Sea Sicness

*** The author retains all rights to the creative material contained within the following work.***

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There were benefits to being rich. Allyson McDaniels was very rich. And she had, for the last several years, been living vicariously through others. Recently she had decided that she was going to extend this over arching manipulation a little further. She set up a small website, linked it very quietly to some major discussion boards and topics of things that she wanted. The few people who responded to the initial bait were cautious and couldn't believe what she was offering. She kept in regular contact with them over the course of several weeks until she finally decided on the person that would serve as her first test subject.

The young man who was selected was named Ryan Harper. He had responded to Allyson's posting on the General Board of an erotic fiction website and had been hooked ever since. Ryan and his family were typical white middle class people- conservative, educated, semi-religious. His mother had raised him and his sister for six years after receiving full custody of them. His father had not been around since the divorce and almost everyone agreed the family was better off for it. Ryan had a secret fantasy that he had been harboring since he first hit puberty. Now that he was eighteen, he was finding it difficult to contain and keep private.

According to his private messages to Allyson following their initial discussion in the boards, he had been regularly spying and photographing his sister and mother. Later, when afforded a chance, he would masturbate into their used underwear while reviewing his haul. His older sister and mother looked very much like each other and he looked like their father. They were dark-haired and dark eyed brunettes with long legs and distinctly feminine curves. Some of his favorite pictures came from them working out in the basement bonus room, their fit bodies drenched in sweat and the tight shorts and halter tops clinging to their skin. He had been caught masturbating by his sister and their relationship had suffered. Luckily for him, she had not seen the lacy thong he was stroking himself into when she entered the study.

Ryan was excited by the opportunity that Allyson promised him. She had asked him to detail his fantasies, send photographs, provide personal information, and dates when the family unit would be available for her plan. He had remained skeptical until the letter had arrived in the mail. His mother had left it on his bed- it was post marked from a company in Miami called Lap of Luxury Vacations. He opened it in his room and read over the brochure, airline tickets, and other items before deciding to begin the adventure.

Sandra was caught off guard by the sudden exclamation and pounding coming from upstairs in Ryan's room. Slightly concerned, she hastily walked up the stairs and stepped into the doorway. Her young, eighteen year old sun ran towards her, his strong arms lifting her in the air and spinning around while he laughed excitedly. Sandra couldn't help but be pulled into his infectious excitement. It took her a few minutes to get him to drop her and explain what was going on. According to him, he had entered a contest in the mall several weeks ago and they had just notified him of his win! She was skeptical of these promised wins, but as she read over the brochure, examined the airline tickets, and the only contact being required was that they confirm their intention to attend. Then she too decided to go jumping around the room. Her family was close knit, but they had lacked time together ever since the divorce. This vacation was a blessing! The opportunity to spend a month together aboard a fully equipped yacht with a chef and personal assistant blew her away. Immediately, she called Alexis, her daughter and Ryan's older sister on the cell.

Once Alexis heard the news, Sandra had to take a few more minutes to calm her down. Immediately her daughter promised that she would leave cheer practice and head home. Alexis was a freshman at a nearby university and had gone to school on a scholarship for her dance and cheerleading. Ryan and Sandra went online together, while waiting for her to arrive, looking up the company web page. She sat in his lap as page after page of beautiful pictures of a sleek yacht and its exotic destinations slipped by the screen. Unbeknownst to her, Ryan's mind was already racing months ahead to summer, when Allyson had promised him results. Seeing the excellent front she had put together, he began to believe she just might be able to produce them for him. Ryan was momentarily grateful that his mother was just lightly resting on one knee and not farther back. His erection was more than obvious in his warm ups.

That night the family celebrated their good fortune, and for the first time in months, Alexis was friendly and relating well with her younger brother. It was a fine start for Ryan and Allyson's plans.

