Plaything
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The sun was shining, the sky was a brilliant shade of blue and the waters were calm and obliging. The breeze was light and carried with it the scent of the salt of the ocean. There were no clouds in the sky, neither overhead nor on the horizon. Dark blue liquid stretched into the distance to the port side unbroken by land or vessel. The emerald isle of Catalina lay off the starboard side.
It was the kind of day men who lived their lives on the sea longed for.
Walter Driver looked out over the Pacific ocean and sighed softly as the breeze tickled the skin of his face and neck, pleasantly and much-welcomed as it cut the mid-day heat. He was standing on the tiny exterior deck adjacent to the bridge on the upper deck of the lady Allegra, which was one hundred sixty-four feet (fifty meters) of state-of-the-art Super Yacht, an expensive and ultra-luxurious little gem of a boat owned by the powerful Widmore estate, an old and illustrious family with significant real estate holdings and ties to the world of high finance.
Walter had captained the vessel for its entire two-year existence and had been in the employ of the Widmore family for more than a decade. His previous assignment had been as captain of the Widmore II, the personal craft of Bradford Widmore, eldest son of Huntington Widmore, one of richest and most influential men in the world before his death some six years prior. Working for Bradford had been demanding and challenging, but ultimately rewarding, and Walter had earned over his years of service a great deal of respect and trust from his employer.
Which is why Bradford decided Walter was the only man worthy enough to captain the Allegra, which was a sixteenth birthday present to his precious youngest child, his only daughter, Allegra Widmore.
"You're the only man I trust to watch over my daughter, Walter," the fifty-five year-old Bradford had told him that overcast day two years earlier. "She's my little girl, my baby doll, and when she's not under my roof I need to make sure the people around her are Widmore people through-and-through. The world is a dangerous place for girls like Allegra."
And so Walter had taken the job (with considerable monetary advancement, of course).
The first two years had been the easiest time of his professional career. Allegra Widmore rarely spent time on the ship and when she did, it was with other members of her family or close friends. For the most part, the two years had consisted of Walter steering the boat around as a companion vessel to the Widmore II.
Then Allegra Widmore turned eighteen, however, and everything changed. Of course, access to a twenty five million dollar trust fund tended to have that effect, he reasoned. Example: one of the four birthday parties she threw for herself happened on board the ship with more than one hundred people coming and going at various intervals over the course of the night. It had been the single longest night of Walter's life.
And couple that with the girl's close friendship with Parker Wellington, the son and heir to the Wellington family fortune, who at twenty years was a rather wild young man with great passion for the yacht-living life, and it was easy to see how far downhill Walter's own life had gone.
Walter lived now for those intimate moments when he and the blue waters could reconnect at the deepest levels, moments like the one he was currently experiencing where he basked and soaked in the scents and sounds and splendors of the sea.
A throat cleared respectfully behind him. "Captain?" a voice asked.
Walter turned and found his Second Officer, Albert Graves, standing at attention before him. Albert was a good man and had been with the Allegra since its maiden voyage, as had most of the crew Walter counted on for primary operations of the craft.
"Albert?" the captain asked quietly.
"Weather report came through on the wire, sir," the man replied. "Clear skies indefinite."
The captain nodded. "Thank you, Albert," he replied.
The other man hesitated. "Should I ... tell the boss, sir?" he asked in a voice that spoke volumes.
The "boss" was what the crew often called Allegra Widmore; "Miss Widmore" was other name they used. The name "Allegra" in their circles was always used in reference to the ship itself.
Walter sighed. "No, Albert," he said. "I'll do it."
The other man smiled. "Thank you, sir," he said gratefully.
And so Walter began the short trek up one level to the roof deck, the highest point on the yacht and the spot Allegra Widmore preferred always to lounge about while sunning.
Allegra was easy enough when she was alone, but whenever the Wellington youth was aboard with her the crew tended to have as little interaction with them as possible; the moods of super-wealthy and super-spoiled trust fund babies could change likes the winds. Allegra and Parker had been upstairs together for nearly two hours.
