Family Estranged Ch. 05

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As the depravity reaches a climax, Charlotte has regrets.
3.7k words
4.64
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Part 5 of the 9 part series

Updated 01/01/2024
Created 12/01/2023
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"Hold back and I'll know, bitch. Hold back and your daughter will be JOINING you. Got it?" Ben growled.

'I have to do this for Sky's sake,' Charlotte thought, hating how much things had spiraled out of control.

With tears leaking down her cheeks, the gorgeous, gagged, and busty MILF nodded. With her hands cuffed in front of her, the beautiful mother crouched over the nearest dildo. Then, dreading the sensations to come, Charlotte decided to just get it over with. She slammed her slick snatch down the entirety of its girth in one swift plunge. Her cunt immediately felt a riot of stimulation as the ribbing on the dildo awoke the nerve endings up and down her pussy. For the first few seconds or so, it felt all right. More than all right. For the first few seconds, it felt positively good as that ribbed dildo rubbed against the sides of her aroused sex.

But then the hot sauce kicked in. Fresh tears sprang from Charlotte's eyes as the busty MILF felt an unbearable heat flaring between her legs. She was reaching down already, her cuffed hands pressed to her pussy, her fingers rubbing her clitoris fervently while she humped the dildo. But the agony tore through her, heat sizzling inside her cunt as she bounced on the shaft, as her insides screamed and fire slithered through her loins.

"UGGGGHHHH!!!!! UUUUUUU!!!! PLS!!!!!!!" The red ball-gag mostly contained her muffled shrieks as the gorgeous blonde humped the pink dildo.

Ben looked down with satisfaction as the poor woman rubbed her clit to stoke pleasure to counteract the pain, her breasts bouncing with the enticing rhythm he'd hoped for as she violently impaled her sex on that unyielding pink monstrosity.

"Not bad, Mama. Keep it up. Show that pussy who's boss now. That pink cock is your new Master right now. I want to see those cunt lips kissing the base, hitting those pink testicles, each time you fuck yourself. No going easy on yourself, bitch. Not unless you want your sweet little girl to join you."

Squeezing her eyes shut with a wail, Charlotte maintained her appalling exertions. Her cunt lips slid down the entirety of that awful pink manhood with each and every impalement. And with each and every impalement, just as the ribbing abraded the insides of her cunt, so too did the hot sauce make Charlotte's pussy feel as if it was being engulfed by an inferno.

Contented with the show that Charlotte was putting on, Ben turned back to survey the rest of the action.

With a groan, Zane was finally starting to come to, cuffed to his chair. Meanwhile, Skylar's exertions were going strong. The slender blonde's butt cheeks were rising and falling at a steady tempo as she impaled her own pussy on J's eager shaft. Each time she slid up on him, Ben could see the telltale fluids coating J's cock, that fleshy spike glistening with both J's pre-cum and his victim's cunt juice.

"Now this is what I call special. Now this is what I call a party," Ben boomed.

He walked over just in time to see Zane's bleary eyes open. The young man took a few moments to understand his surroundings, to realize that his ankles and wrists were cuffed, that he was completely naked, immobilized, and helpless. Then his eyes widened. All at once he saw this horrific scene: his naked mother, gagged and cuffed, humping a giant pink cock and shrieking, his naked sister hugging a man and sliding her pussy down his cock like a nympho-maniac while moaning, and his girlfriend naked with her wrists cuffed in front of her looking like a deer in headlights.

"Wakey, wakey, lover-boy. You thought you were going to have a nice, intimate night with your hot-piece-of-ass girlfriend, but tonight you're going to get more than you bargained for," Ben gloated.

"Uhhh! You...you sick son of a bitch... what are you doing?"

"What's it look like? Teaching your family the joys of sexual bliss. Now... I think you want in on this action, my little bitch-boy. Am I right?" Ben jerked his chin toward the seat of Zane's chair. Although his shaft was flaccid right now, even at its fully elongated length it couldn't have been more than a good six or seven inches - paltry compared to the rigid cock of the rapist who now loomed above him. "Looks like we need to wake up your little you, don't we now," Ben mocked. His gaze slid toward Mia. "Maybe your girlfriend can help with that."

Now the assailant stalked over to the bed.

"Please, don't hurt us!" Mia babbled. "I'll cooperate. Look, I won't resist. I'll -"

SLAP. The slap stung Mia's cheek and she rocked back on her heels, nearly sprawling back onto the bed.

"If you want to cooperate, you'll shut the fuck up and do exactly as I say," Ben hissed. He now grabbed Mia by the nape of the neck and thrust her forward, then thrust her onto her knees at Zane's feet.

