An encounter

Thwack! The cane bit deep into Dunmore’s bared buttocks. Hisssss! That hurt. A lot.  Swipe! A second cut fell. “Ouch!” Mr. Pritchard might look like a wizened old man, but he could certainly pack a punch. Dunmore clenched his teeth, clutched the seat cushion of the sofa and braced himself for number three.


Twenty four hours earlier

Mr. Pritchard sat idly at the Brocklehurst bus station. A coach from London had just pulled in and he watched the passengers disembark. There weren’t many. A boy holding a plastic bin bag stood still, uncertain, scanning the numbers on the bus stops. Satisfied, that he had found the right one, he shuffled across and stood in the eye line of Mr. Pritchard.

He was an unusual looking boy. Mr. Pritchard thought of him as a boy, but he was easily in his mid-twenties. But, when you were Mr. Pritchard’s age a twenty-something was a “boy.” It was a mid-summer’s afternoon and the boy was dressed for winter, in long thick corduroy trousers and a hoodie top. All the other boys were in tee-shirts and cotton shorts.

His face was pale; he hadn’t seen much sun that summer and his hair was cropped short. It didn’t suit him, Mr. Pritchard thought. It should be much longer. Cropped hair emphasised the boy’s angular face and made him look sad.

Mr. Pritchard noted his broad chest and shoulders; he probably worked out a lot. He had great legs and when the boy turned slightly Mr. Pritchard admired his round firm bum.

Suddenly, the boy blushed. Mr. Pritchard looked away sharply. It was too late, he had spotted the old man checking him out.

“Mr. Pritchard?” It was a statement, posed as a question. The old man looked blank.

“Mr. Pritchard. I’m Dunmore, Michael Dunmore, I was in your maths class at St Francis.” The boy spoke from a distance, making no effort to move closer, to share intimacy.

Dunmore, yes Mr. Pritchard remembered Dunmore. He had been expelled after he was involved in a break-in at the school. There followed a period of unemployment and dead-end jobs. Petty crime led to the inevitable. It had been reported in the local newspaper and it was the talk of the masters’ common room at the time. Dunmore had been sent to prison. That would explain the boy’s pallor.

Just then, a number seven bus pulled up, sparing Mr. Pritchard’s embarrassment. He rose from his seat.

“Do you still live in The Avenue, Mr. Pritchard?”

Mr. Pritchard smiled weakly and boarded his bus.

It was seven-fifteen precisely. Mr. Prichard knew because the theme tune of The Archers was playing. The knock on the door was unexpected. Mr. Pritchard lived alone and he didn’t get visitors. It was probably somebody selling dusters.

Without checking his security spy-hole, he opened the door. It was Dunmore standing on the doorstep. He still wore the corduroys and hoodie and carried his bin bag. He hopped from foot to foot like a naughty schoolboy in front of his housemaster.

“Hello, Mr. Pritchard.” He seemed embarrassed, as if unsure how to say what he had come to say. Mr. Pritchard pursed his lips. He hoped there wasn’t going to be a scene.

“You see Mr. Pritchard,” the boy began. He smiled and his grey-blue eyes sparkled. “It’s hard to explain.” It wasn’t that difficult, he had rehearsed his lines. He had a plan.

“My mum won’t let me stay with her. I’ve got nowhere to stay, Mr. Pritchard.”

Mr. Pritchard gazed into the boy’s pale face, noting the smooth skin and kissable lips. Dunmore gazed back.

“Can I stay with you Mr. Pritchard?” And then he added, untruthfully, “Only for tonight.”

Mr. Pritchard’s heart skipped a beat. Without thinking of the consequences, he stood aside and let the boy enter.

“Do you want something to drink, have you eaten?” They were in the kitchen and Mr. Pritchard twittered like a schoolgirl.

Then the overpowering stink caught him. Stale body odour. It was so strong, he thought he might gag.

He cleared his throat. “Would you like to take a shower? Do you have clean clothes?”

The boy was right out of clean clothes.

“Don’t worry, I’ll try to find you something. Top of the stairs. Go along.”

Mr. Pritchard’s eyes followed the boy’s buttocks snug inside tight corduroy as they slowly ascended the stairs. The boy entered the bathroom and there was a click as the door was locked. Mr. Pritchard sighed inwardly, imagining the boy naked under the warm water, rubbing soap over his buttocks and crotch.

Ten minutes later, Dunmore sashayed into the kitchen, a bath towel tied loosely at his waist. Mr. Pritchard’s eyes moistened. The boy’s upper body was clear and mostly hairless, save for a small mat in the centre of the well-defined chest. It took an effort for the old man not to reach out to tickle it.

Young men learn a lot in prison and pretty boys learn more than most. Dunmore figured if he gave Mr. Pritchard a little he would get a lot back in return. He had already made a reccee of the upstairs room. One was locked but the others proved Mr. Pritchard was not short of a pound or two. He could do very well here.

“Here, these boxer shorts might fit,” Mr. Pritchard handed them to the boy. “They’re clean.”

They belonged to Terrence, he wouldn’t mind. Terrence was also an ex-pupil at St Francis. He had enjoyed his visits to the housemaster’s study a little too much. After he left school he searched out ways to relive the experience. He stayed with Mr. Pritchard some weekends. They had rigged up one of the bedrooms as a headmaster’s study. It was small but there was enough room to swing a cane.

“Thanks,” Dunmore reached for the shorts and studied the label. Thirty inch waist. They might be a bit tight. Then, making sure that Mr. Pritchard had a full view, he let the towel slip to the floor. Good, the old man’s tongue was almost hanging out. Look at that cock old man, do you want some?

Slowly, he turned his back on the old man, stepped into the shorts and wriggled his buttocks provocatively as he pulled them up.

They sat watching television and talking. Dunmore wore only snug-fitting white boxers. He stretched and flexed his muscles, sneakily teasing the old man. Mr. Pritchard was captivated. He hadn’t been so close to youthful flesh since he was himself young; and then only rarely. Terrence only liked to dress in school uniform to have his backside blistered. He was not interested in sitting around in his underwear.

