New Jack Ch. 12

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Jack pushes his own boundaries.
5.5k words
4.62
17.9k
4

Part 10 of the 11 part series

Updated 06/08/2023
Created 05/02/2018
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This story contains pervasive same-sex action, cuckolding, and rough sex. If that's not your cup of tea, please feel free to pass over it.

If these things do tickle your fancy (or something else) please leave a comment or send me a message: I'd love to hear what you think.

12.

Everyone migrated to the kitchen, congregating naturally at the island. The trio of women eschewed the barstools, opting to stand as they chatted merrily. The wives had forbidden their husbands from getting dressed, the two men stood back a few paces, awkwardly, with their hands crossed over their respective groins.

This simply won't do, Jack thought to himself. "Bill, Max," he called aloud, "why don't you make us some drinks. I'll have a Hendricks martini, straight up with a twist. Ladies?"

As the women barked their drink orders at Bill and Max, Jack moved behind Cindy and nestled his half-hard cock into her still-flushed ass cheeks as his hands reached around and hefted her prodigious breasts. "So, Max," Jack began, "tell us what you have in store for us."

Jack was rolling Cindy's pink nipples between his fingers when Max turned to address him. Max's eyes widened as he watched Jack fondle his wife, and the pudgy man gulped several times before he managed to answer.

"I, I, I want to see you make my wife cum by fucking her in the ass while Allison goes down on her," Max stammered, averting his eyes.

"Indeed," Jack replied in a gravely voice, "that would be a sight, and I don't blame you for wanting to see that. But you know," Jack continued, "that you'll have to clean my cock once I'm done with her." Max flushed but nodded his agreement. "And Cindy will be the one who gets to decide how it gets cleaned," Jack finished.

Max gulped again, the drink he had been making forgotten in his hand. After a moment he nodded again, agreeing to Jack's terms.

"What else?" Jack pressed.

Max continued to look stressed and distracted as Jack pushed his wife forward so that she grasped the counter with her hands, her legs automatically parting. Jack pushed two fingers into Cindy, eliciting a soft moan from the blonde.

Max began to speak as Jack's hand pumped into his wife's snatch. "I want to, I mean I want you to make the women line up hip to hip and bend over. I've always wanted to have my choice of pussy lined up for me." His words came in a rush but flowed so well that Jack knew this was probably one of Max's go-to fantasies.

"We can do that," Jack replied, "though we may start with that. Anything else?"

Max shook his head and seemed to finally remember the half-finished drink in his hands. Jack removed his soaking fingers from Cindy's tight pussy and she groaned in frustration. He stepped to his left, Debbie his next target, and she spun to face him, her back against the bar.

Jack's wet fingers pushed their way into Debbie's mouth as their eyes held each other's. His free hand fell to her breast, massaging, tweaking, and she moaned softly around his fingers. As Debbie's tongue danced between his fingers, tasting Cindy's juices Jack's trance was broken with Cindy's voice.

"And what else Max? I've seen the porn you watch. I know that you want Jack to fuck you," she declared. "Am I lying? Or was Bill's cock enough for you?"

Jack's face was impassive as Max seemed to shrink into himself, hunching his shoulders involuntarily and not making eye contact with anyone. Jack had wondered if it would ever come to this, if he would be asked to fuck another man. He wasn't attracted to other men, but if this was the price of using the man's wife in any and every way that he could think of then he would pay it.

Max finally seemed to gather himself. "Yes, I want Jack to fuck me and you in the ass," he said to Cindy before turning the group at large. "Forget the other stuff. I want you to bend us both over and fuck our asses. Make us both truly yours. Show us how much better you are than me in every way. Take my wife as you want, in any way. Make me your bitch."

Max's admission seemed to embolden him and by the time he was finished his words were clear and strong, his eyes flicking between his wife and Jack.

Jack regarded the man for a moment while his left hand continued to fondle Debbie's breast, his right having fallen to her hip. "What about you Bill?" Jack asked, directing his attention to Debbie's husband. "Is that what you want too? For me to fuck your ass?"

"Yess," Debbie hissed into his ear, leaning into him. Bill was nodding, eyes downcast as Max's had been.

"Tell me then," Jack demanded. "We have to hear all of it."

"Fuck me, fuck us," Bill said, indicating his wife who was now grinding her cunt onto Jack's leg. "Do it exactly like Max said. Use us both, dominate us, take whatever you want from us."

