The dining room of our suburban semi on a sprawling modern housing estate was dark, with the curtains closed despite it only being mid-morning on a bright October Friday.

I’d taken the day off work for what I was going to experience at the hands of my fifty-one-year-old wife. I wanted it. I craved it with an almost all-consuming need, even more than Elspeth wanted to do it to me. But that didn’t mean I wasn’t nervous, especially with how much I had struggled to take it to begin with last time. But on that occasion, she’d given me no choice once I’d committed myself to it by consenting to her restraining me, just as we had agreed and she had done for less severe discipline many times before, and I was thankful that she had neither given me the opportunity to get out of it or go easy on me despite my initial struggles.

I heard the sound of her heavy heels on the wooden floor as she re-entered the dining room. We’d folded up the normally fully extended table to its smallest size and pushed it into the corner, with the chairs moved to the edge of the room. This gave us plenty of room to set up the collapsible spanking stool that we kept hidden under our bed as soon as we returned from dropping the kids off at school. I’d also brought down the bag of implements and toys that we also kept under our bed, along with a thick foam camping mat from the top of the wardrobe and the long smoked dragon cane that was normally hidden behind my shirts inside it.

On completing the set-up we had a cup of coffee together as equals we were in our usual day-to-day lives, before hearing the neighbours leave at about 9:15. This day had been chosen because they had asked us to keep an eye on their house while they had a long weekend away, so we knew there was going to be no danger of them hearing what was going on in our dining room through the party wall. Elspeth gave it about a minute before going to the window to double-check. The kids would need to be picked up from school at 3:15, so give or take the short time it would take for one of us to walk to the school while the other put everything away, we had the best part of six hours for what Elspeth had planned for me.

“They’re gone. Are you still sure you want to do this?”

“Yes, more than anything Elspeth. I don’t just want it, I need it. I’ve needed it for weeks, and before Jon and Louise said about keeping an eye on their house.”

“Good, I know I haven’t let you cum for over a month, but I’m so fucking turned on thinking about what I’m going to do to you that I was dreading you changing your mind. My knickers are already soaked at the prospect, so I hope you enjoy it when you smell them shortly. Let’s finish our coffee then go and get changed.”

I finished my coffee before Elspeth, and she fixed her eyes on me with a stern look before speaking.

“Are you ready to report to your headmistress for punishment, you naughty, disgusting, boy?”

“Yes, Miss Elspeth.”

“Good, now go and get changed into your schoolgirl uniform and wait for me against that wall with your legs spread, the toes of your shoes touching the skirting board, your hands on your head, and holding this coin against the wall with your nose, and woe-betide your backside if you drop it,” replied Elspeth sternly as she pointed through the open door of the living room to the corner of the dining room where she wanted me to stand, sliding a two-pence piece to me as she did so.

My mind was racing. Previously I’d been dressed in an old-fashioned schoolboy uniform for discipline from Elspeth. However, after confessing as I was cumming during a lengthy tease and denial session a couple of months ago that I found the idea of being told to dress as a schoolgirl both humiliating and a turn-on, Elspeth had been very eager for me to do so, and we’d assembled our idea of a uniform over the intervening weeks. Well, I say us, it was mostly Elspeth - and she had let out a mischievous giggle more than once while choosing it.

We climbed the stairs, Elspeth first, her gorgeous voluptuous bottom making me hard as I followed her. She’s a little bit older than me, but God she is stunning in every way, and I had always felt proud to be her husband even before we discovered our mutual enjoyment of me submitting to her sexually, and of her administering corporal punishment.

I went into the spare room where my uniform and a teardrop-shaped stainless-steel butt plug had already been laid out by Elspeth while I assembled the stool, stripping my jeans, t-shirt, and underwear off before folding them up. My cock was rock hard, and I could see a drop of pre-cum forming on the tip as I briefly glanced at myself in the mirror before beginning to get dressed. I began by kneeling on the bed to insert the plug into my ass, warming it in my hands before lubing both it and my hole with my fingers. A gasp escaped my lips as it stretched me before I felt the relief of the most bulbous part passing, and my muscles gripping the stem. I used some tissue to remove a small amount of excess lube from around the base of the stem and my fingers, before washing my hands in the ensuite and beginning to get dressed.

I first pulled on the tight pair of maroon regulation gym knickers that instantly restrained my cock, a dark damp patch spreading from where my pre-cum made contact with the fabric. Next, I pulled on the plain white longline bra that Elspeth had insisted we include and inserted the C-cup silicone breast forms, followed by a white blouse, and dark grey box pleated gym slip that I pulled over my head. Next, I sat on the bed and put on a pair of white lacy knee-high socks and a pair of patent black Mary-Jane shoes with a one-inch Luigi-style heel. I finally completed my transformation by fitting a blond wig with long pleats and bunches. I personally thought the wig was too much, but Elspeth had thought it would make what I was going to do next feel all the more humiliating.

