New Jack (3 – 4)

3.

Monday morning dawned to find Jack already on the road, his sneakers beating a steady staccato onto the wet pavement. He had pushed on this run, still keeping the distance at a respectable three miles but working to drive his mile time down. He idly wondered why no one else around here was out jogging. There were plenty of lights appearing in windows but not a lot of movement at 6 am.

He saw the women as he rounded the next bend. Both relatively tall, ponytails swinging as they jogged along. As the pair passed under a streetlamp he recognized Debbie from the previous night’s adventure. She and her husband had snuck back to their house like teenagers under the cover of darkness after she had given him a deep kiss in parting. Bill had been grinning from ear to ear as he stuck out his hand to take his leave.

It had taken him a moment or two upon awakening to remember and reconstruct yesterday. His morning erection demanded attention, but Jack figured he could find a better use for the load and so opted instead to go for a run.

As the women drew closer he saw Debbie flash a brilliant smile and a quick wave. The blonde woman accompanying her merely nodded with a polite smile and then the two were past him, having received a nod and a smile from him in return.

He was just stepping out of the shower when he heard a knock on the door. Quickly throwing some athletic shorts on but forgoing a shirt he answered the door to find the women on his door step, flushed from their exertion. “Mondays are running days. Might as well get the worst of it out of the way” Debbie said with a grin. “Mind if we come in and cool off? Our husbands are both glued to their respective TV’s, eating Eggo’s or some other worthless shit.”

Blondie giggled at this. She was almost as tall as Debbie but was pale skinned and her curves were even more pronounced than her friend’s. Jack judged her to be a solid D, maybe even DD, cup compared to Debbie’s C. Errant strands of hair were plastered to both women’s necks, having escaped their ponytails.

“Can I offer you some water? Coffee? Tea?” asked Jack. “I also have some fresh fruit, bagels, cream cheese and lox if you’d like to have a bite.”

“Water would be great” said the blonde. “I’m Cindy by the way. Debbie told me that she’s helping you with decorating and that she and Bill came over yesterday for a swim and some delicious margaritas.”

“Did she now?” Jack asked. “Did she say that they had the time of their lives? That’s what I was hoping for.”

Debbie blushed but it went unnoticed by Cindy who laughed; a pretty, shiny sound. “No, she didn’t say that. But she said that I should get try to get the same invitation from you for my husband and me if possible.”

“The same one?” Jack looked pointedly at Debbie whose flush was now complete and was looking demurely at the floor. “I’d be happy to meet more of the locals. I’m assuming that you live around here?”

“We do, just one street over. My husband is a contractor for the military and will be shipping out along with a deployment for the next three months to maintain his company’s systems. Be careful with your invitation: you may not be able to get rid of me. We don’t have a pool and the weather is turning hot too early this year.”

Jack’s eyes held Cindy’s deep blue ones as she spoke, and he tried to make his smolder. Hell, he thought, I just may wind up with a harem. I wonder how many unsatisfied married women a neighborhood can hold.

“I’d be happy to have you and/or your husband over. I’d like to meet him before he ships out. Do you have plans for dinner tonight?” Jack queried and she replied that they had no plans. “Great” he said. “Why don’t you guys come over late this afternoon and we can play in the pool and grill some burgers.”

Cindy said that sounded great but wanted to double check with her husband before he left for work. She gave Debbie a quick hug and the air kisses that so many women do and flounced out the door.

“Call Bill and tell him that you’re having breakfast here. He’s welcome to come over as well. Then go rinse off.” His voice was calm but had that same new-found authority from yesterday. He found himself slipping into this role easily.

As she grabbed her cell phone he crossed the few feet separating them. He shoved a hand down her pants to find her vagina soaking wet. “Couldn’t even go twelve hours? You’re practically dripping” his fingers teased her and she moaned into the receiver, one hand steadying herself on the island as she spread her legs to give him better access.

“He’s not answering” she gasped as his other hand found her sports bra and pulled it up, releasing her breasts. God they were sexy Jack thought. He loved the way the areolas almost blended into the skin around them and marveled at their size. Sand dollars, he decided.

