Lady Caylethorpe s Caning
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Michelle’s First Caning free porn video
I wasn’t entirely confident that Michelle would show up. As I glanced at the clock in the hallway it was now 6.05pm and I’d arranged for her to arrive at 6.00pm.
I guess the ‘stickler for time’ in me had got the better of my imagination so I wandered into the kitchen and switched on the kettle to make a coffee. As I did so it crossed my mind that despite her husband’s earlier assurances, maybe he’d changed his mind and didn’t want Michelle punished after all.
As the water in the kettle began to warm up, the hissing sound it made broke the silence of the house. I stood and watched the kettle, remembering the words of my grandmother from when I was very small “a watched kettle never boils,” she had often said and although I knew this was just an old saying and not entirely true, I knew exactly what she meant.
The kettle did of course boil, but it did seem to take an age and as it clicked off I again glanced at the clock, it was now 6.10 pm and I was convinced that either Michelle’s husband Simon, had changed his mind about me punishing her, or Michelle herself had decided to avoid the punishment which had been requested for her.
As I stirred the milk into my coffee, the chime of the doorbell rang in my ears and I hurriedly went to answer the door, desperately hoping it wasn’t someone trying to convert me to religion or sell me magic dusters.
Through the small glass panel in the door I was relieved to see that it was Michelle and as I let her in she apologised profusely for her lateness. “I’m so sorry Tobias, I tried everything to get away from work on time but it’s been one of those days and well, I have to admit, knowing I am going to be caned this evening has made it hard to concentrate properly.”
I smiled and offered Michelle to join me in a coffee which she gratefully accepted. We chatted for a while in the kitchen as we enjoyed our dose of caffeine, not about anything in particular, just small talk, as in truth I was perhaps as nervous as she was about her caning.
Despite my years of experience and with countless well-punished female bottoms to my credit, being asked to administer the first ever caning to the wife of an acquaintance was a little uncomfortable for me.
I had always found Michelle attractive, extremely attractive, I could never deny that and whenever she was around, my eyes grabbed every opportunity to scrutinise this lovely woman hoping she had never noticed my attentions. Michelle had never given away her exact age, but from the conversations we’d had in the past, I knew enough to be sure she was somewhere between early and mid-forties.
With my own fortieth birthday looming, I had become aware of finding myself ever more inclined toward attractive ladies with a certain maturity. Michelle certainly fitted the bill, beautiful, elegant and displaying the gentle signs of maturity which for me had begun to surpass the freshness of the more youthful.
I knew though, that my task was to punish Michelle for the misdemeanors which Simon had informed me of, any consideration for her sexual appeal meant nothing to me – or perhaps I was just trying to k** myself!
Finishing her coffee, Michelle walked over to the sink and began to rinse the mug under the tap. As she leaned toward the sink I took the opportunity to focus on her shapely bottom, her buttocks neatly packaged within the snug fitting black jeans she was wearing.
“It’s okay, leave that Michelle, I’ll do that later, you need to go upstairs and get changed.” Somehow my tone had automatically become more formal. I often found myself slipping into role-play without even realising.
”You can use the bedroom to the left of the bathroom that you used the last time you came, and when you’re in your uniform come back down and wait outside my study.” Michelle nodded and made her way back into the hallway picking up the holdall she had brought with her which contained her school uniform.
As she set off up the stairs I smiled inwardly, recalling her husband Simon, telling me about taking Michelle to buy that uniform, feigning to the puzzled shop assistant that it was for a fancy dress party and that Michelle was going as a St. Trinian’s girl.
Simon was much older than Michelle, perhaps late fifties, maybe more. He had explained to me that he found no pleasure in punishing her himself, the act of sending her to someone else for punishment though, was far more stimulating for him.
I’d set out the study earlier, put away my computer and music system, the mix of modern technology and traditional punishment is one I’ve always preferred to avoid. As I went into the study I glanced around to make sure all was in order.
A short while later the creak of the floorboards outside the study announced Michelle’s arrival. I waited a few moments, just long enough to allow her the opportunity to sample the anguish of just standing there, which I’m sure ‘back in the day’ was as much a part of the punishment as the spanking itself.
When enough time had passed I opened the door and invited Michelle in, her pensive expression enough to let me know that despite her maturity and her fascination for corporal punishment she was as nervous as any schoolgirl would have been those decades ago when presenting herself for a caning.
