New Jack Ch. 03-04

"Hey, no fair!" Debbie shouted as Cindy whooped. "You're going to scare Jack away."

"Not likely" Jack responded. "Not if you keep wearing that outfit."

Confused, Max looked around but couldn't see her above him. "Well" Debbie said as she stuffed herself back into the top "it's not like you haven't seen tits before."

At this Max almost broke his neck attempting to swivel his head and looked apoplectic at the thought of getting to see Debbie's glorious breasts. "Let's switch" Debbie suggested. "We'll let the husband and wife have a go at us. Sound good Jack?" Jack thought her smile was the perfect capstone to the double entendre.

Jack sank to a crouch, allowing Cindy to slide off his shoulders and felt Debbie climb on. Standing, they watched Max struggle to lift Cindy. Finally rising completely, the two couples faced off. Debbie fought dirty this time and within minutes Cindy was down. "One more time!" Debbie's cry seemed to push Max, who undoubtedly was hoping for a repeat of Cindy's victory over the topless Debbie.

Jack forced the two couples together and a moment later heard a shriek followed by Cindy's laughing accusation: "You bitch! You did that on purpose!"

"Fair's fair" Debbie countered, holding the top of Cindy's bikini. Jack's eyes were focused on Cindy who was alternately trying to cover her breasts and holding on to the stumbling Max. Eventually she gave up and fell over backwards off him. Debbie threw Cindy's top onto the lounge chair and tumbled backwards off Jack, rising quickly to whisper in his ear "Step one is complete. Play along in a bit, you'll know when."

Grinning, Jack watched Max swimming over to Cindy who was climbing the ladder out of the pool. Her heavy breasts swung pendulously, capped with light pink nipples and large areolas. She strode over and retrieved her top, putting it back on to the sound of Debbie boo-ing.

"I owe you for that one" Cindy scowled playfully.

"Let me get some margaritas to make up for it" Debbie replied. Jack sat down next to Max who had apparently decided to forgo the game on TV. A small end table was between the chairs and Debbie returned to the group with a tray bearing four glasses and the margarita pitcher from yesterday. She set the tray down, though it hung off the end of the table precariously. "Ladies first" Debbie said and poured a glass for Cindy before passing it over. "And next for our generous host" she proclaimed and turned towards Jack, pouring the drink while leaning over him. She set the pitcher down on the tray right next to Max. As she leaned to give Jack his drink her hip bumped the table, causing the pitcher to spill all over Max. At the same time she dumped the full glass all over Jack's lap while turning to see what the commotion was.

Both Jack and Max jumped to their feet. Cindy's laughter rang out like bells. "I'm so sorry. I'm such a clutz sometimes" Debbie whined in an apparent panic.

Jack chuckled "It's not a problem. These things happen. We can rinse off in the shower and I'll dry our clothes." He stood and began walking over to the shower, trusting this was part of Debbie's plan. "Come on Max. You don't want that stuff to dry."

Max had the flighty look of a caged bird dying to be set free. He took a step, paused, and then followed Jack reluctantly. "Are you ladies going to give us any privacy?" Jack asked, feeling that he knew the answer already.

"Absolutely not" Debbie retorted. "You've seen both of us topless today. Turnabout is fair play."

"I didn't get to see you though" Max whined.

"Am I not enough for you?" Cindy demanded at the same time as Debbie's indignant reply of "I'm a married woman. I'm not showing you my tits just because someone else saw them."

Cowed, Max turned as Jack turned on the spray. He looked up to catch a wink from Debbie. "I suppose you both have a point. Well, let's get this over with." He was thankful that he had a little blood in his shaft at the moment. Wouldn't do to disappoint the audience he thought.

He pushed his suit down, stepping out of it, feeling the warm sun on his whole body now. He stepped into the shower, rinsing his hair and then rubbing his crotch. If anyone asked he would just say that he was getting the sticky margaritas off.

He opened his eyes as he stepped out of the spray, leaning to grab his suit from the railing. "Max?" he said questioningly.

Max blushed but finally stripped off his wet shirt to reveal a large pasty white body. He pushed his shorts down to reveal trimmed, dark red pubic hair and small penis protruding an inch or so beyond it.

"Oh my god, are you hard!?" Cindy exclaimed. "Why are you hard?"

Max didn't answer but flushed red and ducked into the shower. He quickly rinsed and grabbed a towel, attempting to wrap it around himself. The effort was in vain because the normal size towel wouldn't quite wrap around him completely, tug at it though he might.

