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Author's Chapter Notes:

More torture awaits Jack today. Caroline still had a vice like grip on him. Play involving, pussy, ass, and toys.

Jack awoke rather well rested despite the situation he was in. Not the most comfortable night's sleep but definitely nice to not be inside someone for a night. Unfortunately for Jack, this did not remain so for long. The drawer flew open and a giant hand grabbed Jack tightly and pulled him out of the pitch dark of the drawer. The light blinded his eyes as they tried to adjust to the harsh new light.


With a big stretch of her arms and a loud yawn, Caroline woke up from a rather nice night's sleep. She slightly missed the wiggling of her toy inside her, greeting her as she awoke. However, he was to be punished, to be brought in line and taught his place. Before any of this day could be started, a shower was in order. As Caroline showered she couldn't help but picture her day today, she had to work from home again but she was sure she could find work for her toy.


Once the shower was over, and every crevice of her body had been cleaned, Caroline decided it would be best to make sure her toy was ready for the day ahead. She opened the drawer, threw her hand in and rummaged around for Jack. Once she had hold of him, she pulled him out and inspected him all over. Flecks of dust and odd hairs had stuck to him, where he had been wet when thrown in the drawer.


"Oh my toy is a bit dirty from last night's fun. Best to clean it off" as she picked a spec of dust off his face. She then got up, went to the bathroom and ran Jack under the tap, making sure to scrub every inch of him. 


Jack slowly started to realise what she was doing. Her words from the day before rang in his head 'properly make you a toy'. This must be what she meant, he couldn't talk or move, making him no better than her purple beast in the drawer, albeit a bit smaller and with no vibrate function. He let out a muffled scream as she ran him under the tap, but she ignored him. He was stuck like this until she said otherwise.


After finishing cleaning her new toy, Caroline went back to her room to prepare herself and her toy for the day ahead. She remembered that she had a suction cup somewhere that may be useful for the day ahead, and after a short five minutes of searching, she found it. With a devious grin she picked up Jack, tied the suction cup to his feet and stuck him to the bedside table to see if it worked. 


As Jack was tustled around while Caroline tied something to his feet, he dared to wonder what her plan could be for the day. Shortly after however, he found out, as he was stuck to her bedside table facing her, standing upright. There was only one idea that would require a suction cup and Jack didn't like it. 


Double checking that her toy was fastened in place, by pulling him down and watching him ping back upright, Caroline felt satisfied that he would do the job. She decided that it was time to change for work, today she wore a blouse, and a smart jacket, all for the few meetings she had today. She didn't wear anything on her lower half as she intended to keep herself busy down there all day. 


Releasing her toy from the bedside table she walked downstairs, tossed Jack into the table and decided to get ready for work. For breakfast she decided on some yoghurt and blueberries, something light and healthy to start the day. As she placed her bowl down, she thought it was time to get her toy to start work for the day. Picking him up she licked the suction cup and pressed Jack firmly onto the middle of the chair. 


Jack's heart raced as Caroline stuck him to the chair, he really didn't want to be inside someone for another day. Just once he wished he could live without that squishy feeling. This was sadly short lived, as Caroline slowly enveloped his body with her mouth. She quickly started to suck on him as her tongue licked and wrapped itself around him. The wet, hot saliva slowly coating his body as Caroline sucked him as if he were a dick. Brief flashes of light came over him as she raised her head only to slam it back down again and pull Jack deeper into her mouth. He couldn't help through all this to cum right onto her tongue as it brushed over his dick continuously. 


Caroline released Jack from her mouth, swallowed the tiny load Jack had deposited, gave him a slight smile before standing up. "Well, my toy is all lubed up, time to settle in for the day". Slowly she lowered herself onto Jack as he was stuck motionless. Inch by inch she slid Jack into her pussy until she was sat on the chair with him inside her, the suction cup working extra hard to keep him from being sucked in. "Oooo, that is a comfy chair, not a bad toy either" she rocks slowly on the chair, grinding Jack against her insides.


After taking a deep breath Jack was plunged into the same moist dark cave, he'd seen a few times now. "So this is what she had planned, I kind of knew, but a man can dream of a day relaxing" he thought to himself. As Caroline rocked in the chair, Jack felt himself being pulled forwards and then back, bent either way as the walls of her vagina rubbed against him. Small shivers could be felt through the wet walls and he rubbed against them, at least she could enjoy herself right now. 


