The Awakening of a Cougar Part 1
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The Awakening of a Cougar
With Debbie remaining across my lap I inspected her bottom. Her cheeks had coloured a luscious shade of red, the evenness of tone telling me that I had succeeded in ensuring that no accessible part of her bottom had been left unchallenged. As I eased those cheeks apart, the contrast between the paleness of her cleft and the glow of her spanked flesh added further testimony to the effectiveness of my hand. It also afforded a view of her neatly puckered anus, reminding me once more of that recent fantasy whilst fucking Sandra!
Eventually, I gave Debbie permission to rub herself. “My bottom really stings Sir,” she announced as she used her hands in an attempt to quell her discomfort. I reminded her that a spanking is supposed to sting. Allowing my own hand to join the act, I smoothed it over the contours of her warm and beautiful buttocks, pausing occasionally to knead and squeeze this captivating flesh, making her wince as I did so.
Debbie was then placed in a standing position facing the corner of the room like the naughty girl that she was. The confession she’d made to me on her arrival had earned her eighteen strokes of the cane beyond the hand spanking.
Although, Debbie’s level of tolerance had grown impressively since she had first come to me, I was aware that to this point she’d never taken more than twelve strokes of the cane in one go and as a relative newcomer to corporal punishment, despite her personal desire to push her boundaries, I had a duty to avoid taking her too far too soon, maybe even scaring her off for good.
One of my own early experiences within the world of corporal punishment had proved a near disaster. My interest in CP had been with me from an early age and with no real experience, just a few days after my nineteenth birthday, I had taken the plunge and travelled well away from my home area to visit a ‘headmistress’ whose services I’d seen advertised in a contact magazine. I’d had to tell her I was over twenty-one, although in truth, I was often told that I looked younger than my true age.
Although the essence in my mind was for me to spank others, and many an attractive young lady had roused my passions for this. At this youthful age, my naivety was such that I believed that I would never meet a girl who would agree to being spanked, even doubting such girls existed for real.
I’d tried introducing girlfriends to spanking but without success. Visiting the ‘Headmistress’ seemed the only alternative, and if nothing else, it would at least allow me some involvement in the world of corporal punishment that I so craved. Yes, better to get a flavour of the ambience by getting my own bottom punished than to simply thrive on my fantasies.
The ‘Headmistress’ I visited was in her mid-thirties I guessed, and attractive enough for me to wish that it was me punishing her. On my arrival I was taken into the lounge of her large Victorian terrace as we discussed what I wanted from the session over a coffee.
I asked for a range of implements and a hard caning, unwisely saying that I had been spanked and caned many times before and could withstand firm punishment.
In truth my only experience to date had been a couple of encounters with the slipper and strap at school. More latterly though, I’d taken to experimenting spanking myself, often sneaking down to the shed at the end of the garden and utilising whatever I could find for the purpose, usually ending up caning my own bare buttocks with a cane intended for supporting delphiniums.
As I discussed my intentions with the ‘Headmistress,’ my private philosophy was that when real punishment was meted out there was no choice for the recipient as to how hard it would be. After all, those who found themselves bent over for a caning in the Head’s study had little say regarding the severity of the punishment they would receive.
I really wanted to know what a proper spanking and caning would feel like, not just someone taking it easy on a youngster who admitted to little or no experience.
Yes, I was determined to feel the cane as it was meant to be. With coffee consumed I was then taken to the ‘study’ in the basement of the house, at which point I cannot deny that the butterflies in my stomach began doing acrobatics.
To facilitate role play I'd confessed to masturbating about girls I was familiar with. At this time, barely a year since I had actually left school, there were numerous girls from my schooldays still active in my mind, even a couple of the younger female teachers thrown in for good measure. All of them still played a part in fuelling my masturbatory fantasies time and time again.
Well away from home territory I used their real names, admitted to the fantasies I’d had for them, well, the fantasies I was prepared to divulge at least!
The ‘Headmistress’ seemed genuinely interested in me, apparently her staple custom was middle-aged and older men, usually business types and she openly admitted that having a handsome (her judgement) and much younger man with a firm, tight bottom, eminently preferable to the overweight men with unappealing bottoms that usually frequented her study.
With her mortarboard and gown donned, she certainly looked the part and I just knew I wasn’t going to get off lightly. I had booked and paid for an hour with this lady, almost exhausting my savings at this time, but with no further bookings that afternoon, she allowed me to stay for over twice the time at no extra cost.
By the end of my visit I had endured the ‘Headmistress’s hand to warm me up before progressing to a variety of implements; ruler, gym shoe, paddle, strap, to name but a few. The finale was of course, the cane, a variety of canes in fact, and my poor bottom suffered mercilessly.
With it impossible to estimate how many strokes I’d received, the ‘Headmistress’ eventually lowered the cane, concerned that further strokes may begin to draw blood.
