New Jack Ch. 10

Jack felt the head of his cock find Allison's wet entrance and slowly pushed in, savoring the first penetration with a new partner. Allison was incredibly tight, and he watched her face contort with his intrusion as Debbie released him.

"Holy shit! I've never...ungh..." Allison gasped as she writhed on the bed beneath Jack's steady invasion. He finally bottomed out, fully sheathed, and ground his hips into hers. Debbie had latched her pretty mouth to one of Allison's breasts while her hands harried the other. Jack's lust rose as he began to withdraw his cock, watching Allison's large lips gripping his shaft as he pulled back before sinking into her velvety tightness again.

"Fuck me!" Allison moaned. "I'm staying. I'll come back whenever you want, just don't stop, either of you." Debbie had repositioned herself, slipping a hand between Allison's legs. This position left her ass upturned to Jack's right, and his right hand released it's hold on Allison's thigh to slide two fingers into her engorged lips.

Jack had settled into a steady rhythm of deep, strong strokes into Allison while his fingers lightly tapped Debbie's g-spot. Both women were moaning unabashedly now, Debbie's head hanging, draped in a curtain of brown hair as she bucked back against his invading fingers.

Allison was the first to cum, and Jack felt her begin to contract on his throbbing cock while her face became a mask of pleasure. Neither he nor Debbie slowed in their assault of the statuesque red head's sex and Allison absolutely howled her way through her climax.

He and Debbie slowed before Debbie finally removed her hand, offering her drenched fingers to Jack. Jack licked each one, tasting Allison's release before coming to a halt, fully sheathed in the pale woman.

"I've never cum like that before," confessed Allison through ragged breaths. "I never thought I'd be able to cum during penetration. You stretched me out just right. Holy fuck," she gasped, finally collecting herself. "Didn't you cum?" she asked Jack.

"No, not yet," he replied with a twinkle in his eyes. "I wanted to make sure you were hooked."

"Hook, line, and sinker," she replied with a smile.

"Fantastic," Debbie breathed, inserting herself in the conversation.

"Now, Allison, where would you like me to cum?" Jack asked with a grin.

"Hmm," she replied, and Jack began to piston his tool slowly inside of her. "Oh," she gasped softly, "I don't know. Where do you want to cum? I owe you that much at this point."

"We can give you the Cindy special if you like," Jack said, his grin broadening as he looked at Debbie. Debbie's eyes lit up and she giggled at the prospect. "This is Cindy's absolute favorite," Jack continued. "Though I should warn you, you're going to be absolutely drenched. Sound good?"

"First vodka, now this. Sure, I'm game," she replied, a note of boldness infusing her dulcet voice.

"Great. You just slide off the edge of the bed here and sit on the floor. You're going to get to return the favor you owe Debbie." Jack's words set the two women in motion and once Allison was seated on the floor Debbie swung her leg over Allison's chest, straddling her face.

Debbie's gasp was audible as Allison's tongue began to explore her. Jack watched the sapphic tableau for a moment as Allison's creamy hands dug into Debbie's tanned ass cheeks, pulling her onto her mouth. He stepped forward, positioning himself behind Debbie and placed his hands on hers. He gently pulled her right hand from Debbie's ass and murmured "You should touch yourself too."

Allison's hand slunk out of view and he heard her moan into Debbie's snatch. Satisfied, he guided the head of his cock forward and into Debbie's welcoming vagina.

Debbie moaned as his cock slid into her, stretching her out. His balls finally tapped against Allison's chin and he withdrew just as slowly. He wanted to time his release with Debbie's and so began to build his tempo slowly bringing her along to climax as his own became more inevitable. His left hand released her jiggling ass and he licked his thumb, wetting it. He pushed it against her crinkled star, invading Debbie as his right hand spanked her.

Debbie's reaction was immediate, and Jack could feel her cresting the wave of her orgasm. He slapped her ass again as she bucked her hips back against his cock and thumb. Jack felt the Debbie release, a shower of warm juices coating his legs as his own cock threatened to explode. Out of sight, Jack heard Allison's shriek, signaling her own self-induced climax.

Sliding out of Debbie he caught his first sight of Allison's face, glistening with Debbie's fluids as he pumped his cock with his hand. "Open up: I want to see your tongue."

Allison complied just in time to receive the first shot of what would be a torrent of Jack's cum. He erupted over and over; the cum that didn't land in her mouth sliding off her face and onto her pale breasts. He stepped forward, placing his sticky, deflating member into Allison's open mouth and she readily accepted it, caressing his tender flesh with an eager tongue.

