air. You can cut the tension in the room with a knife. A second prison officer holds a clipboard, studies a sheet of paper stuck to it. He licks the end of a stub of pencil. He makes a tick. “Cut number one!” he calls in a clear, steady voice.

The first officer rests the birch against Dean’s buttocks. It is so big and Dean’s bum so relatively small it covers both cheeks. The officer lifts the birch high, swirls it around his head and twists his body before delivering an almighty lash into quivering flesh. Dean screams. The prison officer sweats. He raises the birch again.

After twelve cuts Deans bottom is a mass of cuts and grazes. It looks like raw hamburger meat. Deans screams subside into sobbing gulps as two officers drag him back to his cell.

Dean likes to dream about Paddy, a guy in his English Lit. class at university. Paddy could be the biggest student alive. He is built like a brick outhouse. Dean has this scene where he and other students share a house and Paddy is in a fit of temper. He is trying to finish an essay that should have been handed in yesterday but he can’t concentrate because of the loud music coming from Dean’s “ghetto blaster.” The whole house is shaking. Paddy shouts, “Turn that music down!” He hammers on Dean’s bedroom door. But to no avail.

“Right! That’s it! Don’t say I didn’t warn you!” Paddy bursts through the door and sees Dean flat out on his bed, still in his pyjamas although it’s nearly eleven in the morning. Paddy’s face is purple, Dean’s turns white. Dean is as small as Paddy is huge. It is no match. Paddy grips Dean by the arm, hauls him off the bed. His grip hurts Dean’s arm. But that is only the half of it. Paddy sits on the bed, his weight digs deep into the mattress. Deans struggles. It is a waste of time. Paddy pulls him across his knees. Dean is sucking the eiderdown, his legs dangle in mid-air. His bottom juts at an angle over Paddy’s right knee. Dean wriggles and writhes but Paddy’s supreme strength is too much.

Paddy says nothing. He concentrates on the task ahead. He grips the elasticated waist of the pyjama bottoms and pulls hard, almost tearing the material. Dean’s bum is exposed. He kicks his legs. Paddy adjusts his own body so he can put his right leg across the back of Dean’s calves. He takes Dean’s right arm and twists it up his back. He is pinned down. He is going nowhere. Paddy stretches the fingers of his right hand, cups them slightly and pounds away at Dean’s naked buttocks. Paddy’s forearm is like a leg of mutton, his hand as large and as heavy as a shovel. With only a few smacks Dean’s bum is as red as a London bus. The outline of Paddy’s hand appears in scarlet over and over again across Dean’s bum.

There’s a professor at the university who reminds Dean of the headmaster at his old school. He is about fifty and always sports a hostile look on his face. Dean knows the professor wouldn’t truck any nonsense from his students.  It is late in the afternoon and Dean stands morosely in front of the desk. The study is cold and the night is drawing in. The room is in gloom. The professor holds a sheaf of paper in his hand. He reads with increasing incredulity.

“Balderdash! Poppycock!” he shakes his head. He looks as if he is forced to carry all the woes of the world on his shoulder. He waves the essay in Dean’s face. “You need to spend less time in the bar and more in the library.” His nostrils flare.

“Not good enough. Not good enough,” he mutters as he rises from his chair and walks a few steps to a table. Dean watches with mounting tension as the professor opens a drawer and extracts from it a long, whippy rattan cane. Dean stares at its crook handle. The professor flexes it between his hands. It curves easily. He swishes it through the air. A breeze travels across the room.

“Take off your jacket.” Dean does so.

“Stand by my desk.” Dean takes up position.

“Take down your trousers.” Dean is wearing Levi jeans. He fumbles with the metal buttons but soon they are at his knees. He is wearing his favourite mustard-coloured briefs. They are very snug.

“Bend over.” In his mind’s eye, Dean watches himself lean forward. He lays his stomach on the cold wooden desktop. He reaches forward with his arms and grips the edge of the desk. The professor takes his shirt and tugs it away from the target area. Dean’s buttocks twitch when the professor smooths down his pants so they fit like a second skin.

The professor taps the cane across the underside of Dean’s buttocks. Satisfied that he has his aim, he lets fly. It is to be six-of-the-very best.

There is a guy Dean saw in the student bar. He doesn’t know his name so christens him Michael. Michael has smooth skin and shiny light brown hair. Dean reckons his haircut must have cost a fortune. Michael is a trim lad and his Wrangler jeans hang over his buttocks invitingly. Michael is standing and Dean is behind him admiring his bum. Then, Michael leans forward to look at a picture in a magazine his friend wants him to see. Michael places his hands on his knees and arches his back. His feet are parted. It is the perfect “assume the position”. Dean is so close he could fondle Michael’s backside. Later Dean imagines he is holding an American-style wooden paddle. He rubs it backward and forward. “Brace yourself,” he intones as he lifts it high.

There’s a knock on his bedroom door. “Come on Dean! You’ll be late for breakfast.” It is Roger, a fellow lodger at Mr. Williams’ guesthouse. Dean hears Roger’s footfalls as he races down the stairs. Late for breakfast- again, Dean thinks. That would never do. In his imagination he sees Mr Williams take a thick leather belt from a hook on the kitchen wall. In the real world, Dean slides his hand down the front of his pants.




Picture credit: Cody Ferguson

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Charles Hamilton the Second



Baxter’s Beating

z used cane hold kernled (21)

Baxter stretched his limbs beneath the itchy grey blanket. The clock on the bookcase said eleven-fifteen. He clasped his hands together and put them behind his head. Too late to go to lectures now, he thought. Not that he had intended to.

He surveyed the room. His trousers were strewn over the small leather armchair. His jacket and shirt was on the solid oak table. What a night it had been. He and Marshall had taken in a show and then it was back to his pal’s room for drinks and smokes.

Baxter’s cock still ached. Marshall had been insatiable; gobbling him five times at least. What a mouth, large and round. And he knew how to keep his teeth out of the way. He hadn’t had so much pleasure since the young guardsman at Hyde Park. He had taken out his dentures so had no teeth before he went to work.

Baxter’s cock stiffened, he licked the palm of his right hand and gently massaged the tip of his manhood. He was interrupted by a heavy knock on the door. “Who is it,” he called not bothering to hide the irritation in his voice.

“Manners, Sir,” came a clearly enunciated reply. Baxter groaned. “Yes, what do you want, Manners?” He released his grip on his cock. “I have a message Sir, from the Tutor.” Baxter sighed, “Slip it under the door, there’s a good chap.”

A white rectangular envelope glided under the door. Baxter watched uninterested. I must tip the servant five-bob sometime, he reminded himself before with the sound of Manners’ footsteps fading into the distance on the stone stairway he returned his attention to his throbbing cock.

It was much time later that he remembered the message. It was a printed card with the time and date filled in by hand summoning him to his first meeting with his tutor; the man who would oversee his studies during the three years Baxter would be at the university. Jolly good chap, he thought, he’s inviting me for tea, he had a deserved reputation for providing a good spread.

Baxter admired his reflection in the mirror as he went about his toilet; it was 1926 and all was well in the world. He was at university and his father was paying his bills. He spent most of his time at the theatre or cinema. He wrote revue sketches that he performed wherever and whenever he could. He was a hit a parties. His was perfecting one character in a particular; a middle-aged schoolma’am irritated by a group of young gals (“Don’t do that Clarisa!”). His mother provided the frocks.

A chap only had to attend the first lecturer of term, write his name in the attendance book, and then he need never return. After three years of this there would be examinations, but Baxter did not care; three years was a lifetime.

Baxter was puzzled when he arrived at Mr. Townsend’s study to find he was to be the only visitor. There was no party. Mr. Townsend was  a senior man maybe in his fifties with a younger, vivacious wife – much loved by the students – but Townsend himself was a bit of a cold fish. He had unruly grey hair and a neatly-cut beard. His conventional double-breasted jacket fitted him too tightly. He peered down his angular nose through eyes that were a little too close together.

He was courtesy personified. “Mr. Baxter,” he sighed, at the nineteen-year-old undergraduate standing before him. “Rules permit those residing in College to be out late a maximum of three times a week. You have been late six times this week and a further five last.” He drew in breath and continued, “I have not been informed about your behaviour in the previous weeks.”

Baxter blinked furiously. Manners had ratted on him. Well he could say ta-ta to that five bob.

“Mr. Baxter, you are at the university to learn. You must attend lectures and tutorials.”

“Yes, Sir,” Baxter mumbled. It was like being back at school.

“You were at St. Tom’s were you not?” Mr. Townsend stretched his arms.

“Yes, Sir,” mumbled again for Baxter was unsure if he was expected to answer.

“A very traditional school, I believe?”

“Eh, yes, Sir.” What did his old school have to do with it?

“So you understand the meaning of discipline?”

Baxter was silent. He didn’t like where this one-sided conversation was going.

“I am sure your headmaster would have given you Six for slacking, Mr. Baxter.”

Colour rose up Baxter’s face. “But we’re not at school.”

Mr. Townsend frown and then a slight smile worked the corners of his lips. That’s what they all said, he thought. Aloud he said, “You are not an adult until your attain the age of twenty-one,” it sounded to Baxter that the Tutor was reading from a script. “I stand if you will in loco parentis. You might considered me to be your father, but that might lead to unwanted complications. Instead, you must think of me as your housemaster at school.”

He paused and peered intently at the young man’s puzzled expression struggling to understand the full import of the Tutor’s statement.

The Tutor stood, stretched his arms and walked slowly across the study. It was a small room, dominated by a walnut desk and three small leather armchairs. A bookcase filled a whole wall. He paused in front of it, but not to choose a volume. There was a tall, thin cupboard at one end and Baxter watched uncomfortably as the Tutor took a key from his pocket, inserted it into the lock and opened the door. The undergraduate could only see Mr. Townsend’s back as he reached inside, but the rattling noise he heard was unmistakable. Seconds later the Tutor turned to face the boy; in his hand was a thin, whippy rattan cane.

Mr. Townsend eyed the rod as if seeing it for the first time. Ignoring Baxter’s burning stare he first flexed it between his two hands and then swished it through empty air. Baxter gulped. It was a little shorter and quite a bit thinner than those used at St. Tom’s but he had no doubt it would sting like the blazes.

“But, Sir, can’t we talk about this?” Baxter blustered.

Mr. Townsend’s lips pursed. They all said that as well. “There is nothing to say Mr. Baxter, unless you want to be sent down for the rest of the term. What would your father think about that?”

