Trent was holding on as if his very life depended on it. He worked his fist up and down the full length. It was as thick as a broomstick. But not as long. And not as stiff. His heels beat against the mattress every time he kicked his legs. His heartrate was off the scale. Slowly, he eased his fist up and down. He groaned when he took his balls in his hand. The tip of his tongue darted through clenched lips as he cupped the sticky shaft. Slowly. Slowly. It was a battle. He had to slow down. But the sheer joy he felt as the fingers caressed his sensitive stick compelled him to go faster. Huff. Huff. Huff.
No! He told himself not now. Hold it back. Make it last longer. Not now! Not now! His fist slowed. Too late. He arched his back, only his shoulders and feet remained on the mattress. He swivelled his hips. Fell back; crossed his ankles. Too late! With a whoosh of energy it spurted through his shaft. He closed his eyes tightly. He didn’t see that it flew so high it almost hit the ceiling. Hot, sticky goo splashed across his bare chest and stomach.
Huff. Huff. Huff. Oh, the joy, The ecstasy. He opened his eyes and peered down at the mess, rapidly cooling. His breathing eased. His heartrate slowed close to normal. Without turning his body, so none would drip onto the bedsheet, he reached his left arm across the bed to the length of toilet paper he knew was there. He scrunched it up and quickly wiped himself off. He tossed the crumpled tissue onto the floor.
Trent was spent, but the movie continued. He turned onto his side and pulled the laptop closer. It was one of his favourites. It always made him cum. Schoolboys in the headmaster’s study. They were supposed to be sixth-formers but the actors were obviously older than that. Not by much: nineteen or twenty maybe. This one had one of the best of the lot. A fresh faced lad with a cheeky smile. His flat stomach and cute bum were very boyish.
The Swish! movies were the best. They were so professionally done. Real experts. The stories never changed though. Trent didn’t mind. Oh, how he wished he had gone to a school like that. The movie started with a boy they called Jimmy arriving at the headmaster’s study. He is in school uniform. Black blazer, white shirt, striped tie and pale-grey trousers. This time he’s wearing long trousers but often the movies have him in nice tailored short trousers that fall to just above the knee. Trent prefers the boys in ‘longs’ – just like he wore at school.
Jimmy has been caught smoking behind the gymnasium. Smoking tobacco that is. Smoking is the greatest crime imaginable in the world of Swish! movies. Well Jimmy knows what’s going to happen next. The headmaster, who is dressed in traditional academic gown, sometimes with and sometimes without the old-fashioned mortar-board cap on his head, goes to a hat-stand or a cupboard or over to a radiator. In any case he is going to choose a cane. He has a selection, but they are all about the same. They are about a metre long, no thicker than a pencil and all have the traditional – and sexy – curved handle. It is this that makes them authentic school canes, otherwise all the headmaster has is a stick that anyone could to hold up plants in the garden.
Trent is hooked at this point. Blood gorges to his cock when the headmaster takes a cane in his hand and thoughtfully flexes it between his hands to see how far it will bend. He replaces it and takes another. He flexes that one too and swishes it through the air. It is a mighty rod. It will leave marks across poor Jimmy’s bottom for sure.
“Take off your jacket. Take that chair and put it there,” the headmaster intones and Jimmy has to put his blazer on a hook on the door and move the furniture around the study and prepare his own seat of execution. This chair is made of leather with wooden arms. It has a low back and Jimmy will fit across it perfectly as he demonstrates when the headmaster swishes the cane sharply and orders, “Bend over.”
We get a shot of Jimmy’s rascally face as he recognises the gravity of his situation. He does not argue. He does not point out that he is an eighteen-year-old senior boy. He is legally an adult. He is too old for this. Instead, meekly he approaches the chair. He looks at it for a moment while the camera lingers on his back and legs. Then slowly he eases forward. He rests his stomach on the apex of the chair and grips the front of the seat cushion. The material of his pale-grey trousers caresses the curves of his cheeks. They are round and firm. Trent sees this in close up. “Oh,” Trent thinks to himself sadly, “I wish I went to a school like this.”
The headmaster swishes his cane and then taps it across the firmest part of Jimmy’s bottom. “Legs apart. Up over,” he says quietly. Jimmy adjusts his buttocks so that more meat is exposed to the cane. The headmaster steps back. He saws the cane across the centre of both cheeks. The cane rises. It falls, striking Jimmy’s bottom firmly. A line appears in the seat of the pale-grey trousers where the rod fell. Jimmy’s lips purse. His eyes shine. He felt that.
The headmaster delivers six-of-the-best in close up. Jimmy’s face is a picture. Each successive stroke hurts more than the last one. His face glows. He bites his lip. He grimaces. This is an authentic caning. It hurts, but he lives. The headmaster stands back and admires his handiwork. A true schoolboy beating. But he has not finished. “Stand up,” the headmaster intones. “Take down your trousers, then back over.”
The headmaster tucks the cane under his arm and watches as Jimmy hauls himself to his feet. Without looking to left or right, nor even down at his waist, the boy unbuckles his leather belt. Then he pops the clasp of his trousers, pulls the zipper and pushes his trousers down. They bunch at his shins. Then, with no further ado, he goes back over the chair. Trent loves this bit.