Debbie slid off the bed, pooling herself next to Allison. She began scooping Jack's cum off her and alternated cleaning her finger with her own mouth and feeding it to Allison. Jack retrieved some wipes from the nightstand, passing them to Debbie to clean her friend more thoroughly once most had been collected.

"I can see why Cindy likes that," Allison said with a chuckle, finally able to open her eyes. "That was fucking intense. You never told me that you squirted," Allison said accusingly, turning to look at Debbie.

"I never had before until Jack," Debbie replied with a shrug. "Bill doesn't have the equipment and I guess I just couldn't let go enough with anyone before I was married. Fucking Jack has been amazing. He's really pushed my boundaries but I still feel safe and I always cum," she finished with a giggle.

"I don't doubt it," Allison said, looking at Jack with appraising eyes. "I've always been more dominant than submissive in the bedroom but I can see the appeal in letting him take control. I've never felt the way that I did when you two worked on me."

"Just wait until Cindy comes over," Jack said with a chuckle. "You'll get your chance to be dominant if you want."

Allison's face clouded, "I don't want to fuck Bill or Max. No offense Debbie," she added quickly, glancing at the brunette.

"None taken," Debbie replied. "I know Bill isn't much to look at, but we've got a great relationship outside of the bedroom. And there's no way in hell I'd let Max touch me. The boys only get to play as Jack lets them, and any play they get is mostly humiliating."

"Like what?" Allison asked, her curiosity aroused.

"He usually won't let Bill cum unless Bill's mouth is on Jack's cock!" Debbie squealed.

Allison's eyes flew to Jack's face and he shrugged. "I decided to push my own boundaries as well. I'm not attracted to men, and I don't think Bill is either. But it's fucking hot to dominate a couple like I've been doing with Debbie and Bill. Hell," Jack continued, "I even made Bill and Max suck each other off after their wives fucked their asses with strap-ons."

The women had joined Jack standing next to the edge of the bed as he spoke. Allison's eyes blazed with newfound excitement while Debbie's smoldered their brilliant green at him.

"I don't believe it," Allison said pensively. "I've known you guys forever. Bill doesn't seem like the type, though I wouldn't put anything past that pervert Max."

"Care to make another wager?" Jack asked Allison, a glint returning to his own eyes.

"You're on," she replied confidently.

"What's the challenge then?" questioned Jack. "I can make them do anything."

"They've got to fuck each other," Allison replied immediately.

"That was quick," Jack replied with a laugh and Debbie joined in. "Though I'm not sure that Max is packing enough to make it happen. How about we only make Bill fuck Max?"

"Not packing enough?" Allison repeated, questioning the pair.

"He's even smaller than Bill!" Debbie gushed. "And Bill's four inches long tops and thin. Max's pecker looks like the last knuckle on your thumb!"

"Poor Cindy," Allison lamented.

"And did you know that Max refused to use toys with Cindy? The poor woman had never had a proper orgasm until this past week when Jack showed up." Debbie's face and upper chest were flush with her arousal at the memory of their previous encounters and men's humiliation at Jack's hands.

"After what just happened, I'd probably put myself in the same boat," Allison mused. "So, what are the stakes? How does this work?"

"Truth be told, I've been leaving Max on the sidelines more than I should," Jack confessed to the women. "If you agree, then Max will get to direct the action. You won't interact with him or Bill though. But you must agree to let the husbands see you nude and to do anything with Cindy, Debbie, and me that he requests. Can you live with that?"

"What do I get if they won't do it?" Allison asked.

"Anything you want," Jack said with an easy smile. "Because that's what I'm going to take from you when Bill fucks Max on my orders. Deal?"

Allison hesitated, a defiant look in her eyes. "Deal," she finally agreed. "When are we going to do this?"

Jack glanced at Debbie. "I suppose there's no time like the present. Debbie, can you get Bill, Cindy, and Max over here by 7? We'll leave everyone to their own devices for an early dinner and meet here for a 'pool party' after. Sound good?"

Debbie readily agreed, bouncing on the balls of her feet so that her naked breasts jiggled enticingly. "But I better run home and get everything ready. See you in a bit!"

She pressed her nude form into Jack's, kissing him deeply. Jack's hands wandered down to her ass, gripping her cheeks tightly before delivering a light slap that broke their kiss. "Hurry back," he said to her as she skipped out of the room to find her dress.

"Care to stick around until then?" Jack asked Allison. "I really don't have anything planned for the rest of the day anyway."

"Sure," she replied easily, "but I don't think you should get any ideas just yet. Sounds like you might need your energy later."

"You're right, but what interests me most is that it sounds to me like you're hoping to lose this bet." Jack's eyebrows arched questioningly at her.

"Maybe I am, maybe I am," she responded softly.