I’d coped well, even the ‘Headmistress’ congratulated me on my stoicism as she massaged cream into my ravaged buttocks before deliciously working my cock with her hand to the point of release, but as I left her house and walked stiffly to my car parked some distance down the street, I began to question myself. At that moment in time I made the decision that I would never have anything to do with corporal punishment again.
I had truly discovered what it was like to be punished for real and was grateful for that, but as my buttocks throbbed and the pain of each stroke inflicted on them was so fresh in my mind, I decided that I never wanted to be in this position again. My return journey was uncomfortable to say the least and as I drove the sixty or so miles back home, I vowed that I would never put myself through anything like this again.
No, this wasn’t for me and now that I really knew the true agony of being on the receiving end of strict corporal punishment any desire to inflict it on others seemed to have also evaporated in one fell swoop!
Even my fantasies held no more appeal. The numerous attractive young ladies who had previously captured my thoughts and been mercilessly spanked and caned to my pleasure were owed an apology in my mind. Corporal punishment wasn’t fun, it wasn’t sexy, it was barbaric!
Nothing at this time would ever have made me believe that I would be back to visit the ‘Headmistress’ again and again over the following two years, baring my bottom for more of the same and actually growing to like it.
As Debbie remained in the corner, I took every opportunity to study her beautiful bottom. I knew that it would likely be a few weeks before I saw her again and although I would doubtless spank other bottoms in that time, it was hers that I wanted etched in my mind. Her bottom was undoubtedly the crème de la crème of bottoms for me at this time.
After moving the chair I had sat on for her spanking, I instructed Debbie to bend over the desk, a plump velvet cushion placed neatly beneath her belly as she leaned forward. The cushion caused Debbie’s bottom to rise delightfully and to form a wonderfully accessible target.
“I’m going to give you three lots of six strokes Debbie,” I informed her. “So maybe the next time you attend a party you’ll remember this caning and behave in a more appropriate way.”
Debbie turned her head towards me, “I’m sure I will Sir, I’ll never do anything like that again I promise, but I know that I deserve to be caned.”
I selected the first cane that I would use on her. It was a light, whippy cane with a crooked handle and although capable of inflicting a mighty sting it would provide a relatively tolerable start to her caning.
“Six strokes with this cane Debbie,” I informed her as I squared the cane to the centre of her gloriously reddened bottom. “Are you ready?”
Debbie tucked her hair behind her ears and then reached forward to clutch the far edge of the desk before responding, “Okay Sir, I’m ready.” There was an air of trepidation in her voice, perhaps only to be expected from someone about to receive eighteen strokes of the cane on their bare bottom.
I allowed myself a moment to savour the scene, the beautiful reddened buttocks, the sight of her vagina and its surrounding enchanted forest of pubic hair peering so provocatively between the tops of her shapely thighs. Yes, her bottom was indeed a perfect target for the cane!
I tested the flexible rattan through the air, it’s delicious swish as I did so causing Debbie to flinch, unsure whether she was about to feel the cane’s first bite upon her already challenged flesh.
After tapping the cane against her I drew it back, before delivering the first stroke squarely and firmly across the very buttocks that so captured my imagination. “Ouch, God, that stung,” her response.
Once more I squared the cane to its target and as it bit into Debbie’s flesh for the second time, she yelled, “OW-AH-OW.”
I recalled using this same cane a few weeks before and after administering ‘six of the best’ to the usually resilient recipient, I suggested, “I bet you hardly felt that.”
Her response, “You’re joking, that cane might be thin, but it really, really, bloody stings.”
As I continued to cane Debbie, I delighted in the sight of the narrow pink stripes that began to emerge on her cheeks and with only one stroke of this particular cane remaining she knew what to expect and without encouragement, squeezed the far edge of the desk ever more tightly as she braced herself for the hardest stroke yet.
I wasted little time in painting that final stripe across her mouth-watering bottom. As a deep intake of breath hissed through her teeth, she finally gave way to a cry of, “EEE-OW-OW-OW!” With permission given, she stood up and tended her wounds, attempting to rub away some of her anguish with her hands.
“So, do you still think it was worth sucking those cocks now?” I asked her. “I’m not so sure Sir,” she replied coyly.
I paused for a few moments to allow Debbie some respite, and before selecting the second cane I would be using, I ran my fingertips across the contours of her bottom delighting in the feel of the slender raised weals which now embossed it.
For the next six strokes I had chosen one of my favourite and perhaps, most used canes. A straight cane with a leather handle, medium thickness and undoubtedly more challenging than the first.
After ordering her to bend forward, I watched in readiness as she went through the process of tucking her hair behind her ears. For whatever reason, I always enjoyed seeing her do this.
As before, I tested the cane through the air and once more Debbie flinched. I decided to apply this cane swiftly, six strokes in quick succession and as I offered the cane to the centre of her bottom, I advised her of this.
Drawing the cane back, I brought it down to meet its target firmly and squarely, and as stroke followed stroke she contorted frantically as I varied my aim to spread the onslaught.
