New Jack Ch. 11

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.

11.

Jack and Allison decided to take a dip in the pool after Debbie left. Since Allison didn't have a bathing suit Jack volunteered to apply sunscreen which he did very thoroughly. She reciprocated, taking enough special care that his previously flaccid member was beginning to show signs of life again.

The two of them splashed in the pool, playing happily like kids. Jack was genuinely enjoying her company and it seemed to him that she was much more relaxed than she had been at lunch the previous day.

Of course the air was thick with sexual tension and when Jack grabbed her from behind to dunk her he may have 'accidentally' slid his hands over her naked breasts, the raspberry nipples grazing his thumbs. Similarly, she probably didn't need to nuzzle his cock in between her ass cheeks as frequently as she did, but Jack wasn't complaining.

They returned to the cool house after an hour or so of playing in the sun. Allison's skin didn't look like it could handle much more exposure than it had already received, and she wanted to take a shower before the party. Jack didn't think he could resist the temptation involved in showering with Allison and opted to fix a light meal of seared tuna and salad for them while she cleaned herself.

Jack had taken a quick shower of his own once the meal was ready, popping one of Max's pills, and then the couple donned bathrobes to eat at the bar area in the gathering dusk. Their conversation was very open: secrets Jack normally would have kept from others spilled out of him in response to her queries. He felt he had nothing to hide from his gorgeous neighbor and it was a liberating feeling.

Their conversation eventually turned to sex, as one might expect. Jack outlined in broad strokes his dead/dying bedroom with his ex-wife and the previous regrets he had had about never being able to live out his sexual fantasies.

"Which are...?" Allison asked, smiling.

"Hell, you're going to see most of them tonight," he responded with a mischievous grin of his own. "What about you? Anything on your sexual bucket list?"

"I want it to be about me for once. About my satisfaction. Tony wouldn't even go down on me, much less make sure that I finished whenever we had sex . Debbie's tongue is the first one that's been on my clit in over a decade." Her voice was mournful, and it seemed to Jack that she grieved the lost years. "I've always been self-conscious about my labia, and Tony's refusal to go down on me really gave me a complex."

Jack stood, pushing his barstool back and sliding their plates to the side. "Hop up," he said, "let me give you my expert opinion."

She looked a little startled but got to her feet and allowed Jack to take her robe before boosting her onto the bar. Jack nudged her thighs, forcing her to open them a bit more and he watched as her inner lips opened like a flower before him.

"Absolutely gorgeous," he pronounced, unable to wrench his eyes from the large thatch of short red hair between her thighs. "May I have the privilege of doing what your husband should have done every day?"

Allison looked embarrassed but nodded her assent. Jack leaned forward and began chewing on her areola, making a path along the flesh outside of her nipple. His hand grabbed her unused breast and began slowly but firmly massaging it. Jack's mouth continued to make a spiraling path towards her nipple before finally he took it between his teeth, pulling it away from her body slightly and flicking it with his tongue.

Allison gasped in response to the stimuli, and Jack released the nipple, repeating the process on her other breast. He could feel her breathing changing, each breath now deep and strong as desire built within her.

Finished with both breasts, Jack kissed his way down her flat stomach slowly, each kiss accompanied with a flick of his tongue. He kissed his way through her short pubic hair, veering to the left when he reached her clitoris to continue his trail of kisses up her thigh to her knee. Reaching her knee, he switched to her other leg and his mouth began its final trip toward her swollen lips.

Her hips bucked reflexively the first time his lips touched her sex and she moaned appreciatively. He took each of her outer lips into his mouth in turn, massaging them with his tongue, sucking on them, before lightly biting them and releasing them with an audible pop. Allison was growing restless, her hips beginning to gyrate on top of the bar more frequently now.

He took both of her dangling inner lips into his mouth together, his tongue darting around and between them and began to suck on them, his nose brushing her clit with his motions. Her moans grew louder now, and Jack looked up to see her pulling her nipple taut, away from her body. She twisted the thick bud and released it, grabbing the other one. Strands of her straight red hair were plastered to her neck with a thin sheen of sweat and her eyes were closed in concentration, enjoying his ministrations.

His release of her lips was met with a groan of frustration from her mouth, but it quickly changed to a guttural moan as he licked up and down each side of her large clit. He slipped one, then two fingers into her, barely able to fit the second, and her moan became higher in pitch, louder.

