Rory and Alistair could never conform to boarding school life. The eighteen year olds were oddities at Willadong Academy. They were required to dress like juniors and would remain in short trousers until the day they left school. They had one other characteristic that distinguished them: they were madly in lust with one another.
Alexander Macaulay the junior schoolmaster stalked the passageways of Willadong Academy, a cane tucked under his arm. He was determined it would see action before the afternoon was out.
It was Wednesday and at Willadong that was a time for compulsory sports. If Macaulay found a boy in the building that would be excuse enough. If no abstainer was to be found he could instigate a room search, seeking hidden contraband. Cigarettes and alcohol and much else besides were strictly banned at the school.
Alexander Macaulay was an unhappy young man. This was his second month at the school and things were not going well. He was twenty-four years old; and to many casual observers indistinguishable from the senior pupils. He stood no taller than five-feet-seven-inches and was lean and wiry. His smooth complexion was deeply suntanned but the thin straggly moustache he sported belied his age. He was a boy trying to be a man. He did not possess the “gravitas” required to be a schoolmaster and probably never would.
The tingling he still felt in his backside confirmed this. It had been the most humiliating moment of his life. Less than thirty minutes previously he had been in the study of Willadong’s senior master Mr. Henderson; bent across a stout desk, trousers at his ankles. Henderson swiped nine hard cuts across the junior schoolmaster’s swaying buttocks.
Henderson said it was “attitude.” Macaulay must “buck up his ideas.” He must show he was worthy of the title, junior master at Willadong Academy. Until such a time, Macaulay must expect to be treated as if he were a pupil. “Trousers down, bend over.”
Now, Alexander Macaulay was on the prowl. Somebody must pay for his humiliation.
Rory and Alistair lay naked, entwined in each other’s arms. They had had sex enthusiastically, but inexpertly. Alistair’s cock was stiff at a forty-five degree angle. It was ready for round two.
Fresh weals decorated the buttocks of the two eighteen year olds. They were the handiwork of Mr. Anderson, their housemaster. It had been six on the bare. They were repeat offenders.
The pain had gone now, but there was one deep cut across the very centre of Rory’s bum that was tender to touch. The cane had landed on the same spot twice. A slash that landed across the back of his thighs troubled Alistair. That should teach him not to wriggle about during a caning.
Some boys were not suited to boarding school life. Roy and Alistair were two of them. There were too many rules and restrictions. The two pals were not resentful. They had broken curfew – again. Rules were rules at Willadong and when they were broken a lad would expect to be showing his arse to a prefect or a master.
Rory freed himself from Alistair’s embrace and lay face down on the bed inviting his chum to inspect his wounds. The teenager licked his own index finger and gently used it to trace from one end to the other of the deep welt across Rory’s bum. It had once been a deep pink, but now was mauve. It would turn purple soon, and then over the next few days it would lighten to yellow and finally disappear.
Alistair created a spit ball in his mouth and washed his tongue with it. Then he licked Rory’s cut, sending a shiver through the teenager’s body and leaving a slime trial across the buttocks. Rory’s cock throbbed almost as much as his bottom had just after his thrashing.
In the distance the school clock struck three o’clock. The boys were missing compulsory cricket practice. Who cared? What was another spanking between friends?
Rory turned on his back and Alistair snuggled up beside him. They took hold of each other’s cocks and tugged.
It was Wednesday afternoon; sports and activities day at Willadong. Rory and Alistair were keen cricketers and part of the school XI team. They should have been with their fellows practising. It was a scorching hot day; like so many that summer. The cricketers were broiling so had left their whites behind in favour of the shortest cotton running shorts they could find. Some wore vests but most were bare-chested.
Cpt. Cameron their PT instructor and cricket coach was not a happy man. He had been absent from the school and had engaged a man called Villiars from the village to stand in. Cricket was a gentleman’s game but the sixth-formers at Willadong had been far from gentlemen to Villiars. Willadong boys considered themselves superior to the common man and were not about to be ordered about by a village oik like Villiars.
But now Cameron was back and he did not like what Villairs had told him. Not one little bit.
That was why six eighteen-year-old cricketers were lined up in the pavilion facing Cameron. The PT instructor held a dirty-white plimsoll tightly in his right hand. It was a large slipper and rather worn on the sole. It had seen much action on the running track and also across the bending backsides of errant schoolboys.
He devised a little ritual. The eighteen year olds stood in a line, backs to the wall. Then on command each one stepped forward three paces towards Cameron. They swivelled on their heels, lowered their white shorts (none were wearing underpants in that heat) and touched their toes; knees straight. Three of the six teenagers wore no shirt so were totally naked bent over obediently with their tight cotton shorts in a puddle at their feet. It was a typical schoolboy ritual; each one presenting himself submissively to his master.
Schoolboy cricketers come in many shapes and sizes. There is no requirement to have an “athletic” body; “big and meaty” could as easily fit the bill. Six sets of naked buttocks were displayed that afternoon: fat and squashy; large and firm; pert and pimply.
Cameron had the perfect view of each boy’s cock and balls and, of course, his crack. But the middle-aged ex-Army officer was not interested in any of that. Discipline and punishment were uppermost in his mind. He gripped the plimsoll tightly and whacked it down across flesh. Two spanks on the left cheek; followed by two on the right.
Then, the boy stood, pulled up his shorts and went back to the wall, to be replaced by the next boy.
And so it went on until all six teenagers had the dark pink outline of the slipper emblazoned across both buttocks.