The next weeks and months would fly by quickly for the small family. Sandra's excitement carried over to her work and she was promoted. For the first time in a while she was genuinely looking forward to each day, rather than dreading the start of another morning. Alexis worked out like a fiend, hoping that all the cute foreign boys she met would make this a trip to remember. Ryan was doing the same, but of the three he was the least excited. He was horny and fantasizing all the time, and both his sister and mother wanted to spend more and more family time as the trip grew nearer. He didn't mind constantly being around the two beautiful women, but he never got a break. His dick was running high octane fuel and he was having difficulty meeting its expectations. But finally the day would come, and the three Harpers packed, left their home, boarded their plane, and flew to sunny southern Florida, where the yacht would meet them.

At the airport, Ryan and his family had their first chance to meet the captain of their little cruise and the help. Ryan knew already that the boat would be operated by Allyson and a woman she had described as her friend. But even Ryan's fantasy filled mind was little prepared for the two gorgeous beauties who met them.

Allyson was tall, almost six feet one inch, with a thin model's frame. She wore a thin linen shirt that allowed Ryan to catch sight of a white bra beneath. Her breasts sat high on her chest, the deeply etched v of her substantial cleavage enhanced by the contrast of her tan skin to the color of the material. A long pair of khaki linen pants complemented the shirt and were perfectly tailored to the long legs that seemed to go on for eternity. Ryan had to shift his member in his trunks before he even managed to examine the woman who would be the family's personal assistant. She was a brunette woman, probably in her early twenties, with much smaller curves. But in her waiflike appearance there was a distinctive and elegant beauty. She wore a matching outfit to Allyson's, except she wore no bra. The small dark tips of her nipples clearly formed beneath the thin linen.

Sandra smiled softly to herself as she saw Ryan's stiff and awkward reaction to the two beautiful women who were apparently going to be hosting them for the next several weeks. Her son had dated briefly in his senior year of school, but just days before the trip was set to begin, the girl had broken it off with him saying that he was too distracted. Sandra had not heard that line before, but she was happy to see him responding like any young male to the unique beauties waiting for them. Sandra introduced herself first, and then her two children, hoping Ryan's lapse of focus would not be overly obvious. But guessing by the grin on Allyson's face, Sandra was sure that the woman understood what had happened perfectly. Once the introductions were completed the five-some headed for a waiting limo and drove to the marina they would be leaving from. The group made small talk, getting to be comfortable with one another along the way.

Allyson was thrilled with the family. They would be perfect for her game. Already she was eager to get alone with the Simone, the lithe creature who would be traveling with them. Her mind was running wild with possibilities and all the little risks she would be taking. And when her mind ran wild, so did all sorts of things and she was particularly looking forward to what Simone could do to calm her down. Once they arrived, Allyson gave the family a tour of the boat, opting to stroll behind the group, admiring Ryan's older sister's near perfect form and that of his mother. Here the first step in her grandiose plan kicked into gear. The boat they would be taking had a large master stateroom and a smaller cabin that she and her partner would be sharing. The trick was that the stateroom had one bed, a small chaise lounge, and the bathroom was open to the rest of the suite. Although the shower enclosure was made of heavily fogged glass, there was a lack of privacy which was intentional.

Sandra frowned slightly at the suite. If it had been the two women traveling the accommodations would have been considered luxurious but with Ryan along there was little privacy for the family to have. The toilet was at least hidden from view, but undressing for the shower and getting changed would be a difficult task for them to accomplish. Not wanting to allow the near perfection of the trip be ruined by this one lacking area, she said nothing. Alexis experienced similar thoughts, but also said nothing. Ryan, however, was thrilled. Allyson had filled him in well before hand and explained the purpose behind the arrangement. Ryan was pretty sure that he would not be able to relax until all of Allyson's promises and his fantasies were fulfilled. He was a little caught off guard when Allyson asked him to come up to the boat's state of the art control room. She politely explained that the Lap of Luxury was going to use the vacation for some promotions down the line and that they wanted to photograph Ryan and interview him before they left shore. Sandra and Alexis were busy unpacking and were happy to have an opportunity to change without their male relative around.

