Link to chapter one in comments. Let me know what you think as it allows me to improve my writing.

Chapter 2: Anal Annihilation Part 1

Men advanced on each woman, Two per. With firm hands they forced each into a downward dog position, spreading their cheeks open. Karen flinched as they handled her reddened ass. A third presented an enormous beaded buttplug to their assigned woman. Smiling as they made sure each woman got a real good look. Hawks got in close to film the reactions of fear and disgust. It was over a foot long, with the first bead being the smallest, becoming progressively larger until the final bead, which was several inches in diameter. Each plug was of a different neon color, with a large flared base that looked like it would spread the crevice of their asses. Karen's plug was purple. After being sure each woman got a decent look they proceed to join the others at the rear.

"Dude look, this filthy skank already has one hahaha". One of them proceeds to play with Karen's heart plug, pushing it into her and wiggling it, then pulling it most of the way out before pushing it back in and repeating the action. EVERYBODY turns to take note of her. Some of the camera men shift to get a better shot of her specifically. Karen blushes a deep red and tries to avoid eye contact with anybody. Attempting with limited success not to moan while she's toyed with and laughed at. Cameras are shoved right in her face and she turns her head to try and hide. At least until she hears a stern command “look up” from one of the hawks. Face red hot, Karen picks up her head to stare directly at the camera. Out of her peripherals she sees the other woman watching her. Noticeably very uncomfortable Karen bites her lower lip in an attempt to stifle her sexual moans. Despite the humiliation she couldn’t help but to be turned on, the anal slut that she is. After all she wore the plug to signify her ass is available in hopes that it would be used.

The mistress steps in front of her. "Mmmm good, you came prepared" she caresses Karen's cheek. Looking at the men behind Karen she says "give me the buttplug." Promptly the plug is pulled all the way out and handed to her. "Suck on it" She pops the plug into Karen's mouth who, still shook by the example made of the other lady, obeys, sucking on it like a binky. At least I cleaned myself before coming here. Karen looks at the woman defiantly, or at least she tries despite being rather flustered and sucking on something that was just in her ass and still very warm. "Good girl, if you spit that out before I tell you, I will make you regret it." With a final pat on the cheek she says "you're going to be a favorite" and walks away.

Circling around the ring the mistress explains "your first trial is to take this plug in its entirety. Failure to do so will result in being unable to continue in our games.You shouldn't need me to tell you what will happen to you then." Karen shudders as strong, strange fingers suddenly begin lubricating and fingering her asshole. "These gentlemen are going to help you. I strongly advise you to relax and let them." Grunts, groans, and yelps blend into a cacophony of displeasure as they start pushing the plugs into the women’s assholes.

The first, then the second bead, went in with ease. There is a bit of resistance on the third but, with a little bit of force, it slides in too. Silver linings, Karen thinks about the plug in her mouth. The fourth is where things get dicey. She grimaces as she is stretched out past her typical limits. Discomfort begins to give way to pain. The bead seems to get stuck for a moment. She feels them sort of wiggle it in and out in an attempt to loosen her up. Her eyes begin to water. Then with a jolt of pain they force it the rest of the way in. Karen squeals as her body trembles. Even after it's in the pain lingers. "Shhh shhh easy there baby girl you're doing great, already halfway" Karen's groans at that. Only halfway?! Oh god my asshole’s going to be ripped apart! Karen continues to whimper as consoling hands gently rub her buttcheeks.

Karen feels the plug pushing deeper into her again. Oh god. She instinctively tightens, then forces herself to relax the best she can. Her handlers gave her a break so she can regain her senses, it's almost sweet. Besides the other women appear to only be two or three deep still. Seems like they decided it's been long enough though. Her asshole stretched like it's never stretched before. She gasped, then quickly put her hand over her mouth to prevent the heart buttplug from falling out. They went slowly. Pushing and pulling, pushing and pulling, gradually picking up speed in their movements. Her asshole loosened, and they were able to fit a little more with each movement. They went on like that, pushing and pulling, moving a little deeper every couple minutes. Karen moaned loudly. Not in pain but pleasure. Her eyes glazed over for a second before suddenly refocusing, shocked at what she just did. Snickering began behind her. "You're a nasty little buttslut aren't you." A hand slapped, with a wet smack, her pussy. She moaned again. "She's sopping guys". This drew again attention from some of the other girls. They gave her looks that ranged from confusion to revulsion, the ones lucid enough to do so anyways. Joy made eye contact with her. She gave her a familiar, quizzical, "you slut" look. Karen has always enjoyed anal sex. In addition to pushing her limits. Outside of the circumstances, she could honestly see herself getting into a situation similar to this of her own volition. Fuck it she thought, and lifted her ass up into the plug, curving her back and bringing elbows in to her knees until her ass was almost straight up in the air. Lips puckered around the plug in her mouth she moaned loudly, almost obnoxiously.

