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I have just realised that I haven’t done a chatty blog for yonks. Stories always get more hits, and I have posted a few of those since l...

Wednesday, 8 November 2017

Hotel Booking (F/M)

Bit of a strange one this. Pure fantasy, with a twist. Knocked out whilst confined to study during household decorations. I must have been bored. The scenario never happened to me but must be something that appeals as some years ago I wrote a story  Room Service 
in which a young man is thrashed in a hotel room by a predatory male. I reckon it is the anonymity that ticks my boxes. Enjoy as my little prelude to a Christmas message. That, like my next whacking, is just around the corner. Alfred Roy

Hotel Booking


He ordered his second drink and returned to the corner seat. A plush, red leather, curved area that was both comfortable and secluded. That and his second whisky on the rocks induced a pleasant ambience in his being. Nerves, initially consumed in havoc, were calmed and in control. About time he thought. Pulling up in the car park of the well established if discreet town centre hotel, can a town centre hotel be discreet he thought, his nerves and anticipation had been in overdrive. He had spent four or five weeks musing on this meeting and then nervously made contact. The response had induced a further week of frantic e-mails, hasty re-arranged appointments, lame excuses, and finally confirmation. Yes he would meet her at the hotel suggested, yes he would pay the cost of the room in addition to her fee, very reasonable, and yes he wanted the full works. Complete scholastic domination. For two heavenly hours. How he longed for it. But how he had fretted both after the e-mails and the initial telephone call. Worried about so many things. Most allayed now, in this hotel sitting on this comfortable corner seat with his second whisky, less than half an hour to lift off. How and why he had fretted now seemed a little overdone.


She had been so reassuring. Do not worry she said, I have been there before. The rooms are soundproofed and, besides, they know what I do. They are as discreet as me. They do not want trouble. And we will be out by nine and they can re-let the room. Good business for everyone. You can’t meet at your place and I only operate on this basis. Purely professional. So do not fret, do not worry, just meet me at the hotel and look forward to having your bottom smacked. And everything else. It sounds well overdue. Those last few words had tantalised his being long after the one and only phone call had been completed. Look forward to having your bottom smacked. And everything else. How he desired it, wanted it, was desperate for it. Twenty seven and discovering his sexuality. A like minded friend had told him about her. Amazing. She ain’t young or particularly attractive but she is the bee’s knees. Especially for latent schoolboys desirous of his fantasy headmistress. That is what the like minded friend had said and each word etched in his being and stiffened, literally, his resolve to have a session with her. Or, more appropriately, to be sessioned by her. He had got the distinct feeling that in this bizarre tango there was only one leader and it would not be him. Another box ticked, another twitch in his groin. The downside, there is always a downside, she only played at your place or at specially selected hotels. The first was a no-no, the second did not appeal. Initially. It scared him but, as in so many things, fear and desire are a potent mix. He tortured himself for days, fantasised for a few more, and finally phoned her. Yes he had references, important, yes he knew what she did, important, and yes he wanted it. Desperately. He desperately wanted her to cane his bottom. So much so he was prepared to meet someone he had never met in a hotel room he had never visited. And he booked it in advance. Room 223. And if anyone on reception smirked he was not aware of it.


He knew her straight away. Or he thought he did. The reception desk was well in his sight line, deliberate, and the woman making enquiries fulfilled all of his fantasies. Medium height, buxom but not overweight, mid forties and pleasingly dressed and pleasant of face. Every inch a schoolmistress, but a schoolmistress with a touch of elegant frivolity. She looked both fun and severe and he was convinced she must be the lady his like minded friend had dubbed amazing. If she picked up her case, a heavy brown one, and went straight to the lift he would be disappointed. Devastated in fact. The woman on the phone had made it clear, references or not, that this was a first meeting and she would not go to his room until they had met. He held his breath and prayed. But she did exactly that, took a key and moved off to the lift. So much for fantasies. A few minutes after she left a small and elderly lady, slightly confused it seemed, entered the lobby and made querulous enquiries of the receptionist. Something about them not being able to accommodate her Pekinese. He drank a goodly quality of his whisky and said to himself, please do not be her. Please, do not be her.


He was still containing his disappointment when a voice whispered in his ear.

‘Martin?’ It is Martin, isn’t it?’

He froze.

‘You can look at me. I won’t bite.’

He turned his head and held his breath.

‘At least not yet.’

She sat down, drink in hand, and smiled warmly. The buxom woman he had seen at reception. His puzzled expression evoked a response.

‘I always book in. It looks odd otherwise. They have an office where I leave my case. This is non alcoholic, by the way. In case you were thinking.’

He still said nothing.

‘It is Martin isn’t it? Christopher’s friend? I am rarely wrong.’


‘And if I was, well, no harm done.’


‘Just sorry to have bothered you, a smile, and go. But you are Martin aren’t you?’

‘Is it obvious?’

‘Oh yes. Schoolboy written all over you. Your friend Christopher told me all about you.’



She smiled enigmatically and it was a smile that held a hint of promised indulgences. And the words that followed confirmed it. Martin felt stiffening in his loins as he listened. The words were heavenly, a blessed fulfilment of an all consuming desire.

‘Enough to know that I shall have a willing pupil. A very boyish one, if I may say so. I reckon I shall enjoy beating your bottom. I usually do, but it is a bonus to have one so young.’

‘Thank you.’

‘Even if my fee is still the same. One has to make a living.’


‘And you have been beaten before?’

‘A long time ago. At school.’

‘But not since?’



She mused on this word and a silence fell between them. He finished his drink and waited for her to speak again.

‘But you are ready?’

‘Yes. Yes Miss.’

‘Ready to be caned?’

‘I have been ready a long time, Yes Miss.’

As he said this, Yes Miss, a surge fired through his being. He had definitely been ready for a long time and she seemed safe. Safe for an anonymous meeting in an equally anonymous hotel. Never had he felt so excited. His friend said he would, given his personality and desires. And she was good, so it was said. He would have all those desires fulfilled. So Yes Miss it was. And he was ready.