And as ever, she was right.

After straightening my uniform up in the mirror, I took a deep breath to compose myself before cautiously descending the stairs and nervously entering the dining room, passing the spanking stool - at present hidden from external view - to stand against the wall. As I did so I moved my legs apart as instructed, and slid the coin into place holding it against the wall with my nose, in full view of anyone passing who looked in the window. Our house is set back from the road with a parking space in front of the garage and a similar length area of grass in front of the bay window of the dining room which meant that on a bright day outside with the lights off inside, it was highly unlikely that anyone would see me where I was at the back of the room.

However, I felt very much on show to the world in my uniform for the more than forty-five minutes that Elspeth made me wait, my arms aching from holding them above my head and the weight of the breast forms feeling surprisingly heavy in the bra as the time passed. I knew not to move out of the position Elspeth had prescribed as she would be checking on the Blink security camera that was situated on the opposite side of the room from where I stood. I also knew that she would have heard the two occasions that I accidentally let the coin drop from the sound of it noisily hitting the wooden floor.

After what seemed like an eternity I heard our bedroom door open and Elspeth descend the stairs, then her heels on the wooden floor of the dining room, followed by the sound of the curtains being drawn and finally the sharp click of the light switch. The first part of my punishment was over, but I knew that what was to come would test my limits.

“Turn around, boy.” Her Glaswegian accent, though softened from over thirty years of living in South West England, had a tone to it that always sounded authoritative.

I turned around to see Elspeth dressed as my fantasy headmistress as she had been numerous times before, but it still made me open my mouth in a silent gasp at the sight of her. She smiled a knowing smile at my involuntary reaction.

Elspeth was dressed in a tweed skirt that clung to her wide hips at her waist with a matching jacket that barely contained her ample chest and a white blouse underneath. She had put her greying red hair into a bun and had included a pair of reading glasses on her nose for effect. She was wearing the shoes that she knew turned me on most - a pair of brown ladies’ brogues with a two-inch wood effect cone heel and dark leather soles - with black seamed stockings on her gorgeous legs. She looked amazing.

“So boy, I have received a note from Matron that you were caught erect, and in the act of self-abuse last night. Is that correct?” This was a background story we often used for why I needed to be punished. Last time Elspeth had played Matron the night before, complete with a navy-blue nurse’s uniform that she looked equally stunning in, catching me in the act. Then giving me an unforgettably long slippering with a heavy rubber-soled plimsoll while I was bent over the arm of the sofa in my schoolboy uniform. But the kids had been restless last night, and I’d unfortunately gone unspanked for a few days.

“Yes, Miss Elspeth. Although I was only adjusting myself as I know that self-abuse is a disgusting habit. I did have an erection, but that wasn’t from touching myself.”

“Do you really think me naive enough to believe that?” She didn’t wait for a response before continuing. “Regardless of your poor attempt at an excuse you are going to be punished, and punished hard, as this isn’t the first time you have been caught. Is it?”

“No, Miss Elspeth,” I responded submissively thinking about how well she played the part of the stern headmistress despite never having worked in a school. We both knew that doing so turned her on as much as it did me.

“Nor the second, or the third. In fact, I have lost count of the number of times you have been punished by Matron and myself for your disgusting habit. But you can, and will, be beaten until you learn some self-control. Is that understood, boy?”

“Yes, Miss Elspeth.”

“How many times did the coin drop?”

“Twice, Miss Elspeth.”

“Well, at least you were honest about that. So that’s two weeks of daily slipperings from Matron with her heaviest plimsoll before bedtime, starting from tonight, in addition to any other punishments you have earned.”

“Thank you, Miss Elspeth.”

“Good, I’m glad you have manners enough to express your gratitude to us for taking the time to correct you, although you will have plenty of time to do so in a more intimate way later. Now lift up the front of your skirt and tuck the hem into the waistband of your underwear. I want to check your knickers.”

I complied immediately, knowing that she would see how hard I was from her chastisement as well as the damp patch made by my pre-cum.

“You filthy-minded, disgusting, boy,” Elspeth scolded. “You were told to wear that uniform as punishment, but you seem to be aroused by it. Have you got anything to say for yourself?”

“No, Miss Elspeth. I’m sorry, Miss Elspeth.”

“You are not sorry at all, otherwise you would have learnt some self-control long before now. Your punishment was due to be eighteen strokes of the smoked dragon cane on your backside followed by eighteen strokes of the extra heavy tawse on the backs of your thighs, plus any extras you might earn during your punishment. It has now risen to twenty-four of each as a result of your lack of self-control.”

