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Chapter 1 Judith Concedes
Sir Jolyon Lattimore reached into the inside pocket of his pinstriped Savile Row suit and took out a gold ballpoint pen which he handed to Judith. “What if I choose not to sign?” asked the young woman as she took the pen from him, a note of defiance in her voice.
Sir Jolyon paused for a moment before answering. “Well, whether or not you sign is entirely your decision but should you choose not to sign you will leave me with no alternative other than to fire you on the spot. I must also add that should you choose that route you’ll be lucky to find employment beyond working on a supermarket checkout or stacking shelves in a DIY store, rather a waste for an ambitious young woman with a Master’s Degree from Cambridge I’d say.”
Judith swallowed hard as her eyes hastily reread the agreement which Sir Jolyon had placed in front of her a few minutes earlier. She breathed deeply as she contemplated her options, her thumb nervously clicking the nib of the pen in and out. The position at Lattimore, Harvey and Errington had been the perfect start to her professional career, that is, until she had been foolish enough to be tricked into providing personal information about one of the company’s top clients to a rogue reporter over a dinner date.
Judith’s moments of contemplation seemed like forever, but eventually she gently nodded her head “Okay, I’ll sign.” her voice little more than a whisper. After placing her signature at the bottom of the agreement she handed the pen back to Sir Jolyon. “I think you’ve made a very wise decision Judith.” His deep cultured voice almost providing some comfort to what the young woman had agreed to.
Sir Jolyon Lattimore was a distinctly handsome man and although more than twice Judith’s age she could not deny that she found him extremely attractive. As he picked up the signed agreement and walked across his office to place it in the safe, Judith’s eyes followed him. For a man in his late forties he was in excellent physical shape, his swarthy good looks and dark hair flecked grey at the temples had caught her attention from the first time she had met him, but never in her wildest dreams had she expected to face what was in store for her on this particular Friday evening.
As Sir Jolyon began preparing for Judith’s punishment, she glanced at the antique dial clock which hung on the wall opposite his desk. It was fast approaching 6.00pm, almost a full hour since the working day had officially ended and the other staff had headed home for the weekend. After a few moments of consideration, Judith asked Sir Jolyon if she could contact her friend,” I was due to be meeting a friend in Covent Garden at 7.00 pm, may I go to my office and send a text to let her know I’m working late and won’t be able to make it?”
Sir Jolyon smiled “Yes of course, I suppose in a way that’s exactly what you are doing Judith, working late.” Sir Jolyon smiled and tilted his head in the direction of Judith’s office, she wasted no time in hurrying off to message her friend.
Judith returned a few minutes later and as she entered Sir Jolyon’s office her eyes were immediately drawn to the implements which Sir Jolyon had placed across the red leather inlay of his desk. Judith had little doubt that Sir Jolyon intended to enjoy every moment of punishing her, subjecting her to a level of pain and humiliation which she had been cornered into accepting without redress. Judith smiled inwardly though, as a growing level of excitement invaded her body and had she been given the option of walking away at this very moment, her job intact, she knew that she would somehow be compelled to stay. She did not intend to share this strange desire with Sir Jolyon and would want to make him believe that being punished by him was truly unbearable.
Sir Jolyon stood beside his highly polished pedestal desk and rested a hand on its edge. His eyes appeared to scrutinise every inch of Judith’s perfect body as she stood before him. “Take off your clothes Judith” instructed Sir Jolyon, his voice calm yet powerful, not unlike that of a trained actor.
Judith made no verbal reply and began removing her clothing in a controlled and unhurried manner carefully folding each item as it was removed and placing it neatly on the seat of a nearby chair. Beneath her blouse was a see-through top and as Judith started to remove it Sir Jolyon told her to leave it on. She wore no bra, her pert young breasts were firm and hung well unaided. “Turn around Judith” commanded Sir Jolyon, using the index finger of his right hand to draw an imaginary circle in the air “Let me see your bottom”. Judith turned as instructed and after a couple of moments of visual scrutiny Sir Jolyon stepped forward and ran his hands over the perfect contours of her young buttocks before squeezing them firmly with his large, masculine hands. Judith wriggled, as even this mild attention was not without discomfort and she could only imagine the true pain she would be subjected to when Sir Jolyon began to spank her.
