Boarding School Sex Training

{ASSM} Boarding School Sex Training. (Lady Dreamer and Powerone)
M+/F, Virg, Reluc, Humil, Anal, reluc

This story is collaboration between Lady Dreamer and Powerone. Copyrighted 2002. It is a story of the coercion of a young lady, Rachel, to fulfill the sexual desires of her older Guardian. In order to gain the inheritance that is rightfully hers, she must consent to be trained by the Headmaster to service her Guardian. She will be taught to experience pleasure against her own will and to give pleasure against her will. She will be trained in all the perversions of the flesh. Powerone can be reached at controlher@hotmail.com

Her Guardians Wishes-Chapter One

Michael has been the Headmaster of a very exclusive all girls boarding school for over ten years. Michael is very much a lover of the female figure; he appreciates shape and form of women and above all, likes to take pleasure from them whether they wish it or not. He likes to force them to feel pleasure that they might not wish to feel or experience. Michael’s philosophy is absolute obedience to his word and his school is very strict. Students are brought up to respect adults and not to question them. Any disobedience is quickly punished. All of the instructors at the school are male.

The tuition at the school costs more than $150,000 per year and the student’s guardians enroll them at the school. The guardians are all very wealthy older gentlemen. They became guardians over the students when their parents had died.

The students are sexually naïve and when they became eighteen the real purpose of the school becomes evident. This is the story of one of these students, Rachel.

Rachel has a slender figure, medium height, peaches and cream complexion, long wavy brown hair and unusual gray/blue eyes. She turned eighteen years old today and has been at the boarding school since she was ten. Her parents were killed in an automobile accident. Stephen, her Guardian was a good friend of her mother and as Rachel had no other relatives, he petitioned the court for custody of Rachel. Stephen is a very rich and powerful man. He had no trouble convincing the court that he could care for Rachel. While Stephen does maintain contact with Rachel, her real guardian is Michael. She adores him (hero worship), thinks the world of him and would do whatever he wants. She would not even think of questioning his authority. The one time she did, when she was twelve, Michael had taken her over his lap and spanked her ass. That was the last time she ever questioned him.

As Rachel entered the classroom, Mr. Johnson called her over. Rachel is wearing the standard dress for the school. This consists of a white, button down blouse, plaid skirt, saddle shoes and socks. Although Rachel thought the blouses were a little too transparent (you could see the outline of her bra underneath) and the skirts a little too short (they were three inches above the knees) she does not complain. The only males she ever saw were the instructors and although she felt sometime that they were looking at her strange lately, she ignored the feeling.

“Yes, Sir,” said Rachel.

“Headmaster Michael would like to see you in his office immediately. Here is a hall pass,” remarked Mr. Johnson, with a smirk on his face.

All of the students called him Headmaster Michael. While the other teachers were respectfully called by their last name, the Headmaster used his first name. But he required you also used the term Headmaster with his first name. Either that or you called him Sir. Anything else would bring about his displeasure.

Rachel knocked on the door and waited for a response. It was a large oak door, befitting the owner’s power and prestige.

“Enter,” came the booming voice of the Headmaster.

Rachel entered and as usual was amazed by the grandeur of the office. One does not get called to the Headmasters office very often and when they did, they did not speak of it. The furniture in the office was all wood and very ornate. The chairs all were cushioned, with wooden arms and scrolled legs. They were very heavy and did not move very easily. The Headmasters desk was huge, as was the conference table. Little did Rachel realize that they were designed to hold a female figure securely to them.

“Have a seat, Rachel, and Happy Birthday. Stephen also sends his Happy Birthday wishes. He could not be here today, but he promises to be here tomorrow.”

Michael had a very striking and handsome silhouette. Although he was in his forties, he still was a heartthrob to most of the adolescent girls at the school. While they feared disobeying him, most also had adolescent fantasies about him. Rachel was no exception. Lately she thought about Michael spanking her as he did when she was twelve. This excited her, the power that he would have over her.

“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 tim
e for further education in that area.”

“I don’t understand,” a puzzled look on Rachel’s face. She had only begun to th
ink 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?

“What do you want me to do, Sir?” her voice very low, hoping that this was all a dream and she would wake up in her bed.

‘You have a very beautiful body, Rachel, I am would like to see it better. Remember the first picture, with Sara standing with her hands laced behind her neck and her legs spread wide? Even though you have your clothes on, I would like you to take that pose for me. You will be required to be in the pose many times as it will thrust your breasts out and spread your legs,” his cock beginning to harden.

Rachel closed her eyes and assumed the position. Her breasts strained against the buttons of her blouse, her legs spread wide, waiting for further commands.

“Open your eyes and look directly into my eyes. I want to see your humiliation. You have very lovely breasts. They are pushing to get out of your blouse. And you legs are very long and slender. You certainly have a body that was built for sex.”

