The first time I saw the boy was one Saturday at Rowley’s hardware shop just off the High Street. He was coming out of the store. He was a store assistant and wore the company uniform of pale grey trousers, white shirt and plain navy blue tie. Pinned to his shirt was a name tab: William. I don’t know if Old Man Rowley had some kind of kink, but he dressed his assistants to look like overgrown schoolboys. I stared mesmerised by his tight arse as he sashayed over the road and went into a café.
I next saw William several days later, quite by accident. He was alighting from a bus. To my utter delight he was indeed a schoolboy. He was dressed in the distinctive green-and-gold blazer of St. Francis Independent Grammar School. And, oh glory, on his head was perched a school cap. Even from a distance I could see a rectangular badge on his lapel; the symbol of a prefect.
St. Francis, or St. FIGS as the locals called it, not always with affection, was one of the poshest schools in Brocklehurst. Not as posh as St. Tom’s the public boarding school I had attended and where I rose to the exalted rank of School Captain. St. FIGS was a step below a “public” school which are in fact exclusive private schools for the wealthy. But it was above a state grammar and in a different stratosphere to a secondary modern.
I adored William in his school uniform and school cap. I knew at St. FIGS younger boys were forced to wear grey short trousers. Oh, I dreamt, how wonderful it would be to see William dressed that way.
I didn’t stop to think. I had no conception that my next action might be considered weird; perverted even. Keeping a safe distance so as not to be spotted, I followed William. He had a steady gait. He was a fit young man, no taller than five-feet-seven-inches. I was becoming a connoisseur of young men and expertly estimated he had a twenty-seven-inch waist. His body was toned by exercise. He was no Muscle Mary. I supposed he did not spend hours in the gym; he probably did school sports, athletics perhaps.
My surveillance lasted a matter of minutes. He walked about fifty yards down the street before turning into The Avenue, a long row of very upscale houses. I watched as he opened the garden gate at number sixty-three, strode up the path and let himself into the house. I stood staring at the house for several minutes, oblivious to the twitching lace curtains in the house behind me. I hadn’t yet spoken to the boy, but I was in love.
That night my dreams were consumed by the form of William. He was bent across a chair in the School Captain’s study at St. Tom’s, his grey school trousers clinging to his tight buttocks, while I whipped him with a sturdy ashplant cane. When I had been School Captain I was allowed, no indeed I was compelled by the culture of St. Tom’s, to beat other boys. I took no pleasure in beating the bottoms of small boys and by and large left such punishments to my deputy.
My taste was for boys of my own age. So it was that one day I required Bailey, a beefy captain of rugby, to present his arse for caning in my study. We were both eighteen at the time and until my reign had begun it was unheard for pupils of such an age to be beaten. Not so now. Bailey put up a minimum resistance. He knew the power structure of a school. I had it all, he had none. Had he refused my demand for him to put himself across the back of my armchair the consequences for him would have been disastrous. The headmaster would have been informed, a special school assembly called and Bailey would have been publicly birched. Bare arsed. Before his wounds had healed he would be driven to the local train station. Expelled.
So, with great resentment he presented his buttocks to me and I, in turn, laid six almighty stingers across the centre of his vast backside. Truth to tell, I got little satisfaction from this. I was developing an almighty fetish for beating, but my preference was for tighter more pert buttocks. Bailey, alas, had suffered in vain. My cock did not even twitch.
Not so with Altringham. He was altogether different. Altringham was a scholar, he spent his waking hours in the library, not on some sport field or other. He was also short and trim with buttocks that looked like two peaches in his tight school trousers. Altringham was intelligent and articulate; not always the best qualities for boys at public school. He proved his articulateness by being argumentative. Another definite no-no at St. Tom’s.
It came to a head one day when I had decreed that senior sixth-formers would be subjected to school rules like the younger boys. That meant a ban on smoking and drinking alcohol. The penalty for disobedience: Six. I was very satisfied with myself for I knew many of my colleagues were habitual smokers and drinkers. Soon, I would be sating my own appetite, for, I fully supposed, many were too addicted to stop.
I was surprised, and delighted, when one evening I was strolling by Main School when I espied Altringham under a chestnut tree, a lit cigarette between his lips. I had no idea he was a smoker. I should have thought a young man of his obvious intelligence might have found a more private place to smoke.
I took him back to my study. His usually pale face (too much time spent in the library) flushed as I berated him for his disobedience. Had he known of my instruction? He had. Had he known the penalty for disobedience. Yes, he agreed, he had known that too.