Once arrived at his destination Walter immediately took note of three things: first, that the two young people, neither of whom were of legal drinking age, were sipping from glasses full of what he doubted were full of water or fruit juice; second, that their chairs were facing right into the noonday sun, which meant they were facing towards the direction from which he was coming, which he was thankful for as it required less distance for him to travel to reach them; and, third, that the girl, his employer's precious daughter, was wearing what looked to be the smallest gold bikini in the history of gold bikinis, which he was decidedly NOT thankful for.
The blossoming of Allegra Widmore had happened swiftly: one minute she was a gangly and somewhat awkward girl of sixteen, the next she was a sultry creature of legal age oozing femininity and sensuality from her every pore. Her body filled out in the perfect kinds of ways and her demeanor changed dramatically, too: she was hot and she knew it, and she acted like she knew it. The crew of the yacht, most of them male, were often subjected to her flirtations and teasing, and it seemed Walter himself bore the most significant brunt of it.
"Walter!" the girl squealed as she saw him approaching. Her pair of expensive Gucci shades had lenses so large they covered half her face, but not her smile, which dazzled. She was truly a lovely young woman, which made everything all the more difficult.
Walter inclined his head. "Miss Widmore," he said pleasantly.
"Isn't it a beautiful day, Walter?" she breathed as she rose to a sitting position. Her exquisite breasts jiggled as she moved and for an endless instant he worried they would fall out of her top.
"It is, Miss Widmore," he replied.
She sighed and settled back into the lounger, her bronzed legs stretched in front of her. "Sunny and perfect," she said, then affected a pouty expression as she added, "although this silly boy just wants to go inside all the time. Tell Parker it's more fun to stay outside, Walter, please?"
Parker Wellington had not moved an inch since Walter arrived, but at the mention of his name he drew a lazy hand up to his face and plucked his shades down just enough to make eye contact with Walter.
He was an extremely attractive young man with jet black hair that fell about his face, deep blue eyes and a well-formed physique, which was now on display. He was not the nicest guy, nor the most respectful, but he was not a complete asshole, either: he was the prototypical super-wealthy and boundary-less spoiled rich kid playboy. He had no real job and no real responsibilities, the poster child for the party-and-play lifestyle.
When he spoke, his words were languid and pretentious. "The simple fact of the matter is, Walter," the young man of twenty said, "that I can see more of her inside than I can outside, and the weather never changes. It will still be here when we get back."
Walter was stunned the boy had the audacity to make such brazen remarks to a man who was in the employ of the father of the girl he was pursuing, but despite his flaws Parker Wellington was smart. He knew Walter would never say anything to the girl's father.
Allegra scoffed. "Fine," she countered flippantly, "if you want to see more of me, Parker, all you had to do was ask. It helps with my tan lines anyways."
And to the great dismay and utter shock of Walter Driver, the respectable captain of the yacht that bore her name, Allegra Widmore reached up and undid the strings of her bikini top and pulled the garment away, baring her gorgeous breasts to anyone and everyone who came near enough to see.
"Miss Widmore, please!" Walter exclaimed. He fought valiantly to curb the rising problem in his slacks, which the sight of the girl's incredible assets had exacerbated dramatically.
Allegra waved a dismissive hand. "Don't be such a prude, Walter," she told him. "They're just my tits. I'm sure you've seen a few pair in your day."
Parker chuckled. "Probably not any as nice as yours, though," he said.
The girl looked down at her breasts and hefted each one in her hands. This was swift becoming one of the sexiest and most mortifying moments of Walter's life; he knew beyond doubt that his dreams would consist of those two luscious teardrops for many nights to come.
"They are nice," she admitted, pleased. She looked up at Walter, who at this point was pointedly looking away. "Do you like them, Walter? I trust your opinion more than anyone else, I think."
Walter nodded without looking. "They're perfect, Miss Widmore," he said in a strained voice, which earned another chuckle from the Wellington boy.