Continuing to rock softly on her toy, Caroline decided to enjoy her breakfast. She thought it paired quite nicely with the small workout she was giving her pussy. With a clang as the spoon hit the empty bowl, it was time for her to enjoy the first orgasm of the day. Slowly she rose up from Jack until he was out of her, then slammed back down and started to ride him. Being the size he was, it wasn't as good as one of her toys that were twice the size, but the feeling of dominance that she had over him sent her over the edge. 


As light came over Jack he let out a sigh of relief, finally, he'd be free. As he looked up however, he realized this was far from over. As the giant pussy loomed over him, leaking from excitement, it slammed down, coating his body in the fishy fluids and squeezing around him. It felt like the pressure surrounding him was worse than it had ever been, maybe it was this new position, or most likely it was the fact he was nothing but a toy now. Caroline must've enjoyed that fact much more now that he couldn't move or speak.


With each wave passing through her body, Caroline felt the inevitable orgasm building within. Every ridge and angle on Jack's body hit a different area each time she slammed down. As the waves grew more intense, so too did her rhythm, it grew faster and more chaotic until she slammed down on Jack, tightened her legs and let the rush of lightning consume her body. It was an intense orgasm, she already couldn't feel her legs. As it subsided, she decided to log in and start to work, she had no reason to check if her toy was alright, not like she ever asked her other dildos how they felt after being used.


The walls squeezed Jack and they slid up and down around him. He could do nothing but hope that it passed quickly so he could leave this horrible cave. As this ran through his head, he felt the walls squeeze harder and secrete more fluids on him before clamping around him molding themselves to his shape completely. "Thank God, I can finally get out of here" he thought, but nothing happened. Caroline didn't check on him, or release him. The muffled sounds of tapping on a keyboard could be heard faintly through the loud heartbeat and fleshy walls. She really didn't care how he felt, as long as he made her feel good, he really was like an inanimate object to her now...


Four hours and three orgasms later, Caroline had lost all feeling in her legs. She decided that it was time for a change of pace for her toy. Slowly she stood up, using the table for support. Her legs were shaking more than her vibrator did on the high setting, it was good that she didn't plan on standing long. She inched forward slightly to hover her asshole above her toy. She hovered for a few moments to allow Jack to see his next prison, as the look of terror fell upon his face, she slammed down on him until every inch of him was in her ass. There was almost no resistance as he went in, her slick fluids that coated him acted as a rather decent lube.


As light flooded Jack's eyes he felt a large wave of relief to be free of his prison. The constant use and orgasms had crushed him constantly. Jack thought the fishy smell would never leave his body, it saddened him that he was getting used to it. It was worse that he was starting to enjoy being used, it excited him, as much as he tried to ignore it. He looked around to see what was next to see Caroline's asshole hovering above him. Dread slowly came over his face as he tried to shout around the gag, it wasn't long before he was deep within her ass as she slammed down onto him. He felt every movement of her asshole as it matched his shape, gripping every edge of him as it slid down his body.


A moan escaped Caroline's lips as she felt Jack in her ass, as quickly as she lowered herself, she stood up. The suction cup unfortunately couldn't stand the suction power of her asshole, it popped off the chair as she stood up and turned Jack into a human butt plug. As she could feel him stuck in there, Caroline decided to check in a nearby mirror. As she turned around and spread a cheek open, all that could be seen was the little pink suction cup. "Not the worst looking plug I've used", she decided that she should probably put on some clothes. Slowly putting on some panties and trousers she had out drying, she then sat back down and carried on working.


Jack's world went through many changes during this rush. Still stuck in his binds, he was at Caroline's whim. This new feeling of being a plug wasn't so bad though, the fear of being sucked deeper was non-existent thanks to the suction cup holding him in place. This didn't help the smell much, but he avoided responding to this due to the gag. He didn't want to be stuck and tasting his own vomit. With no concept of time In here, the seconds turned to minutes, minutes to hours, hours to days. He didn't know how long he was stuck in this warm stinky prison, but after an unknown amount of time, something tugged him free.


Once Caroline had finished work and a few hours had passed, she thought it best to use her toy one more time tonight to really drill in his purpose. She rushed upstairs, throwing her clothes off on the way, hopping as she rushed to get her underwear off. As the door to her bedroom swung open, Caroline lept onto her bed and immediately started to rummage through her drawer. She found her small pill vibrator with an accompanying battery pack. She'd had an idea for the last punishment today, reaching around to her ass she tugged at Jack and pulled him from her asshole slowly, feeling every ridge as he came out. Pulling him slowly around till he was Infront of her face, she gave him a sly grin.


