Six of the best school stories, book




In the latest free-to-download book of stories we venture behind the walls of the school. The swish of the rattan and the crack of the paddle resound. Pyjama bottoms are lowered. Men of all ages present their bottoms for chastisement. A prefect shows a new boy at school who is boss and we get an insight into the life of the author Charles Hamilton II. But which of the stories is inspired by a real incident in his life? You work it out.

This book runs for more than 17,000 words and like the other books in this series it can be downloaded as a PDF file and read on your computer, laptop or a variety of e-book readers.

Click on the link below:



Look out for more free-to-download books from Charles Hamilton II in 2017.

Another book you might enjoy



More stories from Charles Hamilton II are on the MMSA website


Charles Hamilton the Second

How ‘The Starbirds’ Got Their Break

The four musicians finished their audition and stood around awkwardly waiting for the verdict. Across the room their manager and a concert promoter were in animated conversation.

It was 1961 and it seemed every kid was in a band. Most of them were talentless and their members would soon drift off into the real word to join the post office or work in a factory.

The Starbirds were different. They had worked together for a couple of years. They had ambition. They had a spark and they knew it. It wasn’t easy to put your finger on it. They were a tight band, and yes they could actually play their instruments. They had started to write their own songs, which was something unheard of at the time. But, it wasn’t that, there was something more to it.

Joe Goldberg, their manager, had spotted it. That spark; and it tore at his heartstrings. Goldberg had no experience in the world of pop music, but he was a businessman. He sensed what the Starbirds had and he wanted some of it for himself.

Joe was fat, ugly, thirty – and homosexual. Homosexuals were very common in pop business management at the time. It was no coincidence that nearly every male pop star was fresh faced, clear eyed and had very kissable lips.

Joe sat with Jack Rosenberg, one of the country’s top promotors. If Joe could get his boys on Jack’s upcoming national tour, The Starbirds would be made. They would even get the record deal that had eluded them so far.

“Very nice boys. Very nice,” Jack dribbled a martini cocktail down his chin.

Joe smiled. That was a good start.

“They have good stage presence,” Jack continued.

Joe smiled some more. “Stage presence,” the promotor had said. Joe understood the code. Jack was hooked; just as he himself had been.

“I like the way they dress,” Jack was having trouble controlling his martini glass. “Very neat and tidy. Nice fitting suits.”


Joe beamed brightly. The suits had been his idea. Much classier than leather jackets and tee-shirts. Didn’t people know that James Dean was long since dead?

Jack drained what was left in his glass. “Would they be amenable?” he asked, not even slightly shamefaced.

Joe tried to conceal a shudder, but didn’t quite manage it. “Amenable.” That was another code word. In his short time in the pop world, he had discovered it was a nasty business. Vile at times.

But, if the Starbirds were to reach their ambition to be “topermost of the popermost” and become stars they might have to put out. The casting couch was everywhere.

Joe plastered on his best poker-player’s face. “You mean sleep with you??’’

“No ….” Jack gurned his face. It was a grotesque sight, his thick lips and pointed chin twisted and turned.

“Blow-job then?”

“No ….” Accompanied by an elaborate shrug of the shoulders and spreading of the hands.

Joe feared he might have to recite an entire menu of possibilities. But Jack got to the point.


“Spanking?” Joe had not expected that. “How do you mean?”

“Oh nothing vicious,” Jack replied as if his request was the most natural in the world. “Just across my knee. Something like that.”

Joe’s jaw dropped. He was being asked to pimp his boys. There was an awkward silence. Jack filled it. “Harry. Is that his name? He’s the boy I want.”

Harry? Joe had expected the concert promotor to choose Adam. Adam was the prettiest of the bunch; the one the girls headed for first. Joe was mightily relived it wasn’t Lenny. Lenny was probably the least pretty of the boys, but he had attitude. He was probably that spark that made the band something special. He was also the one that Joe dreamt of. Night after night. Joe was in this business because of Lenny. At least (for now) Lenny would be unsullied by the pop world’s excesses.

“Harry, not Adam?” Joe tried to make it sound like an ordinary conversation, like they were discussing which lad made the better cup of tea.

“Yes,” Jack was drawling again, even though he had long ago disposed of the martini glass. “Very boyish hips. Lovely bum.”

Harry was also the youngest of the band members. He had just turned eighteen. He just about still maintained an air of innocence.

“So, if Harry pleases you,” shame gripped Joe even as the words formed in his mouth, that he was about to make the offer, “If Harry does as you ask, you will sign the band up for the concert tour?”

Jack did that gurning thing again; twisting and turning his mouth and jaw. The shoulders and hands went as well. He had thought he would give The Starbirds a place on the first concert, not the whole tour.

Joe read the hesitation well. “It’s the whole tour or nothing.”

More gurning from Jack. His cock was already on the march at the thought of that delicious boy in the tight suit trousers. Those hips. That bum. The cute innocent smile he wore. “My brother. It’s a deal.” Then the band manager and the concert promotor shook hands.

Ten minutes later Joe was with the band. Now, he had to sell the idea to them. He got right down to it. He had to. Jack Rosenberg was already waiting in his hotel suite, pacing up and down.

“Fooking fairy!” Lenny blurted, stabbing a dagger into Joe’s heart.

“You cannot be serious,” Adam shook his head in disbelief.

Harry’s face lit bright red, like a traffic light. His heart pounded. He couldn’t quite catch his breath. A spanking. Go over the old man’s knees for a smacked bottom. He couldn’t believe it either.

