tagGroup SexNew Jack Ch. 06

New Jack Ch. 06


Fair warning: this story continues to contain same sex action, rough sex and cuckolding. You'll be better served to start at the beginning of this series than jumping right in here.

I'd love to hear any nice thoughts or constructive criticism you may have and I've been greatly encouraged by those of you who have left messages. Please feel free to send me a quick note or leave a comment!



The trio rinsed off in the large glassed-in shower in the master suite ensuring that all parties were squeaky clean and ready for the day. Debbie had texted Bill to let him know that they would indeed be back over this evening for an after-dinner soak and was confirming with Jack when Cindy piped up.

"Can I gate crash? I don't have anything going on with Max out of town and Debbie crashed my party yesterday anyway."

Jack looked at Debbie, raising his eyebrows to ask Debbie the same question.

Debbie shrugged, "Hell, why not. I've had a lot of fun playing with you and Bill already knows you're over here. It'll be fun to give the little guy a thrill."

"Be very clear with Bill," Jack began, "that he will not get to touch Cindy unless I allow it. Please remind him that my house means my rules and that he's to follow my directions if he wants this to continue."

Debbie agreed and kissed Jack before winking at Cindy and swishing out of the door. Cindy took her leave with a kiss as well, leaving Jack in a suddenly empty house.

It was for the best, he thought. He knew that he needed to take stock of his life given how seemingly every facet of if was in turmoil. Work was fine for the moment, but he would need to be ready to hit the ground running next week. His assistant had emailed requesting that he take a look at his calendar so he could be ready for the slate of meetings and presentations the coming week would hold.

He then thought about the house. He had given Debbie a budget, his preferences, and told her to do as she saw fit. So the decorations would be taken care of. He decided he should order some furniture and so proceeded to dress and leave the house to run some errands while he continued to mull his current situation.

The furniture store was easy enough: soft, squishy leather covered a couple chairs and couches that would be delivered later in the afternoon. Similarly, the big box electronic store promised to deliver the TV's and sound system in a few hours.

With these tasks handled, Jack turned his thoughts to his love life, or more properly the lack thereof. Was he doing the same thing to Max and Bill that the trainer had done to him? Is this why he had agreed and pursued these women? Where the hell had all of this come from?

He had always enjoyed rough sex: spanking, biting, orgasm denial, and some friendly scratching were all part of his normal routine with his ex-wife. She had been the submissive in the relationship just as these women were. He wondered if he was doing this to right a wrong, to get back at the universe for how his marriage had ended. He didn't think so. Everyone involved were consenting adults and walked into this with eyes wide open. Hell, based on Bill's reaction he was doing the man a favor and Debbie certainly appeared to be enjoying herself.

Unable to discover any new revelation or insight, Jack decided to continue to go with the flow. These relationships were allowing him to spread his sexual wings, to try out the fantasies that had lurked in the corners of his mind for years, never expecting to see the light of day. He had seen his fair share of cuckold porn and even read some erotica with the same theme though he never felt there was enough from the bull's perspective. He never identified with the cuckold impulse but had no qualms with those who harbored those sentiments, especially in light of the recent events. He resolved to make sure that all parties in both couples were as sexually satisfied as he was with this arrangement.

On a whim he texted Bill, providing the latter with a short list of things to pick up for this evening's soiree. "Don't let Debbie see them though," Jack cautioned, "it'll be our surprise."

"Lol" Bill replied. "Based on this list I'm sure we'll both be surprised. Can't wait!"

The text was followed with a string of emojis that Jack didn't bother trying to decipher. He had never been very good at reading the nuanced displays on the little faces and Bill's selections were a seemingly eclectic bunch of eggplants, tongues, tacos, and winking faces.

He got the point.

Jack returned home just in time for his lawn care equipment to be delivered fulfilling the store's commitment made on Sunday, followed by the electronics and finally the furniture. He was surprised at how quickly the house seemed to fill.

He made a quick grilled chicken salad for dinner and decided to take a quick shower before his guests arrived. He opted for a robe after his shower, figuring there wasn't much point in putting anything else on. He went to the kitchen, pulling bottles of Hendrick's gin and Grey Goose from the cupboard along with martini glasses, cucumbers, lemons, and a bottle of olives that he had purchased for guests. He had no idea why people insisted on polluting perfectly good booze with the rancid things, but to each his own.