Michelle had transformed herself, the sage green top and the black jeans she had been wearing on her arrival had been replaced with a navy blue blazer with a light grey braid, pale-blue blouse, diagonally striped tie, invitingly short, grey-pleated skirt and delightful white knee-length socks. She undoubtedly made a wonderful adult schoolgirl. I had seen other women in her age group similarly kitted out who in truth were really not made for such attire.
I stood on the far side of the room near my desk and looked at Michelle, her hands fidgeted nervously at her sides and her eyes looked toward the floor. “Look up Michelle and remind me why you’ve been sent here.” She raised her eyes to meet mine and I watched her lower lip quiver before she brought herself to speak.
“I was caught playing with myself Sir, trying out a new toy I’d bought with money given to me for something else”. I took in a deep breath and exhaled in a disapproving way.
“Well Michelle, I’m sure you realise that your disgraceful behaviour leaves me with no choice other than to cane you”. Michelle’s eyes widened, “Oh please Sir, not the cane, anything but the cane, I’ll do lines or extra homework and I’ll never do anything like that again I promise.” Michelle had slipped into role play well, her soft, educated tones were very convincing.
I looked at Michelle for a moment or two, again savouring her beauty as an adult schoolgirl. Michelle was tall and slender, her long auburn hair cascaded majestically onto her shoulders and in truth she looked much younger than her years. The only tell-tale sign to her maturity were the fine lines of gentle aging around her liquid, hazel eyes and adjacent her delightful, full lips. She was indeed a most beautiful woman.
Inwardly, I felt slightly embarrassed as I etched this scrutiny into my mind. From the first time I had seen Michelle I had recognised her appeal, wasting little time in including her in numerous fantasies as I’d masturbated, perhaps disappointed that in reality I’d never been privileged to see her naked bottom. Despite its undoubted beauty, Simon had made it clear to me from the outset of our arrangement that Michelle disliked displaying her bare bottom to anyone, it was just the way she was he had said.
Michelle had visited my study twice before, the first time as nervous as a rabbit in the headlights as I’d given her a firm over the knee hand spanking with her knickers drawn tight across her bottom. This had been followed by a few moderate strokes with a wooden hairbrush.
During our second encounter, we had progressed to the use of a leather paddle and leather belt, both applied across her knickers. She had told me at this time that she had often wondered what it would be like to get caned and I’m sure I had blushed as the thought of the number of canings she had received in my masturbatory fantasies flushed through my mind.
My discussions with Simon had made me aware that he believed Michelle might struggle with a hard caning, but may soon be ready for an authentic schoolgirl style caning.
With that time now reached, I had selected a 32 inch flexible crooked handle rattan cane for Michelle. It was a cane I’d owned for many years and which had darkened nicely with age. I held the cane between my hands and flexed it into a semicircle.
It was a cane which had been used on a number of errant female bottoms over the years and although some would consider it a ‘junior’ cane I have personally never liked to label my canes in that way. Whether a cane is rigid or flexible or somewhere in between, it offers its own quality and the cane I’d selected for Michelle would certainly challenge her.
With my focus for Michelle an authentic schoolgirl caning, in reality ‘back in the day’ from the time of the miscreant entering the study, canings were often swiftly delivered, it was simply a case of bend over, take your medicine and leave.
I again flexed the cane into a semicircle in front of Michelle. “I’m going to give you twelve strokes with this cane Michelle.” Her lower lip quivered and her eyes focused on the cane “Oh but Sir, I thought I was going to get six of the best, not twelve.”
I made no verbal response.
Using the cane as a pointer, I directed Michelle to my desk over which she would bend for her punishment. As she did so, I instructed her to reach forward and grip the far edge of the desk, an act which caused her skirt and blazer to rise up her body and her navy blue knickers to draw delightfully tight as her bottom thrust out.
As I again scrutinised the soon to be punished bottom, I knew that I would be unable to resist at least a couple of strokes to the exposed lower portion of her buttocks.
My desire to pull those knickers down and reveal her naked buttocks, was alas, not within my control. I even wondered whether Michelle was concealing something beneath those knickers, something she didn’t want others to see. An unattractive birthmark perhaps, or an ugly scar which she felt embarrassed to display.
I recalled a lady named Tracey whom I’d spanked some years before. A fall from the back of her boyfriend’s motorbike when she was in her teens, had sent her hurtling along the tarmac on her bottom, stripping the skin from the pinnacles of her buttocks and leaving her with permanent scarring. Although it was some years after the event when I came to know her, she was very self-conscious by the marks her ordeal had left her with. With Michelle though, my thoughts were pure speculation and in my fantasies her naked bottom was perfection itself.