With barely enough time between each stroke for Debbie to catch her breath before the next searing bite cut into her flesh, her vocal responses were muffled and indistinguishable amidst her contortions, but as the final and hardest stroke with this cane landed with a resounding ‘thwack’ across the lower part of her buttocks she was more than able to make up for this, “OW-OW-OW… OH, AH, AH, AH…...OH FUCK, .... FUCK, FUCK…OH, Oh fuck,” she exuded in breathless fashion.
As Debbie rubbed herself, my eyes became focused on her well striped cheeks, those majestic buttocks that I had become so obsessed with since the very first time she had slipped down her panties and presented them to me bare.
Placing the cane on the desk I moved to stand behind her. I wanted to be close to that bottom, the bottom I had just caned and would soon cane again in order to complete her punishment. I felt compelled to scrutinise the fruits of my labour, satisfy my passion for the way nature had created this truly wonderful rear and how the cane had left its mark.
As I ran my fingertips over her contours enjoying the feel of the swollen ridges, “OOOH,” squealed Debbie as my touch reignited some of her discomfort. “Is your bottom very sore Debbie?” I enquired. “Yes, it’s really, really sore, it really does hurt,” she replied emphatically.
“So, what do you think about sucking those cocks now Debbie?” I just had to ask. “I wish I hadn’t done it Sir, my bottom hurts so much from the cane.”
I stepped back and allowed Debbie a few more moments to rub herself. No matter what happened, I intended the finale to this caning to take Debbie to a new limit and I had little doubt that this was what she wanted also.
“Okay Debbie, bend back over it’s time for your final six,” I informed her. “Oh, please Sir, I’ve learnt my lesson do I really have to have more with the cane, perhaps I could suck your cock to make up for my bad behaviour instead?”
I pondered my response, privately grinning as I did so, confident that Debbie was just adding drama to the role play. “Perhaps I should get on with the remainder of your caning and then get you to suck my cock,” I eventually responded.
Debbie hung her head. “Very well Sir, I suppose I deserve it,” she responded quietly.
Debbie once more went through the process of tucking her thick, auburn hair behind her ears before again stretching across the desk. As she did so, I was reminded of her earlier admission, “It takes something really special to get me properly aroused, normal stuff just doesn’t really do it for me.” Perhaps corporal punishment was proving to be that something ‘really special’, something that I imagined her likely vanilla marriage had not afforded her.
The cane I had selected for the final six strokes was heavier than the previous two, thicker and less flexible and I knew from using it on other female bottoms, it would doubtless present a true challenge to Debbie.
Clasping the cane close to its crook handle I offered it to her buttocks, again delighting in the view of my target whilst unable to avoid the thought of being sucked by this captivating woman when her caning was complete.
The previous cane strokes had left their mark and I was convinced that even if I added no further challenge to her bottom, very soon the angry weals she already displayed, would blossom into an array of colourful hues that would decorate her cheeks for a while to come.
As before, I tested the cane through the air and once more Debbie flinched. The sound of this heavier implement as it descended through the air, enough to confirm to her the anguish ahead.
“Okay Debbie, six more strokes and your caning is over,” I advised her. “Yes Sir,” she replied as she further fidgeted into position.
“This time I want you to count each stroke aloud after you’ve received it, is that clear?” I informed her. “Yes Sir, perfectly clear,” she replied nervously.
As I drew the cane back for the first stroke, Debbie pulled her shoulders down in anticipation of its bite and as it landed with a resounding ‘thwack’ across the centre of her bottom she thrust her head back wailing, “EEE-OW-OW-OW!” as she did so. Debbie contorted wildly before returning to position and regaining her composure. “One Sir,” she added, perhaps knowing that failure to do so would mean the stroke didn’t count.
Placing the cane a little higher on her buttocks, I focused on a gap between two of the earlier strokes she’d received. Drawing it back for the second stroke I brought it down briskly and as the cane met its target Debbie once more thrust back her head, simultaneously arching her spine, as she cried, “OW-AH-OW....OH……..BLOODY, BLOODYHELL.” As she fought to recompose, my eyes traversed her buttocks satisfying myself that the white line I had just painted with the cane was positioned exactly as intended. Barely had this line had time to flush deep red before Debbie responded with, “Two Sir,”
Drawing the cane back for the third time, I brought it down with a resounding ‘thwack’ across the lower part of her bottom just a fraction below an earlier weal. “EEE-OW-OW-WOW!” she wailed, “OH GOD, OH GOD.” Debbie again contorted her bottom wildly and tensed and untensed her knees in an attempt to quell her discomfort before returning to position.
“Three Sir,” she added, her voice strained and with her perhaps close to tears.
“Just three more strokes to go for sucking those cocks Debbie,” I informed her. Debbie steadied herself and nodded her head, “Okay, I’m ready for them,” she added.
For a moment I opted out of role play aware that I was taking Debbie beyond anything we had done before. “Do you want to stop?” I asked, adding, “I know this is much harder than you’ve had before.” Debbie shook her head, “No, no, my bum’s throbbing like hell, really burning too, but I really want to see this through.”
