Pleasures in Paradise
Group Sex Story

Pleasures in Paradise

by Alexanderx 17 min read 4.5 (6,300 views)
group sex novel sailing orgasms blow jobs big coc younger woman older man
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The next morning Michael met Kaylee down at the lobby at 7:10 am. She was clad in a grey sweatshirt, the sleeves pulled halfway up her arms, a pair of baggy white shorts that went about halfway down her thighs, and a pair of white sneakers on her sexy little feet. Her sandy blond hair was swept over her head, covering her left ear, and pulled back behind her right on the other side in her usual style. The valet brought Michael's rental to the front entrance, and after generously tipping him they both got in and were off on their adventure.

It was a forty minute drive to the marina. Along the way they stopped at a fruit stand that also sold coffee. Grabbing two cups of Kona brew, they also purchased a couple of loaves of banana bread to bring as a gift for their hosts, then got back on the road. A half hour later they were at the marina. After parking, Michael and Kaylee walked down to the slips. Dwight had explained very clearly where they could locate the boat, and after they got their bearings they spotted it. Cheryll was on the dock by one of the mooring ropes. Looking up she saw them and waved. They returned the gesture, strolling in her direction.

"Good morning guys!" she said warmly.

The smashing brunette wore a pair of dark blue cutoff jean shorts, the pocket liners poking out slightly onto her tanned, trim thighs. She was barefoot, and Michael couldn't help but gaze down her legs, a caramel brown from top to bottom, her toenails painted with bright red polish.

A loose fitting blue t-shirt hid her torso, but it didn't quite make it all the way to her shorts, and when she straightened up they were treated to a glimpse of her rippling, brown belly, a tiny bejeweled ring protruding from her navel. A grey, worn-out baseball cap protected her head, dark hair poking out from behind, pulled into a loose ponytail.

"Welcome aboard! I've got muffins and coffee prepared.

D

is just working on some stuff out on the bow, he'll join us in a few minutes."

Michael glanced up to the front of the catamaran, spotting Dwight bent over dealing with something. He was partially obscured, making it difficult to discern exactly what he was doing. They stepped on board, following Cheryll inside, her tight little ass sashaying in front of them. The interior of the boat was quite spacious, at least it seemed that way to Michael. She escorted them into the dining area adjacent to the galley, the three sitting around a small table.

"I know you said to just bring ourselves, but we came bearing gifts," Kaylee said, passing the banana bread to Cheryll.

"Oh wow, awesome! Thank you so much. They'll go great with the muffins. You guys should flip off your shoes, you'll be more comfortable walking around barefoot."

They followed her advice, placing their shoes in a little cubby. Cheryll placed a basket of freshly baked muffins and the banana bread on the table, joining Michael and Kaylee. He poured them each a cup of coffee from a large carafe. The coffee was strong but good, and the pastries were out of this world, warm and delicious. They chatted for a while until Dwight popped into the cabin.

"Hey there you two," he said jovially. "Didn't know you were on board."

"We thought we'd sneak in and surprise you," Kaylee replied, grinning in that captivating way she had.

"Well, mission accomplished. We'll be underway soon, just a few more small jobs to do. After you're done your snack come up on deck, I'll get you guys to help me, maybe teach you a little about sailing."

A short while later they followed him, completing several little tasks that he instructed them in. It was enjoyable, Dwight an excellent host-slash-teacher, calmly explaining what he needed them to do, joking here and there, putting them completely at ease. In no time they were motoring out of the marina, and when clear they helped him hoist the sails.

It was another fabulous Kauai day. Often in the mornings it could be overcast, and even rainy, but today the sun was already shining brightly, mostly clear skies overhead, the odd small cumulus cloud dotting the canvas of blue above them. It was a bit windy, which Dwight explained was ideal for sailing, but it did make the trip exciting, swells causing the boat to rise and fall a bit more than Michael had anticipated.

The journey took about an hour. Along the way a pod of friendly dolphins joined them. Michael had his camera, recording several minutes of video before they lost contact when the playful mammals veered off in another direction. Kaylee was excited beyond belief, having never seen dolphins in the wild before.

"Oh my god Dwight, that was absolutely incredible!"

"Yes, wasn't it? Oh, and call me

D

, that's what Cheryll calls me, and a lot of my friends as well."

"OK

D

, you've got it," she said, smiling as she casually ran her hand down his arm.