“No way. Tell him to fook off,” Lenny was in full stream and when he was in this mood nobody could get a word in.

The noise of Lenny’s ranting seemed far off to Harry. His own confused thoughts blocked out the words of his bandmate. A spanking. From an older man.

Harry had never told a living soul; he hardly wanted to acknowledge it himself. What would people think? What would they say? What would they do? They’d say he was a fairy.

Ever since he could remember Harry had dreamt of being spanked by older men. It wasn’t always over-the-knee. Only the previous day he had pleasured himself by imagining himself at the headmaster’s study, bent over an armchair while an old man wearing an academic gown and a mortar board slashed six-of-the-best cuts with a whippy curve-handled rattan cane into his stretched bottom.

But, never, ever, had he dared imagine that he could be – he would be – spanked for real. Even as his bandmates dismissed the idea out of hand, Harry’s cock stirred. Harry was not an educated lad, he had left school at fifteen, the earliest age possible. He was not good with words. Not like Lenny and Adam. He couldn’t explain the how or the why of it. He just knew. He wanted it. He wanted to be spanked by Jack Rosenberg.

“I’ll do it.” It came out louder and more determined than Harry had wanted. Four pairs of eyes bore into him. Even Lenny shut up. There was silence for five seconds then two bandmates spoke at once. In total agreement. No. Don’t do it.

“If it’s true we will get the whole tour, I’ll do it,’’ Harry could not look his friends in the eyes, too scared they would read his mind. Terrified they would find out he wanted to do this.

“It’s the only way we’ll get on the tour. We’d be made,” Harry said. “We’ve got to do it.”

“No,” Adam blurted. “No!”

“Shut up Adam, if he doesn’t mind doing it. Let him.” Lenny was the most ambitious of the group and the most hypocritical. Harry was right. The band would be made. Lenny didn’t mind what humiliation Harry would have to endure. Let him take one (or six, or whatever) for the team.

Lenny had spoken. That was the end of the discussion.

Twenty minutes Harry and his manager Joe were at Jack’s hotel suite. Jack and Joe exchanged glances. No words were spoken, but the message was clear. “I have delivered on my side of the bargain. You stick to yours.”

“Welcome my boy, welcome,” Jack drawled, taking Harry gently by the elbow and leading him into the lounge. Joe followed them in. Jack stopped, released the teenager, and swivelled on his fat legs. His look said it all.

“I’ll wait downstairs in the bar, shall I?” Joe didn’t wait for a reply.

Alone at last. Jack wasn’t one for foreplay. He liked to get down to action. Swift. Decisive. That’s how he had built one of Europe’s biggest entertainment companies.

“Stand there.” Jack pointed to a spot in the middle of the room. Harry’s heart raced; he could hear a pulse thumping in his ears. Unsteady on his feet, he shuffled into place.

“Tell me all the naughty things you have done. Tell me why I should spank you?”

Harry stood rooted. Startled. He hadn’t expected this. Naughty things? Like what? Jesus, he thought, he won’t spank me unless I’ve been naughty.

“Smoking. I’ve been smoking.” It was the first thing that came into his head.

“What, wacky-baccy?”

Harry blushed. He was a boy from the provinces. Marijuana was unheard of in his neck of the woods.

“No,” he sounded too apologetic, “Cigarettes.”

The old man was not impressed. “What else. Tell me more.”

“Drinking. I got drunk last night.”

Better, Jack thought. But still not good enough. There was one confession he really wanted to hear. He wouldn’t believe the eighteen-year-old standing before him did not commit this sin.

Harry stood dumbfounded. Silent. Embarrassed. Inarticulate.

“Do you play with yourself, young man,” the old man would have to force it out of the boy.

Harry coughed, blushed a fiercer red, and whispered, “Yes, sir.”

At last. Jack Rosenberg was ready to go. “You know what happens to dirty little boys who play with themselves?” It was a rhetorical question, so Jack answered it himself, “They get taken across my knee and have their bottoms spanked.”

Jack looked at the delicious boy standing in front of him, humiliation written across his face.

“Take off your jacket. Put it on the table over there.”

Harry’s fingers fumbled with the two buttons on his designer-suit jacket. He wanted this to happen. So much. The compilation of all his dreams. His brain told him he wanted it, but he couldn’t get his body to agree. At last the buttons were undone. He slipped the jacket off his shoulders and dropped it on the table.

Jack Rosenberg sat in the middle of a large leather couch. His fat legs spread. Somewhere under folds of trouser material his cock stirred.

“Stand in front of me.”

Harry did so. Rosenberg had never seen anything quite like it. He had spanked countless young men in similar circumstances. It was a perk of the job. None quite matched Harry. He was five-eight tall and as thin as a rake. His pale grey trousers had been especially-tailored for him. They hung from his hips without the aid of a belt. His buttocks were flat; so many young men had bums that jutted out. The trousers barely touched the boy’s mounds, emphasising the curves. It was a terrifically spankable bum.

“Come. Bend across my knee.” Rosenberg intoned. But, rather than allowing Harry to take up his own position, Rosenberg gripped him by the arm and tugged him forward so that the eighteen-year-old fell with some force, face down across his lap.  Harry pushed his arms forward to break his fall and rested his palms on the plush deep-pile carpet. His legs stretched behind him and bent slightly at the knee. In that way, his pointed toed shoes hovered an inch or so above the ground.

Harry’s bottom rested at an angle over Rosenberg’s right knee. The old man shuffled slightly; he didn’t want his stiff cock sticking into the boy’s body. Harry stared down at the beige carpet. This was a new experience in many ways. In his dreams he had always seen himself from a distance; bent over a chair or the knees of an old man. Then he witnessed the spanking as an interested observer. He had never imagined what it would look like from the spanker’s point of view; face down, witnessing nothing.

