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.

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More stories from Charles Hamilton II are on the MMSA website

Charles Hamilton the Second

charleshamiltonthesecond@gmail.com

After the party

The parent-teacher association Christmas party was in full swing in the school hall. Wine was being glugged and cheese snacks nibbled. Adam and Steve, senior prefects and bastions of St Simon’s Independent Grammar School, their hosting duties nearly at an end, hurried away from the festivities.

“Quick, in here,” Adam opened a classroom door and ushered his pal into the darkened room. He removed a torch from the pocket of his fancy green and red school blazer and directed its beam into the far corner. “Look what I’ve got.” He leaned forward and picked up a wine bottle. “Goldener Oktober, Liebfraumilch,” he beamed. “Classy stuff. There’s another bottle there,” he nodded into the shadows. “They’ll never miss a couple.”

He pulled out his Swiss Army knife, cut the metal fastening on the bottle and dug out the cork. Then he raised the bottle to his lips and drank heartily before handing it to Steve. The wine was warm, even though the room was not. Steve shivered as the alcohol hit his stomach. Within seconds the bottle was half empty.

The two eighteen year olds perched their buttocks on the edge of a desk, their thighs touching. Their eyes met. Steve tilted his head. Opened his mouth a little. Leant towards Adam’s welcoming lips. Tongues entwined. Fingers ran through hair. The taste of wine intermingled with tobacco from cigarettes smoked earlier.

Adam pulled away. Couldn’t breathe. Needed air. Lungs once again full, he plunged forward. Cocks ached. Steve tugged at Adam’s belt buckle. Undid it. “No, not here,” Adam pushed his pal’s hands away. Not too vigorously. “Someone might come.”

“C’mon, there all at the party. It won’t finish for half hour at least.”

“Okay.” Adam had no willpower. He loved it when Steve tossed him off. Flies were soon undone and trouser fronts opened wide. Aching dicks strained against white cotton Y-fronts.

“Here, let me.” Steve tugged at the elastic waistband pulling the pants over his pal’s smooth buttocks and liberating the erect penis. Steve’s drowned his tongue with spit, leant forward, made a perfect “O” with his lips and took the swelling member in his mouth.

Mr Doughty, the housemaster of Queen’s, needed to pee. He had drunk too much wine and it was going straight through him. The boys’ bogs were close at hand. He would go there. He lurched down the passageway. It was too dark. He reached for the walls to guide him on his way. What was that noise? It sounded like a screeching cat.

He saw a faint light through the window of a classroom and went to investigate. He peered into the gloom and saw two sixth formers; one lying back across a desk, the other leaning into him with the boy’s cock in his mouth.

Doughty’s bladder was about to burst. He rushed on to the lavatories. He knew the boys. He taught one of them. White. What a delightful boy. His cobalt blue eyes could light up a classroom. His crooked smile melted the heart. Often Doughty dreamed of running his fingers through the teenager’s unruly fair hair.

The housemaster rested his head against cold wall tiles as he directed piss into the urinal, his cock stiffening in his hand.

Moments later he was back at the classroom. He shoved open the door and switched on the lights. “What the … ?” Two terrified pupils, trousers and underpants at their knees, gaped.

“I have never in my life … Words fail me …” the housemaster stared at Steve White’s steel-hard cock. Then, quickly averted his gaze.

“We have guests. Parents. School governors …” Doughty’s brain could not communicate with his mouth. His stomach churned. “My study. Tomorrow morning. Both of you.” He closed the door and unsteadily returned to the party, leaving behind two bewildered schoolboys.

The next day dawned brightly and sunbeams hit Steve in the face as he lay in bed. He had barely slept. His life was about to end. He and Adam had talked about it. Expulsion from school was the least of their worries. Would Doughty tell the police? Steve was too scared to go to prison. Everyone would know. His friends would desert him. God! What would his father say? Or do? Steve might be homeless before the day ended.

Doughty had a bad night too. His wife assumed he was drunk, as he often was. The schoolmaster’s mind was filled with the hugeness of Steve’s throbbing cock. When Doughty reached for it the teenager thrust his hips forward. The hot throbbing prick felt like a velvet covered steel rod in his hand; and, when Doughty started stroking it, Steve inhaled deeply, moaning softly.

