Boarding School Sex Training-Chapter 6

Michael moved closer to Rachel’s ass, his hands slowly running over her flesh. He molded her flesh, watching as it turned red when he pinched it hard. He reached over to the drawer and pulled out a jar of Vaseline. He saw the expression on Rachel’s face as she heard the sound of the jar being opened. “Relax, Rachel, I just want to feel that hot asshole.” 

Rachel heard the sound of the jar opening and knew what it meant. Michael was going to grease up her asshole so he could slip his fingers up her. Jason would be watching her suffer the degrading act. She cringed, but kept her ass cheeks spread open as she felt the cold Vaseline being rubbed on her exposed anus by Michael’s thick finger. She felt the finger stiffen on her anus and the pressure began, forcing it slowly open, the finger pushing slowly and painfully in her. “OH, God, please don’t do that, it feels strange and it hurts,” Rachel begging as she felt her anus being forced open.

“Relax, little girl, loosen up your asshole, let my finger in. Jason wants to see your asshole wrapped tightly around my finger. Now relax your asshole,” his other hand slapping hard on her left cheek, leaving it a bright pink.

“OOOwww,” she cried, the spank on her ass hurting. She tried to relax her sphincter, but it was difficult. Only once before had they fingered her. Her asshole was used to pushing things out, not in and felt strange. She felt the finger pushing harder and her ass suddenly allowed it in, spreading wide, the pain spreading quickly to her brain. “AAAGGGHH, please, not so hard, it hurts.

Michael stroked her ass as his finger entered her sphincter. It grabbed tightly onto it, gripping it. “That’s a good girl, your asshole is so tight and hot. I’m going to slip it deeper into you, so take a deep breath.” He moved his other hand around to her pussy and two fingers reached for her clit. He grabbed it tightly and pinched hard. He felt her jerk back away from the fingers, pushing her asshole further back onto the finger barely in her asshole. Michael’s finger entered up to the first knuckle.

Rachel screamed in pain as her clit was pinched and then she brutally pushed her asshole back onto the finger embedded in her to escape the pain, only to further impale her anal tract on the finger, swallowing it up to the first joint. She heard Michael’s voice order her again to impale herself on the floor as the other fingers pinched her clit hard again, her scream of pain only making his cock harder. She again jerked back in response, this time the fat finger pushed up to the knuckle, her anus straining tightly around it. She tried to pull off of the finger, but it again brutalized her clit, her hips jerking back again, her anal tract now fully embedded with Michael’s finger. 

“Boy, is her asshole full of finger now,” Jason joked, watching as Rachel was further humiliated, standing with her back to them, her asshole stretched tightly around Michael’s finger. She still held her cheeks apart submissively to her degradation. 

Michael’s other fingers let her clit loose and grabbed a bunch of her pussy hair and began to pull it out, forcing Rachel to pull her hips forward, this time pulling her asshole off of the finger. Michael watched as her asshole slowly pulled over his finger as it was pulled out. When it was almost all the way out, his fingers returned to her clit again, pinching hard, this time forcing Rachel all the way down on the finger again until it was deep in her anal tract.

“AAAGGGHH, no, that hurts,” Rachel’s hips jerking back and forth, her anus speared repeatedly on Michael’s finger. First her clit was pinched brutally, her hips shoving hard back on the finger, pushing it deep inside her. Than her pussy hair was pulled, forcing her off the finger, getting her ready to impale herself on the finger. “Not again,” she cried, but Michael ignored her pleas and squeezed her clit again, her anal tract again forced open brutally by the fat finger.