Raising her skirt out of the way and tucking it into its own waistband, I pulled Michelle’s knickers taut, the lower part of them slipping into the glorious valley between her shapely cheeks, leaving the lower portion of her buttocks unprotected. Michelle’s bottom looked magnificent, a totally perfect target for the cane. I truly hoped there was nothing to blemish her beauty under those knickers.
As I squared the cane to the centre of her bottom I found it hard to imagine that anyone would not want to cane it, and to my inner embarrassment I could feel my growing arousal.
Drawing the cane back I delivered a crisp stroke across the middle of her cheeks. “OOH!” squealed Michelle. I wasted little time in applying a second and third stroke, the ‘swish’ of this flexible cane as it cut through the air and the crack as it delivered its stinging bite was pure music to my ears. Three further strokes and cries of “AAH!” and “OUCH!” from Michelle, and the caning had quickly reached its halfway point.
She had coped well and with six more strokes remaining I chose to raise the bar and make each stroke harder. To this point I had only caned her across her knickers, but the bare flesh of the lower buttock area beckoned.
To gauge her tolerance for the harder strokes I applied the next two to the centre of her bottom “OW-OW-OW! that hurts,” she yelled rocking from one foot to the other. “It’s a caning Michelle, it’s supposed to hurt,” I reminded her as she composed herself.
The next stroke was placed squarely across the exposed flesh of her lower buttocks quickly followed by another similar stroke about an inch lower. As Michelle cried out, “AAH! OW! OH GOD!” my eyes savoured the delicious parallel, vivid lines that the cane had painted on her glorious cheeks. Her knees flexed and straightened causing her bottom to bounce up and down erotically.
As she settled herself, I brushed a fingertip across those parallel lines as they rapidly blossomed into raised swellings.”OOOOH!” she responded in testimony to her soreness.
“Two more strokes Michelle,” I announced, squaring the cane to the centre of her bottom and tapping it gently on the pinnacle of her cheeks. A further swelling was occurring in my trousers and I glanced downward hoping it would not be obvious should she turn her head.
In my mind I knew that whether today remained Michelle’s only experience of being caned or whether this was to be the first of many canings for her, I owed it to her to explore her limits and feel the true potential of the cane.
Drawing the cane back I unleashed a blistering stroke across her buttocks, the sound as cane met target resembling a pistol shot. “EEE-OW-OW-OW!” wailed Michelle as she released the grip on the desk and contorted her bottom wildly. “OH MY GOD, OH MY GOD,” she continued as she slowly returned to position for the final stroke.
Drawing the cane back once more I delivered another stroke at least the equal of the previous one. It’s impact enough to cause Michelle to thrust her head back and clutch her buttocks with both hands. “OH FUCK... FUCK.. OW....WOW, WOW... THAT HURTS SO MUCH,” she shrieked as she tried to ride out her anguish.
I allowed Michelle a moment or two to compose herself, my experience as a disciplinarian was enough to make me feel that despite her vocal protests, she was not finding this an entirely unpleasant experience. I had pushed her boundaries and I sensed that like a horse broken into the saddle she was ready for more.
“How does your bottom feel now Michelle?” I asked
“It’s throbbing Sir, really throbbing,” her voice sounding strained but showing no sign of protest. I pondered for a moment before requesting her to bend over once more. “I’m going to give you three more strokes Michelle, two for using bad language and one for rubbing your bottom without permission.”
I awaited her response, had she refused or displayed any concern I would not have pursued these extra strokes but as I watched her peel down her knickers of her own volition, giving me my first ever view of her fully naked bottom and bend without complaint, I knew that Michelle was now truly absorbed.
My eyes began to scrutinise her and to my delight her bottom was every bit as beautiful as I’d imagined it was in my masturbatory fantasies. The number of times thoughts of that very bottom had brought me to the boil as I’d masturbated, I could not say, but now that it was presented to me for real I had little doubt that Michelle’s bottom would feature in my fantasies for a long time to come.
Presenting her bare bottom to me for punishment was an unexpected and welcome surprise. Michelle’s well-striped buttocks were testimony to the fact that the stretched navy blue knickers had afforded little protection from the bite of the cane and as I once more offered the cane to this wonderful naked target she turned her head to speak, “I want you to give me three hard strokes Tobias, I think that’ll be all I can take but I want to finish with three hard strokes on my bare bum.”
