Private School Discipline

BeachBum25

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John Montgomery...32/m.... 6'1".....180 lbs.... Light brown hair.... blue eyes..... athletic build....

John Montgomery had been a school teacher. That all changed when he met the woman who would be his wife. It was at an alumni function. He saw her there and began chatting with her. It turned out that she was the daughter of a multi-billionaire. They had a whirlwind romance that resulted, much to her father's dismay, with them getting married. His father-in-law was not happy about his daughter being married to a lowly teacher. So, when the Headmaster of a school that he had been one of the principal financiers of retired, he insisted on John becoming the new Headmaster.

John was not crazy about the idea. He loved teaching, especially at the inner-city school in which he worked, but he really did not have much of a choice. So, he took over as Headmaster of the Pilgrim Day School. John went right to work. He worked long and hard to convince people he could do the job. Many of the parents and staff members were not happy with his choice. They saw it like it was.... John got the job because of his wife's daddy. However, his hard work paid off. He made a good school even better. His wife was not happy, though. She did not like the fact that John was working long hours. She wanted him to pay more attention to her. When that didn't happen, she filed for divorce. Her lawyer made John an offer: keep his job as Headmaster and keep the penthouse apartment and give up everything else. It was that, or, if he chose to contest, he would risk losing everything. He chose not to contest.

One of the things that John brought to Pilgrim was discipline. The children who attended Pilgrim were from extremely wealthy families; either that, or they had a wealthy benefactor who paid their tuition. Discipline had been lacking in the school when John had arrived. That was one of the first changes he made. If students could not behave appropriately, they did not need to be at Pilgrim. At first it was a battle..... students resisted, and, of course, so did their mommies and daddies. John stood strong though, and after the child of a famous e actor was kicked out of school, the parents realized he was not playing. Discipline problems had become almost non-existent.

There was always one though. Today John had a meeting with a parent whose child continued to have discipline issues. Today's meeting was to tell the mother to take her child home and find another school, because Pilgrim did not seem to be the right place for him.
 
Erica Wellington, 28 years old, 5’5, slender, red hair, green eyes, C cup.

Life was mostly a blessing to Erica. While she was not born in riches, she was lucky enough to meet Howard Wellington soon after she had finished her study in psychology. Howard came from a wealthy family, and perhaps that appealed more to Erica than truly any love. Howard mostly seemed interested in her looks and having someone next to him at various fundraising events. Their marriage produced one son: Alex and Erica doubted there would ever be a second.

Alex was a troublemaker. He was wise enough to show some respect to his parents, but to others he was mostly a spoiled brat that always looked for any way he could get in trouble. Already he had been to several schools until Howard had managed to get Alex to Pilgrim Day. A small financial donation had certainly helped but money only went so far.

Today Erica was once again summoned to the school. Howard had to work, as always, and couldn’t go with her but had entrusted her with preventing Alex was expelled. Money played no role when it came to the education of their son.

Dressed in an expensive designer’s blouse and a skirt that reached to her knees, Erica arrived at the headmaster’s office. She really hoped everything would work out although she had no idea what her son had done this time.

- “I am here to see mister Montgomery”

She told his secretary and then waited for her appointment.
 
John decided to let Mrs. Wellington wait for a while, before dismissing her son from the school. She had been to his office several times about her son, Alex's, discipline issues. She was very attractive, and was always well dressed. Each of her visits had been followed by a phone call from her husband thanking John for his understanding, and by a generous contribution to the school's endowment fund. John wondered what the follow-up call would be like this time. The thought of it made him smile.

At about 15 minutes after her appointment time John called his secretary and asked her to show Mrs. Wellington in. When she walked into his office, John decided to enjoy the moment. He allowed his eyes to move slowly over Mrs. wellington's body. Then, he looked into her eyes and smiled at her. "Please have a seat Mrs. Wellington," he said; pointing at one of the leather chairs in front of his desk.

He waited for her to sit, before he sat behind his large oak desk. "I am sure you know why you are here."
 
Erica was still young enough to remember the feeling of being summoned to the head master’s office herself, although her ‘crimes’ had never been worse than talking and giggling in class. Her son however had a skill of pushing things a lot further. Before entering the office she adjusted her skirt a bit and then walked in. She didn’t look at his eyes so she missed the way he was checking her out as she walked and took a seat.

- "I am sure you know why you are here."

He said and she nodded.

- “You wanted to talk to me about my son Alex. I am sorry for whatever he did this time.”

She answered, expecting the headmaster to tell her exactly what her son had done this time. Hopefully money would take care of the problem again; Howard would not be pleased if their son got expelled. Still she did not make direct eye contact with him.
 
"I must tell you Mrs. Wellington that these meetings about Alex are getting quite tedious. I am not sure what is going on, but it is obvious tome that Alex's behavior is not improving." John stared right at her, although she never raised her eyes to look at him.

"Do you not have any manners? Don't you think that it is appropriate that you make eye contact with someone that is speaking with you? Maybe the problem with your son is you. Maybe you have not raised him properly." He waited to see her reaction.

