New Jack Ch. 13

Apologies for the long wait. This is (probably) the second-to-last installment in this series.

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.

*****

13.

Jack's week started with a bang: a two-night trip over to Miami that he had been looking forward to prior to getting to know his neighbors so well. He had extracted promises for naughty pictures from Debbie and Cindy prior to their departure the night before while their husbands watched on and had made dinner plans with Allison for Thursday night.

His meetings were productive, the meals sumptuous with fantastic views of the Atlantic over white sand beaches. He quickly learned to adjust his phone settings, preventing the pictures the horny wives were sending him from popping up on his locked screen. His evenings were spent having long corporate-led dinners, both ending after ten o'clock.

He responded to Cindy and Debbie's group text request wherein they demanded to know what night each of them got this week. Jack figured he should stay out of it and told them to figure it out but let them know that Thursday night was off-limits because of his dinner with Allison. Cindy had eventually won out, claiming Wednesday night.

He arrived home Wednesday in the early afternoon, opting to finish his remaining conference calls from the comfort of his own home rather than continuing into his office in downtown Naples. He had had enough with introductory calls and was dying for sexual release. He hadn't managed to find the time to rub one out while he was gone, only barely managing to shoehorn quick morning workouts into his busy schedule.

He was just finishing his last call of the day when his doorbell chimed. Wondering who it was, but having his suspicions, he begged off the call and opened the door. Debbie stepped across the threshold, molding her body into his before he had even had the chance to close the door.

By the time he had managed to push the door closed Debbie was on her knees, fishing his soft cock from his now-unbuckled slacks. She pulled them to the floor as her mouth engulfed his entire length, her tongue doing marvelous things to his burgeoning shaft.

"Hello neighbor, I guess you missed me?" Jack quipped as Debbie stared up at him with her brilliant green eyes.

"You could say that," Debbie replied, her mouth popping off his cock as she repositioned herself to lick his balls while her hand continued to stroke his shaft next to her cheek.

Jack reached down and pulled the string of her sundress that held her breasts in check. Freed, they bounded forth, resplendent in their bronzed glory. Her nipples were hard, thicker than erasers and had shrunk to the size of old silver dollars, delightfully crinkled with her arousal.

Debbie's hand that wasn't on his cock was busy beneath the sundress, dabbling her clit rapidly.

"I thought it was Cindy's turn today?" Jack questioned.

"It is," gasped Debbie, coming up for air. "But I just couldn't wait. Besides, our exact agreement was that she could have you tonight, and it's just now three."

"You naughty little minx," Jack joked. "What do you think Cindy would say? Or Bill for that matter?"

"Bill would just be jealous that he doesn't get to play," she responded between kisses and licks to his cock. "Cindy, well, she should have been more attentive to our agreement."

Jack was silent for a moment as she attempted to swallow his cock again, though he was hard now and she couldn't quite get it all of the way into her mouth, try as she might. It was just too wide for her jaw to accommodate, though he loved the way her lips stretched around his shaft while she gazed up at him.

He reached down and pulled her to her feet, leading her into the bedroom. "Lose the dress," he directed, and watched as the flimsy garment pooled to the floor around her now-naked body.

God, her body is phenomenal, Jack thought to himself before repeating the thought out loud for Debbie's benefit. She blushed slightly and pirouetted before grabbing her tits and sliding her hands down her curves and over her hips.

He stripped the rest of his clothes as Bill's wife exposed herself to him, bending over at the waist, pulling her large lips apart with her fingers and then making a show of cleaning them off with her mouth.

"I love it when you're bad," Jack said softly, causing Debbie to pause her display. "It gives me the justification to do what I'd like to do anyway."

He stepped into her, his hands sliding across her breasts and then down her sides to the swell of her hips. He reached around, palming her tanned globes before sinking his fingers deep into her flesh while pulling her cheeks apart. He bit her lightly on the neck and she sighed, enjoying the feel of his hands and mouth on her while his hard cock pressed insistently into her stomach.

"Now bend over and assume my favorite position" Jack said, releasing her. Trepidation flitted behind Debbie's eyes as she acquiesced, placing her hands on the footboard of the bed, her legs spread a little more than shoulder width apart. "You deceived Cindy," he murmured, his hand rising and falling for the first time with a crack against her ass. "That wasn't nice," he continued as his hand fell against her other cheek.