Placing my hand on her bottom I gently smoothed her cheeks. The feel of the warmth that radiated from them and the rugged texture of their surface leaving me in no doubt that if she didn’t know before, Debbie certainly now knew what a proper caning felt like. Allowing a finger to probe between her legs, the damp and sticky feel of her labia enough to tell me that perhaps, just perhaps Debbie was close to finding that ‘something really special’ that ‘normal stuff’ just didn’t afford her!
With my cock now stirring within my trousers, I returned to my role, wasting little time in delivering the fourth stroke to Debbie’s beckoning bottom, again trying to find a gap between the earlier strokes. As the cane once more bit into her she thrust herself upright, her auburn hair flailing wildly as she clasped her buttocks in her hands, “OW-WOW-WOW……..AH-OW....OH SHIT, FOUR SIR” she cried as she rocked from foot to foot.
“How does your bottom feel now Debbie?” I asked. “Oh, Oh, it feels like it’s been roasted,” she replied. “Okay Debbie, just two more then it’s all over,” I reminded her, confident she was already perfectly aware of this.
I watched Debbie as she once more tucked her hair behind her ears before returning to position. Why I found this action so arousing, I’m really not sure.
The penultimate stroke landed firmly onto the upper part of her buttocks, Debbie jolted back and again grasped her bottom with both hands. “OH, FUCK, .... FUCK, FUCK, sorry Sir, but my bum feels like it’s on fire,” she squealed before adding, “Five Sir”.
As Debbie bent back down for her final stroke, my eyes focused on the delightful crease where bottom and thigh merge, “One more stroke Debbie, what’s special about the last stroke?” I simply couldn’t resist teasing her. “I’d like to say it’s the softest Sir, but I know it’s going to be the hardest,” she replied with an air of trepidation, but perhaps also intermixed with an air of invitation.
My view of the side of Debbie’s face was enough to tell me that she had screwed up everything in anticipation and as I raised the cane for the final time and brought it down firmly a fraction above her crease, she all but climbed onto the desk. Debbie let out a piercing shriek which echoed around the room, simultaneously clutching her behind and rubbing herself wildly. “OH FUCK, BASTARD, HELL, THAT REALLY BLOODY HURT,” she yelled.
In normal circumstances I had never heard this normally genteel woman use any such expletives, but then again, these could not be considered normal circumstances. Perhaps in time, I would scold her for such outbursts, maybe add further strokes, but at this moment, this was not my purpose.
As I visually studied Debbie’s bottom it was clear to see that each cane stroke had left its print, angry raised weals adorned her cheeks and made a stimulating surface for my fingers to explore as I assisted in easing her anguish. I could only imagine the colourful patterns that would blossom to decorate these beautiful buttocks in a day or so. As I scrutinised her ravaged bottom, I so wanted its image etched in my mind for the future fantasies I would doubtless have about this glorious woman.
Debbie was undoubtedly close to tears, but somehow there was an elation within her that told me that she had enjoyed every agonising stroke. Although she would perhaps not do it all again this very minute, I had little doubt that she would be back for more of the same in the future.
With the cane discarded, I allowed Debbie a few precious moments to tend her wounds and regain her composure, my tingling cock eager for her oral attentions. As she turned to face me, I placed a finger under her chin and looked into her liquid blue eyes, “Well Debbie, now that you’ve had your punishment, do you think you’ll be so keen to go sucking the cocks of the young lads you’re in charge of at work?” Debbie shook her head, “No Sir, I’ll never, ever do it again, I promise.”
Reaching downwards, I offered a finger to her vagina, enjoying the feel of the coarseness of her bush as I did so. Debbie was wet, delightfully wet and there was little doubt that the cane had produced the desired effect.
Although I have always taken personal pride in controlling my emotions when administering corporal punishment, Debbie had challenged this. It was a challenge I had lost as the thin, cord-drawn casual trousers I was wearing concealed little of my arousal.
“Well, Debbie, just in case you ever forget the promise you have made and find yourself back here for another caning, I think you'd better show me exactly what it was you did to those two young men at your workplace,” I said.
Debbie nodded ashamedly, convincing me that in the few months since she had first presented herself in my study, the advancement in her role-playing skills was perhaps equal to her advancement in withstanding corporal punishment.
I watched intently and eagerly as Debbie slowly dropped to her knees and once more went through the process of tucking her hair behind her ears. I made no movement as she took hold of the cord around my waist and pulled open the simple bow that held it taut. As she coaxed my trousers and underpants down my legs, I was now delightfully at her mercy.
Wrapping her fingers around my cock, Debbie began to work me with her hand, whilst simultaneously licking and sucking the tip of my penis.
As I reached unparalleled hardness, she drew me into her mouth nibbling her way down my shaft, the feel of her teeth pressing against my skin, slightly hurting, yet blissfully pleasurable, as she did so. Clasping my buttocks tightly in her hands, she began to work her head back and forth and as I slid my fingers into her hair to ride with her motion, there could be little doubt that the cougar within Debbie was now fully awakened!
