New Jack Ch. 10

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.

10.

After his morning run Jack busied himself cleaning up after the previous night's soiree. This meant he was yet again airing out the master bedroom and cleaning sheets. I need some more of these things, Jack mentally lamented, stuffing the sheets in the washer yet again. He started a group text with Debbie and Cindy, reiterating Allison's afternoon visit and entreating the women to do what they could to help him bed the red head.

Jack, freshly showered and shaved, opened his door in response to the doorbell's chime shortly after three. Allison was waiting on the step, a blue, patterned button-down blouse subtly accentuating the curves of her chest while a matching tennis skirt of dark blue highlighted her pale legs. She had fantastic calves, and it took Jack a moment to find his tongue.

"Thanks for coming: you look great," Jack said honestly as his eyes finally found hers.

For her part Allison blushed slightly, shyly, and thanked him for the compliment.

"Where do you want to start?" Jack asked. "I've never worked on a project like this before, so you'll have to walk me through it."

Allison explained that she wanted to see the house, get a feel for the space, and hear about Jack's likes and dislikes. She went on to say that she would coordinate with Debbie on the artwork selection and that together they'd ensure they came in on time and within budget.

"Sounds like you two have done this before," Jack mused.

"Many times. We're very close and have been for years," Allison replied easily, pulling her straight red locks into a pony tail. "So, let's get to it."

Jack spent the next half hour moving Allison from room to room, answering her questions. The conversation went very similarly to his initial one with Debbie. He felt a powerful attraction to the woman, and thought he picked up on an openness to him on her part.

They finished in the master suite. Allison looked at the stripped bed and cocked an eyebrow at him. "Don't like sheets?" she asked with a bemused expression.

"In the wash," Jack replied, feeling a slight burning sensation creep into his cheeks and ears.

"Debbie says you've only been here about a week. Have you already found time to dirty the sheets that badly?" Allison asked, her grin broadening.

"I like my sheets to be clean," Jack improvised lamely.

"That's a really big bed, and I have a hard time imagining that you got the sheets that dirty, that fast by yourself," she pressed.

"I'm recently divorced myself. Ironically, the storyline isn't that much different from your own. She decided to start fucking her personal trainer from the gym without talking to me first, so, yeah," he trailed off.

The silence lasted a beat between them and Jack could sense some tension in the air between them. "So, anyway, I've decided to do things my way for a while. I'm absolutely not looking for serious romantic entanglements at this point. I've learned quite a bit about myself so far, and I'm really enjoying it here. I want clean sheets, so I get clean sheets," he finished, his voice communicating his newfound confidence by the time he finished.

"Well, I'm surprised that you don't have Bill cleaning them for you," Allison said with a gleam in her eye. "You do seem to possess an inordinate amount of influence over him and Debbie," she said thoughtfully. "Even Cindy was messaging me about how much fund they've all been having over here."

"What about you?" queried Jack. "Any big plans or changes coming for you now that you're single?"

"About the same as you. There have been some things missing from my life, and I'm going to use this as an opportunity to dive in and right those old wrongs." She said this confidently, assertively, and Jack found her to be incredibly desirable in this light.

"My business is here, and my network is strong enough that I'm not going to leave," she continued. "But I think I'll find some fun anyway. I'm not looking to run out and get married or anything though"

"I'm positive that you'll find some," confirmed Jack. "This neighborhood is like nowhere I've ever heard of."

His slip hadn't gone unnoticed. "Oh?" Allison asked, her eyebrows moving up her forehead. "How so?"

"A gentleman doesn't kiss and tell," Jack replied easily. "And frankly, I'm not sure if you'd want to hear it anyway."

"No, no," Allison protested, putting a cool, pale hand on his forearm. "I'm a mature adult. I don't judge what other people do or don't do in their bedrooms."

"Well, if you really want to hear then I'm going to need a drink. Care to join me?" Jack asked smoothly.

"If that's the price of admission, then I'm definitely in. What are we drinking?" Her light blue eyes sparkled as if energized by the promise of his revelations.

"Moscow mules?" Jack questioned.

"Never had one," Allison confessed.

"Well, trying new things has gotten me where I am now. Come on." Jack offered his arm and Allison slipped hers into his, Jack grabbing his phone before the two stepped out onto the back patio into the bar.

Jack texted Debbie: Are you home?

