In the first part he has received a tawsing on each hand and been told to ejaculate on her shoes and then clean up his mess, before being securely restrained over a punishment stool in their dining room with a chastity cage fitted to prevent him from becoming aroused during his punishment. He has been told he will receive 36 strokes of the smoked dragon cane followed by 36 of the extra heavy tawse to his thighs. The story resumes with Elspeth about to deliver the first stroke.

“You are about to receive thirty-six strokes of the dragon cane for self-abuse. There will be no leniency. It will hurt because it’s meant to.”

Then nothing. 

Total silence.

The seconds ticked by as Elspeth deliberately paused, ratcheting up the anticipation.  

You could have literally heard the proverbial pin drop.

If it wasn’t for the fact I knew she was still there I might have mistakenly thought she had left the room. 

Then I heard her breathe in and the almost imperceptible rustle of her clothing as she drew her arm back to deliver the first stroke.

Then it started.

The cane cut through the air with a sound like fabric being torn, before making impact with the centre of my backside with a loud crack that surely must have been audible outside.

For an instant, there wasn’t any pain.

Then, after what was probably only a fraction of a second, but felt much longer, a white-hot line of pain emanated outwards from where the stroke had landed.

I thought I knew what to expect. 

I thought I had prepared myself mentally for it, but my memories of previous canings were always softened by the fact I found submitting to corporal punishment from Elspeth so arousing.

Unconsciously, I screamed into the gag as the rational side of my brain exploded into an internal diatribe for putting myself into this position. 

My thoughts were broken by Elspeth impassively stating: “One.”

Then another long pause.

As my brain calmed from its initial panicked state, I tried to count the seconds to work out how long she was leaving between strokes. I guessed that I had taken at least fifteen to process the first stroke, so started there….

Sixteen thousand…

Seventeen thousand…

…Twenty-five thousand…

…Thirty-three thousand 

The sound of tearing fabric once more, the sound of the impact, then the pain. 

If anything, it was worse than the first stroke. How could I have put myself in the position?

How could I take just one more stroke, let alone another thirty-four?

In the second or two that followed my body involuntarily pulled at the restraints, but I was too firmly secured for me to achieve anything beyond clenching my fists and twisting my feet.

Elspeth’s only response to my attempts at escape was “Two.” 

I breathed in the intoxicating scent of her from the very wet gusset of her panties, and tried to prepare myself for the next stroke. 

If I hadn’t been gagged I would have been pleading, even shouting to her, to stop, that I was wrong and couldn’t take what we had agreed last night. 

But that was the very reason why I was gagged, because in order to get to that special place, I needed to get through this. Just as she needed the arousal she gained from disciplining me.

To anyone walking in on us that day it would have been hard to believe that in the early years of our marriage, we’d been a relatively vanilla couple. I’d always had fantasies about being disciplined by strict ladies, as while I’d never been spanked at home by my parents, I had witnessed the administration of corporal punishment once in my formative years which had planted a seed that had grown from curiosity into a need to experience it.

We’d met in our late twenties, both having had previous long-term relationships, but I’d never found the right moment to raise my desire, which was perhaps why they’d ultimately fizzled out, and I’d had to scratch the itch in secret myself through self-spanking. But even though it was different with Elspeth, and there was a deeper connection between us than I ever felt possible until I experienced it, it wasn’t until around a year into our marriage that I raised the subject. In the end, it wasn’t planned, we were enjoying some mutual touching and playing with toys and it just came out as a gasping request as I ejaculated.

Elspeth didn’t say anything at first, but once she had come down from her own orgasm and removed the rabbit vibrator that had been pushed deep inside her, she suggested we talk about it if I still wanted to. She gave me the space to do so without prompting, and when the time came when we were lying together naked a few days later, she listened encouragingly as I stutteringly told her what I wanted her to do to me and why. Over time we experimented, tentatively at first, as Elspeth was worried that she would hurt me, or damage me permanently in a way that would lead to the end of our marriage. It soon became clear to her that her concerns were unfounded, that to be hurt was exactly what I wanted, and as the worries fell away Elspeth grew both more confident and increasingly aroused while disciplining me. Afterwards, she would demand that I use my tongue to bring her to a noisy orgasm to thank her each time. Over time we experimented with different implements, but always kept the plimsoll, cane, and tawse at the centre of it, albeit increasing in severity resulting in us having accumulated quite a collection over the years.

