Caught reading stories

“Well, you’re one young man who needs his bottom smacked.” Colin heard his boss speaking before he realised Mr. Higginbottom was standing behind him, reading over his shoulder.

Colin blushed deeply. Caught red handed. He had thought everyone was at lunch. It was the only time of day he could go on the Internet privately. The dismal rooming house where he lived didn’t extend to wi-fi. Colin gulped, what would happen now? Even if he didn’t get fired, his guilty secret was out. Soon the whole office, the whole company even, would know he had been found downloading male-on-male spanking stories.

“Charles Hamilton II, I see.” Did Colin detect a hint of mirth in his boss’s voice? “Have you read the story where the boss takes the young office worker over his knee and spanks him with a hairbrush?”

Colin’s heart raced. Mr. Higginbottom, his staid fifty-something-year-old boss, was into spanking. Spanking men.

Mr. Higginbottom perched his buttocks on the edge of a desk. “I thought you might be into this sort of thing,” he said, a warm smile splitting his face. “I see the way you look at Adrian.”

Adrian was the office “gofer” – go for this, go for that. He had just finished school and was waiting to go to university. Often, he wore the pale grey trousers that once were part of his school uniform. Colin would stare at Adrian’s buttocks stretching the seat of his snug trousers when he bent down to open bottom drawers of filing cabinets. Many times Colin had pleasured himself at night in his grim room imagining he was a headmaster and Adrian was touching toes before him, his grey trousers and white underpants at his ankles, while Colin swished a whippy rattan cane across the teenager’s naked cheeks.

Colin could not meet his boss’s eye. Had the old man been spying on him? Did he dream of taking Colin across his knee and spanking his bare bottom, just like in the story he talked about?

“Well young man,” Mr. Higginbottom’s smiled hadn’t faded. “How do you think I should deal with this?”

Colin was twenty-four years old and had worked for Tillotson’s since he graduated from university. It was a good job with prospects and he would very much like to keep it. His heart raced. Suddenly, his mouth dried. Was this a trap? Was his boss secretly recording the conversation? Were his fellow workers hiding close by, waiting to jump out and humiliate him?

“What’s up, the cat got your tongue?” Mr. Higginbottom rose from the desk. “Well, I know what to do.” He walked to the door of the office and called over his shoulder as he exited, “Come to my house tonight. Six-thirty. Number twenty-two The Avenue. Don’t dare be late.”

He left Colin at his computer gaping, open mouthed. Was this for real? Things like this didn’t happen in real life. It sounded like a story from the spanking blogsite.

The Avenue was in a very plush suburb. It was mid-summer and still warm as Colin alighted from the bus and walked the hundred or so yards to Mr. Higginbottom’s house. Which one was his? They all looked the same. All had front porches and gardens, but nobody was out. He was certain he saw a curtain twitch at number eighteen; it could be the Neighbourhood Watch, keeping tabs on strangers.

The door at number twenty-two opened as Colin walked up the garden path. Mr. Higginbottom had been waiting. Ready. His boss still wore his office clothes, a heavy grey suit and waistcoat, not the best attire for a summer’s day.

“Come this way,” Colin followed as his boss crossed the hallway and opened a door to the lounge. “There’s someone I’d like you to meet.”

Colin stood in the threshold of the room dumbfounded. He was learning so much about Mr. Higginbottom today. Stood in a far corner with his hands on his head was a young man about Colin’s age. He wore a green blazer, grey short trousers and knee socks.


“Andrew has been an extremely naughty boy, haven’t you Andrew?”

Andrew remained silent, his nose pressed close to the wall.

“I do apologise Colin; Andrew is being a little sulky this evening.”

“Oh, eh, that’s all right,” Colin blustered. What was he supposed to say?

“Turn around Andrew, say ‘hello’ to our guest.”