Stepping slightly back Sir Jolyon’s cultured tones again echoed in Judith’s ears “Let me see your arsehole Judith”. Judith couldn’t help but think that the word ‘arsehole’ when spoken by one less cultured had a crudeness to it which could easily repulse, but in Sir Jolyon’s hands the word sounded almost refined. Judith placed her hands on her buttocks and slowly eased them apart. “That’s excellent Judith, just stay like that while I take a good look at your arsehole”.
Judith almost savoured the use of the word for a second time and as she stood with this most private orifice on full display to Sir Jolyon, she somehow curiously imagined that it may be a word which featured more regularly in her own vocabulary from now on. Sir Jolyon placed the tip of his index finger against the neat bud presented to him and pressed against its centre. “Beautifully tight Judith, but I’m sure we can coax it open when we need to.”
Judith enjoyed anal sex, but this too would remain a secret from Sir Jolyon. It was now her turn to use a word which sounded crude in the wrong hands “But Sir Jolyon must I really be buggered?” She knew that he would not change his mind, men like Sir Jolyon rarely do and in truth she probably didn’t want him to. Sir Jolyon chose not to answer the question directly “You’ve read and signed the agreement Judith, so let’s get on with things shall we?” Sir Jolyon pointed toward his desk and as he removed his jacket and rolled up his sleeves Judith took her position bent over it with her hands on the leather inlay and her eyes focused on the implements which were soon to challenge her endurance.
Chapter 2 The Hand and the Plimsoll
Judith had been born far too late to have ever encountered corporal punishment at school but had often been fascinated by the stories she had heard of punishments carried out in years gone by. The boarding school her parents had sent her to was steeped in tradition and as she looked at the black, size 6 plimsoll and the two, different sized crook handled canes in front of her, her mind flashed back to the display cabinet in the entrance hall of her former school which contained an array of similar items which had been used on errant bottoms in decades before, a kind of tribute to the era.
She also recalled a time when she and another girl, Shelley Bailey had stood before the Headmistress’s desk during their final year of school after being caught with two boys in the sports pavilion. “If you’d been at this school a few years ago you’d both be getting your bare bottoms soundly caned for this,” the Headmistress had growled. Judith had never forgotten these words, they always sent a tingle of excitement through her body whenever she recalled them, triggering memories of how much she had wished the Headmistress could have caned her and Shelley on that day.
Both she and Shelley had lost their virginity in the pavilion to those boys, and somehow watching each other getting their bare bottoms caned for this act had become etched in her fantasies. She also imagined the two boys there also, eagerly watching as she and Shelley were caned before thrusting out their own bare bottoms for the cane as she and Shelley were made to watch. Facing away from Sir Jolyon as she was, she allowed herself the opportunity to run her tongue across her top lip as she savoured this delicious thought.
Judith’s time for reminiscence and fantasising was soon over as Sir. Jolyon placed his hand against her left buttock. “I’m going to warm you up with my hand Judith, just to break you in. Are you ready?” Judith inhaled and exhaled a couple of times before answering, “I’m ready Sir.”
Sir Jolyon drew back his hand and brought it down with a resounding smack against Judith’s left cheek. Judith kept her composure but within her the sting which blossomed through her left buttock was enough to let her know that this spanking was for real. With little time for contemplation Sir Jolyon placed a similar smack to her right buttock before beginning a rhythm of alternating rapid smacks from one cheek to the other, a pattern only broken by the occasional slap to the centre of her bottom. As the spanking progressed, Judith’s small, firm young bottom was soon glowing pink.
