Boarding School Sex Training-Chapter 1

“I am glad, I have not seen him in a while. Is there anything the matter, Headmaster Michael?”

“No, everything is fine with Stephen. He is looking forward to seeing you tomorrow. We just have to come to some decisions about your future before he arrives.”

“What do you mean?” asked Rachel.

“You are now eighteen today and that makes you an adult. I need to explain some things about your future relationship with Stephen and how you are to proceed. When your parents died eight years ago, they left you an inheritance of a little over one million dollars, with Stephen the trustee.

“I didn’t know anything about that. When will I inherit the money?” Rachel inquired. Her eyes began to lighten up. That was a lot of money, she could do many things that she had only read about.

“I realize that it sounds like a lot of money, but Stephen has had to financially take care of you for the last eight years. You must realize your education and board at this school costs almost $150,000 per year. While Stephen is wealthy, he is under no obligation to pay for your tuition with his own money. As trustee of your parents estate, he has every legal right to use the inheritance money for your upkeep.”

The good mood of Rachel quickly disappeared, as she realized that there was little money left of the inheritance. She would be back to having no future without the help of Stephen. “So what does this mean?”

“Stephen has a proposition for you Rachel. He is willing to forego all of the payments he has made for the last eight years and give you the inheritance when you turn the age of twenty-one. This would be about two million dollars, as Stephen wisely invested the money for you. Does this sound interesting to you, Rachel?”

“Oh, yes, Sir. I want to thank you and I will really thank Stephen tomorrow when he comes,” the excitement back in Rachel’s voice. She would be rich and could do anything she wanted to.

“Don’t get too excited yet, Rachel. There are some conditions to this agreement. Stephen is being very generous to you and he requires some exchange of favors in return.”

“Yes, I will do whatever he wants. He has been so generous towards me since my parent’s death. And you have also been so helpful, Sir. I respect you for the many things you have taught me the last eight years.” Rachel could not contain her enthusiasm. She would be financially set for life. While most twenty-one year olds would be just starting out in life, she would be financially sound.

“I hope you are sincere in your desire to please both Stephen and myself. That is exactly what will be required of you in order to get Stephen to complete his offer.”

“I am sure I will please you both, Sir,” not realizing the implications of her response. “What is required of me?”

“As you probably know, Rachel, you have become a very attractive women. While you are sexually naïve, which was our intentions at this school for your development, it is now time for further education in that area.”

“I don’t understand,” a puzzled look on Rachel’s face. She had only begun to think of sex and with the few males here being the instructors, they were only passing fancies.

“Stephen has asked me to take over the personal training of you. This will take about two months. During that time, I will prepare you sexually for him,” his eyes watching for Rachel’s reaction.

Rachel sat up in the chair, did she hear him correctly, did he say, prepare her sexually for him. “What do you mean, prepare sexually,” she stammered, her voice breaking up.

“I will teach you to cater to Stephen’s every sexual desire. You will be taught to experience pleasure against your will and to give pleasure against your will. This will involve humiliation and if you fail to perform as desired, this will require discipline, often you will be sexually punished. You will have to serve his sexual desires for a period of three years. At the end of that time, you will be given your inheritance and you will be free to do as you desire. You may stay with Stephen, but that is not a requirement.”

“I don’t know what to say, Sir. I am not sure what you and Stephen are going to do to me. I respect your opinion, what do you want me to do?”

“I suggest you take Stephen’s offer. It is very generous. It will only require three years of your life and then you will have the wherewithal to do anything you want in life. Most young ladies would jump at a chance to take this offer. This is not an unusual request. I have trained a number of young ladies like you over the years that have accepted similar offers from their Guardians. I will not give you names, but you are going to school with one of them. In fact, if you accept this offer, your training will also interact with hers at some point.”

“Can you tell me what will be expected of me?” Rachel asked, still not exactly sure of what she would be expected to do.

“It is difficult to explain in words, but I can show you in pictures. I have an album of various sexual situations that you will be required to perform. Each day I will show you a new set of pictures for you to study and the next day I will instruct you in the methods to pleasure Stephen.” Michael reached over and pulled a large album over to where Rachel was sitting. He placed it in her lap.

“Open the first page and see your new future.”

Rachel was shocked at the first picture. There was a naked girl, her own age. In fact she recognized her. It was Sara, her roommate last year. She was standing, her legs spread, her arms laced behind her head, her breasts thrust before her. She was naked and she could see Michael in the picture and also someone else, probably her Guardian. She looked embarrassed as she was spread naked, their eyes obviously drinking in the naked beauty before them. The next picture showed her kneeling on hands and knees on the Headmasters desk. She could see the Headmasters hands on her thighs, spreading them open. Her anus and vagina peaking out. Her breasts hung down and her Guardian had grasped them with his hands. Each picture got progressively worse. On her back, her Guardian pulling her legs back and spread over her head, the Headmaster between her legs, a speculum in his hand. On her knees again, head down on the desk, ass pushed out, her Guardian spreading her cheeks of her ass open, the Headmaster inserting a speculum in her tiny anus. Tears ran from her eyes, the humiliation of the inspection of her body overcoming her emotions.

“We will require a complete inspection of your body first. That will take place tomorrow. Stephen will be present and will assist me in it. You will be forced to participate. We will require you to perform certain actions to allow us access to the various parts of your body. Part of your training will require you to do things against your will. Your only reason to do so will be to please Stephen and myself. This will be a very lengthy examination. You will be asked to strip naked for us. You will be given an enema so you will be cleaned out. You vagina and anus will be probed with speculums. I can assure you when we are finished, we will know your body better than you do,” Michael stated matter of factly.

The only two persons that she cared about in this world were asking her to do things that made her cringe. While not fully realizing what would be required of her she managed to stammer out, “I will try to please you both, you have both been very generous and kind to me over the years. I respect both of you and your opinions and if you think that this is best for me, I will do as you desire. You have only show me what is required of me and I will obey.”

Michael smiled, he knew that he would enjoy this delightful creature over the next two months. While he thought that he was getting the better part of the agreement, he realized the reason for Stephen’s request. Stephen had been in love with Rachel’s mother before she was married. They had a brief, very passionate affair, but she married his best friend, who was a millionaire, when Stephen was in comparison, poor and could not give her the lifestyle she wanted. Rachel’s mother was anything but innocent, she had given Stephen pleasure he’d never experienced before or after. Stephen expected Michael to train Rachel to be the whore that her mother was in bed. He did not want an innocent girl, but a sexually experienced woman that would not balk at any request.

“I realize that tomorrow will be a very traumatic experience for you. You will first be forced to strip naked in front of Stephen and myself. To make it a little easier on you, I am going to have you strip for me right now. You might as well get used to taking off your clothes in front on strangers. This will happen many times in your training. Please stand up and face me,” said Michael, sitting in one of the large chairs in the middle of the room.

Rachel, trembling in strange anticipation and fear, stood from the chair and moved in front of Michael. Her legs felt like rubber and she thought she might not make the few steps required of her. She did not know how she would handle the situation. She would be asked to remove her clothes while Michael watches her. Would she be able to do it?