"I don't think that your husbands money is going to buy you or your son out of it this time. I must tell you that Alex's days at Pilgrim are over. I can simply not tolerate his behavior any longer. He is undermining everything we have done, and everything we stand for at Pilgrim. I refuse to allow that to happen any longer."
 
A blush came to her cheeks when he called out on her not looking him in his eyes and she immediately did so. She was nervous and shy, which was clearly visible on her face and the shock only became worse when the headmaster continued. She had no idea how to explain to her husband that Alex was no longer allowed at Pilgrim.

- “I… You… He… You can’t do this…”

She stammered, both upset he was calling her parenting skills poor but mostly with Alex being kicked from the school. A tear escaped her eye and her face was rather pale.

- “There must be something we can do. Please, we have always been good to the school. We will talk with him and make him behave.”
 
"What about the other times. Are you telling me that you did not speak with him the other times that you came in here?" He looked deep into her eyes. The comment she made made it seem like they believed money could buy them out of everything.

"How have you been good to Pilgrim? The only thing that your family has brought to Pilgrim is an increase in out endowment fund. If that is all I was worried about I would simply summon you to show up with your check book and write me a huge check. No, Mrs. Wellington, you have not been good to this school. You have not instilled in your son the discipline that he needs to be successful here."

John stood up and leaned on his desk. "Perhaps the problem is that you do not know what true discipline is. Maybe if someone had taken the time to show you proper discipline your son would be okay and would not always be in trouble. So, unless you have something else to offer me, I have to tell you that this meeting is over."
 
Of course she had talked with Alex every time he had gotten in trouble, and of course every time he had promised he would behave. And yet, everyone involved had known there would be a new time he would get in trouble. The money had always given him a way out, but now it seemed the headmaster had made up his mind and could no longer be bribed.

- "Please... there must be something I can do? I can have Alex wash your car for you... or..."

She pleaded, not very sure what she had to offer that would have him change his mind.
 
John could not believe what he was hearing. She was offering to have her son wash his car. Did she really think that would change his mind and let her brat of a kid stay in school? This confirmed what the real problem was.

"Is that your idea of discipline? Are you kidding me? You really think that Alex washing my car is going to convince me that he should stay at Pilgrim? Mrs. Wellington, I am starting to be convinced that you are the real problem here. You have no idea what it is to discipline your child. If you did you would not have to come prancing in here all dolled up as often as you do.."

He let that comment linger for a minute. Still standing and leaning on his desk....looking down at her. "Maybe you need some classes on discipline. It might help you in raising your child."
 
Finally there flashed some anger in her eyes, but that was only because he called her out on her clothes. There was nothing wrong with her clothes, she dressed according to the latest fashion as she should. But of course she was not going to debate with him about her being 'dolled up'.

She looked at him when he suggested classes for her. Perhaps there was a way Alex could stay.

-"Classes for me? And he could stay then?"

She asked

-"What do you have in mind?"
 
"I don't recall saying anything about Alex being able to stay. I was just giving you some direction on how you might be able to do a better job with your son." He smiled at her. He knew that he had her wrapped around his finger, and he could probably get her to jump through any hoops he wanted.

"So, now, you are interested in learning some discipline. Well, what I have in mind really depends on how bad you want your bratty fucking kid to stay in my school. If you are interested in keeping him here you will return this evening at 6 o'clock....alone. At that time I will begin your lessons, and I will give you the guidelines for your son remaining a student here. Show up one second late and you might as well not come at all."
 
She nodded, happy that there was a way to keep Alex on Pilgrim after all.

- "I will be here. I will do anything you want to have him stay here."

She promised, not really aware of what she was promising or getting herself into.

- "Do I need to bring something?"

She then asked, not wanting to mess up this one chance. Of course 6 o'clock was not the best time as it interfered with supper and with travel time she would miss most of her tv shows, but everything was better than explaining Howard that she had failed him.
 
"Don't even think about being late." He watched as she got up and walked toward the door. "Oh, and by the way, don't forget to have your husband send his check to the endowment fund." He smiled at her and sat down behind his desk.

He spent the remainder of the afternoon finishing up the paperwork he had to do and clearing off his desk. He was going to enjoy this evening. It was about time that one of these high society spoiled brats got taught a lesson. She was going to learn about discipline, and he was going to enjoy being the teacher.

At 5:59 he opened the door from his office to his outer office. He wanted to see if she was there yet, and if his clock ticked to 6, he would close the door, go back to his desk, and complete the expulsion papers for Alex Wellington.
 
She hadn't told her husband anything about the meeting. Not until she knew how the evening would turn out. She had just told him she had to go out for the evening and wasn't sure when she would be back.

She had left early but when she arrived at the gate to the visitor's parking, she found it closed. She cursed softly and quickly searched for a spot to park her car elsewhere and then had to hurry. Eventually she took off her high heeled shoes so that she could walk faster and soon was even running to be in time.