Jack looked at Allison who had been quietly sipping her martini, taking in the entire scene. "It would be hot," she confessed. "Though it makes me jealous that I don't have a dick," she said with a tinkling giggle.

"Give me a minute, we may be able to help you there," Jack said with a grin as Allison's laughter was cut short by a look of confusion that settled on her face.

"First though," Jack said "I have to let everyone know the terms if this is going to happen. If I do this, then there will be more alone time that your wives will spend here and with me in general. This means one overnight per week, one weekend a month, and one week per year your wives will be mine to do with as I see fit." Jack's voice was conversational but brooked no argument. "Also, each of you will be responsible for cleaning my cock before I move on to the next couple. Do you agree?"

Max and Bill looked at their spouses, then at each other before nodding their assent. "Ok then," Jack said, settling the matter. "Bill, you live closest. Run home and get the toy and lube that you bought the other day and bring it back for Allison."

Allison's eyebrows shot up nearly into her hairline at this last statement, but she did not question the directive.

Jack released Debbie as Bill slipped out of the room to dress. "I'm going to need a fucking drink," he sighed. "Max, go clean yourself in the shower. Shave too. I'm not fucking a hairy ass tonight" Jack commanded. "Cindy, feel free to help him if you'd like to."

Cindy and Max departed in the direction of the master suite, heads together in whispered conversation.

Jack poured himself another martini and quickly downed the bitter concoction before turning to the two remaining women. "Shall we make ourselves comfortable while we wait?" he suggested, waiving at the new couches in the living room.

Allison and Debbie drained the rest of their cocktails, setting the glasses on the granite counter before following Jack to the sitting area. "So, Allison," Jack began, "you want to try fucking with a cock, eh?" he asked, waggling his eyebrows.

"I do," she said confidently, sinking into the supple leather, flinching slightly as the cool material touched her uncovered skin.

"It's definitely different," Debbie opined, "but I kind of liked it."

"Bill may be asking for it more often once Jack gets done with him," Allison noted. "It seems like both he and Max really want this."

"If his porn habits are any indication then he does," confirmed Debbie. "Honestly, I was a bit surprised to see him suck and swallow Jack so readily. I guess he knows what he wants though."

"Ever had someone cum while they eat you out?" Jack asked Allison, abruptly switching tack.

"Can't say that I have," confessed Allison, a bemused look crossing her face. "But I'd be happy to try it out. What'd you have in mind?"

Jack's response was to grab Debbie, pulling her to him roughly, and locking her in a fierce kiss. His right hand groped between her legs, palming her sex while he twirled his left hand into her hair. He slid two fingers between her meaty lips and hooked his fingers against her pubic bone, pulling hard.

Debbie moaned into his mouth as his fingers probed her for a moment before he withdrew them, pulling her face back from his simultaneously. He stared into her brilliant green eyes for a moment before lightly slapping her pussy, causing her to gasp. Her left knee buckled inward, trying to protect that most-sensitive spot, but Jack shook his head.

Debbie's mouth was open, breathing hard as she spread her legs for him, knowing what was coming. His hand darted forward again, his wet fingers popping against her engorged lips and she yelped at his touch.

"Fuck," Allison breathed, one pale hand tracing its way through her thatch of pubic hair, a finger extending to begin toying with herself as she watched Jack's abuse of Debbie.

"Do you think she likes it?" Jack asked Allison. "Why don't you get a closer look at her face while I give her another one."

Jack pulled Debbie's hair so that her face was positioned about a foot away from Allison's, her hands on her knees, legs spread. Jack traced his fingers through her ample lips, wetting them again but enjoying the silky warmth for its own sake as well.

He saw Debbie's shoulders and ass tense as his fingers lost contact with her sex and he paused, drawing out the inevitable moment, letting her anticipation build. His other hand rested lightly on Debbie's upturned ass, fingers tracing small patterns into her bronzed flesh.

Jack glanced at Allison, his eyes smoldering. He was fully hard and leaking precum with his abuse of this pretty married brunette. His hand flew again, the blow audible, a wet slapping sound.

Debbie shrieked, collapsing forward onto Allison and inadvertently sliding down between the latter's legs.

"Make her cum or there will be more," Jack demanded harshly. "Let me see you suck her lips. Chew on her clit. Make her cum or I won't let you do the same."

Debbie's gasping mouth supplanted Allison's hand, engulfing red head's thick clit between her mouth. Jack watched as Allison's eyes widened, and she gasped, gripping the couch tightly with both hands.