Sensing she was getting close, Jack closed his mouth around her clit, alternately sucking it like a little cock and flicking it quickly and lightly with his tongue, learning her preferences.

"God yes!" she wailed, "Just like that! Don't stop! Please!"

Jack had trapped her clit between his teeth, biting lightly and rapidly flicked the exposed end with his tongue. She came silently, mouth open with a scream never to be heard by mortals, offered up to the gods of pleasure. One hand held the back of his head while she hunched forwards in orgasm, the other mauling her own pale breast. Jack felt a gush of liquid as Allison's body continued to seize under his touch. His pace never wavered, and he continued his harassment of her swollen bud until she finally released his hair, slumping back.

Jack helped Allison off the bar, depositing her in a deck chair. She looked up at him, finding him grinning back goofily, his lower face and hand glistening with her orgasmic fluids.

"See why I need to clean the sheets so often?" he quipped.

She held up her hand, gesturing that she needed a minute. Finally she responded, "Holy shit. I can't believe that just happened. I've never cum like that before. I need a fucking cigarette or something."

"You sound like Debbie and Cindy," Jack replied. "I've got cigars if you want one."

"Let's do it. And I could really use a fucking drink. Vodka?" She grinned at him.

"I think martinis are in order now. You stay put and relax. I'll take care of it." His words brought a heartfelt smile to her face, as if no one had taken care of her needs in years.

He mixed basil martinis also loading the tray with two glasses of water, cigars, ashtray and matches. "So, was it everything you had hoped for?"

"That and more," she said sipping the martini and unwrapping the cigar. She stopped suddenly, looking at him. "Can I return the favor?"

"Any other time, I would love that. This one is just for you though. Seems like you needed that." His words were soft and heartfelt.

She looked at him with another genuine smile. "Thank you. I think you're right. That's just what I needed." She lit the cigar inexpertly but soon figured it out. She took a long pull from her drink and stretched her limbs, allowing the tension to flee her body. "Well, today didn't go at all like it thought," she said with a small laugh.

"It went as well as I could have hoped for," Jack confessed. "You jumped to the top of my fantasy list when I saw you at lunch. A gorgeous woman with a great book? Mmm."

Allison flashed an appreciative smile at him, "I'll admit to having some impure thoughts about you as well. But number one? With all the women you've managed to bed in the past week and all of the other kinky shit you guys have been up to?"

Jack shrugged. "I like what I like. All of that other stuff is just sex. Sure, Debbie and Cindy are amazing, but they're married and I've got no interest in breaking anyone up. So, you're top of the list. And having you participate was an unhoped-for dream," he confessed.

"I think I get it," Allison replied, but the doorbell interrupted anything else she had to say. The couple grabbed and donned their robes, Allison opting to stay with her drink and cigar while Jack went to answer the door.

Realizing that he needed to grab more towels, Jack yelled at the door, "Come on in, it's open. We're out back!" He heard the door open and close while he busied himself collecting towels before returning to the patio to find Cindy and Max standing next to Allison.

"Hey guys, glad you could make it," Jack called as he crossed the pavers to the trio.

"I can't believe Allison is here!" Cindy squealed, bounding over to him. Her breasts threatened to compromise the structural integrity of the small blue-gray bikini top she was wearing as they bounced with each of her steps. Cindy molded herself into him, grinding her hips onto his leg while pressing her breasts into his chest and locking her lips onto his.

Cindy broke their kiss but didn't release Jack. "Max, aren't you going to say hi to Jack and thank him for inviting us?"

Max looked uncomfortable but walked the few steps over to Jack and Cindy. "Thank you for having us back and doing this for us. It really means a lot," he said, his eyes not meeting Jack's.

As he spoke Cindy reached up and untied the knot of the bikini string around her neck, allowing her huge pale breasts to bounce free. The large pale pink areolas were magnets to the onlookers' eyes, and she rubbed her breasts into Jack's chest and arms.

"I thought we agreed you would show Jack proper appreciation," Cindy said, a hint of a question in her voice.

Jack was confused and looked from Cindy to Max for clarification. Allison caught his eye with a raised eyebrow of her own.