“Text him then” and she hastened to comply as he manhandled her body. He pulled her tit with one hand, twisting the nipple he did so. He removed the other hand from her pants and shoved his moistened fingers into her mouth. “Clean them” he said and relished in the sensation of her tongue darting between his fingers.

Finished texting, she set the phone down. “Shower, now. Then come back here” he directed her.

He watched her move away, enjoying the roll of her hips and ample ass and considered what he wanted to do next. Breakfast would be the most practical thing: his body needed nourishment after last night’s activities and this morning’s run. But his stiffening rod had other ideas.

Minutes later she stepped back into the room, nude. She hadn’t washed her hair, but he hadn’t wanted to wait that long. “On your knees” he said and she slowly sank down before him. She reached up, just as her husband had done the previous day and slowly slid the pants down to the floor. Her warm hand caressed his balls and she opened her mouth to accept his member. She moaned, her eyes closed as she sucked him deeper into her throat as her other hand flicked between her legs. Jack enjoyed the view, watching his fat cock stretch her pretty mouth. He let her work him to full size and then pulled her to her feet.

“Hands on the island, bend over” he said coldly. She giggled, wiggling her supple ass back at him. He enjoyed watching the ripples in the meat of her ass and he could see moist lips peeking from between her legs.

He spanked her unexpectedly, hard. It burned his hand and left a distinct outline on her ass. She yelped, pulling away and closing her feet together. “No” he commanded. “I told you to maintain eye contact with me when my cock is down your throat. You didn’t, so you’ll be punished you cock hungry slut. You touched yourself without asking too.” His hand fell again and again. Her ass was bright red and hot to the touch now.

He paused, caressing her burning flesh before dipping a finger into her canal. She was wetter than before, just as he had hoped. She moaned with the intrusion. “What did you tell Cindy about us?” he demanded.

“Nothing really” she panted. “I said that we met you yesterday and I thought you would be a good influence on Bill. I said you were a man’s man. Big frame, hairy chest, and that you were recently divorced. Maybe I joked about you setting up a harem but that’s it.”

“Is that what you want? You want me to have a harem?” Jack continued to tease her lips, now adding a finger. She writhed under his touch, spreading her legs again and bucking back against his hand.

“Yesss” she hissed.

“Why?” He was genuinely curious. He didn’t understand why she would want to share him with other women.

“I want them to feel what you did to me last night. I want to watch you take these women and make them your sluts like I am now. They’re just as unsatisfied as I was before last night. You can fix that. You can make my friends happy. I want to make them just as fulfilled” she replied, soft moans mixed in with her words.

“Tell me about Cindy” he directed.

“Her husband is fat. He’s lazy. She says that he has the tiniest dick she’s ever seen. I think it must be a micropenis.” Her voice had an edge and he could tell that she genuinely disliked the guy.

He removed his fingers and traced them upwards, circling her rosebud, then pushing the tip of one in.

“Ohhh” she moaned and pushed back against him again.

“Touch yourself” he said and her hand dropped from the counter and disappeared between her legs as he worked his finger in and out of her ass. “Are you bisexual?” he asked.

“I don’t think so. At least not really. I’ve never really done anything with a woman before, but I find some women attractive.” Her response, while not what he had quite hoped for was encouraging nevertheless.

He decided to push. New Jack pushed when he felt like it. Slipping another finger into her tight ring elicited another, louder moan. “You will help me bed these women. You will suck me hard for them. You will watch as I give them your stolen orgasms you dirty slut. You’ll watch as I wreck their tight snatches and the first time you taste my cum will be out of one of your friend’s pussies.” His words and the mental images drove her over the edge and he felt her tighten against his hands and shudder as an orgasm washed over her. “Tell me” he said. “Tell me you’ll do it.”

“Yes” she gasped. “Your cum, their pussies, all of their pussies. Their asses. Wherever. I need it.” The words were disjointed but Jack felt his flagging erection return to full mast with her affirmation. He had definitely picked the right neighborhood.