‘I cane hard.’

‘I know.’

‘Very hard.’

‘He told me.’

‘Your friend?’

‘You have dealt with him, more than once.’

‘Then you know what to expect.’

‘I think so.’

Whether he did or not the prospect, and the words, increased the stirring in his loins. He sensed his penis beginning to twitch uncontrollably. She must know, he thought, she must realise what she was doing to him. Her smile said she did.

‘I do not believe in pretending. I like my scenes to be real. A cane should hurt.’

‘Yes Miss.’

‘But it should also excite.’

‘I hope so.’

‘Creating both fear and desire, Martin.’

‘Christopher, my friend, said it did. He said it, you, turned him on.’

‘In spite of my age and appearance?’

‘Because of it.’

‘And you?’

‘Yes. Yes Miss.’

She smiled and as she did so her eyes flashed a glistening warning.

‘I like to please, as well as give pain.’

‘Thank you Miss.’

‘Then I suggest you go up when you are ready.’


‘I think so. The room is only booked until nine,’


‘And neither of us wishes to rush things, do we?’

‘No. No Miss.’

She leaned closer to him and whispered.

‘Then prepare yourself, young man. Keep all your clothes on, for now; I do not like it any other way. I shall do all that is necessary as we progress. I shall look forward to this Martin. I shall be up in ten minutes. Leave the room unlocked, I do not wish to knock, it does not suit my style.’

‘Yes Miss.’

‘And do not be afraid to cry. It often helps.’

As she said this she raised her drink and smiled at him again. He nodded and did as she bid. He finished his second whisky and, slightly light headed and warm, rose and walked towards the lift. He fervently prayed that no one around could see the erection he was convinced trumpeted the promised scene that was to follow in room 223. In ten minutes or so he would be being caned on his bare bottom. For the first time in many years. And he was aching for it. Aching for both threatened pain and promised pleasure.


He stood trembling, hands on head and eyes closed. He had removed his shoes and jacket, as instructed, and the remaining shirt and jeans clung to him in a heavy sweat. He sensed and felt the soft hands undoing the buttons on the jeans and, as they loosened, thrilled at the same hands pulling away nether clothes and tantalisingly caressing lower curves. His curves, ready and willing for what was on offer. In this case a preliminary inspection. That is what she had said as she closed the hotel door and dimmed the central room light. He had gulped and, commanded, removed the shoes and jacket and stood stock still. Eyes fervently closed. And then the hands had started to explore. All was silent, only his heavy breathing and the drift of perfume indicated the presences in the room. Room 223. He sensed, felt, his jeans being pulled down to his ankles and registered the slight touch of coldness from the room on his exposed flesh. Only his legs but soon, very soon, all of him was revealed and sensed the cold air. His underpants, cotton and light blue, specially selected for this mistress were slowly pulled down. His bottom and penis, the latter magnificently erect, were brought into view. He felt so vulnerable, so consumed in all his being. This was what he had so fervently wished for. Controlled, humiliated, exposed. In an anonymous room with an anonymous woman. And she was not there for prosaic sex, the usual coupling. She was there for other reasons and the thought of what would follow, a cane across his eager bottom, increased that magnificent erection. Martin, partially naked and tantalisingly exposed, wanted all she had to offer. To his friend Christopher he offered many silent thanks and sighed. The sighs died when soft and caressing hands ceased their exploration and a large and heavy strap whacked into his naked and trembling behind. Martin’s discipline had begun. His anonymous mistress in the anonymous hotel room did not disappoint. Standing still, hands on head, he absorbed twenty or so strokes of her straps across his bare bottom. They neither decreased nor enhanced his erection. They merely complemented it. The feeling was heaven and when she pulled his underpants over his burning bottom Martin wondered what was to follow. He did not have long to wait. Instructed to pull up his jeans he did so and, breathlessly, followed all else she said. He bent over the chair she had placed into the middle of the room and readied himself for a promised cane. She gave him twenty four strokes, six on his jeans, six on his underpants, and twelve across a behind she lovingly bared again in preparation. They stung like hell, especially the last twelve, but Martin drank them all in and willed it to continue. Never was pain so pleasurable, none more so than, when bid, he looked into the hotel room mirror and admired the savage weals burned into his glowingly warm backside. ‘Touch them’ she said, ‘Enjoy the warmth, the ridges, the sting. And when you are ready Martin, strip’. ‘Strip completely, I wish to see you as you wish to see yourself. Naked.’ And she did. And for over an hour more a naked Martin suffered and devoured exquisite humiliation that even his fevered imagination had not contemplated.


They sat in the bar of the hotel, the three of them. Martin, his amazing Mistress, and his friend Christopher. The session in room 223 over, Martin and his tormenting chastiser had retired for a relaxing drink. Alcohol, she had said, this time, and her smile alluded to the possibility that Martin had quite exhausted her. Perversely, a subdued Martin seemed pleased. The bar lounge was empty and conversation, albeit subtly low key, could be free and uninhibited. It was during a few intensive exchanges that Christopher turned up, clearly expected if not by Martin. He bought a drink at the bar and joined them. If Martin was surprised by this it paled into insignificance as a strange three way conversation progressed. A conversation that both churned Martin’s stomach and, weirdly, disturbed and enhanced his pleasure of the evening. If he never knew before how perverse his sexuality was, he certainly did now.

‘Your wife?’

‘Yes. Did you not guess?’

‘No, why should I?’

‘No reason Martin, I just thought you might though.’

‘My names is Christine, by the way.’

The woman who had just done things to him he had only dreamed of, in an anonymous hotel room, turned and smiled at Martin. She sipped her drink and continued.

‘Christopher had told me all about you and, well I thought it might be fun.’

‘So you don’t normally do this sort of thing?’

‘Oh yes. It’s my living. And my pleasure.’

She smiled and looked at Christopher.

‘And she is very good Martin, isn’t she?’

‘Yes. Yes, she is, very good.’

His mind wandered back to hotel room 223 and he blushed, beads of sweat returning.