Corporal punishment had been outlawed at schools long before Trent was born. He knows that boys regularly faced the threat of the cane across the seat of their trousers. Nobody got it on the underpants. Did they? Who cares? Swish! do not make documentaries. Whoever tossed off to Panorama? Jimmy is wearing white cotton Y-fronts (as much a part of school uniform as blazer and tie). Once he is over the chair they stretch across his buttocks so that they fit like a second skin. The headmaster, still with the cane under his arm, approaches. He hesitates for a moment as if admiring the sights and then with both hands gently takes hold of the tail of Jimmy’s crisp white shirt. The headmaster lifts it and pulls it up Jimmy’s back until it is away from the target area. He reveals an area of smooth, hairless back.
Not yet ready to resume caning, the headmaster now takes hold of the waistband of the underpants. He plays a little game. He acts as though he is going to rip them down over Jimmy’s buttocks and haul them down to his knees so the teenager’s bum is bare. Instead, he tugs the waistband so that the already smooth underpants are even tighter. This way the cotton digs right up the crack and each cheek is lifted and separated. Jimmy has a gorgeous bum. It is (naturally) his prize asset.
The headmaster steps back, slips the cane from armpit to hand and takes aim. Trent sees that the Y-fronts do not fully cover the bum and there are red marks on naked flesh where the cane previously struck. Jimmy’s bottom quivers when the headmaster taps the cane into the underpart of his cheeks, where the bum and thighs meet. The cane is lifted. It strikes. Jimmy’s face contorts. His mouth opens wide. Those beautiful blue-grey eyes sparkle. “Ouch!” he mouths the word.
Jimmy takes another six-of-the-best. Trent sees headmaster. Trent sees cane rise. Trent see tighty-whitey cotton underpants. Trent sees cane fall. Trent sees Jimmy’s startled reaction. Trent’s cock throbs. He reaches for the lube.
“Stand up boy,” the headmaster pompously paces the study. He rests and watches Jimmy sorrowfully get to his feet. Will he ever smoke cigarettes again? Who knows? Trent has long ago forgotten the reason for the punishment. “Underpants down,” the headmaster growls as if it is the most natural thing in the world for him to say.
Trent is in a parallel universe. Usual rules do not apply here. The eighteen-year-old does not tell the headmaster where to get off. He does not stride across the study and punch the headmaster in the mouth and then pummel him into jam as he falls to the floor, before kicking him in the kidneys and leaving. Instead, Jimmy hooks his thumbs into the waistband of his tight, cotton Y-fronts and with no more than a flick of the wrist he sends them south to join his trousers. He turns back to the chair and as he bends forward Trent is given a marvellous close-up shot of Jimmy’s savaged buttocks. Thick wheals run across both cheeks. They are genuinely raw.
Jimmy takes up position again. Head low, bottom high, feet apart. The headmaster does the sawing thing again with his cane and then lets fly. By now, Trent has his eyes closed tight. He concentrates on the job in hand. He can still hear the sound from the movie. The swish. The crack! The arrghhs and ouches from Jimmy, but Trent is now in his own world. How he wants to be that boy bent over the back of the chair. He remembers Mr Watney, the aging headmaster at his inner-city comprehensive school. If only Mr Watney had caned him like that. Trent would gladly have smoked ten cigarettes a day.
In the movie the caning is over. Jimmy is sent to stand to face the wall where he rubs his marked cheeks vigorously. He smiles, a little more ruefully than cheekily. The headmaster sits in the chair. He gestures to Jimmy who at first looks bemused. His confusion does not last long. “Come, stand there,” the headmaster points to a spot beside him. Jimmy understands. He has lived in this unnatural world long enough. Still rubbing his throbbing backside he slowly makes his way across the study. He stands where indicated. “Bend over,” again the headmaster’s command is obeyed without question.
Jimmy is face down across the headmaster’s knee. Trent watches with half an eye. Sometimes in these movies the headmaster makes the boy strip off all his clothes and bend across his knee totally naked. Trent has a movie where Jimmy does this. He looks terrific naked; he is slender, yet muscular. His legs go all the way up to his terrific bum. He doesn’t seem to have a single hair anywhere on his body – not even around his cock.
Sexy though Jimmy is naked, he prefers the boys to be at least partly dressed. It makes the scene more authentic. Trent lets the movie move to its conclusion. He glances at the time in the corner of the screen. It is time to go. Carefully, so none of the cum drips onto the bed, he climbs off the mattress. He picks up the soggy Kleenex from the floor and walks across the room. He drops it into the lavatory pan, has a piss and then turns on the shower.
Minutes later, towelled dry, he opens a drawer and selects the clothes he will wear that night. He has tight-white Y-fronts, a grey shirt and grey trousers. He doesn’t have a blazer, but he doesn’t think he needs one. He slips a striped tie into his trouser pocket. He is off to The Three Fishers where he is certain to meet Fat Steven. He is always there on a Friday night. Fat Steven will bring the cane.
Picture credit: unknown
Other stories you might like
More stories from Charles Hamilton II are on the MMSA website
Also writing school stories as Scholastic here
Charles Hamilton the Second