Having overcome the initial challenges, Tegan’s descent continues
Halloween pt 2
This is a direct continuation of Part 1 which I recommend you read first.
-phenylalanine
After a small break to take a breather and as the groups finished up their punishments of their sacrifices, Tegan was taken down from her rack and half carried on wobbly legs back to the table she had been lain upon for the marathon session that had taken place earlier. Her mind leaped to the conclusion that they were finally going to finish the job they had started as she associated the table with being fucked. The rack was removed by the men who weren’t preoccupied with assisting her. Her nipple clamps were removed and she gasped with a mix of pain and relief as blood surged back onto the aching tissues. One of the men gently suckled on them, swirling his tongue around them as if to soothe them with his saliva. It seemed to help.
“In the Sixth circle, the Heretics are punished. The Heretics who forego conventional wisdom and seek forbidden knowledge.” The Speaker’s voice cut in again.
While her tender nipples were being attended to her wrists were quickly bound with cloth again, and she realised her teeth were still clenching the leather bit. Rather than being laid back on the table she was bent over it, facing towards the inside of the circle again. Her and the other four remaining women were going to face each other for the next stage of the ritual. This time, as she was held down against the table with the pillow under her stomach to prop up her ass, she felt manacles being fitted around her ankles and realised she was being secured to the table so she couldn’t move. While it did create a knot of anxiety in her gut she was reassured, strengthened by the woman who had already tapped out and immediately led from the room to salvation. Tegan knew that, whatever she feared might happen, her limits would be respected – and that meant she was ready to test exactly where those limits were. Her eyes scanned for Sam again but he wasn’t looking back at her, apparently entirely fixated on his subject, the athletic blonde. He was testing the weight of a leather paddle with studs and Tegan swallowed thickly as she realised someone behind her was probably doing the same.
She arched her back and let out a stifled cry as the paddle connected with her ass, joined by a chorus of the other women as they were also spanked. Unlike the light but stinging lashes of the cat-o-nine-tails and the crop, the paddle connected solidly and she felt her flesh ripple from the blow. The wielder gently caressed the cheeks after the blow and she could feel the testure of the polished leather riddled with studs against her cheeks as the heat rose in her skin. She imagined her pale upturned ass beginning to glow red. Without warning the paddle connected again but she groaned through it. Again the caressing motion. She felt like normally when a submissive was punished in this manner they were expected to count them off, but she hadn’t been told to – or how many to expect – so apparently it was her lot to simply not know. A third blow landed and her voice was reduced to a pitiful whimper, her toes curling into the thick carpet, her bound hands gripping the edge of the table in front of her. A fourth strike and she whimpered again, squirming as she waited for the fifth and it landed heavily. Mentally she kept track of how many times she was spanked and believed it ended around thirty, which, believing that there were six men clustered behind her, meant that had taken five strikes apiece. Her asscheeks felt battered, bruised. She was definitely going to have some marks left after that one. She felt something touch her pussy lips and realised it was a couple of probing fingers easing into her slick tunnel. The man moved them around a little and she shivered feeling his touch inside her. Although she had recently been almost endlessly ploughed by multiple men and had an unexpected orgasm while being whipped, her pussy was still sensitive, needy. While her ass ached and stung from her recent torment her body was still aflame with need and her cunt clenched hungrily at the probing fingers. The man entered a third finger, twisting them around as if testing her elasticity. It felt strangely impersonal, clinical in that regard. The man withdrew his fingers and cupped her crotch from behind, slipping a finger between her labia to briefly play with her clit, but then took his hand away again before Tegan had time to enjoy the touch.
“She’s soaked.” She heard a voice comment softly, reporting his findings back the other men in the group.
“I bet she could take a baseball bat up there.” Commented another in a mocking tone of voice.
“The seventh circle holds those who commit the sin of violence” The speaker said coolly. “Violence against man, violence against self, and violence against nature – such as the Sodomites.”
As he spoke Tegan felt strong hands pry apart her asscheeks and a finger begin to apply a cool gel to her puckered rear entrance. While the sin of violence seemed like a weak excuse to do so, of course they were going to fuck her ass. What kind of ritualistic Halloween orgy would it be without some group sodomy? She should have expected this as soon as they pushed her face down onto the table – she had momentary flashbacks to the time her housemates had restrained her down and taken out a week’s worth of sexual frustration on her poor little starfish, until she had passed out. From that point she had begun to set boundaries and tried to encourage them to treat it as more of a special occasion rather than an everyday occurrence. While she had never rejected an attempt to sodomise her, it had become less frequent. Though by that same token, it had certainly not stopped Trevor from forcing his brutal crotch cudgel into her petite body.