Sullenly the young man swivelled on his feet. Colin’s heart raced. He recognised him immediately. He of all people in this situation. He would never have imagined it. It made him feel a little sad. Colin knew Andrew from university. He had never met him, not properly, but he had lusted after the boy for more than a year. He was called Andy in those days. He hadn’t changed much. He still had short fair hair and a clear complexion. His slight over-bite was really sexy. But, it was his arse that Colin remembered most. Andy used to wear blue jeans that hung from his hips and showed off his bum to perfection. Andy loved to play pool and Colin would spend hours in the University Students’ Union watching the Adonis bending across the table lining up his shots.

Colin regularly wanked himself dry at nights fantasising that he had that beautiful denim-covered bum across his knees.

“Hello,” Andrew pouted. Colin nodded his own greeting, a little disappointed that Andrew had not recognised him.

“Andrew is a grad student,” Mr. Higginbottom explained, “And he thinks he can skip the library and spend time at the beach rather than work on his dissertation, don’t you Andrew?”

Andrew’s scowl did not diminish.

“Well young man,” Mr. Higginbottom adopted the voice of a stage-headmaster, “We’ll see about that.” Then, turning to Colin, he said, “Please Colin, sit down.” Then he added ominously, “I’ll deal with you later.”

Mr. Higginbottom slipped off his jacket and laid it carefully on the dining table. Andrew’s eyes followed the man anxiously as he picked up a chair and set it down in the centre of the room. Then, he walked to the sideboard, opened a drawer and rummaged inside. Then, he opened a cupboard and did the same thing.

“Andrew, what have you done with the clothes brush?” he asked irritably.

The young man perfected an air of innocence, but remained silent.

“Andrew!” Mr. Higginbottom was losing patience.

“Doh! You think you can get out of a spanking that way young man. Well, you’ve got another think coming.” He stormed from the room. Andrew stood awkwardly. Who was this stranger and why had he been invited into the house to witness his spanking? He had no time to ask these questions as Mr. Higginbottom returned to the room. In his right fist he gripped a large, heavy bath brush. “Well, if I can’t use the clothes brush, I’ll just have to use this.” Colin detected a snarl around his boss’s lips as Mr. Higginbottom smacked the brush into his left palm. Colin had no personal experience to call upon, but he knew from the stories he loved to read that a heavy brush like this could leave a boy’s bum severely bruised.

“C’mon, let’s get on with this,” Mr. Higginbottom snarled as he sat down heavily on the straight-backed chair. He snapped his fingers to instruct Andrew to stand beside him. Dolefully, the young man shuffled into the required position.

“Trousers, pants down.”

Colin’s cock twitched as he watched the boy he had lusted over for so long, reach and unhook his elastic snake belt. Then, Andrew undid the metal clasp at the top of his trousers before taking the tab of his zipper and pulling. The grey short trousers tumbled down his legs, revealing a pair of gleaming white Y-front underpants. Colin was perfectly positioned for a terrific view as Andrew simultaneously pinched the cotton pants at the left and the right hip and with the merest flick of the wrists sent them south to join the trousers at his feet.

Colin hoped he hadn’t audibly gasped at the sight of Andrew’s tight buttocks. They were creamy white in distinct contrast to the nut-brown colour that covered the rest of his body. Andrew had clearly spent a lot of time in the sun wearing only the skimpiest swimming trunks. Mr. Higginbottom had not been joking when he said the young man spent too much time at the beach.

Mr. Higginbottom spread his legs wide and tapped his left leg with the brush. “Bend over my knee.” It was a curt command and one that he expected to be obeyed. Without hesitation, Andrew reached forward and lowered himself over. Immediately, he was in place, Mr. Higginbottom wrapped his right leg around Andrew’s calves, pinning him down. No matter how much agony he felt he would not be able to escape the spanking. He would have to offer up his bared buttocks to Mr. Higginbottom for as long as the old man desired. The spanking would end when Mr. Higginbottom said it would end.

Colin’s cock pressed against his own tightly-fitting underpants as he saw Mr. Higginbottom raise his right arm high in the air before bringing the heavy wooden brush crashing down into Andrew’s right cheek. Colin saw the flesh ripple. Andrew closed his eyes tight and pursed his lips as over and over again Mr. Higginbottom bounced the brush across the naked buttocks. In no time the whole of both cheeks was coloured deep pink.