Debbie: Yep. Need me?

Jack: Always. But I may need you to come over and prove a point for me to Allison, OK?

Debbie's affirmative response took a moment, allowing Jack to finish concocting the refreshing drinks. He smiled at his phone before looking up into Allison's face.

"Let me know what you think. Be honest. You'll never get what you like if you aren't." Jack adopted what he hoped was a knowing look as she thanked him for the drink and took a deep draught.

"I like it, very refreshing. What's in it?" Allison asked, smiling happily.

"This is just vodka, ginger beer, and lime juice," was his reply.

"I haven't had vodka in years," Allison confessed. "I didn't think I could stomach the stuff anymore. But this is delightful," she said.

"To trying new things!" exclaimed Jack, holding his own copper mug out in a toast.

They clinked glasses and before drinking again. "Now," demanded Allison, "what is so unusual about this neighborhood? I have a strong suspicion that it's got something to do with your dirty sheets."

Jack held up his hands in surrender. "You're absolutely right. It turns out that some in this neighborhood are a bit more open with their bedrooms than I had ever been."

Allison looked startled at his revelation, her mug poised halfway to her mouth. "Swingers?"

"Something like that," was Jack's vague reply.

"What the hell is that supposed to mean?" Allison demanded. "You can't just leave it there."

Jack smiled at her animated reaction, though he felt color suffusing his face again. "It's more along the lines of I have sex with the wife, no strings attached," he confessed. "The husband gets off on seeing his wife with another man," he finished. "Me," he added with an afterthought. Jack thought it premature to describe all of his recent licentious to the pretty red head, so he held back a bit.

Allison looked at him appraisingly for a moment as Jack took a big gulp of his drink, the ice cubes rattling in the metal cup.

"Bullshit," she stated flatly.

"No, it's true," he countered. "Odd as it may sound."

"So is the woman in question a hot wife or is the husband a cuckold?" she asked, color suffusing her pale cheeks.

Jack was surprised she knew those terms: "Cuckold," he clarified for her.

"No fucking way," she said in a low voice.

"I could prove it to you if you'd like," was Jack's response.

Allison mulled the offer over as she finished her drink, setting her cup on the bar before pushing it to him. "OK, prove it. But I'm going to need another drink."

Jack grinned at her and grabbed his phone to text Debbie but paused. "Care to turn this into a wager?" he asked. "If I'm not lying, you give me a kiss?" He waggled his eyebrows at her.

She laughed melodiously. "Fine. If you can prove everything you just said, then I'll kiss you. What do I get if I win?"

"Anything you want," was his immediate reply.

She flushed, but had no response, and Jack let the matter slide as he texted Debbie before mixing them new drinks.

The pair didn't have to wait long: the doorbell chimed within minutes and Jack excused himself to answer it. Debbie was on his doorstep in a strappy pink sundress, her eyes downcast. Jack reached out, pulling her inside by the hand, and the two walked through the house to the bar.

Jack released Debbie's hand before they stepped outside, and the pair walked towards a stunned-looking Allison.

"No way!" she exclaimed from her barstool, "No fucking way!"

Jack grinned at Allison and stopped next to her stool, Debbie facing the pair. "Yes fucking way. Every fucking way in fact," he said with a mischievous grin. "Suck it," he said, turning to Debbie.

Debbie, who uncharacteristically had not said a word, sank to her knees in front of Jack and began unzipping his fly, fishing his thick half-hard cock from inside his khaki shorts. No one spoke for several moments as Jack and Allison watched Debbie's lips stretch around his shaft and begin bobbing her head.

"I'll take my kiss now," Jack said in a soft, low voice.

Allison started and looked at him, shaken back to reality. She paused before standing and moving next to him.

"A bet is a bet I suppose," she said, somewhat hoarsely before molding herself into his side, her soft lips finding Jack's own. As her friend serviced Jack, Allison's hands moved from his face to his shoulders before sliding across his chest. His hands traveled similar paths across her body, but instead of moving to her chest they slid to the short tennis skirt.

Allison broke their kiss and grinned at him. "That wasn't part of the bet mister" she said playfully, though she didn't remove his hands as they groped her muscular ass, and he pulled her skirt up so he could palm her soft cheeks.

"She'll do you too if I tell her to," Jack murmured in Allison's ear. "In fact, she'll do anything I tell her to, won't you my little slut?"