Baxter squirmed. He knew darn well what Dad would think. There’d be no more university; he’d have to work for his living. He said none of this to the Tutor, instead he shrugged his shoulders in defeat.

Mr. Townsend busied himself turning one of the low armchairs so that its back now faced into the room. Baxter hopped from one foot to the other. There was no turning back. He would be brave. This was not the first time he had been caned.

“Please lower your bags and bend over the back of the chair.”

Baxter blanched. That was a first; a trousers-down caning. “B… b…” he started a protest but stopped himself immediately. What was the point? The tutor was in charge, Baxter had broken the rule about late nights and a few others that the Tutor did not seem to know about.

“Come on please Mr. Baxter,” the Tutor tapped his cane on the back of the hard leather chair, the noise ricocheted around the room.  “I have others to deal with this evening.”

Baxter took a deep breath. His belt unfastened easily and his loose-fitting trousers slipped over his hips. It took the slightest tug to have them at his shoes. Penguin-like he shuffled two steps closer to the chair, looked over his shoulder to give his master an imploring look, found the Tutor determined, and slid himself over the chair.

He looked down at the seat cushion inches in front of his face. It was patterned in greens and blues. Summer colours. He concentrated carefully. He needed to focus on something. Such as the large, round, greasy, indentation. Hundreds, possibly thousands, of posteriors had contributed to the dent. It was an old chair. It had seen much action. He gripped the cushion edge tightly. Waiting.

His heavy trousers were at a puddle at his feet. His grubby off-white underpants were riding up into his buttock crack. He couldn’t have felt more self-conscious. Embarrassed. Humiliated, even. A cool gust of wind brushed his naked legs. The study window was slightly ajar. He felt Mr. Townsend’s strong hand grip the tail of his shirt and roughly bundle it up his back. He did the same with the singlet. Now, there was nothing between Baxter’s cotton-covered backside and the Tutor’s cane.

He could feel it pressing into his flesh. Mr. Townsend was finding his spot. Preparing himself. It would be any moment now. Baxter waited, heart racing, teeth clenched, eyes tightly shut, while Mr. Townsend, a powerful upright man and as strong as an ox adjusted his academic gown so he could get a better swing. Then Baxter imagined, the Tutor flexing the cane.

He did not have to imagine his shudder of anticipation as the Tutor laid the cane across the centre of his buttocks and pressed it hard into the meat. He was getting his aim. The boy felt the cane move off his bum; then there was an almighty swish and it came crashing down, hitting his buttocks and sinking deep into the flesh.

“Hisssssssss.” It wasn’t a yell, it was almost silent. The sound of air being expelled. The boy tightened his grip on the seat cushion.

Swipe number two was equally as hard and landed almost exactly on top of the first. The pain shot from the centre of his bum and sped up and down his legs. He wriggled his hips and waggled his buttocks.

Two down. The pain was excruciating; so much more than Baxter had expected. The cane was smaller and thinner than at St. Tom’s but somehow it had more whip and sting than those at school. Mr. Townsend was an expert caner. He was able to inflict maximum pain with seemingly minimal effort

The third stroke interrupted his thoughts. It landed lower, across the crease. Each swipe had been laid on with vigour. The Tutor was giving it some beef; he could have been beating a carpet. Baxter bit down into his bottom lip, stifling his desire to yell. It felt as though there were three throbbing ridges beneath his underpants.

Baxter was astonished by the severity and intensity of the strokes. He felt flushed and humiliated. Cold perspiration ran down his shoulders. After number four hit home his legs were marching up and down on the carpet. Tears flooded his eyes.

Number five hit low. His knuckles whitened as he gripped the chair. His feet stamped up and down but the smooth soles of his shoes could not grip the cheap carpet beneath them and his legs slid from behind him. He banged his head up and down on the chair. His temples throbbed almost as much as his backside as blood rushed through his entire body and tried to exit through his ears.

Mr. Townsend adjusted his position. Baxter’s body tensed. He knew what was coming. The Tutor laid the cane diagonally across both buttocks from the lower part of the left cheek to the top of the right. Slash! Baxter’s bum had a perfect imprint of a five-bar gate. His backside vibrated vigorously and he let out a piercing howl. For a moment he released his grip on the chair and started to stand, he wanted to dance a jig – anything to deaden the agony. He regained composure and resumed his hold on the chair tightly.

“Enough. It’s over. You may stand.” Mr. Townsend continued to talk as Baxter dressed. “I hope we do not have to repeat this Mr. Baxter, but if we do, please be aware that next time I shall double the tariff and reduce the protection of clothing.”

Baxter fastened himself up. The throbbing in his corrugated bum was intense. He might be bleeding. He nodded vigorously at the Tutor but said nothing. “Time for you to leave,” the Tutor smiled, extending his hand. They shook like gentlemen. Baxter hobbled to the door, turned the handle and opened it. He was not surprised to see Marshall standing outside, ashen faced.

Picture Credit: Kernled

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Charles Hamilton the Second


Looking back . . .

z used cane touch toes pyjamas (15)b

Sometimes these days I rub my eyes with disbelief with much the same vigour I used to rub my backside. That’s when I remember my days at St. Tom’s. In the housemaster’s study (again). In pyjamas, touching toes for six-of-the-best .

You tell kids that today and they think you’re mad. Eighteen years old and bending over for the cane. It happened all the time back in the nineteen-sixties. St. Tom’s was a middling public school (that is a private fee-paying school) with delusions that it was among the elite. It dripped “tradition”: traditional curriculum, traditional games, traditional religion and, of course, traditional discipline.

St. Tom’s was an enclosed boarding school; boys only of course. There were rules for everything: do this; don’t do that. Break the rules, touch your toes. There was a small town close to the school and it was an illegal excursion to the cinema there that got me my last caning.

Do you remember Sophia Loren? She was the Italian sex-kitten film starlet of her time. There was a film and I can’t for the life of me remember the name of it now, where she stripped off her clothes. Not all the way of course, but for we sex-starved boys of St. Tom’s a flash of thigh would have been enough to fuel self-abuse for weeks.

Naturally, we had to see it. So taking our lives (or at least our bums) in our hands three of us snuck off one Saturday. We got spotted by a master coming out the cinema. Had he been inside watching the film himself? If so he was a jolly rotter for turning us in. The cinema was out of bounds at all times, not just when steamy sex movies were showing.

Our housemaster Mr. Camden had a ritual. Looking back after fifty years it seems a pretty rum one to me. He would keep a list of boys who misbehaved during the and call them to his study at lights-out, just before bedtime. That way he ensured we arrived in our pyjamas. Naturally, a whippy rattan cane would sting much more without heavy trousers and cotton underpants as protection.

So, that night, Richard MacDonald, Brian LeFevre and myself took ourselves down to the study. Camden was a strange cove. He looked to us like he was a hundred years old at least, but he stayed on at the school for another twenty-odd years after I escaped so he must have only been in his forties. He was a stout man with a ruddy complexion (was he a drinker?) and was incapable of talking in a normal voice. He always sounded like he was addressing a parade ground full of troops.

I think it was Richard who knocked on the door. We waited for the customary order to “enter” and shuffled to stand in front of Camden’s desk. It was a ramshackle affair, not too big and always covered in piles of exercise books. He must have spent half his waking hours marking. I remember the room was cold although it was early summer. Parts of the school supposedly dated back three or four hundred years so it was a draughty hole.

We stood hands behind backs, eyes downcast at our slippered feet, in the classic naughty-boy pose. We knew how to play our role in the drama that was about to unfold. We also knew how it would end.

I had been caned countless times (who hadn’t?) it was that kind of school. It always hurt; that was after all the point of the exercise and I never really got used to it. I think the embarrassment of bending over and offering my backside to a master much larger than me was as bad as the pain. I wasn’t like some of my pals (Richard was one) who took it entirely in their stride. Some actually welcomed the cane. It was some kind of badge of honour. I know when we were lower down the school we would make marks with ink on our snake belts, one for each time we were caned. Some years later I met an old school pal who had formed a club where men dressed in school uniform and relived their canings.

Camden jawed us a bit. Did we know the cinema was out of bounds? Yes, we did. That was it really. We coughed to the crime and all that was left was the punishment.

Camden had a tall thin cupboard in one corner of the room. I have never seen these cupboards anywhere but in a school study. What possible use could they have except to house an array of punishment canes? He had several of different lengths, thicknesses and densities. His pride and joy was a Malacca which was no longer or thicker than the plain rattans but it had a powerful density. It was as springy and whippy as the others but with ridges every four inches or so along its length it would leave a boy’s backside heavily bruised. If a master chose to put an extra bit of beef into a swipe he could easily cut flesh.

The Malacca was for recidivists, those for whom a “normal” caning had proved ineffectual. It was also reserved for senior boys like ourselves, Camden supposing that we were too tough even for the thickest rattan or dragon. We watched impassively, but with pulses racing, while Camden fished a key from his trouser pocket, unlocked the cupboard and reached inside. The rattling of several canes seemed to echo around the room. He turned to face us holding the Malacca between two hands.

Another of Camden’s rituals was to flex and swish the cane through the air. He was testing its effectiveness as if he had never encountered it before. He was also trying to intimidate the boy standing before him, demonstrating just how much damage the rod could do to a boy’s stretched buttocks. I wasn’t intimidated and I doubt if my two fellows were either; we just wanted to get it over with.

Camden soon obliged. “Stand there,” he waved towards a wall dominated by bookshelves. We did as instructed. “Hands on head” (another ritual) “Face the bookcase.” The only uncertainty was how he would cane us. Sometimes it was the traditional “touch your toes”; otherwise we would drape ourselves over a piece of furniture. The desk was always too cluttered to be used but on occasion I had presented my bum over the back of an armchair or by gripping the seat of a hard straight-backed chair.

“Stand out LeFevre,” Camden hollered. I supposed the chaps back in the dormitory would have heard. Not that it would matter. It was no secret that we had been summoned to the study and every boy at the school knew that could mean only one thing.

Brian turned on his heels and with hands still on his head, he lumbered into the centre of the study. Richard and I turned to watch. There was nothing so fascinating as watching a fellow get a bowing. Brian’s face was pale. It was difficult to control such things, the body makes natural reactions in times of stress. Camden flexed his cane and then pointed to a spot in the middle of the carpet, “Bend over. Touch your toes.”