"So Dwight, Do you spot a lot of wildlife sailing around the islands?" Michael asked, determined to not use the sobriquet suggested to Kaylee.

"Oh yeah, usually dolphins, and frequently whales, especially humpbacks."

"Really? We might see humpback whales?" Kaylee asked breathlessly.

Dwight chuckled.

"Sweetheart, we're just a bit outside their season, so probably not."

"Oh darn," she said, affecting an exaggerated pout.

"You'll just have to come back and visit us another time."

"Well, I might just do that

D

."

Everything about their little voyage was entertaining to Kaylee. She pranced around on deck, her bare feet slapping against the surface of the synthetic flooring. During the initial stage of the trip it was still a touch cool, so she kept her shorts and sweatshirt on, but later when things warmed up she stripped down to her little yellow bikini. She asked Dwight to show her how to steer the boat, and he was more than willing to be her tutor.

She took the wheel and at first he stood behind her, giving directions, his right hand resting casually on Kaylee's right hip, but after a while he moved closer to her, his strong arms encircling her. He placed his hands on hers, ostensibly to instruct her, but in reality much more. Kaylee appeared completely focused on what she was doing, seemingly unaware that Dwight was now pressing his groin into her ass as he continued to "teach" her. Cheryll and Michael were sitting nearby, observing the show.

"

D

's always been a people person," Cheryll said, grinning at Michael, aware of his discomfort watching her husband so blatantly press his body into Kaylee's.

"Is that what you call it?" Michael said cynically.

"Hey, my husband's just a very hands-on guy."

"Evidently. And it doesn't bother you?"

"No, of course not. Come on, I'll give you a tour of the boat."

She took him by the hand, leading him back inside. The cat was a fairly large one, as Michael quickly learned moving from section to section. There were three sleeping quarters, two guest cabins and a master cabin, which was the last stop on their tour. It was incredibly roomy, much larger than he would have thought possible, a queen sized bed occupying most of the space, but still allowing some room to move around.

"So, this of course is where

D

and I sleep," Cheryll said airily, sweeping her hand in front of her.

"Wow, this is quite the bedroom, so spacious."

"Yes, it really is wonderful."

Cheryll looked into Michael's eyes then moved towards him, her body sliding into his, her arms wrapping around him. Five feet five inches tall, she lifted herself up onto her toes, pulling his face to hers, kissing him, her tongue slipping into his mouth. She was a fabulous kisser, her supple lips caressing his, but Michael was so surprised by her sudden brazenness that he pulled away almost immediately.

"Shit Cheryll, Dwight's just above us," he said under his breath.

"It's fine Michael, Dwight's cool," she replied, moving to kiss him again.

"No, I'm not sure this is right."

Michael began to question himself. He had fantasized about this very scenario, and now suddenly he had become Mr. Puritanical? The guy who had fucked a flight attendant his first night on Kauai, the guy who was currently fucking a twenty-one year old hot little slut and her equally slutty forty-one year old mom had out of nowhere grown a moral compass?

Cheryll smiled coyly.

"Listen Michael,

D

and I have...well I guess you'd call it an understanding. Our marriage is an open one, and we invited you and Kaylee today hoping to have some fun, but if you're uncomfortable..."

Clutching her arms Michael hauled her body into his and kissed her, their tongues tangling together. His hands dropped behind her, squeezing her firm, curvaceous ass, pressing his crotch into her.

Fuck morals,

he thought. After several seconds she drew back, a salacious look in her eyes.

"Well, well, well, glad to see you're into it after all."

He moved to kiss her again, but now it was her turn to resist, putting her hand against his chest and gently pushing him back, her large brown eyes twinkling.

"Not now. We'll all have some fun in a little while," she said softly.

She led Michael back up on deck. Dwight was now guiding the boat himself, Kaylee having moved up to the trampoline mesh situated at the bow, reclining on a towel, basking in the sunshine. Dwight's plan was to bring them to a small cove that was sheltered from the swells, and shortly after Cheryll and Michael were back up top the vessel reached their destination. Together they helped lower the sails and drop anchor, sitting out on deck and having a beer when the job was done. Dwight was the only one not imbibing, being responsible for the safety of his craft, and taking that very seriously.

"So, we figured on maybe doing some swimming, or snorkeling, then take the dingy to that little beach on shore for a picnic lunch, then come back to the boat and relax for a while. What do you guys think?" Cheryll said, moving her beer to her lips when she was finished speaking.