"Did you come up here to ogle Allegra's tits, Walter, or was there something else you wanted?" the boy asked with a grin. "She might show you her ass, too, if you want."
Walter decided it was best to get this over with as quickly as possible. "The weather report just came through on the wire, Miss Widmore," he reported. "Clear skies and smooth waters ahead. We will await your instructions. If you'll excuse me..."
Allegra nodded. "Yes, thank you, Walter," she said with a smile, "and thank you for your good opinion. It means a lot to me."
Walter was moving before she was finished speaking. His pants were tight and his heart was racing, and the image of Allegra's exquisite breasts was branded into his brain. His life, he knew, just got a little more difficult, and it did not help that the last thing he heard before moving out of earshot was the following exchange:
"See what I mean about the weather?" Parker asked. "Let's go inside. I want to get my hands on those gorgeous tits of yours."
Allegra sighed. "Alright, but I'm not sucking you off this time. I just put on my lip gloss."
And Walter Driver, a man who was known in sailing circles as a good and honest captain who never shied away from danger or difficulty and could always be counted on in a pinch, could not get away fast enough.
Part One: The Lives of Wealthy Young People
It was an exquisite ass that Parker had clutched in his hands. The cheeks were rounded with just enough flesh to make grabbing or spanking fun, but taut enough to allow excellent viewing of what lay between and beneath. The skin was expertly tanned, the glorious recipient of hours spend sunbathing in the nude, and tight. It was soft where it needed to be and firm where he liked it.
In a word, it was perfect.
Parker landed a heavy blow across the right cheek and Allegra Widmore yelped, then growled. She flicked her bounty of blonde hair around and glared back at him over her shoulder, her blue eyes blazing with a mix of lust and sudden displeasure. But those beautiful eyes fluttered shut and a moan escaped her lips as he pushed forward with his cock once more and buried it deeply inside her oven-hot and vice-tight pussy.
They had wasted little time once they got back to her bedroom on the main deck of the yacht. Allegra went into the bathroom to freshen up after hours of tanning, but was only gone a couple of minutes, and when she returned there had been some light kissing and fondling, but not much more before they got right down to fucking: he had the beautiful girl bent dog-style over her own vanity table, her legs spread wide and her weight supported by her elbows, her ass upturned, her supple breasts swinging beneath her.
"You're a hot little bitch, Allegra," Parker groaned as his cock hammered in and out of her body. "I could fuck you all day and all night and never get tired."
"Do it, then," she cooed, and moaned as he quickened his pace. Her right hand snaked down her body and between her legs to tickle her clit and she moaned again. "Fuck me, Parker! Fuck me!"
Parker reached around and palmed one of her tits, but it was not enough for him. He wanted to see them, wanted to squeeze them, wanted everything those wonderful mounds had to offer; there were few women anywhere with tits like Allegra.
Parker withdrew and grabbed the girl bodily and threw her onto the bed before she had any idea what was happening, and as she bounced into place on her back on the mattress she fixed him with another angry, lusty stare.
"Come and fuck me," she challenged with a sudden grin as she raised her legs high into the air and spread them, exposing to his hungry eyes her gaping and glistening pink pussy.
To hell with trying to get her on top, he decided. He could play with her tits anytime he wanted to, really. And so he pounced on top of her naked body and snatched her calves out of the air with his hands, and forced them back down so that her knees were pressed into her shoulders, in effect bending the girl in half.
Which was the prime position to open her pussy up and prepare it for the invasion of his cock, which he thrust back into her violently until he bottomed out with his pelvis mashing into her quivering ass.
"FFFUUUUCCCCCKKKK!" Allegra squealed.
And to add to the sensations assaulting her, Parker reached under his balls, which were nestled up against her luscious butt, and stuck a finger up her ass. Which also happened to slip in without much resistance at all, far more easily than he imagined it would.
Allegra giggled and revealed, "I lubed it while I was in the bathroom."
