Kelli

Part 1

The smell was the very first thing she noticed when they exited the tunnel, an overpowering blend of odors unique to the City. Then the never ending variety of sights and sounds deluged the rest of her senses.

Kelli was instantly immersed completely in her first visit to New York City.

She and her boss drove from Erie early that morning in the company's windowless van containing their display for the trade show. After eight hours on the road, they parked in a reserved spot and checked in, her first time staying in a hotel room by herself, not even a year out of high school.

After dinner and two glasses of wine, the long day caught up with her. She reluctantly retired to her room, figuring she had three more days and nights to explore the City and promptly fell asleep.

The early morning wake up call startled her, taking her a few moments to remember where she was. When she realized she was already late for breakfast with her boss, she hurriedly dressed in jeans and a sweatshirt, knowing she would take a shower and dress more appropriately after they set up their display. They barely started to unpack the van when a gruff voice called out to them.

“Wha'd ya think you're doin'?” a rather large man with a protruding belly asked gruffly, stepping towards them from a group drinking coffee and smoking cigarettes in a corner of the loading area.

“Getting the stuff out to set up our display,” her clearly annoyed boss replied.

“Not here you're not,” the man told him. “This is a union hotel and only union members can unload and load a truck.”

She stood off to one side as her boss and the man argued back and forth, finally settling on two hours pay at an exorbitant rate for less than an hour of work for each of two men from the group in the corner. Her boss stood next to her, muttering his displeasure between shouts at the men to be careful, while they carted the display to the showroom and set it up. While her boss unpacked the literature and other handouts, Kelli went back to her room to shower and dress.

She realized her boss asked her to attend with him because, in addition to needing someone at the booth, he wanted a pretty girl manning the display. So she brought along a varied assortment of somewhat revealing dresses, blouses and short tight skirts. Besides, she rarely had a chance at home to wear such outfits or the lacy panties and frilly bras barely concealed beneath them. She had no problem at all flaunting her firm softball sized tits, round ass and smooth shapely legs. If it possibly earned her a bonus or raise, so much the better.

In the shower, she carefully shaved her legs and, after thinking about some of the lacy bikini and thong panties she would wear, she trimmed her wispy light brown pussy hair to an inch wide runway strip. She shuddered slightly running her fingers over the smooth skin above and on the sides of her naturally puffy mound. After a moment's consideration, she decided to put off masturbating until later when she could take her time and leisurely enjoy multiple orgasms on her fingers.

Walking around the room naked gave her another thrill, something she could almost never do at home for fear of one of her parents walking in unannounced. Her half inch long nipples hardening to the point just touching them even lightly sent a pleasant shiver directly to her pussy. She laid out her bras and panties on one side of the bed and her dresses, blouses and skirts on the other, unsure which combinations would be best.

When she realized the time, she chose a frilly white blouse and mid thigh length navy skirt with a five inch slit up her right thigh. She matched the blouse with a sheer demi bra then picked a powder blue thong and and low heel black pumps.

Her boss nodded approvingly when she approached the display then left to shower and change himself. Like her, others on all sides were making the final adjustments to their displays as the area began to fill with people. The boss returned and they spent the remainder of the afternoon talking to potential new customers.

Towards the end of the day, a man who looked to be in his late twenties or early thirties approached, loudly and rather impertinently, shouting out her boss' name. He turned and broke into a bright smile, rushing over to shake the man's hand as they excitedly exchanged greetings.

His name was Jacob and had been a college roommate of the boss's oldest son. It turned out he built a very successful network of business. When he was introduced to Kelli, she immediately noted he wasn't wearing a wedding ring. At dinner later that evening, she confirmed he had never been married.

When the dinner was over, Kelli took the opportunity to explore some of the City around the hotel. She gawked at the tall buildings and some of the colorful characters crowding the streets. About two blocks from the hotel, she saw an adult shop prominently advertising videos and sex toys.

At first she was too embarrassed to go in the shop but after seeing three separate women exit with packages in black plastic bags, she screwed up her courage and entered. She was immediately overwhelmed by the number and variety of videos and sex toys on display. As she nervously strolled around the store, she felt her nipples harden and her pussy juices begin to moisten her panties.

