Fantasy Island Getaway

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Five winners get to live their fantasies.
10.1k words
4.46
39.8k
10

Part 1 of the 2 part series

Updated 10/17/2022
Created 09/23/2010
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The advertisement appeared in all of the major daily newspapers and on television:

'Fantasy Island Getaway.'

Win the opportunity of a lifetime and live out your sexual fantasies on a tropical island holiday. 10 Days and nights in Paradise with all of your sexual needs catered for in luxurious accommodation. All you have to do is to fill out the attached form and tell us in twenty five words or less about your fantasy.

Television viewers just dial the toll free number or log on to our Web site and answer a few simple questions.'

Richie Johnson stared at the ad in amazement, he read it three times just to be sure that he wasn't seeing things. He then took a pen from his pockets and filled in the details finishing with his fantasy; 'I would like to live the life of a Sultan, with wall to wall harem girls there to fulfil my sexual needs.'

His mind drifted to his lifestyle, a series of one night stands spanning the last eight years of his life, what could be better? No commitment, no comeback, life was one long orgy with a different girl each night.

He placed the completed form in an envelope and posted it on his way to work, thinking to himself that, if he won, he would be top dog among his friends, definitely the Alpha male.

Joseph Berman stared at the ad that interrupted his late night TV viewing and reached for the telephone. As he dialled his mind went to the bedroom where his wife of forty years lay, softly snoring her way through the night. The woman that he fell in love with all those years ago had lost her appeal, she was showing her age and was no longer attractive to him. Her attempts to arouse his sexual interest disgusted him.

Following the prompts, he gave his details and, when asked stated that he would like to make love to a young woman like the one he fell in love with forty years ago.

Janice Soderberg thought of her husband who would be waiting for her to go to bed after their dinner and who would burst into tears at her lack of response to his attempt at lovemaking. It wasn't as if he didn't try, his foreplay was kind and thoughtful, it was just that, as soon as he put his small cock into her, her desire for sex disappeared, and after a few minutes, so did his. His frustration resulted in tears on his part and masturbation on hers. Oh for a big cock that would give her pleasure. 'I want to be fucked by a big man with a big cock.' She was shocked at her words but sent in the form anyway.

Cindy James stared at the ad in the newspaper on the desk in front of her. Here was her chance to get away from her life for ten days, a life that existed for others, her boss who acted as if she was a dumb blond good for nothing better than to make his coffee and give him blow jobs from under his desk when he felt the need. Then there was her mother who continually told her that she would amount to nothing, and that she would end up a slut just like her. She insisted that Cindy should dress to show her 'assets' and that she should always comply when a man asked her for sex. 'You won't get a man unless you give him what he wants Cindy, you mark my words!'

Just once, Cindy thought as she completed the form, just once I would like to have a relationship with a man who cared for me as a person and not a sex object. 'I would like to be loved by a caring man who knows how to treat a woman properly.' She wrote in the space provided and sent the form away.

Her class of little monsters gone for the day Julie Rogers sat and stared at the newspaper in front of her. Her fantasy for the last several years was to be in the company of adults, male adults, and to let herself think about nothing other than have men cover her with their attention, sexual attention. Just about every man that she had met since beginning to work as a Pre-school teacher had said, 'How nice.' In response to her telling him what she did for a living and then finding someone more interesting to talk to. She loved her job and saw plenty of potential in her children, potential not recognised by their busy parents who believed that the obligation to the kids ceased at the door of the Pre-school centre.

She completed the form and posted it on her way home to her apartment and her books.

The city offices of Fantasy Island Getaways were inundated with responses to their advertisement to the point where extra casual staff was required to sift through the thousands of applications.

Eventually these were reduced to one hundred and the Manager and his Assistant sat around a large table pouring through them before selecting five people. Confirmation letters were sent and instructions given where and when they were to assemble for the trip.