Both Allison and Jack looked down at Debbie who had remained looking at Jack while she serviced him. Debbie moaned with her mouth full of cock.

"It's OK, take a break. Tell your friend all about us." Jack requested.

Debbie slowed and placed a final kiss on the top of Jack's hard erection before standing and wiping her mouth. "It's true. Bill has had a strong cuckold fantasy for the entire time we've been together but we've never acted on it until Jack moved in. Bill isn't well endowed, and has always wanted to see me with a bigger man, to be dominated by both of us. For my part, I've always been a submissive in the bedroom, but Bill can't dominate me the way I need. Jack can fill both roles well. Bill and I have never been happier or had better sex since involving Jack and Cindy and Max."

Allison's eyes, which were already wide, almost popped out of her head when Debbie named the other couple. Jack still had a hand on her exposed ass, massaging it slowly as Debbie confessed to her friend. "Do you mean that you're fucking Cindy too?" she asked Jack incredulously.

"Guilty," Jack admitted. "See why I needed to wash my sheets?"

Allison laughed breathlessly. "Holy shit. I never would have guessed. Personally, I've always been curious about group sex but Tony only wanted to bring other women in. I've never been with a woman, though I'm not completely opposed to the idea. It's just that I didn't think Tony was doing it for the right reasons. He just wanted to fuck other women, not to deepen any connection that we had."

"It has been a hell of a week," Jack admitted. "Ever seen Debbie's tits?" he asked Allison. "They're fantastic. Show her," he demanded, looking at Debbie.

Debbie flushed, but obediently shrugged her shoulders out of her top, her dress falling to her hips and exposing her large breasts. Her broad areolas crinkled under their gaze, hardening and darkening as Jack reached a hand forward and groped her playfully.

"Good girl," he murmured before turning to kiss Allison again. Allison responded with vigor and Jack's hand moved up her side to feel the swell of her breast over her top while his other hand continued to toy with Debbie's. Allison's hand reached down for his cock, gripping it tightly as her hips began to undulate, grinding on Jack's thigh as their kiss deepened before he broke contact.

"Want Debbie to make you cum? Cindy really likes her tongue." Jack sensed that this was a critical moment, and he saw Allison wrestle with the idea.

"OK, let's do this," she breathed.

"Lose the dress Debbie and then grab the sheets from the dryer. Meet us in the bedroom," Jack commanded.

Debbie slipped the dress down her hips where it pooled around her feet. Jack was pleased that she wasn't wearing any underwear and he could tell how aroused she was by the gleam on nether lips as she stepped out of the garment.

Debbie turned and began walking into the house. Jack again offered Allison his arm after tucking himself back in, and the trio made their way inside.

Debbie arrived in the bedroom moments after Jack and Allison. "Put the sheets on Debbie. I've already got your husband doing the yard in exchange for my services, I may as well have you helping out inside."

Jack's words drew a sharp look from Allison, and he winked at her as Debbie began fitting the sheet over the mattress. He leaned over and smacked Debbie's upturned ass hard, causing Allison to gasp.

"She likes it," Jack said to Allison. "Don't you Debbie?"

"Yes," came Debbie's soft reply. "I really get off on a little pain and humiliation. Bill's never been able to give me either."

Debbie finished with the sheets and returned to stand in front of the couple.

"Good job. Now strip Allison for us. I want you to get her ready to fuck me for the first time," Jack growled.

Both women flushed slightly at his words, but neither objected. "You should touch her if you want to," Jack said to Allison, indicating Debbie's nude form. "Do what you want to with her. She's got a great body and the two of us are going to make you cum like you've never imagined. Today can be anything and everything you want: it's all about you."

Debbie was undoing the buttons on Allison's blouse as Jack spoke, her hands fumbling slightly with the small discs. Allison's eyes flicked from Jack's own to Debbie's body, evidently tempted. Jack grasped her hand and moved it to Debbie's breast before releasing it.

He watched Allison's fingers begin to knead the tanned flesh of her friend's breast, before releasing it to pinch Debbie's hard nipple. Debbie moaned in response, her knees buckling slightly as she rubbed her thighs together.