The spanking hurt, there was no denying that but Judith mostly remained stoic, the occasional wriggle and deep intake of breath the only sign to her discomfort. Sir Jolyon did not count the number of smacks, his purpose was to ‘warm her up’ in preparation for the selected implements and this was best judged by seeing her bottom reach the desired level of redness.
Eventually Sir Jolyon stepped back “How does that feel Judith?” “It stings Sir and my bottom feels really hot,” her voice almost haughty in tone. Sir Jolyon reached forward and picked up the plimsoll from the desktop. Gripping it firmly at the heel end he leaned forward and held it a few inches from Judith’s face and slightly to the side, “Have you ever been punished with one of these Judith?” Keeping her head still, Judith moved her eyes to the side and focused on the plimsoll. “Of course not Sir, they’d banned corporal punishment by the time I went to school, I’m surprised you didn’t realise that.” Sir Jolyon chose not to react, if Judith wished to goad him then it would be her bottom that would pay.
Sir Jolyon turned the plimsoll to hold it by the toe end. “I was going to spank you with the lighter end of the plimsoll, but on reflection I think the heavier, heel end is what you deserve.” “Oh, must you Sir?” responded Judith, her voice more humble than before. “Now bend a little further forward and stick your bottom right out.” Judith slowly did as instructed and as she reached forward her fingertips accidentally pushed one of the canes a little nearer the edge of the desk.
Sir Jolyon had deliberately left the canes where Judith could not avoid seeing them, a reminder that she would soon be feeling their bite across her naked buttocks. As Judith pushed her bottom outwards the slight opening of her cheeks allowed air to pass between them and made her wonder whether Sir Jolyon was getting another view of her arsehole.
”You’re going to get twelve with the plimsoll, or did you call them daps at your school?” “We used to call them pumps Sir Jolyon, I believe you’ll find they have different names in different parts of the country.” “Well Judith you really are a mind of information but regardless of what you call them, the pain they inflict is exactly the same.” Sir Jolyon gently tapped the heel of the plimsoll against Judith’s left buttock before drawing it back and delivering the first blow. The solid thud as plimsoll displaced flesh caused Judith to cry out “AAH! AAH! OW! that really hurts Sir.“ and as she wriggled her bottom to quell the discomfort the plimsoll delivered another fierce whack to her right cheek causing Judith to jolt forward knocking the thinner of the two canes from the desk. “OW-AH-OW, I’m sorry Sir, I’ll pick it up” said Judith apologetically, her voice trembling in discomfort as she spoke.
Sir Jolyon stepped back and watched as Judith went around the desk and bent down to pick up the cane and replace it on the leather inlay, his eyes drawn to the two deep red imprints which the plimsoll had added to her already well-coloured bottom. With no prompting required, Judith repositioned herself with her bottom once again offered for Sir Jolyon’s attention.
The heel end of the plimsoll was hard and unforgiving and as Sir Jolyon applied another whack to her left cheek Judith cried out “AAH! Oh God, that hurts Sir.” It was all that Judith could do to stay in position and as an experienced spanker Sir Jolyon moved in a little closer and placed his left hand against her lower back before adding, “It’s a spanking Judith, it’s meant to hurt”
From this closer position, Sir Jolyon adjusted his aim to bring the plimsoll down more vertically and with his hand firmly restraining her back, he proceeded to add further alternating whacks to her already challenged bottom. Judith wriggled and cried out with each one but resisted any protest. She had underestimated how much the plimsoll would hurt, her only experience to date had been secretly spanking herself in the privacy of her own apartment.
Judith had always liked her own bottom, she had no explanation for this it was just the way she was, and when at home she would often study it in the large mirror which hung on her bedroom wall. Despite the agony of the moment Judith knew that in truth, she wanted to be here.