Debbie grunted with each blow but held her position. His hand rained blows against her upturned cheeks, her grunts becoming moans and finally yelps. Her skin was hot to the touch now and Jack traced his fingers lightly across her reddened flesh.

"I'd say that I hate to do that, but I'd be lying," Jack said with an evil grin. "I really do appreciate you stepping out of line to give me the reason though."

"You don't need a reason," Debbie panted back. "Anything you want, anytime, anywhere."

Jack slipped his hand lower, allowing his fingers to play with her meaty lips. He dipped his head and licked her from her clit to her asshole, her juices bathing his tongue. "God, you taste divine," he murmured before licking her again and again. Debbie's hips bucked underneath his tongue, urging him on before Jack acquiesced to her unspoken request and trapped her clit in his mouth, harrying the little nub with his tongue.

Debbie began to shake and so Jack stopped, leaving her right on the edge of orgasm as a groan of frustration escaped her pretty lips. "Fuck yourself on my cock if you want to cum," he commanded, stepping behind her and forcing his throbbing erection into her wet cunt.

She immediately went rigid with the intrusion and Jack wondered if that simple motion had finished her before she began bucking her hips back against him, grinding on his hips while his cock remained fully seated inside of her.

"Oh God!" she shrieked as he felt her fingers graze his balls as she attempted to flick her clit. "Fuck, I'm cumming!"

Jack remained motionless, letting her ride out her orgasm but withdrew when she stopped moving. "Now suck it," he instructed. "Suck it until I cum."

Debbie immediately spun and dropped to her knees as Jack grabbed his phone from his pants. He remained where he was and let her shuffle across the floor to him on her knees. His fingers toyed with the phone's buttons while Debbie licked her cum off his cock with relish. She finally put her mouth over the top of his cock and worked it into his throat, simultaneously pumping him with her hand.

Jack's finger hit one final button on his phone as Debbie looked up at him with her mouth full of his cock. "Hi Bill!" Jack said. "How's it going?"

Bill's face looked back at him uncertainly over FaceTime. "Uh, good I guess. What's up?"

"Funny you should ask. Currently my cock is up, but your wife is down on her knees. She just couldn't stay away. Want to see?"

Debbie groaned as Jack flipped the phone around to let Bill see his pretty wife with a face full of cock.

"That's it, suck it my little cum whore. Bill," Jack said flipping the phone around to see Bill's now-red face staring back at him, "did you know that Debbie's night is Friday night? But she worded everything with Cindy so that Cindy didn't officially 'have' me until tonight. I'm sorry to say that I had to punish her. See?"

Jack leaned over Debbie so that Bill could see her still-red ass, forcing his cock farther into her throat and causing her to gag slightly. "She apparently loves it, getting spanked that is. I think we both know how she feels about having my cock splitting her lips. Did you know that Bill?" Jack taunted.

Jack turned the phone around so that he could see Bill. "N-, N-, No, I didn't know that," Bill stammered. "She's never let me spank her before."

"Ah, then I've got to catch her up! Good to know. She really does have the prettiest eyes Bill. I love how she looks right into me while my cock slides between her pretty lips. Did you look into those eyes and dream of this on your wedding day Bill? Here, let me show you." Jack's eyes had been off camera, looking into Debbie's as he taunted her husband. "I do like it when she uses her left hand to pump my shaft: the wedding ring really adds something. Did you pick it out yourself Bill?"

Jack heard Bill's voice: "Fuck," come from the phone as he watched Debbie fellating Jack.

"I'm about to cum Bill. I'm going to cum all over her pretty face and send her back across the street without cleaning up like the slut she is. Are you ready?"

Jack's question was met with a groan from both the phone and the woman at his feet. His balls churned as he grabbed his dick from Debbie and pumped himself rapidly, aiming at her face.

"Are you ready Bill?" Jack demanded just as he was about to erupt.

"Yes," Bill gasped through the connection as Jack unleashed his load on the man's wife. Jack roared as his cock absolutely erupted, releasing several days-worth of his pent-up seed. His cum splashed off Debbie's cheeks and forehead, lodged itself in her hair and dripped into her open mouth.

