The Winning Stroke – A Caning Story from Janus

A Caning Story from Janus 124. More stories are available here.

The Winning Stroke -
by Paul Melrose (Alex Birch)

Thwaaaack! The small black rubber ball struck a spot on the wall just above the ‘tin’ and dropped into the corner with hardly a bounce, foiling the desperate attempts of the young pony tailed blonde girl, who had changed direction in mid stride, to reach it. She skidded into the corner of the squash court, almost colliding with the wall in her failed attempt to play the ball before it bounced a second time, and squealed in frustration as the small missile avoided her desperately extended racket. As she did so her dark haired opponent who had played the winning shot jumped into the air with racket aloft, a winner’s smile etched across her pretty face.

“9-3, 9-7..” she shouted in exultation, “..wow, Claire, that’s the first time I’ve ever beaten you!” then ran over to where the young blonde was getting her breath back and put her arm around the smaller girl’s shoulders. Claire Francis forced a grin and kissed her friend on the cheek.

“Well played, Sarah!” she said ruefully, “My coaching must be doing you good. That’s the fittest I’ve ever seen you over a whole match. I’ll just have to play on two legs next time!”

Sarah Cole grinned, playfully smacking her friend on the rump with her racket as the two girls left the court arm in arm and went straight up to the club bar without bothering to shower and change. Sarah was the elder of the two by three months at nearly nineteen, the girls having formed a close friendship ever since the third year at Comprehensive School and now they shared a flat.

In appearance they were as different as chalk and cheese, Sarah dark skinned, beautiful and serious natured, with a tall willowy frame and long, shapely legs, while Claire was a radiantly pretty ash-blonde with freckles and a permanent happy smile, slightly more rounded in shape than her friend though without a hint of fat, her firm, full breasts and shapely plump bottom frequently drawing wolf-whistles from the workmen on the building site opposite the flat. Claire would just grin and waggle her bum to provoke even louder comments for such was her nature, often reducing Sarah to hapless embarrassment by her behaviour. Yet they were a perfect contrast to each other as flatmates, each contrasting personality providing a catalyst for the other.

“Loser pays,” Claire volunteered generously, “usual is it?”, and strolled up to the bar as her friend nodded in accord. When Claire returned with the iced cokes, Sarah was ploughing through the jobs page of the local paper.

“C’mon, Sarah,” Claire begged in exasperation, “I thought we were having fun today not looking for work,” but the tall brunette shook her head impatiently.

“We’ve got to find something,” she said anxiously,” because the rent’s due soon and we haven’t a cent between us since I got made redundant. I know you enjoy coaching the kids here but it doesn’t bring much in. We’ve both got to get work soon. Hey, look at this!”

Claire looked over her friend’s shoulder and read, ‘Young women wanted for challenging and exciting work. Should be between 18 and 30 and in good physical condition. Phone David Chalmers of Galway Securities’ then a London telephone number.

“Nothing ventured,” Sarah said with some excitement, “it might be nothing except delivering Yellow Pages but we might as well find out. We’re perfectly qualified in the fitness department and it might be fun.”

oOo

Two days later, Claire and Sarah sat in a shabby office above an estate agents in Holloway Road answering a string of questions from a dark suited good-looking man in his mid forties who had shaken hands with both of them on arrival, his warm smile disarming them both.

“So, girls, you want a bit of adventure in your lives?” David Chalmers enquired, his eyes looking them both up and down with obvious approval. “Well, you’ve come to the right place but I must impress upon you that the work is highly confidential and will require you to sign a legally binding vow of secrecy if I take you on. You know what that means, don’t you! You must not discuss anything connected with your work with anyone… anyone at all… or you will be taken to court for breach of contract! Are you happy about that?”

Both girls nodded enthusiastically and Sarah ventured, “Mr. Chalmers, what does this work entail? Is it dangerous or are we asked to break the law?”

Chalmers hesitated for a moment, then shook his head and smiled.

“No there’s no James Bond stuff,” the two girls grinned, “but we do deal with divorce cases and getting evidence of adultery which can be messy, plus a bit of industrial espionage work from time to time. That’s why I use women in this role because they attract less suspicion. It does require a clear head and a bit of nerve because if you get caught doing any commercial spying, I will not admit to employing you for obvious reasons. We may have to get you into places using phony credentials but I promise you no breaking in is involved, only perhaps the copying of some documents and sometimes taking some revealing photographs. Can you accept that?”