Michael Dunmore was honest. He told Mr. Pritchard all about his thieving and its consequences. He reckoned the old man probably knew already. Brocklehurst was a small town.

“Well, you’ll have to behave yourself in my house,” Dunmore’s beauty had made Mr. Pritchard skittish.

“And, if I don’t?” the boy beamed, egging him on.

“Then, you’ll have to be spanked.” Mr. Pritchard blushed. It had just slipped out. He hadn’t meant to admit it. He wanted that boy’s bum across his knee.

Dunmore giggled, “Well, you can try.” His eyes flashed with merriment.

Mr. Pritchard stood from the sofa, lent across and took hold of the boy’s arm.

“I was joking,” he shrieked with laughter. “I was joking.”

Dunmore allowed Mr. Pritchard to pull him across to the sofa, where the old man sat and pushed the boy face down across his knee.

Mr. Pritchard wasn’t playing. He smacked the palm of his hand hard across the seat of the tight boxer shorts. The cheeky sod needed a damn good spanking and that’s exactly what he would get.

Dunmore stared down at the sofa cushion and let Mr. Pritchard get on with it. The boy could break free at any moment and if he wished he could punch the old man’s lights out. He didn’t want to. Okay, so this was Mr. Pritchard’s thing. Who would have thought it, a schoolmaster got his rocks off by spanking naughty boys.

Slaps rained down across Dunmore’s hard bum. It was a proper spanking. But, a twenty-five-year-old wasn’t going to feel much. Before long, Mr. Pritchard realised his own hand was hurting a lot more than the boy’s bum.

He stopped and released Dunmore, who jumped up and down rubbing his bottom exaggeratingly. “Ow, ow, ow, that hurt,” he pouted, acting out like a small boy.

Mr. Pritchard flew from the room. He needed the bathroom and quickly.

When he looked back on it later Mr. Pritchard could see he had been a damn fool. What did he expect would happen? He had taken a convicted thief into his house. A jailbird. It was inevitable.

It was only five pounds, Mr. Pritchard could afford it. If the boy had asked him for it, he would have given it to him, he was that infatuated by the boy. But, Dunmore had stolen it; from his wallet. That hurt. Mr. Pritchard knew he was being taken for a chump.

There was a confrontation from Mr. Pritchard. An admission from Dunmore.

“You know I could tell the police. You’ll go back to jail, probably,” Mr. Pritchard didn’t know that for sure. Maybe not. Not for five pounds. But the boy would be in big trouble.

“But, I could deal with it myself,” Mr. Pritchard glared at the boy.

Dunmore smiled. He was pretty sure what the old man would say next.

“I have a cane upstairs. I’ll put it across your backside.”

Well, Dunmore thought, there was no surprise there. The old man got his kicks beating boys’ bums after all. But five pounds was a cheap price for “six-of-the-best.” Rent boys probably charged their clients much more. He should have stolen twenty.

“And then you will have to leave my house.”

That wiped the smile off the boy’s face.

“But …” he began a protest, but was cut short.

“I don’t care if you have nowhere to go. Sleep in the street.”

He wasn’t in a mood to argue. “Wait in the living room, I’ll only be a minute.”

Mr. Pritchard calmly ascended the stairs. He unlocked the headmaster’s study and entered. He knew exactly what he wanted. Dangling from a hat stand in the corner of the room by their curved handles were two rattan canes. They were authentic school canes; he had pinched them from St Francis. One was thicker and denser than the other. It was an awesome specimen. It would scar the boy’s backside terribly; especially when applied across bared buttocks.

He slipped the cane under his arm and returned downstairs. He had half expected to find the house deserted. There had been plenty of time for Dunmore to make an escape. But, the boy had not. He took the old man at his word; he didn’t want to explain himself to the police.

Mr. Pritchard had been a schoolmaster for more than forty years. He knew how to “jaw” a naughty boy. He itemised Dunmore’s faults, expressed “deep disappointment” at the boy’s dishonesty and threatened the direst consequences if ever the boy erred again.

Then, he got on with it.

“Trousers and pants down. Bend over that sofa.” He swished the cane for emphasis. The forlorn look on Dunmore’s handsome face delighted him.

The boy had a bum that cried out to be beaten and Mr. Pritchard would enjoy doing just that. It would be both punishment and pleasure.

“I am sorry, really I am,” Dunmore cracked a smile. He knew from the moment the old man had spotted him at the bus station that he fancied him rotten. He had let the old man smack his bottom the previous night and Mr. Pritchard had popped wood strongly. The caning would probably make him cream his pants. If Dunmore played his cards right the old man would let him stay; he would not want to miss the promise of future action.

“I am sorry Mr. Pritchard. I have let you down and I deserve a sound caning.” Dunmore gazed at Mr. Pritchard, sparkling his beautiful blue-grey eyes as he spoke.

Without waiting for a response, he tugged at his belt, loosened it and set about pulling down his heavy corduroy trousers. All the time watching Mr. Pritchard’s reaction. The old schoolmaster avoided the boy’s stare.

“Underpants too,” he growled.

They followed the cords to Dunmore’s feet.

“Bend over.”

Dunmore faced his punisher and wriggled his hips a little so that his cock shook. Then, he turned on his heels and without missing a beat lowered himself over the back of the sofa. He parted his legs a little so that his crack was open and presented his buttocks for beating.

It was one of the cutest arses Mr. Pritchard had ever seen; round and firm. Terrance had a bottom to die for, but this surpassed even that.

Dunmore closed his eyes. This would hurt terribly, of that he had no doubt. But, if he was going to save the situation, he must let Mr. Pritchard have his way.

Slash! The cane slashed into his buttocks. Hisssss, that hurt.

