The Junior Salesman

used drawing cane hold (4)

The Junior Salesman and other workplace whackings

THE TWENTY-YEAR-old junior salesman slowly unclasped his belt and unbuttoned his trousers. He pushed them over his hips and let go. From there they slithered slowly down his legs.

A breeze from the nearby open window brushed against his naked legs as he awaited the next command.

Tyler looked over at his boss; in his hands was a wicked-looking school cane, around three feet in length and with a curved handle.  Mr. Davenport’s huge grin exposed his decaying teeth as he tapped a pointon the floor in front of him with the cane, “Please bend over and touch your toes.”

 The Junior Salesman and other workplace whackings is another collection of my stories published in book form. It runs for more than 19,000 words and has many illustrations. You should be able to read it on your lap top or e-book reader.

Click on the link below to download it free-of-charge.


Picture credit: Unknown


Other books to download


The Dean of Dormitory Discipline and other university tales

Charles’ Picture Album

The Private Tutor

All in the Family. Tales of Domestic discipline


More stories from Charles Hamilton II are on the MMSA website

Charles Hamilton the Second

Mr Gregory, the Office Manager

z used cane longs adult office suit

Adrian chewed on his bottom lip and kept his eyes downcast on the carpet. He was not quite sure where to put his hands, so he let them hang loosely at his sides, then he clasped them behind his back the way a member of the royal family does. Lastly, he held his hands in front of his cock like a footballer defending a free kick. Then he started the routine all over again.

He could not get his eyelids to stop flickering; he was wracked with anxiety.

“You know why you are here young man.”

Adrian was not sure: was this a question, or a statement of fact? He decided a non-committal grunt would be enough of a response.

“Your work is sloppy. You make countless mistakes; you do not pay attention when you are working.”

It was quite a litany of complaints.

And there was more. “You are often late into work and back from lunch. You are often away from your desk for no good reason.”

Adrian listened as best he could. His heart was pounding so hard he thought it would burst through his chest. His breathing was becoming shallower and those damn eyelids would not slow down.

“I warned you before about your conduct, young man.”

Yes, Adrian silently agreed. Mr Gregory had warned him. More than once actually. There was nothing Adrian could say in mitigation. Everything his boss said was true. He was probably the worst accounts clerk in history. He had no aptitude for the job; no head for figures. Hey, he could not even add up properly.

It was a wonder to him how he ever got this job in the first place, but really he had no choice but to stick at it. Jobs were hard to come by these days and you did not readily give one up.

Mr Gregory eyed the accounts clerk. The boy’s clear skin was flushed pink; with embarrassment and also anxiety. His sparkling grey eyes were a little moist and hidden by his long curled lashes that refused to keep still.

“What did I say would happen if your work did not improve?”

Adrian’s pinkish face turned pillar-box red. He could not catch his breath.

“T..t..t…” he tried to respond but no words would form. His mouth was now as dry as the Gobi Desert.

Mr Gregory enjoyed the boy’s discomfort and his grey deeply-lined face cracked into a broad grin as he leaned forward in his chair.

“I’m sure you haven’t forgotten,” he cackled, his beaklike nose gave him the appearance of an eagle about to sweep down on the poor boy.

Adrian’s breathing, once shallow, now almost stopped completely.

“Well then young man let’s get this over with shall we.” Mr Gregory hauled himself from his padded chair and took a few steps across the room.

Adrian eyes followed the middle-aged man and his eyelids still worked overtime.

Mr Gregory sighed audibly and stooped down to reach the bottom drawer in an old-fashioned wooden chest.

Adrian closed his eyes tight: knowing instinctively what his boss would withdraw from it.

“Here,” Mr Gregory straightened himself and turned towards Adrian. “I said if your work did not improve I would cane you.”

Adrian was transfixed. His cruel ugly boss held a long yellowish-brown stick between his hands.

Mr Gregory was very proud of his cane. He fondly imagined it was just like hundreds that were used every day by schoolmasters to whack the stretched backsides of naughty schoolboys.

He wobbled it in front of Adrian’s face, hoping to intimidate him. He succeeded.

The rod was a little over three feet in length, about the thickness of a pencil and with the traditional curved handle at one end.

Through half-closed eyes Adrian watched apprehensively as Mr Gregory slashed the springy rod through thin air.

This was not the first time Adrian had seen such a cane. He had been on the receiving end of one many times at school for general laziness and misbehaviour. Adrian had been raised to believe a thrashing with a cane was a just punishment for wrongdoing. He knew he had screwed up at work and he had been warned of the consequences if he did not improve. He really did not have anything to complain about, but it was a little strange to have to show his backside to his boss. Adrian had thought he had left all that behind at school.

Mr Gregory whipped the cane through the air one more time. Seemingly satisfied that he now had the measure of the rod, he pointed it at his desk.

“Take off your jacket and put in there,” he swished one more time for emphasis.

Mr Gregory watched intently as Adrian with fumbling fingers undid the button of the jacket of his dark grey suit and slid it over his shoulders, uncovering his gleaming white shirt. With his dark blue striped tie and dark grey trousers he could be mistaken for a senior pupil at any of the local schools.

Mr Gregory drank in the sight of Adrian’s muscular shoulders and slim flat stomach as the boy carefully folded the jacket and placed it on the desk. He was so unlike many of the other boys in the office, still in their teens but already running to fat with middle aged spreads around their waists.

Another swish of the cane told Adrian it was time to prepare himself.

“Take that chair and turn it round so that the back is facing you.”

Although Adrian was no virgin to the sting of the rattan cane, he still did not relish the ordeal he was about to face.

Sorrowfully, he gripped the large padded leather chair and in one movement swivelled it round into position.

Another swish of the cane, this time directed at a spot on the floor.

“Stand there young man.”

Adrian shuffled forward and stopped.

“Closer!” Mr Gregory was impatiently anxious to get started. Adrian, however, was quite keen for the action to be delayed.

“Bend over the chair!” It was a curt command devoid of emotion. Mr Gregory had to perform his duty.

Adrian hesitated, gripped by the absurdity of the situation. Here he was a nineteen-year-old man expected to bend over the back of an armchair to offer up his arse for his miserable boss to whack with his cane. But there was nothing he could do about it; Mr Gregory was in charge.

For the first time that afternoon Adrian caught Mr Gregory’s eye; was his boss just a little embarrassed too? He could not tell.

Swish! “I shan’t tell you again.”

Adrian hesitated no longer; if he wanted to keep this job he had no choice. He took a deep breath, rubbed his hands together, took a pace forward and swiftly fell face first over the back of the chair.

“Bottom higher, legs further apart.” They were unnecessary instructions for Adrian’s bottom was already perfectly positioned to receive punishment. And what a trim bottom it was, much admired by the girls in the company and, if only Mr Gregory knew, by a surprising number of men as well.

Mr Gregory took up position about three feet from Adrian’s left buttock, before carefully rubbing the springy cane across the very centre of the boy’s globes. Tap, tap, tap, it went. Mr Gregory heard Adrian hold his breath in anticipation of the first agonising cut that would soon slice into his bottom.

Slowly, Mr Gregory raised the cane about four or five feet above the boy’s taut bottom and then with an almighty swing he slashed it down across the very centre of the target area.

A gasp of air whistled through Adrian’s clenched teeth, as a burning stripe seared into his tight cheeks. Instinctively he gripped hold of the foam padded seat cushion and let the pain course from his rear end up and down his stretched legs.

“Owww!” he could not help himself. He had determined not to show Mr Gregory any emotion, but this first stroke was worse than anything he had ever been forced to endure at St Simeone’s School.

Mr Gregory admired his handiwork. Yes, he smirked to himself that one had really hit home.

He raised the cane once more and positioned it a half an inch below the first cut. Again he gave the swing all his strength. The cut hit Adrian’s pert buttocks at speed, sank a little into what flesh there was on the boy, and bounced back with vim.

Adrian screamed like a stuck pig. Still gripping the cushion his back arched and his feet stamped up and down. Never in his entire life had he felt such agony. To say it felt like a white hot poker had been pressed against his skin would be an understatement.

The boy’s face, usually so clear and a little pale, was now puce. His beautiful grey eyes were drowned in tears.

He wanted desperately to plead for mercy. He would do anything for Mr Gregory. Anything at all. He would concentrate on his work, go to night school to learn accounting; buy himself an adding machine. He would be the best-ever accounts clerk that ever lived, if only Mr Gregory would stop hurting him.

“Yowllll! Oh my God!” The third struck diagonally across the other two, setting both on fire again. The howl that surged from his throat was so deep; Adrian thought he would vomit at any moment.

Mr Gregory spluttered and coughed. His body convulsed one way and then another.

“Urgggh” he was woken by a cold damp patch across the front of his pyjamas.

Miserably, he wriggled the pyjama bottoms over his buttocks and down his legs, before throwing them from under the bedclothes onto the floor. Then he rolled across to the empty half of his bed and tried to resurrect Adrian and those trim buttocks that still had to endure three more strokes from Mr Gregory’s cane.

The next day was Saturday so there was no work. Mr Gregory got up at eight o’clock, bundled his soiled pyjamas together with the bedsheets and the rest of his laundry into the washing machine, picked up his keys and left the house.

He was a creature of habit and just like every day, he shuffled down the street to the newsagents. It was still early and the street of small semi-detached houses was almost deserted. Couples were still snuggled together in bed, enjoying what was euphemistically called a ‘lie-in.’

It was June and the day was already heating up. There had been a heatwave for days and the forecasters said there was much more to come. At the newsagent, as he did every morning, he nodded a cursory “good morning” to the silver-haired lady behind the counter. He had been to the shop every day for ten years and still did not know the lady’s name. Somehow she knew his. Almost.

“Good morning Mr Gregson,” she smiled the way that small shopkeepers, eager to ingratiate themselves with customers, always did. He handed over some coppers and took his copy of the Daily Express. On weekdays he would then proceed on the five minutes’ walk that took him to his office, but on Saturdays and Sundays, he went in the opposite direction and made his way to Joe’s Café.

Mr Gregory had lived in Tylesbury for more than twenty years. It was what was still called a ‘new town.’. It had been built in the 1950s to house people cleared from the slums of London. Tylesbury was full of bright little homes for people to live in and factories and offices for them to work at. It was a socialist vision for the future.

His was a mundane life. He was born in Bethnal Green, which despite its promising name was not a rural paradise. It was a poor area of London near the docks and heavily bombed by the German Luftwaffe. He left school aged fourteen and drifted aimlessly from job to job. Kids did in those days, there was plenty of work and nobody had much care for the future.

He did his National Service in the Royal Air Force. It was in the Pay Corps so there was not much glamour in that. For the first time in his life, Mr Gregory found he was good at something. Unlike the wretched Adrian of his fantasies, Mr Gregory was well-organised and meticulous. When he was demobbed he fetched up at Mega Fastenings on the Herbert Morrison Estate in Tylesbury and he had been there ever since; making his way from general clerk to the exalted rank of Administration Manager.

The café was not busy at this time of day. It did most of its trade during the week, servicing workshops and offices. Mr Gregory liked it that way. He sat at his usual table and ordered his usual meal (full English breakfast) and settled down with his paper.

Nobody took any notice of him and he took none of them. He scanned the paper with no real interest. It was the usual stuff; economic downturn, a murder in London’s gangland and politicians droning on about how bad members in opposition parties were. There was a General Election due and they could expect a lot more of that before polling day.

Then he turned a page and saw something that made his juices drool. He slammed shut the paper as the café owner came and set his meal down on the table. Mr Gregory hoped the man had not seen the story that had caught his eye. He would not want people to know he was interested in that sort of thing.

With the café owner safely back behind his counter, Mr Gregory surreptitiously opened the paper. He read the story through quickly, then took a mouthful of sausage from his plate and chewed contemplatively as he savoured every detail of the story once again.

There was a school in a town he had never heard of. A right posh school by the sound of it. What happened was that the boys had been complaining about the heatwave. They were sweltering in their traditional school uniform of woollen blazer and long trousers. The older boys, some were as old as eighteen, said they wanted to be allowed to wear short trousers. The younger boys were obliged by the school to wear shorts up to the age of fourteen whatever the weather.

When the older boys demanded the right to wear short trousers their headmaster told them flatly: No. But, they rebelled and a group of them turned up dressed in their smart grey flannel short trousers anyway.

The headmaster went ballistic. They had broken the rules and defied his authority. There was only one course of action. They were lined up outside the headmaster’s study and one by one they were ordered inside.

Mr Gregory read with mounting excitement, ‘One eighteen-year-old sixth-former, who did not want to give his name for fear of retribution, said: “When it was my turn to go in the headmaster instructed me to bend across his desk. He then administered six hard whacks with his cane to the seat of my trousers.

‘“It hurt like Henry.”’

‘Another boy said: “It’s not fair. We weren’t asking to wear beach shorts. We would be happy to wear the same type of grey flannel short trousers the younger boys wear all the time.”’

Oh, how Mr Gregory envied that headmaster. That was the job to have, he thought.

He gulped down more of his breakfast as he read more of the story. Later, the headmaster rounded up three of the ringleaders and he publicly thrashed them in front of the whole school, even though they had already been beaten in the privacy of his study.  And, oh glory! He gave it to them on the bare buttocks.

Mr Gregory’s heart sped. He read the story for a third time and then sipped gently on his tea. Tylesbury had its own posh school, called unimaginatively Tylesbury School. It was an independent grammar school, a kind of private school. The pupils were made to attend lessons on Saturday mornings and he often saw the older boys looking delicious in their bright blue striped blazers and long light grey trousers hanging around the shops in the afternoon after classes had finished. Some of those boys looked very dapper and eminently spankable.

The dreams he had about them would be enhanced greatly, now that he could picture them in their tailored short trousers each in turn knocking on the heavy oak door of Mr Gregory’s study, waiting for the gruff “Come!” from within as their instruction to enter.