He stood, moving behind her. “Spread your ass for me. Ask, no beg, me to fuck you in your married ass.” His words felt cold in his mouth yet somehow natural.

“Please” she gasped. “Please fuck my married ass. Stretch it like my husband can’t. Make me scream. Take what you want.”

Her hands pulled her voluptuous cheeks apart, fingers sinking into the layer of fat. Her ass still glowed from her spanking, and he positioned himself, sliding into her tight cunt first to lube himself up. God she was tight. Bill’s skinny prick hadn’t done much to loosen her up over the years. She moaned and gasped as he stroked in and out a few times, thoroughly coating his shaft. He withdrew and placed the crown of his cock over her hole, the only one left to claim as his own. He heard her gasp and a small cry escaped her lips as the crown of his cock popped through her tight ring.

She let go of her cheeks, bracing herself against the island for support. He rocked his way into her ass, inch by fat inch until his cock was completely buried in her. He felt her fingers worrying her clit, occasionally brushing his balls. “So full” she murmured. “Never before, ugh.”

He eased back then slid all of the way in again. He could see their reflections in the window. Her head was bowed down and her tits swung enticingly as he began to piston in and out of her faster. Her cries of discomfort soon turned to moans of pleasure. He slapped her ass a few more times to bring the red back out and felt himself coming close to his own orgasm.

Wanting more, he withdrew and grabbed a stool, placing it next to the island. “Get up” he said and she turned, resting her burning ass on the seat. Her legs were spread and her tits hung, slightly drooping off the sides of her chest. He shifted her forward in the seat a bit, exposing her previously tight anal ring that now gaped slightly. He shoved his hard cock back into her ass and watched her face contort with pleasure and pain.

“Cum for me. Cum with my cock buried deep in your married ass. Cum while you feel me fill you up.” His words were growls and her face was a mask of ecstasy. He slapped a tit with the flat of his hand and her moan of approval brought him right back to the edge. Again his hand fell and then she was cumming, spraying him again, clenching hard on his cock, driving him to his own release. With a roar Jack unloaded, spraying her bowels with his seed.

She slumped back as he slowed, a light sheen of sweat on her chest. When he removed his cock her ass was truly gaping. He watched it pulse, re-forming now that the violent intruder was gone as his cum profusely leaked out of her wrecked hole.

“Your job now is to make sure I’m balls deep in Cindy tonight. I don’t care how you do it, just make it happen.”

She looked at him, still panting slightly. “I’ll do it. I’ll make it happen.”

4

Debbie left after dressing and grabbing a bagel on her way out the door. Jack cleaned up and set about catching up on email and then making a run to the local mall for some more Florida-appropriate attire. He didn’t think swimming in his boxers two days in a row would go over so well. He also stocked up on margarita supplies, figuring that if Debbie was using that as a selling point he had better be able to deliver.

He spent some time on the backyard in the afternoon, mowing, pruning, and ensuring the pool and hot tub were ready to go. He was sweaty and grimy when his phone alerted him to a text message.

Debbie: It’s all set. You just be yourself.

Jack smiled to himself. This was entirely too easy.

His doorbell chimed at 4 pm and he opened it to find Cindy and who he presumed was her husband on the step. “Hi neighbor!” she said in a bubbly voice. “Thanks again for having us over. I think Debbie is taking it as a personal challenge to integrate you to the neighborhood as quickly as possible. She mentioned that she thinks your place will become party central this summer.”

Jack rolled his eyes in mock despair. “Come on in. I’m Jack” he said as he turned to the man and offered his hand.

“Max” was the reply and the handshake was complete. Max was a portly fellow Jack decided. Probably a combination of unlucky genes and an unhealthy lifestyle. His reddish brown hair was thinning but what drew Jack’s eye was the bulge of his gut that pressed against the sides of a shirt that was too large for him in the shoulder.