Parker roared and began to pummel her pussy with vicious thrusts. Her ass was on the table now, he knew, and he was not going to waste the opportunity. He fucked her as hard and as fast as he could, burying his cock to the hilt every time before withdrawing almost to the end of the tip. The girl was whimpering and squealing and screaming and moaning, and then her orgasm struck and all the sounds meshed together in one indescribable symphony.
"OOHHHHHHHFFFFUUCCCKKKKKMMEEEEEAAAAAIIIIIIEEEEEE!" she wailed in the those of climax as her pussy clamped down upon the invasive rod and juiced poured forth from her depths, and her body quivered and quaked.
And then Parker did what he had wanted to do for a long time: he pulled out and shoved his cock into Allegra Widmore's ass.
There was a bloodcurdling shriek that followed as the head of his cock popped past her anal ring, the kind of sound that might have sent the crew of the yacht running to help them if they did not already know what was going on inside. Allegra's eyes were wide with a mixture of pain and pleasure and shock and lust, and there were tears in them as they narrowed and flashed dangerously.
Parker just concentrated on fucking her ass as best he could, which was hard enough since the orifice was hotter and tighter than almost anything he had ever experienced. It was eighteen years of beautiful blonde ass, by far his youngest and by far his sweetest, and it was glorious.
It took several minutes before Allegra's anus, despite the lube and her own eagerness, allowed complete entry in the position they were in (her feet back up by her head made everything down below tighter) and by that point the girl was a blubbering mess, three orgasms deep with shots of pain and waves of pleasure at odds as they assaulted her.
As his nuts came to rest against the cheeks of her ass, both Parker and Allegra breathed a sigh of contented relief: her that the most difficult part of the invasion was over and him that the muscles of her ass had not snapped his dick in two.
"Flip me, baby," Allegra whispered suddenly. She could be a dirty, dirty girl when she wanted to be and Parker, naturally, loved that side of her. "Fuck my ass from behind."
And so he pulled out with agonizing slowness and watched eagerly as she flipped over and got up onto all fours (an easier ass-fucking position for them both) her palms planted into the mattress and her ass sticking back at him, up in the air again and ready for the taking. She wiggled it enticingly as she looked back over her shoulder, which was one of the sexiest things a girl could do if done right, Parker thought, and Allegra Widmore had cornered the market on executing that particular maneuver correctly.
Parker stepped between her legs and spread the taut cheeks of her ass with his hands, and looked down at the dark red and wrinkled plot of her anus. It pulsed with the anticipation of his cock violating it once more and that was more than enough inspiration.
And so he shoved half his cock back into her ass with one vicious thrust.
"OOOOOOOOOHHHHHHH FFFFFUUUUCCCCCKKKKK!" Allegra howled. It must of felt like she was being ripped in two. Her fingers flew to her clit to combat the pain with more pleasure, and soon she was whimpering happily again.
Parker, however, continued his assault. A few more thrusts and he was buried completely inside her rear portal. His hands spread the cheeks of her ass and he looked down at the lewd and magnificent sight of his cock stretching her anus. He paused then to admire that view.
"Fuck me, bitch!" the girl growled.
Parker roared and gave the girl her wish.
The fucking lasted longer than he expected it to, long enough that he lost track of time completely. He was focused only on the sensations of her ass clutching and milking his cock. He did not pay attention to Allegra and did not try to give her pleasure of any kind, although she experienced a string of powerful orgasms.
His hands gripped her ass hard enough to leave marks, his fingers digging into the flesh as he violated her bowels, fucking her mercilessly in the butt. It was animalistic and raw, and they both loved it.
And then Parker exploded and filled her ass up with what felt like buckets of cum, hot and steaming white fluid that trickled down into her depths. His cock continued to pulse long after the well ran dry and with each pulse, Allegra quivered and exhaled a little gasp.
And then he pulled out of her with a lewd and wet popping sound and stumbled back into one of the chairs, his legs weary and unable to support him any longer.
