Chapter 1 | Chapter 2 | Chapter 3 | Chapter 4 |Chapter 5 | Chapter 6 | Chapter 7 (Below)

​

After several minutes, finally Sir Jackson felt his cock was clean enough to withdraw from Stella’s mouth. She tried to catch her breath and hold herself back from wanting to vomit.

As she slowly tried to refocus herself, she heard Miss Caroline enter behind her. “How was the lesson?”

“She did well,” Sir Jackson responded, “not like there was a choice though.”

Stella was trying to listen but the discomfort from the enema was driving her mad. She could slowly see Miss Caroline walking into her line of sight as she circled her, completely ignoring the girl still bound to the cart who’d just had her asshole brutalized by Sir Jackson.

Miss Caroline slowly withdrew the enema tube from Stella’s hole, watching carefully to see how well she’d hold in the water. “This one must be tight, barely a drop.”

Sir Jackson chuckled as he brought over a bucket. Stella began to stress, knowing what they would be asking her to do next.

She wanted the water out of her insides, but having to release it in front of them was humiliating.

“Release.” Miss Caroline commanded.

Stella closed her eyes and pushed, shooting a stream from her ass. It wasn’t as uncomfortable as she thought, but it was degrading feeling the occasional spurt and solid.

Finally, she’d pushed all she could and felt her stomach beginning to settle down from it all.

“Good girl,” Miss Caroline said, handing the bucket to Sir Jackson for disposal. “Your diet seems to be working well already.”

She slowly massaged Stella’s asshole with a wet hand, sending shivers up her spine and a conflict of pain and pleasure.

Suddenly, something felt off. Stella braced herself as she realized what was happening, Miss Caroline was inserting a butt plug into her.

“I know this is the first one you’ve ever taken #3571, so we’re going to start small.”

Stella was horrified at the bizarre feeling, she wanted something in her pussy, not her ass, but she had no way to control things at this point.

Finally, the plug forced its way in and settled into Stella’s tight hole. She could barely take the small object, let alone the large one or a fucking like the girl in front of her just received.

“Now, you’ve done so good today #3571,” Miss Caroline said, “I think we’ll give you a reward.”

Stella was praying the reward had something to do with her pussy, however at this point she certainly doubted it.

Sir Jackson slowly began pulling the plug from the other girl's hole, sending fear straight to Stella’s mind.

He held up a cup and waited as his cum from earlier slowly began to drip out of her hole into the clear container.

Stella wanted to die. Surely they weren’t going to make her eat this cum that had been marinating in the girl's ass for the last hour.

Finally, the drips slowed and Sir Jackson pressed the plug right back into the girl, again ignoring her comfort completely.

He held the cup of cum up to Stella, “doesn’t that look good, I think we’ll save it for your breakfast though.”

Stella’s eyes began to water. Between the pain and fear she was a mess, she wanted to go home, be safe, return to the small simple town she’d grown up in.

“It’s been a long day,” Miss Caroline interrupted, “let’s send this one back to her cell for the night.”

Stella was shocked as they began undoing her gag and restraints, paying no attention to the plug still in her ass. She cooperated as they hooded her and walked her down the hall, cringing with every step at the new intrusion.

Her hood was released as she sat on the floor in her cell and Sir Jackson looked back at her, “don’t even think about touching that plug.”

Stella couldn’t believe it, not only was she forced to have this bizarre thing in her ass, but now she was going to spend all night with it in.

She tossed and turned for hours, barely able to get to sleep from the discomfort and stress. Finally the lights came up and food service began as usual, telling her the morning had arrived, she’d made it.

Her food was dumped into her bowl and as expected, contained a large load of Sir Jackson’s cum which had been pressed out of the other slaves asshole.

The taste was terrible to Stella, not only did it have the cum flavor, but also was a sour ripe hint of the other slaves insides.

She barely got all the food down before Sir Jackson arrived to pick her up for the day. She was hooded once again and led back to conditioning, where she couldn’t even imagine what torture she’d be subject to this time.

Stella was placed against the wall on a small bench where her arms were attached tightly to brackets behind her, and then each leg lifted and attached as well. She was bound with her ass sticking straight out as she sat back waiting.

Miss Caroline quickly pulled the hood off of Stella, enjoying her shock and concern of the new predicament. Stella could see them both standing there admiring her discomfort and clearly hoping they’d remove the sore plug from her ass soon.

Sir Jackson began wheeling over a few carts and Stella looked up to find a mirror above her.

“I see you’ve found the mirror #3571,” Miss Caroline said, “this position will allow us unrestricted access to inspect and test your hole, while the mirror will allow you to watch every moment of it.”

Stella was shocked and horrified, not only were they going to continue to violate her, but she’d be forced to watch every minute of it.

Miss Caroline slowly leaned in and began withdrawing the plug from Stella’s ass. It hurt as the plug worked its way out, and Miss Caroline certainly wasn’t being as gentle as she could.

They smiled as it came out and admired the cleanliness of the plug. “#3571,” she said, “clean this.” Without warning, Miss Caroline pressed the plug into Stella’s mouth and began swirling it around.

Stella tried not to gag as she couldn’t believe this, she was literally being forced to taste her own ass now. She wasn’t sure what was worse, hers or someone else's.

Sir Jackson smiled at Stella’s disgust, enjoying every minute of it. She was so distracted by the plug in her mouth, she hadn’t even noticed what was happening.

Sir Jackson was working diligently behind Miss Caroline to prepare Stella’s next training stage. He brought over another item, which unfortunately Stella quickly recognized all too well. It was a fucking machine, similar to the one they’d used on her mouth.

As Miss Caroline withdrew the plug, she smiled and addressed Stella, “#3571, it is time to begin your hole conditioning. We will start small, and work your way up each day.”

Stella was horrified, praying that she meant this was going in her pussy. Anything but her ass at this point.

Miss Caroline presented a small dildo in front of Stella’s eyes, slowly turning it back and forth to make sure she could see every inch of it.

“#3571, do you see this dildo?” Miss Caroline asked softly.

“Yes Miss Caroline,” she replied in fear.

“You’re going to begin your hole training now, this is the first of 3 sizes.” Miss Caroline and Sir Jackson were clearly enjoying her fear. “Oh, and by the way,” she mentioned, “we’ve been instructed not to use lube so you better get it nice and wet.”

With that, Miss Caroline shoved the dildo into Stella’s mouth before she could even object. She pumped it around trying to be as rough and degrading as possible.

Stella desperately slobbered on the dildo, trying her best to wet it with her mouth. She was sucking for her life when suddenly, Miss Caroline withdrew it and secured the dildo to the end of the fucking machine.

Stella watched closely as they lined up the machine with her hole, and with the touch of a button, it began slowly forcing its way into her ass.

She shrieked in pain, trying to squirm away from the unwanted intrusion, but her attempts were worthless. She was secured in place while the two just stood there laughing, as Stella watched through the mirror as her anal virginity was forcibly taken from her before anything else.

​

TO BE CONTINUED...