Mr. Winters called me an acquaintance from a social function a few months ago. We had a pleasant conversation, and I mentioned that I worked as an accountability coach for individuals seeking to add more organization to their lives.

After exchanging brief pleasantries, he shared the purpose of his call. He revealed that he had a problem and thought I could assist him. He mentioned that his wife, Evilyn, required my expertise and proceeded to explain the details as to why.

The head of the exclusive private school where his children were enrolled contacted him. This was a highly prestigious school with a lengthy waiting list for admission.

The headmaster had a serious conversation with him regarding his children’s habitual tardiness to school. Despite multiple written warnings and a phone call with Mrs. Winters, their punctuality had not improved. If the situation did not change within the next month, they would have no choice but to consider expelling his children from the school.

Mr. Winters elaborated on his current project, which required him to work abroad and only allowed him to come home for a weekend once a month. As a result, he could not personally handle any matters involving his wife.

Their children were late to school mainly because of his wife’s lack of motivation. With no job, she had no valid explanation for her behavior. He wondered if my accountability coaching could assist with her chronic lateness and other minor issues, such as skipping the personal training sessions he had paid for at her request.

After listening to his explanation, I asked if he knew my methods of holding clients accountable, specifically regarding individuals like his wife.

He responded that he had heard of my use of corporal punishment as a form of discipline, such as spanking, with clients.

We continued our conversation about his wife. I discovered that she received a substantial monthly allowance, which she always exceeded on lavish purchases such as clothing, dining out, and beauty treatments.

His only expectation of her was that she would fulfill her duties as a mother and care for the children. He had hired a live-in lady to handle cooking, cleaning, and laundry tasks. Mrs. Winters’ primary responsibility was transporting the children to and from school and being their mother figure.

He knew she was a great mother, always caring and loving towards their children. However, he also realized that her laziness and entitlement were partly his fault for not setting boundaries or expectations.

After hearing him out, I advised him to have a serious discussion with his wife that evening. He needed to let her know that she had a decision to make: either make positive changes or risk losing essential privileges. To support her in making improvements, he hired an accountability coach who would assist her in implementing structure, guidelines, and limitations in her life.

We made plans for Mrs. Winters to meet me in my office at 11 a.m. on Friday, and I asked Mrs. Winters to emphasize to Mrs. Winters that I do not tolerate lateness.

Since he would be away for work, he set it up for me to manage her allowance. I had the power to transfer money as needed from her cards. If she didn’t agree to our agreement, she would not receive any allowance until she did so, and he would inform her of this when they had their talk.

The following morning, I received a text from Mrs. Winters confirming that the displeased Mrs. Winters would attend the meeting scheduled for 11 am on Friday.

Friday was a beautiful day. I stood at my office window, gazing down at the stunning view of San Francisco City, which never failed to captivate me. Glancing at the clock, I noticed it was already 11:05 a.m., and Mrs. Winters had yet to arrive. I walked over to the cupboard where I kept all my disciplinary tools and selected the headmaster’s style cane, placing it prominently on my desk. Today, Mrs. Winters will be receiving a lesson in punctuality from me.

At 11:11, the intercom by my desk let out a loud ring. It was Mrs. Winters, so I pressed the button to let her in and instructed her to sit in one of the chairs in the waiting area. I assured her that I would be with her momentarily.

I purposely made Mrs. Winters wait for 11 minutes, the same time she had kept me waiting. I knew this would not be a pleasant experience for her, as she would have to look at the pictures on the walls of my waiting area, which depicted spanking implements and quotes about discipline. From previous students, I knew that this only added to their anxiety while waiting. I preferred to view the people who came to see me as students rather than clients, as many did not hire my services. They were here to learn valuable life lessons.

After eleven minutes, I walked to the door and opened it, welcoming Mrs. Winters inside. I gestured towards the chair in front of my desk for her to sit down. As she settled into the seat, I sat down and walked around to my chair.

As Mrs. Winters entered the room, it was immediately evident where She was spending her allowance. Her hair and makeup were perfectly done, with long, streaked dark blonde locks and subtle highlights. She wore a low-cut white silk top with just enough cleavage to remain modest and a tight-fitting skirt that hit above the knee. Her legs were adorned with stockings, and she wore high heels. Her jewelry, gold earrings, and necklace screamed luxury. To complete the look, she carried a costly Gucci handbag.

I began our discussion by acknowledging that Mrs. Winters was 11 minutes late and asked why. She responded casually, saying it was only 11 minutes and that it was good for her since she is usually at least 20 minutes late; time just slipped away.

I asked her why we were meeting today, and she replied that it wasn’t her decision to meet with me. She also clarified that she had better things to do than waste her time here, but her husband was in a strange mood last night and threatened to cut off her allowance if she didn’t attend. She mentioned that you were to oversee my allowance, so I decided it would be best to go along with her hubby’s silly game and appear cooperative until he got bored, and things returned to normal.