Mr Gregory would be waiting in his oak panel-lined study, dressed in his swishing academic gown, a mortar-board cap, the one with the tassel hanging down, planted firmly on his head. To the consternation of the boys, he would be flexing his whippy cane between his hands.

There would be a curt command, “Bend over, touch your toes.” Mr Gregory would roll the boy’s blazer up his back clear of the target area and then thrash six almighty swipes into the flannel-covered buttocks. It would not matter how much the boy yelped, he would get the full six.

Then, “Stand up. Send in the next boy.” And one boy would be replaced by another as headmaster Dr Gregory did his duty and ensured the next generation of gentlemen understood the virtue of obedience.

Carefully, Mr Gregory tore the page from the newspaper. It would join his growing collection. In his spare bedroom at home, he had a tin box that he always kept locked. Inside was a sheaf of cuttings from newspapers and magazines. The box was inside a suitcase (also locked) on top of his wardrobe.

This would become one of his favourites, for sure. Others that he liked to take out and read again and again were about an approved school for juvenile offenders that was closed down the previous year after a government inquiry. They said there was inappropriate use of the cane. Inappropriate? At least no boy there got it across the bared buttocks.

Another favourite concerned two eighteen-year-old sixth formers. There were some young rabbits that were caged up ready to be used by the pupils in science lessons. The boys took the rabbits down to an open field and set them free. That cost them three strokes on the backside.

Mr Gregory wondered why that was considered newsworthy by the Daily Express, but he was grateful nonetheless to add it to his collection.

Breakfast over, Mr Gregory set off on the next part of his Saturday routine. Shopping at the new large self-service supermarket had become a pleasure in recent weeks after he discovered a young assistant called Phillip.

He knew he was called Phillip because all the staff wore name tags. He supposed it was to make customers feel they were getting personal service, as they had done before the large stores drove most of the small shops out of business.

You would not give Philip a second glance if you saw him coming towards you in the street. He was smaller than average, with a pock-marked face, developing jowls and an overbite. But if you saw him walking away you would be captivated by his exquisite buttocks. They were like two pimples inside his loosely fitting black trousers, inviting close inspection from connoisseurs of the male form.

Mr Gregory first saw him in the dry goods section of the supermarket. The old man turned from one aisle into another and quite literally stopped in his tracks. There at the end of the aisle was Philip, his back to Mr Gregory and bending down to put packaged goods on to the bottom-most shelf.

Mr Gregory’s tongue might have hung out, or his face might have blushed scarlet with desire; either way he was immensely conscious of a woman standing close by looking at him in a strange manner. He turned on his heels. He must get away and he must do it quickly.

But the temptation was too much for him. Only a few seconds had passed before he retraced his steps and stood once again at the end of the aisle admiring the vision in the black trousers before him.

Slowly, pretending to have great interest in the cornflakes and other breakfast cereal on the shelves, he inched his way down the aisle, fearful that at any moment the boy would straighten up and go away to another task.

Mr Gregory reached Philip and stood by the boy’s side. Unconscious of the stir he was causing, Philip continued to rearrange the packets on the bottom shelf. The boy’s knees were straight and his body bent. Mr Gregory was so close he could touch him. He had never been so close to a bending boy. It was as if he were submissively presenting his bottom to Mr Gregory and saying, “I’m sorry Sir, I have been a naughty boy, please spank me.”

He was so close he could put his hand in the small of Philip’s back, hold him steady and smack his palm down into the boy’s tiny, but perfectly formed buttocks. His ungainly hand was the size of a shovel and could almost fit across both buttocks at once.

The old man first approached the boy from behind, then covertly moved to the side to take in the full view of one of Philip’s curved cheeks. Mr Gregory raised his hand ready to strike.

Quickly, catching himself before he disgraced himself, he turned away ashamed and almost bolted to the other side of the store. Safe among the dairy cold counter he paused to catch his wind. The sight of Philip’s backside, seemingly offered submissively for a spanking, had literally taken his breath away.

His attempt to continue with his shopping as usual was frustrating. Did he need sugar, how many eggs did he have a home? None of this mattered any more. All he wanted to do was to return to dry goods and stand once again by the boy in the black trousers.

Trying not to be obvious he meandered around the aisles, seemingly haphazardly, but, like a marine on manoeuvres he was headed for one destination only. At last he was in the adjoining aisle. He was wheezing. Why? There had been no physical exertion. It was a sedate journey from one end of the store to the other.

But he did know why but could not admit it, not even to himself. He wanted that boy. He wanted him bent over before him touching his toes, asking, no demanding, that Mr Gregory beat his buttocks black and blue.

Then, but only when Mr Gregory gave the order, Philip would rise and very slowly and deliberately peel down his trousers, before in one fine athletic movement, once again bending forward knees straight, fingertips on his toes, offer up his bum again, this time wrapped in the soft white cotton of his underpants.

There would follow a bottom scorching whacking. Mr Gregory thought one of his old worn bedroom slippers would do the job very well. Two, no three dozen, whacks across those tight cheeks would do it.

The boy would take it bravely. There would be no howling like a hyena. Instead the punishment completed the boy would gaze into Mr Gregory’s eyes lovingly. “Thank you, Sir,” he would say, “I thoroughly deserved that.”

“Yes you did,” Mr Gregory would reply, “and if I have to deal with you again, make no mistake you will get it with your trousers and your pants at your ankles.” And then for emphasis, he would add, “On your bare bottom.”

His mouth dry and his tongue almost hanging out, Mr Gregory turned into the aisle to drink in the sight of the wonderful boy who had become his imaginary spank slave.

But, he was not there. In his place were two middle-aged ladies discussing the merits of instant porridge.

Oh no! Where could he be? In distress Mr Gregory darted from aisle to aisle, bumping into housewives going about their lawful shopping.

“Hey! Where’s the fire!”

“Will you watch where you’re going!”

No, he would not watch where he was going. All he cared about was finding Philip. He must be in another aisle, filling shelves. Somewhere on this supermarket floor, he was bent over straight knees, straight back. Showing off his perfect, spankable bum.

He searched in vain and then calming a little he completed his shopping. He must stop making a fool of himself, he admonished himself. You deserve a damn good spanking yourself, what disgraceful behaviour, and in public too.

Waiting his turn at the check-out he once again saw Reginald. Reginald was some kind of store supervisor and wore the cheap mid-blue suits the company made them wear to prove it. He could not be much more than twenty-one, twenty-two maybe, Mr Gregory had supposed.

He was tall, fair and rather chubby. Mr Gregory fell in hate with the young man the first time he had seen him, two weeks previously. It had been a small matter. A loose cap on a sauce bottle. It had not been noticed until the customer was ready to pay. Reginald intervened. A shop assistant was called, an elderly man, and directed to go fetch a replacement. You would have thought the man, who was old enough to be Reginald’s grandfather, was his personal slave.

“And be quick about it!” he ordered as the old man scuttled off.

Reginald was far too young to be a boss. He had no idea how to treat people properly. The way he spoke to the shop assistant was disgraceful; he was far too haughty. For nine pence Mr Gregory would throw the wretch face down across one of the counters and thrash his fat arse to pieces with a cane.

Right in front of ‘his’ staff; that would bring him down a peg or two.

Mr Gregory had a fitful sleep that night. Philip, oh Philip! He dreamt of him so often, He was naked and bent submissively across his knee. With his left hand Mr Gregory ruffled his hair, to let him know he was loved. His fingertips caressed his back as he followed the spine from the boy’s neck to the hairless crack in his buttocks. Mr Gregory’s right palm hovered above each cheek, and then with a circling motion, massaged them gently.

The boy breathed easily; he was submissive and ready for what he was about to receive. Mr Gregory raised his right hand to shoulder height and brought it down with a hearty SMACK! into his right buttock. He felt it, it smarted, and his bottom started to glow. He smacked him twelve times, slowly, so that his creamy white bottom turned to bright, bright red.

Then there was the time Philip was in school uniform, bending over, touching toes, as Mr Gregory smacked a gym shoe into the seat of his stretched grey Terylene trousers. Philip was across his knee as a soccer player for a spanking on the shorts (in the days when they still were ‘shorts’). Then dressed only in swimming trunks (he had been in the sea beyond the ‘danger line’) he was whacked (for his own good, of course) on his soaking wet bare arse.

Mr Gregory’s favourite was the boy in those lovely trousers bent submissively across the check-out counter for him to be thrashed with a traditional whippy crook-handle rattan school cane.

There was a timid knock on the office door. Mr Gregory’s looked up from his paperwork, expecting the door to open and his unexpected visitor to enter. But, nothing happened. The old man returned to his list of figures; perhaps he had imagined it. He was finding it hard to concentrate. There was a lot of noise from traffic on the estate that morning. And, his temples were throbbing a little.

Tap, tap. No, it was definitely a knock on the door.

“Come in,” Mr Gregory was surprised how hoarse his voice sounded. It was Monday morning and he had rather overdone it the night before, demolishing one bottle of whisky and starting on a second.

The door edged open slowly and it seemed like an age later when a young head with shaggy light brown hair poked around. Beneath the shock of hair was a cherubic face. Mr Gregory took in the vision: hazel green eyes, tanned, almost glistening skin, a firm chin and the cutest button of a nose the old man had seen in many a long year.

“Come in, come in,” Mr Gregory tried joviality, but his alcohol-fuelled headache turned his intended warm smile into a threatening grimace.

He could see the young man blanch; his eyes darting down to the floor.

Someone had to break the silence. Mr Gregory assumed as he was the boss it had better be he.

“Can I help you?” Again the attempt at warmth failed dismally.

The boy startled. “I’m the new work experience boy,” he blurted in confusion and even with the deep sun tan Mr Gregory could tell the boy was blushing.

“Oh, yes of course.” Now, it was Mr Gregory’s turn to sound confused. He knew the boy was coming. Mega Fastenings took two business students each year from the polytechnics. They stayed for a year, a sandwich course they called it. He had a file on the boy somewhere; what had he done with it?

“Craig. Craig Weston” the boy’s nervous smile was really rather scrumptious, Mr Gregory thought as furtively he ran his eye over the boy. Oh, yes, he thought, a definite improvement on Ian, the intern who had just left the company to return to his college. You will do very well.

Mr Gregory was practising his small talk with the office staff. He had been on a course. Say nothing of any consequence, nod repeatedly and smile a lot: that was the gist of it.

There were two easy chairs in the office but the boy did not have the confidence to sit uninvited. Instead, he stood in front of Mr Gregory’s desk, his hands clasped awkwardly behind his back.

“So this is your first morning?” Mr Gregory started on the small talk.

“Yes, Sir,” Craig replied, still not quite able to look Mr Gregory in the eye.

Sir! Yes, Mr Gregory liked that. He also very much liked the way the teenager was standing, awkwardly in front of him. He felt a fantasy coming on. It was a sweltering hot day, but Craig had dressed formally for his first day. He had left his jacket behind, but wore dark grey trousers, a plain shirt and a striped tie.

He supposed it was the kind of thing office workers wore. It was, but in Mr Gregory’s imagination it was a school uniform and Craig was a very naughty boy, sent to the headmaster’s study to be dealt with.

He could not see Craig from behind, but if what was on show in the front was a guide, he would look fabulous draped over the back of a low easy chair; or maybe even better, stood in the centre of the office, feet apart by a yard or so, bent over, knees straight, fingers stretching into the toes of his shoes.

Mr Gregory asked more inane questions but did not listen to the answers until, “So I have nowhere to live at the moment.”

Mr Gregory came back to earth. “Oh, so where did you stay last night?”

Craig gave the name of a local ‘hotel.’ Mr Gregory was not sure if the called itself a hotel, but if it did the new Trade Description Act would soon put a stop to that. It was a place for down-and-out tramps. It was entirely unsuitable for such a good-looking boy.

“But, I am looking for something else,” Craig trailed off.

It was an hour or so later that a germ of an idea lodged in Mr Gregory’s mind. It might work, he thought. Why not? He should take more initiative.

He had a spare room at his house. Craig could stay there. Why not? There might be gossip; he did not want the neighbours to get the wrong idea. Maybe, just temporarily then, to get him out of the doss house; until he found somewhere more suitable.

The heat, his self-inflicted headache and this wonderful new idea he had, was too much. He needed fresh air.

He fleshed out the plan as he slowly walked the length and breadth of the industrial estate. There would have to be rules of course; a curfew, keep the house tidy; set times for watching TV and so on.

He could see it now. It is a sweltering hot afternoon: will this damn heatwave never end? Craig is sprawled on the sofa in the living room glistening, dressed only in skimpy satin running shorts and a singlet. Mr Gregory enters.

“What are my rules about smoking in the house?”

Craig is startled; he did not know Mr Gregory was at home.

“What are my rules?”

“Eh …” Craig knows the rules and that he has broken them, but he will not give in without a fight.

“But, it was only in my room,” he says a little too defiantly.

“What are my rules?”

Craig flushes. He is in big trouble and he knows it. Mournfully, he replies, “No smoking.”

“Yes, no smoking. I’ve spoken to you about this before.”

Sorrowfully, Craig nods assent. Yes, he has been told. There is no excuse.

“And you have been told the sanctions.”

Craig gulps. No, surely not. He had not meant it, had he?

Mr Gregory strides further into the room. “You know my methods. Stand up.”

Craig flinches, trying to sink further into the padded cushion of the settee.

“Come here,” Mr Gregory reaches forward and grabs the boy by the left arm. He gives little resistance; he is scared but instinctively he knows he cannot get out of this. Matters have to take their course.

Releasing his grip on Craig’s arm, Mr Gregory snatches a clump of his unruly hair and pushes him face down over the back of the armchair. The boy’s singlet rides up his back revealing an expanse of golden tanned flesh.

Mr Gregory grabs at the elastic waist of the provocative shorts and they are soon at the boy’s knees: followed by his underpants.