"Let me get you another" Jack offered and walked confidently between the two ladies, the head of his cock bouncing with the rhythm of his stride.

He passed Max the towel upon returning and Max quickly exchanged the two pieces of fabric. "Cindy, let's go. I need to pack up the car and get on the road by 6." His voice was hard, brittle and Cindy looked crestfallen.

"Nice to put a face and a name together" was the best Jack could muster and he offered his hand to Max again. Max took the naked man's hand and gave it a brief shake before turning to leave.

"Hope to see you soon" he said to Cindy and extended his hand to the buxom blonde. She took his hand, clearly a bit flustered and pressed it warmly between her own.

"I better get going. I'll text you later Debbie. Are you OK?" she had realized that she was leaving her very married friend in the company of a naked man.

"Sounds good. And I'm fine. Jack knows what the boundaries are." Her grin told Cindy more than she meant to.

Jack grabbed a towel now for propriety's sake and walked Cindy out. "Feel free to come over and enjoy the pool anytime" he said, and she flashed him another smile as she walked out to join her husband.

Jack closed the door and pondered his next move. He had really hoped that Debbie would be able to deliver on her promise, but things weren't looking good. He had to figure out a punishment, but his stomach was rumbling and he figured he might as well deal with that first.

Stepping out onto the patio he found Debbie nude, her wet black suit hanging on the back of the lounge chair that she had stretched out on. His cock stiffened in his pants as he admired her form. Her tits sagged to the side of her chest and the trimmed brown strip of hair above her pussy looked absolutely edible.

"I'm going to go ahead and start the grill" Jack said. "I'll give you until the end of our meal to get Cindy back over here, or else." He had no idea what 'or else' meant, but he figured he could just improvise if needed. There were so many things he wanted to do to her that he wasn't sure where to start.

He started the grill and left her furiously texting to grab the burgers that were resting in the kitchen with the associated trimmings. He left the towel in the kitchen, returning to the grill and setting the patties on to sear. Walking over to Debbie who was still reclined on the lounger he swung a leg over and moved up to straddle her face. "Lick my balls" he said and grabbed her phone from her.

He felt her tongue on his heavy sack, coating the crinkled skin with her saliva. He slowly stroked his cock, occasionally slapping it against her face. He had no intention of cumming just yet but wanted to edge, to build up a really big load in case Cindy made it back. He opened the camera on her phone, snapping a picture of her face, partially obscured by his long rod but it was clear that her mouth was full with one of his testicles. He texted the picture to Bill and himself before dropping the phone onto her stomach.

He stepped off of her and she wiped the spittle from her mouth. "Cindy is getting Max on the road and will be back in a few minutes" she said with a grin. "Don't worry, I'll make it happen. I want to taste your cum so badly. Bill raved about it last night. He said it was the hottest thing that's ever happened to him. He attacked me when we got home and lasted for about two pumps when he got inside me. He was over the moon. I made him eat it out of me: we hadn't done that before. I think he's developing a taste for cum."

Jack chided himself for not following up on the couple. "I'm glad you two reclaimed each other. He's going to have a thoroughly worn out wife by the time he gets back from Miami if you can't manage Cindy."

Debbie giggled. "Promises, promises."

Jack returned his attention to the grill and the charring meat thereon. He was just taking the last of the burgers off when the doorbell chimed. "I'll get it!" said Debbie, stepping into her suit bottoms and stuffing her breasts into the tiny top. Jack had opted to put his suit back on while tending the grill. He figured there was no reason to tempt fate.

Cindy and Debbie bounced out of the house, giggling lightheartedly as they came over to the bar. Jack dropped the plate of meat next to the toppings and buns and offered margaritas to the buxom friends. "God do I need one after that" exclaimed Cindy. "Max is insufferable sometimes" she went on between mouthfuls of burger. "He can be really sweet when it's just the two of us, but I think he feels threatened around other men. Especially men like you Jack." Her blue eyes ran up and down his body and Jack's hopes began to rise again.

"What do you mean 'men like Jack'" asked Debbie. "Jack was perfectly nice and a great host. Max never gave him a chance. He was pouty the entire time I saw him."

"He's insecure about, well, you know, you saw..." Cindy's voice trailed off and her face flushed with color.