‘And you don’t mind?’

‘No. Should I? After all, it is how we met.’

How they met. Christopher and Christine. At a dominatrix party, a couple of years before. They clicked and, strangely, fell in love. A normal relationship Christopher said, except once a week or so when she beat him. And except those weeks when she sent him to someone else to do the same. It was at one such someone else’s house, an afternoon party, that he had met Martin. A voyeur, a man on the side, watching but desperate to be involved. They became friends and, eventually he told him about Christine, Madam Christine. Except he did not say her name or that she was his wife. Merely of what she did.


And it was what she did that Martin was still thinking of when he journeyed home. Christine, his friend’s wife. What she did for a fee, a substantial fee. And for pleasure she had said. Did Christopher know? And if he did, did he care? Did he know or guess that his wife had taken Martin, a man much younger than himself or her, to a hotel room. And in that hotel room she had thrashed him, caned him, made his bare bottom beetroot. And when she had done so she had stripped him naked, tied him to the bed, spread-eagled, ran her hands all over him and brought him to a climax that Martin had only previously imagined. Her feverish hands and his throbbing behind had combined in releasing an explosion of perverse desire from his bursting cock. Never had he come so willingly and so desperately. The experience was wonderful, and the reliving of it with his new found knowledge even better. He already hankered for a repeat. Christopher was a friend, a like minded friend and, as Martin told him in a pub a couple of weeks later, being beaten by his wife was an amazing experience. Christopher smiled. No bother, he said, and next time, if you want a next time, she might do it for free.

‘Providing you let me watch.’

‘Let you watch?’

‘Yes. Does that bother you?’

‘No. No, strangely it doesn’t.’

‘That’s what Christine said.’


‘She said, and she knows these things, Martin has an exhibitionist’s bottom.’


Martin just laughed, laughed to cover his embarrassment. But he knew Christopher was right. His penis had never stopped twitching from the moment he met Madam Christine. He fervently desired her to thrash him again. Discovering she was Christopher’s wife did not diminish his feelings, it increased them. And now, in the pub, with the strange proposal? Martin twitched even more. To have his humiliation watched took strange desire to new heights. Even higher than room 223 in an anonymous town centre hotel. He could not wait.

To be continued


Alfred Roy (2017)






















Saturday, 2 September 2017

A Caning From Three Angles (M/m)

A little while since I posted. Have been busy but, as new photo at the side shows, found time to indulge in a favourite hobby. Much justified seeing as hits on this blog now total 200,000. I find it pleasing that so many people enjoy the same strange passion as me. When I was young I thought I was the only one. I mean, how can anyone really enjoy being caned on their bare bottom? Lots of us as the internet  regularly illustrates. Long may it continue. If anyone has found any better fun than dropping your pants to be whacked then I have yet to discover it. Age limits activity these days but writing stories, such as below, compensates. Never happened to me but I can fantasise. An F/M story next time - Hotel Appointment. Like to keep all the folks happy. 200,000 times apparently. Alfred Roy

A Caning From Three Angles

The Headmaster’s View

It has to be done. The boy deserves it, far more than most. A particularly nasty piece of work. Bullying minors and blackmailing them. I rarely sanction canings but this one was an easy decision. Either this or being expelled. Or both. No, I settled on the caning but make it a harsh lesson. That was my decision. Reading the report on his crimes made that decision easy. Eight strokes. Eight strokes on his bare behind. That would teach him. So I thought. Until I saw him. Now. Standing here in my study. He looks so young and vulnerable. So innocent, so scared. Have I misunderstood?


The Games Master’s View

Thank God he agreed. I thought for a moment he was going to decline my recommendation. Going to suggest that the boy should be suspended or, even worse, just given a detention. No sir, no headmaster, he deserves a good thrashing. A few strokes of a cane across his backside, preferably a dozen, preferably bare. Show the little bastard that we do not condone his actions. And I will do it, willingly, it is well overdue. He looks like an angel, standing there, but do not chicken out. This little beggar deserves everything he is going to get and, by God, I shall enjoy it. That bum is going to be very sore if I have any say in it. Even if you relented to only eight. I shall make them feel like twelve.


Master Andrew’s View

Not much chance here. The headmaster is a wimp; he looks more scared than me. And that gym master is a bastard. Been itching to whack me all year. Probably wank off to it afterwards. Especially as he got his wish. I have asked the headmaster to agree to your pants coming down, he had said. A bare arse thrashing boy. I was supposed to be impressed, supposed to plead. I spit at him. See you in court I said. He repeated it. Bare backside, eight strokes though I reckon you deserve at least twelve. How he enjoyed keep saying it. Your pants are coming down boy, your pants are coming down. Tomorrow. If he doesn’t bring himself off at the thought probably the headmaster will. Me? I have had worse. And now I am here, in the study, and hate and fear are eclipsed by a surfeit of despising. Just get it over.


The Set Up

The headmaster sipped his glass of water. How he hated situations like this. A young boy trembling. A master fired up with indignation and revenge. And himself, arbiter of an unpleasant task he would wish left to others. Corporal punishment was rarely sanctioned these days. Almost outlawed, but not quite. Reserved only for the most serious cases. And this one was serious, so much so that he had agreed with the gym master. Yes the boy could be caned. Yes he could be given the maximum of eight. And yes he could have his pants taken down. It was still allowed at a private school. Even if not condoned. But all apprised of the circumstances would agree. He thought. Would agree that the boy’s pants would have to come down. And, naturally, he would have to be there. To watch, to ensure fair play. To ensure no overstepping of the mark. No going too far when a boy was caned on his bare backside. This boy. Trembling and nervous. The first to suffer such for at least three years. He had shuddered when the gym master said this. Three years since we sanctioned such a punishment. Almost an attempted rape that was and the instigator was subsequently expelled. Only a nicety in the procedures had allowed him to be caned first. Much deserved. But this boy, this boy, was his sin so bad?