With one more whack of the plimsoll remaining Sir Jolyon paused for a moment. “Tell me Judith, what’s always special about the last stroke?” Judith hesitated before answering, she instinctively knew what she should say but had no intention of giving Sir Jolyon the satisfaction. “It means that there won’t be any more after it Sir.”
Sir Jolyon chuckled and drew his arm right back before delivering a blistering whack to her already roasting right buttock. “EEEOWCH,OW-OW-OW!…. it’s the….the h-h-hardest Sir.” her voice displaying an almost strangled tone. Sir Jolyon smiled, “You’re a quick learner Judith, I’ll give you that. You may rub yourself.” At this invitation Judith began frantically rubbing her anguished bottom.
The hand spanking had certainly stung but it had been nothing compared to the plimsoll and as her hands traversed the surface of her buttocks she could feel the pattern which had been embossed on them by the hard, rough, rubber sole. Judith’s buttocks stung more than she could have imagined and as her eyes were again drawn to the canes which lay in front of her she could only imagine the pain she still had to endure.
Chapter 3 Time for the Cane
It had been more than six years since Judith had stood shoulder to shoulder with Shelley Bailey in front of the Headmistress’s desk and since that time she had often found herself fantasising about being caned. She knew though, that in truth her interest in corporal punishment had existed well before that time, the display cabinet in the entrance hall of the school had captured her interest from almost the day she had arrived there and she knew that this curious desire was just something that was part of her. Somehow, Judith had never shared this with anyone else. She’d been tempted certainly, and knew that with her looks it wouldn’t be hard to find someone, male or female, who would relish the opportunity to spank and cane her naked buttocks.
After receiving the twelve whacks of the plimsoll Sir Jolyon had escorted Judith back to her own office and made her stand facing the wall. He had decided to allow her a short period of respite, making her stand with her well-spanked naked bottom on display within her own office. Placing his hand on her cheeks as she stood, Sir Jolyon gently stroked them, feeling their warmth as he did so prompting Judith to say “Thank you Sir, that’s very soothing.”
Apart from Sir Jolyon there was no one to see Judith, but he mischievously imagined her, this moment etched on her mind whilst dealing with a handsome male client, perhaps wondering his reaction should he have seen her spanked bare bottom displayed as it now was.
Sir Jolyon returned to his own office and after making a brief telephone call he made a few adjustments in preparation for Judith’s caning before requesting her return. As Judith came through the doorway, she could see that Sir Jolyon had cleared the surface of his desk and placed a plump velvet cushion near the centre. “I’m going to cane you now,” announced Sir Jolyon, his educated velvet tones almost matching the texture of the cushion, ““You’re going to receive twelve strokes Judith, six with each cane. Should you fail to remain still, use any inappropriate language or displease me in any way you will receive extra punishment. Is that clear?” Judith drew her lips together and gently nodded, “Perfectly, Sir.” came her eventual, almost whispered vocal reply.
Sir Jolyon had hung the two canes on the brass doorknob of the heavy oak door which led through to his secretary’s office and as he selected the thinner of the two canes, Judith found herself wondering whether Sir Jolyon had ever punished Sophie, his attractive blonde secretary, in this way, she truly hoped he had. Sophie also had a magnificent bottom, so often perfectly packaged within the tight skirts she favoured.
Bent over the desk, Judith placed the cushion beneath her belly, at Sir Jolyon’s request she gripped the far edge of the desk and widened her stance as he addressed the centre of her bottom with the cane before drawing it back and testing it through the air. Judith flinched as she anticipated the cane striking her buttocks, but was soon to realise this was just a ‘practice stroke’. The unmistakeable swishing sound as the thin, whippy cane displaced air, sent a wave of nervous excitement through every cell of her body as in a way she felt a sense of relief that the caning she had waited for so long was about to become a reality.