Nor, had he thought about how much a spanking would hurt.

He felt the palm of Rosenberg’s right hand gently caress his buttocks. He moved it in a circular motion, exploring the contours of Harry’s flat bum. Rosenberg enjoyed the smooth texture of the cool, thin material against his rough hand – the trousers were almost certainly mohair.

Rosenberg’s heart thumped against his chest. If he didn’t get a move on he might fall down dead with a stroke. He caressed the back of Harry’s thighs, then made another circuit of each cheek before raising his hand and smacking it down in the very centre of the boy’s right buttock. Then he struck the left. Soon he had a rhythm going that would make any of bongo player proud.

Of course, with his trousers and underpants on, Harry hardly felt a thing. He lay there submissively as the old man spanked on and on. The boy felt the hand connect time after time with his bony bum. What was he expected to do? Did Rosenberg want him to holler and scream as if he were being murdered? Was that part of the deal?

Abruptly, the spanking stopped. “Get up.” It was a curt command. Harry eased himself off the old man’s legs. Was that it? Was the spanking over? Suddenly, Harry felt cheated. This wasn’t how he imagined a spanking to be.

Rosenberg gripped the waistband of Harry’s trousers. In a move, perfected over many years, Rosenberg had the button undone and the zipper lowered. The trousers slid down Harry’s slender legs. Suddenly, he was back over the knee with his face in the thick carpet once more.

Rosenberg smoothed down the thin white cotton of Harry’s underpants so they fitted like a second skin. The cotton dug into the teenager’s crack, lifting and separating each cheek. It was a perfect target and Rosenberg lost no time smacking the palm of his hand across the tight arse.

This time it hurt. The old man found reserves of strength. Bang-bang-bang. His rough hand was as hard as any bedroom slipper might be. Harry gasped as the ache in his bum increased. Soon it increased to a warm glow. Up and down, up and down. Rosenberg’s hand spanked into the seat of the thin white cotton pants. Harry settled down, absorbing the new pain that each successive slap delivered. He loved the feeling of submission. He lay there head low bottom high, giving the older man full control of his smarting bottom.

Harry felt a movement in the old man’s body. He stopped spanking, turned slightly and took hold of the waist of the underpants. Without warning he tugged them down, over the curves of the boy’s bum until they bunched up at his thighs.

Rosenberg was rewarded with a wonderful sight. The whole of Harry’s bottom was a dark pink. From Rosenberg’s vantage point it looked very sore indeed. Maybe it was, but Rosenberg had not finished yet. He raised his hand and slapped it down a dozen times in rapid fire. He was delighted to see the imprint of his hand reproduced over and over across Harry’s naked bottom.

Harry opened and closed his mouth to absorb the pain. He let out silent “ouches” as once again the old man warmed up his backside.

Harder and harder came the blows. The throbbing in Harry’s bottom increased. He wriggled and turned; first to the left; then to the right. He kicked his legs. He tried to reach back with his right hand to intercept the blows. Nothing worked. He was pinned across the old man’s legs. There was no escaping. He would have to submit to this terrific bare-bottomed spanking. It would be over when Rosenberg said it was over.

Blood rushed though Harry’s body. His face was as scarlet as his bottom. His heart pounded. On and on Rosenberg spanked. The pain was intense. Harry wriggled against Rosenberg’s thighs. Then he felt the bulge under the old man’s trousers stick into his own body. Harry’s cock throbbed its own greeting. Still Rosenberg spanked on and on. As his hand rose and fell he thrust his rigid cock into the boy’s torso.

“Haaaaaaah!” It sounded like Rosenberg had been shot. It seemed like a tremendous cry of pain. The front of his trousers was soaked.

He let go of Harry who immediately jumped off the man’s lap. His own cock pointed at the sky. It was a massive, stiff erection; the kind only eighteen-year-old men can sport. Harry hopped from one foot to the other, his trousers and pants at his feet; his six-inch stiff cock swinging up and down.

Rosenberg’s eyes were as wide as saucers. Never before had he seen an uncut specimen. He shuffled off the couch; his knees sank into the plush carpet. He reached out; put his arms around Harry, gripped the teenager around the arse, and pulled him forward. Harry let him take the cock in his mouth. He gorged himself.

Rosenberg bobbed downwards until he had the teenager’s entire shaft in his mouth and throat, his lips squeezed tightly around the base of the cock. Harry groaned as the old man slowly moved up and down, his lips and tongue constantly working upon the whole length of the swollen organ.

Harry’s inexperience showed. Before ten seconds had passed, Harry’s cock throbbed and spurt after spurt of sticky cum pumped into Rosenberg’s hungry mouth.

Rosenberg lay on the carpet, gasping. Choking like a beached whale.


Three years later, The Starbirds’ plane landed in New York. Ten thousand screaming girls were there to greet them. The band already had a string of hit records in Britain. Now, they were about to conquer America. They became the biggest thing in pop music history. Now, more than fifty years after Harry and Rosenberg met at the hotel suite, the band are still touring the world filling arenas.

But, nobody ever talked about the night that it all began. Until now …

Other stories you might like

A memorable night at the theatre

My friend Justin

The smiling boy

More stories from Charles Hamilton II are on the MMSA website


Charles Hamilton the Second

The Post Office Thief

Mr Sedgemore pulled his threadbare overcoat tighter around his body as he battled headlong into the wind. A light drizzle was falling and soon his feet would be wet. Unsteadily, he crossed the glistening cobbled street. He would soon be home. His wife would have collected their pensions so they might have the gas fire on for an hour this afternoon.