As Jack was ripped from his prison and flung through the air. A vapid look came across his face. The last day of being used had dulled him completely. As Caroline's face leered in front of him, he noticed her grin but just sighed. There was nothing he could do about his situation so he resigned to just go along with it.


"Oh my, it seems a day was enough to break you. Well that works for me, you've got one more punishment to suffer then I'll free you tomorrow". Caroline said calmly. She started to tie the vibrator to Jack's head to turn him into a tiny wand. "You won't be going in anywhere this time, but it doesn't mean it'll be any fun for you". 


As the vibrator was tied to his head, the expression on Jack's face slowly shifted from vapid to fear once again. He didn't think he could find any more fear, but somehow the thought of being used as a wand did it. Though unfortunately over the past day of being used, he'd started to enjoy it to some degree. Was it really true? Was he really starting to break and enjoy what he was doing? His idle pandering was short lived however, as Caroline turned on the vibrator and his whole world started shaking violently. 


Caroline switched on the vibrator and watched Jack as he started to shake in her hand. It seemed like this was actually a good idea, he may work rather well for her needs, she thought. While holding him she reached for one of her few dildos that didn't already vibrate. Once the toys were ready, she fell back onto the bed, spread her legs and slowly got ready for the impending fun. 


As the world shifted from sideways to upside down then to a different side, Jack grew increasingly nauseous. The vibrations running through his body and being swung around in Caroline's hand had made him rather sick. Unfortunately he couldn't throw up or stop, as he looked up he saw Caroline's glistening vagina through his shaky eyes. To him it was a shiny pink blur, but there really wasn't anything else it could be knowing Caroline. 


Caroline slowly pressed the vibrator to her clit and threw her head back in pleasure as she felt the tingles of electricity pass through her. Though after being teased all day by using him as a butt plug, it wasn't enough. Shortly after she rammed the dildo into her, which slipped in with no issue due to how wet she was. This doubled the feeling zooming through her body and almost made her legs seize up. Though she had to enjoy this for as long as possible, slowly she started to build a rhythm of ploughing the dildo into her and circling her clit with Jack.


The constant vibrations made it hard to distract himself from the current situation. His eyes were being rattled, face being splattered with fluids as Caroline ploughed the dildo into herself and ripped it out, time and time again. He has to admit being outside was nice for once, though a shower would be nice. Of course this thought took longer than usual to get out due to the fact his brain was currently a pinball machine.


After a few minutes of sliding the dildo deep into herself before slipping it out again, Caroline had decided to finish up. Without hesitation she picked up the pace, and placed a couple fingers on Jack's head, pressing the vibrator harshly onto her clit. As these combined feelings hit her, her head rushed back and her legs started to shake. The orgasm came over thick and fast as it consumed her whole body. Shortly after, her legs fell limp and her arms collapsed where they were as she lay, breathing heavily for a short while.


Once feeling returned to her body, she pulled Jack up to her face. "Well I hope you enjoyed your day, and learned a good lesson about why you should listen to me". She sticks Jack down to her bedside table. "You can hang out there until the morning, we'll have some new fun tomorrow". She gets up, puts on some pyjamas and heads to bed for the night.


Jack spends a few minutes recounting today's events, it was a lot to process. Though he had come to a conclusion at least. Caroline is a psycho, not that was much of a discovery. But he had learned it was probably best to do as she says, at least until he could escape from this nightmare. Before heading to sleep, he thought about Emma and hoped she was doing alright after he had been kidnapped.


Over in Emma's household, there was only silence. Except in the bedroom, moans leaked through the ajar door to fill the upstairs corridor. The faint quiet moans of one name could be heard "Jackā€¦". Emma was currently laying on the bed, using a small bullet vibrator on herself. The size was close to Jack's and she just imagined it was him. This however, probably wasn't a good scene for Jack's future.


On the surface it seemed nice, she was thinking of Jack and wanted to be with him. However deeper down in her head, dark, gravelywhispers of a demon could be heard. "Yess, he's yours to use. Just a toy for your pleasure". 


"Mmm, shut up! He's not a toy! But he is mine, when he comes back. Now leave me alone!" Emma's battle with the demon continued. Though he was gone, Emma only hoped he would return soon, once he wasn't angry. Once he did, she'd not let him leave her again.

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