Rory and Alistair Ep 1. The Head Prefect

Rory MacDonald eased down the handle of the dormitory door with his elbow. His arms were full of cricketing gear and he feared one of the bats was about to tumble to the ground.

He was sweltering in the ninety-degree heat. Would this heat-wave never end? In an ungainly fashion he had the door open and stepped inside. He flashed one of his trademark grins; it split his face in two. In front of him was his best friend Alistair. The eighteen-year-old lay face down on the bed snoozing. He was dead to the world – and totally naked.

Quietly so as not to wake his chum, Rory let the cricket gear fall on to his own bed. Then he sat down and gazed in admiration at Alistair’s body. He was a fine-limbed athletic boy; about five-feet-eight in height. He was hairless on his chest face and buttocks and there was merely down on his legs.

Rory shook his head in amazement. Alistair’s arse and thighs were covered in awesome blue-black bruises. Even from across the room the boy could see the distinctive oval-shaped mark left behind by the hairbrush, which clearly had been applied with some vigour.

Rory looked at his watch; it was time they both got going. He hauled himself from the bed and crossed the room so that he stood towering over his friend. Come on Alistair, he thought, we have a date in town.

Then puckering his lips and leaning forward he planted a wet kiss in the centre of Alistair’s firm left buttock.

The boy awoke like a princess in a fairy-tale.

“Ouch! That hurt,” he grinned.

“Ouch! That hurt,” his friend replied satirically, mocking Alistair’s tone. Both boys exchanged huge grins, puckered up and kissed each other on the lips.

“Pendleton?” Rory asked, nodding at his friends toasted buttocks.

“Who else?” Alistair’s grin never faded. He was not about to let his recent ordeal upset him.

Pendleton was the Head of Wilson’s House. And Pendleton had his own way of instilling discipline among his charges. All the boys who were Head of their House at Willadong Academy were allowed to inflict corporal punishment. There was no set law, but by custom and practice the rattan cane was the instrument of choice. Some Head of Houses used a rubber-soled gym shoe on the youngest of the boys.

Only Pendleton used a hairbrush, applied to a boy’s bared bottom while he was draped across the lap of the Head of House. And, Pendleton did not care about age and seniority. He would just as easily take eighteen-year-old Alistair Crombie across his knee as the most junior fag in the school.

Alistair and Rory were oddities at the school. They were both in their final year at the school, but had never received any privileges. Although they were old enough to be in the sixth-form, they were treated by everyone, masters and fellow pupils alike, as juniors.

They were even required to dress like juniors. Only boys in the sixth-form were permitted to wear long trousers: it was seen as a badge of privilege. The two boys remained in short trousers and would do so until the day they left school. Not that they cared. Temperatures rarely fell below eighty degrees for most of the year; let the “privileged” sixth-formers swelter in their heavy flannel trousers, it was much better to be free to the wind in short trousers.

A short-sleeved white shirt completed the summer uniform at Willadong. Mostly boys did not wear ties or even socks. They would run bare-footed around the school buildings and slip into thongs when outside.

Rory and Alistair could never conform to boarding school life with its myriad rules and regulations. Get up at seven, bed at nine-thirty. Don’t do that; don’t go there. They were more suited to the life of the boys in town. They had made many friends in Woolverton and how they envied them their freedoms. None of the teenagers they knew had fathers who would order them to bend across the armchair for six stingers from a whippy cane because they were out of bed at midnight.

Alistair’s blazing bottom was the result of one such adventure. Bored and unable to sleep, he had climbed through the window and taken himself for a walk. He committed no mischief; he disturbed no boy’s sleep; all he did was to enjoy the moonlight and the clear warm air of midnight.

He was spotted and in the usual matter of course he was reported to Pendleton. Pendleton was not such a huge fellow. He probably was an inch taller than Alistair, but a little thicker set. The Head of House was a fine cricketer and could slog a cricket ball way over the boundary. He had great upper body strength which he put to good use with the hairbrush.

This was not even the first time the eighteen-year-old had been across Pendleton’s knee. The first time he had been ordered to unbuckle his belt and pull down his short trousers, he had been bewildered. He had expected the standard six-of-the-best on the seat; probably whipped in with some force; everyone knew that Pendleton was a bit of a bully. But, to be ordered to go across the prefect’s knee like he was six years old was a shock.

Alistair had no choice. The alternative would have been a visit to the headmaster’s study and a thrashing of a lifetime, almost certainly bare arsed and no doubt with the awesome Malacca cane. That could take a boy’s backside off, leaving him in considerable pain for many days.

No, unconventional though it was, Alistair had to submit himself to Pendleton.

The hairbrush had once belonged to his nanny. Pendleton had felt its sting across his own bared bottom many times until when at the age of eight he was sent off to prep school. The hairbrush was the only memento he had of nanny; he stole it from her room the day he found her dead in her bed.

The over-the-knee bare-bottom spanking hurt like crazy, but it was nothing like getting the cane; even when wearing trousers and underpants. Alistair supposed the ordeal was meant to humiliate him. If so, Pendleton had chosen the wrong boy. He dropped his short trousers and unbidden stepped out of them. Then perfecting an air of unconcern, he put his thumbs in the waistband of his pants and lowered them down his thighs and let them fall to his feet, then he stepped out of them too and kicked them a few feet behind him. He now stood naked from the waist down in front of his would-be tormentor.

Alistair was very proud of his body and was not ashamed to be seen naked. His pal Rory was one of his greatest admirers and often they would compliment one another on their anatomy. Rory, for one, had a very distinctive penis; it must have been almost the only uncut specimen in the whole school.

Rory had no idea what was going through Pendleton’s mind as he draped himself across the boy’s legs, lowered his head so he was almost kissing the carpet and keeping his own knees straight, raised his taut athletic buttocks high to receive his spanking.

Wow! Pendleton was in a frenzy. Had some demon taken possession of him? Relentlessly he whacked the heavy oval hairbrush up and down into and across both buttocks. With no respite between smacks, he covered every square inch of buttocks and thighs inside thirty seconds and then he just kept on whacking and whacking.

Alistair had never been spanked like this before, so he was not sure how much it was supposed to hurt. It did considerably, but to his puzzlement he found the pain increased rapidly with the first few dozen slaps and then plateaued. He had gone through some king of pain barrier. After a time, he could feel the heavy wood crunch into his globes but each additional whack did not increase the pain.

The teenager sucked in his breath and waited as patiently as he could in the circumstances for Pendleton to complete his task.

He was beaten quite literally black-and-blue. But, even as he climbed back into his underpants and short trousers Alistair realised the pain had subsided, leaving behind a gentle throb that quickly turned to a warm glow. Some parts of his bum, especially the bit where the cheeks met the thighs were tender to the touch and he might feel the spanking for some time when he sat down on a hard surface.

Pendleton was a young man of few words and he dismissed Alistair without benefit of a lecture. As he exited the study, Alistair turned and flashing his sparking white teeth, he grinned, “Thank you Pendleton, I enjoyed that. I hope you did too.” Then he closed the door and ran down the passageway in case the Head of House had resolved to drag him back inside for a repeat performance.

 

Episode 2 is here.

 

Other school-based stories you might like

Six of the best caning stories 1. The sixth-formers

The padded armchair

Murph in the headmaster’s study

More stories from Charles Hamilton II are on the MMSA website

Charles Hamilton the Second

charleshamiltonthesecond@gmail.com

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