Pyjama bottoms down. Bend over (again)



A version of this story from the housemaster’s point of view is here

James “Tommy” Tomkins stepped into his pyjama bottoms, pulled the drawstring tightly and then tied a double bow. With some resentment he leaned over the bed and picked up the striped jacket. He found the arm holes and climbed in. He was nearly ready.

What a swizz, he thought. Summoned to his housemaster’s study. Just before lights out. It would be a whopping for sure. And on the pyjama bottoms at that.

Tomkins was eighteen years old, a member of the upper-sixth. He thought he was an adult damn it. But, eighteen or not, he had broken the school rules and now he would pay the price. How had smoking cigarettes suddenly become a crime? Until the new headmaster arrived sixth-formers were left to themselves. They were expected to study hard and ensure that the younger boys kept in line; but they were pretty much left to their own devices.

Not anymore. Dr Tredlow the new headmaster was a man on a mission. Unluckily for the senior boys, his mission was to tame them. He was evangelical in his belief that sixth-formers were schoolboys just like anyone else. They were not adults; they were children. And they would be expected to obey the rules just like any junior boy.

So, out went drinking whisky. The poker games were abandoned. And any sixth-former caught smoking could expect to find himself over the housemaster’s desk with his bum pointing to the ceiling. That was exactly what had happened to Tomkins, three weeks previously. Six-of-the-best. In fact, six of the very best. His housemaster Mr Teddington was no slouch when he had a cane in his hand.

Tomkins had a problem and he wasn’t the only eighteen-year-old at the school who suffered. He had smoked so many cigarettes in the past years that he had become addicted to tobacco. He could not give it up. And, like all addicts he had become skilful at hiding it from those around him. But not skilful enough. Mr Heath, a junior maths master, had spied him in a nearby copse puffing away on a Woodbine. What Mr Heath was himself doing in the copse has gone unrecorded. But, the junior master, perhaps anxious to curry favour with his elders and betters, reported Tomkins to his housemaster.

Tomkins looked across the dormitory at his dressing-gown hanging on a hook. It was a warm evening; he would leave it where it was. Besides, he would only have to remove it once he was inside old Teddy’s study.

Still full of resentment, Tomkins left the dorm and made his way along the gloomy passageway to meet his maker. He paused at the heavy oak door, raised his fist and tapped lightly. There was a pause and then he heard the stout command of his housemaster, “Come.”

Tomkins was in no hurry. He knew he was due a beating. He turned the handle slowly and very reluctantly pushed the door open and stepped cautiously into the study.

Mr Teddington was sat in a luxurious leather chair, reading a newspaper with a pipe in his mouth. A fug of smoke surrounded him. Tomkins glared at the injustice. He intends to beat me for smoking, he thought, look at him puffing away. What an example he sets, the boy thought bitterly.

“Come in boy! Don’t dawdle! Close the door!” the housemaster snapped.

Tomkins closed the door as instructed and stood only a couple of paces inside the room, unsure what to do next.

The silence was deafening. Tomkins hopped from one bare foot to the other. “You wanted to see me sir.”

The housemaster peered at him over the top of his reading glasses, dripping distain. “I’m not yet ready for you! Face the wall and wait for me.”

Tomkins looked around the study unsure where he was meant to go. It was a large room; one side was dominated by an as-yet unlit open fireplace. Mahogany bookshelves behind glass doors ran the length of the room alongside it.

The other main wall had closed cupboards, for teaching materials and so-forth. One cupboard that was taller and narrower than the others contained implements of an especial educational nature.

“There boy,” Mr Teddington pointed with his pipe to the corner nearest the door. Tomkins could hardly disguise his irritation. The housemaster was enjoying this too much. The sixth-former turned around to face away from his tormentor.

“Closer boy! I want to see your nose touch the wall.” Tomkins shuffled into position.

“Hands on head!” The housemaster was determined to treat Tomkins like a junior boy, as if he were one of the fags.  Tomkins puckered his lips; he could not argue with the housemaster, but he could express his irritation with the man.

He interlocked his fingers and placed them on his head. His nose was so close to the wall he could smell the dust on the wallpaper. Behind him, he heard the sound of newspaper rustling in Mr Teddington’s hands. The stink of his pipe wafted across the study.

He was kept waiting for probably only a few minutes, but to the boy awaiting a thrashing it was an eternity. The housemaster was truly a sadist.

“Turn around Tomkins,” the housemaster ordered. At last, Tomkins thought. Let’s get this over with. He swivelled on the balls of his feet and faced the housemaster. His hands were still firmly on his head.

The housemaster growled. “Come forward and stand in front of me.” Tomkins did. At such a close range it was noticeable that the schoolboy was easily two or three inches taller than the master. Tomkins was thin and wiry, while the housemaster was portly. In a fair fight, Tomkins could have knocked the man to the ground with a single blow. But this was not to be a fair fight. The schoolmaster was in complete control. The boy, eighteen years old or not, had no choice but to obey the orders of his persecutor.

“Take your hands off your head and stand up straight.”

Tomkins exhaled an inaudible sigh and did as he was told. His attention wandered as the housemaster jawed him. Smoking cigarettes was a disgusting habit, he said. It was bad for the health. But, more than that, it was against the rules. Tomkins knew that; he had been beaten once already this term.

“So, you deserve a sound thrashing and that is what you will receive. I’m giving you twelve cuts on the bare.”

Tomkins’ eyes blazed. Twelve. On the bare. That was twice the usual punishment and nobody, as far as he knew, was ever beaten bare. The colour drained from his already pasty-coloured face, but he remained standing, silent, waiting for further instructions.

His eyes followed the housemaster as he went to the tall, narrow cupboard and took out the cane he had already decided to use. It was dark yellow in colour, quiet thin, but made of very dense rattan. It would leave its marks on Tomkins’ behind for many days to come.