Michelle, it seemed, had opted out of role-play, this was no longer about two adults playing out a scene but about a woman needing to do something and asking me to do it.
Seeing Michelle’s bottom naked enabled me to see the positioning of the strokes I had already given her. The centre of her bottom had been well catered for with only the two lower strokes which I’d aimed at her bare flesh, outside this zone.
Raising the cane higher than before I brought it down hard to the unmarked upper portion of her buttocks, “OUCH, OH!” she cried as she tensed and untensed her body as a new stripe blossomed. Raising the cane again I aimed a little lower and delivered it just above the earlier collection of strokes, “ERM..m...m...m..mer,” mumbled Michelle in an attempt to stifle her protests as yet another stripe emerged.
“Okay Michelle, last stroke coming up, are you up for it?” I asked. Michelle nodded her head, ”Yes, go for it,” she replied in confident tone..
I offered the cane to Michelle’s bottom across the lower, fleshier part of her buttocks. After tapping it gently a couple of times I chose to do the customary thing and make this final stroke the hardest. Drawing the cane back I drove it against her cheeks with blistering force, the whippy rattan near moulding itself to her contours at the moment of impact. “OH MY GOD, OH MY GOD.......OH MY BUM!” she squealed as she grasped her buttocks and frantically rubbed herself.
Putting the cane down, I allowed Michelle a few moments to recover. “You okay?” I asked. “Yes, yes I’m fine, that was really, really...... something.” she replied.
With the caning now over I allowed my hand to explore the now rugged terrain of Michelle’s well-striped buttocks before slipping my fingers between her sumptuous thighs feeling the dripping warmth around her luscious cunt lips. With my thumb pressed against her throbbing arsehole I teased my fingers into her wetness as my eyes feasted on the beauty of her well caned buttocks, my free hand gently kneading and squeezing her tender flesh as I did so.
Michelle moaned with undoubted pleasure and as I gave control to what comes naturally, my cock hardened to the point of aching within the confines of my trousers.
The desire to plunge Michelle’s depths was overwhelming and had the circumstances been different I would have readily accepted either of the orifices within my grasp.
Slowly, she turned to face me, carefully kneeling before me as her eyes remained in contact with my own. It now seemed her turn to take control.
With my swollen cock molding the front of my trousers, Michelle tugged at my belt. “Why can something which hurts so much be so BLOODY arousing Tobias?” she asked as she struggled with my belt buckle.
I had no doubt this was a genuine question and as I assisted in unbuckling my belt I attempted a response, “It’s how you are Michelle, you could have been different but you’re not, you had to take the plunge to really know how a caning would make you feel and now you’ve done it.”
I’d barely finished speaking before my trousers and underpants were around my ankles. I’m not sure which of us had been most enthusiastic in this cause, but as she began working her hand to my pleasure I had no need to care.
As Michelle looked up at me, the smile on her face told me this was the point of no return and somehow I knew that this unexpected finale likely came with Simon’s approval, it was the kind of relationship they seemed to share.
Michelle continued to skilfully work me and if the bite of the cane across her magnificent buttocks had driven her to unexpected heights I too was now reaching a similar level. Had her hand been her only offering my satisfaction would have been fully assured, but as she began to employ her tongue to tease the tip of my throbbing cock, an even higher wave of pleasure surged through me.
Michelle licked me like an ice-cream and as the fingernails of her free hand tickled the base of my sack I had to muster every ounce of my willpower not to fire my seed into her mouth there and then. It was a wonderful journey and as with any ice-cream, it can only be licked for so long before the urge to suck it takes over.
With my hands placed on Michelle’s head I entwined my fingers in her thick, soft auburn hair allowing me to ride with the motion of her attentions. Grasping my naked buttocks in her hands she thrust herself back and forth, the warm, moist feel of her mouth a perfect haven for my manhood with every so often Michelle applying her teeth to nibble me whilst running the full length of my shaft, slightly hurting, yet blissfully pleasurable.
As I leaned forward and looked down, the sight of Michelle’s naked, well-striped buttocks as she thrust her pretty head back and forth was the point my crescendo was reached. This wonderful experience was destined to be short lived and as Michelle slowly rose to her feet she teasingly squeezed my cum between her teeth displaying it on her lips, before swallowing it down.
As Michelle left my study to change back into her ‘street’ clothes, my eyes were glued to her perfect, shapely bottom as she exited the room, my hopes high that she would return for another caning in the near future. One thing I could at least be certain of though; this beautiful woman would play many a starring role in my masturbatory fantasies for a long time to come.
