New Jack Ch. 08

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 feel free to leave a comment or send me a message.

8.

After breakfast Jack spent his morning cleaning his sheets and swimming. The exertion made his muscles burn deliciously as he stroked his way up and down the pool.

Sheets now clean and freshly showered, Jack decided to head out and explore Naples a bit. He parked near the pier and ambled around, poking his head into antique shops, bookstores and other similar establishments.

He selected a small bistro next to a promising book store for lunch whose cuisine was only outdone by the scenery, namely a statuesque red head. Her straight locks were pulled back from her pale neck in a simple pony tail, a light blue sundress cloaking but not quite hiding her curves. Jack surreptitiously checked for a wedding ring but was delighted to find her pale finger unadorned.

Finally, he thought to himself, I knew there had to be some unattached women here! Though to be fair, he mused, the ones who were attached seemed to be trying to modernize the concept.

He gave his order to Chris, his server, who was clearly new in his position. Chris moved away, but instead of going to the kitchen spoke to the red headed woman instead. The two conversed for a moment, the woman apparently giving her order before Chris retreated into the back of the restaurant.

The comely woman reached into a shopping bag and removed a handsome, leather bound book. Jack couldn't make out the tiny words inscribed in gold-embossed letters yet he was intrigued nevertheless. Good looking, single, and likes nice books?

Jack's thoughts strayed from his surroundings as he mentally contrasted his current situation with his agenda for the afternoon. He wasn't eager to give up his newfound power and freedom over his neighbors but a woman like this would make him seriously consider it.

Chris interrupted Jack's musings with precisely the wrong plate of food. Jack started to say something, but Chris was already disappearing into the bowels of the restaurant. Jack looked around and saw a similar expression of frustration on the pretty woman's face. He glanced at the dish in front of her and saw his order: Chris had obviously mixed up the tickets.

Seeing his opening, Jack stood and grabbed the woman's food from his table. He approached and saw her look him over, her light blue eyes coming to rest on the plate of food in his hands.

"I'll have what you're having," he joked lamely.

A smile spread across her face slowly and she shook her head. "Thanks. I was just wondering if this day could get any worse. I'm starving."

"Well we can't have you going hungry," Jack replied easily, swapping the plates. His eyes rested on the book on the table.

"Oscar Wilde, eh? He's one of my favorites. Who knew some of those people were so funny?" His smile instinctively spread across his face as he made out the title; The Importance of Being Earnest.

"Right?!" she said, her features suddenly animated. "A friend told me about a prospective client who wants a library, so I thought I'd check around and get a feel for that type of place. I'm an interior decorator," she added by way of explanation. "I was downtown on other business," her face darkened briefly with these words, "and decided to poke around. I know that I had heard his name before but never really read anything of his. I picked it up and wasn't able to put it down!"

The smile had returned to her face, her eyes ablaze with her newfound passion. Jack thought she looked radiant in the bright afternoon light that bathed the terrace.

"Similar thing happened to me. Would you like some company now that we've got our food sorted out?" Jack asked.

She glanced at him, momentarily unsure. She seemed to struggle with his request internally, and just as he was about to excuse himself and return to his seat she came to a decision, her face clearing. "Sure. Why not?" she said rhetorically.

"I'm Jack" he said as he sat across from her. "I'm new in town, just moved in a few days ago."

"Allison," was her reply. "I've been down here for, god, 10 years now." Her voice was sober again, and Jack thought it best to re-direct the conversation.

He did so successfully, fixing again on Wilde's works first and their conversation flowed easily from there. He reiterated his love of books, the classics especially, and talked about his current challenge of outfitting his new house.

"Maybe you'd like to take a look at the place sometime?" he suggested in what he hoped was a casual voice. "A neighbor friend referred me to someone, but I haven't actually signed on with a decorator yet."

She eyed him again, with a little less suspicion this time though. "Actually, I could use the extra work now. My schedule has recently become much more flexible, and frankly I could use the distraction."

They exchanged cards, Allison promising to touch base with Jack early next week once things had settled down. Chris had popped up halfway through their meal and had been properly mortified, and the manager had waited on them for the rest of their meal.