"That sounds wonderful!" Kaylee replied, her face beaming.

Having already gotten down to her two-piece swimsuit, it was now Cheryll's turn to join her. Shedding her jean shorts, her tiny red bikini bottom came into view, sitting low on her hips. Michael was hoping for a thong, but was quite pleased with what he saw, the covering fitting her so perfectly, her round cheeks wonderfully filling the material. The abdominal muscles of her bronze stomach rippled slightly, the tiny belly button ring glimmering in the sunshine.

Removing her hat she then proceeded to peel off her t-shirt, revealing a red bikini top and the treasure tucked away beneath. To say that her breasts were magnificent would be more than an understatement. Two large, very tanned melons struggled to break free of the confining garment, showing plenty of side and under boob. Her nipples strained against the silky triangles of the top, two prominent nuggets popping out appealingly. Michael couldn't help but gaze fixedly at the display. Kaylee was awestruck as well, and catching his eye she simply mouthed "wow." Dwight, cognizant of the reaction, just chuckled.

"They're worth every penny, believe me," he said.

"Oh shit, sorry, I didn't mean to stare."

"Don't worry Michael, I'll take it as a compliment," Cheryll added, winking at him.

She untied the scrunchie holding her ponytail in place, shaking her black hair free, the shining curls loosely resting below her shoulders. Her large brown eyes peered into his, and he couldn't help but get half hard looking at her amazing, suntanned form clad in that skimpy little red bikini. Walking over to him her hand grazed his arm, then she continued on by, heading over to the rail a foot or so above the deck.

"Well, I don't know about the rest of you, but I'm going for a swim," she said, gracefully diving overboard, her body effortlessly entering the water.

Kaylee popped to her feet, running across the deck a little recklessly perhaps, then jumped into the air, pulling her knees into her chest as she catapulted over the side.

"Cannonball!" she bellowed, a fair sized splash shooting above the surface as she plunged into the sea.

Under the water for a few seconds she re-emerged, her golden tresses pasted to her head and across her face. She was laughing and hooting, having a grand time, swimming out a ways from the boat and then back in again.

"Well buddy, we should join them," Dwight said, pulling his t-shirt over his head and diving overboard.

When in Rome,

Michael reckoned, jumping into the clear ocean waves as well.

They spent forty minutes or so swimming and snorkeling. Dwight and Cheryll had all the gear they would need, and there was a nice outcropping of coral not too far from where the boat was anchored, less than a five minute swim. The four of them headed over that way, Dwight towing a couple of floatation devices behind him in case anyone needed a break.

An incredible array of tropical fish species greeted them, each type seemingly trying to outshine the others, their vivid colors dazzling. They were also lucky to briefly spy an octopus squeezing between some rocks below them, but the real highlight of the morning was a green sea turtle, Kaylee practically losing her mind when Dwight pointed it out to her.

She followed it for several minutes, not getting too close, out of respect for the creature as well as Hawaiian law. She was over the moon, and went ballistic when the turtle actually turned and approached her, cruising to within a foot then just floating nearby, almost as if it was checking her out.

When the excursion concluded everyone climbed back onboard. After drying off in the bright sunshine, Cheryll and Kaylee went into the galley to prepare the picnic, Michael helping Dwight with the dingy. They had everything loaded up and were heading to shore a half hour later. As they landed on the beach Dwight hopped into the surf, dragging the small craft ashore, securing an attached rope to a large boulder. They unpacked everything and hiked further up the beach, away from the lapping waves.

Lunch was fantastic, a combination of salads, seafood, sandwiches, fruit, and a sensational bottle of wine. They dined and drank, chatting about their adventures. Dwight and Cheryll had some interesting sailing stories and tales about some of the places they had visited. Apparently their life together was nothing if not exciting and unique.

"We're so lucky to have met you two," Kaylee said. "What a fantastic day this has turned out to be."

"Oh that's so sweet, but we feel just as lucky to have met you guys," Cheryll replied. "Right

D

?"

"Most certainly," he answered, looking directly at Kaylee.

"You know, it's funny, but you two kind of remind me of us," Cheryll added.

"How so?"

"Well, you and Michael just seem to fit so well together. You're a bit of a free spirit it seems, and he's a tad more serious I think. Just like

D

and me. And then there's the age difference."