Doughty’s own dick stood rock hard and his wife took full advantage.

Hours later, Adam and Steve stood fretfully outside the housemaster’s study. Steve could see his reflection in the shiny brass plate. He knocked nervously, waited for the call, “Enter”, turned the heavy handle and pushed open the door.

It was a large room with a desk in front of a bay window looking out onto the quadrangle. To one side was a two-seater sofa; on the other, a wall of books. There were a couple of straight-back wooden chairs in front of the desk, but the sixth formers knew they wouldn’t be invited to sit. The chairs would have a different function that morning.

Doughty sat in a leather swing chair glaring. The two teenagers stood meekly in front of the desk, eyes downcast at the patterned rug beneath their feet. Neither boy dared look straight ahead. They did not want to meet the icy stare of the housemaster. But worse than that, behind Doughty’s shoulders, screwed to the wall, was an ornate rack containing four yellow crook-handled rattan canes.

The boys shifted uneasily. Behind them an open fire blazed away. The heat was intense.

Doughty’s tongue was stuck to the roof of his mouth. He wanted to rip into the boys and tell them they were “disgusting perverts” but the tongue wouldn’t cooperate, except to make sputtering noises.

Eventually, he formed coherent words. “Revolting,” “Repulsive,” “Disgusting,” “Nauseating.”

Adam and Steve stood in silence, guts churning.

“I have the honour of the school to protect,” Doughty was in full flow now. “If I report you to the police, as indeed I could, it would do irreparable harm to the reputation of St Simon’s.” He watched carefully the boys’ reactions. Both were simultaneously deathly pale and sweating profusely.

“So, I will deal with the matter myself. Here. Now,” he growled.

Steve’s face flushed with relief. Adam stared impassively at his shoes.

“It will be a flogging,” Doughty croaked, suddenly his mouth drained of saliva.

He cleared his throat. “Stand facing the wall. Hands on head.” He watched intently as the two teenagers shuffled meekly into position. With hands on head, the tails of their blazers rose up their backs uncovering their backsides. Steve’s pale-grey trousers clung to his buttocks, so that each cheek was defined, the crack sharply divided by the seam of his trousers. Adam was quite different. His trousers appeared to be a size or two too large. Grey material folded across his backside and it was impossible to see where one buttock cheek ended and the other started.

Doughty heaved himself from his chair and walked to the front of the desk. He lifted the two straight-backed chairs closer to the middle of the room and arranged them so they were back to back. Then, he returned to his desk and reached up to the cane rack. All four canes were roughly the same length, a little over three feet, not counting the curved handles. They were of differing thicknesses and densities. He chose the cane at the top of the rack; it was a dark yellow and a little warped from age and use.

He flexed it thoughtfully between his hands. His mouth dried once more. He wished he had had the foresight to bring a glass of water from the staff common room.

“White. You first. Turn around.” Doughty swished the whippy cane through empty air. It made a terrific whooshing! sound as it went. Every nerve in Steve’s body seemed to him to jangle. Pins and needles shot up and down his arms. Slowly he turned. He saw the wicked rod in Doughty’s hands and the boy’s entire body succumbed to uncontrolled shaking and trembling.

“Stand there,” Doughty pointed the tip of his cane at a spot by the chair. Steve stumbled across the study, unable to fully control his legs.

“Hands on head.” Steve’s cobalt blue eyes dimmed. He couldn’t stop them blinking fast. Doughty stared into the teenager’s open face. The schoolmaster hadn’t before noticed how clear the boy’s skin was. In his present predicament, it was almost translucent. The wretched boy’s long curling eyelashes beat up and down. His usually smiling lips were downturned into a deep frown.

Doughty hesitated for a second, then he reached forward and unfastened Steve’s belt. He sensed the teenager’s shock as he fumbled with his zip and the front of his trousers fell open. Once done, Doughty gripped their back and lowered them to Steve’s ankles. Steve’s eyes closed. Doughy hesitated for another second before he gripped the back of Steve’s gleaming white Y-front underpants, inserted his fingers in the waistband and pulled them down exposing the boy’s limp cock and balls.

Steve opened his eyes in shock. They moistened immediately.