Yes headmaster, the gym master had said. Bullied twelve year olds and threatened them if they did not pay him protection money. A nice little scam, a nice earner, for a year or so until one of the little ones absconded and revealed all to his distraught parents. Deserving of being expelled but a caning first. Or as a substitute, a reprieve. He didn’t care as long as his sturdy cane whacked into that boy’s bottom around a dozen times. Long desired to do it but never dared. This was his chance. If not twelve then at least eight. And pants down headmaster. Make him suffer as he made the juniors suffer. Make him feel something he will never forget. And then expel him if you want to. Send him away with thick and fiery red stripes across his rebellious arse. Will be an hour well spent.

He told the boy of the headmaster’s decision. He never flinched. Five and a half feet of pure, sixteen year old, venom. He and the gym master loathed each other with a passion. Got your wish, he said. Always wanted to get my pants down, he said. And the wimp has agreed. Surprised you haven’t got a hard on, or maybe you have. The gym master refused to rise to the taunting bait. His hour would come when this boy was bent over, trousers and underpants down, awaiting his cane on his bare flesh. He could wait and the boy knew that. False bravado ahead of a daunting experience. He spat in the face of the threat but inwardly quaked. But whatever transpired he was determined not to cry. He hated the bastard of a gym master and despised the wimp of a headmaster. They might see his naked bum but they would never see tears.


The Preparation

It was all so classically evocative. The diminutive and venomous Master Andrew, eyes ablaze with a mixture of fear and loathing, the sadistic Games Master rich in eager anticipation, and the tall and perturbed Headmaster weighing up justice with humanity and order with excess. The boy had to be caned, as decreed, and he had to be caned on his bare backside. As persuaded. But if the Games Master was bent on a private vengeance, long festered, he was there to ensure the ultimate sanction stayed within acceptable bounds. In a study rich in leather bound furniture and washed with afternoon sun, he laid out the inevitable procedure. Long and tortuous it seemed to a boy with a twitching behind and a games master holding a twitching cane. If the one feared, in spite of his outward bravado, and the other relished, both combined in wishing that the punishment would soon commence. The boy in hope it would quickly be over and the master in equal and fervent hope that it would be as imagined. The prolonged peroration, delaying to both the inevitable tableau to follow, was a headmaster using words to steel his resolve and allay his doubt. It was only five minutes or so from the boy entering the study to bending over the low backed leather chair but it seemed like an eternity. Never were words so unnecessary and wasted.


The Dialogue

The Headmaster spoke.

‘You know why you are here boy?’

‘Stupid question.’

‘Do not be insolent boy, you will only make things worse.’

It was the Games Master who spoke, relishing the expected insolence.

The headmaster again, surprisingly apologetic.

‘I just wish to be certain you know why you are to be caned, that is all.’

‘Because I got found out, because some brat blagged to his folks.’

The headmaster studied him and absorbed his response. Sympathy was rapidly dissolving.

‘Do you feel no remorse?’

‘There is only one thing he will feel, Headmaster.’

The Games Master again, impatiently tapping the cane against his right thigh.

‘Let him answer. Well, do you?’


‘Good, that is progress.’

‘For being found out.’

The boy spat out the words and followed with a few more.

‘Unlike all the other bastards who have been doing the same for years. But he likes them; he turns a blind eye to them. It’s only me he wants to get.’

‘That is not true, Headmaster. I have no agenda.’


The boy spit out the word and the Headmaster flinched.

‘It’s bollocks. He has been itching for an excuse to cane me for months. That little oik gave him one.’

The Games Master again.

‘I have no agenda, Headmaster. I agree that I have long felt that this boy deserves to be taught a hard lesson. Which is why we are here. But it is not personal, definitely not. It is only what is deserved. Deserved and just.’

The Headmaster sipped water from the glass on his desk and pursed his lips. Combining thoughts and words were proving difficult.

‘Putting aside this perceived animosity do you accept that what you did was wrong? Threatening younger boys and stealing money from them?’

‘I didn’t steal. They gave it to me.’

‘In return for what?’



This time it was the Games Master uttering the expletive.

‘He was running a protection racket, Headmaster. If they did not give him cash he would beat them up. We are wasting time. He deserves to be thrashed and he knows it.’

The Headmaster pursed his lips again.

‘Is that true?’

‘Of course it is true, and that little shit knows it. Don’t be deceived by the angelic face.’

‘Language, Master, language. I repeat, is it true?’

The boy considered before answering. To deny was to prolong and, although fearful of what was to be done, he wished it over. Just so long as he did not cry. He did not want to give that satisfaction to a man he hated.

‘Yes. Yes it is true. They paid me so I would not beat them up. But I am not the first, or the last. Just the one that that shit, that shit, wanted caught.’

‘Then you leave me no choice.’

As the Headmaster said this there was almost a hint of regret in his voice, a hint that the Games Master was determined to extinguish.

‘There you have it Headmaster. Out of his own mouth. His own words, so perhaps we can now get on with what we are here for.’

The cane tapped impatiently, yet again, against the twitching and rigid right thigh.

‘Yes. Yes. Of course.’

The Headmaster took a deep breath.

‘You will be caned, Andrew Bailey. Caned for a heinous offence. It is with regret but with justification that I sanction it. Your Games Master, Mr Bennon, will administer the caning. Eight strokes.’

‘Think yourself lucky, boy. I wanted twelve.’

The Headmaster ignored the interjection.

‘Eight strokes of the cane on your buttocks. The normal punishment at this school. But in view of the seriousness of your offence...’

‘That bastard gets his wish.’

‘Quiet. The Headmaster has not finished.’

‘In view of the seriousness I have agreed that the caning shall be delivered to your naked backside. I would therefore ask you to prepare yourself and bend over that chair. The sooner this is over the better.’

A moment of silence as all absorbed the fateful words.

The boy gulped but hid his nervousness. He knew it would come to this and he was not looking forward to it. Putting aside the humiliation of taking his trousers down and showing his bare bum the thought of that cane hitting him eight times was loosening his bladder. He was scared but he would not show it. Not to that shit of a Games Master. Just do not cry he said to himself. Anything, any pain, but that.

