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.
