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

The room at the top



If people thought it strange that the two men shared rooms at the top of the boarding house then nobody said so out loud. Bob was a little to old to be Ramsey’s elder brother and too young to be an uncle.

Ramsey had recently been released from Lansbury Approved School for young offenders. His career in petty crime had burgeoned until he was considered a threat to society. The headmaster Mr Jossop, a man of Christian principle, rarely had a thick whippy cane out of his fist. Ramsey was no stranger to corporal punishment. Even aged nineteen he found himself resting his forearms on the headmaster’s desk (Jossop’s preferred position) with his back arched and his bottom sticking out to receive eight strokes (the maximum permitted) across the seat of his regulation short trousers.

Bob had an altogether different upbringing. Although he too was no stranger to an ashplant cane. He was a boarder at St Tom’s, a minor public school in the West of England. He was not a success. The word “slacker” might have been invented for him. The headmaster’s ashplant and his father’s razor strop, both administered with excessive vigour across his naked eighteen-year-old buttocks, did not improve his performance. His father removed him from school following an undistinguished set of examination results.

Soon, Bob found himself in the Colonial Service, serving in some godforsaken hole in The Dark Continent that nobody had never heard of. He was quietly asked to return to England following a misunderstanding involving two young African men. So, aged twenty, he was home to receive a further leathering from his father before he was found a position as a clerk in an accountancy business.

That had been six years previously.

Ramsey came into his life by accident. Approved school might have kept the boy off the streets but it did little to prepare him for life. Without a job and often with nowhere to sleep he returned to his life of crime. He did good business in an area of Hampstead Heath where sad lonely men would go for company. Ramsey was a pretty boy and he had endured many humiliations as a result at Lansbury, but he wasn’t prepared to sell his body. Instead, he became a footpad. He robbed at knifepoint.

It was ridiculously easy. They were too scared to resist his blade and none would report him to the police. They would have to explain to the constables why they were walking alone in that part of the Heath after dark. Of course, the police already knew the answer to that.

But one night the tables were turned. Ramsey held his blade to the face of a middle-aged man and was waiting for his wallet to be handed over when he was attacked from behind. His victims had decided to fight back. They left him bloodied and unconscious.

That was how thirty minutes later Bob found him. He knew nothing of the boy’s circumstances. All he saw was a remarkably beautiful body sullied by bruises. Do men have maternal instincts? If so, they were to the fore that night. Bob wiped the blood from Ramsey’s face as gently as a mother washing her new born.

The taxi driver pretended not to notice the boy’s state. He was reassured by Bob’s upper class accent. He knew his fare would be paid and he expected a large tip as well. For he understood the reputation of that area of the Heath and now he also had the home address of one of its users. His discretion would be worth a pound at least.

There was only one bed. They shared it. It was not thought unusual. People of the same sex often did. If the bed was large enough three men could fit in together. At Bob’s school, expensive though the fees were, the juniors had been forced to sleep four-up.

Ramsey knew he was on to a good thing. A regular roof over his head for the first time since he was thrown out of Lansbury. But there was to be a price to pay. He hadn’t thought much about it when he first arrived. It was quite a common thing to see in a home. His own father had one hanging from a nail in the kitchen. It brought back unpleasant memories. Once, when Bob was out the room, Ramsey had taken it down and held it between his hands. An old worn leather razor strop. It even smelt like the one his father had.

But, Bob did not have a cut-throat blade, he used one of the new-fangled ‘safety razors’. How very modern, Ramsey thought. And it saved a fellow from walking around with pieces of damp newspaper stuck to his chin.

It was seven in the evening. Summer was turning to autumn. Ramsey could tell Bob was restless. He paced the room, looking at his watch. Then, he moved to the window, twitched the curtain and peered out into the street below. Then he paced some more.

“What’s the matter,” Ramsey snapped, his nerves jangling. “Are you expecting a rozzer?” He smiled at his own joke. The police, indeed. Could there be anyone in London more honest that Bob?

“I’m waiting for somebody,” Bob rasped. His hands shook as he reached into his trouser pocket for cigarettes.

“Oh,” Ramsey nodded sagely. A woman. He was waiting for a woman. “Do you want me to go for a walk?” he grinned. Bob stood puzzled. “What? No. You must stay.”