The Games Master felt a surge through his being. The Headmaster had said it at last, eight strokes with pants down or words to that effect. The warm surge thrilled his body and the look on the boy’s face, anxiety tinged with contempt, thrilled him even more. Imagination was about to become reality and if he stiffened in contemplation it was hardly surprising. But for the next few minutes, heady with anticipation, control was all.

The Headmaster breathed deeply and pursed his lips again. The boy’s gaze was unnerving and the Games Master was visibly twitching. He prayed that he had made the right decision.

‘Take down your trousers boy. It is time you were caned.’

Any of the three could have said that.


The Caning – The Headmaster’s View

Take down your trousers boy; it is time you were caned. He had uttered the words he had been rehearsing all morning and their effect was electric. What had been promised was about to be delivered. There was no going back, all three knew that. He watched, mesmerised, as the boy shrugged and approached the leather chair. Only the combined heavy breathing of the three broke the enveloping silence. The boy, face set grim and determined as he struggled with the buckle on the belt of his trousers. The Games Master, eyes ablaze and body stiffened with eager anticipation. And he himself, transfixed by the scene evolving before him in his study. A boy, a boy he had decided he did not particularly like but a boy all the same, was about to be caned on his naked bottom. And he had sanctioned the man at his side, determined and ready and vengeful, to administer it. He watched as the boy loosened his belt, undid his trousers and pushed them down to his knees. He sensed the keenness in the Games Master growing and inwardly resolved to ensure that this caning, however deserved and however severe, remained within bounds. It was to be eight strokes across the boy’s buttocks, nothing more nor less. He would ensure no loss of control. The boy hesitated before bending over the chair as if coming to a decision. He guessed at what it was and the following action confirmed it. The boy pushed down his underpants to his knees and, contemptuously and almost provocatively, pulled up his shirt to his waist and bent over the back of the leather chair. Presenting an almost studied central nakedness which indicated that his backside may be about to be violated but he retained some control, some strange dignity. It invoked a grudging admiration, in him if not in the Games Master who snorted at such at an action, at such a display. Wishing no doubt, he thought, that such revealing action was a key element of the drama that the Games Master had intended for himself. No matter all was now ready and he watched as the bending boy was approached and the cane which had twitched in readiness from the first moment pressed into the naked bottom. When you are ready Mr Bennon, let us get this over with. Eight strokes, no more, as we agreed.


The Caning – The Games Master’s View

When you are ready Mr Bennon. Of course I am ready. I have been ready ever since this little oik entered your study. Given his small frame and angelic looks I feared for a second that you might let him off. Until the shit opened his mouth and condemned himself. He’s scared now, I can tell, in spite of that grim face. He knows I am going to lay on the cane as hard as I can even if you don’t. But I shall keep control, shan’t give you any reason to relent even if he screams his bloody head off. I’ll make sure every one of those eight strokes will be across the centre of his pretty little arse. I have been practising, been waiting, been wishing this opportunity. I shan’t screw up. And as a bonus I have to say it is a nice arse. Small and tight and very boyish and, thankfully, as clean and pure peach as I could wish. A boy’s arse absolutely designed for a caning, for having livid red stripes across it. Oh, how I shall enjoy this. Pity he pulled down his own pants, I was looking forward to that, looking forward to showing him who was in charge. But, no matter. He did himself no favours with the Headmaster in exposing himself like that, pulling up his shirt and almost waving his tiny cock at us. A late two fingered salute no doubt. But at least he has bent over, not resisting like I thought he might, and that delectable naked arse is twitching in anticipation. Not so much as me, as I am sure he knows. I am going to enjoy this Headmaster, and yes I am ready. I place my cane across Bailey’s naked bottom, let us call it that, and take a deep breath. I have waited so long, so long. Even if it is only eight.



The Caning – Master Andrew’s View

Take down your trousers boy, it is time you were caned. Pompous git. Nervous as well. Hey, it is me being caned, not you. Reckon he wouldn’t be so nervous if I was getting them on my trousers and a less sadistic beast was doing it. I am ready anyway, ready as I can be. Eight strokes across my bare bum. Does not bear thinking about, so I won’t. But shan’t give them any pleasure, especially that bastard of a Games Master. Hide the twitching, hide the nerves, hide the filling bladder desperate to pee. Just get on with it I say. I shall pull my own pants down, everything, and pull up my shirt. Show them I do not care, that I have nothing but contempt. They can have a good look at my bum and my cock and my balls and reckon on what they are doing. And I will not scream, I will not cry, I will take that bastards eight strokes on my bum and then get out of here. I will not be humiliated either. Showing my bits is no big deal, even if that nasty cane cutting into me will be. It is soon over, I hope. Bending now, sticking up my bum, begging him to whack it. And he will, especially as I am sure he has got a hard on. Pervert. Oh, God, it is touching my bum. The cane. And it feels so cold and hard on my bare skin. I must not cry. I tell myself, whatever else, I must not cry. I can see the Headmaster standing to my right. Catch his eye. I must not cry.


The Caning

It was as all had anticipated. The Headmaster, the Games Master, the Boy. The classic dance, age old, played so many times over so many years in so many places. A boy bent down, in this case over a chair, trousers and underpants around his knees and bare bottom sticking provocatively into the air. A man, rigid and stern, standing to his side and slashing his cane across the twin orbs of the twinkling boyish buttock cheeks. Creating a picture of livid red stripes that induced both anguish and appreciation. Anguish from the one suffering and appreciation from the one administering. And the arbiter, the one watching, ensuring that all was in acceptable bounds. In this case eight strokes, no more, and all delivered centrally across the boy’s two cheeks.

Thwack, thwack, thwack, thwack, thwack, thwack, thwack, thwack.

It does not sound much.


The boy squealed, in spite of himself, and the headmaster flinched.


The boy squealed again, the headmaster flinched again, and the games Master admired the growing red stripes.


Will he rise, he is struggling, and that was the hardest yet.


That was good, he squealed so loud I thought he would rise. The Headmaster is transfixed; he cannot take his eyes of the boy’s bottom.