He unlocked the door of his small terraced house and paused. Something was not right. He could hear voices coming from the kitchen. They never had visitors, except sometimes when that young vicar came to spy. On the ground near the door against the wall was a backpack. What was going on?

He hung his overcoat on a hook and still wearing his jacket, he walked into the kitchen. At the table tucking into a plate of egg and chips was a scruffy young man. The man looked up and while chewing on a mouthful of potato he nodded a greeting. Mr Sedgemore didn’t like young people. They hung around bus stops at night drinking cheap cider and writing rude things on walls. This one looked like he hadn’t had a wash in days.

“Hello Albert,” his wife busied herself fetching a cup and saucer and pouring tea. He gestured with his head and his wife followed him out of the kitchen into the front room.

“Who the hell is that?” Mr Sedgemore rolled his eyes exasperated.

“That’s Geoffrey.”

“Where’s he from?”

“He doesn’t have anywhere to live. I said he could stay here.”

“Elsie!” Mr Sedgemore knew what this was about. She missed their sons. Both were grown up and had long since flown the coup. Richard was at the other end of the world in New Zealand. Mr Sedgemore doubted is he would ever see his son and his family again. Tony lived somewhere in London; they had not heard from him in a while. It was probably just as well, Mr Sedgemore thought. Tony was a bit limp-wristed. He never fitted in at home. He was better off out of it. God only knew what kind of life he was living. At least, Mr Sedgemore comforted himself, it was legal these days.

He knew his wife was lonely; she would see Geoffrey as a companion. Why didn’t they just get a stray dog?

“Where did you find him?”

“In the post office. He tried to steal the charity collection box.”

Mr Sedgemore’s face flushed. His mouth opened and closed like a goldfish. No words came. He was literally speechless, but the expression on his face spoke for him. “A thief! You’ve brought a thief into our house!”

Mrs Sedgemore answered her husband’s unasked question. “He isn’t really a thief. He was hungry. He needed money for food.”

“He is a thief, for crying out loud. Did you call the police?”

“No the people at the post office let him go. He looked so sad.”

“Ye Gods, Elsie, he’s really taken you in.” Suddenly, Mr Sedgemore was taken back thirty years or more to the time his son Richard had been caught stealing from the corner shop. Mr Sedgemore still had the whippy rattan cane upstairs on top of the wardrobe.

Elsie ignored her husband and returned to the kitchen leaving the old man gasping in outrage. From a distance he heard his wife’s voice. “Go upstairs and take a bath Geoffrey. Give me your dirty clothes and I’ll take them to the launderette later.”

An hour later Mr Sedgemore was still sitting in his chair, enveloped in defeat. There was no arguing with his wife. He loved her dearly even after suffering a lifetime of her whims. But this time was too much. How could they trust this thief? Wouldn’t he wait his chance and clear them out. What if he were a drug addict?

Then he had an idea. It was simplicity itself. The young man wouldn’t want to stay. Not when he learned what Mr Sedgemore had in store.

He went to the bottom of the stairs. “Geoffrey come down here please!” Immediately a bedroom door opened and the young man appeared. He had washed and shaved and changed into clean clothes. Suddenly, he didn’t seem so threatening.

“Go into the front room, Geoffrey.”

Obediently, the young man padded down the stairs and entered the room. He stood awkwardly, not sure if he was allowed to sit.

Mr Sedgemore had rehearsed the words in his head. Not looking at the young man before him he launched into his speech. “You are a thief. I do not want a thief in my house. However, Mrs Sedgemore has it in her head that you should stay. Well so be it. But you are still a thief and you shouldn’t get away with it.” The words come in a rush. Mr Sedgemore paused, looked at Geoffrey and concluded, “You should be punished. If they won’t call the police, I’ll punish you myself.”

Geoffrey watched impassively as Mr Sedgemore crossed the room to a sideboard, opened a drawer, looked in and withdrew a large wooden clothes brush. He turned and without uttering a word, he waved it at Geoffrey.

The young man blanched. He ran his hand through his hair. The silence was killing him. “You want to spank me? I’m twenty, I’m too old to spank.”

“My house, my rules. And if you are to stay here, you’ll have to get a job and pay your way. We can’t afford passengers. Not on our pensions.” Mr Sedgemore paused and gave a half smile. That should do it, he told himself. A spanking and he’d have to get a job. He was probably bone idle. Weren’t all young people? That was probably why he was on the streets in the first place. He wouldn’t want to stay now.

Geoffrey stared at the old man before him. He wanted to spank him? Perhaps he was kinky. He’d seen a few odd balls when he had been sleeping in a shop doorway on the High Street. Men who offered him money if he would lick their dicks for them.

“Go and pack your things. You should leave before Mrs Sedgemore gets back.”

Geoffrey eyed the clothes brush in the old man’s hand. It looked pretty solid, but Mr Sedgemore was old and weak. It couldn’t do him much damage. It would be a bit embarrassing, but nothing like having a throbbing cock in your mouth.

“Alright,” he whispered.

Mr Sedgemore craned his neck towards Geoffrey. “What, what did you say?”

“I said, ‘Alright.’ I’ll let you spank me.”

“Let me!” Mr Sedgemore raged. “Let me! Don’t think I take any pleasure in this young man. You are a thief. You deserve to be punished.” Mr Sedgemore’s blood pressure was rising. He needed to be careful at his age. “I am doing a public service,” he trailed off, realising how pompous that sounded.

