Tompkins in the housemaster’s study

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Tompkins stared down at the dirty grey carpet. From his position he had an excellent, close-up view. It wasn’t the first time he had been in this position with his knotted striped tie dangling in front of his face and his fingertips brushing the toes of his black, shiny shoes. It probably wouldn’t be the last time either, St. Tom’s was that kind of school.

He waited, stoically. He was in no hurry to have his backside blistered one more time by the housemaster. His heart raced as he felt the tail of his shirt being raised and folded up his back.

He tried to ignore the sight of his pale-grey trousers bunched at his ankles. His back was arched, it ached a little. Touching toes was more difficult than it looked.

He could feel his white Y-front underpants stretched across his firm bottom. They fitted a bit too snugly and rode up into his crack. Not that it made much different, this was to be a bared-bottom caning. Not that the thin cotton pants could offer any protection against the housemaster’s thick, but whippy rattan cane.

Tompkins felt the housemaster’s warm hands on his flesh as he took hold of the elasticated waist of his underpants. Then they were fluttering down his legs to land on top of his trousers. Now, he was ready for a stinging Six.

The housemaster wasn’t quite ready. He had a ritual and it included preparing a boy by uncovering his bottom and then going to fetch the crook-handled cane that dangled from the hat stand in the corner of the study. From the corner of his eye Tompkins watched the headmaster’s feet as he made his journey. A cool breeze from an open window tickled Tompkins’ naked legs.

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He could hear, but not see, the cane being lifted from the stand. It made a slight rattle. There was a pause, followed by a tremendous whooshing noise as the headmaster swished the cane through the air. Tompkins’ heart skipped a beat. It usually did at this moment, even though he was eighteen years old and no stranger to the sting of the rattan across his stretched bottom.

The housemaster’s creaking footsteps announced he was nearly ready for action. He stood to Tompkins’ left and slightly behind him. Again, the boy could see him from the corner of his eye. The feet swayed slightly. Tompkins knew that the cane was high in the air. Any moment now!

Swipe! Crack!

Tompkins grunted as the cane landed in the centre of his naked cheeks. It was a real stinger. The housemaster put all his beef into it. He could lay it on when he wanted to. Tompkins knew he was really going to take his backside off. He expected nothing less. The housemaster was a renowned caner, one of the best (or the worst, depending on your point of view) in the entire school and he had many rivals for that honour.

The housemaster waited, counting slowly to twenty in his head; waiting for the pain in Tompkins’ bottom to ebb away. Then he lashed the second stroke, landing it an inch below the first. The pain rose sharply to a new peak. He was rewarded with a sharp exhalation of breath. Tompkins screwed his eyes tightly and shut his teeth. Before the housemaster was finished Tompkins’ rear end would be a raging fire.

The third cut made him yelp and he rocked on the balls of his feet. His fingers shot up off his toes but he quickly grabbed his ankles and this stopped him jumping to his feet. He must avoid that at all costs: he didn’t want extra strokes. His bottom roared like mad, he knew three deep welts were throbbing across the middle of his bum, expertly delivered in a strip no more than two inches wide and perfectly parallel. There was still plenty of space on Tompkins’ quivering bottom for more strokes.

Crack!

“Yarooh!”

It was a full-throated cry. Tompkins couldn’t help it. He shook his head from side to side as the excruciating agony coursed north-south; east-west throughout his body. His bottom wriggled.

“Steady, boy,” the housemaster intoned. Tompkins watched the housemaster’s feet, whenever he raised the cane, he dug his heels into the carpet.

Tompkins clenched his buttocks as he waited for the next stinger. It was a natural reaction. His bottom tried to compressed itself into something approaching a hard, rubber ball. It was supposed to be a protection from the stick. It didn’t work.

Slash! Slash!

Two in quick succession. Tompkins’ bottom felt like it had been cut open with a razor. His knees buckled and he let out a shrill scream. He was fighting back the tears. The housemaster’s shiny shoes disappeared. Tompkins knew then that he was returning the cane to its resting place.

Tompkins waited, head low, bottom high, fingers now back on toes. The punishment wasn’t yet over. The housemaster had one final ritual to perform. With the cane now safely stashed away until the next time, he sauntered over to Tompkins. The boy held his breath. This was the worst part. The housemaster patted Tompkins naked rear and gently caressed the corrugated flesh. Then, the hand rose and slapped down hard first on the left buttock and then the right. They were painful blows, reigniting the cuts on Tompkins’ roasted rear. He wriggled from side to side.

“Up you get!” the housemaster ordered brightly.

Tompkins sucked down a lung-full of air and slowly straightened up. The housemaster stood directly in front of him, gazing at Tompkins’ cock as it bounced up and down while the boy struggled into his Y-fronts. Soon, his trousers were back in their rightful position
Now, fully dressed again, Tompkins gingerly rubbed the seat of his trousers. “Thank you, sir,” he croaked and he hobbled towards the study door.

“My pleasure, Tompkins,” the headmaster replied graciously.

Picture credit: CP Services, London

 

Other stories you might like

If you dress like a little boy …

Dad, spank me please

An old English custom

 

More stories from Charles Hamilton II are on the MMSA website

Also writing school stories as Scholastic here

Charles Hamilton the Second

charleshamiltonthesecond@gmail.com

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