Again, Sir Jolyon squared the cane to the centre of her bottom, before saying “This is going to be painful Judith, very painful indeed.” “I’m aware of that Sir and I know I deserve it for the embarrassment I have caused.” replied Judith, making every effort to sound sincere. This time the air was not Sir Jolyon’s target and as the first stoke landed crisply across Judith’s buttocks she tightened her grip on the edge of the desk as a deep intake of breath hissed through her perfect teeth. For Judith, the feel of the cane’s bite was different to how she had imagined.
She had tried caning herself at home, using a cane she had bought to support a tall delphinium which grew in a pot on the balcony of her apartment, but generating an accurate, forceful stroke had not been easy and although she had made her bottom sting, she knew it would in no way match the strokes she must now endure. Sir Jolyon’s intended target was the lower, fleshier part of Judith’s bottom and as he delivered the second stroke parallel to the first Judith flexed and straightened her knees causing her bottom to move up and down “OW, WOW, WOW!” she cried.
With her caning barely underway Judith somehow felt cheated, she had wanted to be caned for so long but now that it was happening for real, she truly hated it, the cane felt so different to her expectations, its hard explosive bite unlike the sting of the broader implements she had been more successful in experimenting with at home. Sir Jolyon raised the cane for a third time before delivering another crisp stroke. “OUCH!…. OUCH!… AAH!” yelped Judith as she contorted her upper body at her discomfort before adding “It really hurts Sir, my bottom really hurts.” “It’s supposed to hurt,” replied Sir Jolyon gruffly, as he again addressed the target area with the cane, tapping it alongside the slender red stripes which had already emerged on the pinnacle of both of Judith’s buttocks.
The next two strokes added further to her discomfort but as many who have been on the receiving end of a caning will attest, as the caning progresses it becomes more bearable and with just one more stroke of the thin cane remaining Judith was beginning to acclimatise and despite the pain, or perhaps because of it, she began to feel aroused by her ordeal. Once more, Sir Jolyon drew back the cane, this time a little further than before. As the final stroke of the six this would be the hardest and aware of this fact Judith braced herself accordingly. As the cane began its descent Sir Jolyon employed greater wrist action and speed, driving it close to the point where buttock and thigh merge. “YEEOW, AAH! AAH! OW, WOW!” squealed Judith as the bite of the cane exploded in her bottom.
Desperate to clutch her wounds but aware that she must be given permission, Judith hovered her hands behind her before Sir Jolyon gave her that permission, “If you wish to you may rub yourself.” he said, his voice showing little sympathy for her plight. Judith wasted no time in clutching her cheeks and as her hands traversed them in an attempt to ease her discomfort, Sir Jolyon replaced the cane on the doorknob, exchanging it with the heavier, thicker cane. Judith watched his every move. Judith’s bottom was sore, she could not deny that but within her blossomed a height of arousal she had never before experienced. She momentarily recalled an article she had read in a spanking magazine about a young woman who despite finding the pain of a caning almost unbearable claimed to prefer being caned to having sex.
The shock of the first few cane strokes she had received seemed now almost a distant memory and with both mind and body in harmony Judith was ready for the rest of her punishment. “Bend over again Judith,” requested Sir Jolyon, holding out the cane as a kind of pointer to where she should place her hands. The sound of those simple words, ‘bend over’ sent a quiver through her body and Judith felt compelled to run her fingertips along the end of the outstretched cane, as if sensuously acquainting herself with what her bottom was about to experience. “Six with the senior cane should help keep you on the straight and narrow.” added Sir Jolyon.
Sir Jolyon’s experience was enough to make him sense that despite the anguish Judith had displayed to her punishment to this point, she was beginning to be absorbed into the true submissive role. Any temptation to suggest to her that she was enjoying her ordeal would though have to wait, but Sir Jolyon’s instincts told him that it may not be much longer before she fully convinced him of this fact.
Sir Jolyon’s eyes focused on Judith’s magnificent bottom. The slender stripes left by the thin cane made a perfect template for the application of the senior cane. If the thin cane had challenged Judith, she was now about to experience a proper ‘six of the best’. “Are you ready Judith?” asked Sir Jolyon. “I’m ready Sir, she replied timidly.