Mr Teddington flexed the cane thoughtfully between his hands, then swished it through the air. It looked an awesome weapon, much more threatening than the stick the housemaster had used to beat him last time, Tomkins reckoned.

“Stand by the desk,” Mr Teddington pointed with the cane. Tomkins hesitated. Damn it, he thought. I’m eighteen years old, a prefect. I’m too old to be caned. He breathed deeply, debating with himself whether he should voice a protest.

What would be the point? Tomkins and the other fellows in the Sixth knew the new discipline regime was instigated by the headmaster. If he argued, or worse still refused to be caned, he would find himself up before Dr Tredlow. The brute would probably birch him in front of the entire school. No, Tomkins knew, he had to let matters take their course. He had to offer Teddy his bare arse.

He moved towards the desk, but stopped short by two or three feet.

“Right up to the desk, boy.”

He moved forward a little more.

“Get those pyjamas down boy.” Tomkins blushed. It was not that he had never taken his trousers off in public, he had. Each night he changed into his pyjamas in a dormitory full of boys. He had seen the “privates” of many young men and they had seen his. But, he resented having to strip for the pleasure of the old brute standing before him. To strip and then offer up his bared buttocks to the master to whip with his swishy cane.

After some moments, Tomkins looked down at his waist, pulled at the drawstring holding his pyjama bottoms up and allowed them to fall to his ankles.

Mr Teddington stood within Tomkins’ eye line, but the boy studiously ignored him. Then, the housemaster swished his cane through the air two or three more times. Then he tapped it against the desk.

“Bend over.”

Without question, Tomkins leaned forward, resting his stomach on the desk top with his arms stretched to his front and overhanging the end of the desk. His pyjama jacket was covering his bottom. Mr Teddington pushed it further up his back.

“Underpants Tomkins. You don’t wear underpants with pyjamas. Stand up. Did you think underpants would give you extra protection?”

Tomkins rose, sullenly. Protection? Did the wretched housemaster think he was a coward, he thought? Tomkins always wore pants; it was the only way to keep his erect cock from poking out the pyjama flies.

“Get them down,” Mr Teddington barked.

Sorrowfully, Tomkins took hold of the waistband of his underwear and pulled them down to his ankles, where they rested on top of his pyjamas.

“Bend over boy.”

Tomkins repeated the manoeuvre. The housemaster pushed his pyjama jacket up, this time revealing a pair of smooth and hairless buttocks.

“You are about to learn a very painful lesson young man.”

Tomkins closed his eyes and shut his mouth tightly. He felt the tap of the tip of the cane exploring his buttocks. The housemaster seemed to be taking an excessive amount of time. A wicked thought struck Tomkins, “He’s admiring my bum.” And then he had a more horrifying thought, “He can see right up my crack and into my hole.”

What he could not see was Mr Teddington standing to his side a full cane length from him and bending his knees a little. The housemaster drew his arm back several feet and crashed the cane across both buttocks. Tomkins whelped and a thick red line immediately appeared where the cane had bitten into flesh.

A second stroke immediately fell, landing an inch of so lower than the first. Tomkins gasped and jerked his head.

“Feeling that aren’t you boy?”

“Yes, sir,” he replied, even though it had been a rhetorical question.

Pain started at the buttocks and travelled at speed up and down the boy’s legs. He could feel two thick welts rising, running across both his buttocks.

The third and fourth cuts landed across the previous two. The agony was searing. It felt like the cruel housemaster had laid a white hot wire across the sixth-former’s cheeks. Tomkins jerked his body from left to right. He buried his head in his folded arms.

Mr Teddington lashed down strokes five and six. The agonizing slices cut in wickedly, stinging fiercely, making Tomkins squeal, rock and writhe violently.

The housemaster swiped a couple of strokes high and a couple low. The sickening pain quickly overwhelmed Tomkins’ senses

“Arrrggghhhh.” The boy bit into his own arm after the next cut slashed into his quivering buttocks.

The final stroke was whipped in diagonally across both of Tomkins’ buttocks, hitting many of the previously delivered cuts as possible. Tomkins’ face was almost as red as his backside. His eyes were damp and he was trying hard not to cry.

The housemaster tapped the cane once more across the lacerated bottom. Tomkins braced himself, expecting another slash. But, there were to be no more. Mr Teddington tapped the cane on his left buttock one more time.

“Don’t let me catch you smoking again.”

“No sir.”

Tomkins lay face down across the desk, breathing heavily. His bottom was a furnace. Never before had he felt such pain. His smooth, hairless, previously white, bottom was a mass of red welts. Some were turning blue and would change to purple before too long. Blood was forming at some of the intersections where the final diagonal cut had crossed the others.

“Stand up Tomkins. Get dressed.”

Tomkins shot up from the desk. The pain was great; the humiliation even greater.  He wanted to get out of that study. Tears of pain and shame welled. But he determined he would not cry in front of the brute. He would not. He would not give him the satisfaction of knowing he had hurt him badly. In one swift movement he bent down to grab his underpants, but it was with great difficulty that he pulled them up to his waist. He winced in agony as he tugged the Y-fronts over his buttocks and they connected with his wounds.

He bent down to his ankles again to retrieve his pyjama bottoms, flinching as he stretched the flesh of his buttocks against his pants. He pulled at the drawstring of his pyjama bottoms and with trembling fingers made an imperfect double-bow. That would have to do for now.

“Back to your dormitory. No more trouble,” Mr Teddington snarled.

He was through the door in a heartbeat.



Other stories you might like

Yellow Pages spanking

Theft of petty cash

The rooming house


More stories from Charles Hamilton II are on the MMSA website

 Charles Hamilton the Second

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