He pulled a chair into the middle of the room and sat down. “C’mon, take down your jeans, get across my knee.”

Geoffrey’s mouth opened and closed. His face flushed.

“You won’t feel a thing on those jeans. Get on with it. Mrs Sedgemore will be back soon.”

Geoffrey stared down at the old man’s bony knees. Could this really be happening to him? He closed his eyes. He had to go through with it. What choice did he have? A spanking across Mr Sedgemore’s knee, followed by a warm roof over his head or cold days and nights on the streets sucking cock for his dinner?

He opened his eyes, unfastened his belt, popped the rivet at the top of his jeans, gripped the tab of the zipper and pulled. The front of his jeans fell open and with no effort at all he had them at his knees. He took a deep breath and lowered himself into position. He was a tall boy and Mr Sedgemore short. It was hardly a perfect fit. Geoffrey reached his hands forward and pressed his palms into the garish carpet. Behind him he bent his knees and rested his stomach on Mr Sedgemore’s thigh so that his bottom was raised to receive the brush.

Mr Sedgemore wasted no time. He pulled Geoffrey’s shirt away from the target area. The brush rose and fell in rapid succession paddling every square inch of the young man’s bum. Geoffrey wriggled this way and that, but the pressure of Mr Sedgemore’s hand in the middle of his back kept him more or less in position.

Scolding as he spanked, the old man took great delight in walloping the exact same spot two or three times in succession, making Geoffrey wince and then howl. His cries increased as the heavy brush stung his upper thighs with a vengeance. His legs kicked vainly, but they were stopped by his jeans snagged around his knees.

Geoffrey wasn’t sure how many licks Mr Sedgemore gave him; it could have been a hundred, it seemed to go on forever. All of the sudden, it ended and Mr Sedgemore released his grip. Geoffrey’s hands shot to cover his behind and he performed the traditional “spanking dance” hopping from one foot to the other and then standing on tip-toes with both hands plastered to his cotton-covered cheeks as he tried to rub out some of the sting, while the old man lectured him about his behavior and promised that if there was a next time, there was a whippy school cane upstairs ready to attack his bare arse.

He pulled up his jeans and stood uncertain. What happened next? He glared at Mr Sedgemore. The old man had hurt and humiliated him and threatened to do it again whenever he wanted. For two pins he’d smash the old git’s face in.

Suddenly, the front door opened. Mrs Sedgemore looked into the room. “Oh good,” she smiled, “You’re making friends.”



Other stories you might like

The troublesome lodger

Foreign language student

The dope smoker


More stories from Charles Hamilton II are on the MMSA website

Charles Hamilton the Second

Troublesome teens. Never too old for a spanking, book


They might think they are adults, but older teens are not. They are still children and they need to act like it. They should respect their parents and obey adults. Without question. And if they don’t? These stories will remind them of the consequences of bad behaviour. A very sore backside indeed.


The pain was intense, but there was no escaping it. He struggled to the left and right but the grip on his neck was too powerful. He was at the mercy of his father: but the irate man was not showing any. In one last desperate attempt to free himself, Aaron kicked out his left leg and caught his father a blow on the shin. Rather than dissuading the older man from his mission to toast his son’s buttocks it spurred him on.

– Extract from Put back in short trousers


The book runs for more than 16,000 words and can be downloaded by clicking the link below. The PDF file can be read on computers, laptops and a variety of e-book readers.



Another free-to-download book you might enjoy




More stories from Charles Hamilton II are on the MMSA website


Charles Hamilton the Second

Missed Opportunities

Richard stood by his bedroom door listening. Any moment now the front door would close and he would be alone in the house.

He could hear his mother bustling in the kitchen. “Come on, come on,” he was impatient to get on with it.

At last, the front door clicked into place. The eighteen-year-old dashed to the bedroom window in time to see his mother hurry down the road. She would be at work all day.

The boy pulled a straight-back wooden chair that was resting against the wall. It was his favourite chair. Often, he fantasised about that chair. But not now. This time it had a practical purpose. He moved it close to the wardrobe, stepped up on it, extended himself on tip-toes and reached for the John Lewis bag he had hidden on top.

The chair wobbled a little, but Richard steadied himself. Within moments he was safely on the ground.

He reached inside the wardrobe; grabbed his school blazer and tie and hurried out of the room. Seconds later he stood excitedly in the hallway, in front of the full-length mirror. He had been waiting a long time for this.

Richard was not a typical eighteen-year-old. He was about five-feet-seven tall and a little on the thin side. His mother always said he could do with “fattening up”. His tousled fair hair needed cutting and his face was scarred with acne.

He put the plastic bag by his feet and pulled on the blazer. It was an ordinary black school blazer. If it wasn’t for the school crest on the pocket it would be just like the blazers worn by tens (possibly hundreds) of thousands of schoolboys up and down the land.

He pulled up the collar of his white shirt and wrapped his school tie around his neck. He did the top button of the collar up and pulled the tie tight. He never wore it like this at school, but soon he would be visiting the headmaster: he needed to look neat and tidy.

Satisfied, he clasped the buckle of his wide leather belt and unfastened it. His jeans were cut loosely and the weight of the belt made them slide over his hips. Without unfastening the buttons, Richard tugged the blue denims to his feet and stepped out of them.

He paused to admire himself in the mirror. His white Y-fronts hugged his body slightly and contrasted against his hairless sun-tanned legs.

