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First Day at Boarding School Chapter 1

Author: Powerone
Category: Erotic_Straight_Stories
Last updated: Sep 20, 2007

Rated 6.0 with 171728 ratings
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Page 1 of 2



Rebecca was sent to boarding school when her Mother married again. Her new Stepfather did not seem to like her around and arranged for her to be sent to the new school. Her Mother was reluctant at first, but he convinced her that it was a well-known and established school and that it would be good for Rebecca to go there.

Rebecca was uncomfortable on the trip to the school as her Mother did not go, just her stepfather. They barely spoke a word during the 2-hour ride. When they arrived, Rebecca was surprised, they school did not look anything like it was described to her Mother.

“What kind of school is this”, she asked.

“This is a special school that will train you. The Headmaster is a very good friend of mine and he has promised to take a personal interest in your training. He has invited me back in a week to see how you have progressed”.

Reluctantly Rebecca got out of the car and entered the school. She figured once her Stepfather was gone, she could call her Mother to pick her up and take her home.

Her stepfather knocked on the door. The Headmaster opened the door and invited Rebecca in. “Thanks for bringing her Jim, I will see you next week and I am sure you will be please with Rebecca’s progress” he said to her Stepfather.

He did not speak until her Stepfather was gone. He closed the door and said, “I am Headmaster Johnson, you will call me Sir. Sit in that chair,” pointing to a wooden straight back chair”.

Rebecca began to protest when he slapped her face. Rebecca brought her hands up to protect herself. “Leave me alone, or I will tell my Mother”.

“Your Stepfather gave me permission to use whatever force I need to get you to obey. We believe in corporal punishment at this school and if you fail to obey any orders or commands, you will be spanked or whipped.” His hand reached out again, slapping her face again.

Tears began to run down Rebecca’s cheeks as her cheek stung from the slaps and she feared what her Stepfather had gotten her into.

“Now sit down, or face more punishment”, he commanded.

Rebecca hurriedly sat in the chair fearing more pain. Rebecca was eighteen years old but she had the body of a mature woman. Her breasts were large for her age, but without a hint of sag. She had long legs and a firm ass. The Headmaster glared at Rebecca. He could imagine her stripped and tied, awaiting his punishment of her innocent body. He had promised Jim that by next week, Rebecca would be submissive and would allow him to pleasure himself sexually with her.

“Sit up straight in the chair, feet firmly on the floor, knees together and your arms on the armrest”, he ordered. Rebecca quickly followed his commands, fearing him.

“You must obey every order I give you without hesitation. If you do not, I will punish you. As you have already seen, you will suffer pain for your disobedience. I have taught many young ladies like you obedience. At your young age, I find that humiliation works best to instill the correct attitude. You will be forced to do things that you thought was disgusting. If you make any attempt to resist, you will be dealt with harshly. Do you understand?”

“Yes” murmured Rebecca, fear gripping her.

The hand reached out again, slapping her face. “I told you to address me as Sir”.

“Yes, Sir” shot back Rebecca.

“That is better. Now lets get a look at what we have to work with this week. You are a very attractive girl, Rebecca. Raise your arms above your head and lace your fingers behind your head and keep your back straight.

Rebecca did as she was told, and began to fear what was to become of her as she noticed that the pose he put her in pushed her breasts out.

“Very good, you have very large breasts for a girl of your young age. Now open your legs to the edge of the chair”.

Reluctantly did as she was told, knowing that he now could now see up her skirt.

“Nice legs, open them further so I may see your panties”.

Rebecca spread her legs further, turning red in humiliation as she was now posed with her breasts out and her legs spread wide. She hoped he would soon be finished and she could get out of his office.



“You are doing a good job obeying to my commands. You are going to spend the next couple of hours in this office. I am going to train you to obey all of my commands. In addition, I will administer a spanking, as you will have to learn to accept the pain. If you follow my orders I will allow you to go to your room for the night, but tomorrow morning we will again meet for further training”

“Please don’t spank me, I am too big for that and you are embarrassing me”.

His hand shot out again, slapping her face. Tears began to fall from her eyes, as she knew that there were worse things to come.

“Now, where were we, before I was rudely interrupted with your begging. Yes, I think it would be much better if you unbuttoned your blouse and pulled it from your shoulders. You have lovely breasts and I would like to see your bra now”.


Rebecca’s hands moved to the front of her blouse and began to unbutton each button. By time she reached the bottom, he could see her cleavage.

“Open it wide and push it off your shoulders, arms behind your head and push your breasts out again”.

Rebecca sat in the chair, pushing her bra-encased breasts out for him to see. She saw him pull a chair in front of her and sit on it, only inches from her. His hands moved to her shoulders and began to move down to circle the top of her breasts.

“Hold very still and do not move”. Rebecca froze as her hands grasped her bra and squeezed her breasts. She gasped as a stranger began to manipulate her breasts against her will, but she was frozen in terror of the consequences of disobeying. His fingers became more insistent, searching out her nipples.

“Stand up and remove your blouse and than your bra. I want you to bare your breasts to me. Obey quickly”.

Rebecca stood up in a daze and let her blouse drop to the floor. She reached behind her bra and unsnapped it. She pulled it forward and it too fell to the floor. Rebecca had never let anyone see her naked breasts before, and here she was now stripped naked to the waist in front of a stranger.

“Back in the chair and stick your breasts out again”. His hands moved back to her breasts and now began to fondle her naked breasts. He pulled on her nipples, stretching them out. He grasped a handful of naked tit and squeezed it tight. Rebecca trembled in fear as she submitted to the fondling of her breasts. Her nipples began to become erect from the unnatural stimulation. This allowed the Headmaster to grip them tighter, forcing a groan of pain from Rebecca.

“Up again and remove your skirt and panties. Leave your shoes and socks on.

Rebecca stood up again and unsnapped her skirt and let it fall to the floor, leaving her with only her panties hiding her nakedness.

“Quickly, we do not have much time, off with your panties”.

She grasped her panties and pushed them down her legs, showing her naked pussy for the first time.

“Step out of your panties and move forward. Put your legs outside of my legs and spread them open”.

Rebecca did as she was ordered and now stood naked only inches from this stranger; her legs spread open and her pussy only inches from his face.

He moved his hands up her legs, toward her naked pussy.

“You have a lovely pussy, Rebecca. How do you like showing it to a stranger?”

“Please let me go, I am so humiliated to be stripped naked in front of a stranger”.

“You will get used to it. By next week, you will be forced to strip naked in front of many strangers. When your Stepfather comes next week, you will willingly undress in front of him and allow him access to all parts of your body.”

His hands reached her pussy and began to run up and down between her pussy lips. He fingers reached her clit and began to circle it, eliciting a moan from Rebecca. His other hand reached behind her and grasped her naked ass.

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