Mr. Pritchard admired his handiwork. A stipe across the crown of both buttocks was already turning deep red. It was a scorcher of a cut. Swipe number two fell a little lower and at an angle. The boy groaned. He felt that all right. Mr. Pritchard raised the cane high and thwacked it down on the under-curve of the buttocks. It was a beauty. Dunmore clung onto the seat cushion and marched his feet up and down in a futile attempt to stamp away the pain that now shot from his bottom and up and down his legs.

Two strokes bang-bang without respite had the boy’s buttocks quivering. His stomach rose from the back of the sofa and only with a super human effort of will did he stop himself jumping up to rub furiously at his ripped bum.

Then came another two. Mr. Pritchard put strength into his stokes, but not accuracy. The boy’s bum was criss-crossed with red lines; it resembled a railway map of Clapham Junction. Bang-bang: two more. Then, another two.

Michael Dunmore was a tough nut to crack. He had endured many things in jail (that was the curse of the pretty boy) but he had experienced nothing like this. The agony in his arse was searing. It felt as if someone had run a hot smoothing iron across it. Every part of his bum throbbed; it felt as if it had swollen to twice its normal size.

Mr. Pritchard was relentless. Six more fell in quick succession. Dunmore’s resolve to take this thrashing quietly broke down. Gentle sobs became gulps; yelps turned to yells and then to shrieks. He was literally a beaten boy.

Then six more. Dunmore wriggled and he stamped and he twisted this way and that. He banged his head up and down against the back of the sofa.

Then it was over.

He laid face down, his bum ripped to shreds. He swallowed down great gasps of air, desperately trying to fill his lungs. His blood pressure was off the scale and his temples pulsated.

Mr. Pritchard was disappointed. The thrashing was a job well done. The evidence for that was before his eyes. But he hadn’t enjoyed it. Dunmore’s gorgeous bum was just a piece of meat. It gave him no thrill.

“Stand up,” Mr. Prichard hoped his voice didn’t betray his disappointment.

Dunmore was quickly regaining composure. His breathing was more normal and his heartrate steadier. The boy’s beautiful face was scarlet and his grey-blue eyes shone. Tears stained his cheeks and snot dribbled from his nose.

He stood in front of Mr. Pritchard, affording him the opportunity to admire his long thick cock and balls. The old man looked away; no longer interested in the boy’s beauty.

“Get dressed,” he barked. He wanted Dunmore out of his house.

Two minutes later the boy stood on the doorstep, his black plastic bin bag in his hand.

Inside the house the phone rang. It was Terrance.

“Yes, of course, you naughty boy, report to my study on Saturday.”


Other stories you might like

The dope smoker

The vicar and the gay boys

A maintenance spanking



More stories from Charles Hamilton II are on the MMSA website


Charles Hamilton the Second


Professor and the fresher student


“Go and stand by that chair,” the professor instructed the boy as he strode to a desk.

The student stood his ground, apprehensively watching as the professor pulled open a drawer and began to fish inside. In no time, he pulled out a well-waxed cane and turned to the boy.

“I said stand by the chair boy!” The professor was in a bad mood.

The pale-faced student stuttered, “Can’t we talk about this Sir?”

The boy was one of the new first year students, eighteen years old and a product of some council board school somewhere. The professor couldn’t understand it. The school had never used corporal punishment, and this was a result.

Now, he was expected to deal with students who knew nothing about discipline – they thought they could do as they pleased without consequences.

Well, the student was about to learn a very important lesson: actions do have consequences. Or, in his case inactions: he had skipped the professor’s class without an excuse and now here he was in the study about the get his just desserts.

“I said stand by that chair. Do it now!” The order was barked out and the student reluctantly turned to face the armchair. It was old and a bit shabby. It had obviously seen better days and was worn across the back and on the seat cushion. The student wasn’t to know, but generations before him bending over to receive beatings had contributed to this.

The professor stood behind the boy making a few practice swishes with the cane.  The student was a good three feet away from the chair. “Closer boy,” the professor ordered. The student turned to remonstrate one more time. “But, Sir.”

The professor swished the cane one more time. Calmly he said, “You will bend over the chair this instant. If you delay you will get double the number of strokes.”

That was it. The boy may never have been in this position before, but he knew when he was beaten. Or more truthfully, when he was about to be beaten.

He took a deep breath. He knew his number was up and events had to take their course. In one almost athletic movement he bent across the chair – like diving into a pool of ice cold water. He clutched onto the seat cushion as if his life depended on it.

“Legs further apart boy,” the professor ordered, giving the cane one more swish.

For a moment he stood and observed the boy. He was a typical student of the day. No more than five-feet-seven, slim, but not muscular, dressed in Wrangler jeans and a god-awful multi-checked jacket that was all the rage with young men at the time. He stepped forward and raised the back of the jacket, its two vents making it easy to expose a denim-clad backside. He took time to take in the information on the label on the waistband of the jeans: twenty-eight-inch waist and thirty-inch leg.

The professor could see the boy was breathing heavily. Of course, he’d never been across a headmaster’s chair for Six before. This was entirely unchartered territory for him.

Not so for the professor. He was of the old school. And here ‘school’ was the operative word. He knew that his students (well, most of them anyway) had just left independent private schools where they were subjected to discipline and if they stepped out of line, they expected punishment. And they got it from him: in the form of a caning.

University was to be no different for them. The professor had rules and you obeyed them. If you didn’t you would expect to receive a summons to the study. And, as this student was about to find out what happened next would be very painful indeed.

The professor grabbed the boy’s jeans by the waist and pulled them up tight. The denim formed a second skin across the most pert of buttocks and made a perfect target for the thrashing.

Most of the students those days wore denim jeans. It was just a fashion, but if boys thought the denim cloth gave them more protection against the whippy cane, than, say, the trousers they would have worn at school, they were to be sorely mistaken.

There was one type of jeans that did cause problems. These were called Falmers and they had big pockets across the backside. They had folds of cloth and definitely were a hindrance to the punisher.

