Boarding School Sex Training-Chapter 8

(Part 4 from 8)

Stephen held her open wide showing their guests all of her and making her purse her asshole for what seemed like an eternity. She thought the ultimate humiliation was when he fingered her pussy hole to retrieve some juice and spread it on her asshole to insert his finger deeply stroking the inner walls of her ass. “Now squeeze and release your asshole onto my finger. Show everyone how you are going to do it when a cock is forced up your asshole.” He then inserted two fingers, and finally three for her little pucker to suck for them. 

Rachel felt invaded and used as his fingers pummeled her asshole. She could hear the men in the room beginning to pant and grunt a bit as if to cheer her little star on to squeeze harder, to suck harder, to spread and pulsate for them. She continued to grab and release the thick fingers as they continued her anal ravishment, sliding noisily in and out of her clenching asshole.

Deena sat frozen, afraid to breath, the action was so intense before her. Her cunt dripping, wiping the perspiration, trying to breathe evenly, she knew she was going to cum in her seat. How she would have loved to be the giver or the recipient of such administered lust on Rachel. Watching Rachel's little pucker wink and dance made Deena clench hers repeatedly where she sat.

Rachel took the fingers over and over as her asshole gripped them. She was being spread wider and wider in preparation for something bigger to be inserted into her for her little pink, ripe rectum to suck.

“Very good, Rachel, but it is time for me to fuck you. My cock is so hard watching you,” Stephens hand reaching down, stroking his hard cock. He had already stripped off his clothes, ready for Rachel. “First, we need to get your asshole lubricated. It is so tiny, I am going to need something to help lubricate the path for my cock. Deena, would you mind helping me?”

Deena immediately stood up and almost tripped moving so fast to the table. Poor Justin was left, his cock hard and no one to continue the masturbation. “Oh, yes, I would love to help,” shouting with glee at the chance to play with poor Rachel. “What can I do?”

“I need you to open up Rachel’s asshole with your fingers so I may pour some baby oil inside. Then you can finger her asshole and lubricate it deep inside of her. Would you like that, Deena?” Stephen smiled, knowing that Deena would not miss a chance to do anything with Rachel. He would have to invite Deena and Justin to one of his parties, Deena would be fun to play with. He handed her the bottle of baby oil. “Pour some on your fingers, then I want you to start with one finger, add a second and finally a third finger in her asshole. When you get her asshole spread open, I will pour the baby oil in.”


“Oh, yes, Sir, I can do that, I can do that real good.” Deena grabbed the bottle of oil and poured some into her palm and began to move it around her fingers until they glistened in the light. She reached over to the globes of Rachel’s ass and softly moved her fingers over it, moving towards the crack where Rachel’s asshole was nestled. “Just relax, Rachel, I will get you ready.”

Rachel shivered in fear and anticipation. Deena was touching her again. She was afraid of her and at the same time she seemed to enjoy it when she touched her last time. She knew that she shouldn’t have these feelings, she was not a lesbian, but her hands were so soft and reassuring compared to the hands of the men, always quickly grabbing and her pinching her intimate flesh.

Stephen watched as Deena ran some baby oil over Rachel’s ass and massaged it into her cheeks, each time pulling outward on them until her asshole was exposed to her gaze. 

“That’s a good girl, Rachel,” her fingers moving closer and closer to the exposed asshole until they finally ran teasingly along the edges, watching as Rachel’s hips rose slowly up into the air. “Yes, I knew you would like that,” the fingers pushing harder onto the tiny rosebud, a light brown, contrasted against the pale skin of her naked ass cheeks. Her fingers circled it, each time she would push with her finger as it ran over the opening, lubricating the portal. Two of Deena’s fingers were now rubbing on it, massaging the oil into it, preparing for entrance. Deena pushed with one finger and watched as her asshole began to spread open, grabbing her finger tightly. She pushed harder, going in up to the first joint, feeling Rachel’s sphincter grabbing it. She twisted it, watching Rachel arch her ass up, forcing more of her finger into her asshole, it now embedded up to the knuckles. “Tighten on it like you did for Stephen,” she ordered Rachel. She felt her finger grasped so firmly. “Yes, such a tight asshole, Rachel. Now two fingers,” pulling one finger out and replacing it with two fingers, sliding effortlessly into Rachel’s back passage. “Tighten again, yes, so good,” her fingers twisting back and forth inside her asshole. “You can take three, push back on my fingers,” two fingers pulled out and then Deena plunged in with three fingers, twisting and turning them as they plowed up Rachel’s asshole.

Rachel moaned as Deena continued to finger her asshole, lubricating it with baby oil as she plundered her back passage. She tightened on the fingers, as ordered, feeling them pulling slowly out, the knuckles rubbing tightly against her insides. The three fingers hurt as they entered her, her asshole straining to accept the fingers, the knuckles pushing harshly against her sphincter as they plunged in. “OOOW,” she cried, her ass arching up, unable to escape the painful tearing of her asshole.

Deena pushed her three fingers into Rachel’s asshole, feeling her sphincter muscle gripping them tightly. She saw her anus stretched tightly over them, the pink skin now almost white as it was pulled wide, gripping the fingers. 

“AAAGGGHH,” Rachel wailed as the fingers began to spread open inside her, her silky insides forced open as her anus was stretched to the limit. She could feel the cool air inside her asshole, knowing that they could now see inside her, her tiny star of a rectum now a gaping hole for everyone to see. She felt a cold liquid slowly run inside her asshole as Stephen began to pour the baby oil inside her gaping hole. The liquid stopped and the fingering of Deena began again. This time the three fingers slid along her back passage effortlessly, gliding on the baby oil as they plunged in deep inside her rectum. She blushed again as the fingers noisily plunged in and out her asshole.

“Thank you, Deena, why don’t you go back and suck Justin’s cock for him. He seems so lonesome over their, stroking his own cock.” Stephen pushed down on Rachel’s ass, forcing her back down onto the plush. “Spread your legs wide again, it’s time to get ass fucked, Rachel.”

Rachel spread her legs until she reached the edge of the table. Her ass glistened in the light, her ass coated in the faint sheen of the baby oil. She felt Stephen climb onto the table between her legs and she groaned in pain as his knees pushed out onto her thighs, forcing her legs open even more. It felt like he was going to split her up the middle. She felt his oil fingers rubbing up and down her thighs, moving close, but not touching her pussy. She felt something new, not his fingers but the head of a cock rubbing along her inner thighs. It felt huge, afraid of how much it would hurt as he fucked her with that monster.

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