His heart raced. He bent down for the plastic bag, reached inside and extracted a brand new pair of school short trousers. They were beautiful; the real deal. Dark grey with sharp creases down the front and back. He stepped into them and pulled them up. The half-elasticated waist ensured a snug fit.

It said on the label they would fit “15 years”. Which school made fifteen-year-old pupils wear short trousers? Richard wished it were his.

It had taken him all his courage to buy the short trousers at the John Lewis store. Surely, the sales assistant would think him odd. But she didn’t bat an eyelid. She hardly noticed he was there. Perhaps there really were lots of fifteen-year-olds in short trousers that he never knew about.

His cock stiffened as he admired himself in the mirror. The short trousers were perfect; they fell to just an inch above his knees.

His outfit was almost complete. He delved back into the bag and took out a pair of grey knee socks, with red bands at the top. He sat down on the stairs and pulled them on. Then he laced up his shiny black shoes. He was ready.


He returned to the mirror, turned his back to it and bent down and touched his toes. He was ready for his six-of-the-best.

Richard had fantasied about corporal punishment for as long as he could remember. His favourite was making a trip to the headmaster’s study. In his imagination it was always some elite public school, where the boys boarded. He knocked on the door of the headmaster’s study, waited for the call from within, turned the handle, and pushed it ajar.

“Come in Rodgers,” the headmaster barked.

It was a huge study. The headmaster, resplendent in his flowing academic gown, stood in the centre of the room. To one side was an old, rather battered, desk that dated back at least a hundred years.

Dr Vigar didn’t stand on ceremony when it came to dishing out corporal punishment. A boy on the receiving end had to stand on his own two feet. Literally. Or to put it another way, the boy about to get a beating had to stand, bend over touch his toes and he had better not jump about as the cane cut his backside or there would be Hell to pay.

Richard entered the study. In fact, the headmaster’s desk wasn’t the first thing he saw as he went in. Behind the desk was a hat stand, six feet tall at least, and hanging from the top were six punishment canes of various sizes and thicknesses, all dangling by their crook handles.

Dr Vigar spoke clearly and decisively. “Stand there,” he indicated a spot on the rug that covered bare, polished floorboards. The headmaster already had his weapon of choice in his hand. “Face that way,” he used the stick to indicate the far wall.

“Bend over, touch your toes.”

Richard ran every moment through his mind; dozens and dozens of times; night after night.

He was wearing a posh green-and-gold blazer and grey short trousers. Dr Vigar, a fifty-something, swished his cane, touched it against the boys left buttock, took aim, drew his arm back to above shoulder height and let fly.

Richard saw his own smooth hands extended as they stretched out so the tips of his fingers touched the toes of his shoes. They were plain black shoes, of course. Highly polished: polished every night, whether they needed to be or not.

Richard also saw his grey socks, with green-and-yellow tops pulled up as tight as they could go. Woe betides a boy who wore his socks in any other way. The socks went to just below the knee and between them and his short trousers was an area of cold white flesh, maybe two inches between socks and shorts.

And, dangling in front of his face as he struggled to keep in position hung his school tie. A narrow specimen with large diagonal stripes: alternate, one green, one yellow.

Richard lingered on every detail. “Bend over, touch your toes,” the head had commanded. In one continuous moment he was over, fingers touching toes.  WHACK! WHACK! WHACK! WHACK! WHACK! WHACK!

“Stand up, send in the next boy.” And that was it. No ceremony really, just a simple ritual, familiar to generations of schoolboys. In, out, and a searing pain in the bum at the end of it. And a stiff, aching cock.

Richard looked back at his reflection in the mirror. He had a nice bum; the grey short trousers showed it to great effect. He parted his legs to get a better view.

Richard had never been caned in his life and was never likely to be. They didn’t use corporal punishment at his comprehensive school. Nothing. No canes, no slippers, belts or tawses. Not like Albury Grammar where his younger brother Anthony went.

Albury was a traditional school. And that included traditional discipline: the cane. Lots of boys were caned at Anthony’s school. Once, Richard remembered there had been some kind of clampdown on smokers. One playtime the prefects had rounded up about a dozen kids who had sneaked behind the gym to light up.

Wasn’t that wonderful, Richard thought. All you had to do to get the cane at Albury was to smoke a cigarette. Wow, he would be a twenty-a-day man. Who cared about cancer?

A rattling at the letter box of the front door startled him away from his memories. Richard saw the outline of the postman in the opaque glass. Unsure whether the postman could see him, Richard dashed into the living room and waited for the coast to clear.

The postman’s next call was three houses along. There he momentarily disturbed Mr Alan Tuckworth, a thirty-five-year-old bachelor.

Alan too stood in his hallway in front of the mirror. He had no new outfit; he was very satisfied with his ageing and rather tatty academic gown. It hung loosely from his shoulders and covered his tweed jacket and most of his worn black-and-white-striped trousers. He rather liked the authentic schoolmaster’s mortar board that lay askew on his head. The tassel that dangled from one corner was especially pleasing. He looked exactly like the schoolmasters in the old boys’ storybooks he collected.

In his hand he thoughtfully flexed a thick, but whippy, crook-handled cane. It was quite easy to get the four-feet of rattan to form a bow. It was dark yellow and had notches every three or four inches along its length.

He swished the cane through empty air. In his imagination he was Dr Tuckworth of St Eiseldown public school. In front of him was a sixth-form troublemaker.

“You again.” He spoke out loud, for he lived alone. He flexed the cane once more, eyeing up the eighteen-year-old in front of him.

“Well you were beaten before. Six on the seat of the bags.” He swished the cane, admiring the swooshing sound it made. “It obviously was not enough.”