In the distance a doorbell rang. Bob darted to the window. “He’s here.” He dashed to the door, turning to Ramsey as he opened it. “Wait here. Don’t move.”

It was some distance from the top room to the street door. Ramsey lay back on the bed, his arms behind his head, waiting. Who was this mysterious visitor? A man, not a woman. Bob never had visitors at the room.

The door creaked open. “Oh yes. Delightful.” It was a man somewhat older than Ramsey, perhaps in his forties. He wore a formal business suit, expensively cut. “My word, yes.” The man beamed. His ruddy complexion shone. Ramsey smelt gin.

Bob closed the door, looked around the room furtively. He locked the door and popped the key in his pocket.

“Wonderful. Oh, yes.” The man ran the tip of his tongue around his lips as if clearing them of salt. “Perfect.”

Ramsey hauled himself off his back and sat with his legs dangling over the edge of the mattress. “Charming.” The man’s cobalt blue eyes bore into the teenager. “Exquisite.”

Bob shuffled from one foot to the other. Unsure. Ramsey sat silently, watching. The man slipped his jacket from his back, held it in his hand and peered around the small room. “Here.” Bob took it and hung it on a nail on the door.

Without taking his eyes off Ramsey, the man unbuttoned the cuff on his shirt sleeve and slowly, neatly, folded it up until his forearm and elbow were bare. Ramsey’s pulse quickened. Who was this man? He returned the man’s blazing stare. He would not be intimidated. Years in the Approved School had taught him; do not show fear.

He did not notice his roommate move to a cupboard, open it, and reach inside.

Satisfied that his shirt was perfectly folded, the man turned to Bob. “Yes, that will do nicely,” he drooled. Alarmed, Ramsey turned in time to see Bob approach. It was all over in seconds. With two of them, it was really quite easy. Ramsey did not know what hit him.

His struggle was in vain. They had him face down. His wrists tied to the iron bedstead. He kicked and wriggled. He hollered.

“The neighbours!” Bob cried.

“Yes, of course.” The man pulled a silk handkerchief from his pocket. Ramsey nearly choked. “It is best if you do not resist.” The man’s voice was dry.

Sweat ran through Ramsey’s hair. The back of his shirt was damp. His temples pulsated. His face was crimson. The man looked across at Bob. His eyes gave the instruction. Together they reached under Ramsey’s body, unbuckled the nineteen-year-old’s belt and tugged his trousers and underwear to his knees.

“All the way,” it was a quiet command. Bob obeyed. He took Ramsey’s trousers and smart white shorts down to the boy’s feet. Avoiding flailing legs, he ripped them from his body. Contemptuously, he threw them onto the floor.

Another look from the man. It told Bob he was ready. Bob glanced toward the hand basin. “Perfect,” the man croaked. He reached forward and took down the razor strop. He weighed it in his hands. “A wonderful specimen.” He swished the heavy leather strap through the air, getting its measure.

“Hold his legs.”

Ramsey was pinned down. There was no escape. His hands bound by rope. His feet held tightly against the mattress. His naked backside exposed. The man could do anything he wished.

The first slash whipped into his buttocks with great speed and strength. Ramsey munched down on the silk handkerchief. His hips gyrated. It was a reflex action. Six cuts fell rapidly. Bang-bang-bang. His once creamy-white buttocks were scarlet, the outline of the razor strop clearly visible across his cheeks.

Ramsey chewed on to the silk handkerchief. He wouldn’t let himself down. He wouldn’t give the bastards the satisfaction. Years in approved school had made him stubborn. He had endured pains and humiliations. That was the curse of the pretty boy.

The man wheezed and gasped as he turned Ramsey’s buttocks and the backs of his legs from white, through fifty shades of pink, to a deep crimson. Exhausted, he dropped the razor strop to the floor. Bob, his own breathing quite calm, stood waiting for the signal. It came. It was no more than a flicker of the eyelids.

Bob moved forward, took the buckle of the man’s belt in his hand. It was undone in seconds. Trousers and underwear tumbled. Bob fell to his knees. He took an almighty deep breath, parted his lips, and made a perfect “O”. He took the throbbing cock in his mouth, gagging as the old man thrust his hips forward and back.

The man in the room below heard the scream of ecstasy.


Other stories you might like.

Dad’s despair

The office manager

The dope smoker


More stories from Charles Hamilton II are on the MMSA website


Charles Hamilton the Second