Craig seems resigned to his fate. He whimpers a little, his now bared bottom twitches as he hears Mr Gregory unbuckle his belt and remove it through the loops of his trousers. Then he doubles up the wide, thick, heavy leather belt and brings it crashing down across the centre of Craig’s bottom.

In a frenzy Mr Gregory puts six sunset stripes across the boy’s cheeks.

“Ow, ow, ow,” he wails. “I’m sorry Mr Gregory. I won’t smoke again. Ow! Ow! Ow! Please let me off!”

But, Mr Gregory carries on lashing.

“Nooo! Please,” the wailings and pleading continues.

“Be quiet. You deserve this. You’ve had this coming for a very long time.” Sweat is pouring from Mr Gregory as he raises the belt again and again, swiping it down into the upturned buttocks.

“You miss curfew, your room is a disgrace, you smoke in my house.”

“Please! I’m sorry! Please,” the pleading continues, but so also does the bare-arsed leathering.

Maybe, Mr Gregory reflected that evening, as he poured himself more whisky, it was for the better that Craig had found a room with the Rev Crick at Aston Budleigh where Ian used to lodge.

Back at the office Mr Gregory was on tour. He did this every day; he had been taught to do it on a management course. Be seen by the staff, stop and chat for a minute, let them know you are there. Mr Gregory was not a natural ‘talker,’ but he practiced a lot.

He loved walking through the offices of Mega Fastenings; it gave him the excuse to ogle the boys’ backsides. The office was pretty typical of its type there were upwards of 250 employees; many women with families; one or two older men; but mostly younger boys and girls in their teens and twenties.

Most days Mr Gregory would find Adrian working busily at his desk. Adrian was not an accounts clerk in real life; he was a general administrator in the order office. Mr Gregory had no idea if Adrian was good or bad at his work. He rather suspected he was good, he always seemed to be hard at it when Mr Gregory passed by.

Once, Mr Gregory had tried to talk to Adrian; to chat, just as the management course had instructed. Which of them had been the most shy? Mr Gregory reflected sullenly that evening. The boy blushed scarlet as if he had been caught in some naughtiness when his boss stumbled over an inane question.

It was not a meeting of great minds, but that night as he lay in bed his head spinning, Mr Gregory as he always did, went through the activities of his day, trying to focus on a moment that he could turn into a fantasy. He tried to conjure up Adrian, but instead got Robert and Pat.

Pat was a forty-something mother with the figure of a woman who had delivered four children. Advertisers had started saying such people had the ‘fuller figure.’ Mr Gregory arrived at the section of the open-plan office given over to purchasing in time to catch the tail end of a conversation.

Pat was cheerfully berating Robert, a twenty-something clerk.

“I should take you cross my knee, but you’d probably enjoy it!”

“Ha!” Robert replied backing off and returning to his work station, “You should be so lucky.”

What did it mean? Mr Gregory flushed and walked on pretending not to have heard.

Would she spank Robert. Across her knee? He was a burly lad, a rugby player type. She would have her work cut out forcing him face down.

But, what if he submitted himself to her.

“I’m sorry Pat. You’re right. I do deserve a spanking.” And then he prostrates himself across her lap. His chubby bum in the air and his sweaty face staring down at the hard nylon floor covering.

What would she do? Would she smack the palm of her hand into his tight bulging trousers?

No, Mr Gregory supposed, she would have a hairbrush in her drawer, that would be a perfect weapon. She could whack that with great vigour into his fat arse. Even with his trousers and pants on he would feel it.

Why had she threatened to spank Robert? Back in his office, breathing heavily, Mr Gregory cannot get the image of Robert out of his mind. What had he done? He should be told, he is the boss. It is his job to enforce discipline, not Pat’s. He should call the boy into the office right now and deal with him.

Mr Gregory sat behind his desk and stared intently at the space between it and the door. Mr Gregory is sat on a wooden straight backed chair. Robert stands in front of him, crestfallen. The boy’s hands are trembling. He knows he has done wrong. His boss has found out and now he must face the inevitable discipline.

Mr Gregory grips a stout wooden ruler. It is only twelve inches long by an inch wide, but it is half and inch thick and made of solid wood. It packs one heck of a punch when lashed down with force across a boy’s bared bottom.

Mr Gregory’s instructions are calm. “Take off your jacket and place it on my desk. Then please lower your trousers and underpants.”

Robert hesitates, but not for long. There is nothing he can do. He has broken the rules and he must be punished.

Not daring to look at Mr Gregory, sitting, legs splayed, back straight, sweat patches forming under his armpits, Robert unbuckles his belt, pops the button on his trousers and unfastens the zip. The weight of the bunch of keys in his pocket makes them hurtle to his ankles. Then he puts his thumb in the waistband of his pants and with the merest flick of the wrists he sends them to his knees.

His shirt is long and covers most of his manhood and buttocks. Mr Gregory affects a lack of interest that he does not feel.

“Lift up your shirt and bend over my knee.”

This is the first time that Robert looks at his boss. Has he noticed before how old and ugly the man is? His skin is pale grey, even in the height of the heatwave, the deep lines cut across his face; the beak of his nose reminds Robert of a witch in a fairy tale.

With his shirt lifted and buttocks and genitals duly exposed, Robert flops forward, his considerable weight taking Mr Gregory by surprise. Robert is not as lithe as Adrian and his buttocks are huge and flabby.

Mr Gregory is fascinated at the way the narrow heavy ruler sinks deep into the fleshy globes, before emerging, leaving behind deep pink stripes against the whiteness of his flesh.

Mr Gregory works methodically; no inch of the vast buttocks is left unscathed. Robert remains impassive, enduring the increasing pain. His bottom starts to tingle and this turns to real pain. His bottom is getting hotter and hotter. Ouch! This is real, not like when Pat spanks him.

The phone rings. Robert dissolves.

Adrian lumbers up the stairs towards his bedroom, the scolding words of Uncle Gregory still ringing in his ears. Already tears are welling up in his sparkling grey eyes and uncle has not even started yet.

“Hurry up, be quick about it!” Uncle Gregory is standing outside the living room. Adrian quickens his pace. Inside the bedroom, sorrowfully, Adrian looks at himself in the mirror. “You’re for it now, me lad!”

His face is wringing with sweat: the damned heatwave mingled with the boy’s fear. His deeply tanned face anxiously stares back at him. “Oh well, I’d better get on with it.”

In one movement he pulls his loose fitting shirt over his head, revealing a nut-brown chest. Then down come his shorts.

His tight bright green micro briefs hug tightly, bulging at the front. Some hair is poking out over the top. Adrian is no longer a little boy.

Should he keep his pants on? Would Uncle Gregory notice?

“Who am I kidding?” Adrian talks to himself in his head. He knows what Uncle Gregory has in store for him; underpants will not be playing a part in the action. He whips them down, releasing his cock and balls.

His pyjamas are tucked neatly under his pillow. He loves these pyjamas; he hunted in shops all over town for them. He steps into the grey-and-white striped bottoms, and pulls the long white drawstring tight before tying a perfect bow. The pyjama jacket is just a little bit too big; the sleeves reaching halfway down the palms of his hand.

Dressed, he turns once again to the mirror and sees the image of a small boy reflecting back at him. Ready, he leaves the room and trudges down the stairs to face Uncle Gregory.

Uncle Gregory has prepared a dining room chair which now dominates the centre of the room.

Adrian shuffles in and stands facing his uncle. He knows the drill; he has been through this many nights before.

Uncle Gregory loosens and then removes his tie, before taking hold of the cuff of his right shirtsleeve and slowly rolls it up to his biceps, all the while rebuking Adrian.

“I told you if I got any more complaints from school I would give you a damn good spanking.”

It was true. Many times, his uncle had made the promise, and now he would deliver.

Adrian’s eyes flicker wildly as his gaze follows his uncle across the room. He stoops and retrieves a bedroom slipper from a shelf under the television set. Fully armed, he walks over to the chair and plonks himself down.

“Come here.” Uncle reaches forward and takes Adrian by the left arm and pulls him forward. He does not need much force, Adrian is not resisting. The boy has been raised well. He knows rules are rules and if he breaks them he gets punished. And, in Uncle Gregory’s house that means a spanking.

Adrian cannot stop his eyelids fluttering. His breathing becomes laboured and he can feel the blood rushing to his face as the moment draws nearer.

Uncle places the slipper on his lap and with two free hands he sets about untying the perfect bow. Once done, the pyjama trousers fall of their own accord down to the boy’s knees.

“Bend over.”

Adrian closes his eyes tight, takes a deep breath and gently eases himself into position, wriggling a little until he is comfortable. Both his palms rest flat in the deep pile carpet, his knees are straight and his toes hover an inch or so above the ground.

Silently, Uncle Gregory prepares the boy. Adrian feels him take hold of the tail of the over-large pyjama jacket and drag it half way up his back. Now, naked from the shoulders to his toes, Adrian feels a very slight breeze cooling his bare flesh.

He cannot help himself as he instinctively clenches his buttocks in protection against the expected onslaught.

“Relax boy, relax.”

Adrian tries, but fails to release the tightness in his cheeks. He tenses more when Uncle Gregory caresses his huge bony hand across the boy’s soft tender cheeks. His heartbeat races and for a moment Adrian is certain he will faint.

Adrian feels a movement in Uncle Gregory’s body as his right arm is raised and he prepares to bring the slipper crashing down into the pert naked buttocks offered up to him.

Adrian twists and turns as sweat pours from his body soaking the bedsheet beneath him, his raging hard-on ready to explode. Something is disturbing him.

An ambulance rushes by the window, siren blaring, on a mercy mission.

Picture credit: Unknown

This story was first uploaded in October 2015.

Other stories you might like

Their new house

The missed curfew

The glorious summer


More stories from Charles Hamilton II are on the MMSA website

Charles Hamilton the Second

BOOK. The Junior Salesman

used drawing cane hold (4)

The Junior Salesman and other workplace whackings

THE TWENTY-YEAR-old junior salesman slowly unclasped his belt and unbuttoned his trousers. He pushed them over his hips and let go. From there they slithered slowly down his legs.

A breeze from the nearby open window brushed against his naked legs as he awaited the next command.

Tyler looked over at his boss; in his hands was a wicked-looking school cane, around three feet in length and with a curved handle.  Mr. Davenport’s huge grin exposed his decaying teeth as he tapped a point
on the floor in front of him with the cane, “Please bend over and touch your toes.”

 The Junior Salesman and other workplace whackings is another collection of my stories published in book form. It runs for more than 19,000 words and has many illustrations. You should be able to read it on your lap top or e-book reader.

Click on the link below to download it free-of-charge.


Picture credit: Unknown

For more free-to-download books click here

The boss’s son

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People round here think because I’m the boss’s son I’ve got it made. In a year or so I’ll be on the Board and raking in the profits from all their hard work. I wish it were true. If they only knew the half of it.

Dad is a self-made man. He worked from the age of fourteen on a barrow in the street market and hauled himself up by his bootstraps. Or, so he’s always telling me. But the past is a foreign country; you couldn’t do something like that today. The self-made men (and women) of today are all sitting at computer screens.

Dad does want me to be part of the business, but I have to work my way up from the bottom. And, funnily enough that’s literally what’s happening to me.

I confess, I am not the hardest worker in the world. It’s nothing to do with having a wealthy dad, I would be lazy if my old man worked at Tesco’s. Dad knows this and when he set me to work at one of the regional offices of his global empire, he gave the guy who was to be my local boss strict instructions.

I had to stand there in the office and listen when dad told Mr. Furlong, “If he’s any trouble. Any trouble at all. I want you to take him across your knee and spank his backside for him. Hard.” Mr. Furlong’s face lit up and he cracked a broad smile. “I’m not joking, man,” my dad barked. “I mean it. I’ll be checking. If he doesn’t buck his ideas up and make some improvements with himself, I’ll know who to blame.” His eyes darkened. He was a hard taskmaster. Mr. Furlong knew exactly what dad meant – his job was on the line.

I was set to work doing routine tasks in the purchasing department, chasing orders and such like. Tedious. I couldn’t concentrate and spent a lot of my time skiving out of the office. I’ve always been like this. Whenever I could I avoided work; even at school. I had to get a lot of help with my A-level coursework or else I’d never have passed the exams.

I worked at a large industrial plant set over several acres, and it was very easy to find places to skive away from work. One trick I devised was to lie to my supervisor that I had been asked to run a message for one of the bosses and then disappear for an hour or so. There were many places to hide. A favourite I and lazy juniors hung out at was a disused basement room. Nobody ever went near the place, so we were undisturbed smoking cigarettes and reading sports magazines.

It was a different kind of magazine that got me into trouble. I was at another of my hiding places; a piece of open ground behind the main administration centre. Well let’s just say I have no self-control and overcome by the pictures of naked bodies in the magazine, I soon had the front of my trousers open and worked away at my todger until I came.

Only later in the day, did I learn the horrible truth. Every gasp and grunt had been filmed on a closed-circuit television camera. It was George, the security guard, who told me. “So, laddie, do you want this uploaded to YouTube for everyone to see?”

I crumpled to the floor, gasping for breath. George, fearing I was having a fit rushed to the phone and called the medical emergency number. Minutes later I was in the sick bay; calm now. It was only a panic attack the nurse assured me. I would be all right now, she said. But she was wrong.

As I sat sipping hot sweet tea, Mr. Furlong strode down the corridor in a fury, clutching a thick heavy ruler in his fist. He barged into the medical room. I mistook the look of anger on his face for one of concern. “It’s all right Mr. Furlong. I’m fine. It was nothing,” I chirruped.

Mr. Furlong’s face glowered dark red. “It is not all right and it is not fine!” he blasted. George had told him everything. In detail and with great relish.

“What a tosser! Hah! Hah! Hah!” he had guffawed. “Trousers round his knees! Wanking away! Too stupid even to see the camera. Hah! Hah! Hah!”

“You come with me!” I was startled by Mr. Furlong’s ferocity. “Now!”

Alarmed and uncertain about what was happening, I remained seated.