"Fuck! Jesus! Ugh!" Allison moaned, her head already beginning to thrash from side to side. Jack figured he had to hurry to pull this off, so he slipped behind Debbie and quickly planted his throbbing member into her welcoming pussy.

Debbie moaned loudly into Allison's snatch as Jack bottomed out, grinding his hips against hers. He reached around, finding Debbie's hanging tits and began to maul them with his hands. He pulled her nipples down, twisting as he did so and relished in Debbie's muffled groans. He continued to grind his hips into hers, ensuring her clit was constantly stimulated.

Allison was writhing on the couch, now holding her knees up and exposing herself completely to Debbie's ravenous mouth. Jack released Debbie's nipples and pushed the back of the brunette's head into Allison's pussy.

"That's it. Make her cum. Cum on my cock while you suck her pussy," Jack's left hand continued to hold Debbie's head in place and he reached below her with his right hand and slapped her hanging tits hard, banging them together.

Debbie gave a muffled shriek and a very loud moan and Jack felt her clenching around his cock as he continued to rub his hips against hers. With Debbie's sudden outburst Allison clenched, her face a mask of concentration and veins bulging in her long, pale neck as she climaxed under Debbie's tongue.

"Nice, right?" Jack asked Allison, sliding himself out of Debbie as the latter slumped to a sitting position on the floor.

"Mmm," Allison replied. "That was new too. I really liked when you pushed her mouth onto me. That was so fucking hot."

"My pussy has never been so sensitive," Debbie gasped. "I thought I was going to cum the minute you put it in me. I'm surprised I didn't squirt."

"You may not have squirted, but you sure were wet," Jack noted, his eyes fixed on his glistening cock.

The women's eyes followed his gaze, and Jack made his choice. "Here, have a taste," he said, moving towards Allison and extending his hands to her. She took his hands and allowed him to pull her forward off the couch where she sank to her knees in front of him and next to Debbie.

Jack and Debbie watched as Allison grasped the root of his sticky shaft, pushing his cock up. She bent forward, pale tits hanging as her tongue started at the bottom of his heavy sack and traced a path up through Debbie's juices to the head of his dick. She repeated the process twice more before her mouth enveloped the head of his cock and Jack and Debbie watched inch after inch of his shaft slide into Allison's pretty mouth.

Allison's eyes closed and she moaned, her lips stretched around his fat pole. "You should know," he said, "that neither Debbie nor Cindy are allowed to close their eyes or look at anything but my eyes whenever my cock is in their mouths."

Allison moaned, her eyes now locked on his, unwavering. "What do you think, should we have some rules for you too?" Jack questioned, somewhat rhetorically given the situation.

Allison's eyes and moan conveyed her affirmative response. Jack reached down and tucked a loose strand of hair behind her ear as her head bobbed up and down before him, thinking that he'd have to discuss this more with her later. His hand slid to the back of her head and began to apply steady pressure to it, forcing her to take more of his shaft into her throat. Her light blue eyes began to glisten as he gently bucked his hips and he released her, allowing her to draw a shaking breath before filling her mouth once more.

"Good girl," Jack cooed as he began to fuck Allison's pretty face. She gagged slightly as he bottomed out in his throat but her pale blue eyes never wavered in their gaze up at him. He finally relented, releasing her, and helped her to her feet as she wiped the spittle from the corners of her mouth. He kissed her deeply, his hands traveling to her firm ass cheeks and pulling her into him.

Allison seemed to melt in his arms and Jack found himself lost in their embrace, breaking it only when Bill returned with a knapsack, banging open the front door. Jack realized that Cindy and Max had rejoined them and had been watching with Debbie.

"I've got everything!" Bill called excitedly from the door.

"Perfect. Let's go get you suited up with your new cock," Jack said to Allison, and he ushered everyone back to the bedroom.

As they filed in, Debbie retrieved the toy from the bag and knelt before Allison to begin helping her fix the strap-on into place. Jack called over to Bill, "Are you cleaned out? If not, go get in the shower."

Bill looked embarrassed, "I took care of that before Debbie got home. I had hoped..." His voice trailed off and Jack understood that he had hoped that this would happen, that he would give up his anal virginity to Jack tonight.

Debbie smirked knowingly at Jack, "Told you so," she said as she finished helping Allison and stood.