The end.
With Debbie remaining across my lap I inspected her bottom. Her cheeks had coloured a luscious shade of red, the evenness of tone telling me that I had succeeded in ensuring that no accessible part of her bottom had been left unchallenged. As I eased those cheeks apart, the contrast between the paleness of her cleft and the glow of her spanked flesh added further testimony to the effectiveness of my hand. It also afforded a view of her neatly puckered anus, reminding me once more of that recent fantasy whilst fucking Sandra!
Eventually, I gave Debbie permission to rub herself. “My bottom really stings Sir,” she announced as she used her hands in an attempt to quell her discomfort. I reminded her that a spanking is supposed to sting. Allowing my own hand to join the act, I smoothed it over the contours of her warm and beautiful buttocks, pausing occasionally to knead and squeeze this captivating flesh, making her wince as I did so.
Debbie was then placed in a standing position facing the corner of the room like the naughty girl that she was. The confession she’d made to me on her arrival had earned her eighteen strokes of the cane beyond the hand spanking.
Although, Debbie’s level of tolerance had grown impressively since she had first come to me, I was aware that to this point she’d never taken more than twelve strokes of the cane in one go and as a relative newcomer to corporal punishment, despite her personal desire to push her boundaries, I had a duty to avoid taking her too far too soon, maybe even scaring her off for good.
One of my own early experiences within the world of corporal punishment had proved a near disaster. My interest in CP had been with me from an early age and with no real experience, just a few days after my nineteenth birthday, I had taken the plunge and travelled well away from my home area to visit a ‘headmistress’ whose services I’d seen advertised in a contact magazine. I’d had to tell her I was over twenty-one, although in truth, I was often told that I looked younger than my true age.
Although the essence in my mind was for me to spank others, and many an attractive young lady had roused my passions for this. At this youthful age, my naivety was such that I believed that I would never meet a girl who would agree to being spanked, even doubting such girls existed for real.
I’d tried introducing girlfriends to spanking but without success. Visiting the ‘Headmistress’ seemed the only alternative, and if nothing else, it would at least allow me some involvement in the world of corporal punishment that I so craved. Yes, better to get a flavour of the ambience by getting my own bottom punished than to simply thrive on my fantasies.
The ‘Headmistress’ I visited was in her mid-thirties I guessed, and attractive enough for me to wish that it was me punishing her. On my arrival I was taken into the lounge of her large Victorian terrace as we discussed what I wanted from the session over a coffee.
I asked for a range of implements and a hard caning, unwisely saying that I had been spanked and caned many times before and could withstand firm punishment.
In truth my only experience to date had been a couple of encounters with the slipper and strap at school. More latterly though, I’d taken to experimenting spanking myself, often sneaking down to the shed at the end of the garden and utilising whatever I could find for the purpose, usually ending up caning my own bare buttocks with a cane intended for supporting delphiniums.
As I discussed my intentions with the ‘Headmistress,’ my private philosophy was that when real punishment was meted out there was no choice for the recipient as to how hard it would be. After all, those who found themselves bent over for a caning in the Head’s study had little say regarding the severity of the punishment they would receive.
I really wanted to know what a proper spanking and caning would feel like, not just someone taking it easy on a youngster who admitted to little or no experience.
Yes, I was determined to feel the cane as it was meant to be. With coffee consumed I was then taken to the ‘study’ in the basement of the house, at which point I cannot deny that the butterflies in my stomach began doing acrobatics.
To facilitate role play I'd confessed to masturbating about girls I was familiar with. At this time, barely a year since I had actually left school, there were numerous girls from my schooldays still active in my mind, even a couple of the younger female teachers thrown in for good measure. All of them still played a part in fuelling my masturbatory fantasies time and time again.
Well away from home territory I used their real names, admitted to the fantasies I’d had for them, well, the fantasies I was prepared to divulge at least!
The ‘Headmistress’ seemed genuinely interested in me, apparently her staple custom was middle-aged and older men, usually business types and she openly admitted that having a handsome (her judgement) and much younger man with a firm, tight bottom, eminently preferable to the overweight men with unappealing bottoms that usually frequented her study.
With her mortarboard and gown donned, she certainly looked the part and I just knew I wasn’t going to get off lightly. I had booked and paid for an hour with this lady, almost exhausting my savings at this time, but with no further bookings that afternoon, she allowed me to stay for over twice the time at no extra cost.
By the end of my visit I had endured the ‘Headmistress’s hand to warm me up before progressing to a variety of implements; ruler, gym shoe, paddle, strap, to name but a few. The finale was of course, the cane, a variety of canes in fact, and my poor bottom suffered mercilessly.
With it impossible to estimate how many strokes I’d received, the ‘Headmistress’ eventually lowered the cane, concerned that further strokes may begin to draw blood.
I’d coped well, even the ‘Headmistress’ congratulated me on my stoicism as she massaged cream into my ravaged buttocks before deliciously working my cock with her hand to the point of release, but as I left her house and walked stiffly to my car parked some distance down the street, I began to question myself. At that moment in time I made the decision that I would never have anything to do with corporal punishment again.