I guess the ‘stickler for time’ in me had got the better of my imagination so I wandered into the kitchen and switched on the kettle to make a coffee. As I did so it crossed my mind that despite her husband’s earlier assurances, maybe he’d changed his mind and didn’t want Michelle punished after all.
As the water in the kettle began to warm up, the hissing sound it made broke the silence of the house. I stood and watched the kettle, remembering the words of my grandmother from when I was very small “a watched kettle never boils,” she had often said and although I knew this was just an old saying and not entirely true, I knew exactly what she meant.
The kettle did of course boil, but it did seem to take an age and as it clicked off I again glanced at the clock, it was now 6.10 pm and I was convinced that either Michelle’s husband Simon, had changed his mind about me punishing her, or Michelle herself had decided to avoid the punishment which had been requested for her.
As I stirred the milk into my coffee, the chime of the doorbell rang in my ears and I hurriedly went to answer the door, desperately hoping it wasn’t someone trying to convert me to religion or sell me magic dusters.
Through the small glass panel in the door I was relieved to see that it was Michelle and as I let her in she apologised profusely for her lateness. “I’m so sorry Tobias, I tried everything to get away from work on time but it’s been one of those days and well, I have to admit, knowing I am going to be caned this evening has made it hard to concentrate properly.”
I smiled and offered Michelle to join me in a coffee which she gratefully accepted. We chatted for a while in the kitchen as we enjoyed our dose of caffeine, not about anything in particular, just small talk, as in truth I was perhaps as nervous as she was about her caning.
Despite my years of experience and with countless well-punished female bottoms to my credit, being asked to administer the first ever caning to the wife of an acquaintance was a little uncomfortable for me.
I had always found Michelle attractive, extremely attractive, I could never deny that and whenever she was around, my eyes grabbed every opportunity to scrutinise this lovely woman hoping she had never noticed my attentions. Michelle had never given away her exact age, but from the conversations we’d had in the past, I knew enough to be sure she was somewhere between early and mid-forties.
With my own fortieth birthday looming, I had become aware of finding myself ever more inclined toward attractive ladies with a certain maturity. Michelle certainly fitted the bill, beautiful, elegant and displaying the gentle signs of maturity which for me had begun to surpass the freshness of the more youthful.
I knew though, that my task was to punish Michelle for the misdemeanors which Simon had informed me of, any consideration for her sexual appeal meant nothing to me – or perhaps I was just trying to k** myself!
Finishing her coffee, Michelle walked over to the sink and began to rinse the mug under the tap. As she leaned toward the sink I took the opportunity to focus on her shapely bottom, her buttocks neatly packaged within the snug fitting black jeans she was wearing.
“It’s okay, leave that Michelle, I’ll do that later, you need to go upstairs and get changed.” Somehow my tone had automatically become more formal. I often found myself slipping into role-play without even realising.
”You can use the bedroom to the left of the bathroom that you used the last time you came, and when you’re in your uniform come back down and wait outside my study.” Michelle nodded and made her way back into the hallway picking up the holdall she had brought with her which contained her school uniform.
As she set off up the stairs I smiled inwardly, recalling her husband Simon, telling me about taking Michelle to buy that uniform, feigning to the puzzled shop assistant that it was for a fancy dress party and that Michelle was going as a St. Trinian’s girl.
Simon was much older than Michelle, perhaps late fifties, maybe more. He had explained to me that he found no pleasure in punishing her himself, the act of sending her to someone else for punishment though, was far more stimulating for him.
I’d set out the study earlier, put away my computer and music system, the mix of modern technology and traditional punishment is one I’ve always preferred to avoid. As I went into the study I glanced around to make sure all was in order.
A short while later the creak of the floorboards outside the study announced Michelle’s arrival. I waited a few moments, just long enough to allow her the opportunity to sample the anguish of just standing there, which I’m sure ‘back in the day’ was as much a part of the punishment as the spanking itself.
When enough time had passed I opened the door and invited Michelle in, her pensive expression enough to let me know that despite her maturity and her fascination for corporal punishment she was as nervous as any schoolgirl would have been those decades ago when presenting herself for a caning.
Michelle had transformed herself, the sage green top and the black jeans she had been wearing on her arrival had been replaced with a navy blue blazer with a light grey braid, pale-blue blouse, diagonally striped tie, invitingly short, grey-pleated skirt and delightful white knee-length socks. She undoubtedly made a wonderful adult schoolgirl. I had seen other women in her age group similarly kitted out who in truth were really not made for such attire.