She took a deep calming breath as she felt a finger push inside her, smearing some lube around the inside of her tight ring. Six guys, of varying sizes. She could handle this, and somewhere in the back of her mind she knew she would probably enjoy it. While she wished the men were lining up to stuff her other hole, she could not deny the aching need to have someone inside her again. She briefly raised her head to assess the position the other women were in and they all seemed to be waiting patiently. A brunette across from her seemed to be the most anxious of the group and she seemed to be staring back at Tegan. Tegan wondered why until one of the men positioned behind her hunched over to whisper into her ear as he guided his swollen tip to her greased-up hole.
“My wife has never had anal before.” He whispered, and Tegan realised this was the husband of the married couple who she had met during the drinks at the start of the night – which seemed to have been so, so long ago. “She’s never allowed me to try it. I told her it might happen tonight, and she promised to make me proud. But regardless, I’m going to get mine.” He pushed forward and Tegan tried to relax as his steel-hard cock pressed against her anus, forcing the muscle open to accommodate him. Tegan wasn’t sure if his little monologue warranted a response but with the bit still in her teeth she had a reasonable excuse to say nothing, a gentle grunt escaping her as she felt his lubricated cockhead pop past her sphincter. Her muscles involuntarily clenched, trying to reject the intruder and the man groaned with pleasure as he continued to sink deeper inside her until he was buried all the way inside, the silky caress of her bowel juxtaposed with the tight grip of her ring. Tegan could not estimate his size, she wasn’t sure which penis belonged to which man, and the tightness of her ass made everything feel big especially since she had broken the habit of wearing Angus’ plug all the time. All she could be sure of was that he was not as thick as Trevor or Angus, or as long as Sam.
Across the way the stranger’s wife seemed to be struggling with her partner. Tegan could see her shoulders heaving as she took deep breaths to calm herself, a strained groan of discomfort escaping from behind her clenched teeth. Tegan wondered if she was going to be the next to tap out, or if she would somehow find the will to carry on now that someone other than her husband had divested her of her anal virginity
Meanwhile the man inside her had begun to slowly thrust and she could feel every small movement as he slowly relished the grip of her rear entrance. Tegan, with nothing to do but lie there and take it, took slow deep breaths. If all six of the men planned on taking a turn she was really going to struggle, but for now her body felt invigorated and renewed by having a cock inside her again, even if it was in her ass instead of her pussy. The man started to pump faster, his breath hot on her cheek as he remained hunched over her, grunting in her ear.
“You love this don’t you, you little whore.” He lifted his head and for a moment he and Tegan jointly watched his wife as the man behind her finally seemed to sink his full length into her newly deflowered back door. Her back arched and she let out a strained groan as she bit down hard on her gag, but she did not surrender.
“I’m going to have her ass every night from now on.” The man continued as he started to speed up again. Tegan knew he was getting close to cumming and gasped gently both from the ache of being stretched open and the anticipation of feeling him cum inside her. “She’ll learn to love it just like you do.”
With that the man apparently reached his vinegar stroke and drive his hips down one last time, burying himself as deep as he could inside Tegan. She could feel his cock flexing for a few seconds before the first spurt escaped from the man and dribbled into her, creating a warm, wet, squishy sensation. The man pumped his hips one last time wanting to get the most out his fleeting experience with anal sex and then he reluctantly withdrew, her well-trained muscles immediately closing up to seal in his gooey gift as he stepped away and went to clean himself off. With the first man finished Tegan found herself silently begging for the next one to hurry, she’d had a taste and needed more, her body inflamed with desire. Across from her the man inside the other woman’s ass seemed to be taking his time, easing her in instead of rushing to the finish, wanting to ensure that she wasn’t inclined to quit. Finally she felt another man step up behind her and the cool tip of his freshly lubed prong pressed against her recently vacated hole, the head popping in with little resistance. He quickly slid the rest of the way into her, carefully adjusting his position until he was pressed up against her. It occurred to Tegan that, not for the first time, while her small ass was probably less visually appealing, the fact she didn’t have big round glutes getting in the way probably meant men could reach deeper inside her.
Her thoughts were quickly derailed though as the man tightly gripped her slim waist and began to fuck her.