Another swish of the cane.

“So this time you will be caned on your underpants.”

Tuckworth’s imagination was in full flow.

Swish! Swish!

“Take your trousers down, bend over and touch your toes, Rodgers.”

In his mind’s eye, his eighteen-year-old neighbour, reached for his belt buckle …

Other stories you might like

First day of term

Late home from school

The fire-raiser




More stories from Charles Hamilton II are on the MMSA website


Charles Hamilton the Second

Visit to Uncle Roy



Roy Denning was very “old school” and “school” was the appropriate word, because he kept three authentic swishy rattan school canes in a drawer in the kitchen and he wasn’t afraid to use them.

He knew they were authentic because they had the words “Birmingham Education” inscribed on them near the curved handle. A schoolmaster pal of his had taken a bunch of canes from school when he retired. He gave them away to fathers he knew who would put them to proper use.

Roy sat in his kitchen, watching the clock. Soon, very soon, one of those canes would see some action.

Across the city, John, Roy’s nineteen-year-old nephew, trudged through the damp streets on his way to the bus stop. It was not easy to get to Uncle Roy’s by bus. Routes didn’t go across town. You had to get one bus into the city centre and then another out again. The journey would take at least forty minutes, that was plenty of time for him to contemplate his fate.

He wore his thickest and newest jeans, but it would do him no good. He knew his uncle’s reputation. He had been quite close to the man’s sons. The two eldest had long ago fled the nest leaving only twenty-year-old Bert behind, trapped by his lack of education and poverty.

John had left school four years previously and had a steady job as a corporation bin man. But, he had been caught stealing records from a department store. The police gave him a slap on the wrist but he knew he would get much worse from Uncle Roy. He could have afforded to pay for the record, but stealing from shops had become a pastime. He and a few of his mates would see what they could get away with. They dared one another. If they got caught – which wasn’t often – the police didn’t do much. They had bigger fish to fry. John’s friends didn’t feel like they had been punished. But, they didn’t have an Uncle Roy.

His mum was distraught when she found out. The shame he had brought on the family. His poor dead father would be spinning in his grave. She would have thrown him out of the house, but she couldn’t. She needed the money he brought in each week. Her pay as a char woman couldn’t keep a roof over her head and food on the table.

It had stopped raining by the time John arrived at Uncle’s Roy’s terraced house. The cobbles on the street were wet and he had to shuffle along to avoid slipping. John had been there before, but each time he visited the dankness of the place annoyed him. The houses were old and decaying. Soon, like the other slums in the city they would be bulldozed and tower blocks built in their place.

It couldn’t happen too soon for John. Who, he wondered, wanted to live in a house with an outside toilet and no bathroom? His uncle had to wash in a tin bath or else go to the municipal bathhouse.

John knocked cautiously on the door. He knew his uncle was at home. He had been summoned by him. There was no doubt his uncle was waiting for him and no doubt what would happen once he got inside the house.

Uncle Roy was a robust man, larger than life, some would say. He had huge hands and big feet. His head was as round as a football and his ruddy face made him look permanently drunk.

“Come in John,” it wasn’t an unfriendly greeting. “Go into the kitchen.”

Uncle Roy followed his nephew down the passageway. They stood awkwardly in the kitchen. It was surprisingly large for so small a house. As always a stink of cabbage water, distemper and mould hung in the air.

John knew why he was here, in this particular room. It was where Uncle Roy kept his school canes. In a drawer in the rickety wooden table.

Uncle Roy spoke first. There wasn’t much to be said. It had all been said at John’s house. His mum had told Uncle Roy about the stealing. Uncle Roy hit the roof. There was much cursing. Then, when tempers had cooled, the sentence was pronounced. “My house Saturday afternoon. Be there or else.” Uncle Roy didn’t explain the, “or else.” What, John wondered, could be worse than what Uncle Roy had in store for him?

John stared at the linoleum beneath its feet. It had once been coloured blue but decades of shuffling feet had reduced it to a worn grey. His cousin Bert appeared at the kitchen door, keen to see the fun.

“Bugger off, Bert,” Uncle Roy frowned. “Go get me a paper. Take your time.”

Bert did not hide his disappointment. He sat on the stairs, put on his outdoor shoes, and then moodily opened the front door.

Uncle Roy pulled open the ramshackle drawer of the table. It took both hands because it kept sticking. He reached inside and pulled out a cane. There were three but he didn’t have to choose; they were all the same length and thickness.

John’s eyes followed his Uncle’s movements as first he swished it through the air and seemingly satisfied with that, he then tested its flexibility in his hands. It was a standard “senior” cane. Similar ones had peppered the backsides of older schoolboys since time immemorial.

“Let’s get on with this shall we?” It was an instruction disguised as a question. John gulped loudly. He had never been caned before; nor even spanked. It wasn’t that he was a goody-doody, since clearly he was not. It was just that no one had been around to give him a good hiding when he deserved it.

“Jeans and pants down. Bend over the table.”

John had expected this, but still his body would not obey his brain. He stumbled with his belt buckle for so long an exasperated Uncle Roy cried, “Do you want me to do it for you?”

No! It was bad enough stripping half naked but the humiliation of having his uncle take down John’s trousers and pants was too much. He got his fingers to obey and soon his jeans and underpants were resting on top of his blue-and-black bumper boots.

He shielded his cock and balls with his hands. Uncle Roy smiled, but said nothing. He swished the cane and then tapped it on the table top. “Bend over.”

John leaned forward, stretched out his arms, arched his back and gripped the table’s edge.