“Nice to meet you Max. I saw Cindy and Debbie out running while I was on my morning jog and Debbie decided to stop by an introduce us once they were done. Come on out back, I think I’ve got us all set up.” As he ushered them in he realized that he agreed with Debbie: Max wasn’t someone he wanted to spend much time with. He seemed standoffish and had an air of entitlement that rubbed Jack the wrong way.

Cindy more than made up for Max’s dour personality. She gushed over the yard, the pool, the hot tub, and the bar while Max was sullenly silent. She was easy to talk to and the three of them grabbed drinks at the bar, Jack following Cindy back to the lounge chairs where the trouble had begun yesterday. He didn’t notice Max staying behind at first until Cindy mentioned it.

“Aren’t you coming? What are you doing?” she called to him.

“I’m going to stay here in the shade” was his monotone reply.

Cindy rolled her eyes. She ignored him and stripped off her sundress to reveal a deep blue bikini that perfectly matched her eyes. Jack commented on this and Cindy blushed, smiling coyly at him.

“Thank you for noticing. I’m glad someone is willing to pay attention to me.” Her tone was thankful, remorseful, and resentful all at once. Jack was always amazed that women could pull stuff like that off.

“Well, it looks fantastic” and it really did to Jack. While not as skimpy as Debbie’s white one from yesterday it was certainly revealing enough that Jack’s mind wandered and wondered what Debbie had planned.

As if on cue he heard the doorbell chime. Excusing himself, he went to the door to find Debbie in the same sheer wrap from yesterday. She grinned up at him like the Cheshire cat. “Having fun yet?”

He grabbed her shoulders and pushed her to her knees. He pushed his suit down while wrapping his other hand in her hair. He fed her his soft cock, feeling it harden in her mouth under the attention of her tongue. He began to fuck her face and she gagged on his cock, spittle coating his balls. He stood her up abruptly, tucking himself away. Pulling the wrap away from her body he spanker her ass, once, hard, and made sure it was in a spot that clearly showed the imprint of his fingers.

“Your friends are waiting for you” he said, gesturing to the patio and handing her the wrap. She looked a mess. Her hair was tousled, and her lipstick smudged. Her smile, however, was radiant. She strode away, wearing a black bikini that was the twin of the white one from the day before.

He followed her, his bathing suit still tented but at least he wasn’t sticking up out of the top. He watched her undulating ass roll before him and could clearly see the marks from his fingers across the bottom of her lower right cheek. Max had figured out how to work the TV over the bar and was focused on a baseball game. Jack couldn’t believe how engrossed he was, as Max only turned around briefly when the women shrieked their delight at seeing one another.

“Bill got called down to Miami and will be there for a few days. I figured I’d crash the party that I wasn’t invited to earlier” Debbie said to Cindy. Max’s phone rang while she spoke and he answered, oblivious to the trio’s conversation.

“You’re welcome here anytime” Jack said. “Too bad about Bill. I was looking forward to seeing him again. He’s a very accommodating guy.”

Cindy was sitting back in a lounge chair and Debbie turned to face Jack as he spoke. Jack saw Cindy’s eyes widen as she saw the fingerprints on her friend’s ass. “Shipping out tonight, I’ve got to be in Tampa by 10” Max interrupted.

“Well, I guess it’s nice that we get to relax this afternoon before you have to go sweety” Cindy intoned. “This set up is simply divine Jack.”

“I’ll get the grill going so we can eat a bit early” Jack offered.

“No, no, let’s swim first” Debbie pleaded, grabbing Cindy’s hand. “Come on Max, let’s play chicken. Who do you want on your shoulders? You pick.”

Jack saw a flash of greed in Max’s eyes. “I want you” he said to Debbie and kicked his shoes off before walking to the pool. Jack realized the asshat was going to swim with his shirt on. What a piece of work.

“May I?” Jack asked, holding a hand out to Cindy. She blushed again, taking his hand and rising before they made their way to the pool’s edge.