There was very little buildup this time, as soon as the man found his rhythm he didn’t hold back and Tegan moaned in a mix of pleasure and alarm as he started to jackhammer her asshole as if she were an experienced porn star. She bit down to stifle her sounds as she gripped the edge of the table, the man driving into her. While uncomfortable at first her needy body quickly adapted and she could feel a tightness building in her pelvis that heralded building arousal and release. She whimpered as she realised that she was about to come from anal – and while the thought was thrilling the idea that her body could derive actual physical bliss from something that she always saw as exclusively for the pleasure of a male partner made her flush with humiliation. She started moaning into her gag, her back arching as she drew loud ragged breaths, and then the orgasm filled her all at once.
The man drove in deep as her convulsing butthole squeezed and gripped his shaft, keeping himself buried inside as her body rode out the waves of pleasure. She could feel him flexing inside her and she awaited feeling him unload up inside her but he didn’t. Once she was done he pulled out and was immediately replaced by another cock, cool with fresh lube, that slid effortlessly into her well-prepared hole. She clutched the table edge again and simply held on as the third man made use of her, lying panting and weak. A man knelt down by her head, presumably the one that had just finished with her and whispered to her as he caressed her temple while tucking some loose strands of hair behind her ear.
“You’re quite the little butt slut, aren’t you?”
Tegan let out a breathy moan in response.
“Well if your whore ass isn’t too used up when we’re done with you, feel free to hit me up for more.”
Tegan could think of half a dozen responses to that – but now wasn’t the time for a discussion. She just moaned again as she got fucked and the man whispering to her got up and walked away out of her field of view. Tegan returned her attention to the woman across from her, the ‘wife, as the man fucking her finally seemed to be picking up steam and thrust forward with a satisfied groan. As soon as he pulled out the woman spat out her leather bit and said “Virgil. Virgil!”
The men around her let out a collective sigh of disappointment that only one of them had been able to take a turn with the reluctant anal first-timer. The husband, who had already finished with Tegan walked over to her to assist in gently unbinding her from her restraints and escort her from the room telling her in a low voice how proud he was. Reflecting on that probably being the reason he was so keen to finish with her as quickly as possible – before his wife inevitably tapped out - Tegan took a deep nervous sigh as two of the men from her group broke off and headed in her direction – though it seemed one of them was the one who had just finished with the ‘wife’, so at least the number of men who were going to abuse her asshole had hopefully only increased by one. She felt the man inside her pull out to make way for number four and Tegan took a moment without the distraction of having her ring stretched out by cock to assess the remaining competitors. Obviously as the pool of women shrank the number of men each sacrifice had to take on would grow exponentially.
To her immediate left was a large-breasted girl with jet black hair and dark eye makeup Tegan could only classify as “emo”. She rested on her elbows giving her heavy tits enough room to sway and back and forth as the man behind her gently thrust against her large pale ass. She took him placidly, her eyes glazed over – her mascara and liner had run, staining her cheeks with black tears. Further around the circle was a skinny Asian girl, who from this angle seemed even more petite than Tegan. She locked eyes briefly with Tegan, her expression intense though it was hard to say if her jaw clenched from biting down on her own leather bit due to discomfort or lust. Maybe as in Tegan’s case, it was a little of both. Then finally after the spot vacated by the ‘wife’, was the curvy blonde Sam was spending the evening with. She had spat out her leather bit and was muttering under her breath as she was used, urging, or maybe begging, the men to hurry up and cum for her. Like the emo woman she was balanced on her elbows but had her back arched so her C-cup tits jiggled in the air.
Tegan wondered what would happen if she was the last one standing? A marathon 25 man gang bang? In her mind she suspected she would tap out before that happened – though she had to admit that even after making it as far as she had, even while being actively fucked, she was still feeling quite insatiable, and began to wonder if her body was going to make all her decisions for the rest of the night.
She let out a guttural lusty moan as number four forced his cock up her ass and if the stretching burn was any indication this was the particularly well hung individual from before. He eased into her gently but steadily, finding very little resistance left in her well-prepared muscles. While he didn’t give Tegan as much trouble as Trevor, she nonetheless had to brace herself as his prick burrowed deep into her soft cavity. The man idly traced his fingers over her back as he eased in and out, tickling her a little which made her muscles clench around him. He maintained a slow rhythm, apparently wanting to pace himself as well as go easy on her, but it wasn’t long before he let out a groan and she felt him vacate from her – though frustratingly, confusingly, she didn’t feel him ejaculate. Were they all – with the exception of the one man who’d brought his wife – avoiding finishing inside her just out of some kind of courtesy?