The fifth bead broke the halfway point through Karen's sphincter and her ass sucked it in the rest of the way with force. She felt the significant length already within her push even deeper, churning her insides. That movement caused her to take in a sizable portion of the sixth bead as well. "Nnnggghh mmmph". She lowers her abdomen by a margin allowing the sixth to pop back out. Don't let the sudden enthusiasm fool you, that hurt like hell. A lot of attention was on her now. Camera men shifted to get more coverage of her and even the girls caught up in their own agony were looking at her. A bit overwhelmed by the attention Karen was determined not to let the embarrassment beat her. Panting, blushing, trembling, she slid up the plug back to the sixth bead, gently grinding on it. The plug itself was rather pliable, bending with her movements. If the way out of this is to be a slut, well then I might just have a chance.

Karen could hear clapping and whistling from the men surrounding them. She began working in tandem with the guys pushing the plug into her. Gently swaying her hips, she stretched herself further and further on the plug. The men would apply pressure when she pushed up and pull out a little when she pulled away. They played with her wet pussy while they worked on her. Fingers slid in and out of her folds, occasionally circling her clit. Their excitement was palpable. Turning her head to watch them, she stared with fuck me eyes and sucked audibly on the heart plug in her mouth. Then she made mewling sounds as she worked the plug deeper into her ass, both from the labor and the sexual thrill she was now feeling. The bead was so big she was legitimately worried it would tear her asshole if she wasn't careful.

Karen would let the bead slide out of her. Then she would take it back in, ever so slowly, fitting more and more into her over time. She had never so intensely trained her asshole before. While she had plenty of experience with anal sex, she had only ever taken something perhaps a little more than half as big as this before. She has always been a bit of a size queen however and is now realizing she can fit as much, no, probably even more, in her ass than her pussy. There doesn't even really seem to be much pain anymore despite this bead being far beyond anything she could have possibly imagined fitting in her tight asshole.

After what seemed like an eternity the sixth bead finally slid all the way into Karen's ass. This one didn't just pop in at a certain point like the others either. They had to push it, and the significant length already inside her, all the way with consistent pressure. Now she is not just dealing with getting the bead through her tight (well maybe not so much right now) asshole but also with accommodating the huge plug inside her. She moaned and twitched as the last of the sixth bead made its way in.

Karen laid on the mat exhausted. No longer having enough energy to keep her head up she just let it flop to the ground, her cheek resting on the ground, her auburn hair splayed out around her. Body limp, she would have gone entirely prone if not for the men firmly holding her rear in the air. Her eyes flickered in and out of her skull, she hadn't felt this full since carrying children. The sound of Joy's passionate moans brought Karen back to this world.

Karen meekly turned her head and locked eyes with Joy who had been watching her this whole time. Karen's fervid display clearly inspired and aroused her friend, who was looking at her with burning eyes, taking the lengths of her plug like a champ. Karen gave her friend a wide smile holding the heart plug between her teeth. Joy mouthed "we'll get through this" before shutting her eyes and groaning through clenched teeth. Looks like she just took in another bead. When she opened them they were still fiery and filled with lust. She puckered her lips and made a heartfelt kiss towards Karen. Despite how screwed up this situation is Karen is genuinely glad Joy is here, and given the situation, there is no one Karen would rather have at her side.

Karen was vaguely aware this whole transaction was being filmed and spectated. She didn't care, she couldn't possibly be more exposed and violated than she already is. And if that interaction seemed like they are maybe more than just friends, well… both Karen and Joy have agreed they prefer men, but with how often they have been intimate around and with one another it's fair to say they might be a little more than just "close".

"One left buttslut." Nice, Karen thinks to herself, new moniker. The seventh was so wide that when they tried to push it into her at first it simply shoved her to the ground. They readjusted her body so her ass stuck back in the air. They gripped her tight this time, firmly rooting her in place. Then…

Karen screamed, all agony this time, as the bead was shoved with force a couple inches into her ass. "TAKE IT OUT! TAKE IT OUT! TAKE IT OUT!" She thrashed and cried and tried to escape. The men on her rear apparently prepared for this reaction. They held steadfast, keeping her immoble from the waist back, and prevented her from pushing out the plug herself. They did pull it out just a little bit however, for whatever relief that might be worth. Karen wailed and sobbed. She tried hitting them a couple times. After a few minutes she was finally able to get a hold of herself. Shaking, her body flooded with adrenaline, she braced herself for what had to be done. "Get on with it then" she said feebly. They continued, slowly, gruelingly, with the same familiar strategy. They pushed in and pulled out, pushed in, pulled out, little by little, they worked the bead into her ass. A little time went by before Karen realized what was missing.

