Grace Breaks Caitlin: Cam Show

Caitlin was currently in Grace's basement, bent over a table, completely naked with her hands tied to a bar directly in front of her. Caitlin was a wreck, to say the least. She lay in a puddle of her own sweat combined with others, her long, blonde hair was a mess, her legs had given out, her ass was perfectly exposed and she had cum staining her back, face and everywhere around her. Grace had just had her favorite little bitch get fucked for 3 hours by several men more than eager to take out their pent up frustrations on a young college student's pussy. Caitlin was exhausted but knew that Grace probably had something planned for her tonight since she had once again told all of the men not to fuck her in the ass.

"Today we're going to try something...unusual," she heard Grace say from behind her. Caitlin looked back to see her mistress setting up a camera pointed at her. This was enough cause for concern for Caitlin, but as she noticed an ominous duffel bag that looked filled to the brim with unknown objects only added to her worry. She also noticed that, unlike a few minutes ago, Grace was now naked from the waist down with only a leather corset that displayed her impressive cleavage covering her top half.

"What's all this for?" Caitlin asked, her voice trembling a little bit. She'd learned by now that whenever Grace kept things secret, it was never good. She already felt like she was about to pass out, she didn't think she could last through whatever Grace had planned. Grace didn't answer her. Instead, she took a gag and a leather bunny mask out of the bag and put the mask over Caitlin's head and the gag over Caitlin's mouth.

"These are for your own good," Grace reassured her. It didn't work. Caitlin was still scared and more than a little anxious.

15 minutes later, Grace spoke again. Although, it was to the camera, not to Caitlin. "Hello, all of you out there!" she said in a bright and bubbly voice. Caitlin looked over and saw the laptop screen next to the camera displaying that what was being recorded was also being streamed to thousands of viewers. "Today I have my lovely assistant here who was kind enough to agree to help me test out a few new things! I'm very grateful that she has given her full consent to be part of my...experiment," she ended with a mischievous smile and schoolgirl like giggle.

Caitlin had never agreed to any of this and was now realizing that the ball gag in her mouth was to prevent her from being able to say that out loud. Grace knew from the start that Caitlin never wanted to be shown off in public, much less on a livestream to THOUSANDS on the Internet! Somebody she knew could watch this!

Caitlin heard a bunch of ruffling as Grace took out a few objects that made all sorts of noises. Grace pulled out a 16 inch dildo titled "Black Mamba".

Grace held up a drawing of a number line with certain numbers marked. "So how this fun game is going to work is whenever people donate a certain amount of money to this stream, my little BITCH here," she accentuated with a spank "is going to get another inch up her ass! Every inch will become more expensive but each one will be oh so worth it. Let's fit this whole thing in her! After this, we'll take requests from our amazing viewers, so let's get it started!"

The stream almost instantly passed the first few marked numbers as the audience was eager to see Caitlin's ample ass stretch to its limit. Every milestone was signified with a little bell. Grace sat on top of Caitlin's bare back. She felt a little bit of cum on her ass that was leftover from the gangbang. She quickly slid the first 7 inches in with a little bit of effort. Caitlin started shaking as she felt it go in.

The speed with which it was done combined with the force of the push felt like she was being torn from the inside. The fact that Grace's full weight was being pushed down on her didn't help either. Not only was it already 7 inches into her and still had more than half to go, but it was sooooooo THICK! Caitlin couldn't even begin to guess its diameter as each inch closer to the base made sure that her gaping asshole stayed pried open.

After that, Grace continued to plunge in the dildo inch by inch every time that the stream hit its next donation milestone. The sound of the bell caused panic within Caitlin as she lay bent over, trying to catch her breath between inches but also on edge constantly waiting for the next one. However, she couldn't deny that there was a hint of excitement every time a new inch went in.

Eventually, Caitlin's ass took in the entire Black Mamba. Tears welled up in her eye, this was more than she'd ever taken and she could now feel it pushing into previously unexplored territory, but at least that was all. Grace got up, and smacked Caitlin's ass again. She winced. "Would you look at that? She actually took the whole thing in! I'm so proud of you!" she exclaimed to both the viewers and Caitlin, giving her a little kiss on the cheek.