Brian sucked down a lung-full of air and slumped forward. He was a thin, wiry boy and when he bent over his pyjama bottoms rode up across his buttocks. Camden swished his cane and gently sawed it across the centre of Brian’s bum. Suddenly he stopped. “What’s this?” he shouted. “Padding?”

I exchanged glances with Richard. Padding? A chap never put padding down the back of his trousers. It was cheating. Not the done thing. A bad show. Besides it was bloody impractical if a boy was only in pyjamas. “You are wearing underpants, LeFevre. Stand up boy.”

Underpants. Hardly “padding”. But to Camden they were both the same. Brian straightened up, his pale face now quite red. “Take down your pyjama bottoms.” It was a straightforward command. I noticed Brian’s eyes watered. He chewed on his bottom lip. I thought for a moment he would protest, perhaps he wanted to but thought better of it. There would be no point. Camden was in charge and we all knew that well.

Brian’s fingers trembled as he stumbled with the drawstring of his pyjamas. He had trouble undoing the knot but eventually succeeded. He let go and the bottoms hurtled to his feet, rather like clown’s trousers do. He started to bend forward once more. “Not so fast,” Camden barked. “Since you have attempted to deceive me. Let us have the underpants down as well.”

I saw Richard’s eyes blaze. Bare arsed. That was unheard of. And it was so jolly unfair. Brian hadn’t tried to use padding. Most of the chaps wore underpants under their pyjama bottoms. Matron might not think it very hygienic but it was immensely practical: it stopped our erect cocks from poking through the fly of the pyjamas. And believe me when we were eighteen it was impossible to stop our dicks saluting at the least provocation.

If looks could kill. Brian shot Camden a dirty scowl, but still he did not complain. I watched him hitch his thumbs into the waistband  of the pants and slowly guide them over his buttocks until he released them at the thighs and let them slither to his ankles at their own speed. I tried not to gape. There were lots of times at the school when we saw one another naked, but we went around pretending not to notice. It was impossible now not to see Brian’s long, thin cock. It was awesome, quite the largest I had seen in my life until them.

Feigning nonchalance Brian bent down once more. I had a side-on view so was unable to see his crack or hole but, of course, this would have been in Camden’s view. How utterly humiliating it must have been for Brian. The housemaster took his aim, raised the cane to above shoulder height and with a slight turn of his body swiped it across Brian’s buttocks. The boy gasped and his body shook under the impact, his balls bounced up and down. Almost immediately a deep pink line emerged across the pale flesh where the cane had landed.

Number two fell a little lower than the first and the next a little higher. Camden was an expert caner. The Malacca landed precisely where he intended. It helped that Brian was also an expert canee (if indeed that is the correct word). He took his lashes as stoically as circumstances allowed and did not move around unduly.

After three strokes Brian had a band of hurt roughly two inches wide across the centre of both buttocks. Camden slashed another three into that patch. Six welts throbbed across Brian’s bum. It had been an exemplary thrashing. Brian opened and closed his mouth silently. The agony would have been intense, but he managed to utter not one sound. On command he rose, pulled up his pants and pyjamas and resumed his position by the bookcase. His eyes were damp but he wasn’t blubbing. A chap never blubbed during a caning, he would never hear the end of it from his pals.

Camden called my name. I walked forward and when instructed I bent over. It is more difficult to touch your toes than perhaps people imagine. It puts a tremendous strain on the calf muscles. I grabbed my ankles instead and with my knees bent slightly my bottom jutted out at a decent angle to receive the caning. I felt Camden take hold of my pyjama jacket and move it an inch or so up my back and away from the target area. I shuddered; not from fear (as I said I had been in this position before) but from a cold draught that came from I know not where. I had a close up view of the pale blue carpet beneath my feet. It was new, a modern concession. Not so long previously the floor had been bare boards with a tatty rug.

I closed my eyes and shut my teeth as I felt the cane tap against my stretched pyjamas. The housemaster was finding his aim. I knew it would hurt. A great deal. That was the point of it. No point in caning a boy’s backside unless it hurt. I understood that. I heard the cane swish through the air and the crack as it connected with my hard bum. It seemed like ages before I felt the burning pain. Air escaped through my clenched teeth.

As with Brian’s caning, the second landed. Whop! Just below the first slice. My buttocks were blazing. Camden was such an expert with the cane. His beatings were awesome. I tried to ignore the pain searing from my arse up and down my legs. From somewhere outside the study I heard the sound of footsteps on creaking boards. Then they stopped. Some one was outside the door. Probably, another boy waiting his turn.

Number three connected with the top of my thigh. I must have yelped, it would be impossible not to. Camden had missed his aim, maybe he wasn’t such an expert after all. I stopped myself leaping to my feet and rubbing away.

“Keep still boy.”

I was soaked with sweat. My temples throbbed every bit as much as my bum. My blood pressure was off the scale. The housemaster paused, allowing me to settle. He took better aim this time. The fourth went high, on the top of the curves, well away from the thighs. My bum felt like it was on fire. Camden was putting all his beef into this, he had beaten carpets with less force.

Bang-Bang! The final two cut deep into my meaty bum, in quick succession. I had no time to absorb the first until the second landed, almost on the same spot. It was over. I stared down at the carpet, already the intense pain was dissolving. I knew that soon it would become an awesome throb before turning to a scorching glow. I waited for permission to stand. I had no time to reflect on the incongruity of an eighteen-year-old allowing himself to be thrashed in such a way by a schoolmaster. In those days one didn’t legally become an adult until twenty-one, maybe we were still conditioned to think of ourselves as children.

I rose and resumed my place at the bookcase. MacDonald offered Camden his arse and a couple of minutes later we were on our way back to the dorm. to display our wounds to an admiring crowd.

Picture credit: Sting Pictures

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Approved School Santas

used drawing santa claus squad cane

Mr. Jossop, the headmaster of Lansbury Approved School for young offenders, peered through his rimless glasses. Mr. Kochinhand, his senior housemaster, was a kindly man, but this was a hare-brained scheme. It was fraught with danger. It was sure to be a disaster.

“The Rotary Club are one-hundred-percent behind it, headmaster,” Kochinhand beamed.

They would be, Jossop grimaced.

“What could possibly go wrong, headmaster?” Kochinhand was not to be deterred.

Jossop’s eyebrows shot heavenwards. Everything, he thought. Everything.

The Rotary had organised it all, Kochinhand had explained. Young children all over town would get a visit from Santa Claus. The orphanage, the children’s hospital, the many charities that gave meals to the children of destitute families.

“And they want our lads to be the Santas,” Kochinhand could not stop beaming. “It’s an excellent idea, don’t you think, headmaster? It would give our boys a chance to show responsibility,” Kochinhand wrung his hands together. “What could possibly go wrong?” he asked again.

Lansbury was a school for young criminals. Four hundred boys, up to the age of nineteen, crammed the dormitories and classrooms. Thieves, robbers, repeat offenders. They shouldn’t be let loose on poor defenceless children, Jessop thought.

What could possibly go wrong? They could abscond. That’s what. It was by far the biggest headache approved schools faced. They weren’t prisons; they were just boarding schools. Slightly more secure than the most expensive fee-paying schools in the land, but boarding schools nonetheless.

Absconding. That was why the boys were forced to wear ridiculous uniforms. Brown short trousers and beige knee socks. Up to the age of nineteen. Any boy on the run from approved school would be immediately spotted by the public. Especially in the depths of winter.

They always came back. Then, they would be up before Jessop. Bent across his desk, resting on their elbows (his preferred position), while he lashed his stout but whippy cane across the seat of their short trousers. Eight strokes for the sixteens and overs. Six of the best for the rest.

“So, headmaster,” Kochinhand was not letting this go, “Do you approve?”

No, Jessop was sure, he decidedly did not approve. If he had his way, the boys would be locked in their rooms over the so-called “festive season.” They were nothing but trouble. Keep them there until New Year had come and gone.

But, life was never so simple. Many important people, those with influence, belonged to Rotary. They would not take kindly if he and his school turned down their offer.

“Go ahead, Mr. Kochinhand,” he sighed. “But, you take responsibility for it mind.”

Beaming from ear-to-ear, Kochinhand left the headmaster’s office. Jessop leaned back in his chair and groaned.

Despite his cheery demeanour, Kochinhand was not confident the boys would sign up for Santa. Never volunteer, was the mantra of the approved-school inmate. Why should they help the bosses?

“It’s for charity,” he told the surly senior boys. “Helping poor children.” He hoped that would strike a chord, for every one of the lads he cajoled was from a deprived family. His reward was silence and indifference. In despair, he slouched off to his study.

He was close to astonished when an hour later Tomkinson, a nineteen-year-old house breaker, knocked confidently on his door. He had six names. All ready to be Santa. “Just give us the sacks and point us in the right direction!” he grinned.

Kochinhand was overjoyed. Jessop suspicious. Why had they volunteered? It could only be they intended to run away. Who wouldn’t prefer to spend Christmas at home than at Lansbury? “I don’t trust them an inch,” he growled. “They’re up to something.”

Jessop had a plan. Next day dressed in his own Santa suit he lined up six Father Christmases. Despite their youth and general thinness, they quite looked the part. Even sour Jessop had to admit that. Jessop paced the ground before them. Tucked under his arm ready to slip into his hand at a moment’s notice was a stout cane. He was rarely seen throughout the school without an ashplant.

He had the air of a sergeant-major as he strode up and down. “Surveillance!” He said the word three times. For emphasis. “You will all be under surveillance. Do not for one moment think of absconding!” The false whiskers covering each boy’s face hid their smirks remarkably well.

Jessop growled his suspicion. There wasn’t a backside in front of him that he hadn’t thrashed in the past few months. Why would the lads want to help the school?

“We’ll be watching you. Like hawks.”

“Ho-ho-ho!” they chanted in unison as they shuffled off to waiting cars, heavy sacks on their shoulders.



Terry O’Kane, nearly nineteen, habitual shoplifter and house breaker and Santa for the afternoon, stood impatiently. No amount of cheap coloured paper decorations could brighten the dour mission hall.  He knew that green and grey paint. They were the only colours destitute people ever saw.

About thirty ragged children, not a decent meal inside any of them for weeks, sat listless in front of a geezer performing conjuring tricks. By their sides, already abandoned to indifference, were wooden fire engines for the boys and rag dolls for the girls.

