First Day at Boarding School

“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 come 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.

“Come for me Rebecca, come 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 sixteen-year old now naked and spread over a chair. She felt hands grab her ankles and ties 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 also directly on her anus. After twenty-five spanks he stopped.

“Stay very still as I am going to pleasure myself with your asshole”. 

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”.