Karen's head shot up, eyes wide, searching. She saw the heart shaped butt plug lying a little ways away. Oh no. Maybe if I… she looked up and saw the mistress watching her with a wicked looking grin. "I said you're going to regret that. You're still in the game however. Don't think about it right now. You have…" she smirked "bigger things to worry about at the moment."

Just as Karen felt like she was beginning to get used to how her anus was being stretched, they would push just a little deeper and the pain was still there. She felt it not just in her ass but her vagina as well. It was so large that it was pushing on her g-spot through her perineum. The feeling was overwhelming. Soon enough however pleasure again began to mix with the pain. She found herself moaning instinctively from the sensations with every tiny thrust, and it was exciting the men behind her. Hands began intimately touching her on her inner thighs and belly. Karen realized there were now more than just three men behind her. "She’s so fucking hot" one exclaimed. A weird sense of pride mixed with her humiliation. Fingers began gliding along her wet cunt. A couple eventually found their way inside, compressed against her g-spot by the giant bead moving into her rectum. Karen had never felt so debased. And she was enjoying this despite herself. Her mind became empty of everything but the strange profoundness of it all. Pain, pleasure, humiliation. Before she realized what was happening the base of the plug nestled itself against her asshole, a foot or so of unholy sex toy making her ass its home… and then…

Karen exploded in orgasm, entire body convulsing, she sprayed the men behind her. In astonishment they laughed and cheered. Again she came almost as soon as the first ended. Then the fingers inside her sprang to life, assaulting her g-spot, making her cum a third time. This was one of the most powerful multi-orgasmic episodes of her entire life. Karen gibbered like she had gone mad while they forced a fourth orgasm out of her. Finally, blessedly, they stopped, else she might have actually lost her mind. When they released her she collapsed, sluggishly, to lay belly flat on the mat. Twitching she blinked asymmetrically, eyeballs fluttering in and out of her head, and she was drooling from both sets of lips. She lay like that for a while, stunned by post-orgasmic bliss, the pleased sounds of men, and the noisy struggling of women washing over her…

Karen was the first girl to get the entire plug inside her. From tip to base the ordeal took roughly an hour for her. She had made herself quite popular, and by the time she had cum a couple camera men had already dedicated themselves just to her. The waterwork display was caught on multiple angles and one of the cameras actually got itself sprayed with her squirt.

Dazzling light emitted from the great hall’s fabulous chandeliers reflected off Karen's glistening body making her freckles pop in some places while obscuring them in others.

When wearing buttplugs Karen can often almost forget about them due to her experience. Her vast buttcheeks totally concealing bases of any size. Not this time. The enormous plug with its wide flaring base bites into her cheeks, keeping them permanently spread with much discomfort. Thicker than most cocks she’s taken, the shaft alone kept her tight hole gaped. Despite this the spacing between base and last bead was abnormally small. Sandwiching her sphincter between them and keeping the oversized base pressed as snug as possible against her hole. Combined with the massive beads, and footlong plus length, the monster inside her was the most invasive sensation she had ever experienced in her life. There was no getting used to this. If anything it only seemed to overwhelm her more the longer it was in.

Karen’s body heaved and trembled while she watched the remaining women struggle desperately. Eventually the mistress stepped into the circle of women once more. “Thirty minutes remaining.”

Everyone left looked like they might not make it. Including… oh no, Joy. Karen’s best friend was looking worse for wear. Hyperventilating and panicked, Joy would need to be more relaxed to fit that monster inside her. With noticeable effort Karen rose to her hands and knees. Exhausted, her double H breasts dragging like anchors, she managed an awkward bear crawl towards her friend. On instinct her captors acted to restrain her. They stopped themselves, seemingly curious about what Karen was going to do.

Joy locked eyes with Karen as she stumbled and wobbled during her approach. Palpitating and now with four men working on her ass like their laying foundation she croaked “Karen you look ridiculous.” Karen laughed and embraced her friend. Together like that they lie, comforted by each other's warmth. Joy still held up her rear for men as the two of them nuzzled heads. Both cried a little. Slowly the interaction became more intimate until a nuzzle turned to a kiss. “I need you with me through this.” Karen said softly. They kissed again with passion. “Just relax,” Karen whispered.