Caitlin was already starting to push the 16 inch dildo out from inside her butt. "No, no, no," Grace said as if scolding a misbehaved child, "Keep. That. In," she continued as she pushed the entire thing in once more, watching as Caitlin's ass swallowed it. Grace put a butt plug with a little bunny tail in as well to keep the dildo in. Caitlin shuddered as the dildo rushed its way into her. Just for good measure, Grace spanked Caitlin real hard to remind her to not disobey.

Caitlin didn't like that her humiliation was being shown to so many people who were probably all jerking off to it, even if a small part of her was starting to enjoy being the center of attention, not only for the viewers but for Grace who had full control over her.

"Sorry, about that," she continued talking to the viewers, "Don't think that we're anywhere near done yet. Just look at this fat ASS," she exclaimed with yet another hard spank that almost made Caitlin let out the butt plug. "This thing NEEDS so much more before my sweet little rabbit is fully satisfied. Plus, she's SO enjoying this," Grace said before kneeling down so that her head was level with Caitlin's exposed vagina. It had gotten seriously wet after having the dildo reach so deep in her. Grace stuck out her tongue and licked it, tasting Caitlin's juices. Caitlin perked up as the other woman's tongue tasted her. It sent a tingle down her whole body as she felt herself getting hotter.

Grace started reading the chat and there were many requests so she let them vote on which one they wanted. The answer was clear: They wanted to see more spanking. Grace grabbed Caitlin's ass, taking a handful of meat in each hand, "I don't blame you guys. Look at this plump, juicy ass," she said as she turned to Caitlin. "Now, you're challenge is to keep that absurdly long dildo and that butt plug in your big, fat butt as I spank you. If you fail, you're getting punished." Caitlin already felt sick, she didn't think she could.

Grace pulled a wooden paddle out of the bag and started rubbing it over Caitlin's right cheek. Caitlin tensed up, closing her eyes in anticipation. Grace wound up before giving it a loud WHACK. Caitlin jolted forward with a short, muffled scream as the wood made hard contact with her bare flesh, which had already been spanked recently.

Grace waited a little, savoring the last impact before winding up and hitting Caitlin's ass once more. Caitlin winced again as her ass rippled. The grip her ass had on the butt plug and the Mamba were slowly loosening. Grace wound up for another one, this time with full force and hit Caitlin's left cheek with a heavy impact. The sound of wood on Caitlin's bare ass echoed off the wall. Caitlin's head fell as she yelled from the pain which was now starting to mix with pleasure.

Grace, being a sore loser, wasn't happy that her full force strike didn't amount to much so she paddled Caitlin a few more times quickly with her full weight behind each one. The pain was intense but Caitlin started feeling pleasure after every smack because if nothing else, she was just happy to be winning this "game" of theirs. She even looked back and shook her ass as if to taunt Grace. Grace didn't want to lose so she grabbed her next tool, a whip.

All she had to do was whip Caitlin across the ass once and she broke down. The butt plug fell out followed immediately by the entire dildo almost shooting out of her ass after being crammed in so long. Caitlin felt so relieved to just have it out of her system but was once again tense in anticipation of her next punishment. Grace, humiliated by nearly losing, continued to whip Caitlin until the poor victim could no longer feel her ass anymore. She revelled in the way Caitlin's ass seemed to dance in order to avoid the whip. The jiggle of Caitlin's butt as she continued her relentless assault only made her want to continue more, but eventually she regained her composure and continued as planned.

"Alright, now it's punishment time," Grace said eagerly as she undid Caitlin's restraints and her gag. Even with the gag off, Caitlin was too intimidated after that whipping to say anything. Grace had Caitlin lie on the table on her back before kneeling down beside Caitlin's ass and putting a finger in it. Next she put in another and another and before long her entire fist had entered Caitlin's ass. Grace pushed her hand in deep until she was up to her elbow.

Caitlin didn't like the way she moved it in, then she shuddered when Grace started poking around her insides with her fingers, hitting spots that Caitlin didn't know she had in her. She could feel Grace hitting sensitive spots in her vagina through her ass. Then Grace started tearing her arm out and shoving it back in like a piston. Caitlin shook violently from the sensation this caused. She couldn't believe it, but she was actually starting to enjoy this. She looked down and could see the outline of Grace's fist in her stomach as Grace purposely pushed her hand so that its presence could be seen in the other girl's belly.