As Sir Jolyon once more offered the cane to Judith’s buttocks, gently guiding it over their perfect contours, he questioned in his mind whether Judith’s bottom was indeed even more delightful than that of Sophie, his secretary. His mind travelled back to the first time he had caned Sophie, her screams each time the cane had struck her luscious bottom had been almost enough to raise the roof of his office, but now after a whole year of regular spankings and canings Sophie could accept her punishment without undue fuss.
Sir Jolyon’s mind quickly refocused on the bottom now displayed in front of him. Drawing the cane back, he wasted little time in delivering the first of the six strokes. The more rigid nature of the senior cane caused the firm young flesh of Judith’s bottom to ripple on impact and for her to arch her back in an effort to quell the agony of the stroke. “EE-OW!” she shrieked, but almost before the echo of her voice had faded from the room Sir Jolyon applied the second stroke. The white stripe it painted on the delicious canvas of her bottom soon flushed deep red as Judith’s grip on the edge of the desk tightened, showing near white knuckles as she contorted her bottom wildly. “OUCH! OUCH! ..OUCH!.. OH MY BUM! she cried.
Raising the senior cane for a third time, Sir Jolyon delivered another hard stroke, this time his target area the upper portion of Judith’s buttocks “OW..OW..OW” squealed Judith, and as the forth stroke landed close to the third, her response was less than ladylike, “OW-OW-OW, OH FUCKING SHIT!” she yelled. Sir Jolyon made no response to Judith’s outburst other than a private smile, and allowed her a moment to regain her composure before offering the cane a little lower on her bottom. The fifth stroke was a fairly routine one, hard but not excessive and apart from a low gurgling sound Judith showed little distress. Sir Jolyon’s experience though, had taught him that delivering a penultimate stroke that erred on the milder side was a ‘false security’ for the punishee and made the traditionally harder final stroke all the more effective.
“Remind me Judith, what’s special about the final stroke of the six?” enquired Sir Jolyon as he repeatedly tapped the cane across the centre of her bottom, his rich tones presenting an almost menacing air as he spoke. “It’s the hardest Sir.” replied Judith trying to avoid flinching as the tapping of the cane against her sore bottom was in itself enough to impart an uncomfortable sting. Judith screwed up her face as she awaited Sir Jolyon to pull the trigger. Somehow though she wanted this stroke to be severe, to test her every fibre, had she been asked she could never have explained this to anyone, it was just part of her curious desire. Judith didn’t have to wait long and as the sixth stroke with the senior cane was unleashed against her bottom it was as though a red hot poker had been placed across her behind. “OH SH-SH-SHIT, BLOODYHELL…..OW-AH-OW,” screamed Judith as she reached back and clutched her bottom without permission.
Sir Jolyon paused and secretly enjoyed the ‘floor show’ as Judith struggled to regain her composure. He allowed himself a smile at the sight of her glistening labia which from her bent over position, peeped erotically between her sumptuous, spread thighs. If there had been any doubt about this young woman’s inner desire to be caned, it was now completely erased. “This is no more than you deserve Judith.” Sir Jolyon added, resisting comment about the moist lips of her cunt. “I understand that Sir,” replied Judith, uncomfortably aware of her wetness. Sir Jolyon reached forward and ran his hand over the raised weals which now adorned Judith’s buttocks before offering a finger to the tell-tale juice which oozed from within her. Judith remained silent, the embarrassment of her arousal making the cheeks of her face a near match to the redness of the cheeks of her throbbing behind.