The two girls looked at each other, faces glowing with excitement, and Claire replied, “I think you can rely on us, Mr. Chalmers!”

Chalmers smiled happily and took some forms from the drawer of his desk.

“You both look very fit and healthy if I may say so,” he said admiringly, “Do you work out?”

Sarah blushed at the compliment and replied, “We both play at the Beaufort Squash Club. Claire coaches the juniors there, you know!” glancing proudly at her friend.

“Excellent,” Chalmers beamed happily and pushed the forms across the desk. “Then welcome aboard subject to your signing the secrecy agreement and a check that you have no criminal convictions of course. We pay only on results and the rate you get depends on who is ordering the work. Understood?”

The girls looked at each other hesitantly. Not as good as a guaranteed salary but better than nothing in their current predicament, so they both nodded their assent. Chalmers told them he would make contact in three days once their personal vetting was complete and the two girls left the office on cloud nine, for suddenly their dull and boring existence had opened up new and exciting possibilities… and a chance to pay the rent.

As promised, a telephone call three days later led Sarah and Claire back to the Holloway Road office where, after pouring a drink for them, Chalmers welcomed them formally to Galway Securities before slightly lowering his voice for effect.

“Now, as it happens, I’ve got the perfect job for you two to start and prove your worth. A company called Molecular Plastics based in Finsbury Park makes stuff for the Ministry of Defence, among others. Our friends in high places think they are also selling stuff to Iran, possibly plastic explosives, and that’s strictly no-go. We need to get into the Managing Director’s private office, get into his filing cabinets and look for evidence of any suspicious correspondence which bears out this suspicion. Now then – they’ve got an Open Day reception for potential industry buyers on Thursday and my sources tell me they need a lot of agency hostesses to serve drinks etc etc. Who better than us to supply two of them? We’ve got you in there with forged CVs and a couple of genuine looking ID cards from ‘Executive PR’”

He grinned as the two girls’ mouths dropped open.

“Impressed, eh? Now there will be thirty or so girls there serving drinks, so they won’t miss you two if you creep away once the presentation starts. If someone sees you, just say you are going to the ‘Ladies’… it’s on the same floor as the MD’s office.”

Chalmers produced a floor plan at this point and clarified locations. He reached into his pocket and produced a key which he flourished in front of Claire and Sarah.

“Then, when the coast is clear and you’re certain there is no security about, use this key which we.. er.. borrowed from an over amorous security guard at some cost to the virtue of one of our young ladies, to get into the office and find the filing cabinet. We believe they are dealing with a company called Riza Trading as middle men for this operation. If you find any files that look relevant, use the photocopier on the MD’s side table and return the originals to the files.”

He grinned as the girls looked slightly nervous for the first time, Sarah blushing slightly as she guessed what the young woman had been required to do.

“What will we be wearing for this shindig?” Claire demanded with a worried frown and Chalmers chuckled once more.

“The company is providing a sort of basque for the drinks girls. You might look a bit like a Playboy bunny but nothing worse. Well? Are you game?”

Claire and Sarah stared at each other nervously before both nodding their heads firmly in affirmation as Chalmers grinned broadly and shook their hands on the contract. A new horizon had opened up for them both.

oOo

By Thursday, Claire and Sarah were alternately excited and nervous as their debuts in the espionage business drew nigh. They’d had a call from Chalmers telling them to arrive an hour before the reception commenced at noon, where they could change into their outfits and then be given thirty minutes instruction on how they were to carry out their hostessing duties. By the time they arrived, had been shown the cloakroom and met some of the other girls their nervous tension had begun to ease, both now excited by the thought of the work ahead.

There were some twenty girls in a small cloakroom designed for no more than ten, but fifteen minutes and a confused pile of dresses and underwear later, they were attired in rather gaudy basques, so tight that no underwear could possibly be worn beneath. The cups were cut so low that most of the cleavage was exposed and the groin cut so high that most of the girls bottom cheeks were on display, just a small strip of material protecting modesty, front and back. When the girls stood upright, the tightness round the crotch was only too evident, Sarah and a few other taller girls wincing audibly as the material tightened around the pubic bone.

After a brief introduction to the Company’s marketing staff who explained how they had to circulate, ensuring a smooth and continual flow between bar and reception lounge to keep the free drinks tray topped up, Sarah and Claire were ready for work.

Visitors began to arrive at about 11.45 and by 12.15 both girls felt like old pros’ at the game, so smooth had the routine become. After a few initial cries of indignation they had even become adept at avoiding the odd hand which ‘accidentally’ groped their bottoms as they circulated so, by 1.30 when the technical presentations began, the girls could briefly relax in the kitchen with a drink of their own.