Ryan followed the swaggering ass of the beautiful woman who had promised him fulfillment of his most obscene and explicit fantasies. His dick bounced happily in his trunks with the enthusiasm of a puppy's wagging tail. Allyson ushered him to a swivel chair, set back off of the actual steering apparatus and primary controls.

"How are you doing, Ryan?"

"Perfect. I can't believe this is for real. I mean, when I got the letter and the tickets and everything I thought I did. But now that I am here, it just seems like it can't be real," the young man gushed.

Allyson momentarily leaned away from him to press and intercom button that sent a message to the rest of the ship; "Simone to the control deck, Simone to the control deck."

"It is all real Ryan. This boat has been customized all throughout for your fantasy. It has every amenity possible and is built to bring your mother and sister to fulfill your desire. All I want is to watch. If you choose to allow me to participate, then perhaps I shall. We can discuss that later. But first, let's celebrate," Allyson said as she offered him a flute of champagne.

As they were raising the glasses to their lips, Simone entered the control room. She went to Allyson's side and stood expectantly beside her captain. Allyson sipped slyly for a moment before she told the smaller woman to seal she and Ryan's agreement. A small nod of the head came from Simone and she acted knowingly. Ryan was caught off guard as Simone turned towards him and unbuttoned her top. Once again his prick bounced to life in his shorts. Wide eyed and slack jawed he stared as she fished the tails of the shirt from her pants. That completed she stopped, frozen before him. Ryan looked to Allyson for answer but all he got was a nod. Hesitantly, Ryan reached out towards the opening that split the top of her shirt. His hands shook as they pressed into the hot flesh of her bared neck and collar bone. It jerkily fluttered across the exposed skin before shifting down to the next button in the row. Simone's piercing green eyes watched him as his hands clumsily popped one button after another free, until the top stayed in place merely because of Ryan's inexperience. He looked up at her, fearful that this game would end soon, but finding only a coy smile and the beautiful eyes staring back at him. He returned to his mission.

Ryan peeled the shirt back from her shoulders, swallowing as he watched it flutter to the floor. Before him the young beautiful woman stood topless. Ryan studied her small breasts, the light shading on their underside, the proud brown tips of her erect nipples, the soft rise and fall as she breathed. He glanced back to Allyson and was ecstatic to find her with one hand buried beneath her khaki pants. She had the same small grin on her lips as she watched the inexperienced young man toy with her pet. Ryan studied the slow shifts in shape in the crotch of the khakis, having only seen actions like that in the porn movies he downloaded at home. But Simone was a more immediate offering and he quickly returned to the study of her pert young breasts. He almost forgot that she would not stop him, whatever he did, so entranced by her torso was he. Then it came to him like a flash and he was on her even faster. Ryan lurched to his feet, causing Simone to drop back a step but his hands quickly closed the distance. They roamed over her breasts, squeezing, petting, pinching, rubbing, lifting, and toying. Simone's grin grew bigger as he backed her into the wall, his eyes never leaving her breasts. It took him a few moments to come back from this most recent of explorations, but when he did, he quickly tore into her pants.

They were held up by a woven band and nothing else. One quick tug of the wrist and the band came free and the pants slid down her hips to her ankles. Simone helpfully stepped out of them and kicked them away as Ryan studied the newly revealed territory. He looked happily over at Allyson. By now, her pants were pushed down away from her crotch and waist and sat just above her bent knees. Her hand was now vigorously stroking in and out of her shaved cunt. Ryan studied this with a childish curiosity before Simone brought him back to her. She had pulled loose the laces on his swimming trunk and pulled the elastic band and netting down over his dick until they sat just over his balls. She grinned cheerfully up at him as his hungry eyes roamed over the small hand clutching the base of his dick. With a low groan he pressed forward, his mouth covering hers and pressing her head into the wall. He pressed his cock into her stomach, the smooth sensation of its taut smooth surface against his head made him groan even more. Simone's hand began to lightly stroke from the position it was trapped between them. Simone nipped and licked and tongued in response to Ryan's rough and unpracticed kisses.