Bringing his hand back, Sir Jolyon savoured the aroma before secretly sucking the nectar from his finger. “Six more strokes Judith, for using bad language, failing to wait for permission to rub yourself and apparently enjoying your punishment just a little more than you were supposed to,” he announced, “you’re going to receive these as a straight six, one after the other without a gap.” Judith stood upright and turned to Sir Jolyon, “Oh but please Sir, I don’t think I can take any more, please just bugger me now” she pleaded, her voice sounding genuinely distressed. “You’ve got thirty seconds to present yourself back over the desk or I’ll make it a straight twelve,” growled Sir Jolyon. Judith wasted little time in returning to position, she had once seen a girl in a video clip get a ‘straight’ caning and knew that it would take every ounce of her self-control to endure six strokes, twelve was just unthinkable.
“Are you ready Judith?” Sir Jolyon’s deep, authoritative tone appeared more of a command than a question. “I’m ready Sir,” replied Judith. Sir Jolyon paused for a moment to visually savour the delight of the magnificent bottom which nature had given to Judith, the creamy, smooth appearance of her perfect buttocks which had been revealed to him as she had slipped off her panties earlier that evening, had now been replaced with a vividly colourful and rugged landscape. For Judith the few seconds of visual scrutiny Sir Jolyon afforded himself seemed like forever as the nervous anticipation of the remaining cane strokes grew within her. Sir Jolyon reached forward and ran his index finger across the lower part of Judith’s bottom “I’m going to cane you in line with the position of your arsehole Judith, it might just help to rouse it before I bugger you.” Inwardly Judith once more relished Sir Jolyon’s reference to her ‘arsehole’ and his use of the word ‘bugger’ had a richness to it which seemed so much more preferable to terms like ‘take you up the bum’ or ‘fuck you in the arse’.
Judith swallowed hard as Sir Jolyon offered the cane to the target area. As she felt the cane drawn away from her she pressed her upper body hard against the desktop as almost simultaneously the cane returned with a ferocity she could never have imagined. The sound of the impact as the cane bit deep into her flesh resembled a pistol shot as it echoed around the room. As ‘THWACK’ followed ‘THWACK’, Judith barely had time to distinguish one stroke from the next as she writhed and contorted, with little time to cry out before the caning was over. “YEEEOW….Mmmmmm…. OWAH… AHA….OW!” she shreiked as the cane came to rest.
With the six strokes skilfully placed close to each other, the lower portion of Judith’s bottom felt like it was on fire. “OH IT BURNS!….IT REALLY BURNS, SIR!” she whined as Sir Jolyon gave her permission to rub herself. Judith clutched her bottom and began frantically rubbing her wounds, the feel of the raised weals through her fingertips resembled a ploughed field and she immediately wondered whether the marks of her punishment would be gone before her holiday to Florida in a fortnight’s time.
Thoughts as to whether she would be able to wear the new bikini she had purchased for her holiday flashed through her mind, it’s skimpy design did little to protect the modesty of her bottom and any marks which remained would be clearly on view. “You may stand and turn around,” announced Sir Jolyon, “you can have a few moments to recover before the final part of your punishment. Slowly, Judith responded to Sir Jolyon’s words, even more uncomfortably aware of the wetness between her legs as she presented herself to him. As often happens with a caning, the pain it inflicts is quick to subside and as Judith continued to rub herself, the feeling in her bottom was soon to transform into a hot, pleasurable glow.
“Well done Judith, you did very well indeed,” announced Sir Jolyon as she watched him place both canes into a well-worn leather sports bag similar to the one she remembered her father using when he had played cricket many years ago. Sensing her interest in the bag Sir Jolyon, informed her that both he and his father had used it during their cricketing days at Oxford, but now that he no longer played cricket it made a useful container for his spanking equipment. As he spoke he produced a sturdy looking birch which he held up in front of Judith whilst reaching down with his free hand and offering a finger to her wet minge. “I could use this birch on you now Judith, as it seems you really have enjoyed your punishment just a little too much, but I’ll spare you this time.” Once more Judith blushed, unable to find any words which could reduce her embarrassment. “I think though, we may have to use the birch the next time I need to punish you,” added Sir Jolyon. Judith gulped hard, “You’re going to punish me again?” Sir Jolyon smiled before responding, “I think we just might need regular sessions seeing as how much you seem to have enjoyed this one.”