“Kneel on the chair,” Doughy tapped the wooden seat of one, “and stretch yourself across the back and hold on to the other chair.”

Steve stood rooted. He couldn’t move. His legs shook so violently he feared he would faint to the floor. “Get on with it,” Doughty couldn’t stop looking at Steve’s long, thin, cut, cock. Steve didn’t know how he willed himself to move. Soon he was in position, kneeling on one hard wooden seat and stretching across two chair backs to stare down at a different worn wooden seat. His knees hurt terribly.

Doughty walked slowly around the prostrate boy. With his back arched and his legs apart the housemaster had a perfect view into Steve’s hairless crack. The boy’s buttocks were as smooth as a baby’s and his ball sack and cock dangled.

The buttocks trembled and Steve’s hole winked open and shut with nervousness. Doughty gripped the boy’s blazer and tugged it up his back. Now there were several inches of bared back. It was as hairless as the boy’s bottom. Doughty gave the naked bottom a preliminary smack with his open palm. There was a sound of flesh meeting flesh. The bottom wobbled at the contact. Steve, his face in close proximity to the chair seat, gave a sharp gasp. This was mortifying.

used drawing cane hold (28)

Doughty raised his cane. Bent across two chairs, Steve was in the perfect position for his punisher to whip the cane at force into the fleshiest part of the backside. Doughty placed the cane just below the apex of the mounds and rubbed it backwards and forwards. He felt Steve’s body tense. The buttocks clenched. Steve gripped the wooden chair so hard his knuckles began to whiten.

He felt the cane move away from his bared bottom, there was a second or so pause and then an almighty whooshing noise resounded around the study. Steve felt the intense agony a split-second later. It felt like the housemaster had pressed a red-hot wire into his rear. Saliva washed his mouth. He choked. For a moment he feared he would gag and send a stream of vomit across the room. Instead, a deadly howl screeched from his throat. His body shuddered, his hips juddered and his head bounced up and down.

Doughty observed with great satisfaction as a dark red welt formed across the very centre of Steve’s previously snow-white bottom. Suddenly and without warning a tremendous rage engulfed Doughty. How he hated the pretty boy whose arse was now wobbling in agony across the hard wooden chairs. The same boy he had caressed in his dreams.

He raised his right arm high and brought the cane down with tremendous power again and again in mighty strokes. Deep red welts crisscrossed the firm young buttocks and Steve yelled out his torment uncontrollably, tears pouring down his pale cheeks. Lumpy red welts blossomed under persistent lashes from the raging housemaster. Steve yelled in torment, his body flailing as each new cane stroke whipped into his agonised buttocks, now red raw from the relentless bombardment. His crimson bottom humped up and down frenziedly.

Doughty gave him twelve strokes in total. When he had finished a tense silence fell in the study as Doughty’s eyes focused intently on the Steve’s flogged buttocks, the deep dividing cleft, the glimpse of fair curling hair at the confluence with the thighs. Steve silently gulped in great draughts of air, filling his lungs. Tears flowed like a river going downhill. His chin was covered in snot.

Adam stared in wonder. He had witnessed each frenzied stroke of the cane as it cut his lover’s bare arse to shreds. His own head popped as blood thrashed through his body. He could hardly catch his breath. Adam gaped as he watched Steve’s body wriggle and writhe as the teenager fought to come to terms with the agony travelling through his entire body from his savaged buttocks.

Doughty swished the cane though the air and wobbled it in Adam’s face. “Your turn,” the master growled. “Trousers, pants down.”

Adam stood fixed to the spot. Rooted. No way could he take down his trousers. The humiliation would be too great. Doughty flexed the cane between his two hands and stared intently at the school prefect standing before him. Sweat poured down the teenager’s brow, his face was deathly pale. Doughty’s lips curled. He lay down the cane on his desk and silently reached for Adam’s belt buckle. Within seconds, the trousers and pants were at the eighteen-year-old’s knees revealing his rock-hard erection glistening with pre-cum.

Picture credit: Unknown

This story was first published in December 2016.

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More stories from Charles Hamilton II are on the MMSA website

 

Charles Hamilton the Second

charleshamiltonthesecond@gmail.com