The Twins' Vacation Ch. 01

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Jackie and Jake visit an island resort.
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Part 1 of the 7 part series

Updated 06/08/2023
Created 09/20/2017
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"We need a vacation!"

Jake looked over at his twin sister as she propped herself up on one elbow and rested her chin in the palm of her hand. The erect nipple on her right tit brushed against his arm.

"Do we really need to talk about that...right...this...minute?" Jake gasped in exasperation and squirmed around a little.

"It's as good a time as any," Jackie giggled and twirled some of his thin chest hair in her fingers, "unless you've got something better to do."

"You're fucking impossible!" he practically screamed as his entire body tensed and his back arched.

"You want some of this?" their friend Dori asked with a big grin, pulling Jake's hard cock from her mouth to brush against her chin as his cum started to spurt, all the while keeping two fingers buried deep in his ass.

Jackie leaned over Jake to scoop some of his spent semen from Dori's face with her tongue before the two girls began an extended tongue lashing kiss, one intense enough that Jake's dick stiffened sufficiently for Jackie to climb up on her brother. She slowly impaled herself on his cock. By the time his cum shot into his twin's dripping pussy, both she and Dori had already climaxed once again.

*********

Jackie and Jake were twins, identical in practically every way except their sex. Jackie was older than him by eleven minutes. Purely by happenstance, they were born in different years, she at 11:54 PM on New Year's Eve and he at 12:05 AM on New Years Day just over twenty years before. She never let him forget it.

Dori was a few months younger than them and had been their companion since preschool. She was as tall as Jake but skinny as a rail, with practically no ass and tits little more than dark brown bumps for her pierced nipples. Recently she was going through a Goth phase with short spiky pink and purple hair on her head that matched the tangled bush between her legs. Both Jackie and Jake loved the feel of the silver ball embedded in her tongue.

A little over a year before, a couple of weeks after the three of them graduated from high school, Jackie and Jake's parents decided to spend some extra time visiting their own parents. The twins remained behind since they had just started summer jobs before enrolling in the fall semester at the university.

That day, Jake walked in the door to their house after work to find Jackie crying uncontrollably. He sat next to her and pulled her close, not even sure why she was so upset. After a few moments, she looked up at her brother and lover with tears streaming down her face.

"Th...the sheriff...Mom...Dad...they...crashed...died...," Jackie sobbed.

Their parents missed a sharp turn on a back country road at too high a speed on the way to their grandparents' ranch, crashing over a steep embankment and into a large tree, dying instantly. Poppy, their grandfather, never told them the coroner found their father's dick in their mother's mouth, fifteen feet from his mangled body.

The next few months were rough, but Jackie and Jake ultimately decided to stay in their city house and for their university classes. Dori moved in with them and ever so slowly life went on and back to normal...as normal as can be expected for a brother and sister living together as lovers with their female partner.

"We could always go up to the ranch," Dori suggested with a wicked grin as the last bit of Jake's semen dripped from her chin..

The ranch was a five hundred acre place nestled into the high desert and low foothills about three hours drive north of the city. The property was surrounded on three sides by federal forest lands and stretched itself from one border of the public lands to the other.

Their grandparents, Nana and Poppy, bought the land some forty years earlier with part of the proceeds from an initial investment in a little unknown tech start-up that exploded in value after only a year or so. Shrewd investments thereafter assured them of a steady and very comfortable income.

With no need to work regular jobs, they bought the place as a way to escape the hubbub of city life, almost totally off the grid. Even more importantly, it was a place to every day...and in every possible way...live the sexually anarchistic lifestyle they desired. The small cluster of buildings grew over the years as more people joined them, supplemented by the addition of solar power and a satellite dish so they could stay apprised of what was going on in the rest of the world.

Nana and Poppy only had two rules: everyone contributed to the best of their ability and no means no.

Neither Jake or Jackie could ever remember hearing a "no" in regards to any sexual advance or act by anyone and had never uttered the word in that regard themselves...to anyone...at anytime...about anything...ever. Neither had Dori.

"Sure, you always want to go up there so you can just get yourself fucked silly...again," Jake laughed.

"Of course, so we all could," she retorted and playfully punched his shoulder.

"No, I mean a real vacation, someplace exotic where we've never been before," Jackie interjected with a wicked grin, "and someplace where we are not necessarily the wildest people there."

After a few weeks of research, they finally settled on an exclusive, all inclusive, adults only tropical resort on a small Caribbean island.

**********

"I feel like shit," Dori muttered, tentatively sipping a hot coffee.

"Well, that seems fitting, since you look like shit," Jake giggled then moaned before gulping down some of his own coffee.

"Keep your voices down," Jackie groaned, "You're both killing me here."

"I had no idea the clubs in South Beach apparently don't close if it is still dark outside," Dori continued in at most a hoarse whisper, "or that Cubans partied that hard."

"Yeah, what's his name...Jorge...Jose...whatever...sure did have a nice cock and knew how to use it," Jackie chimed in dreamily, "and his wife's pussy was really sweet too."