“Cannonball!” Debbie’s cry caught Jack off guard and he turned just in time to see her hurtle through the air and land with an excellent splash that soaked both he and Cindy. Max was walking down the steps in the shallow end. Cindy pushed Jack while he was distracted and he tumbled into the cool water. He emerged in time to be drowned in the splash of Cindy’s own cannonball and when he finally emerged again it was to the pealing laughter of both women. A quick glance at Max showed his sullen mood had returned.

“All right Max. Get over here and let’s teach these two a lesson!” Debbie’s war cry did little to change Max’s expression, but he joined her nevertheless.

“Ready?” Jack asked Cindy, momentarily distracted by her deep cleavage.

“I think so” she said. He had been caught, red handed. Her shy smile told him that all was not lost though. Jack ducked under the water and felt her climb onto his shoulders. Her thighs were silky, womanly, and soft under his fingers. He stood and felt the thin triangle of fabric covering her sex press against his neck. His cock stiffened slightly under the water.

Max had managed to get Debbie up on his shoulders but was having trouble balancing with her weight. He moved to deeper water and then Jack charged. Cindy shrieked, grabbing his hair and face, crushing her breasts into his head. She released him as they reached the other pair and grabbed Debbie, pulling her forward. Debbie fought back, leaning backward but the sudden change of weight distribution was too much for Max and they went down.

“Again!” Debbie came up sputtering. Max looked like he didn’t want to play anymore but acquiesced. They were soon back up and grappling. Max did a better job this time and as the two girls grappled Cindy inadvertently (or maybe not) pulled Debbie’s bikini top, freeing those beautiful tits.

“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.

Her response was almost instantaneous. Her thighs clenched around his head and she moaned loudly, clenching her body forward so her tits rested on his head. He kept the pace and route of his tongue steady as the waves of pleasure crashed down on this previously neglected woman. As she came down from her climax her legs relaxed and he looked up expectantly at her.

“I never knew it could be like that” she gasped. “I truly suspected other people were exaggerating. I didn’t know if I’d ever be able to breathe again.”

Jack smiled at her, his face gleaming with her juices. “You deserve this. You deserve all of the pleasure you want. You have years of catching up to do.”

He looked at Debbie who was flush with her own arousal. “Would you like the ladies’ night special?”

“Yes please” she said in a sing-song voice and giggled.

“Coming up. But first I want a kiss.” Her face screwed up at his words. She could see Cindy’s juices covering his lips and was obviously a bit put off. His expression hardened and Jack knew that she understood that there would be consequences if she objected.

Jack rose to her level and they embraced. He made sure to rub as much of Cindy’s cum on Debbie’s lips as possible, making her taste her friend because he wanted her to. He felt Debbie’s nipples digging into his skin amidst the soft pillow-like flesh of her breasts. He broke their embrace, kissing his way down her neck, chest, stomach and finally through her lovely strip of hair before stopping at her nether lips.

He traced his tongue through her slippery folds and heard her forcefully exhaling, holding back the audible expression of her pleasure. He took the meaty outer lips into his mouth, sucking, pulling more blood into them before repeating the process on her inner lips. Her moans grew and her hand grabbed Jack’s hair, attempting to pull him up to her clit. He fought back, dipping his tongue into her vagina before replacing it with a finger and massaging that most sensitive of internal spots.

His tongue continued to trace her lips and his finger began to piston in and out of her. Sensing she was close, Jack attacked her clit, worrying the not-so-little nub in the same way Debbie had so recently treated his cock. It only took a minute of his before she exploded, mouth open in a silent scream as she coated Jack’s face and neck with her spray.

Debbie’s limbs were shaking as she lowered herself into the bubbling water. “Holy shit, I can’t believe you made me do that again.”

“Again?” Cindy immediately asked.

Mortified, Debbie looked from Cindy to Jack. “Busted! I suppose the cat’s out of the bag now” Jack noted with a rueful grin. “Might as well fill her in on all of the gory details.”

Cindy looked from Jack to her friend as Debbie recounted the details of the previous day. Jack was surprised that she didn’t leave much out. “All I’ve been able to think about is fucking his thick cock. I can’t get it out of my head. I knew your situation and thought that we could all benefit” she finished with an embarrassed shrug.