Allegra collapsed forward onto her stomach on the bed, her legs still splayed out to the sides, her body limp and useless, her asshole red and gaping, held open by what he had done to her. He wondered fleetingly with what mind he had left how long it would take before her anal ring contracted back to its normal position. Sticky white globs of cum dribbled out of the hole and ran down her over her pussy, which was glistening and puffy and twitching from her orgasms.
The only sound to be heard was the sound of their ragged breathing.
"Wow," Allegra murmured after several long minutes of peace. There was a dreamy kind of quality to her voice.
Parker said again, "You're a hot little bitch, Allegra. You might just be my best fuck ever."
Allegra inched her head around to look at him with a beautiful smile on her face, then her eyes narrowed. "Better than the underwear model?" she asked in a dangerous tone.
"Of course," he told her.
"Better than Cassidy Carter?" she continued.
"She's a bitch," he replied honestly.
"Better than that slut from your boat?" she asked.
Parker grinned. "Much better," he admitted. "She won't even let me fuck her ass."
Allegra wiggled her butt just a bit and cum bubbled out of her asshole once more. "Takes a special kind of girl for that," she teased.
"Oh, yes," he told her.
And so they chatted quietly as they lounged in the afterglow of their orgasms, their bodies relaxing after the physical exertion of their frenzied fuck session, but it would only be a matter of time before they grew restless yet again.
Eleanor Wentworth was in her quarters arranging some necessary documents for the monthly restocking of the Allegra when she received the call: the girl and her guest were hungry. Eleanor harrumphed, knowing as most of the crew on board did exactly what kind of activity had perked up their appetites. She rose to her feet and headed for the stairs, and when she reached the main deck she found Tamara waiting for her in the galley.
Tamara Dahl was a beautiful young woman of twenty-eight years and the Crew Liaison on board the ship, which meant she orchestrated the smooth operation of the vessel from a logistical standpoint as well as handled much of the land communication. Also, when there were guests on board, she was their personal aide ala an executive assistant. She had long dark red hair and dark green eyes, and her features held a hint of the exotic, the benefits of a slight Brazilian heritage.
"She wants sushi again," Tamara said with an apologetic look. Sushi was the hardest thing to make and, not surprisingly, Allegra Widmore wanted it often.
Eleanor sighed. She was the stewardess for the yacht, which meant she tended to housekeeping duties and also acted as the cook. She was trained in all manner of food preparation, which was essential when dealing with a girl as flighty as Allegra.
"Alright," Eleanor said as she rolled up her sleeves. "There's work to do."
Tamara looked down at the floor. "There's more," she said in a meek voice.
This was not going to be good, Eleanor knew. "What happened?" she asked in a soothing voice.
"The land office called," the young woman revealed. "Allegra neglected to tell us her high school classes start tomorrow."
Eleanor sighed again. "Have you informed the captain?"
Tamara nodded. "He's setting course for Los Angeles now. The crew has been contacted. We'll have to finish the Catalina rounds this coming weekend."
Several members of the crew were enjoying some needed time off on the island of Catalina and had been told they would have at least a couple of days. They would not be happy when they returned to the ship.
"We'll manage," Eleanor said with a hand on Tamara's shoulder. "And it is not our job to look after the schedule of Allegra Widmore beyond the boundaries of the yacht. There are others responsible for that, or herself for that matter. We are responsible for her while she is on board, and on board only."
Tamara smiled and hugged the older woman. The two had always had a very good relationship, very much akin to mother and daughter. Eleanor had no children of her own and Tamara's own mother had passed away many years earlier; both counted on the support of the other, and often.
"I'll deal with the crew," the younger woman said with renewed confidence.
Eleanor replied, "I'll deal with the girl."
Which is how she found herself en route to the sky lounge, where Allegra and her guest, the rather infamous young playboy Parker Wellington, were probably making themselves drinks despite both of their being underage. She stopped just beyond the swinging door entrance and listened to the conversation coming from within.
"Bored," the boy was saying. "B-O-R-E-D."
Allegra scoffed. "What do you mean? We've had a great time today."