They paid their respective bills and walked out of the restaurant, Jack heading towards the pier and his car, Allison taking her leave and sliding behind the wheel of a white Lotus convertible. He watched her speed off, the wind playing with her hair as she seamlessly merged into traffic.

Jack shook his head, as he sat down in his hot car. She was a hell of a woman. He hoped Debbie hadn't promised her decorator friend anything.

He stopped by the liquor store on the way home to re-stock his supplies. He wasn't sure what the group would be in the mood for, so he got some of everything, including a few cigars.

He was unloading his car when Bill walked over. "So, what'd you have in mind for me?" Bill's voice trembled slightly, and his eyes wouldn't meet Jack's own.

"The yard," Jack said, chuckling to himself at Bill's obvious discomfort. "No playing until the women arrive. But Debbie wants me to rub off on you, so here it is. You'll be taking care of my yard until further notice. Our selections from the other day are in the garage, so go for it."

Bill's relief was visible, and he hurriedly moved off to get started. Jack put away his purchases and opted to go ahead and get into his swimsuit before going out to check on Bill's progress.

Bill had made adequate progress: Jack's law was mowed and edged, the beds weeded. A flash of motion caught his eye and he saw a white Lotus pull into the house across from Bill's. Allison slid from the driver's seat, unfolding her lovely frame and glancing towards Bill and him.

She extended an arm, lifting it in greeting, which Bill returned. The men silently watched her approach until she was within earshot when Bill called "Allison, you should meet our new neighbor. This is Jack, he just moved in Sunday."

"Small world," she said looking at Jack. She went on to explain to Bill that the two had wound up sharing lunch earlier.

"Where's Tony?" asked Bill. "Back at the office after your trip already?"

"Well, I suppose it will come out eventually. Tony and I are divorcing: in fact, I had just finished filing the paperwork downtown when I met our new neighbor here," she said with a nod to Jack. "Apparently he's 'in love' with his secretary and has been for some time." Her fingers made air quotations as she said this. "God, he sickens me. But if that's what he wants, then who am I to stand in his way?" she questioned the pair rhetorically.

Bill murmured his condolences for her plight, and Jack added his own.

"Why are you mowing his yard Bill?" A look of mild confusion crossed her pretty face as she abruptly changed topic.

Bill began to color, and Jack quickly stepped in. "Bill owes me a few favors. We won't bore you with the details, but he'll be taking care of my yard for a while."

Bill looked gratefully at Jack, and Allison seemed satisfied. "Well, I won't keep you from it," she said to Bill. "Nice to see you again Jack. We'll have to get together soon to talk about your plans. Tomorrow, late afternoon?"

Jack agreed, and the two men watched Allison depart. "Her husband always was a dick," Bill said in an undertone so that the statuesque red head couldn't hear him. "Big, macho, weight lifter type. Thought he was god's gift to women. Debbie said that Allison told her that Tony always insisted on making love in front of a mirror so that he could watch himself. She told Debbie that he was lousy in bed and wouldn't even go down on her."

Jack grunted. "What the fuck is wrong with that guy?"

Bill finished putting away the lawn equipment and hurried home to get ready. The two couples were due over in half an hour, so Jack busied himself prepping drinks and laying out paper plates and plastic utensils, opting for a quick cleanup instead of a night of dishes.

He was glad that Cindy and Max arrived first. Cindy's bubbly personality was in overdrive and she embraced him warmly, her tits pillowing against his chest. Max looked like a changed man. His clothes seemed to fit him better and his expression was open and happy as he shook Jack's hand.

"I can't tell you how excited I am!" he gushed. "I've wanted this for so long, but Cindy has always been reluctant to act on it. I'm not sure how you did it, but I'm so glad you did! And Bill and Debbie too! It's basically going to be an orgy!"

Jack had wanted to talk to Max precisely for this reason. "Max, calm down and listen to me. Yes, we will be participating in group sex tonight. But the reason Cindy chose me is that I am in charge. Completely. That means you will only play as I allow. You will only cum when I permit it. I am going to fulfill your fantasies for you, but I will also push your boundaries. I think you must have some idea what I have in mind if that bag contains what I think it does." Jack indicated at the bag from an adult store in Max's hand.

"Do you agree to my terms?" Jack queried.

"Yes," Max said breathlessly.