By the sixth stroke, my body had begun to give up its involuntary attempts at escape, but the pain in my backside was unbearable, and I was sobbing with tears running onto my forehead, before gathering into large drips that fell the short distance to the floor. 

“Six.”

I heard the scrape of the soles of Elspeth’s gorgeous heels on the floor as she turned, then her walking across the wooden floor as he repositioned herself on my other side. 

As regular as clockwork the sound of tearing fabric followed thirty seconds after the last stroke. 

“Seven.”

My sobbing intensified as strokes eight and nine took the pain in my backside to another level.

By this point, Elspeth had worked her way down my backside, and next stroke landed on the crease where it met my thighs. The pain was unbelievable, and I screamed “stop” into the gag, but all that Elspeth could hear was an incoherent noise.

“Ten.”

I knew that I was now reaching the point where Elspeth would be trying to place strokes in between the raised wheals that would have already formed on my backside, and that the pain would only increase.

“Eleven.”

I was trying to control my breathing to prevent myself from hyperventilating.

“Twelve.”

Again, the sound of Elspeth’s heels on the floor as she repositioned herself. 

“Thirteen.”

I was now forcing myself to control my breathing.

Elspeth’s accuracy was, unusually for her, slightly off on the next stroke, and it landed partially on top of a previous one.

“Fourteen.”

As the pain from the stroke bloomed, I began to feel a sensation that I’d felt before in my groin as I got to that special place. A difficult-to-describe tingling of arousal that spread rapidly, almost like heat.

The next stroke landed, and in an instant, I was there. There was still pain, but it felt almost distant, something separate that I was both experiencing, and not experiencing, at the same time. 

“Fifteen.”

Unconsciously I began attempting to push my backside out to meet the cane. While I was restrained over the stool with little room for movement, Elspeth had previously told me that she could see the change in the muscles in my thighs when this happened, and spotted it immediately.

Knowing that I was now in that special place, she immediately increased the pace of the strokes, the next two landing just ten seconds apart before she quickly swapped sides again.

Over the next three minutes, Elspeth delivered a caning to remember, her years of experience in administering corporal punishment to my backside enabling her to deliver every stroke with exquisite severity. No part of my backside was left untouched by the cane, with strokes overlaying each other at this point, and by the time she concluded my punishment with two very deliberately placed strokes to the tops of my thighs I knew it would be mass of angry red wheals and purple bruises, that would make sitting unbearable for days.

Elspeth’s gorgeous legs came into my tear-blurred vision as she walked in front of me, heels booming on the floor, to place the cane on the dining table. I was still floating in subspace when, seconds later, she returned and I heard the sound of a zip, then a rustle of clothing as her skirt dropped to her feet. She kicked it away with her right shoe, then squatted down, the triangle of thick ginger hair between her legs parting to reveal her orchid-like labia glistening with arousal. Despite the pain in my backside, I felt my cock begin to swell in its cage, the ring pulling uncomfortably on my balls as it did, at the sight of her. A few seconds later she placed two fingers under my chin, tilting my head up so she could look into my eyes before very matter-of-factly stating, “Time for the tawse, you dirty little masturbator.”

I heard her footsteps on the floor as she walked back to the bag to retrieve the most severe implement that we owned, then as she returned to stand to my right. I felt its weight against my skin as she measured it across the top of my thigh, accompanied by the sound of the leather soles of her shoes scraping on the wooden floor as she slightly adjusted her position. 

Then the weight lifted away.  

“Thirty-six strokes of the special extra-heavy tawse.”

With that, out of my sight, Elspeth took a deep breath and lifted her arm so that the back of her hand rested on her shoulder, the tawse dangling down behind her. Then, after a brief pause, she brought her arm down as she exhaled, flicking her wrist as she did so in a well-practiced move, the tawse cutting through the air with a sound like a gust of wind before making contact with the back of my thighs about midway along the split section of its length with a loud crack. The remaining length of the tails then continued to accelerate, curling around my leg so that the tips bit deeply into the soft flesh of my inner thighs. As ever, Elspeth’s accuracy was immaculate, and the tawse had not only overlapped the lowermost cane stoke but the tips had also missed my balls by mere millimetres.

A minute, at most two, had passed since Elspeth had finished administering the cane, but in that time I had dropped out of that special place. I too had taken a deep breath to try to calm myself before what I knew would be an excruciating tawsing, and I let it out in a muffled scream through the dirty panties that I was still gagged with, that moved upward in pitch a fraction of a second later as the tails bit into the soft flesh of my inner thigh. My whole body shook as I again tried to free myself from the restraints, before my scream petered out to a hoarse, barely human, noise as I shook my head repeatedly trying to deal with the pain.