“I said…” Mr. Furlong did not finish his sentence. He grabbed me by the arm and dragged me from the room. Then prodding me all the time in the back, he frog-marched me down the corridor.

Within seconds he pushed me through the door of an empty office. We stood facing one another, each breathing heavily.

“You … you …” Mr. Furlong could not quite find the words. Eventually, he regained his power of speech. I was a moron, he told me, masturbating at work, in front of the camera. Did I not realise how he had made a fool of myself? More than that: everyone knew he was the boss’s son; and I had made Mr. Furlong look a complete idiot.

As his temper grew and the pitch of his voice rose, he brandished the heavy ruler in my face.

“You know what your father instructed me to do.” He was sweating heavily, although the room was quite cold. “What do you think he will say when he hears about this?”

God no! He must never find out. Nor must my older brother Kevin; I’d never hear the end of it.

“You know what!” Mr. Furlong was becoming increasingly hysterical. “I’m going to give you the hiding of your life!”

I gaped. Had dad really been serious when he said Mr. Furlong should throw me across his knee and spank my bum?  “But … but… you can’t,” I started to protest, but words failed me.

Mr. Furlong looked around the room, eyes searching for something. Then he found it. A heavy office chair with no arms and a straight back. “This will do perfectly,” he seemed to be talking to himself. He walked the length of the office and picked up the chair. It was quite a weight but he manoeuvred it into an open space. He stared wild-eyed across the room at me. “Come here,” he brandished the ruler and when I stayed rooted to the spot, he barked, “Now!”

Mr. Furlong was probably in his forties. He was not yet middle aged, but he was on the slide. His hair was thinning and his waist thickening. He wore a conventional business suit and I could see his belly hung over his belt. He waved the ruler once more. “Get here, now.”

We stared at one another for ages. I was starting to panic. Could I make a break for the door and run for it? I seriously considered it; but I also knew the reality of my situation. Dad had given Mr. Furlong his instructions and had made darned sure that I knew my boss was in total charge of me. If Mr. Furlong said I must be spanked than spanked I assuredly would be.

Mr. Furlong smacked the ruler into his left hand. “Now, I think we should get started. I haven’t got all day. Some of us have got work to do.”

I could not take my eyes from the ruler that at any moment would smack into my buttocks. It was a solid piece of wood, twelve inches long and about an inch wide. It was maybe a quarter-inch thick. It could pack a wallop, but surely with my trousers and pants on, I’d hardly feel a thing. It was absurd that a twenty-year-old man was being ordered to take a spanking, but I resolved not to make a fuss. If I didn’t take my medicine now there would be hell to pay when dad found out.

I slouched across the room and stood by Mr. Furlong. He sat on the chair and spread his legs a little. His thighs were flabby and as I stared down at them I found myself thinking what a perfect platform they would make for my prostrated body. He tapped his left palm with the ruler. It seemed we were ready to go. I started to lean forward to bend over his knees.

“Not so fast, Buster,” Mr. Furlong pushed me so I was forced to resume a standing position. My quizzical look got an immediate answer. “Trousers down. Pants too.”

I am sure my face reddened; both with shock and embarrassment. Go over his knees for a bare-bottomed spanking. Me, a twenty-year-old man. Could you imagine such a thing? My mouth dried and my temples started to throb. I was aware of blood rushing through my whole body. It was getting a little difficult to breath properly.

Mr. Furlong sneered, “Come on, laddie. Trousers down.” The look of contempt on his face turned to something quite different. It took me a second or two to decipher. He was enjoying this.

I closed my eyes tight and tried to pretend this wasn’t happening. It was all a dream. I had to go through with this, that was for certain. Even though I despised the old man sitting in front of me clutching a wooden ruler in his fist, I had absolutely no choice but to submit myself to him. My hands trembled as I gripped the buckle of my belt and unfastened it. Soon fumbling fingers had loosened the trousers of my smartly-tailored suit. Once I opened them and let go they fell at speed to the floor. The tail of my shirt covered most of my boxer shorts.

“Those too,” Mr. Furlong nodded at my underwear. “And be quick about it,” he rasped.

I hitched my thumbs into the waistband of the shorts and pushed them towards my feet. I was thankful that the shirt hid most of my manhood.

“Lift up your shirt,” Mr. Furlong face contorted. I’m certain he smirked when he saw my expression of horror. “Away from the buttocks, c’mon now.”

With shaking hands, I lifted the rich cotton shirt an inch or two higher.

“Doh!” Mr. Furlong spat as he slapped my hands away and grabbed my shirt and lifted it to half way up my stomach. Then, with great strength he pushed me in the small of the back until I toppled forward. I had to quickly take evasive action with my arms to stop me crashing into the hard, wooden floor.

I was winded by the unexpected ferocity of Mr. Furlong’s action. As I caught my breath, he tucked my shirt further up my back, ensuring my bared buttocks were now fully exposed. I felt him “saw” the wooden ruler across the centre of my bum. He was getting his aim. Then the ruler flew through the air in a wide arc to land with a resounding crack across my bum. My buttocks wobbled with the impact and then clenched and spasmed. The ruler was a surprisingly fearsome weapon and I couldn’t help myself groaning as the stinging pain travelled from my rear down the back of my legs.

With each painful swipe, my legs jumped and my feet kicked. My buttocks rolled slowly from side to side, clenching and writhing as the heavy wood turned my white creamy round buttock cheeks into a mass of painful stripes.

Apart from a few noisy gasps, I did not cry out at first, but as swipe after swipe connected with my bottom, I could control myself no longer. Tears flowed down my face and my sharp yelps turned to full-throated yells as my bum become red and swollen. I clung to the leg of the chair for dear life. Some instinct told him I had to suffer this. I must take everything Mr. Furlong had in store for me. No matter what, I needed to get through this. Somewhere deep inside myself I knew I had screwed up royally and I deserved all that I was getting.

I wasn’t counting the strokes. Mr. Furlong whacked the heavy ruler into my bare buttocks over and over again until every square inch of the flesh was covered by thin welts. He went from the top of the cheeks where they meet the spine, across both fleshy globes and into the under curves, the sensitive sit-spot where the buttocks and the thighs met.

My tears flowed freely and snot covered my mouth and chin. I was sobbing uncontrollably, but still I hung on to the chair.

When there was no flesh unscathed by the ruler, Mr. Furlong stopped.

“Up!” It was a curt command. I was engulfed with pain. I jumped up and did a merry dance, hopping around and rubbing my bottom, very conscious that my cock was flopping up and down in front of Mr. Furlong’s face. He was unable to resist staring at it. I don’t blame him – it is a whopper.

I pulled my trousers and shorts up while Mr. Furlong waited patiently. I was in control of myself now. I had stopped crying and my breathing was easier.

Mr. Furlong looked at his watch like he needed to be somewhere important. Without saying a word, he left, leaving me to nurse my swollen buttocks. I couldn’t return to my work station. Not yet. I still had important work to do. I had to find George, the security guard, and get that CCTV recording.

He seemed to know – or to have guessed – that Mr. Furlong had given me a seeing too. He oozed smugness. He would let me have the recording on one condition.

“No,” I replied a little too haughtily. “I don’t do deals with security guards.”

“Hah,” he snorted dismissing me as if I were something he had found on the sole of his shoe. “Please yourself. Enjoy watching YouTube.”

He had a point. Okay, I had to concede. What was his condition?

“Simple,” he started to unbuckle his wide leather belt. “Trousers, pants down. Bend over the chair.”


Other stories you might like


Paying the rent

Don’t bully our mum

Missed Opportunities


More stories from Charles Hamilton II are on the MMSA website

Charles Hamilton the Second

The Boss’s Son

z used art office otk ruler chair (8)

I had to stand there in the office and listen when dad told Mr. Furlong, “If he’s any trouble. Any trouble at all. I want you to take him across your knee and spank his backside for him. Hard.” Mr. Furlong’s face lit up and he cracked a broad smile. “I’m not joking, man,” my dad barked. “I mean it. I’ll be checking. If he doesn’t buck his ideas up and make some improvements with himself, I’ll know who to blame.” His eyes darkened. He was a hard taskmaster. Mr. Furlong knew exactly what dad meant – his job was on the line.

Extract from The Boss’s Son, a new exclusive story from Charles Hamilton II uploaded to The Canery website. Click here to read it


Other workplace stories you might like

Theft of petty cash

The boys in the mailroom

Over the boss’s knee


More stories from Charles Hamilton II are on the MMSA website

Charles Hamilton the Second


The Junior Salesman book


THE TWENTY-YEAR-old junior salesman slowly unclasped his belt and unbuttoned his trousers. He pushed them over his hips and let go. From there they slithered slowly down his legs.

A breeze from the nearby open window brushed against his naked legs as he awaited the next command.

Tyler looked over at his boss; in his hands was a wicked-looking school cane, around three feet in length and with a curved handle.  Mr. Davenport’s huge grin exposed his decaying teeth as he tapped a pointon the floor in front of him with the cane, “Please bend over and touch your toes.”


The Junior Salesman and other workplace whackings is the latest in a series of collections of my stories being published on Mondays. It runs for more than 19,000 words and has many illustrations. You should be able to read it on your lap top or e-book reader.

Click on the link below to download it free-of-charge.




Another book available for download free-of-charge.





More stories from Charles Hamilton II are on the MMSA website

Charles Hamilton the Second

Summer at uncle’s

used drawing cane hold (18)


This blogsite reached its first anniversary this week and to celebrate here’s a special full length story.


PETER, AN EIGHTEEN-YEAR-OLD from a small town, stays with Uncle Barnabas in London for the summer. The country boy soon learns the wicked ways of the city as he is introduced into the world of corporal punishment by a cast of characters including his cousin Albert; “out-and-proud” Nickie; and an old-fashioned schoolmaster by the unlikely name of Dr Cains.


Summer at Uncle’s runs for more than 12,000 words. You can either scroll down and read it here or download a special PDF version that can be read on a PC, computer or e-book reader. Click the link below. The downloadable version also has illustrations.

Summer at Uncle’s by Charles Hamilton II


Peter stepped off the bus and elbowed with other passengers to collect his rucksack from the driver. Victoria Coach Station heaved with people – of all shapes, sizes and colours.

The eighteen-year-old pushed his way through the crowds with mounting excitement. There were men with long beards, old women in saris, two women were dressed head to foot in black with only a slit in their costumes for their eyes. He had never seen anything like it before. This was going to be a summer to remember.

Peter had never been to London. He lived in a tiny town in Dorset. He had never seen a black face there; never mind women in burkas. The streets were crowded with people, many rushing to the coach station. He was pushed this way and shoved the other; a young man and a rucksack can take up a lot of space on packed pavements.

He found the Underground station and checked the handwritten note his mother had made. It was his directions to Uncle Barnabas’s house. He bought a ticket and made his way to the Victoria Line. He knew he had to change trains twice, but he was a bright boy and it shouldn’t be a worry.

It was Saturday afternoon and the platform was busy. Peter could see many were tourists. Some of the accents he heard sounded American. American! How glamorous. As he stood and waited for his train four men walked by. Other passengers made efforts to ignore them. They knew they were there, but they pretended otherwise. The four men were dressed in English school uniform. They wore black blazers with red edgings with white shirts and striped ties. That wasn’t what got them noticed. What everyone pretended not to see was the grey short trousers and long knee socks the men wore.

They were old enough to be his father, Peter thought, and one of them considerably more so. Who were they? He looked around expecting to see a film camera but there was nothing. Were they part of a publicity stunt; but if so what were they advertising. He gaped in bafflement. Suddenly, one of the adult-schoolboys caught him staring. The man flashed a cheeky smile and winked. Peter’s face resembled the colour of beetroot. He always embarrassed easily. He was mightily relieved when the train thundered into the station.

Otherwise, it was an uneventful journey. His mother’s directions were detailed. Soon he stood on the doorstep of Uncle Barnabas’s house. His uncle was the rich one in the family. He was “something in The City,” but Peter was not sure what. Stockbroking, he understood, but Uncle’s line of work bewildered him.

When Peter had been invited to stay for the summer he accepted with alacrity. London for three months, you betcha! What a time he would have. He was told he could even get a job; there was plenty of work in burger bars, or pubs, or filling supermarket shelves. He had just left school and was waiting for his exam results; if they were good enough he would be off to university in October.

He rang the bell and waited. It was a massive town house; his mother had said there were at least twenty rooms. It’s not a house, she had giggled, it’s a hotel. He waited and eventually the door opened. A rather formidable middle-aged woman stood and peered at him. He was disappointed a butler had not appeared. It was his Aunt Martha.

She smiled wanly and stood back to let him enter. His mother was right about the hotel. He stepped into a large hall and in the distance was a large spiral staircase. There were seven dark wooden doors, which he supposed led to drawing rooms and libraries and whatever it was that posh houses had.

Aunt Martha examined the boy standing before her and Peter tried desperately not to flush scarlet. It had been at least four years since they had met. It was at a cousin’s wedding. The whole family had attended; people feel obliged to attend such events.

Aunt Martha was tall for a woman and despite advancing middle age, she had a firm muscular body. She wore jodhpur-type trousers and a dark top, buttoned to the neck. Her eye glasses made her look a little fearsome; rather like an old-fashioned schoolmistress.

She waved her hand toward the staircase. “Follow me.” Her instruction was terse. She led the way up the stairs. Peter’s eyes followed her voluptuous backside all the way. His bedroom was massive; it was bigger than many flats back in his hometown. There was even an ensuite bathroom. Yes, it was a hotel.

“I’ll leave you to get settled; I’ll call you for supper,” and with that she turned on her heels and Peter watched her arse disappear down the passageway. He explored the room, opening and closing drawers and cupboards. All his belongings could fit into one of them. He stretched out on the bed, he had never before slept in a double bed. The one he had at home was so small his feet poked out the end. You lucky sod, he thought, you’ve landed a winner here.