The three of them flew to Miami a day before they were booked for the Caribbean resort. Naturally, they wanted to try some of the hot spots in South Beach and ended up getting very drunk and taking a Cuban couple back to their hotel.

The man was more than willing to fuck them all and the woman enjoyed pussy as much as cock. They finally left barely an hour before the twins and Dori needed to get to the airport for their first flight of the day.

The background thrumming of the jet engines in flight didn't do much to alleviate their headaches. Then they sat waiting for the inter island transfer flight taking them to their destination, a wait that now extended to three hours past the scheduled departure.

Figuring it couldn't get any worse, they switched to local beers watching a steady line of jets large and small take off and land. Finally, they boarded a small nine seat prop plane taking them the short distance to their final destination.

The ninth seat was next to the pilot and Jake eagerly claimed it. With everyone settled in, they taxied out to the middle of the runway and the pilot radioed the tower.

"Flight 5463, requesting permission to take off," the black pilot intoned with a clipped British accent that Jake knew made his sister's nipples stiffen and her pussy clench and drip.

They waited for a minute or so with no response.

"Flight 5463, requesting permission to take off," the pilot repeated.

Again, there was no response.

He fiddled with the radio and, after another minute, again requested permission to take off.

There was only silence.

Jake started frantically looking out the window as far back as he could see, remembering all those large jets they watched land while drinking beer all afternoon. Behind him, his sister and Dori were asking what was going on when the pilot made a final announcement.

"This is Flight 5463. I PRESUME I have permission to take off!"

With that, the pilot gunned the engines and the small plane shot down the runway. Until they were safely in the air, Jake fully expected one of the large jets to just squash them on the tarmac. More interestingly, his dick was rock hard.

**********

The remainder of the short flight was uneventful. Upon landing they grabbed their bags from the back of the plane and trudged into the open air terminal. A couple that could have been their parents' age walked ahead of them until they spied a stout mid fifties looking man with a pony tail, scraggly beard and very loud red and yellow and green shirt standing near the exit.

"Jackson!" the older woman screamed in delight, rushed to the man and threw herself into his arms while giving him a deep tongue lashing kiss.

In turn, he grabbed her ass cheeks in both his hands and pulled her off her feet to him. The woman's companion walked up to them smiling broadly and shook Jackson's hand when they broke off the kiss.

Next to them, a young woman wearing a halter top and very trim tight shorts held up a sign with the name of the hotel. She and Jackson were apparently there to transport them to the resort. With introductions all around, they headed for a rather beat up minivan for the trek to the hotel.

The woman's name was Ginny and her companion was Ed. The young woman was introduced as Jackson's eighteen year old daughter, Leah. With all the luggage, it was a tight fit in the van. Jake and Jackie climbed in the rear seat with Dori and Ginny.

Ed took the front passenger seat and Leah eagerly got on his lap. By the time they left the terminal grounds, it was already getting dark and Leah and Ed were openly kissing and groping each other.

Jackson explained it was a forty minute drive. Although the kitchen would be closed by the time they arrived, he had arranged for a small buffet and drinks. There was also a cooler of beer behind the driver's seat. Ginny happily passed them around, casually brushing her tits over Jake's chest as she handed one to Jackie and Dori.

"You pay attention to where we're going, Jackson." Ginny laughed playfully and leaned forward to kiss the back of his neck. "Your driving and this old van haven't gotten any better over the years navigating what are laughingly called roads around here. I'll bring our new friends up to speed on your wonderful place."

Jackson just let out a loud guffaw that Ginny took as the permission she needed. In the front passenger seat, Ed had Leah's halter top completely off and was sucking her very tanned taut tits as he rubbed her pussy through her shorts.

Ginny took a deep drink of her beer, flicked her eyes toward Ed and Leah then smiled impishly.

"Don't mind them," she murmured, "Leah's been riding on my brother's lap like that and lots of other ways since she was a very little girl."

"You've been coming here for a while?" Jackie asked leaning back with her own legs splayed wide apart.

"Since back when Jackson could still see his cock when he looked down over his belly without a mirror and my tits were still beating gravity," Ginny laughed, letting one hand fall on Jake's thigh as they made a sharp turn and left it there once the van straightened out again.

"You didn't even have tits the first time your folks brought you here!" Jackson laughed again.

There was no doubt Ginny's eyes were locked on Jackie's crotch. Jackie grinned and put her hand on Jake's other thigh, slowing moving it up toward the obviously growing bulge in his shorts. Then Jackie started fondling the inside of her own thigh with her other hand.

Jake leaned back and sipped his beer, wondering if his twin sister could goad the older woman into feeling his stiffening cock. Ginny just grinned and matched Jackie's movements until their hands met at his dick. After a moment, Ginny gave him a hard squeeze and removed her hand.

"So, this is your first time to Jackson's little slice of paradise?" she asked.

"Yes, it is," Jake gasped with his sister's hand still firmly planted on his dick, "from everything we read about it, this is just our sort of place."

"That's interesting to hear since we can hardly publish all of our very unique and special features," Jackson exclaimed from the front seat as the van continued careening down the winding roads.