"This means that use and abuse your wife in any way I see fit. She will remain your wife: this is purely sexual. She will go home with you, most nights. You will touch any other cocks that I tell you to, you will suck cocks if and when I tell you to. You will eat cum, sometimes off of a woman, sometimes sucking it out of a cock. I am going to push your boundaries, and push hard. Do you understand?" Jack's voice was driven by his newfound heady sense of control and brooked no argument.

Max seemed to shrink under Jack's diatribe but replied "I understand, I agree."

"Good," said Jack, his tone now amicable. "Now, I believe that you also have some chemical assistance for me? Something that will ensure I fuck your pretty wife senseless tonight?"

Max's face flushed with embarrassment or arousal, Jack couldn't tell which, and he nodded, digging a small plastic container containing a few blue pills from his pocket.

"Perfect," Jack said, accepting the offering. "Now go fix your wife and me some margaritas: I need something to wash this down. There's a pitcher of them cooling in the fridge at the bar out back."

Max scurried away, his portly frame jiggling as he went. Jack directed his attention to Cindy who had removed her cover up to reveal a blue-gray bikini that again highlighted her blue eyes.

"You look fantastic," he said to her, truly meaning it. Her curves challenged the structural integrity of the thin pieces of fabric, her cleavage overflowing the small top that Jack knew must barely conceal her large light pink areolas.

She stood still, proudly displaying her body as his gaze wandered over her curves. Jack felt blood surge to his cock as he thought about what he wanted, and would, do to her fantastic body tonight. He stepped to her, and his right hand cupped her mound over her bathing suit briefly before his fingers slid the fabric to the side. His left hand went to her right breast, peeling away the small triangle and he palmed her heavy globe, her nipple hardening against his palm.

He had just dipped his fingers into her sex, tracing them through her slippery folds when Max returned with the drinks. Jack slid his fingers around Cindy's clit, eliciting a small moan from the latter as she bucked her hips against his hand. Max just stared at the embracing couple, fixed to the spot.

"God, she's so wet already. Did you know that Max?" Jack asked, looking the shorter man in the eyes as Jack's hands continued to explore his wife. "Did she tell you that I wouldn't let her finish this morning? That I left her hanging? I could have made her cum all over my cock: she's done that many times in the past few days."

Max was transfixed, unmoving, unresponsive to Jack's teasing. "Here," Jack said, releasing Cindy and stepping towards Max, "taste her if you don't believe me." With those words he pushed his wet fingers into Max's mouth.

This wasn't on Jack's list of fantasies, but he surmised Max would love it and figured he should indulge the guy. After all, Jack had used every hole his wife possessed and intended to continue doing so for the foreseeable future.

Max moaned around his fingers as he tasted his wife's arousal on the other man's hand. Cindy watched the display with an amused look on her face.

The doorbell rang, indicating the arrival of the other guests, pulling Max and Cindy back to their surroundings. Cindy fixed her suit, and Max set the drinks down. Jack grabbed one and downed a pill, washing it down with the pungent concoction before opening the door.

Debbie bounded in wearing her tiny white bikini. She flung her arms around him and kissed Jack deeply as Bill closed the door. "Howdy neighbor," she said with a twinkle in her eye, a mischievous grin plastered to her face. "Did you start without us?"

"Not really," said Jack, smiling at her, his hand reaching down to palm her supple ass cheek. Jack extended his other hand to Bill, who took it and shook. "Nice job again on the lawn. I'm sure it will go quicker next time."

"Uh, thanks," Bill said in a small voice, nervously glancing at Max.

Debbie ground her pelvis against Jack's leg, pushing him backward and onto a circular bar stool as she kissed him again. "Hey, I didn't get a kiss yet!" Cindy exclaimed, and she straddled his other knee, pulling his face from Debbie's.

As Cindy's lips locked onto his own, Jack glanced first at Max, and then at Bill. His hand that wasn't kneading Debbie's ass drifted down onto Cindy's and mirrored its partner's movements. Cindy moaned into his mouth as he pulled the material into the crevice of her cheeks.