O’Kane had performed his duty well. Now, he waited for his chance. There was one more thing to do before he could return to his sleigh and fly off into the night. He inched toward a table, furtively. Watching all the time for movement from the children or their Guardian-appointed overseers. There was no time to lose. There never was in these situations.

O’Kane loved the thrill of it. In a split second he could be away. Job done. Home and dry. Elated. Or, his collar could be felt. A figure of authority gripping him hard. Dragging him to the police station. The Magistrates Court. Approved School. He had seen it all before.

They all watched the conjurer. He was quite good, O’Kane had to admit; although he hated himself for thinking it. The Guardians had moved outside, into the frost, to be away from the stinking children. To smoke a cigarette in peace.

It was now or never. O’Kane slowly backed towards the table. He had already cased the joint. He knew what he wanted. All the usual Christmas fare was there. Turkey. Brussel Sprouts (the kids would love them, O’Kane sneered silently). Cake.

And, in the centre of the groaning trestle table; a plum duff. A Christmas pudding. Satisfied, he was not overseen, the teenager expertly scooped it up with one hand and into his Santa sack. He was through the door to freedom in seconds.

Three streets away at the Baptist Church Hall, Sandy Cockburn (pronounced Co-burn) had given away his presents. Baptists were not renowned for their jollity. These children had clearly leaned the trait young. Cockburn did not much care. He had never liked Christmas. Grownups got drunk, fought with one another and beat their kids. No, as far as Sandy Cockburn cared you could stuff Christmas along with your turkey.

But, he reckoned, this Christmas might be good fun. If the plan worked. It was dangerous; but not reckless. The lads at Lansbury might have the best holiday yet. Some old dame was organising games. The nineteen-year-old scrutinised the room. It was some kind of treasure hunt. They were following clues. Trying to find something. The key was in the Bible.

Cockburn stamped his feet on the ground. The afternoon was getting late, the air chilled quickly. He was glad of the Santa suit; his legs would be turning blue if he was wearing the short trousers of his approved school uniform.

Even so, he wrapped his arms around his body, hugging himself for warmth. How much longer would he have to wait? Suddenly, a movement from outside. A car drew up. Cockburn groaned. Jessop, the headmaster, had returned to take him away.

There was no time to lose. It was now or never. He couldn’t disappoint the other lads. They would never let him forget it. He scoured the room. Nobody was looking at him. The Bible was too interesting. Overexcited, overweight children yelled with glee. They had found the clue.

Cockburn shrugged his incomprehension. Two plates of jam tarts disappeared into his sack.

“Hello, Mr. Jessop,” he said cheerfully, as the headmaster lumbered through the door. “Look how excited they are.” He hoped his tormentor couldn’t hear his thumping heart. “I’m so glad you let me be Santa, Sir.”

Jessop growled. “Go wait in the car.”

“Oh yes, Sir,” Cockburn grinned and made his escape.




“Whatever possessed you to think you would get away with this,” the headmaster was at his most pompous. Even, for Jessop. Kochinhand, the senior housemaster, had made himself scarce. He couldn’t face his boss’s smugness.

Before him, bared-kneed, hands behind backs, eyes downcast slightly, stood six approved school lads. They had eaten the Christmas feast of a lifetime. Pies, cakes, pudding; the works. Fine food that tasted much better for being illicit. Stolen. From under the nose of the hated Jessop and his “schoolmaster” wardens.

Jessop rose from his chair and strode purposefully across his study. He stopped at the far end, near a row of cupboards. All present knew what was contained inside. He stopped, sniffed the air a little, and returned more sedately to his desk.

“I could send you all to the Magistrates Court,” he leaned into them, eyes blazing. The boys shuffled uneasily. They didn’t need it spelt out. Repeat offenders. Already approved-school boys. The consequences were dire. The birch. Bared buttocks. No question about it.

Jessop straightened. For two pennies, he would have them carted away. Let some bulky prison officer flog the skin off their backsides. But, he couldn’t. The full story would be told. Jessop, had sanctioned the Santa trip. He had personally supervised it. It would get into the newspapers. The national ones, not just the local rag. It would cost him his job.

Oh, he vowed, silently, he would make Kochinhand pay for this.

“But,” Jessop continued. He tried a warm smile. He wasn’t very good at it. He lacked practice. “This is the season of goodwill,” his stare burnt a hole in O’Kane’s forehead. “So, I shall be lenient.”

The teenager relaxed.

“But, not that lenient,” he scowled. “There shall be no magistrate. We shall deal with this here.”

Cockburn stiffened. This was expected. Jessop was fearsome with the cane. Cockburn had been beaten often – who at the school hadn’t? – but he could never quite get used to it. Other lads appeared to shrug it off. Six, eight strokes were as nothing. Cockburn always suffered. The pain of a beating. The resentment of having to bend over in ridiculous short trousers and offer up his arse to the bullying headmaster to whip. He hated it all.

Jessop retraced his steps across the study. This time, he paused at the far end, delved into his pocket, found a key and inserted it into the lock of a tall thin cupboard. Six lads, pulses racing, feigned indifference, at the rattle of punishment canes. They heard, but could not see, Jessop select one from his vast collection and then swish it. It made a terrific swoosh! as it cut through air.

There was a pause and another rattle. The headmaster was not quite satisfied. Somewhere tucked away at the back of the closet was the rod he wanted. “Ah!” he sighed loudly. Found it. He held it between his hands, flexing it almost lovingly. What a beauty. A Malacca cane, a little over three feet in length. Yellow-brown in colour. Straight, not crook-handled like traditional school canes. Quite thin but dense, with notches along it every four inches or so.

Oh, he wished fervently, if only he were permitted to flog them trousers and pants down. The Malacca was designed to take a bare arse off. Blood would ooze and welts would rise. They would stay for a week or more. A constant reminder to the louts before him of just who was in charge. Who was boss. He was. And, they were the scum of the earth. How dare they steal from the poor. How dare they humiliate him so.

Satisfied with his choice, Jessop pushed the door closed. “Face me,” he barked. There was no need for further words. “You know the drill.”

Indeed, they did. As one man, they shuffled across the study carpet and faced the wall. Unbidden, they placed their hands on their heads, waiting submissively. They heard the almighty swish of Malacca cane hurtling through empty air. Once. Twice. Then, three times.

“Right, O’Kane. You first.”

Pale-faced, the eighteen-year-old slowly turned to face his punisher. The headmaster had a lined face. He would say he had earned those lines. A lifetime fighting with young offenders would do that to you. His expression was mean, but so was his character. When had he stopped beating his boys to help them improve their behaviour and grow to fine adults? Now, he did it for vengeance. Revenge that these boys and countless more before him had destroyed his life. There was no helping the likes of them.

“Bend over the desk.”

O’Kane breathed deeply. He stepped forward and leaned headfirst. Soon his forearms were flat on the desktop. His back was arched and his legs spread. His tight shorts rode up into his crack. His buttocks were meaty, but firm. They stretched tightly. Jessop could see the outline of the teenager’s underpants.

There was nothing to be said, only a deed to perform. Jessop took up position a little to O’Kane’s left, placed the Malacca across the underside of the boy’s bum, and bent his own knees. Then, the cane rose towards the high ceiling of the study. Jessop twisted his body as the rod fell and sliced at full force into O’Kane’s arse.

The boy eyes shut tightly. His teeth bit deep into his lip. His head shook like a neighing horse. It hurt. The pain was incredible. Had Jessop seared him with a red-hot poker?

The second and third cuts swiped into the beefiest area of his rear. Again, O’Kane did the eyes shutting and the lip biting. His bum wriggled from left to right. He hated himself for showing it hurt, but he was not in control. This was a reflex action; his body was protesting against the agony being inflicted on it.

Outside the study door, Kochinhand, the senior housemaster, paced the passageway. How he needed to smoke a cigarette. His nerves were shattered. The message from his colleague Mr. Taser had been curt, brusque even. “Attend, the headmaster’s study. Immediately.”

He had heard of the boys’ trickery. The day would not end well for Kochinhand. The distinct sound of cane thwacking against stretched backside confirmed this. He waited, throat dry. Why couldn’t he get his hands to stop shaking?

He had not been told, but he knew Jessop’s mind. Kochinhand must wait until all six lads had been dealt with. Only once they had been punished and sent on their way, could Kochinhand enter the lion’s den and suffer his own painful fate.


Picture credit: The Hotspur


More stories from Charles Hamilton II are on the MMSA website


Charles Hamilton the Second



z used drawing snowballs Mag (2)


Dr Henderson-Smith the headmaster was at his most self-important. Five hundred schoolboys sat in rapt attention.

The headmaster, dressed in a rather old-fashioned academic gown, berated his boys. He was a commanding figure, tall, grim, stiff as a ram-rod. His grey moustache bristled and his knitted brows frowned.

The headmaster had centre stage and the old ham actor was enjoying his moment. The topic of his sermon was snowballs; and the throwing thereof. The dangers of eyes poked out by shards of ice. Damp clothes and influenza.

He wrapped his academic gown around his body giving the appearance of a crow about to take flight. “I do not have to spell out the consequences to any boy found throwing snow.”

Undeniably he did not. St Francis Independent Grammar was a traditional school. It had traditional classes, traditional sports, traditional uniform and traditional discipline. An errant boy could expect a very sore backside indeed.

It was proving to be one of the worst winters on record. Brocklehurst had been carpeted with snow for most of December. It had stopped snowing for a while, but forecasters predicted more to come. It might even be a white Christmas.

That evening George Baker, sixth-form pupil and prefect at St Francis, stared from his bedroom window. The snow was falling once more. He tucked a hot water bottle beneath his sheets and dived under the blankets. Shivering in bed, he went through a plan in his head. He had been thinking about it for months. Maybe, he thought, one day, he would put the plan into operation.

The next day Dr Henderson-Smith sat in his study. The school day was completed. The open fire roared, but there was still a chill in the air. He busied himself preparing a composition to inflict on his Upper VI Latin class. His concentration was disturbed by a dull thudding noise. He paused from his labours, uncertain what it was that he had heard.

Then, there it was again. Thud. Something had connected with the outside of the study window.

“What the Dickens?” the headmaster said aloud, even though he was alone in the room. When a third thud followed, he was certain he had solved the mystery.

A handful of snow was slithering down the outside of the window.

He rushed over and peered through the now-misty glass.

“What the …?” This time he failed to complete the sentence. Below his study window, in his clear view was a boy throwing snow. Dr Henderson-Smith watched dumbfounded as the boy crouched down, scooped snow into his hand, fashioned it into a ball, and then threw it, seemingly at random at passing pupils.