Cindy looked at her appraisingly. “Earlier at the pool! Your hair was a mess and you had a handprint on your ass! That was Jack?! Normally I’d be pissed that you lied and pushed me into this. But his tongue and fingers were magical.”

Debbie smiled broadly at her blonde friend. “I’m so glad you’re not mad. I really just wanted you to experience what our husbands can’t give us.”

“Aren’t you forgetting someone?” Jack piped up. “I think you deserve some punishment for deceiving your friend. Let’s get out of here though, I’m turning into a prune.”

Debbie looked worried at his words and twirled her hair nervously but the everyone got out and dried off, not bothering to dress before entering the house and proceeding to the master bedroom.

“You see Cindy” Jack began “while Debbie was remarkably accurate and candid in her account of yesterday’s events she neglected to tell you that she is my plaything now. Mine to use in any sexual way that I see fit. Isn’t that right my little slut?”

Debbie’s eyes were on the floor as she nodded. Jack stepped next to her and tweaked her nipple, hard. Debbie gasped and shut her eyes tightly. “She likes some pain and humiliation. Shall I demonstrate?” His hand slapped her tit, and she moaned, the red marks instantly appearing across her breast. “Bend over Debbie. Show your pretty friend those holes that I abused so thoroughly last night and this morning.”

Debbie turned her back to Cindy and half heartedly bent forward at the waist. “Do it” Jack warned and she bent a little further, spreading her feet apart slightly at the same time.

Jack reached and slapped her ass hard. Debbie yelped and bent forward, placing her hands around her ankles. “That’s better” Jack said as he rubbed her the tanned flesh of her ass. He traced a finger down her crack before roughly shoving three fingers into her slit. She moaned with the sudden invasion, bucking back against his hand. He sawed his fingers in and out several times before withdrawing them only to plunge two into her tight anal ring. She stiffened and cried out as he slapped her ass again with his free hand.

“Ever been with a woman Cindy?” Jack asked. She mutely shook her head no, eyes wide with a mix of awe and trepidation. “Neither has Debbie. Ever been curious what another woman feels like?” He had removed his hand from Debbie’s ass and walked around so that Debbie’s head was just below his crotch. He extended his recently used fingers down, placing them into Debbie’s mouth. She dutifully sucked them clean before he withdrew them.

“I think you should spank her” he said to Cindy. “I would say it would serve her right, but the little slut loves it. Try it.” As Cindy weighed her options he grabbed Debbie’s hair, wrapping it into his fingers. He pulled her hair back, forcing her face up and he rubbed his partially erect cock all over her face.

He looked up in surprise when he heard the first pop of flesh meeting flesh. Cindy had landed a blow on Debbie’s upturned backside but Jack thought it needed a bit more power behind it. “Harder” he said. “This is about teaching her a lesson. Don’t hold back.”

He watched as Cindy’s hand raised and flew forward, eliciting a satisfying smack on the brunette’s exposed ass. He had pushed Debbie’s face into his balls now where she half shrieked/half moaned with each blow the blonde landed on her.

Cindy’s tits swung fabulously with her efforts. Her nipples were hard and she had the fire of lust in her eyes. “Feel her ass now Cindy” Jack requested. “Feel the heat.” He watched as her hands lightly caressed her friend’s burning flesh. “See how wet she is, how much she enjoyed what you just did.”

He watched as she hesitated before sliding her hand down between Debbie’s legs. Jack couldn’t see her hand but watched as Cindy’s eyes opened wide as she apparently found out how wet Debbie was.

Jack pulled Debbie off of his balls and shoved his dick into her mouth. “Get me hard. Make me hard to fuck your friend.” Debbie moaned loudly at this and enthusiastically worked her lips and tongue around his shaft and he felt himself grow in her mouth. “Fluff me for her. Suck my cock you married slut.”

Cindy’s eyes shot to him but he grinned and winked. “It’s your turn next Cindy. She’s going to be our little fluffer slut. Why don’t you go get comfortable on the bed?”

