Boarding School Sex Training-Chapter 3

Rachel cringed in pain as the finger scratched along her anal tract. Her asshole tightened as a reflex to the finger. He wanted her to do it again. The finger scratched her again. She tightened on the finger, anything to stop the cruel finger in her ass.

“You’re asshole is going to be a great fuck with a little training, Rachel. Lets spread it open and see inside.” Michael picked up the smaller speculum and greased it up. 

Rachel tightened up her asshole as felt the greased speculum run over her anus. Michael paused a second before beginning to push it into her anus, stretching it open. She felt her anus open more than it ever had to before, it felt like it was going to tear. “OOOOWWWW, no deeperrrr,” she cried. Michael continued to push it into her anus, now entering her rectum, forcing it to open. It stretched her open, relentless, as it continued to push in.

Michael released the speculum, now held tightly in her asshole. Stephen watched as Rachel’s asshole clung tightly to the speculum. He reached down and began to open it slowly, watching as her anus was forced to open even wider. “Relax your asshole and it will be less painful, you must learn,” he ordered her.

“OOOHHH, tttoooo wiiiddeee,” she cried, “please take it out, OOOOWWWW.” She could feel her anus stretching wider and wider, and deeper inside her rectum, the speculum opening her anal tract. She was finally allowed to catch her breath, the speculum now fully opened inside her. She could feel the cool air in the room blowing inside her exposed asshole.

Michael produced the small light and they both peered into her exposed and opened anus. “You will soon feel what it is like to have a large cock pushed into your asshole, Rachel. Than I will enjoy the delicious feeling of it fucking your hot and tight asshole until I cum deep into your colon, flooding it with my hot cum.”

Stephen released the speculum and slowly pulled it from Rachel’s asshole. He watched as her anus grasped it tightly as it was pulled from her, as if it did not want it to leave.

The speculum pulling from her asshole felt strange to Rachel. Her anus clung to it tightly and the suction as it pulled from her body left her feeling empty were she was previously full. She wondered what it would feel like when Michael pushed his cock into her asshole and would fuck her. She was beginning to get wet again. 

She felt Stephen release her wrists from the straps. She rubbed her wrists, the circulation beginning to return. Her legs were still tied tightly to the stirrups. “Are you going to release my legs?”

“Not yet, I want you to masturbate for us until you cum. Keep your eyes open and stare at us. We want to see you pleasure yourself,” Michael stated.

They intended to degrade her further, forcing her to masturbate in front of them until she had an orgasm. It would be humiliating, playing with herself. While she regularly masturbated, it would be extremely embarrassing to do it in front of others.

“Now, begin now,” Stephens voice booming the order.

Rachel moved her hand down to her vagina and began to peel back her pussy lips, stroking her pussy slit. She could feel her wetness, the excitement of having to exhibit herself to them increasing her pleasure. She ran her other finger over clit, her eyes staring at Stephen. She could see him gazing down at her exposed vagina, her fingers busily masturbating herself to a climax. Her fingers moved faster, a groan of pleasure escaping from her lips.

“Put a finger in your asshole before you cum,” Michael ordered.

She cringed from the statement, but she obeyed. Her finger reached down between her legs and searched out her anus. Her finger found it and began to push in, her anus still slick from the speculum. She again felt the feeling of her rectum being opened, this time it was her own finger. Her other fingers were continuing to masturbate her hard and erect clit. Another finger found her pussy and pushed inside. She continued to fuck her pussy and asshole with her own fingers, Michael and Stephen watching her body toss about on the table, her legs still tied open. 

“Cum for us, Rachel, it is time to cum for us,” Michael’s voice breaking her concentration.

She speeded up the finger fucking of her pussy and asshole. They had ordered her to cum and she was determined to obey. “OOOH, GGGoooddd, I cuuummmiiinnngg,” she cried, her eyes watching as her new Masters watched her cum for them. She pushed her fingers in her pussy and asshole deep and a second cum overtook her body, her pussy and asshole tightening down on the fingers deep in her body. “AAAGGGGaaaiiin, OOOH GGggODDD, I’m cumming again,” her body jerking on the table, the eyes watching as she had a second powerful orgasm. She finally sighed relief, her orgasms over her body.

Stephen removed the straps holding her legs to the stirrups. Rachel closed her legs, her fingers still trapped in her pussy and turned onto her side.

“Stephen has to leave now, but he will return during your training to see how you are progressing and to samples the delights your body has to offer. I want to see you in my office at three O’clock tomorrow to begin your training. You will learn how to masturbate my cock tomorrow and make me cum. I want you to move to the room next to my office. That way I will have access to your body at any time of the day and night. You may now get dressed and leave. I will see you tomorrow.” Michael left the room with Stephen, leaving Rachel go get off the table and get dressed. 

To Be Continued...