The professor had found a simple remedy to this. Once a boy had attended for punishment in such jeans, he was ordered to drop them to his ankles. Then it was over the chair for a swishing on the underpants. A rather fetching pair of bright red briefs, the professor reminisced fondly. Once word got around about this nobody tried that trick again.

So, here was the student, over the chair, in his Wranglers ready to take the first stroke.

The professor believed in the efficacy of corporal punishment. It wasn’t used as a ‘last resort,’ for him it was the first. If a student disobeyed the rules, he was over the chair and the cane would be sent bouncing down across his stretched backside.

As was to happen now. The professor took up position to the left of the boy and tapped the cane against his nearest buttock. Finding his spot, the professor bent his own knees slightly drew the cane up to beyond shoulder height and sent it crashing against the boy’s tight backside.

The student gasped, but managed to muffle the yell he desperately wanted to make. His legs shook slightly and his hands grabbed the cushion of the armchair tightly.

The professor observed a clear mark had formed in the denim, extending across both cheeks in a thin line.

The second stroke came crashing down, a quarter of an inch below the first. The professor had an expert aim. After all, he had plenty of experience in this.

The third and fourth cut bit into the boy’s backside in rapid succession. By now he was losing control. The gasps became yelps.

The professor paused before stroke five, knowing that the pain would be searing across the boy’s backside and through his legs. The student’s breathing was uneven. The professor looked over the chair to see tears flowing down the boy’s face.

Swish! Whack! Number five hit home. The boy made a move to rise himself from the back of the chair. But at the last moment he forced himself back. This might be his first beating, but some schoolboy instinct told him to stay in position: he didn’t want extra strokes.

The boy lay waiting for what he hoped was the last stroke. The professor hadn’t announced it was to be six-of-the-best. But surely that was the tariff. Six was more than enough, Sir. This was a first offence after all.

The student could feel welts forming under his pants where five parallel strokes had hit home. No, they had done more than hit home, they had been struck with such force they had gone through the flesh in search of bone.

Number six was the worst of all. The professor paused, took three steps backward, raised the cane in the air and then rushed forward and struck.

The sixth stroke was laid diagonally across the previous five, creating a five-bar gate, cutting each welt and creating searing pain. Surely, later when he inspected the damage, the student would find blood seeping from the wounds.

The boy was gone, tears came in huge gulps, he wanted the pain to end, to curl up in the foetal position and die.

The professor watched him writhing across the back of the chair, satisfied with his own handiwork.

“Stand up boy,” the instruction was gentle, no longer an order. The punishment had been delivered and although the student had taken it, if not well, he had not resisted. He now belonged to the professor.

The eighteen-year-old boy rose from the chair, unsure where to go first. To try to wipe his tears and the snot that was coming from his nose, or to send both hands to clutch his buttocks in an attempt to rub away the agony.

But he didn’t have time. “Turn and stand in front of me,” the professor said. He complied, his eyes firmly fixed on the carpet in front of his feet.

“Look at me when I’m talking to you boy.” He raised his eyes. “Will I need to do this again?” The student hardly had the breath to give the required response.

“Good. Because if I do we shall see how you like it with your trousers and your underpants around your ankles.”

No response, except gulps and sobs from the student.

“You are dismissed.”

The professor watched the student hobble to the door in considerable discomfort. He turned the handle, opened it and was gone.

The professor replaced the cane in the desk drawer, alongside the seven or eight others there.


Other university-based stories you might enjoy.

Professor Paddle

The Senior Tutor

The sting in the tail


More stories from Charles Hamilton II are on the MMSA website


Charles Hamilton the Second

Naughtiest boy in the school?


Roland was bent over, hands placed firmly on his hairy knees, legs planted apart, staring down at the shiny, highly-polished tan floorboards. His mid-grey trousers were in a puddle at his feet, hiding his scuffed black lace-up shoes. His green-and-gold-striped tie dangled in front of his face.

Roland could have been the naughtiest sixth-former at St. Francis Independent Grammar School. This wasn’t his first time he was in this position and it certainly wouldn’t be his last.

Mr. Trout had his rituals at such moments. He waited until a boy was bent double, hands on knees, backside jutted out. Then satisfied that the buttocks were perfectly positioned to receive the administrations of his whippy rattan cane, he would take hold of the elasticated waist of the white school-regulation Y-front underpants. He would pull them tight so they created a wedgie effect, drawing tight cotton up into his crack. An inexperienced boy might think Mr. Trout was preparing the underwear so that it formed a second skin against the meaty buttocks.

Frequent visitors to Mr. Trout’s room knew better. The elderly man was merely toying with the quivering boy, bent submissively before him. For Mr. Trout had only one intention. He would release his grip on the pants and then count silently up to ten. Then, in a flourish like a magician whipping away a cloth, he would retake his hold on the waistband and tug the underpants down, across the mounds until they rested at the thighs. Usually, gravity helped them to slip down to the boy’s knees. Only later, once the thrashing was underway would the writhing of the punished lad take them down to meet his trousers.

Another part of the ritual went like this. Mr. Trout had not yet selected the cane he would use. He liked to leave the boy bent over, bare arse to the wind, while he sauntered to a tall thin cupboard in one corner of the room. Roland, even in his prone position was able to watch Mr. Trout’s legs as he moved about his business. They were sturdy legs, encased in expensively-tailored black trousers with white stripes. Roland could not recall ever seeing such trousers worn by anyone but Mr. Trout. A tatty academic gown hung loosely from Mr. Trout’s shoulders. In his bent-over position, Roland could not see the mortar-board cap balanced precariously on the housemaster’s head.

Roland raised his body slightly, but still with his palms firmly pressed into his knees (for he did not want to give Mr. Trout cause to award him extra strokes) and watched as the elderly man rummaged into his own trouser pocket and retrieve a ring containing several keys. Mr. Trout fumbled until he found the correct one which he inserted into the cupboard lock.

Mr. Trout’s back obscured Roland’s view. It made little difference because Roland already knew what was contained therein: a selection of school punishment canes of various lengths, thicknesses and density. Mr. Trout scrutinised the inside of the cupboard. Roland heard the tell-tale rattle as canes were moved about to facilitate the elderly man’s search for the exact rod he wanted to take the misbehaving boy’s backside off.