Chapter 4 Buggered before Dinner
Once more Judith found herself bent over Sir Jolyon’s desk with her bottom presented to him. She was now completely naked, Sir Jolyon had ordered her to remove the see-through top she had worn during her spanking and caning and with the spanking implements safely tucked away in Sir Jolyon’s leather bag, Judith was now at his mercy for the final part of her punishment. Her bottom stung like it had never stung before, but as Sir Jolyon stood behind her and grasped her buttocks with his hands she could not deny that the aftermath of such punishment was not altogether unpleasant.
“I’ve booked a table for us at a little Italian place I know in Covent Garden so that you won’t completely miss your night out Judith. It’s rather a basic little restaurant with plastic table cloths, tacky cruets, and although the wooden chairs they have may be a tad uncomfortable for someone with a well-punished bottom, the service is marvellous and the food is just exquisite,” announced Sir Jolyon as he began to knead the flesh of her buttocks. “Th..th..at’s very, OOH! thoughtful of you Sir J.J..Jolyon,” replied Judith, her voice wavering as she began to writhe to his touch. The attention he was giving her hurt, there was no denying that, her buttocks were covered with raised swellings and although these swellings had soon lost their bite as the caning had ended, squeezing and manipulating them was quick to reignite some of their fire, but it was like that curious feeling that can be got from pressing a bruise and not being sure whether the sensation it creates is pleasure or pain. Judith could only imagine the discomfort she would have to endure whilst sitting on a wooden chair at the restaurant. She was again made to think of the display cabinet at her school where genuine handwritten punishment records contained in the cabinet made a number of references to pupils who had needed to ‘stand for the remainder of the lesson following a caning as it was too uncomfortable to sit’. One particular entry which had become fixed in Judith’s mind stated that ‘Following receipt of twelve strokes of the senior cane applied to the naked buttocks at 9.15am for talking during assembly, Miss. Elaine Hamilton-Davis was provided with two pillows from her dormitory bed to enable her to sit more comfortably whilst completing her Ordinary Level English examination.’ Judith had no idea who Elaine Hamilton-Davis was but had frequently found herself drawn to the display cabinet just to reread that entry.
Sir Jolyon continued to tease Judith’s flesh for a while before offering a finger to her anus. It was a finger he had lubricated from her own juices, a finger he had run in between her cunt lips collecting more of her delicious nectar. As he eased his finger into her hole Judith gave out a sigh, she had always hated that first intrusion, it always made her squirm, but her ex-boyfriend had visited this most private orifice many times and she knew that beyond the initial discomfort, pleasure would almost certainly follow.
Sir Jolyon’s hands were large and strong, the hand spanking she had received from him had certainly challenged her and now that his sturdy index finger explored her inner realms Judith began to breath heavily. As Sir Jolyon began to work her open, he offered a second finger to her anus, coaxing it even wider. Judith could no longer contain herself at the attention her attractive boss was giving her and with her hands clutching the far edge of the desk she began to sway back and forth enabling her pert nipples to rub against the leather surface, igniting an arousal she could no longer contain.
“Oh, bugger me now Sir Jolyon, please bugger me now.” The words had slipped from Judith’s lips against her intentions, it was one of those dreadful and embarrassing moments where thoughts turn into words without control. Sir Jolyon though, needed no such invitation, his large, erect cock stood proudly before him and with his pinstriped trousers settled below his knees he was more than ready to offer himself to her beckoning hole. As Sir Jolyon began to slide inside her, Judith felt the challenge of his girth to her anal sphincter, she had always been able to accommodate her ex-boyfriend with ease, but as Sir Jolyon’s hardened member journeyed to its limit in her arsehole, Judith knew that she was about to experience being buggered by a real man.
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