I stood on the far side of the room near my desk and looked at Michelle, her hands fidgeted nervously at her sides and her eyes looked toward the floor. “Look up Michelle and remind me why you’ve been sent here.” She raised her eyes to meet mine and I watched her lower lip quiver before she brought herself to speak.
“I was caught playing with myself Sir, trying out a new toy I’d bought with money given to me for something else”. I took in a deep breath and exhaled in a disapproving way.
“Well Michelle, I’m sure you realise that your disgraceful behaviour leaves me with no choice other than to cane you”. Michelle’s eyes widened, “Oh please Sir, not the cane, anything but the cane, I’ll do lines or extra homework and I’ll never do anything like that again I promise.” Michelle had slipped into role play well, her soft, educated tones were very convincing.
I looked at Michelle for a moment or two, again savouring her beauty as an adult schoolgirl. Michelle was tall and slender, her long auburn hair cascaded majestically onto her shoulders and in truth she looked much younger than her years. The only tell-tale sign to her maturity were the fine lines of gentle aging around her liquid, hazel eyes and adjacent her delightful, full lips. She was indeed a most beautiful woman.
Inwardly, I felt slightly embarrassed as I etched this scrutiny into my mind. From the first time I had seen Michelle I had recognised her appeal, wasting little time in including her in numerous fantasies as I’d masturbated, perhaps disappointed that in reality I’d never been privileged to see her naked bottom. Despite its undoubted beauty, Simon had made it clear to me from the outset of our arrangement that Michelle disliked displaying her bare bottom to anyone, it was just the way she was he had said.
Michelle had visited my study twice before, the first time as nervous as a rabbit in the headlights as I’d given her a firm over the knee hand spanking with her knickers drawn tight across her bottom. This had been followed by a few moderate strokes with a wooden hairbrush.
During our second encounter, we had progressed to the use of a leather paddle and leather belt, both applied across her knickers. She had told me at this time that she had often wondered what it would be like to get caned and I’m sure I had blushed as the thought of the number of canings she had received in my masturbatory fantasies flushed through my mind.
My discussions with Simon had made me aware that he believed Michelle might struggle with a hard caning, but may soon be ready for an authentic schoolgirl style caning.
With that time now reached, I had selected a 32 inch flexible crooked handle rattan cane for Michelle. It was a cane I’d owned for many years and which had darkened nicely with age. I held the cane between my hands and flexed it into a semicircle.
It was a cane which had been used on a number of errant female bottoms over the years and although some would consider it a ‘junior’ cane I have personally never liked to label my canes in that way. Whether a cane is rigid or flexible or somewhere in between, it offers its own quality and the cane I’d selected for Michelle would certainly challenge her.
With my focus for Michelle an authentic schoolgirl caning, in reality ‘back in the day’ from the time of the miscreant entering the study, canings were often swiftly delivered, it was simply a case of bend over, take your medicine and leave.
I again flexed the cane into a semicircle in front of Michelle. “I’m going to give you twelve strokes with this cane Michelle.” Her lower lip quivered and her eyes focused on the cane “Oh but Sir, I thought I was going to get six of the best, not twelve.”
I made no verbal response.
Using the cane as a pointer, I directed Michelle to my desk over which she would bend for her punishment. As she did so, I instructed her to reach forward and grip the far edge of the desk, an act which caused her skirt and blazer to rise up her body and her navy blue knickers to draw delightfully tight as her bottom thrust out.
As I again scrutinised the soon to be punished bottom, I knew that I would be unable to resist at least a couple of strokes to the exposed lower portion of her buttocks.
My desire to pull those knickers down and reveal her naked buttocks, was alas, not within my control. I even wondered whether Michelle was concealing something beneath those knickers, something she didn’t want others to see. An unattractive birthmark perhaps, or an ugly scar which she felt embarrassed to display.
I recalled a lady named Tracey whom I’d spanked some years before. A fall from the back of her boyfriend’s motorbike when she was in her teens, had sent her hurtling along the tarmac on her bottom, stripping the skin from the pinnacles of her buttocks and leaving her with permanent scarring. Although it was some years after the event when I came to know her, she was very self-conscious by the marks her ordeal had left her with. With Michelle though, my thoughts were pure speculation and in my fantasies her naked bottom was perfection itself.