"Hey! Share!" Debbie joked, and pulled Jack back to her. As she kissed him he pulled her bikini bottoms tight as he had with Cindy, exposing her luscious ass to the two husbands. Like Cindy, Debbie moaned into his mouth with her exposure and Jack opened his eyes to glance at the two husbands. They stood rooted to the spot, Bill's suit sporting a small tent while Max's betrayed no sign of arousal.

Jack broke the kiss, turning his head slightly so he could see around Debbie. "Bill, please hand me my drink. I'm going to see if your wife is as turned on as Max's is."

Bill colored slightly but complied with Jack's request. Jack eased the two women off him and had Debbie stand on the opposite side of the bar facing the men, her arms supporting her torso on the counter, her legs spread slightly. Jack sipped his drink and nonchalantly slipped his fingers between the fabric of Debbie's suit and her full mound. He teased her puffy lips for a moment before dipping his fingers into her soaking vagina, coating his fingertips thoroughly with her juices.

"Hmm, she's definitely wet, but I'm not sure who is wetter. Cindy, come here and let me compare." Jack's words drove the husbands to begin shifting from foot to foot with anticipation as Cindy assumed her position next to Debbie. His free hand slipped into Cindy's bottoms, and he teased her lips just as he was teasing Debbie's.

"Too close to call," Jack proclaimed. "It's a tie for now."

The women's reactions were immediate and overlapping. "What?" "Are you serious?" "She's been here longer!" "You touched her more!"

Jack held up his hands to quell the uproar. "Why don't we see which man is most aroused? That should be objective enough. You two can be the judges."

The women grinned, first at him, then at each other.

"OK boys," Cindy called with a giggle. "Let's see where everyone is at. Lose it all: we want to see those little peckers."

The husbands traded dubious looks but began to strip, removing their shirts before kicking off their footwear and shucking their swim trunks.

The women whooped with delight as their husbands' endowments were displayed for the group. Both men covered themselves with their hands, changing the women's gleeful shrieks to protestations. "You can't do that!" and "Drop your hands!" echoed across the bar at the men.

Jack placed a hand on both women's shoulders, quietening them. "Bill and Max, I have rules here. If I ask you to do something, you do it or there are consequences. Similarly, if the women ask something of you, you'll do it if I agree. Since you disobeyed, I'm going to punish you and I'm going to do it by spanking your wives in front of both of you."

His words were met with silence, but the men slowly removed their hands. He felt the women's shoulders tense under his touch with his final words, and slowly began to trace lines down their backs until his hands were caressing the soft flesh of their asses.

Bill's short thin penis was fully at attention, the small head glistening with what Jack figured was precum. Jack guessed that Max was hard, but it was hard to tell. His penis was little more than a small head atop a shaft of about half of an inch though it was a bit thicker than Bill's.

The women giggled unabashedly as the color rose in both men's faces. "They're not even as big as you if you put them together," Debbie squealed, looking back at Jack. Her comment drew a fit of giggles from her buxom blonde friend.

"That's better," Jack told the men. "Though it doesn't make up for your initial hesitation." His hands slide the bottom of Debbie's suit off where it pooled on the floor before repeating the process with Cindy. The men couldn't see anything lower than the women's belly buttons across the bar, so Jack stooped and placed both garments on the bar to clarify the women's state of undress.

His hands caressed their bare flesh as he spoke to the women now. "Look at your husband while I spank you for their transgressions. Remember that this is happening because of they are ashamed of their tiny, inadequate peckers. Use this memory later to dominate them as they both need."

Jack positioned himself at Cindy's left side, palming her bikini-clad breast in his left hand as his right rose and quickly fell. Cindy yelped as she absorbed the blow and Max swallowed hard. His right hand repeated the action on her other cheek and then began caressing the same flesh.

"Max, did you know that Cindy positively gushes when I spank her? No?" Jack answered his own question as Max wrested his gaze from Cindy's to meet Jack's own.

Jack's hand rose and fell again twice in quick succession and the blonde squirmed underneath his touch. His left hand kneaded the flesh of her breast roughly and Cindy had begun to moan lasciviously. He stopped the caress of his spanking hand and dipped it into her sex, easily sinking two fingers between her small lips.

Jack's face broke into a smile. "Absolutely soaked. I wonder if she can cum from being spanked. I bet I find out before you do Max." His taunting had the intended effect and Max colored to his deepest hue of red yet.