Andrew bucked and twisted so Mr. Higginbottom grabbed the young man’s right wrist and pushed it up his back and pressed it into his shoulder. There was no escaping the onslaught.

Colin wasn’t counting, but Mr. Higginbottom was. He landed exactly one hundred swats across Andrew’s backside and the top of his thighs. No square centimetre of naked flesh from the top of the globes across the mounds and into the under curves escaped Mr. Higginbottom’s wrath.

“Up!” Mr. Higginbottom released Andrew’s legs and the young man stumbled to his feet. His face was deathly pale, even with a deep suntan. His eyes were moist, but he wasn’t crying.

“Stand in the corner. Hands on head.”

Andrew waddled across the room like a penguin. He made no effort to retrieve his short trousers or underpants from his feet. He had been in this position many times before; he knew the rules. Colin watched intently as Andrew interlocked his fingers and placed his hands over his fair hair. The movement of his arms lifted his green school blazer up his back uncovering his battered buttocks. Andrew had not yet been given permission to touch his toasted bum, but he knew the hard wooden brush would have left his once-soft cheeks with the consistency of leather.

Colin’s cock throbbed. He wanted to dash to the bathroom to whip down his trousers and pants and polish one off. How could he excuse himself from the room?

Too late.

“You boy!” Mr. Higginbottom laid the brush on the table next to his jacket. “Stand up. Follow me.”

Colin rose with difficulty; he was sure his stiff dick would be like a tent pole in the front of his trousers. He was pleased his boss was leading the way and as yet wouldn’t see the young man’s predicament.

Mr. Higginbottom led him up the stairs and halted outside a door. He reached into his trouser pocket and extracted a keyring. In seconds the door was unlocked. It was Colin’s second shock of the evening. The room had been a bedroom once, he supposed. Not now. A great deal of effort had been made to change the room. Oak-like panels lined each wall. The room was dominated by a leather-topped desk. In one corner stood an old battered armchair. There were bookshelves containing what looked to Colin like very old school textbooks.

He took all this in in a single glance around the room. But his attention was drawn to one corner. In it stood a tall vase. He recognised it immediately. He had seen them on sale in T K Maxx in the town centre. But the contents of the vase could not be bought at a shopping mall. There must have been a dozen yellow crook-handled canes.

Mr. Higginbottom read Colin’s astonished look. “Never seen a cane before, lad?” He had adopted his “headmaster’s voice” once more.

“No, I haven’t,” Colin croaked, and then added quickly, “Sir.”

Sir. “Yes,” Mr. Higginbottom thought, “I like that. This should be fun.”

“Well,” he said aloud. “You are in for a treat. Not only is this the first time you’ve seen a cane, it will also be the first time to feel one across your backside.”

Colin stood, his hands strategically placed in front of his bulging crotch, and looked at his feet. He knew he should say something, but no words would come. What did naughty schoolboys say in the stories? He rather thought they stayed silent while the headmaster “jawed” them.

“Go to the vase and select a cane,” Mr. Higginbottom sat in the beat-up armchair to watch the spectacle.

Colin’s hands trembled as he touched a whippy rattan cane for the first time. It was a little over three feet long and as thick as a pencil. It wobbled a little as he withdrew it from the vase. He looked across at Higginbottom the headmaster as if seeking guidance.

“Bend it in your hands, see how flexible it is.” Mr. Higginbottom loved instructing newbies. “Swish it through the air. See how whippy it is. Try to imagine what it would feel like thwacking into your backside.” He rolled the word “thwacking” around his tongue with relish.

Colin replaced the cane and took another. None of them were entirely identical, but there was not much to choose between most of them.

“C’mon, lad,” Mr. Higginbottom was anxious to get on with it, “I haven’t got all day.”