The boy was clearing disobeying the headmaster’s instruction. No snowballs. Dr Henderson-Smith stared with radioactive eyes. Then he threw open the window and roared, “Baker, my study. This instance!”

The boy dropped the snow he was fashioning for another missile and turned to face the noise.

“Yes, Sir,” he said meekly and moved to enter the building.

The headmaster closed the window and sat at his desk, dumbfounded. He had caught George Baker throwing snowballs in clear violation of the headmaster’s expressed instructions.

George Baker? Sixth-former and prefect. The boy was in the headmaster’s Latin class. He was among the brightest boys in the school and was destined to go up to one of the country’s top universities.

There was a timid knock on the heavy oak door of the study. Baker had arrived.

“Enter!” Dr Henderson-Smith bellowed. Slowly, the door inched open and a head appeared. It was a small head topped with short curly black hair. The face was flushed; possibly caused by freezing cold air; or possibly because its owner, one George Baker, knew he was in serious trouble. Very serious trouble indeed.

“Don’t dawdle boy!” Dr Henderson-Smith was incapable of speaking at a normal volume. “Close the door, you are letting the warmth escape.”

Baker edged his way into the room, closed the door behind him and halted, unsure what to do next.

He eyed the headmaster resplendent in his academic gown, seated behind a huge oak desk. The boy had never been in this room before. There had been no reason for him to visit. Particularly not for the purpose that had brought him today. Baker found the dense oak panelling intimidating. The room was gloomy even during bright sunny days, but now, in the bleak mid-winter, it felt like the inside of a cave.

“Stand there boy!” the headmaster pointed very deliberately to a point on a worn rug in front of his desk. Generations of schoolboys had shuffled their feet on this spot. It was the first phase of a ritual played out over possibly hundreds of years at St Francis. This was where every sorrowful boy stopped and stood, head bowed, to await his fate.

The second phase was the “jawing.” The headmaster berated the woeful boy for his misbehaviours. Dr Henderson-Smith had perfected his own style: pomposity. He aimed his steely eyes at Baker like a weapon.

“Were you not in att-end-ance at morn-ing ass-emb-er-ley yes-ter-day morn-er-ing?” the headmaster strung out every syllable for dramatic effect. This way, he believed, he struck terror into his boys.

Baker listened confused. When Dr Henderson-Smith spoke this way it could be difficult to follow what he was saying.

“Well, Baker?”

The eighteen-year-old sixth-former took a stab at a reply.

“Yes, Sir.” It was not a detailed response, but the boy hoped it would do in the circumstances.

“Pah!” It was an explosion. Air rushed through the headmaster’s lips. His snowy white moustache bristled; his eyebrows knotted. The outrage he felt was intense.

“And, yet!” Dr Henderson-Smith was barely in control. “And yet, you saw fit to disobey my clear instructions on the throwing of snowballs!”  The headmaster was speaking more clearly now, but Baker was unsure if this was a rhetorical question. Was he supposed to answer?

He chose silence. He stared down at his feet and let his headmaster continue his denunciation.

“Never in my whole life as a headmaster,” he lied, “have I ever come across such wilful disobedience as this Baker. Never.”

Dr Henderson-Smith slapped the palm of his right hand on the desktop, startling young Baker who was intently studying the pattern on the rug.

“What do you have to say for yourself boy?”

Baker’s heart pounded. What could he say? He wished the headmaster would just get on with it.

“Well!” the headmaster screeched. He genuinely could not understand what Baker had been thinking.

“Sorry, Sir.” It was all he could think to say. He certainly couldn’t tell the truth.

“Pah!” It was another explosion of indignation. Sorry, the headmaster thought to himself. You soon will be.

“You leave me no choice, Baker.”

The boy raised his head. His grey-blue eyes shone as he watched the headmaster heave himself from his chair and pace the study. His destination was a corner cupboard. It was unlocked and within seconds the headmaster was rummaging round inside. His body blocked the teenager’s view, but he could hear a distinct rattling within.

Seconds later, Dr Henderson-Smith withdrew a curve-handled cane. Baker had seen many of these in the past; St Francis was that kind of school. But he had never before been on the receiving end of one. The headmaster looked attentively at the cane in his hands; as if seeing it for the first time. He murmured to himself and thoughtfully he flexed it between both hands. It was a little over three feet long and no thicker than a pencil.

Baker gawked from a distance. As school canes went it did not look especially vicious, he thought. He had seen longer and thicker ones. But, what this caning novice did not know was that in expert hands even a short thin cane could be made to deliver an excruciating sting. Dr Henderson-Smith was such an expert.

The headmaster turned to face the boy. He swished the cane through the air. If the swoosh! that it made was intended to intimidate the sixth-former it worked. For the first time that afternoon Baker wondered if disobedience had been such a good idea.

“Take you blazer off and hang it on the hook on the door.”

Baker wanted to comply with the order, but his fingers didn’t want to work. Was it the cold or his nerves, he wasn’t quite sure.

Eventually, the jacket was in place.

The headmaster swished the cane once more. “Stand in front of my desk.”

Baker had never been caned in his life, but he had heard enough tales from school friends to know that in a moment he would be bent across the desk, with his bum in the air to allow the headmaster to thwack six-of-the-best across the seat of his trousers. It would hurt like blazes. He expected that. That was after all the point of it all.

“Lower your trousers.”

Baker had not expected that and the pleading look in his eyes betrayed his feeling. He stood rooted.

“Lower your trousers boy!” the headmaster repeated, a little louder this time.

Still Baker could not move.

“If you do not submit yourself to corporal punishment, I shall contact your father and tell him you are suspended from school. Do you wish me to do that?” The headmaster spoke slowly and deliberately.

He hoped it would not come to that. What on Earth would Mr Baker make of the situation? His eighteen-year-old son in the headmaster’s study refusing to take a beating. His son who had never given a moment’s trouble before. He had never needed caning before; never been given detention; never been set lines. He had probably never been admonished for bad behaviour in his life.

“One last time Baker. Lower your trousers.”

Sweat from the boy’s palms transferred to the belt as with shaking hands he struggled to loosen it. He could feel blood racing through his body at great speed as he pulled the buttons of his trousers loose, exposing the white Y-front underpants beneath.

The mid-grey trousers slipped down to his knees. He waited for the next instruction. Dr Henderson-Smith had developed a cruel streak in his years as a headmaster. The youngster standing in front of him was terrified. Dear God, the boy would be thinking, please don’t make me take down my underpants. The headmaster waited a moment and then waited some more.

“Lift your pullover and shirt clear of your bottom and bend over the desk.” He tapped the cane gently across the hard oak desktop in case there was any doubt.

Even though blood coursed through his body, it drained from Baker’s face, making him look ghoulish.

The boy adjusted his clothing exposing a flat hairless stomach and stretched his arms out ahead of him, gripping the desk top with both hands and thrusting his bottom out.

“Not like that,” the headmaster was easily irritated when a boy did not present himself properly for a caning. “Right over. Flat on your stomach.”

Baker eased forward. It was a huge desk and it was a stretch for him to reach the far edge with his hands. Unsure what to do with his arms, he folded them and tried to bury his head.

“Put your hands on your head and keep them there,” the headmaster barked. “Do not move them and at no point try to protect yourself with your hands.”

Baker did as instructed. Hands on head worked. It was a surprisingly comfortable stance to take. Comfortable for now, but what happened next would be far from that.

Thinking about it later, Baker tried to imagine the scene. He was stretched across a huge oak desk; his trousers now at his ankles, revealing long, slim, slightly hairy legs. His shirt and pullover was pushed up and his midriff was bare. It was a cold room but he could feel the heat from the roaring open fire against his naked flesh. His white cotton underpants fitted snugly once the headmaster had tugged them tight against his buttocks.

His face was pressed down into the old oak desk. There was a faint aroma that he couldn’t identify; probably some kind of polish.

He waited, heart racing, teeth clenched, eyes tightly shut, while Mr Henderson Smith a powerful upright man and as strong as an ox adjusted his academic gown so he could get a better swing. Then Baker imagined, the headmaster preparing himself, flexing the cane.

He did not have to imagine his shudder of anticipation as the headmaster laid the cane across the centre of his buttocks and pressed it hard into the meat. He was getting his aim. The boy felt the cane move off his bum; then there was an almighty swish and it came crashing down, hitting his buttocks and sinking deep into the flesh.

Baker’s mouth opened and closed. “Hisssssssss.” It wasn’t a yell, it was almost silent. The sound of air being exhaled. The boy tightened his grip on his entwined fingers and pressed down on the top of his head.

Swipe number two was equally as hard and landed almost exactly on top of the first. That got Baker yelping. The pain shot from the centre of his bum and sped up and down his legs. He wriggled his hips and waggled his buttocks.

Two down. The pain was excruciating; so much more than Baker had expected. How could anyone take six strokes like this? Then, he panicked. Six? It was to be six wasn’t it? The headmaster hadn’t announced a tariff. Would it be more? Please God, no.

The third stroke interrupted his thoughts. It landed lower, across the crease. Each swipe had been laid on with vigour. Dr Henderson-Smith was giving it some beef. Each stroke had been an almighty swipe; he could have been beating a carpet. This one had the boy’s feet marching up and down on the spot. His bum felt swollen. He desperately wanted to jump up and rub away.

“Oh, no!” Baker thought it but did not say it aloud. Dr Henderson-Smith had taken hold of the elasticated waist of his underpants. “Please, no, don’t pull them down.”

He bit down into his bottom lip, stifling his desire to beg for mercy. But, he need not worry. The headmaster pulled the waistband of the Y-fronts away from the boy’s back to get a full view of his bare buttocks. He was inspecting the damage done so far.

What he saw were three deep red marks, across both cheeks, almost parallel to one another. A thick welt had formed where two of the strokes had landed nearly in the same place. If he struck that area again, it would surely bleed, he thought.

The headmaster was not a sadist. He believed in corporal punishment; not in torture. A caning should be well laid on, especially if the body on the receiving end was a senior boy, or a recidivist, a repeat offender. Intense pain should be inflicted and there should be marks that would stay for days, a reminder of the penalty for bad behaviour.

Dr Henderson-Smith did not wish to leave Baker’s buttocks bloodied, so for number four he took aim lower down, away from the danger area. It struck at the sensitive “sit spot,” where the cheeks met the thighs. That one had Baker hollering. Tears flowed. He head-butted the desk; he marched his feet up and down and twisted his hips and bottom; but none of it helped. The agony was intense and it was not going away any time soon.