I had truly discovered what it was like to be punished for real and was grateful for that, but as my buttocks throbbed and the pain of each stroke inflicted on them was so fresh in my mind, I decided that I never wanted to be in this position again. My return journey was uncomfortable to say the least and as I drove the sixty or so miles back home, I vowed that I would never put myself through anything like this again.
No, this wasn’t for me and now that I really knew the true agony of being on the receiving end of strict corporal punishment any desire to inflict it on others seemed to have also evaporated in one fell swoop!
Even my fantasies held no more appeal. The numerous attractive young ladies who had previously captured my thoughts and been mercilessly spanked and caned to my pleasure were owed an apology in my mind. Corporal punishment wasn’t fun, it wasn’t sexy, it was barbaric!
Nothing at this time would ever have made me believe that I would be back to visit the ‘Headmistress’ again and again over the following two years, baring my bottom for more of the same and actually growing to like it.
As Debbie remained in the corner, I took every opportunity to study her beautiful bottom. I knew that it would likely be a few weeks before I saw her again and although I would doubtless spank other bottoms in that time, it was hers that I wanted etched in my mind. Her bottom was undoubtedly the crème de la crème of bottoms for me at this time.
After moving the chair I had sat on for her spanking, I instructed Debbie to bend over the desk, a plump velvet cushion placed neatly beneath her belly as she leaned forward. The cushion caused Debbie’s bottom to rise delightfully and to form a wonderfully accessible target.
“I’m going to give you three lots of six strokes Debbie,” I informed her. “So maybe the next time you attend a party you’ll remember this caning and behave in a more appropriate way.”
Debbie turned her head towards me, “I’m sure I will Sir, I’ll never do anything like that again I promise, but I know that I deserve to be caned.”
I selected the first cane that I would use on her. It was a light, whippy cane with a crooked handle and although capable of inflicting a mighty sting it would provide a relatively tolerable start to her caning.
“Six strokes with this cane Debbie,” I informed her as I squared the cane to the centre of her gloriously reddened bottom. “Are you ready?”
Debbie tucked her hair behind her ears and then reached forward to clutch the far edge of the desk before responding, “Okay Sir, I’m ready.” There was an air of trepidation in her voice, perhaps only to be expected from someone about to receive eighteen strokes of the cane on their bare bottom.
I allowed myself a moment to savour the scene, the beautiful reddened buttocks, the sight of her vagina and its surrounding enchanted forest of pubic hair peering so provocatively between the tops of her shapely thighs. Yes, her bottom was indeed a perfect target for the cane!
I tested the flexible rattan through the air, it’s delicious swish as I did so causing Debbie to flinch, unsure whether she was about to feel the cane’s first bite upon her already challenged flesh.
After tapping the cane against her I drew it back, before delivering the first stroke squarely and firmly across the very buttocks that so captured my imagination. “Ouch, God, that stung,” her response.
Once more I squared the cane to its target and as it bit into Debbie’s flesh for the second time, she yelled, “OW-AH-OW.”
I recalled using this same cane a few weeks before and after administering ‘six of the best’ to the usually resilient recipient, I suggested, “I bet you hardly felt that.”
Her response, “You’re joking, that cane might be thin, but it really, really, bloody stings.”
As I continued to cane Debbie, I delighted in the sight of the narrow pink stripes that began to emerge on her cheeks and with only one stroke of this particular cane remaining she knew what to expect and without encouragement, squeezed the far edge of the desk ever more tightly as she braced herself for the hardest stroke yet.
I wasted little time in painting that final stripe across her mouth-watering bottom. As a deep intake of breath hissed through her teeth, she finally gave way to a cry of, “EEE-OW-OW-OW!” With permission given, she stood up and tended her wounds, attempting to rub away some of her anguish with her hands.
“So, do you still think it was worth sucking those cocks now?” I asked her. “I’m not so sure Sir,” she replied coyly.
I paused for a few moments to allow Debbie some respite, and before selecting the second cane I would be using, I ran my fingertips across the contours of her bottom delighting in the feel of the slender raised weals which now embossed it.
For the next six strokes I had chosen one of my favourite and perhaps, most used canes. A straight cane with a leather handle, medium thickness and undoubtedly more challenging than the first.
After ordering her to bend forward, I watched in readiness as she went through the process of tucking her hair behind her ears. For whatever reason, I always enjoyed seeing her do this.
As before, I tested the cane through the air and once more Debbie flinched. I decided to apply this cane swiftly, six strokes in quick succession and as I offered the cane to the centre of her bottom, I advised her of this.
Drawing the cane back, I brought it down to meet its target firmly and squarely, and as stroke followed stroke she contorted frantically as I varied my aim to spread the onslaught.