At 2pm, Sarah and Claire slipped out of the bar area and made their way upstairs, meeting only one security man on the way, to whom they smiled politely and walked on slowly, with pounding hearts, back to the cloakroom. After checking there was no one else around, the two girls took the key from their bag, removed their awkward high-heeled shoes and tiptoed out onto the corridor and towards the Managing Director’s office. Gulping with fear and excitement, Claire unlocked the door quietly and both girls walked in, careful to lock the door behind them.

The office was large and well furnished, with a large desk near the window and a couple of black leather armchairs resting on an expensive carpet in the middle of the floor. Two filing cabinets, still with the small keys in the locks, stood by the side wall and the two girls grinned with delight. This would be easy!

They took one cabinet each and began to open each drawer in turn, looking for Riza Trading and anything to do with exports to Iran, until Sarah whispered, excitedly, “I think I’ve found something!” then removed a number of folders and placed them on the adjacent desk. The girls began to scan the correspondence and, as Claire rifled through the papers, so Sarah would photo-copy anything promising. After ten minutes the girls had become so engrossed in their work that neither heard the creak of a door but suddenly jumped out of their skins when a deep and angry male voice shouted, “What the hell do you think you’re doing?”

Claire and Sarah whirled round in astonishment to see a well dressed middle-aged man framed in a doorway which had appeared to be part of the wall, so subtly did the door colouring blend into the wood panelling. He walked forward briskly and stood in front of them, arms folded and eyes blazing with anger.

“Well? I’m waiting!” he thundered and the two girls shrank back in fright. Claire felt excited, despite their predicament, for he was good looking in a mature sort of way and very dominant. A strange thrill coursed through her loins.

“We were.. we were just…” she began bravely then gave up any attempt to lie and took a deep breath. “We were photocopying your confidential papers. There – now you know. We can’t deny that we’ve been caught red-handed! Look..” she pleaded, “..we’d just started. Please let us go. There’s no harm done.”

The man grinned and shook his head in disbelief, then looked them up and down very closely, causing Sarah to blush deeply.

“You don’t seem exactly dressed for espionage,” he observed tartly, “or is that your idea of a disguise? It doesn’t cover much does it! Anyway, no harm done be damned! You think you can just walk out of here after this, young ladies? Well you can think again! One push on this..” and he rested a finger on a button on his desk, “..and the police will be here within three minutes and you two will be well on your way to a jail sentence. You must be mad to think I’d just let you go!”

Claire’s heart was racing madly but she tried to look brave despite the sound of Sarah’s sobbing behind her.

“Who put you up to this?” the man demanded, “Come on I want names or I call the police!”

“Nobody,” Claire replied quickly, “We were just after a fast buck and we thought you might have something the papers might buy. Look, my friend’s very frightened, please let us go.”

The man shook his head. “Not a chance, but wait a minute… you, blondie, I know you from somewhere don’t I? Yes the Beaufort Squash Club, that’s it! You’re the Juniors coach there! My nipper has had lessons from you! Claire Francis that’s who you are! Now..” he looked hard at the weeping Sarah, “you – crybaby – I know your pal’s name so who are you?”

The jibe struck home and Sarah choked on her tears. “Sarah.. Sarah Cole,” she muttered woefully, “Oh this is all a big mistake, please let us go!”

The man ignored her plea and looked them up and down once more. “Well, now we’re acquainted, I’m Kenneth Grant and I’m the MD of this Company. What a good job I chose to come up here and open the safe in my secretary’s office or you two would have got away scot-free. I don’t really believe your story and I think you are working for someone but I can’t prove it. You two are rank amateurs, that’s obvious, but I ought to prosecute you, with all the attendant publicity, and I will – unless you do exactly as you’re told!”

The white faces of the two girls told all as they waited for clarification.

Grant walked around them and looked them up and down once more.

“Very nice,” he said with grim smugness, “you’re both beautifully built. Must be all that squash. Now let’s see how fit you are. I want you running on the spot, knees up as high as you can until I say stop!”

“Now look here…” Sarah began, her voice angry and indignant, but Claire held her arm and whispered, “Just do it.”

Both girls began to run on the spot but Sarah howled in agony from the first as the extreme movement caused the tight restraint around her crotch to bite into her intimate cleft.

“Oh Christ!” she cried out, stopping dead, “I can’t do it in this outfit, it’s cutting me in two!”