It did not take him long to begin to explore other aspects of her feminine anatomy. His right hand dipped between her thighs and squirmed to find purchase beneath her panties. Once inside it eagerly pressed a single finger into her moist hole, while his other hand clasped the soft flesh of her ass in its palm. Simone squirmed up the wall against him, until she was suspended by the pressure of his weight against her body. Her hand, still clutching his dick, pulled downward, guiding it to the area his finger currently occupied. Their foreheads met as they both stared down their bodies as the tip of his dick experienced its first meeting with pussy. The vision did not last long as the lust of a virgin teenage boy took over. Ryan rammed the length of his cock into the tight passageway of the light woman he cradled in his arms. He hammered its thickness into the indescribable joy of a wet cunt. His movements were impulsive and unplanned. All he wanted was to be buried inside the tightness of her depths and no more. Simone squirmed on his dick as it pounded into her. She knew that the boy would not last long and she hoped to have the opportunity to orgasm before he blew his load. She managed to get her hips rotating in such a way that her G-spot was continually hit by the tip of his penis.

When she did orgasm her head slammed painfully back into the wall and all of her bodies muscles went into lockdown. Her arms wrapped tightly around his neck and her thighs crushed Ryan's crotch into her own. For a few moments her whole body trembled. Ryan's head filled with starbursts of confusion, darkness, and excitement. He felt like he was passing out and getting an adrenaline rush all at the same time. The firm clutches of Simone's cunt stroking on his cock drove him into his first orgasm inside a woman. Spurt after spurt of his hot semen flooded her twat, the heat of it building up deep inside her. Simone began to kiss him repeatedly all over his face as the juice settled over the tip of his dick. Exhausted, Ryan dropped his cradle on Simone, and his dick popped with a slurp from her body. Strings of his fluid and hers flipped onto the floor and dripped down her legs. Ryan stood there, almost paralyzed from the after effects of his orgasm. His paralysis lasted only briefly as the small woman dropped to her knees in front of him and licked his cock clean of the sticky white fluid covering it. Her eyes stared up at him as he stared back down at her while her small tongue lapped up and down his length. Small droplets of fluid were coaxed from the tip of his cock, but she hungrily gulped them down.

Ryan's hands lazily ran through her hair and for a moment he wondered if he were in love. That was broken by the cold applause from Allyson's semi-nude form. Her pants were still around her knees and glistening puddle had formed on the leather cushion beneath her. She had the same sly grin on her face as before, but she looked much more relaxed. At the sound of her applause, Simone slipped from in front of Ryan and slid to the floor beside her. Ryan turned, his shorts still at his ankles and his cock limply dangling before him.

He muttered a small, "Thank you," before he gathered his shorts and left the two women to return to his shared cabin. The experience instilled within him a new sense of confidence that his mother and sister were his for the taking. By the time he made it back to the cabin there was no sign of his sister or mother and he returned to the top deck in search of them. Simone, Allyson, Alexis, and Sandra all sat around a small table secured to the rear deck of the yacht, chatting casually. His mother and sister were both wearing small bikinis that stretched as they sought to restrain the curves of their breasts. Ryan paused momentarily in the shadow of the doorway, his heart skipping happily within him, before he stepped into the sunshine. Out in the open, he fought to keep his eyes focused on faces and not the full chests he had dreamed of seeing like this. Allyson still wore that same self gratified smirk as before. She knew what this was doing to the boy and she knew that his mother and sister were innocent enough to be ignorant of the damage it did to him. Ryan pulled up the only available chair, between Alexis and Simone and plunged into the conversation.

He had only been there for a few minutes before he felt Simone's hands slip into his shorts. Once again his cock began to throb to life, stiffening and lengthening as the tips of her fingers danced over its surface. His dick lurched unevenly beneath the restraint of the netting as her fingers slid around his length and began a slow short stroke. Ryan was fully erect when Allyson announced it was time to go, and the hand quickly vacated its hold. His heart rate came crashing back down as Simone and Allyson disappeared into the shadow of the cabin, headed for the control room. The month long get away had truly begun!