Roland saw Mr. Trout’s feet shuffle as he reached in and took hold of his weapon of choice, then he closed the cupboard but did not lock it. His feet moved sideways as he slowly made his way back to where Roland waited submissively. This was the part Roland anticipated most. He had been beaten many times before, and not just with a whippy rattan cane. His backside had been blistered with leather tawes, rubber-soled gym shoes and wooden-backed hairbrushes. Each implement could inflict the severest pain, but each spanking and beating he had ever received – and there were too many for him to count – had its own unique property. At the point he waited for the first blow to land he could not know for sure just how painful it would be.

Mr. Trout liked to put a lot of beef into his beatings. It should be excruciatingly painful. What was the point, he would often say to Roland, of beating him otherwise? It should be awesome; something that the boy would not forget in a hurry.

Roland watched Mr. Trout’s feet. His brogue shoes were highly polished. They now stood to the boy’s left side. He could hear the elderly man swipe the cane through empty air. He stood so close to Roland the boy felt a breeze against his naked bum and legs as the rod whistled by. Mr. Trout planted his left foot firmly on the floorboards, and stretched the other away to the right, while also bending the knee. Roland took this as his cue. He couldn’t see, but he knew Mr. Trout was about to raise the cane way above his own head. The boy shut his eyes tightly, clenched his teeth and waited for the inevitable pain.

Mr. Trout was an expert with the cane. His eye was perfect; not for him the constant tap, tap, tap of rattan against bare flesh as he took aim. Instead, he simply raised the cane high and brought it smashing down across the very centre of Roland’s two buttocks. Bullseye! The rod sank into Roland’s bum and immediately bounced off, leaving behind a white stripe. Mr. Trout waited; he was in no hurry. Within seconds the white had turned to a deep pink. The faintest welt was rising.

Roland rocked on the balls of his feet; his mouth opened and closed, but he made no sound. A sharp pain attacked his rear, but very quickly it turned to a warm glow. He had absorbed stroke number one. Mr. Trout had not announced a tariff; Roland had not been told how many cuts to expect. Of course, it was traditionally six-of-the-best. Schoolmasters across the ages had been punishing their charges in such a manner. But, Roland was a recidivist, a repeat offender, the days when Mr. Trout considered six strokes a sufficient punishment had long past.

Roland watched once more from the corner of his eye as Mr. Trout positioned his feet. When he had judged that the hurt was ebbing away: Swipe! Number two fell, maybe a quarter of an inch below the first, but there was still plenty of room on Roland’s bottom for lots more strokes. The pain rose sharply to a new peak.

By the time he had finished the whole of Roland’s bottom, from the top of the mounds, across the very apex of the cheeks and into the fleshiest underside where the bum nearly meets the thighs would be covered with perfectly parallel lines. That was only if the boy was able to maintain his position manfully under the onslaught.

If he could not and his bum wriggled and squirmed or his legs buckled and he hopped from foot to foot; or, if his hips swayed backward and forth. If the wretched boy made any of these movements, it would destroy Mr. Trout’s aim. If that happened strokes might land in the same place more than once. The pain Roland already experienced would transmute to intense agony, as the pain from an existing ridge would be reignited. Blood might also weep from wounds at the points where one weal intersected with another.

Roland had a high pain threshold. He could take one heck of a beating stoically. But Mr. Trout knew how to lay on a caning with some vim. The pain in Roland’s backside mounted as each successive stroke connected with his jutting backside. His heart raced, blood coursed through his arteries, he found it difficult to catch his breath.

Roland rarely yelped or yelled during a thrashing. Instead, he would hack a dry cough after each swipe bit deep into his stretched flesh. This was unusual for a boy being punished. The first time Mr. Trout thrashed him, the elderly man had become concerned. He genuinely feared the boy might be in need of medical attention. The last thing he wanted was for Roland to vomit all over his expensively-polished floorboards.

Two more cuts landed, one after another. “Yowch!” Roland gasped, his face scrunching up with the pain in his bum. But, he managed to stay in position, hands on knees, face down staring at the floorboards, bum jutted out. But, three strokes later, his knees buckled and his torso twisted and he let out a shrill scream. The agony was too much; even for him. The next cut had him fighting back the tears.

Eventually, Mr. Trout’s shiny shoes disappeared from his sight. He knew then that he was returning the cane to its place in the cupboard. But, still Roland waited, his bum ablaze with pain.

Mr. Trout had a ritual to end his canings. He slapped Roland with the palm of his hand on his raw, corrugated rear. “Ouch!” he cried, and wriggled his blistered bum from side to side. It hurt almost as much as a stroke of the cane.

“You may stand,” Mr. Trout intoned. Roland blinked and straightened up. He saw the elderly man gaze at his cock and balls. He had seen them many times before and much more besides while Roland presented to him his bared bottom.

Roland tugged first his Y-fronts and then his grey school trousers into place. “Thank you,” he smiled courteously.

“You’re welcome,” the housemaster replied as he rested his backside on the edge of his desk. “And how is your wife? I read she was recently appointed Under Secretary of State for something or other. It keeps her very busy in London, I presume.”

Roland nodded, “Yes, I hardly ever see her.”

Mr. Trout rubbed his hands, “I’ll be seeing to you again before she gets back, I presume?” he asked him with a big smile.

“Yes please,” smiled back the thirty-five-year-old former pupil of St. Francis’s. “If you don’t mind.”


Other stories you might like

The housebreaker

Late home from school

The casting couch


More stories from Charles Hamilton II are on the MMSA website


Charles Hamilton the Second


When Santa Claus was caned


Once upon a time there were three Santas. How can this be? I hear you cry. For everybody knows there is but one Santa and he lives on the North Pole. All year round he works tirelessly with his elves making toys. One day a year – on Christmas Eve – he loads up his sleigh and reindeer fly him all over the world. He delivers toys to the nice and spanks the bottoms of the naughty.