He ran the shower, stepped in and washed himself down. His cock twitched; it often did this when he rubbed himself with soap. It had been a huge embarrassment to him at school after PE lessons. Suddenly, the vision of Aunt Martha and that arse flooded his senses. His cock ached. The erection was strong and powerful. He closed his eyes, lathered up the soap and worked away, first at his balls and then up and down the shaft. He suppressed a squeal when he reached the tip of his cock. But, he couldn’t hold out; it only took three strokes before a rush of cum shot across the shower.

He towelled himself down; ashamed. He had tossed off to the vision of his Aunt Martha, what kind of pervert did that make him?

It was a warm summer afternoon so he found his blue cotton shorts and clambered into them. Then he put on a yellow tee-shirt. He stepped into a pair of flip-flops. He was ready. His aunt hadn’t said when “supper” would be, but he supposed it was some time off. He would explore the house. He walked through the passageway; all the doors were closed. It was eerily quiet for such a large house. He padded down the staircase, intent on going outside to look at the garden and grounds.

He was walking through the cavernous hall when a crack like a pistol shot rang out. He knew it wasn’t gunfire. Then he heard another. It was coming from a nearby room. Intrigued, he pressed his ear against the door and heard voices. Then another crack. The door was ancient and the keyhole was wide. Checking that no one was in the hall to see him, for Peter knew spying was not right, he bent down and put his eye to the hole.

His pupil dilated. What the hell was going on? The vision the boy saw was of a young man bent across the back of a small padded armchair. His trousers were at his ankles and his underpants at the knees. Peter had an arse-on view, he couldn’t see the young man’s face, but surely it was his cousin Albert. It must be, he reckoned, because standing behind him about to flog a whippy school cane into his naked backside was Uncle Barnabas. He raised the cane high and swiped it with great force into the buttocks. His cousin shuddered, but kept his positon. Uncle Barnabas raised the cane once more.

Suddenly, Peter felt a great pain in his left ear as a hand grabbed it and hauled him to his feet.

“Peeping Tom! How dare you spy at keyholes!” It was a furious Aunt Martha. “What do you think you are doing,” she pushed him away from the door. “Get up those stairs. Go to your room. Stay there. I’ll deal with you later.”

At that second the door opened and Albert appeared. His pale face reddened when he realised his caning had been witnessed by his mother and cousin. He rushed up the stairs two at a time. A shamefaced Peter followed at a more sedate pace.

Supper was a quiet affair. Peter had three cousins but Alexander who was twenty was away at university in Newcastle and had decided to stay there for the summer. Elizabeth, a precocious sixteen-year-old, was travelling Europe with a friend’s family. That left Albert, who was Peter’s age, and Aunt Martha and Uncle Barnabas.

Albert sat in total silence. Peter supposed he was embarrassed about the caning. That, and the fact that he was dressed in grey short trousers, long socks and a white shirt. He looked like the four men Peter had seen at the Tube station.

Peter made polite conversation. He answered questions about his own family and his plans for the summer, but his heart was not in it. He wanted the meal to end. This was all too embarrassing. He hadn’t forgotten his aunt’s earlier threat, “I’ll deal with you later.”

At last he and Albert were allowed to leave the table. The cousins trudged up the stairs.

“Come to my room,” Albert smiled at Peter. It was a warm smile. The teenager’s face lit up when he grinned. His blue eyes sparkled and dimples formed on his cheeks.

Albert’s bedroom was huge but it was cluttered with the debris that teenage boys collect. He cleared cricket gear from a hard chair and let Peter sit. Albert stretched out on the soft bed. Peter wondered if his cousin’s backside was still sore. It looked like one heck of a caning. Peter had never been caned himself, nor spanked even, he didn’t know how painful it was.

Peter stared at his cousin and his short trousers. They were proper short trousers, like children wore with school uniforms, they weren’t summer shorts like Peter was wearing.

“The short trousers?” Albert had read his cousin’s mind. “It’s a long story,” he said and then launched into it. It had started a few months back when he had failed all his “mock exams” at school. He had been given twelve-of-the-best with a rattan cane by his father, but he left that part out of the story. He did tell Peter that his dad had the idea that by putting him back into short trousers it would concentrate his mind. It would also keep him in the house and stop him spending evenings and weekends with his friends. Which eighteen-year-old boy would want to be seen dead wearing short trousers?

So, that was it really. Short trousers as punishment. Peter remembered the men in the Tube station. He wasn’t a man of the world, but surely it was a bit kinky for adults to wear school short trousers. He thought better than to ask Albert what he thought.

He changed the subject. “Sorry about earlier …” he trailed off. He wasn’t sure how to broach the subject of Albert’s caning. “Your mum caught me spying at the keyhole,” he laughed.

“I’m surprised she didn’t take you across her knee and spank your bare bum with her hairbrush,” Albert said. Peter grinned and was about to make a witty rejoinder when he saw his cousin’s grim expression. He had not been joking.

“I’ll deal with you later.”

Peter blanched. No, surely not.



Later that evening Peter was in his bathroom. He had stripped down to his bright yellow briefs and was washing himself and cleaning his teeth. He studied himself in the mirror. He was thin and bony with a hairless chest and stomach; an eighteen-year-old youth with the body of a fifteen or sixteen-year-old boy. His mother often said he needed “fattening up.” He was a little shorter than average and his cheap short-back-and-sides haircut emphasised his schoolboy look.

He was startled out of his thoughts by a stern rat-a-tat-tat knocking on the door. Before he could respond the door opened and Aunt Martha stood grimly in the doorway. She stood for a moment as if apprising if it was safe to enter. When she saw her nephew standing with a confused expression and dressed only in his underwear, she strode in kicking the door closed behind her.

Peter stood transfixed. Aunt Martha was still dressed in her jodhpur trousers and black blouse. The image of her vast arse flashed before his eyes. His cock twitched. Instinctively, he cupped his hand in front of his penis, hiding any tell-tale movement. He was so concerned by her buttocks that at first he failed to register an important factor.

In her right hand she held a long thin leather riding crop. She allowed it to dangle at her side. She peered closely at Peter. She was a no-nonsense lady, she ran her own successful business; she knew how to get straight to the point.

“We don’t like peeping toms here,” she snarled. “Naughty little boys should not be peeping through keyholes.” She gently tapped the riding crop against her leg as she berated the teenager. His eyes widened as they followed the movement of the crop.

“We have standards in this house. Rules. Codes of behaviour.” She spoke as if she were addressing a room full of people. Then as if as an afterthought, she added, “Your mother would be ashamed of you.”

She stopped. An uncomfortable silence filled the room. Peter was dumb. Was he expected to say something? If so, what? Even as he had been spying through the keyhole to witness Albert’s bare-bottomed caning, he knew he was behaving badly. It had been a temptation that he could not resist.

Aunt Martha lifted the crop and pointed it at her confused nephew. “We have ways of dealing with naughty little boys in this house.”

Peter’s youthful, open face blushed scarlet. Why did she keep calling him a “naughty little boy?”

She bent the crop between her hands. It was a sturdy whip. It was not too supple. It was designed for horses. Its job was to cut into thick flesh to encourage a horse to obey its mistress. Aunt Martha knew it could also encourage naughty little boys onto better behaviour.

Peter watched transfixed as his aunt walked to the bed and leaned across it. Her buttocks stretched tightly against the smooth material of her trousers. Quickly, he averted his eyes. He must keep control of his cock. His aunt bundled together four pillows and quickly piled them one on top of the other at the edge of the bed.

There were no prizes for guessing her intentions.

“B.. B..” Peter was literally at a loss for words. What could he say? Everything Aunt Martha had said was true. He had spied on his uncle and cousin. It was a bad thing to do.

Aunt Martha straightened herself up and took up position a foot or two away from the bed. Peter’s heart raced.

“I’m surprised she didn’t take you across her knee and spank your bare bum with her hairbrush.”

Albert hadn’t been quite right. It wasn’t to be a hairbrush spanking.

Aunt Martha swiped the whip through the air before tapping it across the top of the pillow tower. The command was curt. She expected to be obeyed. “Bend over those pillows.”

Peter stood rooted; unable to move. He stared intently at the leather riding crop. He felt incredibly exposed, in only skimpy cotton briefs.

Aunt Martha glared. She was not used to such disobedience. “If you do not put yourself over those pillows I’ll come over there and pull your underpants down and tan your bare bottom so hard you won’t sit for a week, you naughty little boy.”

With his hands still strategically placed in front of his pants, the teenager slowly moved forward. His heart beat so loudly he could hear it. Blood rushed so fast through his body he feared his ears would pop. He stood for a moment at the edge of the bed looking down at the pillows. Then he fell forward. His face was pressed into the sweet smelling eiderdown; the toes of his feet brushed the deep pile carpet and his bottom was raised over the pillows.

His face was so close to the eiderdown that he could see nothing. Everything was black. He felt a rustle behind him and then heard a swishing sound. The pain was intense. Aunt Martha had landed the crop across the very centre of his bum. He wriggled from side to side. The intensity of the pain subsided almost immediately, leaving his behind throbbing.

He humped the pillows after the second whack slashed into his bum. That hurt. A lot. He lifted his head from the bed and sucked in great gulps of air. He was still wheezing for breath when Aunt Martha sent her crop whizzing into the underside of his cheeks. His pants were so brief that they hardly covered his arse. That cut stuck him on bare flesh and he yelped like a little whipped puppy.

Aunt Martha paused to admire her handiwork. Before her she saw her eighteen-year-old nephew laid face-down over a pile of pillows. His cotton-covered bottom trembled and quivered. The boy could not keep still; his body was moving up and down. He crossed and uncrossed his legs at the ankles. He buried his head in his arms. She could see he appeared to be in great pain; but he remained submissive waiting for her to continue the punishment.

She aimed higher this time and struck the top of his mounds. He huffed and puffed, “Huff, huff, huff,” and repeated his wriggling and humping.

She could not see his face and had no idea whether tears were flowing. To her tears were a bonus. Experience with her own sons told her big boys didn’t cry. Mostly they took their spankings stoically. They didn’t make much fuss, but that didn’t mean they weren’t exceptionally painful and something to be avoided.

She whacked two almighty stingers one after another. Slash. Slash. That got the boy panting and wheezing and rolling and rocking over the pillows. “Huff, huff, huff,” Peter wheezed. Then he settled and lay taking deep breaths.

Aunt Martha tucked the riding crop under her arm. That was it. Six-of-the-best. That would teach the naughty little boy to spy at keyholes. She looked down at the teenager, still gasping for breath.

“That’s it you can stand up now. It’s over. No more peeking at keyholes.”

Peter made no response. His face was still pressed into the eiderdown. Aunt Martha took one more look at the boy’s bottom. The backs of his thighs were striped red. His buttocks would be roaring, she thought. Serves the naughty little boy right.

Quietly, she opened the door and left. Peter waited a moment or two to make sure she had gone. Then, gingerly he lifted himself to his feet. He found he could not walk easily. The front of his underpants was full of sticky goo.




Uncle Barnabas and Aunt Martha were professional people and spent much of the week at work. That suited Albert perfectly, it meant he had the run of the house. It made him very popular with friends who had a ready-made place to hang out. London was spectacularly short of free meeting places for young people. The availability of many spare bedrooms in the house proved particularly attractive.

Nickie – with an “ie” as he constantly told people – was a welcome visitor. He and Peter sat in the large walled garden at the back of the house. Nickie had the whitest hair Peter had ever seen. Not even old men had hair so white. It must have come out of a bottle, he supposed. Nickie’s hair was expensively cut and was as flat as a plateau on top,

He was “out and proud.” Peter had never met a homosexual before. He didn’t think there were any in the town where he lived. If there were they probably kept quiet about it. This was 1986 and if you believed the newspapers, gay boys were a hazard to public health.

Albert appeared carrying two bottles of red wine and three coffee mugs.

Nickie’s eyes shone. “Where did you get those?”

“My dad has lots; he won’t miss a couple.”

He set the bottles on a table and expertly cut the foil and extracted the cork. There was a satisfactory glug, glug, glug as he poured wine into the first mug. Soon the three teenagers were toasting one another. Nickie and Albert took extensive gulps of their wine. Peter was not so confident. He had never drunk wine before. He was hardly a drinker, despite his age. He didn’t much like the taste of alcohol. He could make a bottle of Labatts last all night and still leave it behind half full.

Albert poured refills. Nickie lay back on a beach towel, strategically placed on the threadbare lawn. “I do adore you in those short trousers.” He loved to tease Albert. “Very sexy,” he snickered. Albert pulled a face.

Peter told them about the four men he had seen dressed in school uniforms at Victoria Underground station. “They were older than my dad,” he added incredulously.

“Oh they were probably going to the Whacko! Club,” Nickie said matter of factly.

“The Whacko Club?”

“Yes it’s a male corporal punishment club. They meet above a pub called the Spring Chickens. You see lots of guys dressed as school kids.”


“Others like to be headmasters,” Nickie added confidently. “Some are into heavier stuff. You know, whips and chains,” he smiled brightly and took another huge swig of wine.

Yeah right, Peter thought. This was a wind-up. No such places really existed.

“You should check it out, Pierre,” Nickie continued. “You’d go down a storm with your boyish hips and daft haircut.”

Peter resented being called “Pierre,” but what could he say? He scowled instead.

“I’ll take you next Saturday,” Nickie’s eyes twinkled as he observed his new friend’s reaction closely. “You said you might be looking for a job. You could earn more in one night at Whacko! than you’d get burning burgers at Wimpy in a month.”

“What are you talking about,” Albert grinned.

“Yes dear boy,” Nickie affected a Noel Coward voice, “Our fathers may spank us for free, but others must pay us a fee.” He collapsed in a fit of giggles. He poured the dregs of wine into his mug and nonchalantly tossed the bottle over the high fence into the garden next door.

“You shouldn’t do that,” Peter protested.

Nickie laid on his back, contemplated the heavy rain clouds forming overhead, and sighed, “Out of sight, out of mind dear boy.”