Caitlin eventually came so hard, her eyes rolled back and she went limp as pleasure flooded over her. She felt like she was on another level as she just leaked out fluid from below. She didn't want to enjoy this but after all this time with Grace, her body was now being conditioned for it. She came back to her senses to see Grace standing over reading the chat.

A message came in that stood out to Grace. "this is so hot! shove some candles in that bitch's ass" it read. She read it with a smile because she came prepared for something like this.

"Y'know, I really like that idea. Luckily, I came prepared," she announced. Grace bent over to grab something out of the bag. It was a wide variety of candles. Caitlin's eyes widened as she saw the sheer number and variety. From really long to really wide, they all intimidated her.

The wave of pleasure had passed over her now and Caitlin was filled with fear once more. After setting the candles up on a nearby table, Grace grabbed the Black Mamba off the floor and lined it up with Caitlin's ass. Caitlin was shocked when the thing was shoved in with little resistance. Caitlin's poor anus had been properly gaped so that it fit in almost easily at the start. However, as it pushed deeper and deeper, Grace put more effort in as she plunged the full thing into Caitlin. Caitlin could feel it deep within her, wrecking her insides. Now that her asshole had been loosened, the pain wasn't as bad, though. Grace then flipped Caitlin over and took her seat on her back once again.

"Alright, so now we're back to where we were. Whenever you all want to see more candles, a bell will ring and I'll see what else we can still fit in this bitch," she announced to the audience. Caitlin already felt like she was at her limit with just the 16" Mamba in her. It had just done some serious work on her backside. There was no way she could handle multiple candles. The bell went off quickly. Grace quickly shoved a whole candle in her before Caitlin even processed what was happening. Caitlin was beside herself with the pain of a whole candle in addition to the dildo now stretching her butthole. She pounded her fist on the table and tried to buck Grace off but it was to no avail.

The audience must have loved the reaction because the bell went off like a slot machine that had just hit a jackpot. They couldn't get enough, they wanted more candles in her. It was clear that the audience wanted to see this girl's limit and then break it. Grace shoved more candles into Caitlin's ample ass. Caitlin felt like she was about to burst. Grace then paused, despite the bell still going off.

She smacked Caitlin's ass yet again. "I want you to beg me for these next ones," she yelled out. Caitlin lay there hesitantly thinking about what her options were but she knew she had no choice when Grace turned around and leaned forward whispering to her, "If you don't I take off your little bunny mask right here and the world can see what a pervert you are."

"I'm BEGGING you to please put more in me!" Caitlin yelled out. She already felt about to burst and didn't think that she could handle more but the humiliation was not an option for her. She'd have to power through the pain and hope everything ended soon. Grace grinned before grabbing more candles and ramming them in without hesitation. She slammed candle after candle deep into the blonde's juicy bottom. Caitlin knew her mind would never be the same. She'd been broken in by Grace. Caitlin lost count of the inches that were within her but Grace counted eagerly.

"Oh we've hit 36 inches in, that's 3 feet, but 38 is such a nice looking number, we should go to that. Oh, 40 is so tempting right now and 43 is just a little more," Grace thought as she continued cramming candles into Caitlin's butt.

Caitlin's asshole got wider as she had to start fitting candles side by side. She felt like she was going to die but at the same time she almost enjoyed the feeling of discovering her new limits. The experience was unlike any other she'd ever had.

Grace then flipped her over, sat on her stomach and stuck one in with the fuse sticking out. Caitlin at this point could barely think, much less realize that she had taken in 51 inches of candles and dildos. A mix of pain and slight pleasure was all she could feel in that moment. It took all her effort just to stay conscious. Then Grace lit the fuse allowing the wax to melt within her ass. The burning from the melting wax on her ass brought Caitlin back as she blurt out, "Stop, st-" before she got cut off by Grace smothering her face with her ass and grabbing her hands. Every drop of wax that landed on her skin, caused a new twitch from her body. Caitlin struggled under Grace, turning every which way and trying desperately to get the other girl off her. Grace stayed comfortably on top of her, completely undisturbed by Caitlin's efforts. She watched as the candle got closer and closer to Caitlin's anus and relished the struggle.