Cindy turned without a word and climbed onto the bed, spreading her legs so that her hairless pussy was in plain view. Jack pulled Debbie up to standing and moved her onto the bed between Cindy’s splayed legs. “Warm her up for me. Taste her juices directly from the source, the same juices you tasted on my face earlier.”

Debbie leaned down cautiously, extending her tongue as she did so. Jack reached under and tweaked her nipple hard with his left hand causing Debbie to gasp and lurch forward, colliding with Cindy’s bare snatch. With his right hand he reached behind Debbie and slowly started fingering her wet pussy, again reaching for her most sensitive spot.

Both women were moaning now. “Isn’t her tongue nice Cindy?” Jack asked.

“Holy shit that feels good” Cindy moaned.

“Maybe she’ll be your cumslut too” Jack suggested, and Debbie moaned into her friend’s cunt. “Would you return the favor to Debbie? After all, that’s just basic good manners.”

Cindy moaned loudly, beginning to writhe against the sheets. “Yes, yes, god yes. Anything, just don’t let her stop!” Her words suddenly stopped though her mouth continued to move, forming soundless words and she gripped the sheets tightly as an orgasm rolled through her.

Debbie rocked back, dislodging Jack’s hand as Cindy relaxed her grip. “That was actually really hot. Holy shit. Who knew?” she asked rhetorically with a grin.

“Agreed” said Cindy. “This is the best sex of my life already and I’ve only licked the tip of his cock so far.”

“So far is right” said Jack. “Debbie, I want you to put my cock in Cindy’s pussy.”

Obediently she shuffled across Cindy’s leg, her breasts swinging delightfully. Jack moved to take her place and lined himself up with Cindy’s vertical slit. Debbie’s slim fingers closed around his shaft, stroking him a few times before she leaned down and briefly sucked him.

“Are you ready Cindy?” she asked. “This will be like nothing else you’ve ever experienced.”

Cindy nodded, looking down at Jack’s angry erection. Debbie pulled him forward and traced his mushroom head through Cindy’s wet red folds, lubing him. She angled his cock down and Jack thought that Cindy was as tight as any woman he had ever been with as he watched her small lips part to accept his member.

“Wait” Cindy gasped. “Slowly. God you’re huge.”

Jack thought her frame of reference was skewed, but it gave his male ego a boost anyway. He rocked back and forth, sinking a little deeper into her tight snatch each time. The soft pads of Debbie’s fingers were massaging Cindy’s clit while Cindy screwed her eyes tightly shut and thrashed her head back and forth with each deeper thrust.

It took several minutes, but Jack was finally fully sheathed in Cindy’s tight married cunt. He paused, allowing her to adjust to his intrusion as Debbie’s fingers continued their dance. “Suck my tits Debbie. Suck my nipples you filthy cheating cumslut” Cindy’s direction sent a thrill through Jack, and he felt his cock spasm inside of her.

Debbie, for her part, didn’t bat an eye but began teasing, licking, and biting Cindy’s light pink nipples and creamy breasts. Jack began to fuck Cindy in earnest, pulling almost all of the way out, loving the way her lips clung to his thick shaft before plunging forward again and causing her tits to bounce delightfully. He kept up a steady pace as he felt Cindy begin to clench on his cock.

Cindy clenched forward as she came, pulling Debbie’s head onto her breast hard as she moaned loudly. Jack slowed as she came down and eventually withdrew. Cindy looked like a starfish on the bed, sweaty blonde hair plastered against the nape of her flushed neck, her chest heaving.

“Clean me up” Jack told Debbie. “Suck your friend’s cum off my cock.” He pointed it at Debbie and pulled her head towards him. Her mouth opened and he pushed his way to the back of her throat with one fluid motion. “Do you like the way she tastes?”

Debbie moaned in response. “That’s my good little slut. Since you’ve done so well tonight I’ll allow you to request which of your fuck holes I use now. Where do you want it?” Jack was addressing Debbie but saw Cindy’s eye’s go wide at his words.