Rachel opened her eyes and stared at Michael, her look catching the crotch of his pants. She could see his bulge. Some of the girls had talked about a man’s penis, but she had not even seen a picture of one. But she did know that Michael’s penis was big by the size of this bulge. She did not even want to imagine what he would do with it to her body.

“Turn around, so I may see your ass.” Rachel turned her back to him. “Yes, that is very lovely Rachel. Lower your hands and bend over, but do not bend your knees and grab your ankles.” Rachel could feel the cool air slide up the back of her skirt. She knew that her skirt was riding up to high to her butt and Michael could probably see her panties. “Spread your legs more, further, yes, that’s better. A woman is truly sensuous when she is spreading herself open for her
male. You have a beautiful ass Rachel, I am getting to take pleasure in it late
r. It is also made for a sound spanking. I still remember the spanking I gave you when you were twelve. You will receive spankings, not so much as a punishment, but because I want to. Your naked ass will excite me.”

“You are obeying very good, Rachel. Now turn and face me again, hands down. Step a little bit closer, so I may touch you if I desire.” Rachel moved closer to Michael, he could now reach out and touch her body. “Please unbutton your blouse and let if fall to the floor.”

Reluctantly, Rachel began at the top button and started to unbutton them. She stared at Michael as he watched her undressing. When the last button was opened, Rachel pulled it from her skirt, slipped it off her arms and let it fall to the floor. Rachel began to turn red in embarrassment at what she was being forced to do.

“Bend over and lean forward a little bit. I want to see your breasts.”

Rachel bent over, her breasts hanging open, seemingly trying to fall from her bra.

“A little more, yes, you have lovely breasts, Rachel. Now stand tall, remove your bra and than lace your hands behind your head again. Let me see your lovely breasts.”

Rachel cringed at the request. The man she respected and worshipped for almost all of her life was now asking her to show her naked breasts to him. Soon, she would have to strip completely for him. She was not sure if she could handle this. She felt like running away and crying. But, she had promised to obey him. He knew what was best for her. She would have to comply. Her fingers reached behind, finding the catch to her bra. A quick snap, a pull down from her shoulders and the bra fell to the floor, her arms covering her naked breasts.

“Hands behind your head, I will not repeat myself,” Michael’s voice boomed. “Your reluctance will cost you, now obey immediately.”

Rachel jumped at the anger in Michael’s voice. She had never seen this reaction since he had spanked her. She was afraid of the consequences and her arms went quickly behind her neck, fingers laced, elbows forward. Her young naked breasts caught the cool air in the room and her nipples hardened, standing tall, the first time a male had seem them. A flash of excitement, but also feared rushed through Rachel. Her eyes met Michael’s.

Michael abruptly stood up, his face only inches from Rachel’s. He started into her eyes, seeing the fear. His glance went down to her breasts. He always enjoyed the breasts of a young girl. Rachel’s breasts were so firm, the nipples hard, her chest heaving from the fear. He watched her eyes follow his stare, his hands reaching up to touch them.

Rachel was shocked and almost pushed back when Michael stood. She watched in slow motion as his hand moved toward her naked breasts. What would it feel like when he touched her? She braced her body as first one hand, than the other encircled her tender breasts for the first time. She could feel her nipples harden as his hand clenched her breast tightly, squeezing them like a sponge. She gasped in sudden shock, not expecting the reaction from her body. She began to feel the excitement of the moment. Here she was being forced to strip naked and her naked body was being stroked and she was beginning to enjoy it. She wanted more.

Michael could feel the change in Rachel. She pushed her breasts into his hands. He moved toward her nipples, grabbing it between two fingers and began to pinch them lightly.

“OH, God, please don’t do that,” she cried, her breath coming in short bursts. His fingers began to become more insistent, the pinch becoming harder, pain beginning to mix with the pleasure, her nipples forced hard between his fingers. “That’s beginning to hurt, please don’t do that.”

“Stand perfectly still, you must let me have my way with your body. Let the pleasure overcome the pain. You will have to learn to love the pain. Stephen and I will take great pleasure inflicting pain on your body. That is what we require of you.” His fingers began to pull on her nipples, forcing them out. He pulled them up, Rachel forced to stand on her toes to release some of the pleasure. Rachel looked lovely, on her toes, her breasts pulled up by her nipples, a grimace on her face from the pain Michael was inflicting on her breasts.

Michael suddenly released her nipples, her breasts falling back down, her feet back flat on the floor. He sat back down. “Raise your skirt above your waist. I want to see your panties. Spread your legs further open.” Rachel reached down to the hem of her skirt and began to slip it up her thighs. Michael watched as she slowly bared her legs to him, his face only inches from them. Rachel pulled her skirt until her panties were completely uncovered, her legs spread wide. A wisp of pussy hair pulled out from the edge of her panties.

“Drop your skirt to the floor, quickly now. Keep your legs together. Now slowly pull your panties down to your knees for me.”