Cindy was the first to arrive, her pretty blue eyes framed by her blonde locks, her figure obscured by a light blue sundress. Jack bent his neck and kissed her hungrily once the door had shut behind her. He pushed her against the door, one hand on her breast, the other kneading the warm flesh of her ass. She moaned into his mouth and he could feel her nipple harden in the palm of his hand beneath the thin fabric.

"I Skyped with Max today," she gasped as their lips parted. "Debbie told me that it was OK to let him in on their arrangement with you. I thought he was going to cum right then and there." She giggled, happiness twinkling in her eyes. "Apparently there is an issue with the company's field system, something about the 'scope of existing data not being sufficient for indications of success given current mission parameters.'"

Jack smiled at her. He was happy that she had thought it important enough to get this detail right: it boded well for her marriage.

"So that means that Max will be back here by tomorrow night!" She bounced with enthusiasm as she spoke, and Jack was made even happier still.

"Fantastic!" Jack replied and was a bit surprised to find out that he was actually looking forward to seeing Max again. He thought it likely that Cindy's willingness to indulge his fantasies would lead to Max fulfilling her needs, which would engender her gratitude and libido. A virtuous cycle from beginning to end, he thought wryly.

"Can we have another party then too? I really want Max to be here."

"Of course," Jack replied, "the more the merrier."

He had just finished mixing martinis in a shaker when the doorbell chimed, indicating the arrival of Debbie and Bill. He ushered them in, taking yet another bottle of wine from Bill thinking he'd have to start drinking the stuff eventually or he'd run out of space.

He shook Bill's hand, taking in the tucked in polo shirt, khakis and boat shoes.

Debbie, on the other hand, was dressed to the nines in a low cut, strapless cocktail dress that stopped just a few inches above her round ass.

"Where's the stuff I asked you to pick up?" Jack asked Bill in a friendly tone.

Bill colored. "I-, I wasn't able to stop. Debbie had us running around all afternoon and we ran out of time."

"Is that true?" Jack asked, looking at Debbie who had frozen with the shaker of martinis in her hand. "Did Bill tell you that I told him to get a few things for me? And you decided to do other things instead?" His tone had cooled several degrees and he took a sip of his libation, the cucumber floating lazily in the gin.

Debbie flushed as her husband had. "I-, I mean we-," she stammered. "I wanted a new outfit for tonight. Something risqué. And I wanted to get my nails done." She glanced down at her drink as she said this knowing that there would be punishment to follow.

"I'm disappointed," Jack said quietly. "Given what was on the list, Bill, I would have hoped that you could have impressed upon Debbie the importance of the errand. For your part Debbie, you know what happens when you disobey me."

The couple glanced nervously at each other, then Jack. Cindy sipped her martini quietly, a faint smile tugging at the corners of her mouth.

"Bill, come over here next to Debbie. Drop your pants and underwear and put your hands on the island." Jack's voice allowed no room for argument and Bill moved forward, his hands fumbling with his belt. Reaching the indicated spot, Bill pushed his pants and underwear down, his shirt partially obscuring his manscaped genitalia.

"You know what? Take your pants and shoes all of the way off. Lose the shirt too." Jack figured if the party was to get started then he should do it properly. "What do you think Cindy? How does Bill measure up to Max?"

Cindy blushed, eyeing her neighbor, her friend's husband. "He's bigger, but that's not saying much. I can understand why Debbie needed more now."

The color in Bill's face flushed more deeply and he leaned forward to rest his hands on the counter.

"Debbie, you're going to spank Bill for failing to do as I asked. He must learn that when I ask for something to please you both with he must deliver."

Debbie looked at her husband guiltily but set her empty glass down and stepped forward. She rose her hand and gave Bill's pallid cheeks several brisk swats before Jack stopped her.

"Have a drink Bill, but don't cover up," Jack said in a friendly tone indicating that Bill was forgiven. "Tell me about what happened when you two went home the other night and your thoughts on last night and this morning."

Bill spoke, reciting his version of reclaiming his wife, of eating cum from her well-used hole. He grew more animated as he spoke, clearly relishing the details of the encounter. "And as for last night, hell, I couldn't stop jerking off to the thought of these two together," he said, indicating Debbie and Cindy. "I can't wait to join in myself."