Aaagh. That was vicious, all agreed. Wriggling, squirming, surges of desire from the wielder, a mesmering fascination from the Headmaster. It cannot stop. It will get harder.


It did. The Boy screamed, half rose, A trickle of blood on the edge of the the deepest red weal. The games Master sensed, almost felt, the pressing of his erection. The Headmaster groaned but did not move. The boy started the gentlest of whimpers as the blood trickled down his naked thigh.


The boy screamed again, and screamed even more, begging to be let off, rising, pushed down, one more to come. The Headmaster agitated, wandered around, drank in the naked bottom, waited. The Games Master pressed the hand holding the cane against his groin then raised it for the final time.


Aaaaaaaagh. Screams. Tears. Abuse. Rising. Clutching buttocks. Swearing. No more. No more. No more it said. You have won, you have won, you bastard. The Games Master stepped forward, cane raised, grabbed the boy’s shirt. Lifted it high to his shoulders. Ready to strike again. The Headmaster, the wimp, the prevaricator, stepped in. Eight. Eight he has had. We all three need to calm down.

And they did.

Thwack, thwack, thwack, thwack, thwack, thwack, thwack, thwack.

It does not sound much.

But it is.



The boy stood by his mirror in his room. Tears in his eyes. He had failed but with some justification. The pain had been excruciating, he had almost passed out. But he had not cried off, until the end when the last vicious stroke had cut into him. So he smiled and lowered his trousers and his underpants and turned around. He studied the eight livid weals across his behind. They would be there for some time. All eight. Evenly spaced marks across both of his small cheeks. Raised, hard, vivid, and purple. Turning black at the centre. He touched them. Scabby. His fingers moved and contrasted the feel with the smoothness of his untouched skin. Eight strokes, parallel lines, only an inch and a half or so from first to last. That Games Master knew his trade. It was a caning he would not forget. His bottom, still hot, said so. He pulled up his pants. Two hours later he lowered them again and looked again at the stripes. And this time, this time almost in defiance, he masturbated. Brought himself off.

Elsewhere in the school, separately, as imaginations were fuelled and situations relived, two others were doing the same.


Alfred Roy (c) 2017





















Wednesday, 7 June 2017

The Retired Headmaster (M/M) - with accompanying picture

This story is self explanatory. The preamble should make it clear. In reality I thought I was going to meet up with such a person during the spring months. It did not happen, sadly. However I did manage to make a visit to an old friend and we created the situation I had desired with someone new. The photo on the side is the result. No longer a thirty year old bottom, as per the story, but one that thoroughly enjoyed  being whacked. One may be getting old but one can still enjoy this most delightful of perversions. Enjoy the story, even if you have to avert your eyes. Alfred Roy

The Retired Headmaster


It’s a phrase that always caught my eye and created a tingle elsewhere. And if I followed it up, a spring infused my steps. Retired Headmaster. Just two words, but two words rich with special promises and pleasures. Met one or two in my time. Whether they were real headmasters or no, I cared not, the soubriquet was enough, especially if they looked the part. Have been hankering recently to again meet up with one of those like minded folks who still promote themselves as such but distance and obstacles have so far thwarted. It hasn’t stopped me thinking that such a visit is long overdue. Headmistresses, retired or not, don’t come cheap and the male of the species often perform their pleasurable tasks for free or just a nominal sum. To someone who cares little who bares his behind and stings it, as long as it is done with expertise and relish, the situation is a no brainer. So I shall continue searching and hoping and, in the interim, muse on a Retired Headmaster experience I had some years ago.

He was a fussy little man, dapperly dressed in three piece suit and bowtie, and reminded me more of a floor manager at an expensive department store than retired headmaster. But he had a malicious twinkle in his eyes and a warming smile when he discussed the afternoon arrangements. Both facets set me at my ease and suggested promise. We had communicated a couple of times before meeting. I travelled a lot in those days and his palatial detached house, so he told me, was only a short detour on my regular journeys along the A1. The Great North Road. I could call in on my way back south in a summer heat that was heavenly both for the warmth and the adventure. My northern meetings had been dreary but necessary and it was only the thoughts of our meeting that kept up my spirits. Hardly surprising. I had been put in touch with him by a like minded friend and our couple of telephone chats established a rapport. He liked caning bottoms and I liked mine to be caned. As a schoolboy. We could be made for each other he said, and chuckled. His parting words, as we confirmed my visit, lingered throughout my business trip and haunted every free moment. I shall take down your pants of course, he said. All boys should be beaten on their bare bottoms. Yours will be no exception. I said I would not have it any other way. Headmaster or not, retired or not, he certainly ticked all my boxes.

Such anticipation, of course, can frequently lead to disappointment. It had happened to me a couple of times. I once, famously, spent seven hours in travelling for six of the best on my shorts. All over in five minutes. That was it. The man who did it was happy. I wasn’t. He had not stirred from his house. I journeyed home, three and a half hours, with a slight sting in my bottom and a strong feeling of frustration in my head. Could this be the same? A week or so spent in anticipation for five or ten minutes of fleeting pain and little pleasure. I sincerely hoped not. I reckon that seven hour jaunt, and other experiences, was why I turned to professionals. Male and female. At least with them you get your sixty or ninety minutes. They earn their fee. But amateurs, I use the word kindly, can be unpredictable.

I need not have worried. From the first tentative knock on door, the house was all he said, and the warm handshake I sensed we would gel. Long journey, he said, let us have tea and talk. So we did. I told him my desires and fantasies and experiences at school, the latter particularly intrigued, and he told me what he intended to do. Allow an hour, he said, I have no wish to rush. That appealed. No seven hour frustration here, I thought. I had bought my PE kit, white top and shorts as he had requested, and changed into them after the refreshing tea. Leave on your underpants, he said, you may need the extra protection. And then he smiled. Do not worry, they will be coming down. I tingled and, hastily changed, went to the room he indicated. A headmaster’s study in all its splendour. A large desk and equally large leather chair. A small bench on which, attired as ordered, I sat and lots of impressive bookcases. And in the corner, near latticed windows, a stand full of various implements. All designed to mark a behind. I waited for about ten minutes and, shamefully, played with myself in anticipation. Only through my shorts and underpants but, waiting, my desire was clearly strong. I prayed he would not see.