"Bill isn't much bigger though" Debbie replied. "He's not threatened by Jack. He knows I'll only ever love him even though he has a tiny dick." She giggled and glanced at Jack. "Something similar happened yesterday. Both guys wound up messy and had to strip in front of me and shower off. Jack didn't seem to mind. I'm beginning to wonder if he isn't a bit of an exhibitionist."

Both women looked at Jack appraisingly, searchingly. He felt his face color a little but replied in a calm voice "It's no big deal. We're friends and it's not like I've got something you haven't seen before."

"Well we sure have seen it now" Cindy chuckled before pushing her plate away. "That was delicious, thank you for that." She colored. "The burger, I meant the food" she hastily added, blushing further.

The two others laughed good naturedly. Everyone stacked their plates and Debbie topped their drinks off. Dusk had arrived and as the women took the dishes inside Jack lit the tiki torches around the hot tub and turned on the heater and jets. Thankfully the spring weather lent itself to reasonable temperatures at night and Jack was hoping that the warm water and alcohol would lower everyone's inhibitions.

"Can we get in?" Cindy queried. "I haven't been in a hot tub in ages. I could really use a good soak after Max's antics."

"You should know" Debbie piped up as Cindy stripped her sundress off to reveal the same bikini from earlier "that Jack told me that there is a strict no-clothes policy in the hot tub once the sun goes down. But I really need a soak myself."

With that said, Debbie reached behind her neck and released the string holder her top up. Her breasts spilled into the early evening light and both Jack and Cindy watched her nipples harden, crinkling and tightening the size of her areolas. "It's not like he hasn't already seen them today" Debbie said nonchalantly and she proceeded to shimmy the black bottoms of her swimsuit down her shapely brown legs before stepping out of them and into the bubbling water.

"Naughty girl" Cindy said in mockingly reproving tone. "What would Bill say?"

"Let's find out" Debbie replied and turned to grab her phone. Jack felt begin to rush to his cock which stirred beneath his pants as he watched the water stream from her hanging, swinging tits. "Not that I need his permission. It's my body, I'll do with it what I want. Besides, he knows that I'll always come home to him."

Cindy's eyes widened a bit but she said nothing. "You heard the lady" Jack said, and he pushed his own bathing suit down and stepped out of it, his cock relishing the cool evening air.

Cindy seemed to falter for a moment and then shrugged. "Hell, you've already seen most of me anyway." She stripped off her bikini quickly and then turned to set the garments down on a chair. Jack gazed fixedly at her wide, white ass. She turned and her breasts swayed enticingly with the motion. Jack saw that her nipples too were harder than before, sticking out more prominently from her creamy breasts.

"So are you a natural blonde?" Jack asked. "I can't tell." The comment earned him a flustered look from Cindy and a chuckle from Debbie.

"Yes, I'm naturally blonde" Cindy replied and splashed some water at him as he stepped in. "I just prefer to be smooth down there. It makes me feel pretty and desirable."

"If anyone tells you that you aren't desirable you need to send them to me for re-orientation. You look fabulous" Jack said and gave her what he hoped was a winning smile.

"Thank you" Cindy said, relaxing a bit. "I wish Max thought the same. He's never been very complimentary towards me. It goes against my principles, but I secretly enjoy getting catcalled and whistled by strangers." She blushed with the admission. "I've just never felt very comfortable in my skin I suppose. I work hard on my body, but I'll never be model thin. I'm becoming more and more OK with that though."

"Well I think Max is an idiot if he can't appreciate you" Jack said.

Debbie nodded her agreement. "Bill worships the ground I walk on and I carry a few extra pounds. Max has no room to talk. He should be grateful that you even get into bed with him."

Cindy blushed hard at this. "He hasn't touched me in years. All he does is watch porn and jerk off. In the beginning he was attentive, but he wasn't very good." Her blush deepened, creeping down her pale chest. "He never felt adequate because of his size and didn't want to use toys because he felt like it made him less of a man that he couldn't get me off with any part of his body including his hands and tongue. God, I can't believe I'm telling you this." She grabbed her margarita and drained it. "I'm empty. Who else needs more?"

Jack stood, sensing the friends may want to talk for a minute in private. He went to the bar, taking his time while squeezing the limes and making another pitcher of margaritas. The women were still in hushed conversation when he returned but broke off when he was in earshot. He refilled Cindy's glass and topped off Debbie's before setting the pitcher on the edge of the tub.

"Cindy just told me that Max watches the same type of cuckold porn that Bill does. Like me, he has given her a hall pass but she always felt icky at the thought of using it" Debbie's tone was that of a moderator, calm and almost disembodied. "I want to try something, and I feel safe with Cindy here. Will you sit up on the edge of the tub Jack?"