"You see anything you like, little slut? I'd get busy if I were you."

With a shudder, Mia leaned forward. Tenderly, she began to traipse her tongue up and down the sides of her boyfriend's shaft. Then she swirled her tongue just around his glans, her cuffed hands gently cupping his balls. Soon Zane's manhood sprang to life. Soon Zane was groaning. Mia now bathed the top of his penis in her saliva, her little pink tongue flicking and caressing him.

"Uggghh! You sick bastards, you won't get away with this," Zane huffed.

"Keep him hard, bitch. I want you licking and teasing and sucking on just the very tip of that cock, but that's it. I don't want him coming yet. Understood?"

"Uhhh. Y-yes."

"Yes WHAT?" Ben barked, yanking her head back by the hair and glaring at her.

Mia wracked her brain and remembered what Skylar had called the other intruder.

"Y-yes, Master."

"Good girl." Ben let her resume her cock-licking and tender sucking on just the top of Zane's shaft. She sucked on that tip like a lollipop now, her lips forming a seductive shape around the contours of her boyfriend's penis.

Now, Ben stepped back and walked up behind Skylar, who was cooing and moaning, sliding her pussy up and down J's shaft, kissing him, practically mauling his face with her lips.

"Mmmm. Yes, you little whore. Slide that wet pussy down my cock. I'll fill you soon, bitch."

"Yes, Master. Please fill me," Skylar panted, just hoping it would end soon despite the pleasure ricocheting through her vaginal walls as the delicious friction of that cock sawing in and out of her sent a traitorous and alarming libido surging through her.

But Skylar wasn't prepared for what happened next.

Suddenly, she felt a strange pressure against her tighter, wrinkled hole.

"Mind if I share this bitch with you?" Ben said.

"Not at all, Brother," J replied.

'Oh no! NO!' Skylar thought frantically. She felt Ben's warm body pressing against her back as he lined up his cock with her ravaged anus and began to push.

"Please Master, you've already ass-fucked me! Pleeeeaaase!" Skylar squealed.

Ben ignored her pleas, though, just enjoying the sensation of his shaft sliding up into her ruined anus. "Aaaahhhh fuck, bitch, you're still tight even after I stretched your cute asshole and left a big load of cum. Now it's time for an encore. Ever had both your holes filled like this, little slut? I bet NOT. Well just shut up and enjoy the ride."

"Oh god! Oh god!!! FUCK!" Skylar wailed. "Please, go slower Masters. Oh please!" After a time, though, it became easier. The constant friction of both cocks sliding through her, the shared nerve endings between her pussy and ass, began to stoke a strange kind of hunger inside her. The more those two shafts reamed her tight holes, the more she accepted and even welcomed the bombardment of stimulation...the more she accepted her fate.

"Uuuuuhhhh!!!! OH god! Fuck me, Masters. Fuck my sore holes. Please fuck me!" she begged at last, hoping to please them while succumbing to the strange, surreal barrage of pleasure despite the reawakened ache in her ass and the hyper-sensitivity of her swollen clit and pussy getting pounded by hard cock.

Then it claimed her like a predator tackling its prey. She groaned as the orgasm from the double penetration swam through her, infusing her with a cruel pleasure that obliterated her mind and left no room for anything except exquisite euphoria. Her naked figure trembled in the meat sandwich between her captors, her cunt twitching and spasming, clamping up with gratitude on J's raping shaft.

"You just CAME, didn't you, you little slut? Fuck, this bitch likes getting raped! Aahhhhh!!" J moaned.

And soon, her holes took both her captors with her. Soon Ben was growling an orgasm of his own, a fresh surge of jism shooting into the slender blonde's bowels. J cried out, clutching the back of Skylar's head and slamming her face against his shoulder. The girl could barely breathe as she felt his scalding cum shooting up her pussy, promising a second chance at an unwanted pregnancy. Skylar's hands clung to her rapist's back as she felt the thick ropes of seed hit her in waves, their pulsing heat racing toward her womb. Finally, the poor girl felt both her captors' cocks twitch their last, her insides viscous with their millions of sperm.

"Please... no more..."

As Ben stepped back and J released her, the exhausted girl sank to the floor and turned onto her side, curling up in a fetal position. Lying there, panting, the naked blonde could slowly feel all that spunk oozing out of her ass and pussy to stain the carpeting. J retrieved a pair of handcuffs and cuffed the girl's wrists behind her. She just closed her eyes now, looking more dead than alive, and lay there, limp, yearning for a reprieve from the attentions of her savage captors.

Meanwhile, another pinnacle was fast approaching on the other side of the room.