By the time she got to the section with vibrators shaped like a man's cock, she decided she wanted to purchase one since she would not have a chance like that at home. She found a slightly curved one imprinted with veins and a head that was not too large around, perfect for both her pussy and ass. She blushed when the bored clerk added a four pack of batteries without even asking when she went to check out.

As soon as she got back to her room, she tore open the packaging, loaded two batteries into the vibrator and turned it on, cycling through its three speeds excitedly. Satisfied that it worked, she quickly removed her shirt and bra, pulled off her jeans and panties and flopped on the bed with her knees drawn up.

Running a finger through her pussy slit confirmed she was already as wet as she normally got by the time she finished masturbating to a satisfying orgasm. She turned the vibrator on low and tentatively touched her already throbbing clit, shuddering and letting out a low cry as a bolt like electricity coursed from her pussy through her legs and body. She pressed the tip of the vibrator against her clit firmly, unexpectedly cumming hard within only a few seconds from this entirely novel stimulation.

For a few moments she lay on the bed breathing raggedly until the aftershocks of that first orgasm ebbed away. When she reached down between her legs, she realized how much wetter she had become. She dragged the tip of the vibrator up and down in her pussy slit a few times before sliding it into her dripping entry and cunt canal.

Satisfied that the toy was adequately slick with her juices, she slipped a pillow under her lower back, pulled up her legs and rubbed the tip set on low over her puckered asshole. Another soft moan escaped from her mouth as her sphincter loosened and she slowly pushed the tip into her asshole an inch at a time until it was completely buried in her bowels.

She chose that particular vibrator because it came closest to the size and shape she remembered of her step brother's cock. He introduced her to ass fucking the summer before he went to college on the west coast when she was only eleven years old. Since then she preferred a cock filling and cumming in her ass more than her pussy.

When she finally had the vibrator buried in her ass as deep as it would go, she turned it on to the high setting, pumping it in and out as hard and as fast as she could with one hand while frantically rubbing her engorged clit with the other. It never occurred to her that others on the hotel floor probably heard her loud shrieks as she climaxed over and over until she collapsed in exhaustion, falling asleep with the vibrator still embedded inside her ass.

Over the course of the next three days, Jacob made a point of stopping by the display to chat with Kelli and her boss, making it clear he wanted to talk to them both again after getting back from an imminent business trip. Her boss made a point of informing her that Jacob was quite wealthy.

The second night, she did some more exploring before returning to the hotel to fuck her ass and pussy repeatedly with the vibrator.

The third night she imagined herself on her hands and knees with Jacob hovering over her, his rigid cock pumping her asshole until his creamy cum erupted deep inside her.

Two weeks later, he called Kelli at home, having gotten her number from her boss.

A week after that, he flew his own plane into Erie to take her to dinner.

The following Friday, he returned and she met him at the executive airport to drive him to the hotel he booked for the weekend.

The door barely closed behind them when she turned into his arms, frantically pawing at his clothes as he did the same with hers. They spent the weekend together, barely getting out of his hotel room bed to eat.

Almost immediately they discovered they both preferred anal sex. After cumming first in her pussy, Kelli shyly asked him to next fuck her in the ass and found out, unlike a few guys she hooked up with, he was more than willing to oblige her.

At his behest, she quit her job and traveled with him to his various business interests around the country. After a whirlwind relationship, and Jacob happily loving her ass as often as she wanted, they married in Vegas and honeymooned in Maui for a week.

At this point, Kelli's life changed dramatically. Jacob's primary residence was in Florida, so after the honeymoon, they returned to Vegas to get his plane and fly to an executive airstrip just north of Orlando near his home.

“Before we get there, I have a few things to tell you,” Jacob told her after they were at cruising altitude outside Vegas with the plane on auto pilot. “There are some aspects of my life that you may...um...shall we say...er...find a little...uh...unusual.”

“What in the world are you talking about?” Kelli asked, settling into a comfortable seat facing him.