Eventually, the candle got too short though and Grace had mercy as she decided to put out the fire. Caitlin was relieved but now she was back to being unable to speak and could only breathe when Grace wanted her to. Caitlin's face was now fully buried under Grace's ass cheeks as her pussy started dripping into Caitlin's mouth whenever it was open. When Grace slid back, she even knocked off Caitlin's mask. Grace started grinding on Caitlin's face, riding her nose until eventually she came all over the blonde's pretty face. Grace felt Caitlin's stomach with her hands. It had several bulges now from all the different candles that were rammed in her now ruined rectum. She traced her fingers along each candle that looked like it was trying to break out of Caitlin. Grace felt the blonde groan from discomfort under her. Grace crammed a few more candles in, causing the blonde to writhe in more pain and pleasure as her previously smooth stomach, became increasingly deformed. Caitlin had lost her breath and trying to get it back was impossible with her head enveloped between Grace's butt cheeks.

When Grace felt satisfied, she lifted herself up and moved her ass over Caitlin's stomach. Caitlin never saw what happened next coming. Grace let herself fall so that the full weight of her ass slammed into Caitlin's stomach. Caitlin lost her breath from the impact and squirmed as candles were sent rushing out from her backside. Her ass felt like it was now completely broken. After all the candles made their way out, the Mamba started making its way out again so Grace got up, gripped the 2 inches that were sticking out of the blonde's ass and ripped it out. Caitlin jolted upward before collapsing completely. In her state, she didn't even care that the audience had probably just seen her face. She was just glad to be empty and that her belly was back to its normal, smooth state. Her asshole felt like it was on fire, but in the end, she was beginning to enjoy Grace's humiliation of her and the extreme punishments she doled out.

"Well, looks like that's all we have time for today folks! Thanks for tuning in!" she announced to the audience before ending the stream. She took another look at Caitlin and by the look on her face, Grace knew she had broken her in.

Author's Notes: ALRIGHT, THIS STORY'S PRETTY WEIRD BUT 2 COMMENTERS ON "Grace Breaks Caitlin 2" WANTED THIS AND I THOUGHT I MAY AS WELL TRY TO MAKE IT. I TRIED TO STAY FAITHFUL TO THE COMMENT I WAS INSPIRED BY WHILE ALSO PUTTING MY OWN SPIN.

I DIDN'T WRITE THIS BECAUSE IT'S A FANTASY THAT TURNS ME ON LIKE WITH MY OTHERS BUT I WAS INTRIGUED BY THE IDEA AND WANTED TO SEE WHAT I COULD MAKE. IT WAS FUN, I DECIDED TO SORTA GO ALL OUT ON THE IDEA AND SEE WHAT COULD HAPPEN SINCE I CAN'T IMAGINE MYSELF WRITING SOMETHING LIKE IT AGAIN ANYTIME SOON. I DIDN'T EVEN KNOW THAT THERE WERE WHAT I'M GOING TO CALL "CANDLE FANTASIES" UP UNTIL I GOT COMMENTS ABOUT THEM.

I DIDN'T WANT THIS TO BE PART OF THE MAIN SERIES SINCE IT'S A LITTLE...ODD, SO CONSIDER THIS A MINI STORY THAT DOESN'T COUNT FOR ANYTHING TO THE "Grace Breaks Caitlin" SERIES. WE'LL CALL THIS AN UNOFFICIAL NONCANON ENDING! THE ACTUAL SERIES WON'T END LIKE THIS. I AM ALSO FULLY AWARE OF THE FACT THAT THIS IS NOT AT ALL ACCURATE AND COULD NEVER HAPPEN IN REAL LIFE. IT'S FANTASY.

AS ALWAYS, I HOPE YOU ENJOYED THIS AND PLEASE LEAVE WHATEVER FEEDBACK YOU MAY HAVE! TELL ME WHAT YOU LIKE, DISLIKE OR EVEN JUST MORE IDEAS! HEARING FEEDBACK IS MY FAVORITE PART OF WRITING STORIES!