As soon as my futile attempt at escape had subsided Elspeth matter-of-factly stated, “One,” before raising the tawse to administer the second stroke.

While Elspeth’s disinterest in my response to the tawse may have seemed odd, it was based on her experience of using the tawse on me many times over the years. Our first tawse was a pretty pathetic affair as a disciplinary implement - we’d purchased it from a well know adult store but when it was first used it had quickly become clear that the thin leather and wide four-inch width made it pretty ineffective in delivering anything other than a short-lived sting. Our second came from a specialist tawse maker - a medium-weight tawse that we had had for around 15 years, and which was still very supple from my regular application of drubbing. Its weight makes it perfect for delivering punishments to the hands as it gives a good sting without any danger of lasting damage. The extra heavy tawse that we got a few years later stepped things up considerably, much thicker and heavier than the medium tawse it was excruciating when used on my hands and backside, as I had been reminded earlier in the day. Elspeth had used it on me more times than I could count, and I knew that when restrained I would have no choice but to accept the painful bite of the tails on my inner thighs as she got wetter and wetter as she used it on me.

However, what was being used on me now was our most recent purchase about twelve months ago, as we emerged from the pandemic and resumed our interest in corporal punishment, which we had to put on hold when the kids were at home twenty-four seven. Our special extra heavy tawse. As a previous very satisfied customer, we’d made an enquiry to the tawse maker about making an extra heavy tawse even more severe by weighting the tips with small weights, in doing so this had made them even more vicious to the point where we had agreed that it would never be used on my hands for fear of causing unintended injury. It was this tawse that was now being used on my thighs - not for the first time, but never for this many strokes before. By the third stroke, my responses were less dramatic, and by the fifth, I was back in subspace, the muscles in my body pushing backwards almost inviting the next kiss from its vicious tales.

After six strokes Elspeth paused briefly whilst swapping sides, the leather of her soles once again scraping on the wooden floor as she lined the tawse up again, before unleashing six more perfect strokes to set my left thigh on fire. My vision was once again completely blurred, and my body covered in sweat from my attempts to escape.

Two more swaps of sides left me with twelve more strokes to receive before my punishment would be over, and it would be time to show Elspeth my gratitude. But she had no intention of making them easy for me to take. Moving to the front of the stool she stood astride my head, her gorgeous nylon-clad calves and shoes filling my blurred vision and the scent of her arousal unmistakable. She immediately began completing the final twelve strokes, varying the length so that the tips of the tawse worked their way up my thighs, alternating right to left placing stokes perpendicular to those that she previously applied, with the ninth and tenth strokes biting into a cane stroke on my sit-spot causing my head to lift and make contact with her thighs as I screamed involuntarily.

But nothing had prepared me for the final two, delivered with barely a second between them, straight down my back, the middle of the tawse making contact with my already very sore right cheek before the tips curled around and caught my balls presented perfectly by the chastity cage. The left followed so quickly that the pain had barely begun to register before it knocked the wind from me, otherwise, I would have been screaming into the gag. My whole body convulsed and there was a loud bang as I caused the stool to walk backwards several inches. But my punishment was over - at least for now - and I was a broken, bedraggled mess, hanging limply over the stool. Exactly how I had asked Elspeth to make me as I had used my fingers to help her cum last night.

There was total silence in the room other than Elspeth’s heavy breathing from her exertions. After what seemed like an age, but was probably no more than thirty seconds, she stepped away, her heels again booming on the floor as she put the tawse on the table, before returning to stand by my head. Squatting down, so that her thighs once again opened to reveal her very wet pussy, she released my hands before she stepped back and spoke.

“Time for you to thank your strict headmistress for taking the time to punish you for being such a filthy masturbator.”

Again, there was the sound of her shoes on the floor, followed by her unfurling the thick camping mat I had brought down earlier onto the floor in front of me. Next, she removed her dirty panties from my face and mouth, before lying on the mat with her gorgeous bum against the legs of the stool and her legs draped over my shoulders.

“I expect you to show your thanks with your tongue” was her simple instruction, and I gasped involuntarily as she immediately dug her heels into my back, pulling her very hairy pussy hard against my face, and causing my mouth to open as she did so.