"I suppose you did," Jack replied with a chuckle. Clapping his hands once, Jack effectively called the room to order. "Since this is Max's fantasy, I think its fair that he and Cindy go first. Bill," Jack said, turning to the man but was caught off guard. Bill had donned a tiny pink miniskirt and a see-through bra. "Well, ok then. Bill," Jack continued, now composed, "you should prime your wife for me while Allison and I deal with Cindy and Max."

Debbie squealed with delight and sprang onto the bed, spreading her legs in anticipation of her husband's tongue.

"Cindy, bend over and put your hands on the bed. Max, come get me hard to fuck your wife's ass," Jack said, and he pulled Allison into himself for a kiss as Max and Cindy moved into position.

As Jack's hands explored Allison's curves Max began to lick Jack's slowly hardening cock while his hand rubbed furiously on his own inadequate nub. Breaking their kiss, Jack addressed the man servicing him: "That's it, suck my cock. Get it hard so that I can fuck your wife's ass before I fuck yours. Feel it get bigger and harder in your mouth, bigger and harder than you'll ever be, big and hard like your wife needs."

Cindy's hand was fluttering between her legs, teasing her clit as Jack spoke. Debbie watched through half lidded eyes as Bill crouched between her legs, his now-hairless ass peaking out from under the short pink skirt. Allison stroked her new cock as Max bobbed on Jack's, getting a feel for her new appendage.

"That's it cucky, stroke your little pecker while you suck on my cock," Jack berated Max. "Do you like how my dick fills your mouth? Are you imagining how much your wife likes to feel it in all her holes too? You're going to know what it feels like to truly take my cock in a minute. Or do you think you'll cum again just from having my cock down your throat?" Max and Cindy both moaned loudly at this, Max's hand now a blur between his own legs.

After a minute or so, Jack was satisfied that he was ready. "Hold your wife Max," he growled. "Hold her while I fuck her tight ass. Kiss her while she moans with the pleasure that I give her, pleasure that you'll never be able to provide. Watch her face as she takes all of my cock: see how much she enjoys it, knowing that she'll always fantasize about me whenever you're together."

Jack's words electrified Max, and he groaned with the public nature of this verbal humiliation, his hand reluctantly ceasing its rubbing of his own member as he stood and moved to hold Cindy.

Jack turned to Allison, saying, "I'm going to stretch her out for you. Pass me the lube?"

Allison grinned mischievously at him as she passed him a bottle. Jack approached Cindy's exposed ass and lubed himself thoroughly before dropping a dollop onto her crinkled star, working it in with first one finger and then two.

Cindy gasped into her husband's mouth at the intrusion. "He's going to do it Max. He's lubing me up, stretching my ass so that I can take that beautiful cock of his. I don't know if I'll ever be able to get enough of it Max, it just fills me up so perfectly."

Jack saw a torrent of emotions sweep through Max's face: lust, jealousy, and envy flashed through his eyes as Jack lined up his cock and pushed against Cindy's tight ring. She yelped as the mushroom head of his cock popped through but she began to moan lasciviously as Jack pushed inch after inch of his rod into her, stretching her out.

"Holy shit!" Cindy gasped as Jack finally bottomed out. Cindy grabbed Max's face and kissed him as Jack began to saw in and out of her voluptuous ass. "He's fucking my ass Max, it hurts so good. Thank you for letting me have him, thank you," she moaned as her body responded to Jack. Her heavy tits swung enticingly as Jack admired the ripples that the impact of his hips sent through her pale flesh. Max's hand was once again pumping his little penis furiously, and Jack began to worry that he might ejaculate soon.

Jack turned to Allison, "Ready?"

She had already lubed her toy and her blue eyes were alight with anticipation. "Fuck yeah," she breathed and moved forward to take Jack's recently vacated place. She pushed the toy in, inexpertly, but seemed to catch on quickly. Her strokes were smooth and even and Cindy began to moan in response.

"Bend over Max, hold your wife's hand while we fuck you both in the ass," Jack commanded, and Max obliged, bending over next to his wife, his sweaty hand clasping hers as she gripped the sheets.

Jack lubed himself again and dropped lube onto Max's ass as well. He wasn't keen on the idea of fingering another man's asshole, and so opted to just push in. The head of his cock popped through relatively easily, though Max grunted loudly at the intrusion. Bill must have loosened him up some, Jack mused as he pushed his rod further into Max's bowels, the latter grunting sporadically.

12