"Of course," Max said, "I must have forgotten." He awkwardly got to his knees in front of Jack while Cindy's hands tugged Jack's shorts down. Jack's cock flopped out inches from Max's face and Cindy's hand grabbed the root of his shaft, waggling it at her husband.

"Suck it bitch," Cindy said, slapping Jack's half-hard cock on her husband's cheeks and lips. Max opened his mouth and Cindy slid Jack's member into it. Jack grabbed her tits as she did this, roughly groping the prodigious amount of flesh, Cindy moaning loudly in response to his tweaking of her sensitive nipples.

Jack looked over at Allison to see her with her drink halfway to her mouth, frozen, her eyes wide. He grinned at her, "I told you that you'd see everything. Cindy," he said, releasing the blonde, "help your husband out."

Cindy sank to her knees next to her husband and began to lick Jack's heavy sack. The doorbell chimed again, and Jack again looked over to Allison. "That'll be Debbie and Bill. Do you mind bringing them back?"

Allison nodded mutely and moved to the door, glancing over her shoulder every couple of steps. Max and Cindy had switched, Max's tongue bathing Jack's testicles while Cindy struggled to take his erect cock all the way down her throat.

Debbie practically ran out the back door, followed by Bill and Allison at a more leisurely pace. "Well, well, well," Debbie said in a mocking tone, "what do we have here?"

"Max, and now Cindy, are thanking Jack for having them back," replied Allison, as if this were the most natural thing in the world.

"Bill, you should thank Jack too," Debbie commented, stripping the top of her bikini off. "I think it's only fitting that you show as much gratitude to Jack as Max does."

Cindy and Max stopped their oral ministrations, rising and making room for Bill. Bill kept glancing at Allison and hesitantly made his way to Jack, sinking to his knees before the larger man.

Debbie followed her husband, melting into Jack as Bill's mouth descended over his erect tool. Jack's right hand went to Debbie's tits, his left slipping beneath the fabric of her suit to grope her ass.

Jack looked over at Allison who stood transfixed, watching yet another of her neighbors slurp on Jack's cock. "Come on over if you'd like a closer look," he said with a mischievous grin and Allison started, but quickly composed herself before stepping next to Jack.

Jack slipped a hand into the top of her robe, fondling her large pale breast, fingering her thick nipple. "What do you think?" he asked her, both hands on the tits of different women.

"That's so fucking hot," she breathed. "Do you ever cum in their mouths? Have you fucked them?"

"I've got no interest in fucking them. But I do cum in their mouths if I feel like it," was Jack's easy reply.

"Fuck me," Allison said, breathing heavily. "I had no idea this would turn me on so much."

"Oh, you're definitely going to get fucked," Jack added with a chuckle. "But not before these cucks do what you want them to. Care to let them in on what's going to happen? It's your show now."

Allison's eyes burned with lust at his words. "Stop sucking cock you faggot," she said to Bill. "Here's the deal. Bill and Max, you guys are going to strip right now," she said, her words hard. The men began removing clothing as Bill stood up, relinquishing Jack's glistening member. "That's it boys, get those tiny cocks out for all of us to see."

Bill and Max finished removing their clothes and stood before the women and Jack. Cindy had moved to Debbie's free side and the trio of women and Jack regarded the two naked men before them. Bill's erection was evident, already leaking precum from its small tip. It was harder to tell with Max, but it looked like he was already hard.

"Pathetic," Allison scorned, "both of you. Get into the bedroom now: we're going to give Jack a reason to make Debbie clean the whole damn room."

The group followed the two nude men into the house, Jack losing his shirt along the way, his last article of clothing. Debbie and Cindy similarly left their suit bottoms outside leaving Allison as the only person clothed.

"OK," said Allison, clapping her hands. "Here's what's going to happen. I originally wanted to see you guys fuck each other, but I don't think Max has the equipment to make it worth my time. So, Bill is going to fuck Max while Cindy jerks Max off. Max," she said, turning to the portly man, "you've got to let her know before you cum. I don't want her to touch any of your pathetic seed."

Bill flushed deeply at this, but Max's embarrassment was complete. "Bill is going to cum in your ass Max, but then he's going to eat your cum off the floor," Allison continued. "If you do a good job, then Max will be allowed to direct the activities of Jack and us ladies while you jack each other off. How's that sound cucks?"