Raising her skirt out of the way and tucking it into its own waistband, I pulled Michelle’s knickers taut, the lower part of them slipping into the glorious valley between her shapely cheeks, leaving the lower portion of her buttocks unprotected. Michelle’s bottom looked magnificent, a totally perfect target for the cane. I truly hoped there was nothing to blemish her beauty under those knickers.
As I squared the cane to the centre of her bottom I found it hard to imagine that anyone would not want to cane it, and to my inner embarrassment I could feel my growing arousal.
Drawing the cane back I delivered a crisp stroke across the middle of her cheeks. “OOH!” squealed Michelle. I wasted little time in applying a second and third stroke, the ‘swish’ of this flexible cane as it cut through the air and the crack as it delivered its stinging bite was pure music to my ears. Three further strokes and cries of “AAH!” and “OUCH!” from Michelle, and the caning had quickly reached its halfway point.
She had coped well and with six more strokes remaining I chose to raise the bar and make each stroke harder. To this point I had only caned her across her knickers, but the bare flesh of the lower buttock area beckoned.
To gauge her tolerance for the harder strokes I applied the next two to the centre of her bottom “OW-OW-OW! that hurts,” she yelled rocking from one foot to the other. “It’s a caning Michelle, it’s supposed to hurt,” I reminded her as she composed herself.
The next stroke was placed squarely across the exposed flesh of her lower buttocks quickly followed by another similar stroke about an inch lower. As Michelle cried out, “AAH! OW! OH GOD!” my eyes savoured the delicious parallel, vivid lines that the cane had painted on her glorious cheeks. Her knees flexed and straightened causing her bottom to bounce up and down erotically.
As she settled herself, I brushed a fingertip across those parallel lines as they rapidly blossomed into raised swellings.”OOOOH!” she responded in testimony to her soreness.
“Two more strokes Michelle,” I announced, squaring the cane to the centre of her bottom and tapping it gently on the pinnacle of her cheeks. A further swelling was occurring in my trousers and I glanced downward hoping it would not be obvious should she turn her head.
In my mind I knew that whether today remained Michelle’s only experience of being caned or whether this was to be the first of many canings for her, I owed it to her to explore her limits and feel the true potential of the cane.
Drawing the cane back I unleashed a blistering stroke across her buttocks, the sound as cane met target resembling a pistol shot. “EEE-OW-OW-OW!” wailed Michelle as she released the grip on the desk and contorted her bottom wildly. “OH MY GOD, OH MY GOD,” she continued as she slowly returned to position for the final stroke.
Drawing the cane back once more I delivered another stroke at least the equal of the previous one. It’s impact enough to cause Michelle to thrust her head back and clutch her buttocks with both hands. “OH FUCK... FUCK.. OW....WOW, WOW... THAT HURTS SO MUCH,” she shrieked as she tried to ride out her anguish.
I allowed Michelle a moment or two to compose herself, my experience as a disciplinarian was enough to make me feel that despite her vocal protests, she was not finding this an entirely unpleasant experience. I had pushed her boundaries and I sensed that like a horse broken into the saddle she was ready for more.
“How does your bottom feel now Michelle?” I asked
“It’s throbbing Sir, really throbbing,” her voice sounding strained but showing no sign of protest. I pondered for a moment before requesting her to bend over once more. “I’m going to give you three more strokes Michelle, two for using bad language and one for rubbing your bottom without permission.”
I awaited her response, had she refused or displayed any concern I would not have pursued these extra strokes but as I watched her peel down her knickers of her own volition, giving me my first ever view of her fully naked bottom and bend without complaint, I knew that Michelle was now truly absorbed.
My eyes began to scrutinise her and to my delight her bottom was every bit as beautiful as I’d imagined it was in my masturbatory fantasies. The number of times thoughts of that very bottom had brought me to the boil as I’d masturbated, I could not say, but now that it was presented to me for real I had little doubt that Michelle’s bottom would feature in my fantasies for a long time to come.
Presenting her bare bottom to me for punishment was an unexpected and welcome surprise. Michelle’s well-striped buttocks were testimony to the fact that the stretched navy blue knickers had afforded little protection from the bite of the cane and as I once more offered the cane to this wonderful naked target she turned her head to speak, “I want you to give me three hard strokes Tobias, I think that’ll be all I can take but I want to finish with three hard strokes on my bare bum.”
Michelle, it seemed, had opted out of role-play, this was no longer about two adults playing out a scene but about a woman needing to do something and asking me to do it.