“Not like that,” his uncle was becoming exasperated. “Lay flat down on your stomach.”

John glanced down at the dirty stained oil cloth that covered the table. It looked disgusting. Nonetheless he eased himself forward and rested his chest on the table. His stomach pressed against the edge of the table.

“Raise your bottom higher. Stretch those arms out. Hold on to the edge of the table,” Uncle Roy ordered. “That’s right,” he added, after his nephew had shuffled himself into the correct position.

Johns forehead and nose pressed into the filthy oil cloth. It felt sticky. The smell of stale cooking fat almost made him gag. He stared down onto unidentified stains.

A cold breeze brushed across his naked haunches. The kitchen window was open. What neither he nor Uncle Roy saw was Bert standing on the dustbin in the small backyard. From his unstable vantage point he had a perfect view of his nineteen-year-old cousin stretched out across the table, his jeans and pants at his feet, his naked buttocks twitching slightly as they waited for the onslaught from the cane to begin.

It wasn’t long in starting. “Brace yourself,” Uncle Roy ordered. It wasn’t much of a warning. John had no time to clench his buttocks tight before the sound of the cane whooshing through the air was followed by a loud crack as it sank into meaty flesh. John’s howl could be heard in the house next door; due to the combination of paper thin walls and one lusty screech from the injured teenager.

He marched his feet up and down, trying to stem the tide of pain that started at his now-scarred bottom and travelled up and down his legs. He gripped the table’s edge tightly, waiting for slash number two. Uncle Roy was very satisfied with the deep red line that had immediately appeared across the centre of both of his nephew’s buttocks. It had been a year or so since he had last put a cane across Bert’s backside, but he could see he had lost none of his touch.

Swish! Number two bounced off the under-curves of the cheeks and was greeted by renewed marching. John stuck his hand across his mouth to stifle the yell he wanted to make.

Outside, in the yard, Mr Drury, the next door neighbour was intrigued. “What are you doing standing on that bin, Bert?”

Bert opened his mouth to reply just as the sound of a cane’s swish and a teenager’s yell poured out of the kitchen window.

“Oh, I see,” Mr Drury laughed, “Your dad’s giving someone what for.”

“Yes, my cousin,” Bert replied.

“Here move over, let me have a look.”

He climbed up next to Bert in time to see the cane lash down for the fourth time into John’s buttocks. He was not close enough to notice that four deep lines now criss-crossed John’s naked bum. Most of his bottom glowed dark pink. Soon four purple welts would form.

John sucked on his own forearm to stop him crying out again as slice number five hit him high; on the top of his globes almost near his spine. The teenager’s breathing was heavy. The pain was beyond his endurance. His head and temples throbbed every bit as much as his savaged backside.

Outside, Mr Drury atop of the dustbin leaned forward for a better view. He saw the sixth and final cut bite deep into the very centre of John’s buttocks. It hit at an angle and crossed two previous cuts, reigniting the already considerable pain.

At that point John yelled blue murder and Mr Drury and Bert tumbled from the bin, with a resounding crash. The lid flew off and rolled down the yard.

“What the …” Uncle Roy cried out.

“I’m out of here,” Mr Drury turned on his heels and was in the safety of his own yard before Uncle Roy reached the kitchen window. All he saw was Bert stooping to pick up and replace the scattered rubbish in the bin.

Uncle Roy summed up the situation immediately. “Bert get in here, now!”

The twenty-year-old entered the kitchen in time to see his younger cousin still prostrate across the table. Tears were flowing freely down his face. He seemed to have great difficulty breathing and was gasping for air. His backside was raw. Bert knew from personal experience that John had endured one hell of a thrashing.

“Get up John, it’s over. Let that be an end to the matter, but if you get caught stealing again I’ll give you twice as many strokes and twice as hard.”

Gingerly, John rose from the table. His backside felt like it was on fire. He lightly touched the raw flesh with his fingertips and was shocked how hot his bottom was. Conscious that he was half naked in front of both his uncle and his cousin, he bent down and painfully pulled up, first his underpants and then his jeans.

“You!” Uncle Roy turned to his crestfallen son. He swished the cane menacingly. “What have I told you before about peeping through windows?” He didn’t wait for an answer. He pushed Bert down across the table.

John didn’t wait to see the spectacle. He was through the front door before the first swipe connected with the seat of Bert’s trousers. John shuffled along the cobbled street. It had dried and there was no danger of him slipping, but he shuffled nonetheless. Each successive step reignited the pain in his bottom as his underpants and jeans chaffed against the raw flesh.

He had two extremely uncomfortable bus rides home. He was relieved that neither conductor asked him why he was standing when so many seats were unoccupied.

Other stories you might like

Caning for England

Housemate pays the rent

Duncan and Uncle Henry



More stories from Charles Hamilton II are on the MMSA website

Charles Hamilton the Second

The Dean of Dorm Discipline book



The Dean of Dormitory Discipline regularly beat misbehaving students and there was never a weekend when his paddle did not fly through the air. This gave them ample opportunity to swap stories about their spankings and their bruises became badges of honour when displayed in the communal showers.

Now, Mitch must pay for his missed curfew …

The Dean of Dorm Discipline is one of six corporal punishment tales from universities that appears in the latest free-to-download book from Charles Hamilton II.

This one runs for more than 15,000 words and like the other books in this series it can be downloaded as a PDF file and read on your computer, laptop or a variety of e-book readers.

Click on the link below:



Another free-to-download book you might like




More stories from Charles Hamilton II are on the MMSA website


Charles Hamilton the Second