Albert opened the second bottle.

Suddenly, the heavens opened and rain lashed down. The boys gathered together the wine and mugs and dashed inside, leaving the towels to soak.

It wasn’t until the following Saturday that Peter and Albert got the call. Uncle Barnabas wanted to see them in his study. Immediately.

Albert, wearing his grey short trousers and Peter in a tattered pair of Levi cut-offs, stood side by side in front of Uncle Barnabas’ desk. It was a huge room, which he sometimes used when he worked from home. It had dark mahogany panels around the walls and a large window with stained glass decorations. Uncle sat behind a walnut desk. It reminded Peter of an old-fashioned headmaster’s study.

That wasn’t the only similarity. The last time Peter had seen inside this room was when he peeped through the keyhole to witness Uncle Barnabas thrash Albert’s bare backside with a whippy rattan school cane. He was relieved that the cane did not appear to be present that afternoon.

What was in evidence was an empty bottle of red wine sitting on the desk. Peter could not be certain, but it looked like one that the boys had drunk earlier in the week.

“Mr Joseph from next door tells me that this wine bottle,” Uncle Barnabas nodded at his desk, “was found in his back garden. He believes it was thrown over the fence from here.”

“Oh dad,” Albert flashed his winning smile. He made sure his beautiful teeth gleamed and his dimples showed. “It could have come from anywhere.” He smiled again as if to say, “Well, really, of course it wasn’t us.”

His father glowered. He was an angry man. He was sick and tired of his unruly son. “It could not. I have this wine specially imported. I doubt if anyone else in the district has wine like this.”

Albert’s face fell. The smile disappeared like ice in sunshine. “Oh,” he mumbled. There wasn’t much more to say.

“I have checked my cellar. There are two bottles missing. What do you have to say to that?”

Peter felt his face flaming up. Bloody wine. He hadn’t wanted to drink it. It gave him a thumping headache. Now, look at the trouble it was causing him.

Albert shrugged his shoulders and had the grace to look abashed.

“Albert, did you steal my wine?” It was a straight question demanding a straight answer.

“I wouldn’t call it stealing …” Albert began but trailed off, unconvinced of his own argument.

“Pah!” his father exploded, “What else would you call taking my wine without permission. It is downright theft!”

Albert stared at his bare feet. Peter shuffled with embarrassment.

“I won’t have it. I simply won’t have it. My own son stealing from me.” He rose from his chair and walked to the front of the desk. Peter saw he was wearing loose linen trousers and an electric blue shirt; perfect attire for a warm summer’s day. Incongruously, on his feet he wore bedroom slippers without socks.

Without speaking, he lifted a straight-backed chair from its place against the wall and set it down in the middle of the room. Peter eyed him nervously. Albert’s pretty face twitched. His eyes blinked fast.

Uncle Barnabas sat on the chair, reached down and took off the slipper from his right foot. He squeezed it in his hand. It was soft and the top was made of checked cloth. The sole was rubber. It was typical of its kind; similar slippers had been used to spank the backsides of naughty boys for generations.

He looked menacingly at his son. “You know the drill.”

“But dad,” Albert implored. He meant, “Dad please don’t spank me in front of Peter. It’s not fair.”

His father read his mind. “Don’t worry you will both get it.”

“But, it wasn’t Peter’s fault. I stole the wine, not him,” Albert was an incorrigible rogue most of the time, but he was an honourable boy.

Peter’s hopes were raised only to be dashed on the rocks.

“Maybe, but he helped to drink it.” It was his uncle’s last word on the matter.

“Now, shorts down. Bend over my knee.”

Albert’s short trousers had a half-elasticated waist so didn’t need a belt. Peter watched as the eighteen-year-old unfastened the metal clasp at the top and allowed the trousers to slip down to his feet. In one continuous movement, he stepped out of them and took two paces towards his father and then gently lowered himself across his lap.

He stretched his hands out ahead of him and placed the palms of his hands flat on the carpet. His legs were slightly bent at the knees and his toes hardly brushed the ground. Peter stood immediately behind his cousin. He had a magnificent view of his arse. Albert was growing out of his navy blue-coloured pants and they clung snugly to his buttocks. His crack was clearly visible through the smooth cotton.

It wasn’t strictly necessary, but Uncle Barnabas took hold of the waistband of the pants and pulled, making doubly sure that there were no creases in the seat. Satisfied that they fitted like a second skin, Uncle Barnabas raised the slipper to shoulder height and smacked it down across Albert’s left cheek.

The thwack of rubber on stretched flesh resounded around the room. Peter flinched as the slipper struck home, but Albert did not. He remained resolutely staring down at the carpet concentrating on its various mixes of brown. Uncle Barnabas moved his own left arm and used it to pin his son tightly across his lap, then he battered the boy’s bum with the slipper. Hard and rapid.

Albert gasped and wheezed. His face gurned like a gargoyle. His body twisted and turned. His legs kicked up and down. After twenty-four cracks, Uncle Barnabas stopped. Albert’s head was still bouncing up and down off the carpet.

The teenager remained still. It was not over yet. He knew from experience there was more to come. And there was. Unceremoniously, his uncle tugged the teenager’s underpants down until they bunched at the thighs.

Peter gasped. His cousin’s buttocks were bright red, but even from a distance he could detect a number of lines running parallel from left to right across his backside. There were the remains of the cuts from the cane Albert had endured the previous weekend. It must have been some thrashing, Peter supposed. His own bottom had been badly marked by Aunt Martha’s riding crop, but the livid red marks had quickly turned, first to mauve and then various shades of blue to yellow, and by Thursday they had disappeared altogether.

Uncle Barnabas clutched his slipper tightly and renewed the onslaught on his son’s now bare bottom. Albert at first folded his arms and when that did nothing to absorb the pain, he clasped his hands together rather like some people do when they pray. Another two dozen whacks tore up his savaged cheeks. Not one square inch of his buttocks and thighs was left unblemished. The pain was searing. A burning sensation ripped through the boy’s bum. Every nerve end was frayed.

Uncle Barnabas was an expert spanker, but his son was also an experienced receiver. A boy laid across his father’s lap to receive a sound spanking has little control over his body. It will involuntarily wriggle and squirm. Legs will kick out; it’s a reflex action. But, a boy does have control of the sounds he makes. Albert groaned and gasped but no matter how much pain he felt, he didn’t yelp or yell. He didn’t plead for mercy or promise to behave better in future if dad would only stop whopping his arse.

He did none of these things. As the parlance goes: he took his punishment like a man.

When dad spanked he gave twenty-four on the seat of the underpants and another two dozen on the bare. After whack forty-eight bounced off his bum, Albert lay quietly. The pain at the point of impact had been searing, but even now it was reducing to a constant throb. Soon it would be a warm glow. He waited patiently for his father to release his grip on his middle.

Moments later he was back on his feet with his underpants and short trousers back in their rightful places. He stood close to the wall of the study and massaged his bottom gently. It felt really good. He would never admit it to his dad, but his head always felt remarkably clear after a spanking. It was almost a feeling of euphoria. He couldn’t understand why.

He watched on as his cousin lowered his cut-off jeans and stepped out of them. Albert didn’t know it but Peter felt he had much to live up to. He greatly admired Albert’s grit. He hoped he could endure his spanking as well as his cousin.

Uncle Barnabas made no concessions for first-offenders. In his book a spanking was a spanking. It had to hurt considerably, otherwise what was the point of it?

Peter was shorter than his cousin and both his head and his legs dangled off the ground. The first slap took him by surprise and then he kicked his legs trying to escape the stinging spanks. He twisted and turned his body all over his uncle’s lap, but he held him tight with his big arm wrapped around Peter’s midsection. He beat out a staccato rhythm on the teenager’s backside, but Peter made no sound at all.

It felt like flames were lapping his bottom. Then the whacking ceased. Peter knew what was coming next. He braced himself. Without an instant’s pause, Uncle Barnabas reached for the waistband of Peter’s thin, small, green briefs and tugged them over the boy’s bony hips and lean rump, down to his knees.

Peter remained silent, but being in front of his cousin with his pants down and his bare bum up in the air was pretty embarrassing.

Uncle Barnabas delivered the first spank on Peter’s naked left cheek and then gave him a hard swat about every five seconds for the first ten or so, alternating between his left cheek and right. Peter endured this though his bum felt like he had sat in a bath of hot water. After about ten, uncle increased the speed to about one every second. It seemed like a blur and Peter felt the heat building and he was “oohing” and “aahing.”

He stopped spanking after twenty-four whacks and lifted his nephew off his lap. The boy reached back immediately with his hand and rubbed furiously, not realising that this made his soft cock bounce up and down in front of his uncle.

Minutes later the two boys were in Albert’s bedroom. Shorts and pants had been discarded and they were admiring the red sheen on each other’s raw backsides.

“Yours is even redder than the wine we drank,” Albert gently caressed his cousin’s savaged cheeks.

“Yours feels like it could heat the whole room,” Peter rubbed Albert’s backside roughly.

“Ouch, ouch, ouch,” he feigned pain. Both boys hugged and laughed. There was nothing to compare with the bonding two friends feel after they have been spanked together.

“It’s all Nickie’s fault,” Albert grinned. “If he hadn’t chucked the bottle over the fence we’d never have been found out.”

“That’s right,” Peter’s cock twitched. “So which of us is going to give him his spanking?” They both collapsed in a fit of the giggles.




“You want to cane me on my botty-wotty,” Nickie shrieked with laughter. “Oh, yes per-lease!” He put his hands on his knees and jutted his backside out comically. “Oh! Oww! Ouch! Eek!” he jumped up and down and clasped his hands to the seat of his ripped jeans.

Peter frowned, but Albert giggled. It was an absurd idea, he knew that. They had endured a sound bare-bottomed spanking over Uncle Barnabas’s knee for stealing his wine. They wouldn’t have been found out if Nickie hadn’t chucked an empty bottle into next door’s garden. Surely, the two teenagers had thought, he should be punished too.

“Yes,” Peter rebuked Nickie sternly, he wasn’t joking. “Why should you get away with it?”

Nickie beamed. He had a wonderful smile. His whole face lit up. His blue eyes shone and his ruby lips were very kissable. What Peter had not yet realised was Nickie often sold his arse to corporal punishment enthusiasts. He loved being spanked and caned. A punishment for him would be not to be caned.

“Sorry.” Nickie was genuine. He hadn’t meant to get his pals into trouble. It was his fault they got caught. They wouldn’t have been spanked by Uncle Barnabas if it wasn’t for him.

“Okay,” Nickie looked Peter in the eye. “If you want to you can cane me.” Peter could feel his face colouring up. He was always too easily embarrassed. “You too,” he looked across at Albert who was seated in a garden chair affecting an air of indifference.

“Sure,” Albert stood up. “I’ll fetch one of dad’s canes. We should do this indoors. In the lounge.”

While Albert rifled through his dad’s collection of whippy rattans, Peter rearranged the furniture in the lounge room. A leather armchair, so worn it must surely be an antique, was the right height. Nickie could bend over its back in comfort, but Peter would ensure what happened next was far from comfortable.

“Here we are,” Albert entered the room with a thin yellow cane tucked under his arm. “Let’s say six each. Twelve in all.” He slipped the cane into his hand and swished it through the still air. It made a terrific swooshing sound.

Nickie shrugged his shoulders. “Whatever,” he thought. He caught Peter’s eye; he had a maniacal glint. He looked as if he was going to enjoy this very much indeed.

Nickie’s heavy ripped jeans would give ample protection against the thwack of the cane; especially one as thin as the rod Albert was theatrically bending between his hands. Unbidden, Nickie unbuckled his belt, popped the metal buttons on his fly and pushed the Levis to his feet. He wore a pair of very (for Nickie) conventional maroon-coloured briefs. His mother had probably bought them for him at Marks and Spencer.

He leant over the back of the chair and gripped the front of the seat cushion. Close up, Nickie could see how distressed the leather was. It smelt of dust. At that moment, the teenager realised the chair might have been in the family for generations. How many people had been in his position over the years, he wondered, with their head low and bottom held high while some master in authority whipped their arse with a cane?

His thoughts were interrupted by a sharp sting. Albert had delivered his first stroke. Nickie felt it, but it was hardly painful. Nor were any of the six strokes Albert administered. He didn’t want to hurt his friend; why would he? If it wasn’t for Peter, he wouldn’t be doing this at all.

Albert handed the cane to Peter. Peter was no expert in caning, but he remembered how Uncle Barnabas had dealt with Albert, the time he peeked through the keyhole of the study. Uncle had put some beef into the strokes. And so did Peter. He swiped the cane across Nickie’s maroon underpants with great force; he might have been beating a carpet.

Nickie felt those strokes. He screwed up his face and puffed out air through his teeth after each one landed, but he made little sound. The teenager was often caned; he had a very high pain threshold. With the guys he considered his “clients” he would put on a show. If they wanted him to he would yelp and scream and beg to be let off the caning. Others preferred a more stoical reaction where he simply bent over and absorbed the sometimes intense pain.

Nickie’s arse throbbed when Peter had finished, but rather like a schoolboy who had been caned by his headmaster, he wasn’t about to let the teenager know he had hurt him. He bent down and pulled up his jeans.

“Right,” Albert was embarrassed. How should this end? Then he had an idea. “Who says we go to the pub. Nickie’s buying.”




It would soon be granddad’s sixty-fifth birthday and the family planned a party. They asked him to find mementoes – photographs and the like – from his childhood and teenage years so they could make a display. He had lots of things in the loft at home, but Aunt Martha thought he was too old to be climbing ladders and crawling around the roof space so she despatched Peter and Albert to do it. When they got to his house they found him already sorting through cardboard boxes.

“You shouldn’t be going in the loft granddad,” Albert chided.

“Why ever not?”

“Because you’re an old man now,” he teased, running the word “old” around his tongue as he had once heard Nickie do.