He continued to pump himself until nothing else came out and then fed his cock back into Debbie's still-open mouth.

"God, I needed that," Jack confessed to Bill. "See you later buddy," and he hung up the phone.

Debbie's tongue was massaging his deflating cock, her face still covered in his cum. He snapped a quick picture with his phone and sent it to Bill.

Debbie dressed, and Jack kept his promise to Bill, sending her back down the street with his cum drying on her face and in her hair. He opted to go for a swim before dinner and was just about to rinse off in the outside shower when his doorbell sounded.

He quickly dried himself and stepped inside to answer the door. Cindy greeted him in a light white dress that was translucent in the early evening light. She had apparently walked over but smelled fresh as she pushed the door closed behind herself, dropping a small duffel, and wrapped Jack in a tight embrace.

"Two fucking days and I'm losing my mind," she murmured into his neck as his hands found their way under the hem of her dress and gripped her meaty ass tightly. "My sex drive has never been higher and while Max is getting better about pleasing me, it just isn't the same."

Her lips grazed his ear and he felt a pleasurable tingle shoot through his groin. "Max has begged me to peg him the past two nights. He's absolutely over the moon about everything that happened on Saturday," she continued, pressing her chest against his, "I am too."

"I'll admit that I thoroughly enjoyed myself too," Jack replied as his hands began to slide up and over her hips to her waist. "What was your favorite part?"

"Hmm," Cindy temporized as her hands found his hardening cock, rubbing it over his bathing suit. "I'd have to say when you and Allison made me cum by spanking me with your cock in my mouth and her fingers in my pussy. God, that was so hot," she breathed into his neck, kissing him lightly.

Jack stepped back from her slightly and pulled the dress up and over her head. Like Debbie she wore no undergarments, and her large breasts swung free as the dress released them.

"No underwear, eh?" Jack questioned. Cindy's broad, light pink areolas stared at Jack and his hands covered them, massaging them, and he felt her nipples harden against his palms.

"Didn't see the point," Cindy replied throatily, pushing her chest harder against his hands.

Jack's erection was almost complete as her hands continued to grope him, now loosening the strings that tied his suit into place and pushing the damp suit to the floor. She made a move to kneel, but Jack stopped her by squeezing her tits hard.

"All in good time my little slut," he said with a devilish grin. She answered with a sheepish grin of her own as he steered her to the kitchen bar. "Let's have a drink first. Martinis or margaritas?"

Cindy requested a margarita and moved behind Jack as he concocted her requested libation. Her delicate hands snaked around him, pressing her soft breasts into his back as her fingers encircled his hardening cock, pumping it lazily. Her delicate kisses on his back were punctuated with tiny nibbles and Jack felt himself harden in her hands.

He awkwardly turned and offered her the drink which she thanked him for before she took a sip. He faced the bar again, deftly shaking himself a martini as he heard ice crunching behind him in Cindy's mouth.

As he turned to face her again, planning to toast their evening together, he found her sliding to her knees. She lovingly took his cock into her mouth and Jack groaned as the feeling of her ice-cooled tongue contrasted with the warmth of the rest of her mouth. She sucked him languidly, dragging her tongue along the underside of his shaft, swirling it around the crown of his cock as her hand reached for the glass she had placed on the ground.

"How's that?" she asked, releasing him momentarily as she trapped another ice cube with her fingers, popping it into her mouth.

"Fan-fucking-tastic," Jack admitted honestly. "The difference in sensations is mind blowing."

"Good," she said through a mouthful of ice. As she chewed the ice, she fished out another cube, licked the margarita off it, and then traced it around her nipples, hardening them. She leaned forward as she continued to rub the melting ice onto her nipples and sucked him in again, deeply. Her eyes began to water as he felt himself hit the back of her throat, and he reached forward, grabbing the back of her head and forced himself a bit deeper.

"That's a good girl," Jack murmured to her as her cool tongue continued to try to massage the underside of his cock. He released her, allowing her to breathe for a moment. "Pinch your nipples while you suck my cock," he instructed. "Make it hurt a little, just like when I do it."

Cindy obliged, massaging, pinching, and twisting, but she didn't push the envelope, didn't quite get to where Jack wanted her to go.