Grant nodded his head sympathetically. “How inconsiderate of me to expect you ladies to perform in those costumes –,” both girls breathing sighs of relief which soon turned to gasps of horror, “– so you better take them off!”

Both girls blushed crimson and Sarah cried, “Now look, we’re naked under these – and if you think…” but once more her pragmatic friend whispered, “He’s got us over a barrel, Sarah, it’s that or the police,” then began to reach behind and unzip her costume. Sarah, tears forming once more, reluctantly followed suit and within seconds both girls were stark naked in front of him. At first they tried to shield their breasts and sex with their hands but Grant was having none of that.

“Hands on your heads and start running on the spot again, knees up as high as you can!” he ordered and watched with glee as the two girls sullenly obeyed his demeaning orders. The little blonde who coached squash proved to be a real exhibitionist, fixing him with a cool unabashed gaze as she paraded bouncing boobs and occasional glimpses of pink cleft beneath the cluster of pubic hair while exercising her naked body, but the tall brunette, slightly the prettier of the two, he thought, was obviously deeply humiliated as her firm breasts, glistening with sweat now, bobbed up and down in front of his eyes. She tried to keep her thighs tightly together as her knees rose up and down, desperate to prevent him getting a good look at her intimate parts. Her hapless embarrassment turned him on, particularly as her pathetic efforts were doomed to fail.

“OK, that’s enough,” Grant said sharply and both girls came gratefully to a halt, Sarah prevented from putting her hands back between her legs only by a sharp warning.

“Now I want you both to lie on your backs on the carpet, legs towards me!”

“So this is the pay-off,” Claire said angrily, “This is where you screw us and then let us go!”

Grant snorted sardonically. “I’m afraid you overestimate your charms, my dear. No, I want you to lift your legs high in the air, bring your knees back to your stomachs and cycle in the air for five minutes.”

Sarah let out a gasp, her face crimson. “Th-that’s disgusting..” she cried, “..you’ll see our.. our..”

“..little holes?” Grant said smoothly, “indeed I will.. both front and rear.. and it will be interesting to compare them. Now get on with it or I call the police!”

Sarah was weeping softly as both girls lay on the carpet as instructed and began to perform the humiliating exercise. Again, Grant noticed that the little ash-blonde had no compunction about raising her bottom and pedalling for all she was worth, showing him the most delightful sights on the way, while it took the brunette some seconds to follow suit and then she was reluctant to bring her knees right back.

There was only one remedy for disobedience and, moving forward swiftly as Sarah’s legs rose, he lifted them right up with one strong hand and pushed her knees right back to expose her bottom and sex in all their glory then, with his other hand, he smacked her hard across both exposed bottom cheeks.

The sharp smack was enough, the weeping Sarah offering no further resistance and, once the time was up, both girls were lying back on the carpet, breathing hard, their firm bodies coated in a moist pink sheen.

“Right you can get up!” Grant ordered sharply and the two girls struggled to their feet, faces bright red with exertion and embarrassment.

“Is that it?” Sarah demanded angrily, “Have you seen enough now, you dirty swine? Can we go now?”

To her horror, Grant shook his head and grinned. “Did you think those exercises were simply my voyeuristic fetishes?” he asked. “Oh no, they were much more than that. They were a prelude to your punishment. Your body temperature is raised and your circulation is increased. You should be grateful. It’s much easier to take a caning on a warm bottom than on a cold one!”

Claire’s mouth opened and closed like a goldfish and Sarah, red-faced, her modesty forgotten, just stood wringing her hands in a state of shock.

“You.. you’re going to cane us?” Sarah cried weakly, the tears now filling her eyes, “OH my God, no!”

“Oh my God, yes,” Grant answered, “and I want you over the back of that armchair, leaning over as far as you can, legs apart and bottoms stuck right out. You’re getting eight strokes each across your bare bottoms and then you can go home. Consider yourselves lucky! No police, no courts, no prison record. Not a hard choice is it! Now who’s going first?”

The two girls were in turmoil but they knew he was right. They had no choice.

“Go on, Sarah,” Claire said softly to her stricken friend, “Go first and get it over with,” then squeezed her friend’s hand affectionately as Sarah, almost dazed, allowed Grant to lead her across to the armchair.

He looked at the tall naked brunette stumbling along beside him and then at the armchair, deciding she was too tall to get her hips over the back and her head right down, so he removed the seat cushions. He turned and faced her again, Sarah’s eyes now wide with fright.

