Josh has been having a tough time lately. Well, the whole summer hasn't exactly been a walk in the park for him, and it's been only getting rougher.
Even though he had gotten relatively used to being Vicky's slave and servant and stopped misbehaving or resisting her, she still found ways to push his buttons. Just his obedient submission seemingly not being enough to please her. Relentless demands from Vicky had transformed his once bearable routine into a daily ordeal.
But that wasn't enough for her, Vicky craved more. She suggested that they should 'spice things up'. This involved various pieces of bondage equipment added to his uniform, making his tasks even harder to perform. His legs or arms were chained together with only a few inches between, sometimes both at the same time or a ballgag that caused him to drool all over the things he was supposed to clean. Josh dreaded what she would think of next.
That wasn't the only thing he had to worry about either. Constantly he was being watched, and if any of the girls spotted him slacking off at all, punishment awaited him. Spanking, teasing, having his ass played with, and tight bondage, were just some of the things in the repertoire of torture the girls employed. As if these punishments were somehow supposed to help him.
Of course, with all these increasing demands it was impossible for him to fulfill all of them. So he could look forward to some kind of punishment pretty much every day.
Josh just couldn't keep up. The few hours of sleep he could get were a luxury. He was running on fumes. He already got caught dozing off once when he was supposed to be serving Becka as a footstool.
Her harsh spanking wasn't enough to satisfy Gemma that he had learned his lesson. She took over his punishment from Becka and took off her socks, wrapping them around his face. The smell kept him wide awake for hours.
Keeping his mind clear was another struggle. Multiple times a day he found himself forgetting which chores he had already done, causing him to repeat them. Once he forgot that Gemma doesn't like pickles and added some to her sandwich. She made him eat out her ass again for hours. He nearly suffocated squished between her cheeks.
Due to his unsatisfactory performance, Vicky said that she had to do something drastic. She refused to unlock him during the last weekend. It was already more than a week and a half since he got unlocked. He would be more angry and tormented by this if the lack of sleep didn't dull his mind and in the process his worries as well. Not like he could complain anyway. Any mention of it would just cause him to stay locked even longer.
Due to his unsatisfactory performance, Vicky decided that she had to do something drastic. She refused to unlock him last weekend. It had already been more than a week and a half since he was last free of the chastity cage. He might have been angrier and more tormented by this if the lack of sleep hadn't dulled his mind and, in the process, his worries. Not that he could complain anyway, any mention of it would just extend his time locked up even more.
It was just him and Vicky in the house now. He hobbled through the kitchen with his ankles chained together, on his way to polish all of the glassware as instructed.
Vicky sat in an armchair nearby, her attention turned to a book of all things. When the other girls questioned her about this sudden interest in reading, she explained that she wanted to get a head start on the first semester of college.
He finished polishing one of the wine glasses, placing it back in the cabinet and started working on another one.
Of course, Josh would also like to catch up on his studies, especially since the exams he had to retake awaited him at the start of the semester only a few weeks from now. However, with all the pressure on him, there was no chance he could squeeze in any studying. He remembered what happened when he asked Vicky for some free time for his studies a few days back. She agreed, but with a condition, all the studying had to be done at the local library, fully dressed up in a skimpy dress with makeup and everything. Unsurprisingly, he didn't bother asking for more free time after that.
He set down another polished glass in the cabinet and reached for the next one.
"Wait," he heard Vicky call out behind him.
He turned around to face her a little too quickly, causing the short skirt covering his crotch to flutter up and expose his panties.
"Bring me that glass for inspection, slave."
He picked up the glass he had just set down and brought it over to her, careful not to slip up and break it. Vicky took it from him, examining it closely. "Hmm, just as I thought. You're slacking off."
"What do you mean Miss, I-"
"Save it," she said as she got up. "There's still dust at the bottom." Josh nodded silently, he knew that arguing was pointless.
"Lean over the counter and wait here. I have to go get something.
He did as she asked and patiently waited. She was probably going to fetch her leather crop or another instrument of pain to spank him with. He kept facing forward as he heard her approach him from behind. As he expected, he felt her raise his skirt, then his panties being lowered, exposing his bare butt.
It gave him a brief pause when she started pulling at his buttplug. After a few teasing pulls, she pulled it out completely. Ah, so she wouldn't spank him but just play with his ass instead. Fine with him.
He heard her squeeze something out onto her hand, it sounded like shampoo or something. A cold gel was spread around his hole. Lube? They usually didn't use any lube when they punished him, maybe she was feeling merciful.
Her finger plunged deep inside of him and explored his insides, spreading the cold water-based gel around. Josh squirmed as her finger poked around inside of him.
"You know, you've really started to fall off the deep end in the past couple of days. You just don't seem to be improving at all," said Vicky as her finger continued its exploration inside of him. After a few moments, a second finger joined in. "I asked myself, 'What can I do to help him?' And finally, I thought of something."
He twitched as her fingers were both pulled out at once. He felt the buttplug push back at his entrance. He wondered if that was all of his punishment.
She plunged the buttplug back inside of him. It kept stretching him open and pushing in. Even after a couple of inches, it seemed to not be stopping. His insides kept spreading out uncomfortably. Oh no, he thought. This wasn't the same buttplug.
"I went for a little trip yesterday, back to the store where we got your first one. Do you remember the one I suggested? I think that one is the right one for you after all."
Josh braced himself as the plug kept pushing inside of him. Finally, it stopped pushing further and stopped. His ass closing in after it and pulling it snugly inside of him. It felt like a giant pear was pushed up inside of him. He was frozen stiff, scared of what would happen if he moved.
Vicky giggled behind him and softly spanked his butt cheeks. "Come on," she said and pulled his panties back up. "What do you think of it?"
Reluctantly he slowly rose up, stopping each time he felt the plug shift inside of him, much to Vicky's amusement. Eventually, he managed to straighten up, awkwardly balancing on his legs.
"So?" she asked.
"Uhm, thank you Miss."
"How does it feel?" she asked.
It felt like he had to go to the bathroom, only he couldn't. This couldn't have been the one she showed him at the store, it felt at least twice as large. "It feels, strange Miss."
"Oh you'll get used to it in no time, trust me," she said and excitedly smiled. "And you don't know the best of it yet."
