Evilyn Winters Monthly Meeting

Part 2

After leaving Evilyn standing in the corner for 15 minutes, I finally asked her to return to the chair before my desk so we could continue. She replied with a quiet “Yes sir” and walked over to the chair, sitting gingerly in front of me.

I raised my head to meet Evilyn’s gaze and warned her that any further interruptions would result in an additional spanking for her.

I told her before she left today that I planned on giving her a debit card containing the remaining balance of her monthly allowance minus $300. This was to cover the cost of her overspending last month, which would be paid back at a rate of £300 per month till Evilyn paid it back. I would load the card with her allowance minus $300 for the following months. It was vital for her to remember that once the balance was zero, no more funds would be available until the beginning of the following month.

Evilyn responded with frustration in her tone, “What if I’m at a restaurant and can’t afford my bill?” I met her gaze firmly and replied, “Then you’ll have to start washing dishes or ask one of your supposed friends to cover it for you.”

I pointed out that we still had to address the issue of overspending by $1560 on a handbag that she couldn’t afford just to show off to her friends.

In addition to losing the use of her cards today, she would also receive six strokes with the cane today. Evilyn’s face paled at this news; her bottom was already sore from the hand spanking she had received earlier, and she didn’t think she could handle a caning on top of that.

I also mentioned an additional matter to address: she had not attended her personal training sessions for the past two weeks despite her husband having already paid for them. I asked her why she thought it was OK to waste the money her husband had earned on exercise lessons, which she never attended.

Evilyn hesitated before answering and then stated that she did not have enough time to go due to other obligations in her life, but she planned on attending the following week.

I responded by shaking my head and warning Evilyn that if she ever skipped a training session again, she would have to make up for it with an exercise session at my office. I also clarified that my training techniques differed from her current trainer’s.

However, due to her two-week absence, she was now facing six lashes of the belt.

Evilyn gasped and desperately pleaded, “Please, Sir, that’s too much. I’m already in pain from the hand spanking, and you intend to give me another 6 with the cane? I apologize, Sir, I will never miss an appointment again.”

I responded, “It’s too late, Mrs. Winters. The rules are clear, and there is no room for misinterpretation. You knowingly broke the rules, and now you must face the consequences.”

I told her to go to the sofa and bend over my arm while I retrieved my cane. As someone who has taken on a disciplinary role, my greatest satisfaction comes from helping clients reach their goals, learn their lessons, and become their best selves.

There is a part of me that enjoys being a sadist and derives pleasure from administering discipline to clients. Witnessing the transformation of a person’s bottom turning red from a spanking brings me great satisfaction, and seeing angry red welts and raised stripes form on tender skin triggers my endorphins.

With Evilyn bent over the back of the sofa, her bottom presented at the perfect angle for the caning she was about to receive, I took a few practice swings in the air before I began to administer her punishment. Her bottom was still pink from the hand spanking she had received earlier, but soon, I would cover it with red tram tracks as I delivered each strike against her already tender skin.

“Mrs. Wintersd, are you prepared?” I asked her sternly. She replied with a shaky “Yes, Sir. But please, I have learned my lesson.” Before she could finish her sentence, I had delivered a firm strike to the center of her bottom with the cane. The pain immediately registered in her brain, and she let out a piercing scream.

I urged Mrs. Winters to embrace the pain and use it as a learning experience. My second strike landed just above the first, followed by a third below it. With each strike, Evilyn let out a cry of shock and pain. Three angry red lines began to form on her delicate cheeks.

After a brief pause, I announced that three strikes were left, and then I delivered the fourth one between the first and second strikes. Then, quickly, I landed the fifth one between the first and third strike. Evilyn’s sobs became muffled as she buried her face into the sofa cushion while her cheeks burned from the fiery pain. For my final strike with the cane, I aimed to land it directly on top of the first. After a few practice swings, I firmly struck down, causing Evilyn to scream out in shock from the sudden intensity compared to the previous five strikes.

After returning my cane to its designated spot in the cupboard, I admired my handiwork on Evilyn’s burning bottom. It was a masterpiece if I say so myself.

I unfastened my belt from my trousers. This was no ordinary belt; it was a thick 21/4-inch wide piece of leather that I knew from experience delivered immense pain to badly behaved bottoms.

I asked Evilyn if she was ready for the last portion of today’s discipline: the belt. At this point, Evilyn seemed to have accepted her punishment and meekly responded with a simple “Yes, Sir.” She didn’t even attempt to plead or argue against it, knowing there was no use. I folded the belt over itself and coiled it around my hand until I had the desired length for the punishment I was about to administer.

I carefully considered where I wanted to land the lashes, starting at the bottom of her cheeks, where they met her thighs. Then, I would move on to covering her buttocks with four more strikes.

The first strike of the belt caused Evilyn to jump in shock. It was her first time experiencing the painful sting of a belt, and it was unlike anything she had felt before. The fiery sensation it left behind was excruciating. I commanded Evilyn to get back down and warned her not to move again, or else we would have to start from the beginning. She obediently got back into position as I delivered four more lashes to her already marked bottom, carefully targeting every inch and gradually moving up her buttocks. Evilyn was now sobbing uncontrollably from the intense pain.

Evilyn not only experienced pain on her rear end from the belt, but it also left angry marks on the side of her buttocks as well. The end of the belt had curled around and left five distinct marks on the cheek and five broad strips that blended into each other on her bottom.

I reiterated to Evilyn my warning that if she missed her next exercise session with her personal trainer, not only would she have to complete the workout, but I would also give her six lashes with the belt before and after in front of me.

I informed her that there was only one more punishment left, and I directed the last lash towards the back of her thighs. Evilyn let out a piercing scream and thrashed her legs in agony from the intense pain of the belt on her highly sensitive thighs.

I quickly fixed my belt as I watched Evilyn crying, hunched over the sofa. When she calmed down, I helped her stand up and suggested she wash her face in the bathroom. After she returned, I told her to get dressed but recommended that she not put her panties back on to avoid any further discomfort. Evilyn slipped her skirt back on and carefully pulled it over her bottom before tucking her panties into her purse.

After escorting Evilyn to the door, I reminded her that she and her friends would be returning on Saturday for their punishment due to their recent late nights.