"You understand that you only play as requested, right?" Jack queried.

"Of course!" Bill said hastily.

Debbie had relaxed against the bar during her husband's recital of events, re-filling both Cindy's glass and her own. Jack beckoned her over, indicating that she should stand in the place previously occupied by her husband.

"You know the drill. Hands on the counter. You bullied your husband into doing what you wanted instead of what I had asked." Jack's hand slid from her lower leg up and over the curve of her ass and onto her back, tracing a line up her body. She shivered slightly and spread her legs a bit more. "You know what I'm going to do now, right?"

"Yes," was Debbie's soft reply.

"Look at your husband," Jack said quietly. "Don't stop looking at him or it will only be worse."

Debbie lifted her head in her husband's direction. Bill's penis was at full attention and leaking precum profusely. Jack pulled the top of Debbie's dress down and her tits swung free. One hand sought them out, tweaking her nipples, slapping them lightly. His other hand raised her skirt up over her ass. Thoughtful of her to forgo panties, Jack thought.

"Are you ready to watch your slut of a wife be punished for failing to obey another man?" Jack asked Bill.

"Please." Bill's response was full of lust. Jack heard years of submission to Debbie's will rising to the surface, willing Jack to dominate, to punish the woman who he loved completely, who dominated him so completely.

Jack's hand had slid between Debbie's legs and was teasing her wet, swollen lips. He dipped his finger in to her juicy hole and then circled her clit but didn't make direct contact with the little bud. Debbie's hips writhed against his touch, bucking at him, trying to get additional stimulation. Jack looked at Bill while he groped the man's wife, using her most intimate places for his selfish pleasure.

Jack's hand quickly rose and fell repeatedly, as Debbie's ass clenched and shimmied in a vain attempt to avoid the blows. His cock hardened, tenting his robe and threatening to make its presence known.

He stopped after a dozen swats: Debbie's ass had taken on a shade closely matching her dress. "Lose the dress," he told her, "we're heading for the bedroom now."

Bill quickly downed the rest of his drink and led the way followed by Cindy, then Jack and finally Debbie.

Debbie had managed to remove her garment by the time the crew had assembled next to the bed. "Cindy, are you OK with playing in front of Bill?" Jack asked.

"I talked with Max, and he's OK with it as long as he can do the same eventually. He just wants to be treated equally," she replied.

"I didn't ask what Max thinks. I asked if you were OK with it." Jack stepped towards her and kissed her hard before pushing her forward so that she caught herself with her hands on the bed. He roughly grabbed her ass with his right hand, kneading her big cheek over the thin dress, his fingers in her crack.

Cindy groaned. "If that's what you want then that's what I want," she replied.

Jack tugged at the hem of her dress, pulling it up over her the glorious white acreage of her supple ass. He couldn't resist and slapped each cheek once. Cindy yelped and tensed with the blows before relaxing when she realized no more were forthcoming.

"What was that for?" she gasped.

"You can't walk around with that ass and not expect me to spank it," Jack replied with a grin.

She smiled sheepishly at him in response, flushing at the compliment.

"Did you like that Bill? Did you like seeing me spank these women? Do you like how they are completely at my mercy?" Jack asked Bill, unsure whether he'd get a response.

Bill gulped. "Yes, yes I did."

"Do you wish that you could switch places with me? That you could be the one in control?"

"I do," Bill replied, and looked like he wanted to go on but stopped.

"But," Jack replied finishing the unspoken thought for his neighbor, "I think everyone here knows that you can't satisfy your own wife with that tiny needle dick much less both of these vivacious women. I'm curious though Bill," Jack continued, an idea forming, "what would you do if you had both of them at your disposal? What would you make them do?"

"I'd want to see Cindy naked." Bill's reply was too quick for Debbie's liking and she scowled, firing up immediately.

"Excuse me? Hello?" She gestured at her own spectacular form.

"Easy," Jack said to Debbie. "Bill must be able to tell me everything he wants to do. Openly. Honestly. Without judgement. Because I'm going to do every single one of those things to you ladies and he's going to have to sit and watch without touching himself, knowing that this is as close as he'll ever come to realizing these fantasies. He watched as I took his wife, now he'll watch as I take his deepest fantasies."