“You leave me no alternative Altringham; I shall beat you.” My heart raced at the prospect of flogging such tight buttock cheeks, my hand shook as I reached and took the ashplant cane from its place on the hat stand. I turned and wobbled the stick in front of Altringham’s face. It was then that I saw the glint in his eye. I would see similar glints in countless eyes over the years, but this was a first for me. Immediately, instinctively, I knew what that look meant. Now, I understood why my eighteen-year-old companion had been smoking a cigarette so openly.
A bead of perspiration covered his top lip like a moist moustache. I could see his eyelids flickering. I suspected his heart was beating as fast as my own. “Remove your blazer and place it on my desk,” I swished the cane for emphasis. With fumbling fingers, he undid his coat and slipped it off his shoulders. His white shirt was crumpled and I saw damp patches under the armpits.
He turned to face me. My eyes darted to his flat stomach and I tried to imagine what his cock might look like. I wished I had the courage to order him to lower his trousers, and perhaps, also, his underpants. I later discovered that I had I made such a demand Altringham would have stripped himself in a heartbeat.
Instead, I once again swished my cane, this time in the direction of a straight-backed wooden chair. “Bend over,” I intoned. I assumed Altringham had been caned before by a master – what boy at St. Tom’s had never been caned? Without hesitation, he approached the chair, halted a foot or so away from it and then standing at its front he bent over and took hold of two sides of the wooden seat. He shuffled his legs until they were about two feet apart and his back was arched, offering up his bottom to my ministrations.
I ached to get William in a similar position.
Now, that I knew where William lived and his school it would not be difficult for me to see him again. Getting to speak to him might be another matter. I was twenty-five years old and working in a solicitor’s office. After leaving St. Tom’s I went to university but without the incentive of ashplant delivered across the seat of trousers with some vim, my studies were poor and I left with an indifferent degree.
Mr. Crawley, an Old Boy of St. Tom’s, was senior partner at a law firm. The old school tie still meant something and he took me on. I was no more than a glorified office boy, but it allowed me to rent a furnished room and gave me a measure of independence from my father.
The old school tie had its advantages and drawbacks. Mr. Crawley had himself been School Captain at St. Tom’s more than thirty years before me. Like me, he found it difficult to shake off his schoolboy habits. So it was after the end of my first three months of employment, Mr. Crawley announced I should undertake a review of my work.
I sat in his darkly lit office, surrounded by piles of yellow legal papers. Mr. Crawley read from a written report he clutched in his hands. Who had written the report, I cannot say, since I do not know. It was a small firm of solicitors and Mr. Crawley would have been perfectly aware of my conduct and progress without requiring a fellow employee to write him a report.
Eventually, he finished his reading. It was not fulsome praise. Rather the opposite. He told me I showed little initiative and that I was mostly lazy. My timekeeping in getting to the office in the morning was dire and I was often late back from lunch. What did I have to say for myself?
I knew that tone of voice. I had heard it often enough in the housemaster’s study at St. Tom’s. Mr. Crawley carefully tidied the papers in his hand and placed them carefully on the shiny top of his desk. He steepled his fingers together and leaned forward, placing his face a few inches from my own. I saw the glint in his eye.
Had I been in his position I probably would have done the same. How would I resist the chance to whip a springy school cane into the stretched buttocks of a young man? If I had been on Mr. Crawley’s side of the desk, I would even as we sat staring at each other, be deciding exactly how I wanted the body positioned.
It came as no surprise to me when Mr. Crawley stood from his chair and shuffled around the desk and headed for the far end of the office. He paused at a glass-fronted bookcase. Below the shelves was a wide drawer. He bent forward, offering me the perfect view of his own buttocks. They were fleshy, as befitting a man who was probably in his sixties. They filled the seat of his grey-and-black-striped trousers. I imagined for a second that I held a heavy ashplant cane in my fist. I did not need to close my eyes to imagine the old man bent before me as I took aim and thwacked the rod across the middle of his bum. I crossed my legs as my cock pushed against my underpants.
Moments later, Mr. Crawley stood. He had a curve-handled rattan cane in his hand. He turned to me and swished it through empty air. He looked across the room at me. “Stand,” he ordered. Without hesitation, I did as instructed. He swished the cane once more toward the centre of the office. “Stand there.”
I took a deep breath and shuffled a couple of paces into position. I was not nervous and in no way surprised. I had no great enthusiasm for being beaten. I preferred to be the one doing the caning. But needs must. I had been caned many times at school, I had no fear. I would present myself as required by Mr. Crawley and let him take my arse off. Then, I fervently supposed, we could both get on with our lives.
Mr. Crawley took a small leather chair with wooden arms and swivelled it so that its back now faced me. I saw immediately that it was the perfect height for a young man to bend across. He tapped the seat of the chair. “Bend over.”