“Well, I haven't mentioned this to you before since I didn't see the need,” he continued, uncomfortably squirming in his seat, “but now that we are going to my...our home...you need to know.”

“Just spit it out, Jacob,” Kelli told him peevishly, “I doubt you could surprise me.”

“Alright...I'm a nudist at home. I was raised that way and my family have been nudist for generations,” he said softly, searching her face for her reaction.

“Hmm, well I was wrong...that is a surprise,” Kelli responded after a moment. “I'm not so sure how I feel about that, Other than my doctor and mother, you are the only other person who ever saw me completely naked. I never even got completely undressed for the two other boys I fucked in the back seat of their father's cars before I met you.”

“I think you'll find that you don't even think about it much after a short time when everyone else is naked,” he went on, “but, as they say in the late night commercials, wait there's more.”

“What the hell do you mean more?” Kelli gasped excitedly, “And who is everyone?”

“My house is located at a nudist resort I own,” he said sheepishly, “and about a dozen families live there year round. Then there's Lena, my housekeeper. She's been with my family since before I was born. In fact, she was my wet nurse for a year or so.”

“Families?...you mean with kids...little kids?” she asked in astonishment.

“Well, yes...although not all are little,” he replied lowly. “They range in age from infants to teenagers, boys and girls.”

For a few moments, Kelli just stared at him with her mouth partially open. Then she got up and moved to a seat at the rear of the plane without saying a word. Jacob had enough sense to leave her to her thoughts and retreated to the cockpit. An hour or so later, she knocked on the cockpit door.

“We need to talk some more,” she murmured softly, turning to return to the main cabin with Jacob following meekly behind her.

“I...I really didn't mean to shock you,” Jacob started to say before Kelli cut him off with an arm wave.

“I'm not so much shocked as a bit overwhelmed,” she began, taking his hand in hers, “but while I'm not at all sure about this...er...arrangement, I'm willing to give it a try. Just try not to surprise me like that in the future.”

He agreed readily, leaning forward to give her a passionate tongue lashing kiss. Within moments they were groping each other, pulling off their clothes. Jacob opened a sofa into a bed, gently pushed her on to her back and crawled between her already spread legs.

“Welcome to the Mile High Club,” he smiled as he gently pushed the dripping head of his rigid cock into her wet, warm and most hospitable pussy.

“We're here,” Jacob announced as he turned off the two lane highway onto a private road with a gravel surface lined with a thick hedge of bougainvillea on both sides. After about fifty yards, the hedge opened on their right side to a tall steel gate next to a discreet sign that simply said:

Bahia de Soleada
Members Only

“That's the resort,” Jacob told her unnecessarily then drove on another twenty five yards or so to a second gate, “our house is this way.”

He opened another gate with a remote and turned around the far end of the hedge. A sprawling modern single story house came into view. He pulled to a stop on a circular cobblestone driveway at the front door.

“Wow, this place is really something,” Kelli exclaimed, exiting the car and curling her arm into his.

“Lena, we're here,” Jacob called out after they entered a glass enclosed foyer filled with a variety of tropical plants.

A few moments later, an older black woman about Kelli's height, wearing a white apron, came out of a nearby doorway smiling brightly. She was very stout, her body pretty much a barrel from her shoulders to her ample hips and thick thighs. It took Kelli a few seconds to realize that, save for the apron and a pair of sandals, she was completely naked.

“Well, Jakie, it's about time you got home,” she scolded him with a warm smirk on her face, “and I assume this is the foolish girl you managed to trick into marrying you.”

As soon as Jacob introduced her, Lena gave Kelli a warm hug, crushing her huge dangling tits against Kelli. Then, after telling them dinner would be at 7:00, she turned to return to the kitchen, giving Kelli an unobstructed view of her fat ass cheeks and the dark crack between them.

“Jakie?” Kelli whispered to him with a impish smile as Lena walked away.

“Yeah, she's called me that for as long as I can remember, not matter how many times I tell her I don't like it.”

Jacob led her to the master suite, a series of rooms larger than her parents' house. As soon as he entered, he proceeded to strip naked, throwing his clothes in a heap near the door.