With barely enough time between each stroke for Debbie to catch her breath before the next searing bite cut into her flesh, her vocal responses were muffled and indistinguishable amidst her contortions, but as the final and hardest stroke with this cane landed with a resounding ‘thwack’ across the lower part of her buttocks she was more than able to make up for this, “OW-OW-OW… OH, AH, AH, AH…...OH FUCK, .... FUCK, FUCK…OH, Oh fuck,” she exuded in breathless fashion.
As Debbie rubbed herself, my eyes became focused on her well striped cheeks, those majestic buttocks that I had become so obsessed with since the very first time she had slipped down her panties and presented them to me bare.
Placing the cane on the desk I moved to stand behind her. I wanted to be close to that bottom, the bottom I had just caned and would soon cane again in order to complete her punishment. I felt compelled to scrutinise the fruits of my labour, satisfy my passion for the way nature had created this truly wonderful rear and how the cane had left its mark.
As I ran my fingertips over her contours enjoying the feel of the swollen ridges, “OOOH,” squealed Debbie as my touch reignited some of her discomfort. “Is your bottom very sore Debbie?” I enquired. “Yes, it’s really, really sore, it really does hurt,” she replied emphatically.
“So, what do you think about sucking those cocks now Debbie?” I just had to ask. “I wish I hadn’t done it Sir, my bottom hurts so much from the cane.”
I stepped back and allowed Debbie a few more moments to rub herself. No matter what happened, I intended the finale to this caning to take Debbie to a new limit and I had little doubt that this was what she wanted also.
“Okay Debbie, bend back over it’s time for your final six,” I informed her. “Oh, please Sir, I’ve learnt my lesson do I really have to have more with the cane, perhaps I could suck your cock to make up for my bad behaviour instead?”
I pondered my response, privately grinning as I did so, confident that Debbie was just adding drama to the role play. “Perhaps I should get on with the remainder of your caning and then get you to suck my cock,” I eventually responded.
Debbie hung her head. “Very well Sir, I suppose I deserve it,” she responded quietly.
Debbie once more went through the process of tucking her thick, auburn hair behind her ears before again stretching across the desk. As she did so, I was reminded of her earlier admission, “It takes something really special to get me properly aroused, normal stuff just doesn’t really do it for me.” Perhaps corporal punishment was proving to be that something ‘really special’, something that I imagined her likely vanilla marriage had not afforded her.
The cane I had selected for the final six strokes was heavier than the previous two, thicker and less flexible and I knew from using it on other female bottoms, it would doubtless present a true challenge to Debbie.
Clasping the cane close to its crook handle I offered it to her buttocks, again delighting in the view of my target whilst unable to avoid the thought of being sucked by this captivating woman when her caning was complete.
The previous cane strokes had left their mark and I was convinced that even if I added no further challenge to her bottom, very soon the angry weals she already displayed, would blossom into an array of colourful hues that would decorate her cheeks for a while to come.
As before, I tested the cane through the air and once more Debbie flinched. The sound of this heavier implement as it descended through the air, enough to confirm to her the anguish ahead.
“Okay Debbie, six more strokes and your caning is over,” I advised her. “Yes Sir,” she replied as she further fidgeted into position.
“This time I want you to count each stroke aloud after you’ve received it, is that clear?” I informed her. “Yes Sir, perfectly clear,” she replied nervously.
As I drew the cane back for the first stroke, Debbie pulled her shoulders down in anticipation of its bite and as it landed with a resounding ‘thwack’ across the centre of her bottom she thrust her head back wailing, “EEE-OW-OW-OW!” as she did so. Debbie contorted wildly before returning to position and regaining her composure. “One Sir,” she added, perhaps knowing that failure to do so would mean the stroke didn’t count.
Placing the cane a little higher on her buttocks, I focused on a gap between two of the earlier strokes she’d received. Drawing it back for the second stroke I brought it down briskly and as the cane met its target Debbie once more thrust back her head, simultaneously arching her spine, as she cried, “OW-AH-OW....OH……..BLOODY, BLOODYHELL.” As she fought to recompose, my eyes traversed her buttocks satisfying myself that the white line I had just painted with the cane was positioned exactly as intended. Barely had this line had time to flush deep red before Debbie responded with, “Two Sir,”
Drawing the cane back for the third time, I brought it down with a resounding ‘thwack’ across the lower part of her bottom just a fraction below an earlier weal. “EEE-OW-OW-WOW!” she wailed, “OH GOD, OH GOD.” Debbie again contorted her bottom wildly and tensed and untensed her knees in an attempt to quell her discomfort before returning to position.
“Three Sir,” she added, her voice strained and with her perhaps close to tears.
“Just three more strokes to go for sucking those cocks Debbie,” I informed her. Debbie steadied herself and nodded her head, “Okay, I’m ready for them,” she added.
For a moment I opted out of role play aware that I was taking Debbie beyond anything we had done before. “Do you want to stop?” I asked, adding, “I know this is much harder than you’ve had before.” Debbie shook her head, “No, no, my bum’s throbbing like hell, really burning too, but I really want to see this through.”