"Huh, really?" Michael interjected, joining the conversation. "Just how much of a difference do you think?"

"Hmm...I'd say around thirty years. Kaylee's maybe twenty-two, and I'd guess you're about fifty."

Michael winced, somewhat miffed that Cheryll had pegged him at five years older than he was, but on the other hand figuring that age didn't matter that much to her so she was probably oblivious to it. Kaylee snickered when she heard her say that she thought Michael was fifty, then further probed the other couple's situation.

"Close. Now how about you two? How old are you guys?"

"Well, I'm thirty-six, but I want you to guess

D

's age."

"Ooh, a guessing game, fun!"

"Come on Cheryll, don't embarrass me," Dwight scowled, but sounding like he didn't really mind.

"Don't worry

D

, I'll be kind," Kaylee purred sexily.

"So, what do you think?" Cheryll asked.

"Well...he's in great shape, big and strapping, and still quite active, but I'm thinking he's a bit older than Michael, so I'm gonna say late fifties."

"Ha, not even close!" Cheryll said, laughing as she did so.

"Not close? Okay, how about sixty-five?"

"Nope."

"Younger?"

"No."

"You're fucking shitting me, right?"

Kaylee was incredulous, and so was Michael. He could tell by looking at Dwight's face and his eyes in particular that he was older, but he didn't figure he was much more than sixty. If he was north of sixty-five then he was holding up amazingly well. Kaylee took another guess.

"Sixty-seven?"

Cheryll shook her head.

"Sixty-nine?" Kaylee said suggestively, winking at Dwight, Cheryll again replying in the negative.

"No fucking way! You're in your seventies?" Kaylee said, looking at Dwight with an odd mixture of wonder, shock, and desire.

"Turned seventy a month ago," Dwight said, grinning.

He wasn't self conscious in the least, if anything he seemed proud. Michael supposed it was something to hang your hat on, but he still couldn't fathom that this guy was for all intents and purposes a senior citizen, an old geezer. As for her part, Kaylee was intrigued by the revelation. Michael could see by the look in her eye that she would fuck him if she was given the opportunity, and based on what Cheryll had said, that appeared to be a likely outcome.

Of course Michael realized that there was the titillating prospect of him fucking Dwight's gorgeous wife. Cheryll was a stone cold knockout, the kind of woman old enough to know all the tricks, yet still young enough to make the most of it. Michael began to speculate on their sex life. They were obviously into the swinger lifestyle. Did they watch each other, participate in three-ways, or even full on orgies? He would leap at the chance to be with her and Kaylee at the same time, but a nagging voice in the back of his mind still questioned if he really could go that far.

I guess I'll just have to see how things play out

, he thought.

After finishing lunch they spent some more time on the beach, swimming and just lounging on the sand. An hour later they were on their way back to the cat. Climbing back on board the sailboat, Kaylee and Cheryll went inside to tidy up and put away the leftovers. Michael helped Dwight secure the dingy, then had a beer while Dwight went for a nap on the trampoline. Afterwards Michael was feeling a bit drowsy himself and ended up snoozing on a sofa in the cockpit.

The sound of the ladies' muffled voices woke him from his slumber a short while later. Getting to his feet he undertook to discover the source, the faint but unmistakable lilt of Kaylee's giggling, followed by some whispering, then some more giggling compelling him forward.

He entered the upper cabin, then moved down the companionway to the deck below, more than curious about what was going on. The giggling had stopped, replaced by the equally distinctive noise of two people kissing. He traced the siren call to the master cabin, lured by the mental image of Kaylee and Cheryll making out.

What Michael observed as he passed through the open doorway took his breath away. The air carried the faint aroma of recently smoked weed. Kaylee and Cheryll were both naked, lying on the bed, their lower limbs twisted around each other, Kaylee's right hand cupping Cheryll's ass. He caught his first glimpse of the brunette's pussy, shaved clean save for a thin dark landing strip. They were in middle of a hot kiss. He stood there for a few seconds just watching, before coughing lightly to announce his presence, Kaylee and Cheryll both looking over.

"Oh, there you are," Kaylee said. "I was hoping you'd be joining us."

"Why don't you strip and climb in here," Cheryll added.

"Don't mind if I do," Michael said, dropping his shorts and tearing off his t-shirt.

"Wow, you are good to go, I'm impressed," Cheryll commented, eyeing his erection.

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