Four strokes had been delivered in a carefully timed sequence. Sufficient time was allowed to elapse so the full force of a stroke could be felt before the next was sent crashing home. The final two were delivered in quick succession, and at intense speed. Whack-whack. The whippy rattan bounced off the tight cotton-covered buttocks. It sounded like two pistol shots echoing around the ancient study.

George Baker thought he might faint. His scorched bottom felt like the headmaster had forced him to sit in the open fire. When the headmaster delivered the final cut to the boy he rested the cane on the desktop and waited for the final throaty scream to recede. For what seemed an age neither the headmaster nor the thrashed boy spoke or moved.

The only noise in the room was the continued quiet sobbing of George Baker, still bent across the desk.

Dr Henderson-Smith brushed his hand across the boy’s shoulder. “You may get up now,” he said softly.

Unsteadily, Baker lifted himself off the desk. His backside felt twice its normal size. He rubbed gently and even through the cotton underpants he could feel at least two distinct deep weals. The surface of his bum felt hard, like leather.

Tears still trickled from his eyes, but he was in control of himself now. Gingerly, he pulled up his trousers and tucked in his shirt. He could not bear to look at the headmaster. He wanted to get out of the study without delay.

While Baker struggled into his blazer, Dr Henderson-Smith reached into the drawer of his desk, extracted the punishment book and entered the details.

“Sign,” he pushed the book and a ball-point pen across the desk. The headmaster wanted this to end swiftly too.

“You are dismissed.”

Dr Henderson-Smith stood at the study window perplexed and watched Baker walk through the quadrangle and out of the school gates.

Twenty minutes later at home in his cold bedroom George Baker inspected the damage. The pain had gone, but his bottom was tender to touch. It might be a bit uncomfortable sitting on a hard dining room chair at tea time.

So, he thought, that’s what it felt like to get the cane. It would have been a pity to have gone through his whole school career at St FIGS without knowing. He picked up the Football Monthly, eased himself down on the bed and flicked through its pages.

Picture Credit: The Magnet


This story comes from a free-to-download collection of stories about St. Francis Independent Grammar School (St. FIGS). For more details click here.

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More stories from Charles Hamilton II are on the MMSA website


Charles Hamilton the Second


The School Dance

z used school cane pants chair (19)

Jay Collins’ cock pulsated against his snug cotton underpants. Just the thought of the girls he would meet that night gave him a terrific hard-on. He stared at the tentpole in his pants. It was no good he would have to polish one off.

Quietly, he edged a straight-backed wooden chair towards his bedroom door. Then tipping it on its hind legs he wedged the top under the door handle. That would stop his mum coming in unexpectedly.

He lay on his bed and dragged the white Y-fronts over his throbbing muscle. Jay Collins, eighteen years old and a virgin. He had no control over his prick. He only had to be within ten yards of a girl and it saluted. He spat into the palm of his right hand and worked it up his rigid shaft. He closed his eyes and imagined himself rubbing his face between the breasts of a sixth-form schoolgirl.

It was the annual Christmas dance. The boys from St. Septimus against the girls of St. Winnie’s. His cock would never hold out.

Dr. Fortescue, the new headmaster of St. Septimus Independent Grammar School, had been clear. He was not a man who enjoyed life and he did not see why others should either. His rules for the dance were simple. No alcohol. No cigarettes. No jiving. Full school uniform. He did not say, “No petting between boys and girls.” He assumed that was already taken as read. “I shall be on hand to ensure there is no misbehaviour,” he growled at the boys. They all knew what that meant.

Jay had been at an all-boys’ school since he was eleven years old. He had hardly ever met a girl. Certainly, he had never been alone with one. Not even the sister of a friend. Now, tonight, he desperately hoped, he would be able to get close to one. Maybe, even to touch.

A stream of cum shot over his belly.

. . .

Audrey and Susan were rather mellow; courtesy of the miniature bottles of whisky they had smuggled into the dance in the pockets of their blazers. The school hall was full now. Somebody had taken great care with the decorations. “It actually feels like Christmas,” Susan shouted in her friend’s ear.

Audrey grinned, almost demonically. “Yes, and it’s time to hand out the presents.” Both eighteen year olds giggled conspiratorially.

They might be sixth-formers of St. Winnie’s, a somewhat demur school for girls, but they were worldly-wise. Like so many young women they found boys of their age own immature. Audrey and Susan preferred the undergraduates at the local university, and the students liked them very much indeed. There was something about a girl’s school gymslip and navy blue knickers that sent the boys wild. Audrey and Susan had long since ceased to be “maidens.”

Susan shrieked theatrically as yet another St. SIGS boy held a sprig of mistletoe above her head and demanded a kiss. She obliged and pursed her lips against a spotty cheek. Blushing profusely, the teenager ran away.

“He’s going back to his mother,” Audrey said, satisfied with her own superiority.

“We need to get moving. We’ll run out of time,” Susan cautioned her friend. She nodded an agreement.

The girls had a plan. It was fiendishly simple. It would work easily. They knew so; they loved it that they had so much power.

“Cock virgins. They’re all cock virgins,” Susan had told her friend earlier. “We can have anyone we choose.”

“Let’s find the most desperate two we can and give them the time of their life,” Audrey swung her long auburn hair around her face.

“That shouldn’t be hard,” Susan giggled. The word “hard” had set her off. She knew the allure her breasts had on young males.

Susan chose her victim quickly. A nerdy prefect. “He’s not bad looking either,” she told Audrey. “But, the look of desperation in his eyes …” she turned her own eyes heavenwards.

Audrey couldn’t make up her mind. There were so many to choose from. She rather supposed it would be a fair-haired lad who had danced ineptly with her. “It was obvious he had a hard on,” she reported, then howled, “Actually, he was hung like a donkey.”

“Well, what are we waiting for?” Susan led her friend back to the boys.

Jay Collins thought he was dreaming. A girl was asking him to go into one of the darkened classrooms with her. His cock thrust through the fly of his pants as she led him by the arm into the passageway. Audrey suppressed a sneer, he was like a dog slavering over a raw steak.

Dr. Fortescue, the headmaster, had abandoned his study. It was too far from the school hall; he would never be able to supervise the dance from there. He wrapped himself in his overcoat and set up a listening post in the geography classroom. Oh, why, he castigated himself, had he allowed this infernal dance to go ahead. He could be in his nice warm house, drooling over a favourite magazine.

The classroom was freezing. He slipped his hand inside his coat and withdrew a bottle of Teachers whisky. “Just for the cold,” he told himself unconvincingly. Furtively, he switched off the light.

The cold and the alcohol befuddled Fortescue. He couldn’t get the image of Peter Rodriquez out of his mind. The eighteen-year-old had troubled him since the first time he saw the olive-skinned beauty in the bar of the George Hotel. The boy’s jet black, almost blue, wavy hair was cut short exposing a longish slim neck. His mid-grey school trousers clung to the outline of his legs which went all the way up to tight muscular buttocks.

The headmaster had thrashed the teenager in front of the whole sixth-form on his unprotected naked buttocks. It was to the first of many beatings. Fortescue was known throughout the school as “The Tyrant Headmaster” and he had earned the title. No excuse was too small to have Rodriquez bent over a chair or the large desk in the headmaster’s study. Earlier that day Fortescue had lashed six stingers with his special dense Malacca cane into the boy’s stretched buttocks. The pale-grey trousers fitted like a second skin; the outline of the boy’s Y-front underpants clearly visible. That would teach him not to throw snowballs.

Fortescue took another sip at the bottle. The stirring in his pants was troublesome. He couldn’t ignore it any longer. Stealthily, even though no one else was there to see, he slipped his hand under his overcoat. The tip of his cock was raw. He gasped in cold air.

Suddenly, the door flew open and the light came on. Four teenagers, two girls and two boys, stood in the doorway. It took a second or two for the full horror to sink in.

“Wha …?” Dr. Fortescue blustered hurriedly removing his hand.

“Oh lor!” Keith Green gasped.

All four backtracked, jostling one another in their urgency to leave.

“Wait. Stop where you are!” The headmaster roared. He was a commanding figure. He expected to be obeyed.

“You girl, what do you have there?”

Too late. Audrey had tried to slip the miniature bottles of whisky back into her blazer pocket. She blushed. Confused. The whisky had already gone to her head.

Dr. Fortescue rose from his seat. Standing, he made a tall, grim man. He looked as strong as an ox. The truth of this was soon to be demonstrated.

“All of you. Go to my study. Now. This instance. I shall follow you later.”

Without question, the four shuffled down the passageway. Their fate inevitable. Even for Susan and Audrey and they weren’t pupils at St. SIGS.

The headmaster’s study was set in the clock tower. The doleful teenagers had to slip and slide across the school quadrangle. The cold was intense, but none felt it. They had other concerns.

They manoeuvred the narrow stone steps leading to the study in silence and paused outside the heavy oak door. Without thinking, Green and Collins faced the wall and placed their hands on their heads. Audrey and Susan glanced at each other. They were familiar with these rituals. Things were much the same at St. Winnie’s. They joined their companions in submission. No one spoke. Each was left to contemplate what would happen next.

Minutes later, they heard footsteps. Two people. Voices. Dr. Fortescue had fetched Mrs. Witherington, the senior mistress at St. Winnie’s.

“Ah,” she cried, “I should have known. Henley and Stritch.” Mrs. Witherington, married for twenty years, but still a spinster, gurned her face like a gargoyle.

Dr. Fortescue lead the way into the study. “Wait here until you are called,” he growled over his shoulder as he closed the door. The room was still warm. Embers glowed in the large open fireplace. Satisfied that his manhood was no longer raging, the headmaster removed his overcoat and made about stoking the fire.

Mrs. Witherington admired the study. The huge desk, topped with green leather was magnificent. So was the mullioned window that overlooked the school grounds with its ivy-covered walls.

The study was panelled in oak. The fire dominated one wall and two others had shelves and cabinets, including a tall thin cupboard with a smoked-glass front. A Chesterfield couch and two padded armchairs made up most of the furniture, but there were also two straight-backed chairs leaning against one wall. She rather wished her own study at St. Winnie’s was so splendid.