I have always loved the taste of Elspeth’s pussy, and pleasuring it with my tongue has always been something that I have enjoyed almost as much as her, and I could feel my cock harden in its cage despite the pain in my balls from their recent kiss from the tawse, as the deliciously pungent taste of her arousal filled my mouth.

I started to begin slowly, savouring the taste of her wetness, but Elspeth had other ideas shouting, “Get on with it, boy, I need to cum NOW!”

Mindful that I remained restrained with my bottom still on fire from my punishment, I was very keen not to incur Elspeth’s displeasure any further, and therefore put my eager tongue to work on her swollen clit in a way that I knew from years of pleasuring her would bring her to orgasm quickly. Within a couple of minutes, I felt her tense, then dig her heels even more painfully into my back, as she pulled herself against me so hard that I struggled to breathe. She screamed at me not to stop, convulsed, and spurted her cum into my open mouth. As her orgasm subsided and I gasped for breath, she commanded, “Again, make me cum again, you disgusting cum eater.”

I once again put my eager tongue to work, quickly making sure I had cleaned up her tasty cum, and then going to work on her clit again. Her orgasm took longer to arrive on this occasion, and out of my vision she had unbuttoned her blouse and was playing with her hard nipples through her bra, flinging her head back and opening her mouth to let out a loud, incoherent, almost inhuman sound as it consumed her. I had never experienced her cumming so hard, gripping my head and digging her heels into my back harder than I ever thought possible and ejaculating her cum into my mouth like a fountain as she violently thrust herself against my face, before clamping my head tightly between her thighs, almost causing me to pass out as she did. This time it took much longer for her orgasm to subside, and as I felt her slowly relax, I was aware that she was as breathless as I was. This time, her next command was spoken softly, almost as a request. “Again, and this time you can take your time.” 

This time I began by tracing her gorgeous orchid-like lips with my tongue, if I had been knelt between her legs I would have told her how beautiful her pussy was, but not wishing to pause, I was completely focused on her pleasure. After exploring her lips, I gradually pushed my tongue as deep inside her as I could, thrusting it in and out in a fucking motion, before with a loud groan she shifted her position slightly, indicating she wanted me to give her clit some further attention. As I sucked her swollen button, I began tracing my tongue over it, probing under the hood with the tip and delighting in sounds I could hear her emitting as I did. As I knew she enjoyed, I started drawing each letter of the alphabet with my tongue on her clit and had almost made it through the fourth repetition when her orgasm arrived. This time it was far less violent, and as it subsided, she let out a deep groan of satisfaction.

We were both still for a short while, me still restrained from the waist down and dressed in an adult schoolgirl uniform complete with silicone breast forms, and Elspeth naked but for her gorgeous heels, stockings, open blouse, and bra. Her previously perfect hair was now dishevelled and the thick greying red hair around her pussy was matted with a mixture of her cum and my spittle.

After a few minutes she got up and I heard the rustling of the toy bag as she searched for something before she returned. Spreading her legs in front of me she made me watch as she inserted her favourite ten-inch dildo into her pussy, humiliatingly commenting that “your tiny cock will never satisfy me in the way this dildo can,” before she plunged it in to the hilt and proceeded to fuck herself with it noisily. Next, she rolled over and got up on her knees, the dildo remaining deep inside her, pushing her ass back into my face before spreading her cheeks.

“I’ve given your backside plenty of attention, so it’s about time you gave mine some.”

I had always absolutely loved, Elspeth’s voluptuous ass, and the way the ginger hair from her pussy continued up in between her cheeks. As she pushed herself back forcefully into my face, I began by licking around her asshole, loving the musky taste of her bum, before beginning to push my tongue against it to gain entry. As I did so Elspeth pushed back even harder against my face while simultaneously reaching between her legs to fuck herself with the dildo.

“Tongue fuck my ass you dirty little slut.”

With the help of Elspeth, my tongue penetrated her asshole, and I proceeded to use it to fuck her ass as she instructed, loving the taste and feeling of submission of doing so. All too quickly for me, she orgasmed as she noisily fucked herself with the dildo, and pulled away leaving me wanting more. 

Rising, I heard Elspeth move behind me to the bag and then further, prolonged, rustling and the sound of her heels on the floor. I heard a deep, guttural, groan as she removed the dildo from her pussy, then further rustling and a further small groan. When she returned, she was completely naked but for her shoes, stockings and an eight-inch strap-on dildo that was now fastened around her waist. As she reached down to lift my chin I was transfixed by her large breasts and hard nipples. Releasing my chin, Elspeth shifted her position slightly, so that the tip of the dildo was close to my face before speaking. 