Rachel dropped the skirt and as her panties began the descent of her legs, she watched Michael’s eyes as they ravished her body. His eyes watching as her pussy was first bared to him. “Drop them to the floor.” Rachel pushing them all the way down and stepping out of them. She began to spread her legs out, her pussy opening for him. “You’re learning, it will go much easier if you learn to please me.” Her legs were now spread over three feet. “More, I want your pussy spread for me”. When they were over four feet wide, Rachel stopped. She stood tall, her breasts thrust out, her legs spread wide, her pussy opening to the cool air.

“Turn and bend over with your legs spread. I want to see your asshole.” Rachel flushed with embarrassment, turned, her back to Michael and began to bend over. She did not expect that it would be this humiliating. She began to bend over. “Reach back with your hands and spread your cheeks apart. I want to see that tiny asshole.”

Cringing in humiliation, Rachel did as she was ordered. Her cheeks spread open, the cool air blowing on her asshole.

“Beautiful, Rachel, now turn again and face me and assume the position.” Rachel did as she was told, breasts pushed out, legs spread, her pussy opening. “Spread your pussy lips open so I may see your pink insides.” Rachel complied, her fingers grasping her pussy lips, spreading them open. She realized that Michael could see the pussy juice on her pussy. “You are enjoying this, aren’t you. You are wet.”

“No, you are making me do this. I don’t want to do it, you are humiliating me,” tears running down her cheeks. Michael could see that she was aroused. She did not want him to know this.

Michael got up and came over to her with a camera in his hand.

“No, don’t take pictures of me like this. I don’t want to become part of your scrapbook.”

“All of my charges get into my scrapbook. Your pictures will be used to train the next young lady.” He began to take pictures of Rachel. He took a close up of her spread pussy. He went behind her and got a nice picture of her tiny anus.

There is one matter to finish before you may leave. You failed to obey one of my commands and you displeased me. You must learn to never do that again. I want you to lie over my lap, your head down on the floor. I am going to give you a spanking on your bare ass.

Tears began to fall from Rachel’s eyes. Besides disappointing Michael, she was also going to have to suffer the humiliation of getting a spanking. It would be just like she was a little girl of twelve again. She moved over Michael and spread her body over his legs. She could feel his hard cock resting against her stomach. Her head hung down, waiting in suspense. She could feel one of his hands run over her naked cheeks. Fingers pushed between her legs. “Open your legs, you must stay open for me at all times.” Her legs parted, giving Michael access to the most intimate portion
of her body. He fingers again moved between her legs, running over her wet pussy and pushing back
toward her tiny anus. His wet fingers moved over her anus, sending shivers through her body.

His hand was removed and suddenly a loud smack filled the room, seconds later the pain registering with Rachel. His hand had hit her left cheek very hard. “OOOWWW, I will obey next time, please Sir, don’t hit me again,” she begged.

“It will be twenty five for you young lady, you are lucky it is not more. Now hold still and keep quiet. You must learn to accept your punishment.” His hand began to beat her cheeks, alternating each time. By fifteen, both cheeks were beet red and Rachel was whimpering in pain. By twenty, she had to put her hand in her mouth to stop the screams. Finally she received the full twenty-five. He pushed her upright, a gasp coming from her lips as he grabbed her beaten cheek.

“You may get dressed down and return to your room. I am finished for the day. I do not want you to masturbate tonight. Tomorrow, Stephen will be here for your inspection. If you think today was bad, tomorrow will be even worse.”

Rachel grabbed her clothes quickly and began to put them on, the embarrassment beginning again, as she is now forced to dress in front of him. She quickly finished. “Thank you sir, ” and ran out the door.

(To be continued)

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No Responses to “Boarding School Sex Training”

  1. osacero says:

    To the author{s}:
    You have a nice style, and I can see that you’re going for something slightly Victorian. I hope you won’t be offended if I say that a spell-checker does not adequately replace an editor. For instance, when Rachel is shown the pictures of Sara, you tell of her vagina (if I remember correctly) “peaking” out. Didn’t you mean “peeking”? The spell-checker only looks for an English word, so does not distinguish between the one and the other. If you or some one else will just read your stories carefully, correcting grammer and spelling, I think it would go a long ways towards making them A-One material, as opposed to B-Two. Also, if I may be so bold, please give a little thought to your use of adjectives and adverbs. When Rachel first enters the Headmaster’s room, you say something to the effect of “as usual, she was amazed at the grandeur”. One is not amazed, usually, “as usual”. The term implies surprise. And would splendor be more appropriate?
    I hope, as I said, that you do not take offense at my criticism. Had I not been impressed with the basic power of your story, I would not bother to comment.
    Sincerely,
    Osacero

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  2. KillerBee says:

    Very good plot, can’t wait for the next installment!

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  3. Rachel says:

    that was very wrong quite sick in fact!

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  4. becca says:

    great stroy hurry up and putin the next installment

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  5. Vee says:

    this is a great series, excellently written. I look forward to reading more of your stories..

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