She squeezed her eyes shut as the fifth man entered her, taking deep slow breaths as she tried to ride out the rest of the endurance trial. While her body continued to tingle with pleasure, she was definitely experiencing some fatigue and it occurred to her that this was only the seventh step of nine, and her mind turned to what acts might lie ahead. The man finished after a couple of minutes, again pulling out before spilling inside her and was replaced by a sixth, and the process repeated until the seventh man finally finished with her and stepped away, leaving her bound, breathing hard. She listened to the sounds of the other groups likewise finishing up over the next few minutes until it seemed everyone was finished.
“The eighth circle holds those who commit the sin of fraud” The speaker said coolly as Tegan’s ankles were unchained from the table legs and she was pulled upright before being pushed down on the table again, this time on her back. She winced as her lower back muscles protested after being bent over for so long, and her ravaged hole spasmed, almost like it was cramping. The pillow was adjusted so it was under her ass keeping her hips elevated and she was held down as her legs were bent and pulled back against her, and she felt manacles close around them again. She quickly realised she’d been cuffed to a spreader bar which was going to keep her legs apart. Then belts were wrapped around her thighs and shins and cinched tight, so that her legs were forced to remain bent. She could already feel a bit of burn in her muscles, but her more immediate attention was drawn to the fact that the way they had her restrained spread her wide open, putting her pussy on display. Having been naked for what felt like hours at this point, and having had multiple men use all of her holes she did not have any reason to be shy, but she did feel vulnerable.
Once she was fixed in place – and while presumably the other three remaining women around the room where likewise trussed and put on display live some obscene thanksgiving turkey, the speaker continued.
“In the inferno Fraudsters are better thought of as panderers and seducers, those who tempt and tease and flaunt what they have to get more of what they want.” He spat the last word almost as if it were something that angered him and sent a chill down Tegan’s spine. It was unclear what punishment would fit this notional sin. Either side of her men stood over her and started groping and fondling her chest again, playing with and tugging on her nipples which still ached a little from being clamped earlier. One man cradled her head in a hand while using his other to rub his semi-erect cock on her cheek, though he made no effort to put it in her mouth again. Tegan was also relieved to discover that as she suspected the men had had the courtesy to clean themselves up after penetrating her ass.
Presently she felt a cool touch on her pussy lips as something was pushed into her – fingers, again, but apparently slick with lubricant. Her mind reeled: she knew she was still wet and ready to be entered, her body was already tingling just from feeling something inside her needy vagina that clutched eagerly at the new entrant. There was no need to make it easier to put something inside her unless it was larger than what she could comfortably accommodate. She let out a grunt of protest as she realised what was probably about to happen, but the men fondling her tits pinned her shoulders down to keep her from struggling.
She felt a third finger added to the two already inside her and continued to squirm. She knew that she could put a stop to this by spitting out her gag and saying the safeword, but something held her back. Maybe it was that she didn’t want to quit, maybe she just didn’t want to bring this night to an end, but her body was compelling her to resist as the man forcefully massaged her with three fingers, coaxing her entrance to loosen up to accept them before adding a fourth. She could feel the torturous taper of his fingers close together at the tips but inevitably widening as they went deeper, forced by the shape of his hand, and whimpered desperately as she felt his knuckles stretching her open as he tried to force his way deeper. Another hand joined the one trying to enter her and began stroking her clit, which caused her body to quiver a little, and she could feel her vaginal muscles trying to squeeze the fingers inside her, which was not making it any easier for the man to get inside her. She let out another muffled grunt of protest as his knuckles continued to push up against her tight entrance.
To her left the athletic blonde let out a strained cry of pain and yelled out “Virgil!”, obviously deciding that she was not ready to allow this to happen to her. She wondered if Sam would be disappointed. From her current vantage point, on her back with a man blocking her view with his crotch, she couldn’t see where he redistributed himself to, but assumed that he would pick one of the other two women. Of course that meant that with another sacrifice tapping out, the number of men surrounding Tegan just jumped from seven to nine, and she found herself on the verge of panic as she feared that they might all want to take turns trying to insert their entire hand into her cunt.
At that moment though her wandering thoughts were shattered by a sudden pressure that told her that the man’s knuckles had managed to clear the tight entrance to her body and she groaned as he balled his hand into a fist inside her, her muscles clamping down and squeezing his hand for all they were worth. She had a fleeting recollection of her brief affair with Bethany and the way her vagina had formed a tight seal around her wrist once her hand had slipped inside, and imagined that this had just happened to her. She felt her stomach lurch as if she was about to be sick and groaned as he continued to push into her, the oddly shaped mass of clenched fist forcing her little tunnel wide open until she could feel his knuckles against her cervix. She arched her back breathing hard, still pinned at the shoulders by the men either side of her, thrashing her head to the side as she tried to process what had just happened.