Fortescue straightened himself from the fire, turned and faced his companion. “Corp-oreal punishment,” he ran the words over his tongue. It was a statement, not a question. They should be beaten, he had decided. His boys would be caned, but he would defer to the senior mistress on the girls.

“Most definitely, headmaster. Most definitely.” The headmaster was taken aback by Mrs. Witherington’s eagerness. She blushed when she noticed his quizzical stare.

Fortescue strode across the study to the tall thin cabinet. He found a key in his trouser pocket and rather like a magician pulling a rabbit from a hat, he opened it with a flourish, suddenly realising how absurdly proud he was of his array of punishment instruments. He stood back offering his companion a view of its contents.

The doctor only used the cane himself; it was the only instrument that a headmaster should use. A thrashing by the Beak had to be awesome, something to be feared by the boys. But, his predecessor was a man of diverse tastes. That was why the cabinet also stored a leather taws, a white rubber-soled gym shoe and a wooden paddle.

The senior mistress’s eyes widened. A wooden paddle. She had never seen such a thing before. She reached in and picked it up, caressing it lovingly. “From America, I suppose,” she whispered softly.

It was a weighty piece of hardwood. It looked like a smaller version of a bread board she had at home. It was probably four inches by nine and had a firm handle attached. It had been lovingly created. All the edges had been sanded smooth and it been painted with several coats of varnish. Six small holes had been drilled into it. She could see it was a little worn, it had seen action in its time.

“Perfect,” she wheezed, as if to herself. “This will do the job.” She held the handle tightly and swished the wood through the air, taking its weight.

“Let’s get them in here,” Dr. Fortescue was taking control.

Four teenagers shuffled into the study. Eyes downcast, they stood hands clasped behind their backs in front of the headmaster’s enormous desk.

Jay Collins raised his eyes from the floor to look at the headmaster. The elderly man was stone-faced; his icy-blue eyes burned into the boy.

Dr. Fortescue was a man of few words, but this time he jawed and he jawed. He addressed the two abject boys. Letting the school down. Girls. Alcohol. He leaned back in his chair, so they could not smell the whisky on his own breath.

Susan and Audrey stared impassively at the worn rug beneath their feet. At least, the headmaster had not discovered the cigarettes. Nor, the condoms.

The lecture over, Dr. Fortescue pronounced sentence. Green and Collins drew in breath. The cane. Six. The boys’ hearts raced. “But,” the headmaster continued, “Mrs. Witherington will attend to the girls.”

The relief was etched on the boys’ faces. The cane. They had expected that. But, no mention of trousers down. Maybe, the Beak was in a festive mood. Goodwill and all that. The last time Keith had been in the study – with two other prefects for defying the Beak’s orders –  it had been six swipes; on the bare. He cut their arses to ribbons. Keith could not sit in comfort for days. It was weeks before the marks cleared completely.

The senior mistress took her cue. “Henley. You first.” She eyed the leather-topped desk she so admired. She nodded to it. “If I may headmaster?” His eyes gave assent. “Bend over that desk.”

Audrey was impassive. She was no stranger to corporal punishment. She stepped forward to the desk’s edge, estimated its size and where she should put her arms and leaned forward.

“Aren’t you forgetting something?” Witherington barked. “Lift up your skirt. This is to be on the knickers.”

Keith Green’s heart thumped. Instinctively, he glanced at his classmate. Collins face was puce. Sweat was soaking his scalp, even though the study was rather cold. Both boys stared intently as, her own face now scarlet, Audrey hauled herself to her feet. She shot a pleading look at her senior mistress. If it was mercy she sought, her luck was out. All she saw was Witherington holding the paddle in her right hand and stroking it gently with her left.

Audrey had never seen such a weapon before. She had been spanked many time at school and at home with a slipper or a leather strap. They could sting like billyo, but this wooden board was in a different league. Her stomach twisted in knots and she resolved herself to be brave. She couldn’t let herself down in front of the boys. She grinned at them impudently to show she wasn’t afraid.

“Quickly, now,” the senior mistress patience was sorely tested.

Audrey hitched her skirt, uncovering her navy-blue knickers. She caught sight of Jay and remembered how hard he had been during the dance. Hung like a donkey, she had said. She leaned forward, rested her elbows on the desktop, gritted her teeth and waited.

Witherington lined up the paddle with the cheeks, patting them gently in warning, then drew back. Whack! Suddenly there was an explosion and Audrey felt pressure against her backside pushing her forward. The paddle bounced off the firm bottom as if it was made of rubber. It was raw pain. The stinging was intense. It was nothing like the slipper or the strap. Her whole bum was alight.

Audrey jumped away from the desk, clutching her knicker-covered rear and danced furiously. Her face was bright red, her eyes bloodshot and watery.

“Stay in position,” the senior mistress growled. Contrite, Audrey lent over the desk once more.

“Green,” Dr. Fortescue had his own work to do. “Over to the chair boy.” He waved a curve-handled rattan cane. Green was startled. He was so fascinated by the girl’s arse; he had quite forgotten his own plight.

Swish! The cane flew again. “Take down your trousers,” the good doctor grinned. “Well as the ladies are being punished on their underwear, so must you,” he said in answer to a question etched on the sixth-former’s face.

Hands trembling, Green released the catch of his belt, conscious of Susan’s eyes burning into him. His trousers slowly slithered down his thighs. His bum was round and firm. He was outgrowing his underpants and they clung tightly to his buttocks and crotch. Unintentionally, Susan licked her top lip as she watched the eighteen-year-old lean forward over the chair, submitting his backside to the lash of the cane.

Jay had no interest in his pal’s predicament. He could not pull away from Mrs. Witherington. She raised the hefty wooden paddle to her shoulder height and slammed it forward. It landed with crushing force against the knicker-covered bottom.

“Ooooh! Ouch!” Audrey roared, half-rising up from the desk.

“Stay in position,” Mrs. Witherington slammed the wood into Audrey’s backside again.

Across the study, the headmaster “sawed” his cane across the top most part of Green’s round bottom. The boy’s body tensed, expecting an explosion of agony. It was not long in coming. Dr. Fortescue spun his body, rather like a golfer, and landed a stinger. He was rewarded by a clear line across the top of the sparkling white underpants. He knew a red raw welt would be instantly forming across the teenager’s taut flesh. Air rushed through Green’s clenched teeth. His knees buckled and his bum rose an inch or two over the back of the armchair. He steadied himself and waited for slash number two, conscious of the paddle raising and falling and the yelps of Audrey from across the study.

The paddle smacked again and again. Audrey soon lost count. Her buttocks quivered and throbbed. Spasms of pain ran across the blistered flesh. By the time the twelfth and final whap! had crashed into her, Audrey’s eyes were wet. Her bum was incredibly sore. She hastily wiped the tears off her face, hoping her friends had not seen. When instructed, she stood, smoothed her skirt down and stood against the wall, allowing her friend Susan to take her place.

Susan was taller than Audrey. Jay, who was no expert on these things, thought her posterior was a little fleshier than her friend’s. It could probably absorb the awesome wood much better. He watched her take hold of the hem of her skirt, raise it high, exposing bottom and long, slim legs and lean forward offering herself to her tormentor.

The headmaster had completed his Six. Keith rose unsteadily and hopped from foot to foot. Even with his pants up, it had been a terrific whacking. He wanted to massage away at the pain, but didn’t want the Beak to know he was hurt.

Audrey, looked on transfixed. She rather wished he had giving himself a rub. She wouldn’t mind feeling that arse for herself.

“Collins, you next.” Dr. Fortescue tucked the cane under his arm and glared at the boy. Jay’s face paled. He could not move. “But, Sir …” he blubbered. His hands wrung in front of him, his shoulders hunched. He couldn’t face the Beak. “Please …. I can’t, Sir. Please, no. Don’t make me.”

The headmaster slipped the cane into is hand and swished it menacingly. “Pah! Come on lad. We haven’t got all night,” he growled. He walked forward, intent on gripping the teenager and hauling him to the chair. Jay Collins swerved to avoid the clutch and ran to the door.

“Stop him! Stop him!” Fortescue roared at an astonished Green. Too late. The door swung open and Jay had made his escape.

“Come back. This instance!” Never in his entire life as a schoolmaster had such a thing happened. Of course, boys were sometimes reluctant to bend over and take their punishment like men. If need be the headmaster would have a senior boy pinion an offender across a desk or chair. But like the Canadian Mounties, Dr. Fortescue always got his man.

Not this time. At least, not yet. Collins was now slipping and sliding across the school quadrangle towards the school gates and his home. A large hot sticky patch of goo spreading through the front of his trousers.

Picture credit: Sting Pictures


AUTHOR’S NOTE: This is one in a series of stories called The Tyrant Headmaster. To read episode one, click here


More stories from Charles Hamilton II are on the MMSA website


Charles Hamilton the Second


After the party

The parent-teacher association Christmas party was in full swing in the school hall. Wine was being glugged and cheese snacks nibbled. Adam and Steve, senior prefects and bastions of St Simon’s Independent Grammar School, their hosting duties nearly at an end, hurried away from the festivities.

“Quick, in here,” Adam opened a classroom door and ushered his pal into the darkened room. He removed a torch from the pocket of his fancy green and red school blazer and directed its beam into the far corner. “Look what I’ve got.” He leaned forward and picked up a wine bottle. “Goldener Oktober, Liebfraumilch,” he beamed. “Classy stuff. There’s another bottle there,” he nodded into the shadows. “They’ll never miss a couple.”

He pulled out his Swiss Army knife, cut the metal fastening on the bottle and dug out the cork. Then he raised the bottle to his lips and drank heartily before handing it to Steve. The wine was warm, even though the room was not. Steve shivered as the alcohol hit his stomach. Within seconds the bottle was half empty.

The two eighteen year olds perched their buttocks on the edge of a desk, their thighs touching. Their eyes met. Steve tilted his head. Opened his mouth a little. Leant towards Adam’s welcoming lips. Tongues entwined. Fingers ran through hair. The taste of wine intermingled with tobacco from cigarettes smoked earlier.

Adam pulled away. Couldn’t breathe. Needed air. Lungs once again full, he plunged forward. Cocks ached. Steve tugged at Adam’s belt buckle. Undid it. “No, not here,” Adam pushed his pal’s hands away. Not too vigorously. “Someone might come.”

“C’mon, there all at the party. It won’t finish for half hour at least.”

“Okay.” Adam had no willpower. He loved it when Steve tossed him off. Flies were soon undone and trouser fronts opened wide. Aching dicks strained against white cotton Y-fronts.