Charlotte had finally managed to do the seemingly impossible. The burn of the hot sauce had at last abated to something tolerable. This entire time, the busty MILF had kept plunging her pussy down the ribbed dildo, rubbing her clit and stroking herself toward bliss. Her cunt's juices began to dilute the awful sting of the hot sauce, and now a true measure of joy snuck through her, true sexual pleasure spiking each time her pussy sank down onto that unyielding pink penis.

"UUUUGGGHHHH!!!!! UUUUUUH!" Charlotte moaned. Both men now looked at the busty blonde as her anguished face reflected not just the sting of the hot sauce but genuine pleasure, a buildup toward a furious climax. Her welt-covered breasts now sported two fully aroused nipples.

And then it came.

With a muffled shriek, this time of ecstasy rather than agony, the beautiful mother came hard on the pink shaft, her cunt's fluids rushing down the sides of the shaft as she continued to impale herself. Her neck snapped backward as she shrieked toward the heavens, her pussy clamping around the ribbed dildo as if yearning for it to be a real cock, her juices soaking and coating every inch of that dick as if in eternal gratitude.

With a groan, then, Charlotte pitched forward and lay still.

'Oh god,' Charlotte thought. 'What have I done? I thought I'd vetted these two, but they really are psychos. They're taking this too far. I just wanted it to be me and Skylar... now they've taken Zane and Mia too.' She yearned to utter the safe phrase through her gag, but even if she'd been able to say something halfway intelligible, now Charlotte wondered if the the two monsters would even listen to her.

And soon enough, Charlotte got confirmation of just how depraved Ben and Jayden could be.

"Well, isn't this nice. You made your boyfriend's cock nice and HARD. Well done, bitch," Ben said to Mia. "Now why don't you clean my cock. It's been in the young blonde's tight ass, and it's looking a little dirty."

Mia gaped with revulsion at Ben's bobbing, semi-flaccid cock as he strode toward her. It was sheened in remnants of oil and cunt juice and blood and other substances unmentionable.

"Oh god, please, this is sick. Don't make me--" But before she could finish the sentence, he already was prodding the bulbous tip of his shaft at her lips. With a whimper, Mia took his cock into her mouth and began to suck on it, looking up at her captor fearfully to make sure that he was pleased with her efforts. Ben rested a hand in her silken-soft hair and sighed with contentment as he raped the girl's throat. Next he slipped his hand downward to cup the back of her head and impaled her face on him harder now, relishing the gurgling sounds she made as he stuffed her throat even more ruthlessly with his cock.

"Don't worry, bitch-boy, we'll teach your girlfriend how to suck properly. I'll have her happily drinking my piss by the time I'm done with her," Ben mocked. Meanwhile, Zane glared at their captor with unalloyed hatred and a promise of revenge. Though Zane didn't say it, he didn't need to - the daggers coming out of his eyes said it all. 'You'll pay for this,' it said. 'You'll pay if it's the last thing I do.'

Zane's horrible ordeal was far from over, though. In fact, it was about to worsen in ways even more unconscionable.

"Hey, Brother, I have an idea. It's my turn to be creative," J said. With a gleeful but sadistic look in his eyes, he dragged the exhausted young blonde to her feet.

"Wakey, wakey, bitch. You thought you deserved a rest, but you're not quite there yet. You've got one more job to do before I let you lie down," J said. He began to hustle the poor girl toward the chair where her naked brother sat, his erection stiff as a flagpole.

"Wh-what-wait? Wait! What are you doing?!" Skylar protested. But part of her already knew. That sinking feeling in the pit of her stomach told her that her ordeal was about to get much worse, even though she hadn't thought that was even possible.

"I think you need to comfort your dear brother, little slut. You comforted Mama earlier. Well now it's your brother's turn. Hop on now, bitch. Bust that pussy on your brother's helpless little cock."

"PLEASE! NO! This is WRONG!" Skylar wailed. But despite her struggles, it was no use. J manhandled her onto her brother's lap, forcing her to straddle him. With her wrists cuffed behind her back, she tried to push herself backward, but she was too weak to overpower the musclebound rapist.

"Let's get that pussy wrapped around your dear brother's shaft, bitch. I want to hear him groan with your snug little fuck-hole squeezing every inch of him," J growled. Now, he forced Skylar's cunt in position. She kept squirming, kept wiggling her hips enough to keep her cunt from being lined up properly with her brother's cock. Finally, though, J just slapped her hard, stunning her for just long enough. Then Skylar felt it. She felt the ultimate taboo shattered. The slender blonde felt her pussy sink onto her brother's manhood, encasing it in her soft, tender flesh. She felt her clit resting against her brother's flesh as she leaned forward. Now she watched with horror as J had his handgun clenched in his fist.