Placing my hand on her bottom I gently smoothed her cheeks. The feel of the warmth that radiated from them and the rugged texture of their surface leaving me in no doubt that if she didn’t know before, Debbie certainly now knew what a proper caning felt like. Allowing a finger to probe between her legs, the damp and sticky feel of her labia enough to tell me that perhaps, just perhaps Debbie was close to finding that ‘something really special’ that ‘normal stuff’ just didn’t afford her!
With my cock now stirring within my trousers, I returned to my role, wasting little time in delivering the fourth stroke to Debbie’s beckoning bottom, again trying to find a gap between the earlier strokes. As the cane once more bit into her she thrust herself upright, her auburn hair flailing wildly as she clasped her buttocks in her hands, “OW-WOW-WOW……..AH-OW....OH SHIT, FOUR SIR” she cried as she rocked from foot to foot.
“How does your bottom feel now Debbie?” I asked. “Oh, Oh, it feels like it’s been roasted,” she replied. “Okay Debbie, just two more then it’s all over,” I reminded her, confident she was already perfectly aware of this.
I watched Debbie as she once more tucked her hair behind her ears before returning to position. Why I found this action so arousing, I’m really not sure.
The penultimate stroke landed firmly onto the upper part of her buttocks, Debbie jolted back and again grasped her bottom with both hands. “OH, FUCK, .... FUCK, FUCK, sorry Sir, but my bum feels like it’s on fire,” she squealed before adding, “Five Sir”.
As Debbie bent back down for her final stroke, my eyes focused on the delightful crease where bottom and thigh merge, “One more stroke Debbie, what’s special about the last stroke?” I simply couldn’t resist teasing her. “I’d like to say it’s the softest Sir, but I know it’s going to be the hardest,” she replied with an air of trepidation, but perhaps also intermixed with an air of invitation.
My view of the side of Debbie’s face was enough to tell me that she had screwed up everything in anticipation and as I raised the cane for the final time and brought it down firmly a fraction above her crease, she all but climbed onto the desk. Debbie let out a piercing shriek which echoed around the room, simultaneously clutching her behind and rubbing herself wildly. “OH FUCK, BASTARD, HELL, THAT REALLY BLOODY HURT,” she yelled.
In normal circumstances I had never heard this normally genteel woman use any such expletives, but then again, these could not be considered normal circumstances. Perhaps in time, I would scold her for such outbursts, maybe add further strokes, but at this moment, this was not my purpose.
As I visually studied Debbie’s bottom it was clear to see that each cane stroke had left its print, angry raised weals adorned her cheeks and made a stimulating surface for my fingers to explore as I assisted in easing her anguish. I could only imagine the colourful patterns that would blossom to decorate these beautiful buttocks in a day or so. As I scrutinised her ravaged bottom, I so wanted its image etched in my mind for the future fantasies I would doubtless have about this glorious woman.
Debbie was undoubtedly close to tears, but somehow there was an elation within her that told me that she had enjoyed every agonising stroke. Although she would perhaps not do it all again this very minute, I had little doubt that she would be back for more of the same in the future.
With the cane discarded, I allowed Debbie a few precious moments to tend her wounds and regain her composure, my tingling cock eager for her oral attentions. As she turned to face me, I placed a finger under her chin and looked into her liquid blue eyes, “Well Debbie, now that you’ve had your punishment, do you think you’ll be so keen to go sucking the cocks of the young lads you’re in charge of at work?” Debbie shook her head, “No Sir, I’ll never, ever do it again, I promise.”
Reaching downwards, I offered a finger to her vagina, enjoying the feel of the coarseness of her bush as I did so. Debbie was wet, delightfully wet and there was little doubt that the cane had produced the desired effect.
Although I have always taken personal pride in controlling my emotions when administering corporal punishment, Debbie had challenged this. It was a challenge I had lost as the thin, cord-drawn casual trousers I was wearing concealed little of my arousal.
“Well, Debbie, just in case you ever forget the promise you have made and find yourself back here for another caning, I think you'd better show me exactly what it was you did to those two young men at your workplace,” I said.
Debbie nodded ashamedly, convincing me that in the few months since she had first presented herself in my study, the advancement in her role-playing skills was perhaps equal to her advancement in withstanding corporal punishment.
I watched intently and eagerly as Debbie slowly dropped to her knees and once more went through the process of tucking her hair behind her ears. I made no movement as she took hold of the cord around my waist and pulled open the simple bow that held it taut. As she coaxed my trousers and underpants down my legs, I was now delightfully at her mercy.
Wrapping her fingers around my cock, Debbie began to work me with her hand, whilst simultaneously licking and sucking the tip of my penis.
As I reached unparalleled hardness, she drew me into her mouth nibbling her way down my shaft, the feel of her teeth pressing against my skin, slightly hurting, yet blissfully pleasurable, as she did so. Clasping my buttocks tightly in her hands, she began to work her head back and forth and as I slid my fingers into her hair to ride with her motion, there could be little doubt that the cougar within Debbie was now fully awakened!
The end.
Marisol
- 01.08.2021
- 33
- 0