I inquired about the purpose of Mrs. Winters’ arranged meeting, and she replied that it was related to the school’s complaints about her children occasionally arriving a few minutes late and her tendency to go over budget with her insufficient allowance. She deemed these matters unimportant and silly, but her husband insisted she come here to talk about them.

I replied that those are the key issues, but they are not silly, and we are not just here to discuss them.

Let’s clarify—I have complete control over your allowance now. It’s up to me whether I decide to pay you. Mrs. Winters responded sarcastically with a dismissive “whatever” as long as the payment was on time.

I clarified that her allowance would only be given if she followed my instructions. I also warned her that I could take it away whenever necessary.

Mrs. Winters objected, saying it wasn’t fair, but I reminded her she had caused this situation herself.

I stated that it was time to begin, as we had a lot of ground to cover. The first matter we needed to address was her being 11 minutes late this morning, which was not acceptable and would not be tolerated. As a result, she had earned her first session with the cane that rested on my desk in front of her. She would receive eleven strikes across her bare cheeks as punishment for her tardiness.

Mrs. Winters’ face was filled with disbelief as she exclaimed, “There’s no way that is happening! You can forget about it; let’s set the record straight now.”

I inquired if her husband had failed to explain the role of an accountability coach, and she responded that she thought he was kidding. She found it ridiculous to believe that a fully grown woman would be sent by her husband to meet with a coach and receive a spanking.

I clarified to her that this was not a joke and gave her an ultimatum: either accept the punishment, or I would immediately withdraw her allowance.

Mrs. Winters replied with a simple “fine” before asserting, “I’m going to leave; there’s no way in hell you will ever spank me, Mister.” With that, she stormed out of the room and slammed the door behind her.

Mrs. Winters departed, and I immediately froze her cards, preventing her from making further purchases. However, fifteen minutes later, the office intercom buzzed with a call from Mrs. Winters, who demanded that I unfreeze her card so she could request an Uber ride home.

I offered her the option to either come up and talk about it or leave and walk home.

Mrs. Winters uttered a low curse as she stormed toward my office, determined to resolve the issue. I invited her in and sat her down before calling her husband on speakerphone. With Mrs. Winters by my side, I explained the situation to her husband—how she had refused to accept the discipline and left, resulting in me freezing her cards. Now that she was back, she demanded that they be unfrozen immediately and that he intervene so this wouldn’t happen again.

Mr. Winters told Evelyn that she would have to follow Mr. Masters’ instructions or her allowance would be cut off. If she needed money, she would have to find a job.

Mrs. Winters warned him that if he didn’t stop this behavior, he would no longer be allowed in her bed. Mr. Winters chuckled and pointed out that he would be gone for four weeks anyway, so that it wouldn’t make much of a difference to him.

He then hung up.

Mrs. Winters was in a state of disbelief. The current situation felt more like a nightmare but was all too real. She finally realized that to have her cards unfrozen, she would have to submit to being caned on her bare bottom by a stranger.

She had never been spanked by hand, never mind having been caned.

I granted Mrs. Winters a bit more time to consider her options before she responded to my question.

After some thought, she resigned, “It seems I don’t have much choice. I suppose, for now, I must do as you say.” However, she added confidently, “I am also certain that Marcus will change his mind later this week.”

I told Mrs. Winters to remove her skirt and bend over my desk, ready to receive 11 cane strikes. She had wasted 11 minutes of my time by being late to our meeting, and I would not tolerate such disrespect.

Mrs. Winter got up and slowly took off her skirt, revealing that she was wearing stockings, suspenders, and a thin red thong, which was fortunate for her as it saved her from having to remove her panties so I would have bare cheeks to land the cane on.

I gestured for Mrs. Winters to stand before the desk, instructing her to lean over it with her hands flat on the surface and palms facing down. I made sure to remind her not to move her hands during the punishment, as I didn’t want her to get hurt by the cane accidentally.

Next, I asked her to count each strike as it landed on her bottom. I ensured she understood that any failure to count would result in that strike not being counted, and we would have to start all over again.

I took a few practice swings with the cane before positioning myself to discipline Mrs. Winters. When I struck her for the first time, she let out a scream of agony. I reminded her to count and say “Sir” at the end, making it clear to her.

With each strike, her screams grew louder. Two angry red marks appeared on her otherwise pale and round buttocks. I kept striking with the cane, causing gasps and screams to escape her lips. When I reached ten strikes, I took a moment to aim carefully and landed the final swing in the center of her seat spot, making it just a bit harder than the previous strikes.

After the final strike, I asked Mrs. Winters if she had learned her lesson about being late. She nodded and promised, “Yes, Sir. I will never be late again.” The thought of receiving the cane again was enough to ensure her punctuality in the future.

I then let her know she could put her skirt back on, and we could begin discussing the plan of action for the future.

To be continued