I paused, unsure if I should lower my trousers and possibly my underpants too. That might increase Mr. Crawley’s pleasure, I thought. I very much wanted to please him. My employer might have misunderstood my reluctance to move. “Bend. Now,” he said sternly. “Or there will be extra strokes.”
I lifted the tail of my suit jacket away from my buttocks and leant forward. The leather seat was old and cracked. It smelt faintly of perspiration. I shut my eyes waiting for the pain. I felt Mr. Crawley adjust my jacket and move it further up my back. Then he gripped the waistband of my black trousers and tugged. I felt the cotton material dig into the crack between my buttocks. Then, he whipped me.
I have withstood many beatings but I had never experienced anything like this. The first stroke connected with tremendous force across the middle of my cheeks. The crack echoed around the room. I was certain that Miss Winstanley, the elderly spinster woman who sat in reception, could hear. Of course, she could. But, I later supposed, I would not have been the first office junior to have shown Mr. Crawley his backside. Nor, would I be the last.
He gave me six stingers. He whopped the cane into me with great strength and enthusiasm. I shut my teeth and let him get on with it, determined not to make a sound. I had developed a high pain tolerance at St. Tom’s, I was certain I could withstand this.
He let me stand after Six. His eyes shone, as did mine, but for entirely different reasons. My backside throbbed like crazy. He had aimed low and I found it difficult to sit in any comfort for the rest of the afternoon. Three hours later, back at my lodgings, I was able to inspect the damage. There were six perfectly-formed welts, running across the underside of my cheeks. They had landed parallel to one another in a band no wider than two inches. Mr. Crawley was indeed an expert.
I rather hoped that someday, preferably sooner rather than later, I would be able to give William a similar thrashing. But, first I had to get his attention. I left Mr. Crawley’s office late one afternoon and headed through town to St. FIGS. I supposed William would be waiting at a nearby bus stop to make his journey home. Delight. I noticed him from some distance, even though he was among a group of boys. He always had presence. He stood out in a crowd.
I waited at an adjoining bus stop, staring. He was oblivious to me. The boys around him were much younger and he appeared to be on his own. I watched as he put his hand into his blazer pocket and pulled out a packet of cigarettes and a box of matches. He put the cigarette in his mouth, struck a match and lit it with some élan. He drew the smoke into his lungs. He looked around him as if looking for someone.
Did I see a glint in his eye? Perhaps, but honestly I was too far away from him to be sure. A prefect smoking, in public, in school uniform. I remembered a story I had read in the local newspaper. Dr Henderson-Smith, the St. FIGS headmaster, had a fearsome reputation as a flogger. It seemed hardly a day went by without some wretched boy visiting his study for a touch-your-toes session.
Surely, William would be spotted. The word would soon get back to the school. My heart thumped. Altringham. What delightful times I had with that smoker. A smile flickered across my face. Someone should report William. If not, perhaps I would call the headmaster myself. “A prefect, smoking at the bus stop,” I would inform him. It would not take much of an investigation. The senior boys would be interrogated one by one. Of course, William would confess at the earliest opportunity.
But, I supposed, what was the point of that? I wanted to be the one delivering the caning across the boy’s bum. Or at the very least I wanted to witness it. I would get no pleasure just knowing William had roasted buttocks.
The bus came. I watched William’s tight arse encased in pale grey trousers wriggle as he hopped onto its platform and, cigarette hanging from his lips, he climbed the stairs to the top deck.
Spring turned to summer and school ended. I could no longer hang around bus stops ogling the beautiful William. I am not particularly proud of what I did next. My only excuse was that I was madly in love – no, in lust – with the boy. I took to walking the street where he lived. The Avenue was in a leafy part of town. The back gardens overlooked a field which was lined with trees. It was purely by chance that I spotted that at least one was close to William’s home. I climbed it and to my utter astonishment found it gave me a clear view into my love’s bedroom. William could not have known he could be seen. Why would he expect someone to be hanging onto the branches spying at him?
It was a hot July and we had what passed locally for a ‘heatwave’. One afternoon I took up my usual position, legs akimbo across a large branch. His window was wide open and the curtains pulled back to allow maximum air into the bedroom. Oh joy! William was on his bed, nude except for a pair of black-and-white-checked boxer shorts. I was disappointed he was not naked: the boxers did not flatter him. He was on his back reading a magazine.
Then, someone I could not see came into the eighteen-year-old’s bedroom. William stopped reading and looked over to the person. He was having a conversation, or more truthfully, he was listening to somebody who was talking to him.
Then a big, rather fat, man came into my view. William moved as if trying to get away from him but the man who I assumed was his father grabbed him by the arm. In seconds the man sat on the bed and had pulled William across his knee.
