First Day At Boarding School

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 pleased 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.

"You have a nice ass, Rebecca." His hand grasped her cheeks and began to move toward the crack in her ass. "Stand perfectly still and submit to me. I am going to make you cum on my fingers."

His fingers began to move into her opened pussy. One finger was pushed into her and as she moved back to escape the ravishment of her pussy, his other hand found her anus. The finger pushed against her virgin anus, forcing Rebecca to again move forward, pushing the finger deeper into her pussy. Rebecca began to move back and forth from the twin ravishment of her pussy and anus, each time pushing his fingers deeper into her body. Soon he had both fingers buried deep into her pussy and rectum.

Rebecca could just barely stand, naked with his fingers buried deep into her body spreading her open to his touch. He began to fuck them in and out of her pussy and rectum, with a second finger joining the other, opening her up. They began to spread inside her, forcing her to her toes to escape the cruel ravishment of her twin orifices.

"Cum for me Rebecca, cum on my fingers." His fingers became more insistent, forcing her pussy and rectum open. Her body began to rock back and forth, her inexperienced body reacting to the forced stripping and finger fucking of her body.

"AAAAAHHH," she cried, "OOOOGGGHHH, it feels so strange, what are you doing to me," she cried, her orgasm overcoming all other emotions. Rebecca finally calmed down, her legs just barely holding her up. His fingers in her pussy and rectum were holding her up.

"Now that you have felt the pleasure, you must now receive the pain." He pushed Rebecca over to a large overstuffed chair. "Lean over the chair and push you head into the seat and push your ass out."

Rebecca did as she was told, the eighteen-year old now naked and spread over a chair. She felt hands grab her ankles and tie them to the edge of the chair, spreading her legs wide. She could feel the cool breeze on her anus and knew that she was exposed.

"Do not move your hands, I am going to spank your ass. You must feel the pain after you receive the pleasure." His hand slapped hard onto her right cheek, forcing a groan of pain from Rebecca. The hand again swung down, this time hitting her left cheek. His hand massaged her cheeks, feeling the hot glow from the spanking. His hand moved away and she knew that she was about to receive another spanking.

His hand again spanked each cheek before returning to caress her cheeks. This time they spread her ass open wide, allowing him access to her anus. She felt his fingers run over her anus again, than one hand was gone to return with a resounding spank directly on her anus.

"OOOOOWWW, that hurts," she cried. The spanking continued, alternating between her ass cheeks and directly on her anus. After twenty-five spanks he stopped.

"Stay very still as I am going to pleasure myself in your ass."

Rebecca could hear his zipper being pulled down and felt him as he pushed his hard cock against her ass.

"I am going to push my cock into your ass. It will hurt, but you will get used to it. You must accept the pain."

His cock pushed against her anus and began to push it open. Rebecca groaned in pain as her anus was forced to open and accept the head of his cock into her ass. "OOOOWWW," she cried as his cock began to force its way into her tender body. The head of his cock was now in her, spreading her open. He began to pull it out and than back in, each time pushing deeper into her rectum. Soon he had two inches, than three, than five and now he had all eight inches buried deep into her rectum.

Rebecca gasped in pain as he flexed his cock deep into her body. It began to give her cramps when he was deep in her. He pulled his cock from her body, the retreat of his cock almost as painful as when he entered her. Once her stretched anus gripped the head of his cock, he forced it deep into her rectum with a single thrust that knocked the air from her lungs.

Rebecca raised her head to scream in pain and tried to push her body away from the awful rape of her ass, but only allowed him greater access to her defenseless anus. He pounded his cock in and out of her stretched anal track, forcing groans and gasps from Rebecca as she was forced accept the brutal rape by his cock.

Rebecca was constantly rocked with the deep thrusts of his cock deep into her rectum. Her sphincter gave up the fight and relaxed to accept his hard cock. Her anal track began to spasm from the pain of the deep thrusts, milking his cock as he continued to tear her insides.

His hand reached over the chair and grabbed her breasts and began to pinch her nipples. His other hand reached between her legs and began to fondle her pussy again, forcing her to push her ass out to receive the pounding in her rectum.

"I'm going to make you cum again, this time with a cock up your ass." His hand moved up and down her pussy lips and massaged her clit, forcing groans of pleasure mixed with the pain of the rape of her ass. Just as Rebecca began to have another orgasm, the cock in her ass pushed deep into her rectum and began to shoot hot cum deep in her ass. Her orgasm milked the cum from his cock, deep into her ravaged rectum.

The Headmaster pulled his cock from her ass and untied her legs from the chair. Rebecca slumped in the chair, exhausted from cumming twice and being raped and spanked.

"You can go to your room now and clean up and get some rest. I will bring you back down here tomorrow and we will continue with your training. I will pleasure myself in your mouth and your pussy and you will enjoy both the pleasure and pain."