“Yes, Miss Elspeth. Thank you, Miss Elspeth.”

“Good, I’m glad you understand. Tell me, boy, honestly, when was the last time you ejaculated?”

We both knew the answer, but the stern way in which she asked it almost made me cum there and then.

“Just over a month ago, Miss, at the beginning of September.”

“So, I would assume that you have very full balls right now?” As she asked Elspeth reached down and gripped my balls through the fabric of my knickers, digging her fingernails into them as she did so.

“Yes, Miss Elspeth,” I gasped as she released my balls.

“Good, good. Well, as I have already indicated, we are going to try doing something a little different today to see if we can cure you of your desire to self-abuse, as your previous punishments do not appear to have acted as a sufficient deterrent.”

“Yes, Miss Elspeth. I deserve it, Miss Elspeth.”

“I’m glad you understand that punishment is the only way to cure you of your self-abuse.” We both knew the opposite was true, but it was all part of Elspeth’s act.

Elspeth turned away from me for a moment to retrieve a medium-weight 24-inch Lochgelly Tawse from the bag.

“But before we get to that let me warm your hands a little with my tawse. Six on each. Right hand first. Present it now!” The tawse was her favourite implement to use on me, having grown up in a period when it was frequently used in the schools that she attended.

I held my right hand out, supporting it with my left, exactly as I knew I needed to from past experiences too numerous to count. Elspeth measured the tawse against my hand, taking a small step back as she did so to line it up with my palm before drawing the dark leather implement back over her shoulder.

“If you move your hand the stroke will not count, and you will receive extras. Count them and thank me after each one.”

With that, she flicked her arm in a surprisingly small motion to bring the tawse down on the palm of my hand. While I knew what to expect it nevertheless felt like someone has put an ice-cold poker on my hand, and I struggled to keep it in place.

“One, thank you, Miss Elspeth, please, may I have another?”

The second stroke landed, and I repeated my thanks, followed by the third and fourth. On the fifth stroke, I struggled to keep my hand in place, and it dipped by a few inches at the moment after the stroke landed.

As soon as I had thanked her Elspeth matter-of-factly added, “Two extra strokes for failing to comply with my instructions.”

The fifth stroke was repeated, followed by the sixth, and I managed to keep my hands in place before thanking her for it.

Knowing I was due two more for my lack of self-control I kept my hands raised, awaiting the next stroke. But instead of delivering it Elspeth went to the bag and returned holding our extra heavy Lochgelly Tawse, before measuring it against my hand and delivering an excruciatingly hard stroke. I somehow kept my hand in place and managed to thank her despite the pain. The final, if anything even more vicious stroke, followed quickly before Elspeth instructed me to swap hands as she swapped back to the medium tawse leaving the extra heavy out for me to see. Fortunately, I managed to keep my hands in place this time and didn’t earn any further extras.

Putting the medium tawse back into the bag I felt my cock, which had softened during the tawsing, harden instantly at the sight of Elspeth bending over as she did so, with her skirt tightening around her gorgeous bum - the seams of stockings perfectly aligned with the stitching at the back of her sexy heels.

As she turned back towards me it would have been impossible for her not to see how aroused I was.

“Hmm, I can see I am going to have to beat you severely today, boy!”

My cock twitched and hardened even more in response.

“So, your penis-” Elspeth almost spat the word- “responds to me telling you I’m going to beat you? You have no self-control. If it wasn’t for Matron and myself you would be playing with yourself constantly!  I bet you would like to play with yourself now. I think you are so excited that if I told you to, you would get on your knees and make a disgusting mess all over my shoes."

I suddenly found my mouth so dry at the thought of submitting to doing this for her that I couldn't speak, but my cock betrayed me by hardening even further. She moved closer before adding, "And would you then lick up your disgusting mess if I told you to? Would you? I think you would. Imagine the humiliation."

Pausing, she reached down and gripped my cock through my knickers before continuing: "Imagine what it will then feel like to receive a real caning without this helping you to get through it. Do you want that?"

The words came out of my mouth almost involuntarily, "Yes Miss."

"Then do it. Remove your knickers, get on your knees, and cover my shoes in your disgusting mess. NOW!"

She moved a dining chair into the centre of the room and sat on it, as I quickly got to my knees in front of her, before grasping my now rock-hard cock in my hand and thinking about being disciplined by my strict Headmistress. The pain in my hand from the tawsing made me more aroused if anything, and I barely lasted a minute before I made a guttural groan of pleasure as I experienced an intense orgasm, enhanced by the plug in my backside, and splattered ropes of cum over the toes of her very sexy shoes.