Just before the headmaster was about to close the door she made it to the office. Heavily breathing and trying to regain her breath.

- "I'm here..."

She said
 
"Hmmmm, cutting it a little close I see. I didn't think you were going to make it. Put your shoes back on and then you can come into my office and have a seat in front of my desk." He watched her bend over and put her shoes back on and then followed her with his eyes as she walked past him and sat in the same chair she had been earlier in the day. His eyes took special notice to her firm breasts and tight ass as she walked past him. He closed the door and locked it.

He went and sat behind his desk. He looked across it at her. "We'll, you have taken the first step toward keeping your kid in MY school. We will see if you are capable of going through with it." He paused to gauge her reaction. He wanted to see if she was really committed.

"Do you understand what rue discipline is? Do you understand that discipline involves doing exactly what you are supposed to do without questioning and without hesitation? Do you think you are capable of that?"
 
She blushed as she put her shoes back on, knowing how silly she must look. She was still dressed in a blouse and skirt, but different ones than earlier. As she sat down on the chair, she didn't notice he locked the door.

As he sat down she forced herself to look at his eyes. She was in no mood to again be embarrassed about that.

- "I will do anything I can to learn."

She said softly, nervous knowing that most of the school would be empty at this time.
 
"That is good to hear. The first thing that I want you to understand is that every time your precious little boy does something that is inappropriate, it is you that is going to be punished. I am the one that will administer the punishment, and it will get more severe each time. The first time you choose not to accept the punishment, he is gone, and you run the risk of your husband finding out how you kept the kid in school."

He stood up and walked around the desk and sat on the edge of the desk in front of her. He looked down at her and smiled a wicked smile. "I need you to tell me right now if there is any reason I should believe that you will not do as I tell you to do and follow all of my instructions."
 
She gave him a confused look as he spoke of 'punishment' for her. She doubted it would do much good to have her write lines of punishment instead of her son, or what ever punishment schools had these days. But still, anything to keep her son at school. She shivered slightly in her chair when he walked closer, keeping her effort up to look at his eyes.

- "No... I will do anything you tell me if it is within my power to do so."

She said, a nervous shiver in her voice
 
"Good. Now, get on your knees in front of me. Don't hesitate. Don't think about it. Just do it. Right fucking now." His voice was stern and left no doubt about his seriousness. It also sent a message that if she did not do as she was told, the deal was going to end real fast.

He didn't smile at her. He didn't frown at her. He just looked into her eyes and waited for her to comply. He had a plan for her. Someone this rich and this spoiled had to be taught a lesson. Someone this beautiful also had to be taught how to use what she had been given.
 
For a moment there was a look of surprise at his instruction but then she did as she was told. The floor was rough under her knees and she felt embarrassed to be in this position but she hoped it would show she would listen.

When she was on her knees she looked up at him again and the look she saw on his face made her more nervous than anything that had happened so far. Still she had no idea what he had in store for her.
 
It was very obvious to John that Mrs. Wellington had no clue as to what she had agreed to. He was sure that she thought that what was going on was going to be something in which she was responsible for doing things that her son might normally have to do...... She was so, so wrong.

He moved off the desk and moved around her. He moved the two leather chairs out of the way as he slowly walked around her. When he had totally circled her, he stood right in front of her...only inches between their bodies. "From now on, any meetings that take place between you and me will occur at the same time. 6 pm.....not one second later. At those meetings, you will enter my office on your knees and remain on your knees unless I instruct you to do something different." He put his hand under her chin and lifted her head to him. "I am going to enjoy this."
 
She tried to nod in reaction to his instruction but his hand under her chin made that impossible. She was not sure why he would enjoy this, she just knew that this position was rather humiliating to her. Alex better made sure she wouldn't have to come here more often.

- "I will be here at 6 pm, when ever it is needed... and will be on my knees in your office"

She agreed softly to the headmaster. Her knees were getting annoyed with the hard floor under them and she tried to readjust herself a little.
 
He caressed her cheek with his thumb. "You will call me Sir, and nothing else.....ever." He hesitated for a second. "You are such a pretty little thing. I bet your hubby loves parading you around in front of all of his wealthy friends and acquaintances. I bet they all talk about how lucky he is to be going home with someone as hot as you. Does it make you feel good to be on display for your husband? Do you like him using you like that?"
 
The way he touched her cheek was making her very uncomfortable. She had no trouble calling him sir but his comments and questions that followed she found very personal and it showed on her face. She was wise enough not to complain about it.

- "I don't know what they talk about Sir. I just am a good wife to my husband."

She answered, although she knew her looks were all he married her for.
 
"You are a good wife? Do you give your husband what he wants?" He knew he was making her uncomfortable. That was his plan. Get her out of her comfort zone. See just how far she would go with him.

"Do you think he has ever discussed what he has done with you with his friends? I bet he has told them all about you and what he has done to you and what you have done to him. And I am betting that, despite all that, you want more than he has given you....or will ever give you."

He moved his hand to her shoulder and caressed it lightly. "Do you want me to stop?"
 
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