It looked spectacular, but it didn’t really hurt. Not like four slashes from the headmaster’s special Malacca cane would have if he had learned of the boys’ discourtesy to Villiars.
Alexander Macaulay was despondent. Somebody must pay for his humiliation. He had searched the classrooms without success. No boy was to be found. Now, he made his way through the living quarters. Again, there was no sign of life.
He searched through the study rooms. The boys seemed to have very few personal possessions. For the sons of the wealthy they were very poor indeed, he concluded. The boys would have found the junior master’s naivety touching. They were wiser than that. No self-respecting boy would leave contraband in his room for prying eyes to find. It was secreted in cubbyholes and nooks and crannies across the school; places unknown to the likes of Alexander Macaulay.
He was close to the end of his tour. Only one passageway was left unexplored. The junior master let himself into an unlocked room. As with the others, there was not much there. He opened and closed cupboards and drawers. He was exasperated with himself: what had he expected to find?
Idly he pushed a textbook across a desk. The corner of a picture poked out from between its pages. He tugged it free. It was a page ripped from a magazine. A picture. A captivating photograph.
Two young men, in their twenties, standing side by side grinned at the camera. They had their arms around each other’s shoulders. They were sailors. At least they wore sailors’ hats on the backs of their heads, but little else besides. Only the shortest of denim shorts. The waistbands were unbuttoned and their zippers lowered, enticingly. Their chests were hairless and stomachs tight and flat.
The boy on the right was particularly enchanting. His dark curly hair fell across his forehead emphasising his dreamy brown eyes.
Carefully, Macaulay folded the picture and tucked it into his pocket. Then, fearing he might be caught, he tip-toed from the room.
There was now only one room left unvisited.
Voices. He could hear voices from behind the door. Success. Finally. His afternoon would not be wasted.
Had the junior master been less junior; he would have recognised the room, if not necessarily the voices of its occupants. And, he would have known better than to burst open the door without warning.
Rory and Alistair lay naked. Spent. Breathing hard. Their exertions had been great. Semen covered each boy’s stomach.
Alexander Macaulay stood in the doorway startled. Instinctively, his eyes focused on Alistair’s cock. The junior master had seen nothing like it before. It was flaccid and limp, but even relaxed it was an awesome specimen. And uncut. He had never before seen an uncut cock.
Macaulay blushed deeply. His mouth opened and closed, but he could not get words to form.
Rory raised himself to a sitting position. He stared at the intruder to his room. He only vaguely knew the identity of the stranger. The cane tucked under the junior master’s arm confirmed he was trouble.
“Wha.. wha…?” Macaulay tried again to speak, aware that he could not stop gaping at the two naked sixth-formers before him. One of them, not the one with the huge cock, reminded him of the boy in the picture.
Rory flashed a grin, his dark brown eyes sparkled, but he said nothing, silenced by the sight of the bulge now growing in the front of the visitor’s trousers.
Alistair had seen it too. The caller was quite attractive in a nerdy shy way, he thought.
The junior schoolmaster slipped the cane from his arm into his hand, as if ready for disciplinary action.
Rory roared with laughter.
Macaulay stood rooted, unsure what to do next. He watched as Alistair sat up and the two boys embraced; just like the two sailors. The throbbing in his pants was excruciating.
Alistair giggled, “Don’t stand there all day. Get your clothes off. You can squeeze between us.”
He stopped short, felled by the Macaulay’s face of thunder. The junior schoolmaster wanted revenge for his earlier humiliation. Now he was going to get it.
“No!” He had found his voice at last. He might have been a schoolmaster for only two months, but he understood and relished the power he had over the two teenagers. They must submit to his cane. The consequences of refusal would be dire: a flogging from the headmaster and possible expulsion from the school.
Macaulay swished the cane through the air. He stared Alistair in the eye and slowly and deliberately said, “Let’s have you on your feet and over that chair.” He wobbled the cane at a small straight-backed chair.
To his delight, the boys rose from the bed without question. Alistair clutched the chair and placed it in the centre of the room.
Macaulay’s heart raced. He had never felt such power before. The boys would submit to his will. He watched Alistair make the preparations and start to bend his body over the chair.
No, Macaulay thought. I’ll do the cute one first.
“You,” he pointed at Rory, realising that he didn’t know the names of either boy before him. “You first.”
Rory smiled. It nearly broke the schoolmaster’s young heart.
Rory didn’t fit in at Willadong Academy. It did not suit his personality, but he rarely resented the treatment he received at the school. He broke the rules, he got punished and life went on.
But, not this time. Rory was not a man of the world, but he understood enough. The throbbing cock beneath the schoolmaster’s trousers did not lie. Macaulay was about to beat him on the bared backside for his own sexual gratification. Later, the schoolmaster would pleasure himself while he relived this afternoon in his head.
Rory despised Macaulay for his hypocrisy. He would thrash him and his friend for fooling around. Yet, the schoolmaster so clearly wanted him.
Even before Rory gripped the hard wooden seat, he had devised a plan. Later, sometime soon, he would entice the schoolmaster to a dark secluded part of the school. He knew many such places. Macaulay wouldn’t be able to resist. It wouldn’t take long. A schoolmaster. Sex. A male pupil. There was no need to spell it out.
Rory closed his eyes, clamped his teeth shut and offered up his already corrugated buttocks to the lash of the cane.
Picture credit: Cover of Muscleboy, February-March 1964, by David of Cleveland
This story was first uploaded in February 2016.
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More stories from Charles Hamilton II are on the MMSA website
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