Michael let Rachel relax, his finger fully embedded in her anal tract. He felt her sphincter tugging on his finger, unable to control the feeling of being impaled. “Tighten your asshole on my finger, Rachel. Let me see how tight you can make your asshole,” he ordered her. He heard her whimper, but did as she was ordered. Michael felt her asshole tighten on the finger. “Yes, that’s good, again Rachel.” He felt her tighten again. “Soon, I will be sticking my cock up your asshole and I will make you grip it with your asshole until I cum deep inside you. It is going to hurt when I fuck you, but Stephen likes to fuck assholes so you will have to learn to like it.” He moved his fingers around inside her, making her feel the fat finger filling her anal tract. Michael pulled his finger out of her asshole with a pop. He slapped her ass hard. “It’s time for you to learn to suck cock, first mine, than you are going to suck Jason’s cock. On your knees, its time for your lesson.”

Michael positioned Rachel on her knees in front of him. Her face was level with his crotch and Rachel could see his hard cock straining his pants. “Open my pants up and pull them down, I want you to get acquainted with my cock.” Michael looked down as Rachel’s hands moved to his belt, un-buckling it. The snap was next. “Pull my zipper down with your teeth,” he ordered her. He looked at her innocent face as she moved forward, her nose bumping against his hard cock as she twisted her face in order to grip the zipper with her teeth. She bit tightly down on the zipper and began to pull it to the floor, her head moving down, her cheek brushing against his cock. The zipper moved to the bottom, his pants opening.

Rachel brushed against the hard cock as she submissively lowered his zipper with her teeth until she could see his cock only restrained by shorts. Her hands moved to lower his pants to the floor and watched as Michael kicked them away, standing only in his shorts. Michael’s hands gripped her head and pushed her into his shorts, rubbing her face over his erect cock. She could feel it jump in excitement as her mouth and face was rubbed against it. She knew it would soon be naked and pushed into her mouth.

“Now the shorts,” he ordered her and watched as she gradually lowered his shorts, his cock popping out suddenly, slapping against her face. She moved her head back in shock as the hot cock hit her. She pulled his shorts to the floor and looked back up. His cock was over eight inches in length and over two inches in diameter. The head was red and swollen and some pre-cum had already formed on the head. His balls hung heavily below his cock, filled with the hot cum he would soon deposit in her youthful and inexperienced mouth. “Look at my cock.” He gripped her head again and ran his cock over her face, feeling her cringe away at first when she felt the hot tool rubbing over her face. He saw some precum leak out of his cock and he rubbed it over her lips as he felt her hot breath on his cock. He looked down at her, her eyes bright and innocent, his cock resting against her lips, his cum glistening like lip-gloss. “Kiss my cock.”

Rachel felt the cum on her lips and knew she would soon have to take it into her mouth. She heard his command and her lips tentatively reached out and brushed against his cock. She puckered her lips and kissed his cock again. She had to hold his cock to keep it from jerking about as her hot breath and lips sent it into spasms of pleasure. 

“Lick it with your tongue, Rachel, taste my cock with your sweet tongue.”

Rachel pushed her tongue out, gripped his cock tightly and ran her rough tongue over the head of his cock. She could taste the first of the cum, thick, hot and salty. She did not like the taste, but she knew that did not matter. Michael would force her to drink his cum anyway. His cock twitched in pleasure as her tongue began to bathe his cock with her saliva. She licked over the large head of his cock, her tongue running over the piss slit, more precum leaking out from her oral manipulation of his cock. 

“You are very good, Rachel now put my cock inside your hot mouth. Use your tongue on it when it is inside. Tighten your lips around it and suck it like a lollypop.”

The time had come, he wanted his cock inside her virgin mouth. She slowly opened her mouth, grabbed his cock at the base and slowly let it enter her mouth. As it began to slide in, she closed her lips over the head and let her wet lips moisten it with her saliva. It felt so hot and hard. She ran her tongue over the head and could taste his cum. It felt thick on her tongue and was salty. She knew that when he came, it would fill her mouth with a large amount, she did not know if I would be able to swallow all of it, but she knew Michael would force her to. She hesitantly let the hard cock push further into her mouth, her tongue running over the head as she did. She could feel it twitch in her mouth, knowing that she was pleasing Michael.