Allison was forced to let go as Debbie pushed her blouse over her shoulders and down her arms. Her bra was flimsy, barely containing her breasts, and Debbie reached behind Allison's back, releasing the clasp. As the cups fell away Jack forgot to breathe. Her breasts were about as large as Debbie's but with creamy white skin that almost hid the vasculature underneath. Her areolas were as large as Debbie's, but a very light pink, almost nonexistent, capped by thick pink nipples. Raspberries, Jack thought approvingly.

Allison let out a shuddering breath, looking out at the others through half-lidded eyes. Jack could tell she was experiencing a jumble of emotions and sensations.

"Relax," he murmured in her ear as Debbie's hands slipped down her sides, brushing the swell of her breasts on their way to her skirt. Debbie sank to her knees as she unclasped the skirt, sliding it down Allison's pale, muscular legs. Allison's thong was the next to go, a skimpy number that didn't hide the broad triangle of trimmed red hair at the nexus of her legs. Jack felt himself harden at the sight of her sex. Her inner lips were enormous, dangling from her meaty outer mound.

Jack couldn't help himself, stepping close Allison and kissing her deeply, his hands feeling the smooth flesh of her body for the first time. Allison moaned as his right hand traveled from her breast and across her flat stomach towards her sex.

He pulled away from her hungry lips and offered his fingers to Debbie who had stood, her task complete. "Wet them for me," he directed, and Debbie sucked his fingers into her mouth, her tongue dancing between the digits.

Satisfied, Jack dropped his hand between Allison's legs as she shifted, allowing him better access. He toyed with her outer lips before palming her mound and sliding his moistened fingers between her surprisingly wet folds. He removed his hand, tasting her arousal on his fingers while he looked into her eyes.

"Delicious," he proclaimed. "Now get comfortable on the bed and let Debbie get to work on you. Debbie, if she's not begging for my cock within five minutes you'll be punished."

Jack grabbed Debbie as Allison unfolded herself onto the bed, kissing the brunette deeply as his fingers dug into the ample mound between her thighs. His fingers were quickly coated with her juices and she began to buck back against his hand.

"Eat me Debbie," Allison called from the bed. "Make me cum. Make me ready to take his fat cock." Jack felt himself harden even more with her words, and as Debbie sunk to her knees on the side of the bed Jack began to strip his clothes.

He watched as Allison reached forward, grabbing the back of Debbie's head and pulling her between her legs. Allison wrapped her fingers in Debbie's hair and began grinding her hips on the brunette's face.

"That's it, suck my clit you fucking slut. Bite it, kiss it, stick your tongue in my pussy. Get it in there deep. Ahh, yessss." Allison's free hand caressed her own pale breast, pinching the nipple, twisting it as she forced Debbie's face harder into her wet folds.

Jack climbed on the bed, passing Debbie and finally pausing next to Allison's face. Her red hair was splayed on the white sheets, her eyes closed in concentration. He gently touched her chin, pulling her face towards him before he bent and kissed her tenderly, their tongues touching lightly. He rose, positioning his hips next to her face, pushing his stiff cock down at her mouth.

She moaned as he traced the head of his cocks between her lips and across her teeth. He palmed her unused tit with his free hand, the big nipple obvious against his palm. He pushed harder against her mouth with his dick and her lips opened, allowing him to feed his meat into her hot, wet mouth. Her cheek bulged obscenely at first, but she tilted her head towards him to give him better access to her throat.

Allison's moans were unbroken now, only varying in their intensity. Jack reveled in the vibrations traveling through his shaft from her lips, and he felt her teeth lightly scrape him as she began to cum under Debbie's talented tongue. She bucked her hips violently, the words of her screams distorted by the hard cock that filled her mouth.

Jack removed his glistening cock once she finished. "Fuck me!" Allison gasped. "She is good."

Debbie rocked back on her heels, smiling proudly. Jack moved to her, kissing her, tasting Allison's release on her lips and tongue. "She's definitely a keeper," Debbie said with a grin when they broke.

"Agreed," said Jack. "Now we've just got to convince her of that."

"Not sure you'll have to do much more," Allison replied, "but I'm up for whatever you've got next."

"Fantastic," Jack replied. "Debbie, put my cock into your friend. Watch as I give her the fucking that could have been yours."

Both women moaned quietly, and Jack stepped forward, positioning himself between Allison's splayed thighs. Debbie moved onto the bed next to the couple, her slim fingers wrapping around Jack's hard member and tracing it through her friend's folds, seeking her opening.