Ginny giggled again and ruffled the back of his head.

"Just drive and I'll give them some details," she said, "and I'm looking forward to some of your own unique and special features later...as always."

Jake looked over at the passenger seat. Ed had Leah's shorts unzipped and his hand buried down between her legs as she continued kissing him passionately. She looked up, smiled at Jake, winked and rammed her tongue back in Ed's mouth.

"The resort has a total of twenty four casitas, arranged in groups of four along he beach on one side of the main building, each group with a small pool. There's no need for air conditioning here, not with the constant ocean breezes. If the doors and windows are closed, the occupants want privacy. If the window shutters are open, you are welcome to look in but not enter. If the door is also open, you are invited to come in."

"And we have never closed a door in all the years we've been coming here, have we sis?" Ed chimed in as Leah began to moan lowly.

"If you ever stayed long enough, I'd just have the damn things taken off!" Jackson laughed heartily.

"Well perhaps when we both retire, until then I suppose a few guests might close them once in a while," Ginny grinned and casually ran her hand over Jackie's hand and Jake's hard cock. "So how many folks are here now anyway and anyone we may know?"

"With the five of you, twenty seven and the family of course," Jackson answered after a moment. "Eight Americans, four each Germans and Canadians and two each from England, France and Australia. The relationships are pretty much the regular mix of siblings and parents and grandparents. If I recall, you and Ed ran into Peter and Melanie, from Australia, a few trips back. I'm not sure about the others but if I know you, you will know everyone well enough before your visit is over. "

"Very true since that is the point of coming here isn't it...cumming and cumming?" Ginny laughed again, reaching over to put her hand on Jackie's thigh. "We are getting close, aren't we? Can I get naked now?"

In the front seat, Leah tensed and yelped then collapsed on Ed's chest his fingers still down between her legs. After a moment, Leah looked up at Ginny and smiled.

"You do remember the price you pay if you get naked outside the gate?" Leah said softly and nuzzled against Ed's neck.

"And what is that?" Jackie asked the now totally naked young woman.

"If Jasper finds anyone naked outside the gate, they must give him a blowjob on the spot."

"But you're already totally naked, so do you give him a blow job at the gate?" Jackie asked.

"I already owe him so many blow jobs and fucks, he's putting the leftovers in his will for his son George to inherit," Leah laughed. "In fact, George already collected quite a few!"

"Well, I sure as hell mind starting with Jasper," Ginny grinned, stripping off her shirt and bra before slipping out of her shorts and panties.

Her average sized tits sagged a little, their small dark brown nipples pointing slightly off to each side. A thin thatch of light brown hair topped her pussy, with a darker crease running down between her legs.

During the ride, Dori sat quietly, just listening and watching while she sipped her beer. As Ginny stripped naked, Dori did the same, her nipple rings glinting in the reflected light of the headlamps.

"Jasper's gonna love it," Jackson exclaimed as he pulled up to the closed gate.

Jackson honked once and a tall black man of indeterminate age came out of the nearby shack. He walked up to the car and looked inside.

"Hi boss, we were starting to think you got lost," he said in the distinctive island accent.

Jackson just grinned at him as Ginny and Dori got out of the van and stepped on either side of Jasper.

"Hi, Jasper, it's been a while," Ginny cooed as she snuggled up against his body, rubbing her hand down over his chest and across his crotch. "My new friend and I are ready to pay our penalty since we just couldn't keep our clothes on."

Dori fell to one knee and unzipped Jasper's shorts while he fondled Ginny's tits. She looked up in surprise when his enormous uncut cock popped out in her hand. He must have been ten inches long and as thick as a beer can.

With a devilish grin, Dori looked up at Ginny and Jasper as he started fingering the older woman's pussy, then glanced at the van. She flicked her tongue over the huge mushroom head emerging from the fleshy sheath and stretched her lips around that enormous dick to take a few inches into her mouth.

"'B' Pod, Jasper, Ginny's in #1 and what's her name is in #3," Jackson just laughed again and pulled the van away. Jackie stared disbelievingly at that monstrous dick.

"Someone should have told me about him," she said accusingly, "I would have gotten naked too for a dick like that."

"No worries," Ed pipped up from the passenger seat, slipping his shorts off to release his rock hard cock into Leah's hand and mouth, "Jasper is always available for anyone at any time...and he never misses at least one go round with each and every guest here."

Jackie looked back as the van pulled away, in time to see Ginny sink to her knees next to Dori before they disappeared around a curve.

**********

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  • COMMENTS
3 Comments
prop69prop69over 6 years ago
Can't wait for the next chapter

Hope we get started soon.

Love to find a vacation spot like this.

LinneaLundinLinneaLundinover 6 years ago

This should be fun!

SexlessStiffSexlessStiffover 6 years ago
Not bad at all.

Thank you for proofing before submitting!

I see that...rarely. Nice character development, good timeline.

I look forward to tropical breezes.

(I do much prefer anonymous feedback being open, but it is your game)

Thanks!

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