Gentle reader, if you believe that you are either five years old or you reside in one of our more discreet sanatoriums.

The three Santas – to make our story easier to follow let’s think of them as Saint Nick, Father Christmas and Chris Crimble – worked six weeks of the year for Jamley’s department store. Their job was to make sure the cash registers kept jing-jing-jingling throughout the festive season. The three Santas were idle for most of the year, but Mr Crimble sometimes gave his services at an obscure gentlemen’s club and Nick would wrap himself in bandages and stand on a street corner selling matches.

St Tom’s was a school for the sons of the wealthier classes. The boys were boarders and at Christmas time they went home to their families. Alas, some of them were unloved. They had parents so rich they did not have to pretend. So, seventeen boys were left to spend Christmas at St Tom’s. Mr Bugg, a housemaster, was unloved too. He was also unloveable. His salary was so miserable he could not afford to rent rooms for the holidays, so he too stayed behind.

This made him a curmudgeon. He knew no joy. Even on the eve of Christmas he prowled the passageways, his whippy cane under his arm, seeking out misbehaving boys. Merrick was a senior boy. He was eighteen years of age. He thought of himself as an adult. “Pish!” Mr Bugg exclaimed when he found the prefect in Study Seven puffing away on a cigarette. “You are no adult, bend over that chair.”

The cane slipped into Mr Bugg’s hand and he landed six top-rated stingers across Merrick’s backside. And Merry Christmas to you too, the boy growled.

Hank the Yank was an American. His father lived in New York. It was too far for the boy to travel home for Christmas, he said. It was too. For this was in the day before ordinary folk could fly the Atlantic. Only Santa and his reindeer could do that. Hank’s pop was extremely rich and had more money than cents. (Ho! Ho! Ho!) He loved to make expensive gestures. It showed people just how wealthy he was.

He arranged with Jamley’s to send their Santa Claus to the school on Christmas Eve. The news was treated with indifference. Even fake Santas were busy on Christmas Eve. The pubs stayed open beyond midnight. No Santa wanted the job.

Mr Blenkinsop, the department store’s assistant to the assistant floor manager, was at his wit’s end. Alas, Nick, Mr Crimble and Father Christmas were all as one. “Sod off,” they told him. “Do it yourself!”

Mr Blenkinsop was hurt. Where was the spirit of Christmas? Those boys were a long way from home, without their families. Alone. His sob story fell on deaf ears. The three Santas were anxious to leave. Mr Crimble had a bottle of dark rum hidden in his coat. It wouldn’t drink itself.

“Oh well,” Mr Blenkinsop sighed. He drew a ten shilling note from his wallet. “There. That’s for whoever does the job.” Three hands shot forward. “To be paid when you return.” Mr Blenkinsop was no fool.

Satisfied that one or other of the old duffers would deliver, Mr Blenkinsop wrapped his scarf around his neck and stepped out into the cool, damp night. This was England. It rarely snowed at Christmas, despite what Dickens would have us believe.

It was nine o’clock in the St Tom’s dining hall. Seventeen boys and one grumpy master tucked into steak and kidney pudding. It might be Christmas Eve but the fare at an English public school never changed. Mr Bugg was more miserable than usual. He had been warned there would be a visitor. Mr Bugg was not a jovial type and he discouraged joviality in others. Two fags engaged in a hilarious game of “slaps” were at that moment irritating him to distraction.

Whoosh! The door sprung open. Eighteen pairs of eyes stared in wonder. It was Santa. Dressed in his big red suit. “Ho, ho, ho …” Chris Crimble slurred as he staggered through the door. Merrick, who until that moment had been in a sulk, dodged as Santa lurched forward and fell headlong across the table. An empty bottle fell from his pocket.

“Ho, ho, ho, and a bottle of rum!” Merrick cheered, delighted at his feeble joke.

“Merry Christmas,” Crimble croaked. The smell of the meat pudding reminded him he had not eaten for hours. He scooped a handful and fed it through his askew whiskers.

“What the devil,” Mr Bugg was on his feet. At that moment. Whoosh! The door opened once more. It was Santa Claus. “Ho, ho, ho, Merry Christmas.” Father Christmas was at least sober. “Hello, boys look what Santa has brought for you.”

“What is it Santa!” the boys cried in unison, for they knew the part they had to play in this little story.

“Here,” Santa delved into his sack and brought out a thin rectangular box. He handed it to Merrick. “Merry Christmas, young man,” Santa grinned. “Why thank you Santa,” Merrick replied grudgingly. For he thought he was too old to be given gifts by Santa Claus. The teenager fingered the box. “Oh my, thank you Santa,” he said again. This time he meant it. For in his hands he held a special gift box of two hundred Player’s cigarettes.

“What the hell!” Mr Buggs fumed. “What is going on here?”

There was no time for Father Christmas to answer. Whoosh! The door opened once more. It was Santa Claus number three. The boys stared in wonder. Could this be true? Three Santa Clauses in one evening. But, what was this? Santa number three was not alone. For Periwinkle, the school porter, clutched Saint Nick by the arm.

“I caught him by the school gate, Sir,” Periwinkle exclaimed. Puzzlement furrowed the brow of Mr Buggs. What on earth?

“He was escaping, Sir. Look.” Periwinkle picked up Santa’s sack and turned it upside down. Five silver trophies cluttered to the ground. Mr Buggs immediately recognised the school’s inter-house rugby cup.

“He was stealing the school silver, Sir,” Periwinkle said, to be certain that everyone understood what was going on.

“Call the police.” It was Merrick, determined to show everyone he was an adult. “At once,” he ordered Periwinkle.

“But Sir, I am but a poor man,” Saint Nick held the palms of his hands together as if in prayer. “A war hero, Sir, a man down on his luck.”

“Oh, per-lease!” Merrick retorted, for his father was the Lord of the Manor and a magistrate to boot. He knew how to deal with the working classes. “Call the police Periwinkle. At once.”