The doorbell rang, and Jack cursed inwardly at the interruption. If that's Debbie, there will be hell to pay, he thought viciously. With a look of frustration at Cindy he spoke, "Stay just like that. I don't know who that is, but I'll be right back."

Cindy nodded and remained kneeling as Jack strode away nude, grabbing his swimsuit and quickly donning it before answering the door, hiding himself behind it as he opened it.

Allison stood before him, resplendent in a form-fitting black cocktail dress, holding a bottle of wine and a small clutch. The dress completely covered her chest, flaring at her hips with enticing slits along both thighs. Her hair was down, brushing the tops of her lily-white shoulders.

Jack wolf-whistled, and Allison grinned broadly at him, twirling to show that the dress was backless. "I'm glad someone approves and could see me in it," she said.

"Just show me where to put my stamp, ma'am," Jack quipped. "What brings you around? Not that you aren't welcome, but I thought we weren't scheduled for dinner until tomorrow night?"

"We aren't, but I was stood up. I was supposed to have drinks and maybe dinner with one of my suppliers, a cute guy that's been chasing me for years. Guess he had a change of heart though, so when I got home and saw your car in the driveway I figured that maybe you'd be up for a drink."

Allison seemed to run a gamut of emotions as she spoke though she hid them well. Jack thought she was genuinely happy to see him but also trying to deal with the disappointment of her failed date. Unexpectedly, a flicker of jealousy had flashed through him at the thought of her with another man, but it quickly passed. He was, however, happy that fate had led her to his doorstep yet again and ushered her in with a warm smile.

"Well, I'm glad you thought of me," he said. "To be honest though, I'm not alone right now. I told Cindy and Debbie that tomorrow night was off limits, and they worked out a schedule. Cindy is waiting for me in the kitchen."

Allison eyed the prodigious bulge in his shorts. "I can see that I'm interrupting. I can leave if you'd like."

"That's up to you. I'd love for you to stay, at least for one drink so I can memorize how fantastic you look in that dress," Jack said candidly. "Though I can't promise to completely behave myself," he finished with a grin.

"Fair enough," Allison replied. "Shall we?" She extended a hand, which Jack took and led her to the kitchen.

Cindy hadn't moved and remained kneeling, completely nude. Jack released Allison's hand and walked over to her, beckoning her to rise.

"What'll it be?" Jack asked Allison.

"Wine will be fine," she replied casually, offering the bottle she had brought.

"Cindy," Jack said, "open the bottle for Allison and pour her some wine."

Cindy looked around as if for her dress. "No need to cover up on my account," Allison commented casually but firmly, implying a command with her tone.

The curvy blonde flushed slightly at being asked to remain nude and serve her friend and neighbor, but she accepted the charge without comment. Jack pointed her to the wine opener and enjoyed the view as Cindy's pendulous tits swayed with the effort of uncorking the wine.

She poured a generous glass of the pinot noir for Allison and brought it over to where the couple stood, leaned against the bar. Jack grabbed his martini and lifted it in toast to Allison: "To making the most of life when plans go awry," he said, and clinked her glass lightly.

"Amen," Allison replied, and took a deep sip of the ruby liquid. "Now, what were you two up to when I interrupted?" Her eyes flitted from Jack to Cindy, a knowing look etched into her face.

"Would you like us to tell you or show you?" Jack asked casually.

"How about she shows while you tell," countered Allison. "I could use a little entertainment with my wine."

"Deal," Jack agreed, his eyes now moving to Cindy who stood facing the pair. "Cindy was just showing me this marvelous technique she picked up from...where did you say?"

Cindy blushed, grinning. "Cosmo actually. A hundred ways to drive your guy wild or something like that. I've never tried it until just now though."

"Poor Max doesn't know what he's missing. Show Allison the magic you were working on me," Jack said as he passed her the margarita.

Cindy smiled a shy smile as she sank to her knees, popping an ice cube into her mouth and crunching it up. She reached up and tugged Jack's swimsuit down, his thick rod drooping from lack of attention. Cindy opened her mouth and stuck out her tongue and began bathing the sides of his member before sliding her mouth over his helmet.

Jack felt himself sliding into her wet mouth again, the cool of her tongue against the underside of his cock while her warm mouth encircled the rest of him. She began swallowing, the motion massaging his growing cock and Jack felt himself rising rapidly.