I should make it clear at this stage that I looked every inch the schoolboy. I was in my mid thirties, slightly built, and with a very young face. My love of corporal punishment had been kindled at school and flowered through my twenties. I was, and still am, fortunate in that my bottom matched my face. Young and boyish but deceptively capable of taking severe cane strokes. Made me popular at the caning parties I regularly attended in those days. In anticipation of my meeting with this retired headmaster I had refrained from any indulgence for a number of weeks. Most caners that I know and knew appreciate a virgin, unmarked, bottom and mine was pristine smooth, hairless, and unblemished. Every inch checked in bathroom mirror, and every inch ready and eager to be painted in scholastic stripes. No wonder I was playing with myself.

He caught me. I was so absorbed in my lower fumbling I did not hear, or see, him enter the room. His manner had changed, stern had replaced fussy and steel supplanted warmth, and I guiltily blushed as he bid me stand. He expressed disgust, naturally, but secretly I reckon he was pleased that my furtive actions had introduced a verisimilitude to our preambles.


‘Do you usually indulge in such disgusting habits?’

‘No, sir.’

‘In the headmaster’s study?’

‘Yes sir. Sorry sir.’

‘You will be boy. You are here to be caned as you know. Gross insubordination. In view of your unseemly behaviour I shall increase both quantity and severity of the cane strokes. Do I make myself clear?’

‘Yes sir.’

‘I think twelve strokes, six on your shorts and six on your underpants will suffice for the insubordination and then a further twelve on your bare behind for this latter offence. Do you agree?’

‘Do I have a choice sir?’

‘Do not get glib with me boy or I might have those shorts down straight away and give you them all on your naked backside.’

‘Yes sir, sorry sir.’

‘Yes sir, sorry sir. How many times have I heard boys say that when they know that their bottom is about to be beaten. It’s too late to be sorry, too late. It is time to bend over and take your punishment. Punishment well deserved and punishment delivered to where nature intended. To your bottom. A bottom that will be very red and sore by the time I have finished. Bend over and touch your toes.’


He was in full stride through all this, pacing and pacing up and down the room. I stood transfixed and a little thrilled. As the pacing increased he crossed to the latticed window and selected a cane from his copious selection. It was red, medium thick, and made for a goodly swish as he flexed it. He amplified my thoughts when he referred to it as a senior cane, redwood, designed to sting the most obdurate of behinds. His face was flushed and his eyes gleamed in anticipation. Bend over, he said, touch your toes or grasp your ankles. Six strokes boy. His voice was thick and, as I replied and did as instructed, my own was almost as breathy. I couldn’t touch my toes but I did manage to grasp my upper ankles and keep my legs straight and steady. I was conscious of both my upturned bottom and, reassuringly, the fact that it was covered by both shorts and underpants. That cane looked vicious. I was both headily expectant and slightly scared, both feelings enhanced by the thrill I felt when large hands explored my covered rear. He may be a retired headmaster and I a naughty schoolboy but, prior to delivering his first set of stings, fantasy allowed a short sexual frisson that reality would frown upon. I sighed as those hands explored all of my nether curves. My bottom cheeks, my crack, my testicles and penis, all felt the clothed touch of exploring hands. Did he do this when he was a real headmaster? Did he desire to do it and resisted? Was he at last fulfilling suppressed passions? I cared not. All I thought was do not stop, do it more, cane me, and then when my pants are down do it again. When the redwood cane touched my bottom for the first of my first six I was as stiff as the hardest pole.

When it landed, hard and straight across the centre of my clothed bottom, I was not so keen. It stung like hell and the fiery line engendered caused a shuffling of feet and a reaching forward. Hold still, he said, clearly consumed by the corrective act. I did, manfully and painfully. The line throbbed and I knew I had been caned. Albeit only one stroke. Two and three quickly followed and I gasped at both the intensity and the residual pain. My poor bottom was developing an all consuming heat and staying down, ankles grasped, was proving difficult. Retired or not, true or not, this headmaster certainly knew how to cane a boy’s bottom. I readied myself for strokes four, five, and six and prayed they would be quick and accurate. The pain in my rear was eclipsing all other thoughts and desires. My penis had flagged, my breath had exhausted, and the burn on my cheeks was excruciating. I closed my eyes and beseeched those prayers. It did little good. The latter strokes stung and burned and my discomfort rose to new levels. But I remained submissively down and pain eased as a short intermission was followed by exploration of my ravaged backside and the gradual lowering of my shorts. That was perverted bliss. Resting, as they were, on my ankles I was now conscious of hands exploring my tight fitting, and thin, underpants and my increased vulnerability. The burning bottom and eager, manly hands, returned my penis to its earlier full state and flagged a silent acknowledgement that the second six strokes should be delivered. He took his time. The hands explored for what seemed an eternity. But I was not complaining. The burn in my bottom had moved from discomfort to pleasure and the hands, and my submissive position, merely enhanced it. As manly fingers and palms caressed filling balls and throbbing cock of eager student, a side benefit one could say, a small and slightly covered bottom was indicating its readiness for more of the same. Six more cane strokes, six more as hard as you can, but this time on buttock cheeks only thinly protected. He needed little urging. Silence was only filled by heaving breathing. His palms stroked and lingered on my heated curves for just a few moments longer and then, pressing my back and urging me to straighten my legs, he lashed six fairly quick and hard strokes of his redwood cane across my ready and upturned bottom. I gasped, I squirmed, I edged forward, I did not rise but continued grasping ankles, I squealed out loud, and finally I rose clutching my savaged bottom and howling. It had hurt, by God it had hurt, and I could see from his smiling face that he was well pleased. He was well pleased and I was well tanned. So much so that, burning rear notwithstanding, all in front had yet again flagged. Two minutes of cavorting and vigorous rubbing ensued and then a comment, many comments, that continued both the pain and thrill of a heady afternoon of scholastic fantasy.