Granddad knew he was being wound up, so he gave some back to his grandson. “I see you father still has you dressed in short trousers.”

Albert wasn’t about to let his granddad know but he was used to the juvenile clothes. When he walked the streets nobody seemed to notice he was dressed in school uniform and his friends thought it was a good laugh. Being forced to wear grey school short trousers like a little boy was not much of punishment and it was infinitely preferable than going over his dad’s knee for another bare-arsed tanning.

Granddad picked up a small pile of yellowing papers. “My old school reports,” he waved them around. “I’ve got them all. This one’s when I was twelve. It says, ‘Richard is very lazy. He would do well if he applied himself.’” Granddad chuckled. “My father gave me a good hiding when he read that.” Peter couldn’t be sure but he thought the old man’s eyes misted at the memory. “It must have done me some good, I passed my exams and went on to university.”

He put the school report on the dining table. It would be ideal for his family exhibition. Uninvited Albert delved into a box. There were several fading back-and-white photos. “What’s this granddad?” He held up a picture of two teenagers in what even without the benefit of colour he could see were clearly posh school blazers.

“Blooming heck,” he said. Granddad usually swore like a trooper but it amused him when he was around his grandchildren to pretend that he was genteel. “I haven’t seen that picture for years. St Augustus Grammar.” He trailed off, suddenly overcome with a memory.

Albert peered closely at the picture. It was clear which of the two boy was granddad. These days the old man had little hair and had fleshed out considerably since his schooldays, but the shape of his head and the sticky-out ears were unmistakable.

“Who’s the other boy?” Peter thought he looked sad, as if he were carrying the troubles of the whole world on his shoulders. Granddad took hold of the photo and studied it intently. “Geraldson Major,” he whispered. “Old Gerry,” his lips quivered into a wan smile. “We got up to some scrapes.”

Albert beamed and nodded his head vigorously, encouraging the old man to tell a tale of his schooldays. “Six of the best,” granddad stuttered the words. “We were in the sixth form. Eighteen years old. That blinking headmaster, we called him Dr Toaster, because he was always warming up boys’ backsides.” He trailed off once more.

“So what did you do granddad?” Albert knew that the old man used to beat his own father with a cane when he was a boy. Corporal punishment was a family tradition. He would enjoy hearing that granddad was also given a sore bum when he was a kid.

“Nothing really. We skipped school so we could line up and buy tickets for the FA Cup semi-finals. We got found out, of course. We got a sound caning for our troubles.” Granddad’s voice changed. He appeared to be mimicking his old headmaster. “Trousers down. Bend over. Touch your toes.” Granddad’s eyes twinkled. “I suppose old Toaster was a rugby man.”

He looked closely at the photograph and the twinkle faded and his eyes misted. “Poor Gerry. He died in the war.”

Just then the front door opened and closed. “In here!” granddad called. A youth no older than Albert and Peter appeared. He had jet black hair – obviously dyed – which stuck up from his scalp in all directions. He looked like a throwback to the Punks. He was laden with four bulging Tesco carrier bags. “This is Ferris,” granddad said by way of introduction. “Some of my grandchildren,” he nodded at the two teenagers.

“Pleased,” Ferris grinned a crooked smiled. Then looking at the bags in his hands, he said, “I’ll just put these away.”

“Who was that?” Albert liked the boy already. He was odd-looking, someone who was not conventional.

“That’s Ferris. He stays here sometimes.”

“Is he your lodger?”

Granddad beamed. “Ferris!” he shouted so the boy could hear him in the next room. “Albert asks if you are my lodger!” A shriek of laughter peeled from the kitchen. “Well, I suppose rent is sometimes involved.”

Granddad’s face flushed and he returned his attention to the boxes. He picked up a bundle of letters tied up with string. The knot was too tight. “Flipping heck. I can’t untie this.”

“Here,” Peter delved into his pocket and withdrew his pride and joy: a Swiss Army Knife and granddad cut the string.

“What are they granddad, love letters?” Albert’s face shined. Was he about to discover some juicy secret about the old man’s past? Granddad shuffled the envelopes in his hands. “Birthday cards mostly. Picture postcards. Nothing too interesting.”

Ferris returned to the room and hovered unsure what he should do. “Should I …?” he asked, raising his eyebrows. He meant should he go upstairs and keep out of the way.

“No, Ferris. We’re looking at my old photos and things.”

Ferris picked up the school photo and held it close to his face. Peter thought the boy must need glasses. “What a sexy creature you were,” he shrieked with laughter again. Granddad’s face flushed, but his shoulders heaved. He had enjoyed the compliment immensely.

About an hour later, Peter and Albert were approaching the Underground station on their way home. “Bugger it,” Peter stuck his hands in his pockets, searching them all. “I’ve left my knife behind.”

Albert shrugged. “C’mon. let’s go back. It’ll only take ten minutes.” They walked in companionable silence. At the house they heard the sound of a vacuum cleaner whirring. Peter had an insatiable curiosity. Many would say he was “nosey.” It got him in trouble sometimes. He still masturbated at the memory of the riding-crop thrashing Aunt Martha gave him for peeking through the keyhole when Albert was caned by his dad.

Instead of ringing the doorbell, Peter stepped over the flowerbeds and peered through the window. One day he would learn this was bad behaviour. Spying was an intrusion of privacy. Sometimes you saw things it was better not to see. Some secrets were best left unrevealed.

Inside the lounge room Ferris was entirely naked, except for a pair of gleaming white briefs. They were a size or two too small. The under curves of his buttocks were visible and even from a distance Peter could see the outline of the boy’s cock. Unlike, every boy Peter knew, Ferris was not circumcised.

Granddad sat in the centre of a large leather couch watching. Ferris sashayed his hips and tight bottom as he glided the vacuum cleaner across the rug. Then, he released the Hoover and put his hands on his knees, stuck out his bum and wriggled it. Still bending over, he looked over his shoulder at granddad.

The old man gave a signal with his eyes. Ferris straightened and skipped across the room to granddad. No words were spoken. Ferris lay face down across granddad’s lap. The couch was large enough for Ferris to have his chest on one side of granddad and stretch his legs behind him. His toes rested on the arm of the couch.

Peter watched astonished as granddad, slowly and gently peeled down the tight briefs. Ferris’s bum was creamy white and contrasted starkly with his deeply suntanned body. Granddad gently caressed Ferris’s buttocks, making circling motions. He pinched the teenager’s flesh. The bum was tight; there wasn’t much “give.” Then, granddad, stroked Ferris’s hairless back. He spent some time at the shoulders. Ferris purred like a cat.

Suddenly, granddad raised his right hand and brought it smacking down into the teenager’s left buttock cheek. Then the right. He kept up a staccato rhythm; randomly smacking the cheeks high, then low, then high, then at the crest of the mounds.

Albert stared at his cousin. The look on Peter’s face scared him. He moved forward toward the window. “What is it? What are you looking at?”




Peter got a part-time job at a burger bar and he was loving every minute of it. Most of the people who worked there were like him; they had just left school or were students on vacation from university.

He was there one day when the manager Billy had a public row with Timothy. “You’ve been falsifying your timesheets,” Billy accused.

“No I haven’t boss,” was Timothy’s predictable response.

“You have. I’ve been going through them You’re putting an hour or more extra a day. That adds up to a day a week.”

“It’s just a mistake. Sorry boss.”

Nobody was working by this stage. There were all ears. Those who had worked at the bar for a while knew where this would end.

“It’s no mistake. You’ve been doing it every day for weeks.”

Timothy looked abashed. So did a few of his co-workers. Inflating the timesheets was the oldest trick in the book. You could get away with it too if you didn’t get too greedy.

“I should sack you,” Billy frowned.

“Oh, come on boss,” Timothy flushed. He didn’t need the sack. He had payments to make on his car.

“Alright. Come and see me in my office at the end of the shift.” With that Billy strutted from the room.

A gang of schoolchildren came into the bar and they got back to work. Everyone knew what “see me in my office at the end of the shift” meant, but not a word was spoken on the subject.

At six on the dot, Timothy gingerly knocked on the office door. His shift was over but he still wore the burger bar uniform; cheap black polyester slacks and a top that looked like it was styled for a puppet in Thunderbirds. Billy was seated behind his desk. It was piled with paperwork. It always was; none of it ever seemed to move.

Billy wasn’t much older than most of his staff. He wouldn’t turn thirty for another eighteen months. He had been in the burger business for years. The work suited his personality and gave him ample opportunities to feed his appetite. The increasing number of foreign workers coming to London were especially to his taste.

Timothy wasn’t “foreign”, he was London born and bred. So were his parents and their parents before him. He was a bright lad and was working at the bar during university holidays.

“Do you admit falsifying the timesheets?” Billy knew he had, but he would still like a confession.

“Yes, boss. Sorry.”

Billy grinned lasciviously. He should demand that the money be repaid and once that was done he should sack Timothy’s arse. But, he wouldn’t. Billy wouldn’t sack his arse, but he would give his arse a damn good spanking.

“I think you know what happens now,” Billy spoke softly. He never spanked in anger. He took his time. He relished every moment.

Timothy knew. The youngster had a spanking fetish for as long as he could remember. He dreamed about it most nights. The latest involved his mother. Timothy’s grades were poor, so he was over her knee, his pyjama bottoms at his feet while mother hammered her hairbrush into his naked buttocks. In the dreams he wasn’t a kid, he was his real age; twenty-one.

Timothy would prefer to be spanked by a woman, and a matronly one at that. But beggars can’t be choosers, so Billy would have to do.  His boss opened a desk drawer and reached inside. He withdrew a solid wooden ruler. He rose from his chair, navigated the desk and stood in the centre of the room. “Bring that over here,” he indicated a worn wooden chair with a straight back that stood against a wall.

It was heavier than it looked, but Timothy soon had it in position. Then, Billy sat down and spread his legs. “Now, get over here.” He pointed to his right side, indicating that Timothy was to stand there. He did. His heart was thumping and he was certain his face was scarlet. He had often dreamed of being spanked, but apart from a bit of a fumble with a girl at university, he was a spanking virgin.

“Lower your trousers, boy.” Timothy blanched. He had thought he wanted this so much, but now at this last minute he was not so sure. He was losing his nerve. He stood rooted. “Down,” Billy repeated pointing with a bony finger. “Right now.”

Still, Timothy did not move. “Pah!” Billy expelled air through nearly clenched teeth. He pulled the young man toward him and quickly unfastened his black polyester trousers. Timothy felt the static electricity crackle as they slid over his thighs and rested at his knees. Billy gripped them again and guided them to Timothy’s feet.

Billy paused to admire the bulge in the front of Timothy’s briefs. They fitted snugly and the outline of the young man’s cock was clearly seen. Billy noted with disappointment that Timothy’s cock was cut. He skinned the briefs past his knees and smiled as the cock bounced up and down in front of his face. It wasn’t erect, but nor was it fully limp.

“Over my knee,” he quietly ordered, and fearing Timothy would be reluctant, he gripped his right arm and guided him across his lap and helped him to settle into place. Timothy stared down at the hard industrial strength carpet. It needed Hoovering, he noticed. The rough carpet scratched his palms when he put the weight of his body on them. Behind him, the toes of his shoes rested comfortably on the ground. His knees were bent slightly and his bum lay at a forty-five-degree angle against Billy’s right leg. The boss gripped Timothy around the waist. He was going nowhere until Billy said so.


“This is going to hurt you more than it hurts me, boy.” Billy liked that joke, he used it often, especially with first-timers. He kept his word as he lifted his strong right arm and whacked the heavy foot-long ruler into Timothy’s buttocks time and again until they turned bright red. Timothy kicked his legs. It was a reflex action He had no control of his body. Billy paused the spanking, forced the young man further forward and wrapped his right leg over Timothy’s calves. That stopped his kicking.


Billy’s target was now more accessible, and more vulnerable. He resumed spanking, hard and fast. Every time Timothy thought the target had gone numb, Billy found areas of the buttocks that were still tender until no part of Timothy’s backside was left unblistered. Satisfied that there was not a square inch of flesh left untoasted, Billy stopped. He hooked his leg away and released his grip on Timothy’s back. The twenty-one-year-old jumped to his feet. Billy roared with laughter. Timothy’s cock was rock hard and pointing up at the ceiling.


Billy didn’t immediately take it in his mouth. Instead, he poked out his tongue and started to lick up and down the iron-hard shaft, as if it was an ice lolly. He paused at the rim of the swollen head. He did this for minutes, while holding the dick tightly at the base. The cock was purple and ready to explode. Timothy was desperate to shoot. Billy ran his tongue in a circle all around the rim. Timothy balled his fists and curled his toes. Just as he thought he could stand it no longer Billy opened his mouth and the top half of Timothy’s cock slid smoothly inside.


Outside the office door Peter was ready to leave. His shift was over and he had changed back into his street clothes. As he turned toward the staff exit, he heard what sounded like a scream of anguish from Timothy. My God, Peter thought, the poor guy’s being tortured.




“Stand there, bend over. Touch your toes, it’s six of the best for you young man.” Dr Cains flexed the rattan curve-handled cane between his hands and then swished it at point on the floor in the middle of the room.

Peter eyed the cane apprehensively. He had never seen a school cane close up until that day. It was thin and whippy. He supposed as canes went it was at the lighter, milder end of the scale. Dr Cains swiped the cane through the air once more. “I am waiting Wharton, I am waiting.”

Peter’s heart thumped so loud he was sure Dr Cains could hear it from the other side of the room. His hands were trembling. Taking care not to catch his punisher’s eye, he stepped forward, took a deep breath and bent from the waist. Touching his toes was harder than he expected; it put a terrible strain on the calves.

He concentrated hard on the stained carpet beneath his feet. He felt the cane being tapped across the middle of his stretched bum. The Terylene cloth of his grey short trousers clung to his buttocks. His green-and-gold diagonally-striped tie dangled in front of his eyes. He clenched his mouth shut, waiting for the fearsome sting of the first stroke.

