Boarding School Sex Training-Chapter 3

(Part 2 from 3)

Rachel could feel Michael’s fingers move up until he reached her pussy. He grasped her pussy lips and began to spread them open wider. Rachel could feel the cool air brush over her wet pussy. Michael pulled them open wider, it starting to hurt as he spread them too wide. Rachel did not say anything, just moaning in pain. She knew that it would do no good to complain. She had already been told that she would have to service their every whim, whether pain or pleasure.

“Rachel will service you well, Stephen. Look how she lubricates with very little stimulation. Masturbate her.” Stephen began to run his fingers between her spread pussy lips, Michael holding her open for him. His finger moved from the bottom of her slit until he reached her clit. He pulled back her clit hood and grasped her clit. It was already hard and erect. 

Rachel’s body shook as Stephen rubbed her clit. She could feel her pussy juice begin to run down her thigh. “Oh God, please,” she cried as her body began to betray her. She could feel the hands down below, holding her lips open and openly masturbating her while she was bound and spread.

Stephen’s fingers began to get soaked in Rachel’s pussy juice as one finger continued to pinch and pull at her clit. It was now pea-size, hard and erect. His other finger was pushing along her slit, all the way down, gently rubbing over her pussy opening, circling it with his finger, beginning to open her. 

Rachel tried to push her pussy up, trying to reach the fingers that were masturbating her. It felt so good, her body searching for an orgasm. She could see Michael and Stephen starting down at her naked body, forcing her to accept the masturbation. “Please, harder, make me cum,” she begged, her hips rising higher.

Stephen suddenly pulled his fingers from her body and Michael released her pussy lips. “Not yet, Rachel, but soon,” Michael said, “soon.” Michael picked up the speculum on the table. “No need for Vaseline, I bet your pussy is soaking wet by now. Help me spread her open, Stephen.”

Rachel again felt fingers on her pussy, relieved, hoping they will make her cum. Her lips were pulled open again and she watched as Michael took the speculum and began to move it toward her spread pussy. She felt the cold instrument push against her vagina. Her vagina began to spread open, the sterile instrument forcing itself into her, pushing further and further into her spread body. 

Stephen watched as Michael pushed the speculum into her pussy, her body forced to accept the instrument. Rachel gasped in pain as she was forced to open, her body beginning to jerk around on the table, to escape the instrument. “Too big, don’t put it into me, please,” she begged. But Michael continued to push the speculum into her spread pussy.


“Relax, soon you will have bigger things than the speculum in that tight pussy, so you are going to have to learn to take them.” Michael put pressure on the speculum and pushed into Rachel’s pussy, her gasping in pain as it was forcibly pushed into her. With one final push, Michael managed to get the speculum fully into Rachel’s pussy. Michael and Stephen both stared at Rachel’s pussy, now fully grasping the metal speculum sticking out, ready to open her up for their inspection.

Rachel felt so full with the speculum forced into her virgin pussy. While she had lost her hymen, she was still techically a virgin. She had never had a cock in her pussy before, but she knew that would be soon taken from her. She could feel Michael or Stephen lightly tapping at the speculum, the touch magnifying in her stretched vagina. Rachel heard Michael say, “relax, we are going to open the speculum so we may inspect inside your pussy.” She felt fingers opening the speculum, the sides expanding her pussy walls, forcing them open. “OOOOHHH, plllleeeasse, don’t,” the pain beginning to spread as Michael continued to open the speculum. “AAAHH, AAAHHH,” her breathing becoming rapid as the pain in her pussy increased. Rachel gasped as Michael had finally expanded the speculum, her pussy now spread wide.

“Look at that beautiful pussy pulled tightly over the speculum.” Michael shined a light inside her spread pussy, her most intimate region now exposed to the two men. Michael picked up a long Q-tip from the table and inserted it into Rachel’s pussy, forcing it deep until it pushed against her cervix. He began to rub it around inside her pussy and could feel her body begin to react to the strange sensation.

They were beginning to torment her again. Rachel could feel something soft rubbing inside her vagina. It felt good. Her hips began to rotate, hoping to intensify the feeling. She still needed to cum, badly. 

“I see our little whore is getting wet again. We will let you cum, but not until we open up your asshole.” Michael pulled the Q-Tip out of her pussy. He began to close the speculum and heard the sigh of relief from Rachel as his pussy was allowed to shrink back down to size. “She is going to be a great fuck, Stephen, her pussy is so tight it will strangle your cock.” Michael pulled the speculum from her pussy, watching as her pussy gaped over for a minute before shrinking back down to its small size. ‘Raise the stirrups higher, we need better access to her asshole.”

Rachel felt Stephen begin to push the stirrups higher, her ass rising from the table. She knew that her anus was now visible, her ass cheeks already spread from the position she was bound in. Her anus was defenseless, ready but not willing to accept the speculum that they intended to force into her asshole. She had never had anything bigger than a thermometer in her anus, but she knew that the speculum was going to open her bigger than anything that had ever pushed out her anus.

“Look at that tiny anus. I am going to have to stretch her open gradually before she will be able to accept my cock. I think we will start with a small butt plug and every other day I will increase the size. I will force her to wear it all night. By time she is ready for you I will have taught her the proper way to fuck you with her asshole. She will squeeze your cock to a great orgasm.”

Rachel could not believe what she was hearing. Michael was talking about forcing her to put wear a butt plug up her bottom every night and teaching her to fuck him with her asshole. It sounded so filthy, putting his penis up her bottom and forcing her to pleasure him until he had an orgasm in her.

The sound of the lid on the Vaseline being opened brought her back to reality. She saw Michael rub some on his index finger and she felt the cold jelly rub against her anus. She shivered in fear as she felt the finger push against her anus. “AAAGGGGHHH,” she yelled as Michael forcefully pushed his finger deep into her anus, going into her rectum and forcing her anal tract open in one forceful plunge.

“Just to show you that everything is not enjoyable.” He pushed his finger in deeper, twisting it in her anal tract. He could feel her tighten on the finger, attempting to escape the cruel ravishment of her asshole. “That’s good, do it again, tighten on my finger,” his finger twisted in her rectum again.

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