Then, she realised she was shaking, her hips trembling as the man held his fist in place. She had an unnerving feeling like she needed to pee that wasn’t going away as the man’s hand put pressure on her insides in a way that was completely new to her. She tried to hold back that feeling but the man started to move his fist back and forward and she could feel muscles being pulled and twisted as he moved his hand inside her aching cavity, and she couldn’t hold back. She tried to pull her thighs together but couldn’t because of the way she was bound. She felt the pressure building in her crotch release all at once as she let out a strangled moan, breathing hard through gritted teeth as she experienced one of the most unique and intense orgasms of her life. She felt again like she might have wet herself but wasn’t sure and at this point, didn’t care. As she lay breathless and shaking on the table, still impaled on the man’s fist, she heard a voice somewhere behind her cry out “Virgil” and by her estimation the petite Asian woman had just tapped out. Tegan wondered if she had tapped out because she was unable to take what they were trying to do, or if they had succeeded and she had quit because it was too much for her. Maybe Sam would know. As she heard the sounds of men moving towards her Tegan reflected on the fact that that meant that she and the emo girl likely had more than ten men each for whatever the next circle offered, and that was just her assuming that this ordeal was over with.
The man began to pull his hand out – and it seemed like he was trying to remove it, not just move it around inside her – and she panted with the sensation of feeling his hand tug against her as her body resisted the sensation of feeling such a large, irregular object exiting her vagina. She imagined childbirth was a million times worse but still, this was the closest she’d ever gotten. A groan of relief escaped her as the widest part of his hand finally cleared the muscular entrance and she felt her battered fuckhole relax and begin to shrink closed again.
“Now that the sacrifices have been reminded that their place is to suffer for our amusement and pleasure, we are ready to move onto the final round. But crossing into the ninth circle is not easy, and we have an additional challenge. A kind of tiebreaker, since we still have more than one survivor.” The speaker said. His tone was even, maybe slightly amused, but Tegan didn’t detect any malevolence in his tone. Tegan was reassured that it was all part of the game as she was unbound from her restraints and the spreader bar and her wrists were untied again. She was lifted carefully from the table and led – half carried – towards the centre of the room. Someone gently removed the leather bit from between her teeth that she’d been biting down on for so long she’d forgotten about it.
The emo girl was likewise being assisted on wobbly legs and they faced each other directly for the first time. The other woman scanned Tegan up and down, her expression seemingly impassive. Tegan scanned her in return. She was so pale she nearly glowed. Her black hair surely had to be dyed. Her eye makeup was smeared everywhere. In terms of her body she was skinny but had broad hips, and large, heavy breasts. Her pale nipples pointed down slightly, swollen with a slight pink flush. Her pussy was shaved bare and the most colourful part of her otherwise monochromatic body, inflamed with the night full of sex and other abuses of their genitalia. Between them had been placed a bench, and at each end was the largest dildo Tegan had ever seen.
The dildos were a large alien shape, tapered and smooth at the tip with an almost flared cockhead shape but quickly bulged outwards in an elongated curve. It had to be at least a foot long overall but it’s girth at the widest point would easily be as large as a man’s clenched fist, before taping back to a narrow point at the bottom almost like a comically oversized buttplug. After assessing it she looked back at the other woman to gauge her reaction and was relieved to see a hint of anxiety pierce her placid mask.
“Now, my angels, before you panic – this is not an elimination challenge.” The speaker stood next to the bench, addressing them both. “You may choose to participate, and to what extent. It is a challenge. The sacrifice that can take more, aha, punishment… will have earned her place in the ninth circle. The loser will have to perform an additional challenge.” He half turned and gestured to someone who came forward holding a large vessel a tall glass flask that was unmistakeably three quarters full of semen.
“Is… is that cum?” The emo woman asked incredulously.
“Yes, my dear.” The Speaker answered. “A little over a litre of it, generously donated by our demons. You may have wondered why none – or almost none of them – shared their emissions with you over the course of the evening. It was building to this moment.”
“So, the angel who… can’t take as much of that…” Tegan pointed at the dildo “…has to drink all of that?” She pointed at the glass flask.
“Correct.”
“And that’s just to get to the final round?”
“Alternatively you can refuse, call your guide to you, and leave – and leave the last angel to face her fate alone.” The Speaker said pleasantly.