“My pussy. Please fuck my pussy” Debbie gasped.

Jack was happy to oblige and positioned her on all fours next to Cindy. He stepped up behind her and slowly traced his stiff pole around her nether lips before sliding it in. Within a few strokes he was fully seated and began to fuck Debbie in earnest as Cindy watched. “She loves to have her tits pinched and twisted. You should try it.” Given everything that had happened so far Jack supposed it was no surprise that Cindy readily acquiesced and with each tweak Jack could feel Debbie’s hot cunt contract on his pistoning rod.

“Cindy” Jack said and beckoned her over. He withdrew his cock and Debbie moaned her disappointment: she had been so close to finishing. He pulled Cindy close: “Will you suck your friend’s juices off my cock as a thank you to us? If it hadn’t been for her we wouldn’t be here now.”

Cindy hesitated, but then dipped her head and Jack felt her tongue trace a path up from the bottom of his shaft to the top. Her mouth plunged over the mushroom head of his cock and Jack moaned at the sensation. “She’s tasting your juices Debbie.” Both women moaned at this announcement and Jack was sure that he was coating Cindy’s mouth with precum.

Jack pulled back, and his cock fell away from Cindy’s mouth with a few strings of her saliva coating it. “Up on the bed next to Debbie” Jack said; he had always wanted to try this.

He positioned himself behind Debbie and eased himself into her, grasping the tanned globes of her ass as she moaned. “Do you like that I’m using Cindy’s spit as lube to fuck your slutty pussy Debbie? I’m going to use your juices to fuck her in a moment.”

Debbie moaned loudly with the mental image as Jack pulled out of her and stepped behind Cindy. The contrast between her large pale ass and his tanned hands was striking and he grabbed the flesh of her cheeks hard. “Do you like the thought of Debbie’s juices sliding into you now?” Cindy moaned in response to his question before uttering a hissed “Yessss.”

“It’s Cindy’s juices, Cindy’s cum that I’m pushing into you now” Jack said as he switched back to the brunette. “Your sissy husband could never hope to satisfy one woman and I’ve already made you both cum tonight. Cum for me now Debbie, cum all over my fat cock covered in your friend’s cum and I’ll let you taste my cum from her messy cunt.”

It wasn’t long before Debbie’s body froze, her orgasm paralyzing everything but her vocal cords. Her moan was long, guttural and animalistic in its intensity. She fell forward onto the bed, limbs akimbo.

Jack moved behind Cindy and thrust into the blonde hard. His release was what was needed now. He fucked her hard, her ass jiggling with the pounding of his hips, her breasts swinging dangerously. Her head fell forward as his intensity increased, his groans punctuated by yelps from her pretty mouth.

He felt his orgasm build and called to Debbie: “I’m going dump my load in your friend’s married pussy. The load that you wanted for your own, the one that you’ll have to claim with your tongue from between her thighs.”

With that he exploded, roaring through an orgasm that left him seeing stars. His hips bucked again and again as his balls contracted, emptying their contents deep into Cindy’s womb.

He fell back, rising to stand. His deflating cock was covered with gobs of his sticky cum mixed with Cindy’s own. Cindy lowered herself to the bed, rolling onto her back causing her large tits to spill to either side of her chest. Her vagina was an angry thing: red, swollen lips sticky with their combined juices.

Jack and Debbie moved to opposite ends of the busty blonde. Debbie lowering her head to the nexus of her creamy thighs while Jack knelt next to her head.

“Taste it. Taste me, taste us.” He offered her his cock and as she opened her mouth he massaged her massive breasts, rolling the thick nipples between his fingers. He watched as her tongue searched out his cum and she swallowed it, while she moaned from Debbie’s ministrations.

He collapsed onto the bed next to Cindy and Debbie joined them on Jack’s other side once her task was complete. The trio drifted off to sleep, exhausted from the mentally and physically taxing activities of the evening.

Source: reddit.com/r/Erotica/comments/8fs85h/new_jack_3_4