“Here, let me.” Steve tugged at the elastic waistband pulling the pants over his pal’s smooth buttocks and liberating the erect penis. Steve’s drowned his tongue with spit, leant forward, made a perfect “O” with his lips and took the swelling member in his mouth.

Mr Doughty, the housemaster of Queen’s, needed to pee. He had drunk too much wine and it was going straight through him. The boys’ bogs were close at hand. He would go there. He lurched down the passageway. It was too dark. He reached for the walls to guide him on his way. What was that noise? It sounded like a screeching cat.

He saw a faint light through the window of a classroom and went to investigate. He peered into the gloom and saw two sixth formers; one lying back across a desk, the other leaning into him with the boy’s cock in his mouth.

Doughty’s bladder was about to burst. He rushed on to the lavatories. He knew the boys. He taught one of them. White. What a delightful boy. His cobalt blue eyes could light up a classroom. His crooked smile melted the heart. Often Doughty dreamed of running his fingers through the teenager’s unruly fair hair.

The housemaster rested his head against cold wall tiles as he directed piss into the urinal, his cock stiffening in his hand.

Moments later he was back at the classroom. He shoved open the door and switched on the lights. “What the … ?” Two terrified pupils, trousers and underpants at their knees, gaped.

“I have never in my life … Words fail me …” the housemaster stared at Steve White’s steel-hard cock. Then, quickly averted his gaze.

“We have guests. Parents. School governors …” Doughty’s brain could not communicate with his mouth. His stomach churned. “My study. Tomorrow morning. Both of you.” He closed the door and unsteadily returned to the party, leaving behind two bewildered schoolboys.

The next day dawned brightly and sunbeams hit Steve in the face as he lay in bed. He had barely slept. His life was about to end. He and Adam had talked about it. Expulsion from school was the least of their worries. Would Doughty tell the police? Steve was too scared to go to prison. Everyone would know. His friends would desert him. God! What would his father say? Or do? Steve might be homeless before the day ended.

Doughty had a bad night too. His wife assumed he was drunk, as he often was. The schoolmaster’s mind was filled with the hugeness of Steve’s throbbing cock. When Doughty reached for it the teenager thrust his hips forward. The hot throbbing prick felt like a velvet covered steel rod in his hand; and, when Doughty started stroking it, Steve inhaled deeply, moaning softly.

Doughty’s own dick stood rock hard and his wife took full advantage.

Hours later, Adam and Steve stood fretfully outside the housemaster’s study. Steve could see his reflection in the shiny brass plate. He knocked nervously, waited for the call, “Enter”, turned the heavy handle and pushed open the door.

It was a large room with a desk in front of a bay window looking out onto the quadrangle. To one side was a two-seater sofa; on the other, a wall of books. There were a couple of straight-back wooden chairs in front of the desk, but the sixth formers knew they wouldn’t be invited to sit. The chairs would have a different function that morning.

Doughty sat in a leather swing chair glaring. The two teenagers stood meekly in front of the desk, eyes downcast at the patterned rug beneath their feet. Neither boy dared look straight ahead. They did not want to meet the icy stare of the housemaster. But worse than that, behind Doughty’s shoulders, screwed to the wall, was an ornate rack containing four yellow crook-handled rattan canes.

The boys shifted uneasily. Behind them an open fire blazed away. The heat was intense.

Doughty’s tongue was stuck to the roof of his mouth. He wanted to rip into the boys and tell them they were “disgusting perverts” but the tongue wouldn’t cooperate, except to make sputtering noises.

Eventually, he formed coherent words. “Revolting,” “Repulsive,” “Disgusting,” “Nauseating.”

Adam and Steve stood in silence, guts churning.

“I have the honour of the school to protect,” Doughty was in full flow now. “If I report you to the police, as indeed I could, it would do irreparable harm to the reputation of St Simon’s.” He watched carefully the boys’ reactions. Both were simultaneously deathly pale and sweating profusely.

“So, I will deal with the matter myself. Here. Now,” he growled.

Steve’s face flushed with relief. Adam stared impassively at his shoes.

“It will be a flogging,” Doughty croaked, suddenly his mouth drained of saliva.

He cleared his throat. “Stand facing the wall. Hands on head.” He watched intently as the two teenagers shuffled meekly into position. With hands on head, the tails of their blazers rose up their backs uncovering their backsides. Steve’s pale-grey trousers clung to his buttocks, so that each cheek was defined, the crack sharply divided by the seam of his trousers. Adam was quite different. His trousers appeared to be a size or two too large. Grey material folded across his backside and it was impossible to see where one buttock cheek ended and the other started.

Doughty heaved himself from his chair and walked to the front of the desk. He lifted the two straight-backed chairs closer to the middle of the room and arranged them so they were back to back. Then, he returned to his desk and reached up to the cane rack. All four canes were roughly the same length, a little over three feet, not counting the curved handles. They were of differing thicknesses and densities. He chose the cane at the top of the rack; it was a dark yellow and a little warped from age and use.

He flexed it thoughtfully between his hands. His mouth dried once more. He wished he had had the foresight to bring a glass of water from the staff common room.

“White. You first. Turn around.” Doughty swished the whippy cane through empty air. It made a terrific whooshing! sound as it went. Every nerve in Steve’s body seemed to him to jangle. Pins and needles shot up and down his arms. Slowly he turned. He saw the wicked rod in Doughty’s hands and the boy’s entire body succumbed to uncontrolled shaking and trembling.

“Stand there,” Doughty pointed the tip of his cane at a spot by the chair. Steve stumbled across the study, unable to fully control his legs.

“Hands on head.” Steve’s cobalt blue eyes dimmed. He couldn’t stop them blinking fast. Doughty stared into the teenager’s open face. The schoolmaster hadn’t before noticed how clear the boy’s skin was. In his present predicament, it was almost translucent. The wretched boy’s long curling eyelashes beat up and down. His usually smiling lips were downturned into a deep frown.

Doughty hesitated for a second, then he reached forward and unfastened Steve’s belt. He sensed the teenager’s shock as he fumbled with his zip and the front of his trousers fell open. Once done, Doughty gripped their back and lowered them to Steve’s ankles. Steve’s eyes closed. Doughy hesitated for another second before he gripped the back of Steve’s gleaming white Y-front underpants, inserted his fingers in the waistband and pulled them down exposing the boy’s limp cock and balls.

Steve opened his eyes in shock. They moistened immediately.

“Kneel on the chair,” Doughy tapped the wooden seat of one, “and stretch yourself across the back and hold on to the other chair.”

Steve stood rooted. He couldn’t move. His legs shook so violently he feared he would faint to the floor. “Get on with it,” Doughty couldn’t stop looking at Steve’s long, thin, cut, cock. Steve didn’t know how he willed himself to move. Soon he was in position, kneeling on one hard wooden seat and stretching across two chair backs to stare down at a different worn wooden seat. His knees hurt terribly.

Doughty walked slowly around the prostrate boy. With his back arched and his legs apart the housemaster had a perfect view into Steve’s hairless crack. The boy’s buttocks were as smooth as a baby’s and his ball sack and cock dangled.

The buttocks trembled and Steve’s hole winked open and shut with nervousness. Doughty gripped the boy’s blazer and tugged it up his back. Now there were several inches of bared back. It was as hairless as the boy’s bottom. Doughty gave the naked bottom a preliminary smack with his open palm. There was a sound of flesh meeting flesh. The bottom wobbled at the contact. Steve, his face in close proximity to the chair seat, gave a sharp gasp. This was mortifying.

used drawing cane hold (28)

Doughty raised his cane. Bent across two chairs, Steve was in the perfect position for his punisher to whip the cane at force into the fleshiest part of the backside. Doughty placed the cane just below the apex of the mounds and rubbed it backwards and forwards. He felt Steve’s body tense. The buttocks clenched. Steve gripped the wooden chair so hard his knuckles began to whiten.

He felt the cane move away from his bared bottom, there was a second or so pause and then an almighty whooshing noise resounded around the study. Steve felt the intense agony a split-second later. It felt like the housemaster had pressed a red-hot wire into his rear. Saliva washed his mouth. He choked. For a moment he feared he would gag and send a stream of vomit across the room. Instead, a deadly howl screeched from his throat. His body shuddered, his hips juddered and his head bounced up and down.

Doughty observed with great satisfaction as a dark red welt formed across the very centre of Steve’s previously snow-white bottom. Suddenly and without warning a tremendous rage engulfed Doughty. How he hated the pretty boy whose arse was now wobbling in agony across the hard wooden chairs. The same boy he had caressed in his dreams.

He raised his right arm high and brought the cane down with tremendous power again and again in mighty strokes. Deep red welts crisscrossed the firm young buttocks and Steve yelled out his torment uncontrollably, tears pouring down his pale cheeks. Lumpy red welts blossomed under persistent lashes from the raging housemaster. Steve yelled in torment, his body flailing as each new cane stroke whipped into his agonised buttocks, now red raw from the relentless bombardment. His crimson bottom humped up and down frenziedly.

Doughty gave him twelve strokes in total. When he had finished a tense silence fell in the study as Doughty’s eyes focused intently on the Steve’s flogged buttocks, the deep dividing cleft, the glimpse of fair curling hair at the confluence with the thighs. Steve silently gulped in great draughts of air, filling his lungs. Tears flowed like a river going downhill. His chin was covered in snot.

Adam stared in wonder. He had witnessed each frenzied stroke of the cane as it cut his lover’s bare arse to shreds. His own head popped as blood thrashed through his body. He could hardly catch his breath. Adam gaped as he watched Steve’s body wriggle and writhe as the teenager fought to come to terms with the agony travelling through his entire body from his savaged buttocks.

Doughty swished the cane though the air and wobbled it in Adam’s face. “Your turn,” the master growled. “Trousers, pants down.”

Adam stood fixed to the spot. Rooted. No way could he take down his trousers. The humiliation would be too great. Doughty flexed the cane between his two hands and stared intently at the school prefect standing before him. Sweat poured down the teenager’s brow, his face was deathly pale. Doughty’s lips curled. He lay down the cane on his desk and silently reached for Adam’s belt buckle. Within seconds, the trousers and pants were at the eighteen-year-old’s knees revealing his rock-hard erection glistening with pre-cum.

Picture credit: Unknown

This story was first published in December 2016.

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More stories from Charles Hamilton II are on the MMSA website


Charles Hamilton the Second