Jack felt his eyes smolder as he looked from Debbie to Bill. He turned to Cindy. "Strip. Show Bill what he'll never have."

Cindy's eyes widened but she obeyed and lifted the dress over her head, her large breasts dropping free and bouncing magnificently. The large pink areolas crinkled under the combined gaze of the other three and her hands reflexively moved to cover herself.

"No, let him look." Jack said, and Cindy's hands dropped. Jack spun her around so that she faced away from the couple. "Spread your legs and then bend over and touch the floor" he directed. He saw her face color but again she complied with his directive. Her breasts and golden locks obscured her face and Jack reached and spread her cheeks for the audience, putting Cindy on full display.

"Nice, isn't it Bill?" he asked rhetorically and leaned forward to run his tongue from her clit through her small lips and finally over her rosebud before standing again. "She tastes divine. You know I've had every one of her holes, just like I've had your wife's." As he spoke he lightly slapped Cindy's ass, indicating that she should stand. "So what next? Be honest, tell me."

"I-, I want to see them kiss," Bill stammered, indicating the women.

Neither moved. "Do it," Jack demanded, steel in his voice.

The women embraced, awkwardly at first but quickly melting into each other's arms. Bill's eyes displayed his rapture and Jack was happy at how well things were progressing.

"What next?" Jack asked as he slipped his robe off. As his relatively soft cock came into view he saw all eyes lock onto it.

Bill was momentarily transfixed but pulled himself from his reverie "Debbie should give Cindy kisses down there while I make love to her from behind. She never lets me do that." Bill's face flushed and he looked furiously at the floor. Debbie's eyebrows went up and she looked from her husband to Jack. Cindy had colored as well.

"Sounds hot," Jack said with a grin. "I get what Debbie means now: 'kisses down there'? What the fuck?!" Jack laughed at Bill, and the women joined with chuckles of their own.

"We're going to do just that though, except I'm not ready to fuck your wife yet. You're going to have to get me there and the women are going to help. Debbie, feed your sissy husband my cock. Cindy, you'll need to help push his head down. I want him to feel me in his throat."

Bill looked mortified. Jack saw a grin spread on Debbie's face as the women moved to position themselves, Debbie behind him, those glorious tits pressing into his back, Cindy at his side.

Debbie spoke up, surprising Jack "On your knees Bill."

Bill moved into position and Debbie's fingers closed around the root of his shaft. She spoke quietly in a low, insistent voice, addressing her husband. "I want to you to feel his cock grow in your mouth as I have for the past few days." She was rubbing the head of Jacks soft cock over his closed lips. "I want you to learn to love the taste of his dick, to love the sensation of his soft meat hardening in your mouth." He could feel her breath on his shoulder.

Bill's mouth opened slightly, and Debbie seized the opportunity, pushing the crown of his cock between her husband's thin lips, both husband and wife moaning as she did so. Jack felt his shaft slide across his neighbor's tongue and down his throat. Debbie pumped his shaft as Bill sucked, bobbing his head into the crotch of the naked man before him.

Jack pulled Cindy into him, crushing her left breast against his shoulder and mauling her right one. "Excited about seeing Max do the same?" he questioned softly in her ear. She moaned softly and ground her wet slit into his thigh in response. "Why don't you practice some? Push his head down, make him take me into his throat."

Debbie removed her hand and watched her friend tentatively place her own on the back of Bill's head and push his face down on Jack's now turgid rod. Debbie and Cindy moaned softly at the sight and Bill's eyes were watering when she finally released him.

"That's a good sissy bitch. Your reward is to watch me take this next fantasy away from you too. Stay put and no jerking that tiny clit of yours either." Jack's voice wasn't hard, but it left no room for dispute. "Ladies, assume the positions."

Cindy crawled onto the bed and rolled onto her back, her breasts sagging off the sides of her chest under their weight. She spread her legs lewdly and looked at Debbie with a devious look in her eyes.

Debbie moved forward, climbing on hands and knees onto the large bed. Her head dipped and settled between the blonde's ample thighs, and Cindy sighed as the brunette's tongue made contact. Jack positioned himself behind Bill's wife and traced his hard, wet cock through her slippery lips.

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