Tongues tangled through velvet lips and many seemed to enjoy this. Hawks acted swiftly, eager to capture this unexpected display of intimacy. Men stared slack jawed. A whistle was abruptly cut off by another's jab. This display was too exquisite to risk disjoining. Even other women dejected and dominated goggled them in awe. The mistress smacked some of the men aside and sharply motioned for them to continue. “Fifteen minutes” she declared “anyone who hasn’t taken it to the base in that time can kiss their comfortable married lives goodbye.” All the same she watched with amused approval.

Karen battled Joy’s tension with the most passionate kiss she ever gave. Joy would gasp and moan. Each time Karen would pull her back and mouths collided with wet smacks. Joy’s soft whimpers tickled Karen’s mouth while they kissed. She could feel Joy’s tears fall on her cheeks. Yet the distraction seemed to be working. Joy never stopped kissing back. Karen knew the final bead was being pushed in when Joy began grunting and moaning into her mouth. Eventually Joy broke away, eyes glazed and flickering. The beasts behind her gave a pat on the ass before stepping back “Good Job hahaha!”

Karen wiped some of their combined saliva off her mouth and blushed upon seeing her dark red lipstick painted all over Joy’s face (like usual, Joy wasn’t wearing any makeup herself). Joy didn’t explode in orgasm like Karen, instead seeming wholly overwhelmed. It made her feel like a slut by comparison. Well… an even bigger slut. “Karen” Joy said in a shaky voice. “Here, let me fix that for you” she said while rubbing around Karen’s lips with her thumb, presumably fixing her lipstick. Karen smirked at how silly the gesture was. That was just like her, always looking after Karen. Raising her eyebrows, Karen was trying to think of how to fix the lipstick she got all over Joy’s. Before she could do anything however, a strong hand grabbed her by the hair. “Back in your place.”

Grimacing, Karen let the man lead her away. He was not too rough. Just enough force to make her feel controlled. Karen’s breathing was constrained. It felt like the beads in her ass were displacing internal organs.

Back at her spot in the circle Karen had herself forced back into the downward dog position. Like that she waited as the mistress finished her countdown.

“Five more minutes!” … “Two more minutes!” … “One more minute!” … “Thirty seconds!” … “Fifteen seconds” … “Ten seconds” … “Five! … Four! … Three! … Two! … That's it! Times up whores! Get the losers out of my fucking sight”

For a second it seemed like all chaos was about to break loose. Woman screamed and pleaded. Some fought, kicking at the men behind them and attempting to flee. This rebellion was promptly squashed. Each woman already had at least three men already on top of them and some degree of ungainly buttplug sticking out of their ass. Large naked men tackled and restrained each woman. Pleas were cut off by gags without a shred of remorse. In fact the beasts seemed to be having the time of their lives carting off the despondent women with their plugs still hanging out of their asses. Frankly, it was brutal. Karen cowered by instinct as nearly half of the women there were taken away to be locked in the pillories and tormented. She found herself having mixed feelings about her earlier whorish antics.

“THE REST OF YOU! OUTSIDE! NOW!” The mistress bellowed. What? Karen thought, unable to process words. She could unfortunately process the licking of the whip on her still tender butt cheeks. Without thinking she hurried away from the flagellation. First on all fours but then attempting to break into a full sprint. Only to be stopped before she could get fully upright and shoved back down on all fours by the back of her neck. “CRAWL BITCH!” The bear screamed right in her face, splattering her with his spittle.

Karen scampered as fast as she could go. Despite being fit she is still a larger woman with large breasts that careen wildly throwing off her balance. Not to mention her large wobbling ass makes an easy target. Being so easy to bully garnered her a lot of attention. Men would push her even further off balance with their feet and kick in the hinges of her knees when she tried to get off them. She didn’t even know where she was going. Just staggering away from the sting of the whip. None of that was even the worst of it though. Deep inside her guts she could feel every inch of the anal beads. Overwhelmed, she was legitimately concerned about moving too haphazardly for fear of some internal injury.

Eventually she noticed a huge screen door being opened in the direction she was sort of heading. Correcting her course she made for it as hastily as she could. Trailing behind the stampeding women as she was, Karen had a fantastic view of their asses, and noticed something that while inconspicuous still stole a thought from her overtaxed brain. In the buttplugs. Are those… threads? Like for screwing something into? The thought disappeared as abruptly as it came. Soon Karen found herself tromping into sunny late morning rays and freshly cut grass.