Five complete strangers gathered at the office and, following checks of their documentation, were ushered downstairs to a waiting minibus and driven to the airport. There was no conversation between each of the winners although each of them was busy surreptitiously checking the others out, before deciding that there was nothing of interest there.

It was a long flight to the main island of the group of Pacific Islands. From there a boat ferried them to the resort. From the sea the only sign of the existence of the resort was the small jetty jutting out into a sheltered lagoon. It only became visible from the boat after it had navigated its way through the protecting coral reef into the calm lagoon waters.

A man walked from the trees to the jetty and deftly caught the mooring rope thrown from the boat. He helped the boat crew to unload the passengers' luggage and stacked it on a trolley on the jetty.

As soon as they had all disembarked the mooring line was thrown back onto the boat and it backed away from the jetty, turned around and headed back out to sea.

"Come with me." It was an order softly spoken, the only words spoken until the group emerged from the dense forest into a clearing. In front of them was the resort's main building, carefully constructed to blend into its surroundings, even from the air it would be difficult to spot any of the buildings.

From the building emerged a man, neatly dressed in cool tropical clothes, cream slacks, a blue shirt, white canvas shoes and a white panama hat. He was accompanied by a woman also dressed for the tropics in a floral patterned dress, white low heeled shoes and also a white broad brimmed hat.

"Welcome to Fantasy Island, I am your host for the next ten days, my name is Michael Moss, you may call me Michael, and this is my assistant Elizabeth, she prefers to be called Beth. Won't you come inside out of the sun and we can become acquainted over drinks. Your luggage will be taken to your cabins and after drinks we will introduce you to your personal butler who will look after your needs. Come." He led the way inside and showed them to the lounge where a waiter and waitress waited to take their order.

"Now, first things first. After you have settled in and I would suggest that you get some rest before dinner, after which we will be talking to each of you individually to finalise the details of your fantasy so that your stay with us will be a memorable one."

Drinks were quickly and quietly served and the guests began to relax, not to the point of conversation, but the tension seemed to drain from their faces. Michael had a clipboard on which were several sheets of paper. He looked at the top sheet. "You must be Janice." He said looking directly at Janice. She wondered how he could be so sure before she realised that she was the oldest of the three women.

"Yes I am." Her voice had a quiet assurance about it that came from her position of authority both in her work and domestic life. The others looked at her, trying to work out what her fantasy would be.

"Excellent. Your butler will be Jonah, he will look after you very well indeed." Michael indicated an immaculately dressed Islander man, a good six feet three tall and weighing at least two hundred pounds. His honey coloured complexion was clear and without blemish and his deference at his introduction extended to his voice.

"Welcome to our home and your home for the next ten days Ms Soderberg I hope to make your stay a pleasant one." A slight bow of the head completed his welcome.

"I'm sure that you will." Janice wasn't the only person to believe that her fantasy was already well on the way to being met.

"Now Cindy James, your butler is Reuben, he will be only too happy to serve you in whatever way that you want." Reuben could have almost been Jonah's twin brother, his stature was identical, and his welcome was almost word perfect for Jonah's.

Cindy smiled at him and her smile announced that she was perfectly happy with everything so far. "I'm looking forward to this." She gave him a wink that spoke volumes.

"That brings us to Julie Rogers. Your butler will be Simon." If Jonah and Reuben were twins, Simon was their father, he was the same height but just a little more thick set, he wasn't overweight by any means but his shoulders were wider from years of paddling the long dugout canoes of the Islands.

"I will be pleased to serve you, you can rest assured of that. You are a most welcome guest." Again the slight bow of the head in welcome.

"Now, Mister Berman, your butler will be Naomi, she will ensure that your stay with us will be everything you desire." Naomi was beautiful, her honey complexion and black, waist length hair was contrasted to the formal black skirt and white blouse that she wore.

"Mister Berman, it will be my pleasure to make you as comfortable as possible during your stay, anything that you need, you have but to ask and I will get it for you." She also gave a slight nod in welcome. Berman noted that she said that she would get anything he desired, not that she would try to get it.