Seeing Michelle’s bottom naked enabled me to see the positioning of the strokes I had already given her. The centre of her bottom had been well catered for with only the two lower strokes which I’d aimed at her bare flesh, outside this zone.
Raising the cane higher than before I brought it down hard to the unmarked upper portion of her buttocks, “OUCH, OH!” she cried as she tensed and untensed her body as a new stripe blossomed. Raising the cane again I aimed a little lower and delivered it just above the earlier collection of strokes, “ERM..m...m...m..mer,” mumbled Michelle in an attempt to stifle her protests as yet another stripe emerged.
“Okay Michelle, last stroke coming up, are you up for it?” I asked. Michelle nodded her head, ”Yes, go for it,” she replied in confident tone..
I offered the cane to Michelle’s bottom across the lower, fleshier part of her buttocks. After tapping it gently a couple of times I chose to do the customary thing and make this final stroke the hardest. Drawing the cane back I drove it against her cheeks with blistering force, the whippy rattan near moulding itself to her contours at the moment of impact. “OH MY GOD, OH MY GOD.......OH MY BUM!” she squealed as she grasped her buttocks and frantically rubbed herself.
Putting the cane down, I allowed Michelle a few moments to recover. “You okay?” I asked. “Yes, yes I’m fine, that was really, really...... something.” she replied.
With the caning now over I allowed my hand to explore the now rugged terrain of Michelle’s well-striped buttocks before slipping my fingers between her sumptuous thighs feeling the dripping warmth around her luscious cunt lips. With my thumb pressed against her throbbing arsehole I teased my fingers into her wetness as my eyes feasted on the beauty of her well caned buttocks, my free hand gently kneading and squeezing her tender flesh as I did so.
Michelle moaned with undoubted pleasure and as I gave control to what comes naturally, my cock hardened to the point of aching within the confines of my trousers.
The desire to plunge Michelle’s depths was overwhelming and had the circumstances been different I would have readily accepted either of the orifices within my grasp.
Slowly, she turned to face me, carefully kneeling before me as her eyes remained in contact with my own. It now seemed her turn to take control.
With my swollen cock molding the front of my trousers, Michelle tugged at my belt. “Why can something which hurts so much be so BLOODY arousing Tobias?” she asked as she struggled with my belt buckle.
I had no doubt this was a genuine question and as I assisted in unbuckling my belt I attempted a response, “It’s how you are Michelle, you could have been different but you’re not, you had to take the plunge to really know how a caning would make you feel and now you’ve done it.”
I’d barely finished speaking before my trousers and underpants were around my ankles. I’m not sure which of us had been most enthusiastic in this cause, but as she began working her hand to my pleasure I had no need to care.
As Michelle looked up at me, the smile on her face told me this was the point of no return and somehow I knew that this unexpected finale likely came with Simon’s approval, it was the kind of relationship they seemed to share.
Michelle continued to skilfully work me and if the bite of the cane across her magnificent buttocks had driven her to unexpected heights I too was now reaching a similar level. Had her hand been her only offering my satisfaction would have been fully assured, but as she began to employ her tongue to tease the tip of my throbbing cock, an even higher wave of pleasure surged through me.
Michelle licked me like an ice-cream and as the fingernails of her free hand tickled the base of my sack I had to muster every ounce of my willpower not to fire my seed into her mouth there and then. It was a wonderful journey and as with any ice-cream, it can only be licked for so long before the urge to suck it takes over.
With my hands placed on Michelle’s head I entwined my fingers in her thick, soft auburn hair allowing me to ride with the motion of her attentions. Grasping my naked buttocks in her hands she thrust herself back and forth, the warm, moist feel of her mouth a perfect haven for my manhood with every so often Michelle applying her teeth to nibble me whilst running the full length of my shaft, slightly hurting, yet blissfully pleasurable.
As I leaned forward and looked down, the sight of Michelle’s naked, well-striped buttocks as she thrust her pretty head back and forth was the point my crescendo was reached. This wonderful experience was destined to be short lived and as Michelle slowly rose to her feet she teasingly squeezed my cum between her teeth displaying it on her lips, before swallowing it down.
As Michelle left my study to change back into her ‘street’ clothes, my eyes were glued to her perfect, shapely bottom as she exited the room, my hopes high that she would return for another caning in the near future. One thing I could at least be certain of though; this beautiful woman would play many a starring role in my masturbatory fantasies for a long time to come.
Mila
- 13.02.2020
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