Sweat soaked Colin’s armpits and there was a moustache of moisture on his top lip and it wasn’t only because of the heat of the summer’s evening. He selected a weapon and turned to show it to Mr. Higginbottom.

“A fine choice, young man,” he said as he rose from the chair and turned it round so that its back now faced into the room.

“Give it here,” he reached out and received the cane. He swished it though empty air twice. It made a wonderful Whoosh! Then he tapped the tip of the cane on the apex of the chair’s back.

Colin felt his knees buckle as he waited for the time-honoured command. The one that generations of naughty schoolboys had dreaded. Ever since he could remember he had fantasised about caning and being caned, but he was too shy to make his dream a reality. Now, for the first time in his life he was about to offer up his backside to an older man to chastise.

“Bend over that chair!” Mr. Higginbottom barked the words. He savoured the drama of the occasion.

Colin’s cock was ready to explode. He stepped forward and stood and stared down at the chair. It was a dirty blue colour and worn on both the back and the seat. His penis dug into his stomach after he lowered himself over the chair. He wriggled about unsuccessfully trying to achieve comfort. He stretched his arms forward and gripped the seat cushion with both hands.

“Up over a little more. Head low. Bottom high,” Mr. Higginbottom guided him haughtily.

Colin had imagined himself in this position many times in his dreams, but there was something wrong with the reality. He couldn’t see himself bent across the chair. His only vision was of a dirty worn cushion and his own arms and hands.

Mr. Higginbottom had the best view. Colin was close to six feet tall and while not exactly fat, he was well covered. His buttock cheeks filled out the seat of his suit trousers. They were dark blue with a pin-stripe with sharp creases that extended down each leg and into the buttock. They made a wonderful target.

Mr. Higginbottom “sawed” the cane across the centre of the buttocks and without warning thwacked down the first cut, stunning Colin. His mouth gaped and he let out a silent “ouch.” A line of pain stung him. He wriggled his hips in response.

To Colin, overcome with the excitement of receiving his first real-life caning, it seemed as though time stood still as the whippy stick burnt his flesh with another sharp smack. It lingered for a moment, and then came away, leaving a rapidly reddening tramline across the centre of his bottom.

His only obvious reaction had been a sharp gasp of breath, and a slight toss of the head, but Mr. Higginbottom saw the muscles of Colin’s thighs tensing as the pain reached him.

Colin heard the cane whistling down once more.

“Oooohhh!” he cried out.

His plump cheeks shuddered and he wondered where her breath had gone to. Another red stripe instantly lit up his bum.

“I don’t have to tell you to keep still, do I?” questioned Mr. Higginbottom.

Colin shook his head and buried his face in the seat cushion.

It was six stokes of the cane, but not really Six-of-the-best. Mr. Higginbottom knew how to treat a novice. He regularly thrashed the living daylights out of Andrew. Twelve and sometimes eighteen strokes on the bare arse. The lad’s bum would be criss-crossed with welts. Sometimes they would trickle with blood. Andrew could take it. But there had been a time – and not so long ago – that Andrew had jumped up and down hopping from foot to foot the first time he received only one moderate swipe on his clothed backside.

Colin, Mr. Higginbottom reckoned, had taken his first-ever caning with much more fortitude than Andrew. It gave the old man encouragement for Colin’s future under the cane.

“Stand up,” Mr. Higginbottom was still in headmaster-mode.

Colin hesitated, his nose still smelling the stale cushion. This was too humiliating.

“C’mon lad. It’s over. Stand up.” And, then to offer Colin encouragement, “You took that well.”

Colin eased himself to his feet. His face was more scarlet than his recently-punished backside.

Mr. Higginbottom returned the cane to its home. Then he turned and saw Colin standing in front of him. The young man was mortified.

“Oh dear,” Mr. Higginbottom’s smile was warm. “Perhaps I can lend you some trousers and underpants for your journey home.”


Other stories you might like

My friend Justin

Six of the best caning stories 5. The performance review

In the farmhouse



More stories from Charles Hamilton II are on the MMSA website


Charles Hamilton the Second


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