“I suggest you get sucking if you want my cock to be lubricated before I fuck you like the wanton slut we both know you are.”

I immediately opened my mouth wide to take the girth of the dildo, sucking noisily as I knew Elspeth liked me to, coating it with my spit as she began to thrust into my mouth while playing with her nipples. As she slowly withdrew I made sure to coat the tip of the dildo as generously as I could, as I prepared myself mentally to take what I knew from past experience would likely be a very enthusiastic fucking.

Moving behind me quickly, I felt her remove the plug and quickly place it on the wooden floor, then almost immediate pressure against my asshole as Elspeth pressed the tip of the dildo against it. She gradually increased the pressure, and I let out a groan of a mixture of both pleasure and discomfort as I consciously tried to relax my sphincter so she could enter me. She slowly pushed the dildo deeper and deeper inside me until I could feel her crotch pressing painfully against my very sore backside. After a brief pause, she slowly withdrew until only the tip remained inside me, then reached down to turn on the bullet vibrator that was inserted into the harness against her clit, before slowly inserting it again.

“Don’t you even think about cumming like the filthy little slut that we both know you are, this is for my pleasure only!”

“I will try not to, Headmistress.” 

“You will do as you are instructed, or you will feel the cane again,” came the response from Elspeth.

As she slowly increased the pace I could feel the dildo stimulating my prostate as Elspeth fucked me hard, tormenting my very sore backside with every thrust. Feeling her orgasm approaching she reached forward, using the waist strap that was securing me to the stool for purchase, as she reamed me faster and faster. Despite my best efforts to avoid it from happening, I felt myself involuntarily spurt cum inside my cage without experiencing an orgasm. But Elspeth hadn’t finished with me yet, and continued to grip the strap fucking me harder and faster than she had ever done before to a second voluminous ejaculation, then carried on until her orgasm arrived and she fell forward impaling me deeply for a final time.

Slowly withdrawing from me, Elspeth removed the strap-on and reinserted the plug before moving in front of me, with a stern look upon her beautiful face as she once again assumed the persona of a strict Headmistress, retrieving the dragon cane that had already delivered so much pain to my backside from the table.

“What did I tell you?”

“Not to allow myself to orgasm, Headmistress.”

“And what did you do? Twice, if I am not mistaken?”

“I ejaculated twice, Headmistress, but I didn’t have an orgasm. I’m sorry, I didn’t mean to, I just couldn’t help it.”

“Don’t you dare lie to me! Of course, you had an orgasm and of course, you could help it! Do you have no self-control?” Elspeth asked rhetorically.

So, that’s one set for each orgasm, and one for failing to pleasure me as I required. Perhaps this will teach you a little more obedience and self-control in the future.” 

“Yes Headmistress, thank you, Headmistress.”

Elspeth re-secured my wrists to the stool then moved behind me with the familiar sound of her heavy heels on the wooden floor, then a scraping sound as she positioned herself to deliver the caning. Still very aroused and on the cusp of re-entering submissive heaven due to my lack of orgasm, I almost couldn’t believe what came out of my mouth next.

“Headmistress?” 

“Yes, boy, have you got something to say? I hope you remember that failing to accept your punishment will lead to extras.”

“I think I deserve two sets for each thing I have done wrong.”

“Very well, prepare yourself, this will be a very unpleasant experience for one of us!”

There was no gag to muffle my cries during the initial strokes, or slow pace to get me into subspace this time. Elspeth knew by my request and lack of orgasm that I was already floating on the edge, and she also knew exactly how to respond. By the third stroke, I was there, visibly pushing back, inviting my already heavily whealed and bruised backside and thighs to receive further punishment. By the ninth I was an utterly broken, sobbing, mess; and when she broke the skin on a wheal on the twenty-third Elspeth knew that she had taken me to a place like she had never done before. But she continued, as I needed her to, to deliver a full thirty-six strokes with impeccable accuracy in a little less than two minutes. The pain was indescribable, but so was the pleasure, and I felt almost disappointed when she stopped.