Periwinkle was a man who knew his place. “Will you guard him Sir while I go to the telephone?” he asked Merrick.

“Hang on, one damned moment,” Mr Buggs fumed. “I am in charge here. I will say what is to happen.”

Merrick glowered. How he despised the master who stood before him. “He must go to trial. The law must take its course.” He was a very pompous young man.

“No,” Mr Buggs had a plan. The night had been ruined. Not only by the thieving Saint Nick, but by all three of the Santas. Mr Buggs knew what was needed. He had not been a schoolmaster for thirty years for nothing.

“I shall deal with this. There is no cause to involve the police.”

Saint Nick wrung his hands in gratitude. “Thank ye Sir, thank ye,” he said in poor imitation of a rural peasant.

“Well see about how thankful you are in a moment,” Mr Buggs growled. “Wilson,” he called to a fag. A junior boy stood up. “Yes, Sir.”

“Go to my study and fetch my stoutest cane. Be quick about it.”

Saint Nick’s ruddy complexion paled. A broad smile split Father Christmas’s face. What sport this would be. Chris Crimble stared on, hardly comprehending what was happening.

Moments later Winker Wilson returned, cane in hand. It was a beauty. It was more than three feet long, not including the traditional crook handle. It was as thick as a pencil and a little warped. It was a piece of ashplant and had notches every three or four inches along its length.

Mr Buggs swished the cane through the air. It made a terrific swoosh as it flew. Saint Nick’s eyes watered. He was going to be beaten. In front of the boys. In front of the other Santas. This could not be happening.

“All three of you, stand by that bench.” Mr Buggs swiped the ashplant once more. Nobody moved, for it was not clear what the schoolmaster was talking about. “The three Santas. Stand by that bench,” he pointed with his cane. “I am going to thrash all three of you,” he said. Now, everyone understood the plot.

The three aged men shuffled across the room, for Mr Buggs was a schoolmaster at an exclusive fee-paying school. They knew their place. Such was merry England. He was in charge. There was nothing they could do. Unless, of course, they wanted to spend Christmas in the police cells.

“Bend over.” It was an imperious command. They bent.

Boys’ eyes looked on in astonishment as the cane flogged across three backsides. Dust rose from trouser seats. Merrick’s buttocks itched. The humiliation and pain of his own earlier caning rekindled. He took his chance. He bundled up boxes of cigarettes and took them to his study.

Father Christmas scowled as the pain increased in intensity. Saint Nick shut his teeth tightly, he wouldn’t embarrass himself by showing it hurt. Chris Crimble breathed heavily. Just wait until he told the fellows at his gentlemen’s club what had happened. How they would envy him.

Charles’s note. The drawing at the top of this story is from The Hotspur, an English boy’s story paper dated 23 December 1933. It is an evocative image but the story it introduced had no scene in it that related to the picture. It was what boys of the time would have probably called “a swizz”.

This story is also available in the free-to-download compendium Seasonal Spanking Stories. Click here



Other Christmas stories you might like

The night before Christmas

Only three thieving days to Christmas


More stories from Charles Hamilton II are on the MMSA website


Charles Hamilton the Second

The parent-teacher 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.”

Steve and Adam 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.


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.


Other stories you might like

The pubbing sixth-formers

A whopping for Warminster

By order of the court


More stories from Charles Hamilton II are on the MMSA website


Charles Hamilton the Second

Every Wednesday afternoon


“Take off all your clothes, fold them neatly and put them on my desk.”

The young man stared ahead blankly. His body was in the office, but his thoughts were somewhere else.

Mindlessly, he reached for his wine-coloured necktie and pulled it apart. He set it down on the desk.

The man behind the desk watched intently as the young man pulled the tail of his lilac shirt from the waistband of his trousers. Then slowly he undid each button. He slipped the shirt off his shoulders and folded it in half lengthways. Then he quartered it. He put the shirt on top of his tie.

The man studied the young man’s arms and torso. They were covered in tattoos. There was not a single square centimetre of arms untouched by patterns of all descriptions. They had some meaning, some personal significance, the man supposed. Otherwise why would a person go to the trouble, the expense and, almost certainly the pain, to have them done? Most young people were covered in tattoos these days. It was rare to see one without.

The young man bent down and unfastened the Velcro strips on his shoes. He kicked off first the left and then the right, revealing garish yellow-patterned socks. He bent again and hitched his fingers inside each and hooked them off.

Still not acknowledging the presence of the man behind the desk, the young man unbuckled his belt, popped the metal clip at the top of his dark-blue pin-striped trousers, pulled down the zipper and let them fall to his ankles. He hopped precariously on one leg and then the other to tug them over his feet. Then taking care that the creases down the legs were in place he folded them up and put them on the desk.

He only had the underwear to go. He flushed slightly. It was the only emotion he had shown so far. Without delay he put his fingers inside the elastic waist of the snug-fitting briefs and pulled them down and stepped out of them. The pants felt warm in his hands. He put them on top of the neat pile on the desk.

He stood and waited for the next instruction.

The man behind the desk stared without inhibition at the young man’s cock. It was long and thick, quite the largest he had seen in several weeks. He imagined it might look like a stallion’s when it was fully aroused and ready for action.

“Go stand and face that wall. Put your hands on your head.” The man behind the desk nodded at the wall behind the young man. It was a large office, but sparsely furnished. The desk was huge. It was constructed of some man-made grey material and weighed a tonne. Despite its size there was much empty space. Two heavy cushioned chairs were paced neatly at one end of the desk. A single filing cabinet with four drawers, three of them empty, stood against a wall. Behind him the man had a computer on a stand.

He watched idly as the young man positioned himself. He placed his hands on his head in the classic “naughty boy” pose and stood inches from the wall. The young man was somewhere in his twenties, the man behind the desk supposed. He was podgy. He was not yet fat but unless he started taking exercise or changed his diet he soon would be. The man behind the desk had himself been quite trim until well into his thirties. He went downhill after that. Once you put on weight it was devilishly difficult to lose it. Better not to get fat in the first place.