I had a wonderful view of what happened next. William is face-down on the bed, his bottom over the man’s knees and his torso, arms and head are on the mattress, but his legs dangle in mid-air behind him.
William does not struggle as his dad pulls the shorts down to his knees. Then he whacks his palm into the boy’s mounds, slapping into his bouncing buttocks and the backs of his legs. Flesh wobbles with every smack. William takes it without histrionics – it looks as if this is not the first time this has happened. His arms are spread-eagled in front of him and he rests his cheek on the mattress between his arms. Then, he wriggles and looks back over his shoulder at this punisher, grimacing all the time. His body rises and falls over the man’s knees, and dad is pressing into William’s shoulder to keep him in place. But, William is not trying to escape; his movement are the natural consequence of the pain he is feeling from the spanking. He turns his buttocks to the left and then to the right in a kind of swimming motion.
It is all over in about three minute, the man tells him to stand up and leaves unceremoniously and William rubs his bare buttocks and jumps face down on the bed, grabs a pillow and buries his face in it. Then, he moves the pillow and places it beneath his crotch. I see William’s glorious buttocks, now a deep pink, rise and fall; rise and fall, as he humps the pillow. Within seconds he has shot his load.
My own dick was throbbing and I wanted to rip down my shorts and spit into the palm of my hand. I would have too, but suddenly I heard a call, “Spots, Spots!” A man walking his dog approached. His damn dog ran to the tree and cocked his leg.
I never returned to the tree. I took the man at his word when he said he would inform the police if he ever saw me again. For many nights after I took to masturbating at the thought of William’s bare-bottomed spanking. Only, in my dream I had taken the place of his father.
I needed to see the boy again. I recalled he worked at Rowley’s. I was desperate to talk to him and headed off to the High Street. I had not realised the shop did not open until ten o’clock so I sat in a nearby café and waited. William did not arrive. I returned the next day and then the next. Soon, back at my office, I found myself once again staring down at the cracked leather chair, a gentle breeze washing against my naked legs while Mr. Crawley put another six cuts into the crease where the buttocks met the thighs.
I was about to risk encountering the dog walker and stake out William’s home when I remembered that the one time I had seen the eighteen-year-old at Rowley’s was on a Saturday. Maybe, he only worked part-time. At about mid-morning I entered the shop. My heart thumped and my breathing was irregular. I had never been in a hardware shop before. I had no reason to. I was not the kind of fellow who worked with his hands. It was a large shop and cluttered with all kinds of wood and tools. I cannot be more specific, I genuinely had no idea what I was looking at. At the far end of the shop was a counter. I supposed if William were here, that’s where I would find him.
I had no plan. I supposed I would hang around pretending to be a customer and see if I might catch a glimpse of the delectable William. There were a few customers, all of whom seemed to know why they were there. I ambled around, hiding from the view of the counter, trying to peek at it from hidden position. Then I saw them. I stood rigid. Why was I so surprised? You had to be able to buy them somewhere.
In one corner discreetly stood a thin round metal container. Inside, standing on their stems rather like flowers in a vase, were a large selection of whippy school canes. They were of different lengths: some long, some short. And thicknesses. The heaviest were as thick as my little finger. They all had the statutory crook handle.
“Can I help you, Sir?” Startled, I turned and faced an elderly man wearing a brown protective coat. I blushed. Speechless.
“That’s alright Mr. Rowley, I’ll look after this customer.” It was William. He was dressed as I had fondly remembered him in pale grey trousers, a white shirt and navy blue tie. He smiled. I remember his eyes lit up. His face was tanned and he had the faintest outline of hair on his top lip. The rest of his face was shaved. I think the boy was trying to grow a moustache. How cute.
“Can I help you?” I swear he glanced at the can of canes, encouraging me.
My face in all certainty flushed. I smiled. “Which is the best?” I nodded at the canes.
“Well, Sir, that depends how naughty your young man has been.”
Unselfconsciously, I picked up a medium thickness cane. It was dark yellow and made of rattan. I had held similar canes before. Not at school; there we used ashplants; specially cut switches supplied by a fellow from the village close to St. Tom’s. He supplied the school and many fathers in the area. I replaced it in the container and choose a thicker specimen. It was identical to the one Mr. Crawley had used on me.
William reached into the bunch of canes. He did not speak as he rummaged around. He was seeking something. In a moment he found it. He withdrew a cane that was a little over three-feet long. It was a dark yellow colour and as he flexed it menacingly between his hands I saw it was both dense and extremely whippy. In the right hands it would deliver an almighty slash.
He pointed it at me. I saw the glint in his eye.
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More stories from Charles Hamilton II are on the MMSA website
Charles Hamilton the Second