“I need to go check with Gene to see if there are any problems needing my attention,” he told Kelli while absentmindedly scratching his hanging ball sac. “You can stay here or join me but you do need to know nudity is mandatory for everyone inside the resort.”

“Oh hell, I can't stay hiding in this room the rest of my life,” Kelli exclaimed as she quickly stripped out of her clothes, “so might as well get this over with as soon as possible.”

Jacob just grinned watching her then extended his hand, noting without comment the way her nipples stiffened.

“Hold on, girlie, you can't go out like that...not on your first day here,” Lena called from behind them as they walked through the kitchen toward a door leading to the resort.

“Why not?” Kelli asked, stopping to look at Lena. “I'm only wearing tennis shoes. Don't tell me I need to take them off too?”

“Oh no, that's not it,” Lena laughed heartily, her dangling tits with huge dark brown areola and marble sized nipples visibly jiggling under her apron, “but you do need to think about protection from the sun or you'll get terribly burned in some very uncomfortable spots.”

With that, she disappeared into a nearby pantry and returned a moment later with a floppy straw hat and a bottle of sunscreen.

“OK, turn around and I'll do your back first,” Lena instructed Kelli in a voice that brooked no disagreement.

She started on Kelli's neck and shoulders, slathering the sunscreen on generously down her back and sides. Kelli shuddered slightly when Lena's fingertips brushed against the sides of her tits.

When she reached Kelli's ass, Lena added yet more sunscreen to her hands, grinned devilishly then took her time rubbing the creamy lotion into the skin on Kelli's cheeks. She even dragged a finger up through the crack in Kelli's ass before finishing both legs, her thumbs lightly contacting Kelli's pussy, eliciting another shudder.

“Now turn around and face me,” she told Kelli after finishing her legs.

Very gently, Lena covered Kelli's face before working her way up and down both of her arms. She smiled sweetly as she slowly moved her hands down Kelli's chest, circling both of her tits before cupping them at the same time. Kelli let out a low moan and quivered all over as Lena slowly massaged her tits, finishing by thumbing her hard nipples before adding more lotion to her hands and coating her belly.

Lena's grin grew as she rubbed more of the lotion through the thin patch of runway hair above Kelli's pussy. She then dragged her hands down the front of Kelli's thighs to her knee before coming back up on the inside of her thighs right next to both sides of her puffy pussy mound.

Kelli shivered again at that touch, moaning a bit louder when Lena cupped her bare mons. Lena continued down the front of her legs, including the top of her feet then stood back looking at Kelli critically.

“Just one more thing,” Lena murmured, squirting another gob of sunscreen on her hand before reaching between Kelli's legs, splitting her pussy lips with a finger and rubbing the lotion on the inner folds of her cunt, plunging a finger into her canal entry and encircling her now engorged clit.

“You don't want to get sunburned there if you lay down on one of the recliners by the pool,” Lena explained with a twinkle in her eye when Kelli tried to step back, “and don't forget to keep the hat on while outside.”

As this went on, Jacob stood off to one side, a bemused look on his face. Then Lena turned to the well tanned Jacob and repeated her performance, rubbing the sunscreen over his entire body, ending with his stiff cock in one hand and gently squeezing his balls with the other. When Lena was done, he took Kelli's hand and led her out the door, stopping to put on the floppy straw hat before exiting.

“Well that was...interesting,” Kelli, her face flushed, told him as they walked on a well worn path toward the mobile homes on that side of the resort.

“Lena can be very protective,” Jacob replied with a smirk, “and she likes touching others, especially women.”

“Now you tell me,” Kelli exclaimed, stopping to face him. “I've never been touched by another woman like...like that.”

“Well you don't look like it hurt you in any way,” he answered before leaning over to give her a tender kiss, “if anything, you looked like you were enjoying the way she touched you.”

“Yeah, it did feel kinda good,” Kelli answered as they continued walking.

“Then just enjoy it and chalk it up to another surprise,” Jacob told her as they passed by some of the mobile homes.

^^^^^^^^^^

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