I paused for a second, repulsed in the moment at the idea of cleaning the cum that was now at risk of dribbling off Elspeth’s shoes onto the polished wood of the floor.  Suddenly I felt her hand on the back of my head, grasping my hair, pushing my head down, forcing me to submit.  As my face approach the cum covered toe of her shoe I stuck out my tongue and proceeded to clean it first from her left and then her right shoe, smelling the leather, feeling the pattern of the brogue with my tongue as I dutifully sought out every last bit of cum, all the while loving the feeling of submission now that she had helped me get over my hesitation. 

When I thought I had finished I knelt up straight and into her eyes. Looking for acknowledgment that I had fulfilled her instructions, however, the only response I received was, "You missed a bit."

Glancing down, I realised I had missed two spots on the floor where a small amount had dribbled off each shoe, but before I could lean forward to clean it up she first ground her left shoe into the spot beside it transferring my cum from the floor to the sole of her shoe, before rocking it back on to the heel, exposing scuffed tan soles, and saying, "Now clean it up.”

I proceeded to clean the sole of her shoe with my tongue, the bunches on my wig brushing the floor, although they had only ever been worn around the house they felt gritty on my tongue and dried my mouth. My tongue moved from the smooth outer edges to the slightly scuffed floral patterned area, which I traced with my tongue.  She lifted her foot wordlessly and I took the heel into my mouth, sucking at it as I caressed the base of it as I cleaned it with the tip of my tongue.  When I had finished I knelt upright again, and she proceeded to grind her other shoe into the second spot of cum.  She rocked her foot back wordlessly and I leant forward to clean her other sole then heel.

When I had finished I knelt back straight again, looking up at Elspeth.

“I’m going to add a set of six strokes for each drop of your disgusting mess that you failed to clean up without my prompting. Now move the stool into the centre of the room and bend over it for me to restrain you.” As she was speaking, she stood and moved the chair she had been sitting on back to the side of the room.

As she did so she commented, “Maybe I should invite some other women around to watch one day.” I didn’t answer, she knew I had fantasised about the idea, but not that it was her mother that I had most often thought about watching and joining in with my discipline.

I did as Elspeth instructed and bent over the stool, thankful that she had chosen a bra that held the breast forms securely in place as my wig fell off as I did so, with Elspeth picking it up and putting it into the toy bag. We had agreed on me receiving at least 36 stokes when we had talked in bed last night, Elspeth using a toy on herself as we did, as while the last time we had done this we had agreed 24 strokes, it had taken me almost half of them to reach that special place where you never want the spanking to stop. I had therefore asked Elspeth to increase the strokes this time but loved the way that she had got to that total by adding sets. Given that she found caning and tawsing me hugely erotic herself, she had no objection to doing so - her only worry was whether she could hold off the massive orgasm that she always experienced from disciplining me for long enough to deliver them in full.

Elspeth began by fitting leather cuffs to each ankle, which she then padlocked to a ring attached to the bottom of each leg of the stool. Then, pulling my legs as far apart as the restraints would permit, added a spreader bar between them. Next, she attached similar cuffs to each wrist, padlocking them in place, before tightening a wide leather belt attached to the underside of the seat of the stool over my back. Lastly, I felt her gripping my balls, but before I could begin to get hard from her touch, I felt the cold stainless steel of a chastity cage being fitted, then heard the click of the lock engaging. I was now completely at her mercy, but instead of commencing my caning Elspeth left the room, switching the light off, telling me to contemplate my fate. I heard her climb the stairs followed quickly by the unmistakable sounds of her cumming using a toy, once, twice then for a third time.

The dining room of our suburban semi on a sprawling modern housing estate was dark, with the curtains closed despite it only being mid-morning on a bright October day. I heard the sound of her heavy heels on the wooden floor as she re-entered the dining room.

Standing in front of me, she bent down so that I could see her face, before unceremoniously unfurling a pair of very soiled and skid-marked white knickers, slipping briefly out of her Headmistress persona to comment, “I’ve been wearing these at night for the last week so you should find them very pungent,” before pushing them into my mouth with the gusset on my tongue to gag me. She was right, the taste was very strong, but while some would be repulsed by it, I loved the taste of her on them and immediately sucked at the material.

Next, she tied a short length of soft rope around the back of my head to hold the gag in place, before hitching up her tweed skirt and removing her very wet knickers pulling them over my head with the gusset over my nose.

Without a further word, I heard the sound of her shoes as she moved to the side of the room to hang her jacket over the back of a chair, before picking up the cane. My heart pounded in anticipation as I felt my gym slip being folded over and the hem pinned to the back with a safety pin to expose my backside for punishment. This was followed by the sound of the cane cutting through the air as she practiced a stroke. After a second or two I then felt the cane against me and the sound of her heels on the floor as she adjusted her position for the first stroke.

“You are about to receive thirty-six strokes of the dragon cane for self-abuse. It will hurt because it’s meant to.”