The cane clattered as Elspeth dropped it onto the floor, then she quickly tended to the broken skin with our first-aid kit before releasing me from the restraints. I remained there for a few minutes, broken, and sobbing across the stool before I somewhat gingerly removed myself, tottering slightly on the kitten heels of my Mary-Jane’s. Every part of my body hurt from the neck downwards, but at the same time, I was in heaven. Kneeling behind the stool, my backside was on fire as I proceeded to lick every drop of the cum I had deposited on the stool from where it had dribbled on to the leg, and then a small pool that had formed on the floor before Elspeth had time to instruct me to. Glancing up at her as I did so, she smiled approvingly.

“Once you have finished, I want you stood in the corner for thirty minutes, hands on your head and disciplined backside on show to the world.”

Without waiting for a response, Elspeth left the room and ascended the stairs. Once I had finished cleaning up my cum, I picked up the cane and wiped the blood - my blood - from it with a tissue before kissing it and placing it on the table. I then set the timer on the smart speaker and assumed the position she had instructed in the corner. From upstairs I heard the unmistakable sounds of Elspeth starting to pleasure her own body.

The corner time was uncomfortable, yet also a turn-on for me as I was almost in a dream state, not quite believing what had happened so far that day. While I loved the feeling of being dressed in the way I was, I had strained pretty much every muscle from my neck downwards, either from resisting or submitting to the punishment, and this made standing in even kitten heels difficult. But as I stood at the wall, the weight of the silicone breast forms in the long-line bra pulling against my back, and glancing down at my shiny patent heels I was in heaven. My backside and thighs were on fire, but it was exactly what I had needed. Despite the pain and discomfort, I started to become aroused, the small cage pulling against my balls with only a tiny amount of hardening of my cock, but this only served to make me more aroused, the pain driving me to become harder and harder.

It seemed strange to me afterwards, but the thirty minutes seemed to pass in seconds as I spent so much of it lost in my highly aroused thoughts. I cancelled the timer as soon as it went off, and as I left the room, I couldn’t help but notice my tear-stained face in the hall mirror.

The climb up the stairs was painful, and I had to use the banister to stabilise myself a couple of times.  On entering the bedroom, I was treated to the glorious view of Elspeth sat on the bed with her legs apart waiting for my tongue to bring her to one final, sensual, orgasm. Wordlessly, I knelt between her legs, planting delicate kisses against the soft pale flesh of her inner thighs, then around her beautiful hairy pussy before I slowly and gently pleasured her to her orgasm. As it washed over her, she lay back on the bed, pinching her nipples as she let out a deep, lingering, “Yyyyeeeeesssssss.”

Rocking back on my knees, I looked into her beautiful eyes as she sat up again.

“Would you like a reward for being a good boy and giving me such a lovely orgasm?”

“Yes, please, Headmistress.”

With that, I saw that Elspeth had the key to the chastity cage in her hand, with my cock becoming fully erect almost as soon as she unlocked it. She then pushed the cage into my mouth so I could clean it with my tongue.

“You may ejaculate on my shoes.” 

Elspeth placed her feet together as I shuffled backwards, lifting my skirt with left hand as I quickly began pleasuring my rock-hard cock with my right, my orgasm rapidly consuming every atom of my body, my eyes rolled in my head, as I made a sound that Elspeth would later tell me she had never heard me make before. As I came to my senses, I removed the cage from my mouth and looked down to see that, despite the power of my orgasm, my almost empty balls had only managed to deliver a single pearl-like blob of cum to the toe of the left shoe. I quickly leant forward and removed it with my tongue, then sucked the remaining cum from the broguing. 

Breaking out of character Elspeth giggled as she remarked that at least I wouldn’t be cleaning cum stains out of the carpet, before asking if I was sure I wanted to receive a slippering before bedtime.

“Yes, Headmistress,” was my immediate reply.

“Then I shall expect you bent over the arm of the sofa plugged and in your uniform at 10 pm tonight for twenty-four strokes of the slipper, which will double every night for the next week. I can assure you that you will not have dry eyes by the time I have finished. You will also remain plugged and in your uniform until 3 pm,” responded Elspeth, briefly resuming her character.

I cautiously climbed onto the bed, lying on my front, feeling the breast forms against my chest, knowing I would not be sitting comfortably for at least the next week, and it would likely be weeks before my bottom would be ready for another caning. Elspeth pulled my skirt back to uncover my backside, then picked up a jar of ointment and began to gently apply it to my very sore skin. As she did so, she whispered, “Your cock isn’t too small, but you’re so fucking good with your tongue I wouldn’t care if it was,” into my ear.