‘I see that my ministrations have, once again, removed your erection.’

‘Yes sir. That second six really hurt.’

‘So I see. The next twelve will be even more painful. Over my desk, I think. I cannot see you holding ankles for those.’

‘No sir.’

‘Especially as those underpants are coming down. Bare bottom boy. Twelve strokes of my redwood cane on your bare bottom.’

‘Yes sir.’

‘Yes sir, no sir, yes sir. Is that all you can say? No matter. Your little penis will no doubt rise again, in fact I think it already has, but twelve hard strokes across that bottom will expunge all that. But given its manifestations I reckon it is time I saw it.’

‘Yes sir.’

‘That and your little bottom of course. Given my exertions I have earned that right.’

‘Yes sir.’

‘Then hands on head and stand up straight. I want no distractions.’


And he didn’t. I placed my hands on my head, stood up straight, closed my eyes, and waited. Five seconds later my underpants were pulled down to my ankles and large hands explored my blistered backside and my, by now, full and urgent balls and cock. I was in heaven. They say pain comes before pleasure, pleasure follows pain. This was writ large in this anonymous house on my long journey home down the Great North Road. I had been caned, a hard twelve strokes on my covered bottom by a retired headmaster who, before this day, I had never met. And now with shorts and underpants at my feet I was being explored in the most intimate way. I sighed and gasped as large soft hands stroked my very private parts and then gently turned me round to inspect and explore my lacerated bottom. Fingers tantalisingly traced the weals on my backside, followed by a gentle rubbing of palms on the same burning skin. I closed my eyes and drank in the twin sensual pleasures of large hands on my bottom and twitching cock in front. I prayed I would not spurt before the pain I had to come. Twelve hard strokes of that redwood on my naked bottom. The thought made my penis twitch again and it was almost with relief that I was bid to lay over the desk. It had been cleared of all paraphernalia and the smooth leather studded top did not cause discomfort. I stretched my arms, as instructed, and gripped the far side. The action caused my white PE vest to rise up my back and emphasised my lower nakedness. Shorts and underpants were still at my feet and as I waited they were removed. To allow me to stretch my legs he said. They allowed much more, so much more. He wanted my legs stretched wide and, lifting the vest, my back and bottom arched. I could not see the final picture but I could imagine it. Naked, except for the small vest now pushed to my waist, my small buttocks were accentuated and ready to be thrashed. And in between my genitals were exposed and vulnerable. A true boyish picture for a headmaster, retired, to fulfil his own desires. And I had no complaints. It was all I wanted. Providing the cane, already experienced on covered bottom, connected only with my bare cheeks, I could endure. However painful. I closed my eyes and sensed the cold cane pressed against the centre of my bottom. A bottom already well striped and still warm. This was it. This is what I had travelled down the Great North Road for. This was my all consuming wish. A savage cane to lash my bare backside, and to be done by a man who desired the same even more. A match made in heaven. He did not disappoint. My retired headmaster, or at least for this blissful hour or so, did what he had promised and threatened. He thrashed that cane into my exposed bottom the twelve expected times. Each stung like hell, each created its own particular fire. Most across the centre of my bum, but some slightly higher or slightly lower. But all in the area of the buttock curves and none stray enough to cause alarm. He knew his job, he knew his target. What had he said? The area that nature intended, or something like that. He was experienced, he was good, and he was enjoying himself. Ten or fifteen seconds apart each vicious stroke caused a resounding thwack on my naked skin and each made me gasp and squirm. But I suffered it all, gritted my teeth, absorbed the pain, stared at his latticed windows for relief, and gasped breath and shed tears. Not many, but enough to know that my bruised behind had sent the appropriate message to my brain. The last two were harder and quicker, he sensing perhaps my weakening resolve, but the task completed he sighed and tapped my legs with the implement of much discomfort. All done, he said, well done, he said. No blood. I said nothing. I just lay there, across his desk, naked and beaten and serene. Strange? Yes, but strange in the way only those who seek such pleasures can understand. He understood, my retired headmaster, he understood. And I understood him. I had taken his gift but, in doing so, had returned it. I sensed that we were both happy even though only I, as is usual in such cases, only I had a very sore bottom.


‘You took that extremely well.’

‘You gave them extremely well sir.’

‘I aim to please. And call me John.’

‘Yes sir. John.’

‘No regrets?’

‘No sir. John. No John. It was all I wanted.’

‘And needed?’


‘Good. I must say you have a nice bottom. Actually a lovely bottom. Could have been designed for corporal punishment.’

‘I have often been told that.’


‘Even at school. A chemistry teacher once told me that I had the nicest bottom he had ever caned. I didn’t appreciate it at the time.’

‘How old were you?’


‘Did he take your pants down? Did he do it bare?’

‘No sir. John. No. But I think he would have liked to.’

‘Didn’t we all.’

‘You say we. So you were a real headmaster?’

‘Of course.’

‘And did you?’

‘Did I what?’

‘Take down the pants of your boys. Cane them bare?’

‘No, never. Not done, even in my day. We could still cane, of course. Often did. But I had my fantasies.’

‘Now realised.’


‘You are very good.’

‘As I said, I aim to please.’

‘You did John. Sir. God, how I needed it.’

‘For this relief much thanks.’


‘Very good.’

‘Thank you sir.’

‘Worthy of another twelve before you go.’

‘Yes sir.’

‘Then back to my study boy and pants off. I wish to see that bottom again.’


And he did. And I got another twelve with the redwood before departing. Nothing else. It had been clear from the first session that he was happy to play with a boy’s genitals prior to caning but all else was off limits. That would have to wait until I got home. Spurting my built up tension would be fuelled by imagination and recall. As it should be. Headmasters, even retired ones with unfulfilled fantasies have their rules. I and all on the Great North Road would understand. At least I hope so.


(c) Alfred Roy 2017