"Start fucking that cock, little slut, or you'll watch your brother die," he warned. He smacked the butt of the gun across Zane's forehead, startling him but not causing any real damage. But the threat was all the motivation Skylar needed. It overran her revulsion, and she began to grind her hips. The beautiful naked blonde began to fuck her brother in earnest, pumping her cunt up and down that fully aroused shaft.

J and Ben both enjoyed the taboo display which followed. Skylar's and Zane's anguished groans seemed to meld together, her ass cheeks bouncing as she rode him, as she violated the ultimate representation of the forbidden, her own pussy gripping her brother's cock. But feminine and masculine instinct cared little for terms like 'brother' or 'sister,' and the look of lust on each of their faces soon proved undeniable.

'Oh god, I'm so sorry, Z.' With that thought pounding through her head, Skylar closed her eyes and just prayed it would all be over soon. She arched her back and rode him like a slut in a porn film.

Soon, despite Zane's attempts to hold back, he found his excitement growing. Lust pooled in his loins and made the seed in his balls churn with need. Soon, despite Zane's best efforts, a prominent few streams of his pre-cum, along with J's leftover sperm, had escaped the tight seal of his sister's cunt lips and made inevitable progress, oozing downward with gravity's help, until glistening white fluid had slid all the way down to coat his own balls.

At this point, Ben finally let Mia come up off his cock. The girl coughed and spluttered, horrified by the sight of her boyfriend now getting fucked by his own sister.

"Doesn't that look hot and romantic, bitch? I bet you're jealous though, huh?" Ben mocked. "Tell you what. Here, you can get in on the action. Let's have you suck those fluids off your boyfriend's balls."

Forcing her head downward, Ben made her do just that. Mia's groan of protest went unheeded, and soon the sounds of her sucking up pre-cum and jism from her boyfriend's testicles was followed by more sounds of gentle licking and slurping while she tenderly sucked on those wrinkled folds, lovingly taking each of those sperm-filled balls between her lips.

"Mmm. That's it, little whore. Keep sucking on those balls while your boyfriend's sister gives you a lesson in how to fuck him. I hope you're taking notes," Ben said, his tone jeering and cruel. As if to add insult to injury, now at that moment Skylar couldn't control it - she felt a climax steal through her unexpectedly. The naked blonde moaned on her brother's lap and hated herself a little more. Keeping her balance though, despite her hands cuffed behind her back, the slender girl managed to continue grinding her wet pussy on her brother's manhood. Yes... her pussy was so wet, to her eternal shame. The sensations Zane's cock was giving her would stain her soul. The pleasure she was giving him was just as appalling though. Zane looked up at her with tortured eyes.

"Sky, it's OK. Uhhh! I forgive you."

Yet as Skylar's cunt squeezed the length of her brother's manhood, that forgiveness remained cold comfort. She even caught him staring at her breasts before he looked away.

'Oh god, please make it stop. Please just come, Z. Just get it over with,' the slender captive begged inwardly. Did her bastard of a brother need encouragement in order to finish? While she sank her pussy once more onto his shaft, she moaned, "Please Z, cum. Please cum."

This would be a shame she could never, ever outlive.

Meanwhile, Zane closed his eyes and the thought hit him with utter self-loathing, 'My sister is beautiful. She's so beautiful.' Even with his eyes clenched shut, the older brother couldn't get that sight out of his head now - his little sister's nubile figure riding him, the sensation of that cunt clamped around his manhood. 'I hope Mom's not seeing this,' Zane thought with despair. And yet inwardly, the primal, id-based masculine voice inside of him urged, 'Fuck me, Sky. I want to feel every inch of your pussy squeezing my cock. Oh god... yes. Yes!'

While Ben kept a close eye 'supervising' their three younger captives, J now strode over to the mother. Charlotte lay there still panting, her pussy still aching from the hot sauce despite the fog of residual pleasure from her orgasm.

J crouched over her and grabbed her by the hair, forcing her to look at the rape in progress across the room. Forcing her to look at her beautiful daughter's ass cheeks resting on her son's lap, that cock vanishing inside Skylar's soft folds.

"Well, Mama? What do you think? Look at your son and daughter having a good time. Did you get your money's worth?" he whispered so that only she could hear.

'Oh my god. What have I done?' Charlotte screamed inwardly. Now she realized the truth despite what tatters of misguided sanity still clung to her mind. 'I've unleashed something I can't control. These men... I shouldn't have trusted them. Oh god. Noooo...'

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