"I'm never one to turn down the request of a pretty lady, especially when she's naked." Jack grinned at her and he thought she did a good job of feigning embarrassment.

He stood up, his cock and balls hanging very low because of the warm water and sat on the edge of the tub with his legs splayed. Debbie grabbed Cindy's hand "Come with me" she said and pulled her naked friend through the bubbling water to before stopping in front of him. "Can I touch it?" Debbie asked, and Jack nodded.

She reached out and then cupped his balls, rolling them in her slim fingers. She released them and grabbed his shaft, slowly stroking it before rubbing her thumb over the tip of his hardening cock. "It's so much bigger than Bill's. It's so warm and soft. Cindy, you've got to feel this. I'd forgotten what a big one feels like."

Cindy blanched but the peer pressure overrode her hesitation. Her pale arm extended as Debbie's brown one withdrew. She grabbed the shaft, and slowly stroked him as Debbie had. "I've only ever been with Max. I've never seen one this big in person." Her eyes had a glazed look and she moved her other hand forward, pressing her big pale tits together making an incredible valley of cleavage between Jack's knees. Jack's rod was now completely hard and a bead of precum formed at the top of his cock. Cindy swiped it with a finger, coating the head of his dick. Debbie's phone chimed with a text message, breaking Cindy's trance.

"Bill says that I should let loose and enjoy myself with you two in any way I want, with the only rule being that I tell him any juicy details" Debbie read from the small screen. She looked up at the pair, beaming. "I'm declaring Monday night at Jack's to be ladies' night!" She raised her glass in a toast and Jack grabbed his to toast her back. "Cindy, are you going to drink with us?"

"I'm just going to have a small taste" she said in a quiet voice. Glass in the air, Jack watched as the woman bent forward and licked the newest bead of precum that had formed at the end of his throbbing cock. "I may have more later. After all, it is ladies' night." She blushed with the audacity of her actions.

"Who's being naughty now?" Debbie asked with a giggle. "I want to try too. Blowing Bill will be nothing like what it would be like to try to swallow what Jack's packing here."

Debbie leaned forward and sucked Jack's cock into his throat. Cindy's hand was still on the base of his shaft and Debbie's breasts were crushed against Jack's leg. Debbie bobbed her head and moaned as Cindy stroked Jack's cock into her friend's mouth.

"Come up here with me" Jack requested. "It'll be easier on your arm." Cindy rose, relinquishing his cock for a moment and moved next to him as Debbie slid between Jack's legs.

"Feed it to her. Feed your friend my cock" he said softly. Her hands moved between his legs and grasped him, stroking his shaft while Debbie's head bobbed up and down.

"May I?" he asked, looking into Cindy's pretty blue eyes. "Yesss" she hissed and thrust her face against his, their lips mashing together and tongues tangling furiously as her grip on his cock tightened. His hand found her breasts, kneading them, feeling the soft flesh yield to his fingers. Cindy moaned into his mouth, pushing her chest out and releasing his cock to grab his head with both hands.

Cindy and Jack's embrace continued as Debbie continued her oral ministrations. Jack's hand left Cindy's tits, traveling over the soft swell of her belly and finding its way between her thighs. Her lips were small and Jack dipped a finger into her vagina before tracing it up and around her little bud. "It's been so long" she moaned. "God I need this."

Jack teased her sex for another moment before pulling back, away from her embrace. Debbie sensed the change and paused, looking up at him expectantly. "Up on the edge next to Cindy" Jack directed. "It's ladies' night after all, and I'd like to taste both of you." Debbie grinned broadly as she scrambled up to take Jack's place. Debbie readily spread her legs, displaying her large meaty lips and swollen clitoris. Jack looked at her with a sly grin and then moved between Cindy's legs. Debbie moaned slightly, and Jack saw her hand drop so that she could touch herself while waiting her turn.

Jack slowly kissed his way down the inside of Cindy's thigh before reaching the nexus and its treasure. He inhaled her scent, mixed with the water from the hot tub. He flicked his tongue over her small lips and her moan of appreciation was music to his ears. His tongue continued to trace her lips, occasionally dipping into the wet center. Her hips were beginning to buck against his jaw, her clit desperate for attention. He finally obliged her, worrying the little bud as one of his fingers slipped inside her, rubbing the rough patch of her g spot.