Peter had travelled to London to stay with his uncle wanting new experiences. But this wasn’t quite what he had in mind when he left his tiny town in Dorset.

Peter, Albert and Nickie had met in a pub in Soho. It was one of Nickie’s regular haunts. It was a “gay bar.” Peter never knew such things existed. It was packed and guys that Nickie knew came to their table, chatted and moved on. Peter thought Nickie had a lot of friends.

“So do you want to come to The Whacko! Club next week, Pierre?” Nickie sucked on a bottle of designer lager.

Peter looked puzzled; he had forgotten their earlier conversation.

“Whacko! The CP club.” And when Peter still looked baffled, he explained. “CP. Corporal punishment.”

Now Peter remembered.

“I thought that was a joke.”

“No. They meet every Saturday. It’s been going on for years.”

Peter remained silent.

Nickie was a man on a mission. He wasn’t going to leave the bar until he had made a sale. “There are lots of people who go. They’re a great bunch of pals.” He studied Peter’s reaction. He hadn’t known the teenager for long, but he had detected a spark behind the eighteen-year-old’s eyes when Peter had caned him over the wine incident. He could be converted to the cause.

“Thing is, they are mostly middle-aged fellows, or old.” He rolled the word “old” around his tongue, as if he were describing a group of rare, rather absurd, creatures from Papua New Guinea. “So, every so often they bring in a group of youngsters to play with.”

Peter flushed scarlet and examined the label on his Labatts intently. He didn’t want to hear this. He knew where Nickie was going. It scared him a little.

Until he had come to London, Peter had never received corporal punishment. Then within a week of his arrival he had been beaten with a riding crop by Aunt Martha and taken across Uncle Barnabas’s knee for a spanking with a slipper on his bare bottom.

He had ejaculated into a pillow even while Aunt Martha was still lashing his buttocks. He hadn’t disgraced himself in that way with Uncle Barnabas, but afterwards he had a sensation he had never felt before. He didn’t understand it and he couldn’t describe it. It was as if his head had never been so clear. It was a kind of euphoria, an ecstasy. He had never felt so “good” before. He wasn’t much of a drinker and never had the chance to take drugs, so he wasn’t sure if he was on some kind of “high.”

It worried him and excited him in equal measure. He might not know “what” had happened to him, but he did know “how.” Corporal punishment turned him on.

“So the guys at Whacko! have themed parties,” Nickie continued. “One time it was Boy Scouts, another, no surprise here, it was schools and headmasters. One time we dressed up as footballers. They talk about managers giving their players the ‘hairdryer’ treatment; we got the ‘hairbrush’ treatment,” he giggled, knowing it was a lame joke.

Peter swigged at his beer too quickly. It went down the wrong hole and he coughed so violently Nickie thought he might choke to death.

After Peter had recovered, Nickie carried on. “We’re doing schools again.” He nudged Peter playfully in the arm. “You will go down a treat. You even look like a real schoolboy.” He hesitated, “No offence. You could tell them you were still at a school. It’s nearly true, you’ve only just left. They would blow a fuse.”

Nickie was babbling now. “And, if you let on that you just had a spanking for real from your uncle, they’d all want to adopt you as a nephew.”

Nickie paused, trying to gauge Peter’s reaction. His new friend’s eyes were glazed, but he knew it wasn’t caused by the beer.

“Oh, did I say?” Nickie lent in so close Peter could smell his beery breath. “No sex. They can’t do sex. CP is all right, sex is against the law. Nothing like that happens …” he trailed off. He knew he wasn’t quite telling the truth. All sorts of things happened after club night ended, but that was in the privacy of people’s own homes.

“Oh and,” he hoped this might be the fact that would seal the deal, “the money’s fantastic. Bugger filling shelves at Tesco.”

Later that night in his bedroom at Uncle Barnabas’s, Peter replayed the night in his head. He had given Nickie the brush-off. The Whacko! Club was too dangerous. Letting complete strangers spank and cane you. What was Nickie thinking? His new friend insisted that there was no danger. The guys had rules and they kept to them. Nobody did anything they didn’t want to, Nickie had said emphatically. And besides, he wouldn’t be on his own, there were usually seven or eight youngsters at the party – there was safety in numbers.

Peter had a fitful sleep. He woke at about three with a raging hard-on. His cock ached so much it was about to burst. If he hadn’t woken in time he would have soiled the sheets. He ran into his private bathroom and unfurled a yard of toilet paper. His hand made several frantic tugs along the full length of his bursting cock. His body juddered as pints of cum soaked into the tissue.

He washed his dick and staggered back to the bed. He couldn’t get back to sleep. He usually never remembered his dreams, but this one haunted him. It had been vivid, precise. He remembered every detail clearly. He was back at school. In the headmaster’s study. The old man was dressed in academic gown and mortar board. In his hand he gripped an awesome thick crook-handled cane. In front of him bent across the back of an armchair was Peter. His pale-grey long trousers were at his feet; his white Y-fronts at the knees. His bared-bottom was raw with red welts. The headmaster raised the cane and flogged it down into the naked haunches; over and over and over again.

Two days later, which was the next time that he met Nickie, Peter put his name down for The Whacko! Club.

It was lust at first sight the moment Dr Cains clapped eyes on Peter. Dr Cains – it wasn’t his real name – was one of the organisers at The Whacko! They met at the pub in Soho. The boy sitting before him was a thing of beauty. Was he really eighteen years old? Dr Cains wondered to himself. Later, he would ask for some proof of his age. The club couldn’t break the law.

Peter had not dressed up for the occasion. He wore his yellow tee-shirt and blue cotton shorts and flip-flops on his feet. Much of this was hidden below the table away from De Cains’s gaze. What the elderly man did see was a young fresh-faced boy. He tried not to peer too intently, but had the delightful creature yet started shaving? He was so slender most people would say he was “skinny;” he had the body of a fifteen or sixteen-year-old. His dark brown eyes would melt the stoniest of hearts and that haircut: it was straight out of the nineteen-forties.

Dr Cain couldn’t see the boy’s bum – Peter was sitting on it – but he knew instinctively it would be pert and deliciously spankable.

The meeting was supposed to be an “interview;” as if Peter had applied for a proper job. There was no need for that, Dr Cains had already decided. The only question he had was, “When can you start?”

The answer delighted him. “Any time,” Peter swigged at his Coca-Cola, a little taken aback by his own confidence.

“What size waist are you Peter?” The question startled the boy. Dr Cains was thinking of the Whacko! Club’s extensive range of costumes. He was pretty sure they didn’t have a pair of short trousers small enough to fit the boy.


Twenty-six-inch waist. Dr Cains gasped. “Dear boy, I can buy you short trousers at the children’s department of John Lewis. Do you have a school blazer? No, I suppose they are all back home in Dorset. Don’t worry,” Dr Cains was talking to himself, “I will kit you out. White Y-fronts? No, I don’t suppose so.”

He leaned over to Nickie, “Bring him to my flat at three o’clock for an audition. Don’t be late. Don’t be drunk.” With that Dr Cains rose from his seat and trilled, “I must fly. To John Lewis, I must fly!”

Peter sipped at his Coca-cola and Nickie swigged at a bottle of over-priced tasteless Mexican beer.

It was three-fifteen. Peter was dressed in smart mid-grey short trousers. They fitted him perfectly; John Lewis had served him well. They were a little longer than the summer cotton shorts he had been wearing; they fell to about an inch above the knees.

His gleaming white shirt was too big and hung loose at the neck. He pulled a striped tie up tight. Dr Cains had produced a fancy green blazer with gold braiding. The badge said it was from St Francis Independent Grammar; a real school, apparently.

He pulled on long grey knee socks. They were woolen and in the heat of the summer’s afternoon, they itched his legs. He had no “regulation” black lace-up shoes, so they decided to go without.

Dr Cains dressed his part as well. Peter stared in wonder. The old man had gone to enormous trouble with his costume. He had a heavy tweed jacket and old black trousers with thick grey stripes. Across his back was a tattered academic gown. A mortar board cap with a tassel at the back perched precariously on his head. But the piece-de-resistance was his shirt. It was a grubby off-white colour held together at the neck by a cardboard wing collar.

They stood in an ordinary sitting room. There was a cheap vinyl settee, one armchair and a dining room table with matching chairs. No attempt was made to disguise the room as a headmaster’s study.

“We shall call you Harry Wharton,” Dr Cains said pleasantly. He paused; Peter did not recognise the name.

“We call Nickie, ‘Bob Cherry,’” he continued. Still Peter was uncomprehending. “Bah,” Dr Cains ejaculated. “You young people today, you know nothing.” He was genuinely upset that the heroes of his childhood (and indeed continuing into his adulthood) were unknown to the younger generation.

“Sorry, who are they?” Peter’s question was genuine.

“Go to a library. Find out yourself!” Dr Cains barked.

He was genuinely irritated with the teenager. The numbskull deserved six-of-the-best for his ignorance. It might add a little authenticity to the proceedings.

“Stand there, bend over. Touch your toes, it’s six of the best for you young man.” The audition had begun. Peter understood. Dr Cains had said they didn’t want a “newbie” as he called him to flunk it at the club; to “bottle it” at the last minute. They had to be sure Peter had the fortitude to take Six.

Peter stretched his fingertips to touch his feet. It put a strain on his knees. “Spread your legs by a foot or so, it will make it easier.” Dr Cains’s instructions were helpful. Soon, Peter had maneuvered himself into position.

Dr Cains took his time. It really was a perfect bum. He had caned many arses over the years. Truthfully, most of them on offer at The Whacko! Club were well-covered. No, Dr Cains thought, that was being overly-polite; they were fat. He wondered if a caning hurt more if you had a fat bottom? Were there more nerve ends for the cane to strike?

Not everyone at The Whacko! was fat. There had been one guy whose buttocks were non-existent. He had legs that disappeared up into his back. His bum was almost perfectly flat. Now, he thought about it, Dr Cains reckoned caning would probably hurt more on a small bum. There wasn’t much area to aim at and the cane would land time and again on the same spot. Yes, that would hurt terrifically.

Peter’s bum wasn’t so small that the old man would be able to land six cuts across it and not land two in the same place. It depended, of course, if Peter could stay still and “take it like a man.”

They would soon find out. Dr Cains found his target and tapped the tip of the cane gently across the taut Terylene. He let fly. There was a tremendous crack as the cane hit home. There was something about man-made fibres that amplified the sound of cane against trousers. It made a much duller thwack when aimed into a backside covered by wool.

Peter’s fingers sprung from his toes and he half lifted his body, intent on standing to rub his bum. But, he realised his mistake and he steadied himself just in time. He resumed his submissive position, ready for number two.

Dr Cains landed it just an inch below the first. Peter’s eyes scrunched up. He felt that. His backside throbbed.

“Stand up.”

Peter hadn’t expected this. He had been told it would be ‘’six-of-the-best.”

“Shorts down. Bend back over.”

Peter frowned. Of course, the guys would want to go further than the trousers.

He surprised himself by his calmness. The short trousers had a half-elasticated waist, so he needed no belt. He undid the metal clasp at the top and let them slither down his legs to his feet. Then he took a deep breath and bent over.

He felt Dr Cains tug at the waistband of his Y-fronts. He was making sure there were no creases in the pants and they clung to his buttocks like a second skin. While the “doctor” busied himself, Peter studied the label inside his shorts intently. It said they were, “15 years sturdy fit.” Which school made its fifteen-year-old pupils wear short trousers? Peter didn’t know of any. Not even the very posh schools in Dorset did that.

His thoughts were interrupted by a searing pain across the top of his buttocks. He expelled air through clenched teeth. It sounded like a car tyre puncturing. That stroke was the worse yet. The others had throbbed, this one burned.

So did the next. He now had four lines of pain in a band from the top of his bum to the crown. It hurt, an authentic caning was supposed to after all, but Peter felt OK. He was on top of this.

“Stand up. Pants down.”

Peter had expected this. It was two-two-two. Two on the shorts, a couple on the pants and the last ones on the bare. He hitched his thumbs in the top of his pants and pushed them to his knees. As he bent over the force of gravity helped the Y-fronts slip to his feet.

His heart raced; he recalled the vivid dream with him bare-arsed over the armchair in the headmaster’s study. His head buzzed. In his half-naked state his cock and balls were inches from his face. He hoped he could hold out. It wasn’t the pain of the punishment that troubled him. He didn’t feel embarrassed that he was showing an older man his bare buttocks, crack and hole. But, it would be deeply humiliating if his cock sprang to attention now.

Dr Cains paused to admire his handiwork. There were four lines across Peter’s buttocks. A couple were quite red, but he knew he wasn’t beating the teenager with any force. His strokes would make the boy gasp a little, but they wouldn’t do much damage. The marks would clear quickly and he would have unblemished buttocks before “showtime” on Saturday.

He put the final two on the underside of Peter’s bum, where the cheeks met the thighs. “Hissssss.” They hurt. He wriggled his hips and held tightly onto his ankles as the pain travelled from his buttocks up and down his legs. Blood rushed to his brain.

When instructed, he rose to a standing position. His dreamy brown eyes were damp, but he was far from crying. He clutched his hands to his burning bum and hopped about. Dr Cains watched lovingly. What a dish Peter was to set before any king – or, indeed, queen.

He pulled up his short trousers and pants. The intense agony he felt as the cane impacted his stretched pert buttocks had already gone. He felt a warm glow across his seat. His mind was clear. He grinned at Dr Cain in his old-fashioned schoolmaster’s costume. What ridiculous sights they both were. What fun they would have together.

“Please sir, have I passed the audition?” he beamed.

“Oh yes, dear boy. Oh yes.”

Peter’s heart raced with excitement. This was turning out to be a summer to remember.


Other stories you might like

The night before Christmas

Don’t borrow dad’s car – take two

Dad’s despair




More stories from Charles Hamilton II are on the MMSA website


Charles Hamilton the Second