The husbands hesitated before nodding mutely, not looking at each other. Jack looked at Allison appraisingly, impressed. She had a dirty mind that he could respect, and it turned him on even more.

"You're delightfully wicked," Jack murmured into Allison's ear. "I love it."

"Can I make a request?" Bill asked hesitantly.

Jack cocked an eyebrow at him. "What is it?"

"Can you guys play while we do this? It'll help us put on a good show." Max's head bobbed in agreement with Bill's statement.

"What do you have in mind?" asked Allison guardedly.

"Will you fuck Jack while we watch?" asked Bill timidly.

"And make Cindy and Debbie 69?" added Max quickly.

"No, Cindy's going to rub your tiny pecker for a while until you cum with a cock in your ass," responded Allison coldly. "But I'm OK with the other request, and I'm sure we can find something for Debbie to do."

Cindy looked at Jack, frustrated. "Why do I have to do that? I don't want to. I want to play with you guys."

Jack moved quickly, pulling her over to the bed with him where he bent her over his knees again. She tensed once she realized what was happening. "Cindy occasionally has some difficulty following instructions. Sometimes she does it intentionally though," Jack said, looking at Allison.

His left hand mauled her hanging tits while his right hand caressed the broad expanse of her pale ass. "The dirty slut loves it though," he said, and his right hand began to raise and fall quickly, slapping the luscious white cheeks of her ass. His handprints were immediately visible on her pale flesh as his slaps sent ripples through her cheeks. He could feel her abdominal muscles clenched beneath the soft flesh of her stomach atop his thighs, and he added an occasional slap to her hanging tits.

Cindy howled beneath his assault, her hips beginning to writhe as she tried to get away. Allison looked shocked while Debbie looked on, biting her lip. Bill and Max had both began rubbing their cocks as Jack continued to discipline Max's wife, relenting only when Cindy's ass was covered with a bright red hue.

Cindy continued to whimper slightly as Jack released her, both standing. "Are you sure she likes that?" Allison questioned quietly.

"Come here, I'll prove it," Jack responded before turning to Cindy. "Spread your legs and bend over."

Cindy's whimpers had stopped, and she complied with Jack's orders, her shaved pussy and small lips clearly visible as she bent over and touched the floor, displaying herself to Jack, Allison, and Debbie.

"Check for yourself. See how wet she is now," Jack said to Allison. "I bet I can make her cum just from spanking her."

Allison looked doubtful, but Jack cocked an eyebrow and grabbed her hand, pulling her directly behind Cindy.

"Do you like this, you fucking slut? Spreading yourself for us, waiting to see if your friend will put her fingers in you?" Jack's voice was a hoarse rasp, and Cindy groaned in response. "Say it," he continued, "or tell me I'm wrong."

"I love it," came Cindy's muted voice. "Make me cum, please. I'll do anything."

Jack guided Allison's pale hand to Cindy's sex and slowly pushed Allison's two extended fingers into her friend's dripping hole.

"Holy fuck she's wet," gasped Allison in awe. "I had no idea."

"Keep your fingers in her. I'm going to make her cum now." Jack grabbed Cindy's shoulders and pulled her up so that her face was even with his cock. "Put it in your fucking mouth," he growled.

Cindy complied, and Jack pushed his cock as far in as he could get it. He could feel Cindy's breath coming from her nose onto the base of his cock as her tongue struggled around his thick member. He reached down with his left hand grabbing her right breast roughly, pinching the nipple hard. Cindy groaned around his cock before nearly choking as the blow from his open right hand landed on her upturned backside.

Allison moaned with Cindy. "May I?" she asked Jack, her unoccupied hand in the air.

"Of course," Jack replied nonchalantly and watched as Allison smacked Cindy's other cheek hard. Cindy's body bucked with the violation and Jack and Allison took turns slapping the buxom blonde's ass until Cindy seized in orgasm, howling around Jack's cock and bucking her hips against Allison's exploring fingers.

Cindy stood shakily before kissing Jack deeply. "God, I needed that. That was fucking perfect," she murmured.

Jack gave Allison an 'I told you so' look to which she responded with a bemused look of her own. "That wasn't the bet though," she said defiantly.

"I know. Let's get that going though." Jack's words turned the women and himself back to the men. "All right boys, let's do this. Max, get on all fours. Bill, catch," Jack tossed him lube from the nightstand.