"The exception proves the rule, sweetness," he said. "You still have school to occupy your time. I'd have to go to college for more of that and that is certainly not going to happen. I have nothing to occupy my thoughts these days. I'm bored."
There was silence as Allegra considered. "Buy yourself something," she recommended helpfully.
Parker sighed. "There's no fun in just buying whatever I want," he said.
"So you want something you've never had before, is that it? Something that you can't buy for yourself with money?"
Parker shrugged. "Pretty much," he admitted.
Allegra rolled her eyes. "No wonder you're bored," she told him.
And Eleanor used that particular moment to enter the room and inquire about what kinds of sushi the two were expecting, and also to let Allegra Widmore know that the jig was up and she would be going to school the next day. The girl took the news far better than Eleanor had expected she would, actually, so the experience was not too bad.
In fact, the girl did not even throw a single thing.
Part Two: An Unlikely Friendship
It was the first day of her senior year and Danielle Rosen knew nobody, which is what you got when you moved from your small suburban neighborhood in Ventura County to the fast-paced and ritzy surroundings of West Los Angeles and found yourself smack dab in the middle of one of the most prestigious high schools in the city, maybe even the country.
Four periods had passed thus far and the people had been very nice to her, yes, but she still felt overwhelmed and out of place. The lunch period brought more of the same: she moved into the cafeteria and looked around for the emptiest table she could find.
She never found it. "Want to sit here with us, Danielle?" she heard someone say, and she looked around and saw four very pretty girls seated at a nearby table: three blondes and a brunette. There was an open space between two of them.
"Me?" she asked hesitantly. She had always been a little bit timid around new people.
One of the blondes nodded. "Of course, silly," the girl said playfully. She was the one who had spoken before, too. Danielle vaguely recognized her from one of her classes earlier that day. "Come over here and sit with us."
Danielle approached hesitantly: she had no idea what to expect from the students of such a school. There were exaggerated examples of wealthy southern California high school kids sprayed all across movies and television. She feared the worst.
"Hi," the same girl said pleasantly. She had long blonde hair and light gray eyes, which was quite striking up close and very beautiful. It was also obvious her figure was attractive, too. "Your name is Danielle, right? My name is Jennifer Taylor."
"Hi," Danielle answered, relaxing a bit. It didn't seem too bad, actually.
"I'm Susan," said the only brunette of the bunch, seated to her immediate right. She had big brown eyes and a lovely face. "Pleased to meet you, Danielle. You're very pretty."
Danielle blushed. "Thank you," she murmured as her eyes lowered. She always felt awkward receiving compliments, although she managed to receive them quite a bit: long natural blonde hair, bright green eyes, an attractive face and a nice body tended to have that effect.
"What a cutie," said another one of the blondes with a smile on her face. She had shoulder-length blonde hair and bright blue eyes. "She's blushing. I like this one, girls. I'm Jennifer, by the way. Jennifer Paulson. Although the girls just call me Jenny."
"And I'm Jen or Jennifer," said Jennifer Taylor. "It makes it much easier."
Danielle nodded and turned to the last girl, seated to her immediate left, who was not smiling. She did not seem too excited at all, actually, and for a moment Danielle was worried she had done something wrong.
"I'm Hannah," the last girl said without enthusiasm of any kind.
The other girls giggled and Danielle knew she was missing something.
Hannah sighed. "Fine," she said curtly to the other girls before she turned back to Danielle with an apologetic smile. "Sorry. They are all excited because I have to tell you my name. My full name, that is. It's Hannah Montane, which was an awesome name until that freakin' Disney show made that idiotic Cyrus kid a household name. It drives me crazy because everywhere I go I get the same crap about it and these sluts here think it's hilarious."
Danielle smiled soothingly, more due to her own relief than anything else, and said, "I think it's a lovely name." She decided not to mention that Hannah also happened to look a little bit like Hannah Montana with long straight platinum blonde hair and dark soulful eyes.
Hannah nodded once, firmly, and lifted her chin in the air. "It is," she said emphatically. "This is a smart one, girls."
Mila
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