“Get over the back of the chair,” he ordered, “right over in a jack-knife until your head touches the seat.”

Sarah obeyed instantly, her head and upper body hung right over the chair as she gripped the edge of the seat, her shapely bottom at the highest point of the arc, her long legs trailing down the back as she stood on tip toe, legs wide apart.

Two people experienced a heady excitement at that moment, neither being the unfortunate Sarah, as Grant raised the whippy rattan for the first stroke. Claire had moved around for a better view and realised, to her shame, that Sarah’s vulnerability and lewdly revealing posture was exciting her considerably. She had never witnessed a caning and when the rattan smacked across Sarah’s bare bottom, the howl of pain and the ensuing bright red stripe across the pale cheeks made Claire tremble. She watched, entranced, as the cane sliced across the quivering naked arse six more times, Sarah’s shrieks and the writhing of her shapely hips as her bottom reddened rapidly prompting Claire to shudder with delight, her sexual arousal sudden and embarrassing.

For the last stroke, Grant brought his arm right back and delivered a hard, sharp stroke to the join of bottom and thigh, the scream of pain and the delightful writhing surpassing all that had gone before as Sarah nearly fell over the chair.


Grant helped her to rise and Sarah stumbled back to where her friend stood waiting her turn, the punished girl weeping bitterly and unable to keep still, her hands constantly rubbing her scarlet wealed backside as she hopped up and down.

Claire took her place, her heart pounding with fear and arousal, but she was too short to hang over the back of the chair so Grant replaced the two seat cushions, borrowed two more from the other chair, then summoned her round to the front. Claire half knelt on the raised seat and half on the chair arm, then hung forward over the back of the chair, her knees wide apart and her bottom sticking right out, her moist gaping sex only too visible to her delighted tormentor.

“Ah, so your friend’s punishment turned you on, eh?” Grant chuckled as Claire’s face burned crimson and she waited with drawn breath. She heard the hiss of the cane and then a red hot poker suddenly burned a track across her bottom. She was determined not to cry out but hung onto the chair with white knuckles, her face screwed up in agony. The second stroke bit lower and she felt the intolerable pain almost lift her out of the seat but she hung on as her bottom became an inferno. She heard Sarah sobbing and Grant hissing through his teeth before the next stroke landed in the crease of her thigh, then Claire gave up all hope of keeping quiet, a strangled squeal emanating from her throat as her plump bottom quivered delightfully, three vivid stripes now decorating her rear cheeks. The next three strokes were spaced evenly across her shuddering flesh, her bottom now a roasting mass of scarlet.

Claire was in obvious pain yet the evidence of clear sexual arousal under the cane’s ministrations was unambiguous and Grant grinned as he completed her punishment with two fierce stroked across the plum centre of her quivering arse before throwing down the cane and ordering her to get up.

Claire somehow staggered off the armchair, no attempt to hide the salty tears now as she put her arm around the anguished Sarah and both girls rocked from side to side in a pain filled ballet.

“You can leave those costumes here,” Grant told them sharply,” and go to the cloakroom as you are. I’ll give you exactly five minutes to get dressed and get out of here so don’t even think about bathing your bottoms! If you’re a second longer I’ll come in after you and you’ll get another dose!”

Two tear stained and pain racked naked girls needed no second bidding but ran hand in hand down the corridor to the safety of the cloakroom as Grant’s laughter followed them down the hallway, both girls oblivious to the two small video cameras which still whirred away in his office.

oOo

Later that night, six men sat sipping whiskies and soda in an elegant Kensington apartment while keenly watching a TV screen. “Wonderful quality,” David Chalmers said with enthusiasm, “go on, run it again from where they take their costumes off.”

With a smile, Kenneth Grant got up from the sofa and dutifully rewound the video as requested. He looked at his companions and shook his head in amusement.

“How long do you think we can work this scam, Dave?” he grinned, “these are the third lot of girls we’ve had on this con!”

Chalmers smiled. “I reckon we can push it for a bit longer provided we keep the videos secret. Just a bit of private fun for us, particularly as you can all hide behind respectable businesses and we rotate locations. The girls don’t connect us and they’re not going to talk and explain how they failed are they! They’re too ashamed to explain why they agreed to bare arse canings either to the cops or ‘Galway Securities’. I just get a phone call every time saying the work didn’t suit them. You can cover almost anything up with a contract of secrecy… except neatly striped arses of course!” as the group clinked their glasses merrily and roared with laughter.

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