The telephone rang. The man behind the desk picked it up and listened. “I’ll come straight away,” he said. He rose from his desk and left the room. The young man remained in position. Hands on head. Waiting.

The young man shivered. The air-conditioning was set to icy and he was naked. Many minutes passed. Suddenly, the door to the adjoining office opened. A middle-aged woman entered. She stopped; puzzled. She had expected the man to be at his desk. She looked across at the young man facing the wall, thought for a moment, but decided not to ask her question. She returned to her own office.

At last the man returned. He held a buff-coloured envelope in his hand. He walked to the filing cabinet, took a ring of keys from his pocket and unlocked it. He opened the top drawer and without looking in he slipped the folder inside. He closed the drawer, locked it and put the keys back in his pocket.

He moved to the front of his desk and picked up one of the heavy chairs. It had a straight back and no arms. It was elegant, expensive office furniture. The back and seat was covered in light-grey patterned material. Satisfied that the chair was in a suitable position, the man returned to his desk. He did not sit down; instead he bent down and reached to the lowest of three drawers. He opened it and reached inside. It was empty except for one thing. He pulled out a small wooden paddle.

It was home-made, or more truthfully not factory made. A friend of the man was a DIY enthusiast. He had made the paddle in his garage / workshop. The blade was about twelve inches long and three wide. It had a handle attached. The man held it by this and smacked it into the palm of his left hand as if testing its suitability for the task in hand. This was not strictly necessary since he used the paddle regularly. He knew it was up to the job.

He sat in the chair, wriggled his bottom to get comfortable. Then he spread his legs by a couple of feet or so. He was ready.

“Turn around,” he called over to the young man at the wall. He did so. He was not surprised at the sight that greeted him. “Come here and bend across my knee.” The man slapped his thigh in case there was any doubt what he meant.

The young man’s glassy stare had not altered. He did not look the man in the eye. Instead, he concentrated on the man’s knees as he meekly lowered himself. The young man was quite a weight; much heavier than the others the man had dealt with in recent weeks.

The young man’s face was inches from the heavy industrial-strength carpet. He did not notice its dark blue and black pattern. He folded his arms. Behind him, his bare toes scrapped along the itchy carpet. His bottom was high over the man’s lap.

The man caressed the young man’s back. Carefully, he traced his fingertips over a large tattoo. He did it cautiously, as if he feared the ink might come off on his fingers. It was a tattoo written in a Chinese language. At least the man supposed this to be so. He did not know and in all probability the young man across his lap did not know either. He needed to trust that the tattoo artist knew what he was doing. It might even be a trick. The writing might translate as, “What an idiot I am for permanently disfiguring my body like this.”

The man gripped the paddle and tapped it against the naked buttocks presented before him. The cheeks were slightly stretched and therefore a little tighter than when the young man was standing, but they were still well upholstered.

Smack. The paddle sank into the left buttock, immediately leaving a dark pink mark behind. The man smacked the other cheek and was rewarded with a similar result. Then he whacked the paddle down again and again and again.

The young man across his knee sucked in air with each blow. Then he exhaled slowly. It seemed to the man that this was his way of controlling the pain. The young man crossed his arms more tightly.

Another six whacks were delivered across the lower part of the cheeks, where they start to meet the thighs. The young man crossed his left foot over his right and straightened his knees. More pain control, the man thought.

The hue of the buttocks quickly changed from deep pink to red. The young man was a naturally pale colour and his flesh was quick to register hurt. The red deepened to the colour of a good Burgundy wine.

The paddle travelled across the entire circuit that was the young man’s backside. It started at the top, just below the spine, crossed the fleshiest part of the globes, before biting into the under-curves. Satisfied that no square inch of bum was untouched, the man turned his attention to the thighs.

The thighs are more sensitive to pain than the buttock area. Or so the man assumed, since the reaction he got from the young man was the most animated so far. He crossed and uncrossed his legs and then kicked them wildly. It was instinctive. The young man had no intention of trying to escape or in any way avoid the spanking.

He unfolded his arms and wrapped them around his head.

The spanking continued for about three more minutes. The man rhythmically pounded the paddle into the fleshy mounds across his lap. The young man crossed and uncrossed his legs.

Then it was over.

“Stand up and return to the wall. Hands on head,” the man gave a clear instruction. He said no more. The young man placed his hands on the man’s right leg and hauled himself to his feet. He resumed his position at the wall.

The man returned the chair to its original position and then sat behind his desk. Idly he watched the young man. His bottom appeared to be twitching. It was almost certainly throbbing quite badly, but the pain would quickly turn into a warm glow and then disappear. There were bruises forming in the very centre of the young man’s bum. They would certainly last a day or so.

There was a confident knock at the door.

“Come in!”

Another young man, also in his twenties, entered. He was wearing a dark-grey suit and holding a buff-coloured folder.

“Here’s the report you asked for, Sir.”

He handed it over, noticing the neat pile of clothes on the desk. As he exited, he looked at the other young man’s still-reddened buttocks.

He was not surprised at what he saw. Last Wednesday it had been Knight. The week before it was Powell. Next Wednesday it would be someone else. He knew before too long it would be his turn.


Other stories you might like

The apprentices

Six of the best caning stories 5. The performance review

Caught in their underpants


More stories from Charles Hamilton II are on the MMSA website


Charles Hamilton the Second

Seasonal Spanking Stories


Seasonal Spanking Stories, a compendium of corporal punishment tales, written especially for the upcoming holidays, available to download free of charge.

Nine tales, many never previously published, will warm the cockles of your heart – and other places besides. How was it that three Santas were caned? What happened when a group of delinquents from an Approved School were sent to deliver Christmas presents to destitute children? Learn why you should believe in Father Christmas.

You can download the stories which run to more than 20,000 words by clicking this link.


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.

– Extract from Approved School Santas