"It is my pleasure to meet you." He smiled at her and held out his hand for her to shake.

"And that leaves Richard Johnson. I'm pleased to meet you Richard, your butler will be Ruth." He indicated a girl who would have been no more than twenty years old, her flawless skin and dark hair highlighted her youth in such a way that Richie was suddenly sure that he would indeed enjoy the stay.

"Likewise I'm sure." His eyes never left Ruth. She smiled at him and her perfect white teeth flashed in the half light.

"Your stay here will be everything that you hoped for, I will make sure of that."

The guests rose and followed their respective butlers from the lounge.

"What do you think Beth, will this group be a success?"

"I'm sure that it will, you have chosen, with your usual flair, a group who desperately need help but not from each other, they couldn't be less alike."

"Come, we'll see how they are getting on." He held out his hand and she took it, hand in hand they walked through a door at the rear of the lounge and soon were seated in front of several CCTV monitors. The guests were being shown around their rooms. Michael turned up the volume to Richie's suite in time to hear Ruth. "Mister Johnson, I am your Butler. I am not a part of your fantasy. Our regulations prohibit any interaction other than a working relationship, between guest and butler. Is that understood?"

"Sure." He was not happy.

"Your fantasy is my task, but I will not participate in any way, shape or form. I am here to see that you find happiness in your fantasy not to be a part of it. Firstly you should rest up, would you like to shower before or after you rest?"

"Before, I'll probably need someone to scrub my back for me." He looked at her hopefully.

"I'm sorry sir but I cannot do that, you will however find a loofa towel that will do the job admirably. While you are showering I'll turn your bed down and lay out your clothes for dinner. I'll be back for you in time to take you to dinner."

Richie wasn't pleased that Ruth wasn't going to cater for his every need and meant to raise the issue with Michael after dinner.

Joseph Berman had similar thoughts about Naomi but she soon put those to rest. "I am your butler sir, I have no part to play in your fantasy. I am here to serve you, to make sure that your clothes are ready for you at all times and to run errands for you. There will be a lady along in due course to help you with your fantasy. I suggest that you have a shower and rest up before dinner. I will lay out your clothes for you."

Janice Soderberg looked at Jonah with anticipation, she could see the bulge in his pants and was looking forward to him making love to her. He caught her looking at him and saw the necessity of warning her. "I am your butler madam, the man chosen to fulfil your fantasy is much more manly than I."

"Oh my." She gasped.

"If you would like to shower before you rest I'll lay out you clothes for you, do you have anything in mind to wear?"

"Can I leave that up to you, you know what they wear around here."

"Very well Madam."

When she emerged from her shower she found, not one of the dresses that she had packed but a brightly coloured floral print dress. "This isn't mine." She said to Jonah.

"Indeed it isn't madam, I took the liberty of getting it for you, none of yours seemed appropriate for this evening."

She tried it on, it fitted her perfectly and she had to admit that it was much better than any of hers. "It fits, how . . . ."

"I looked at the labels on your clothes." He left the room to allow her to dress.

In another cabin Cindy too was getting in to a different dress. She had called Reuben into her room. "This isn't mine." She said pointing to her dresses laid out on the bed. They were all of a similar style with high neck-lines designed to hide her figure.

"I took the liberty madam." Reuben said. "You have a very attractive figure, it seemed a pity to hide it."

"But this is cut too low, it's, well it's slutty."

"Madam, trust me it is not, as you so colourfully put it, slutty at all, it shows just enough to be interesting to the right person but not enough to appeal to the wrong person. If you don't like it I'll not be offended."

"No, I didn't mean to offend you." She looked more closely at her reflection in the mirror. "You're right, it's nice, thank you."

In her cabin Julie was having a similar problem. Her wardrobe consisted of nothing other than jeans and button up blouses that she wore every day, whether at home or at work. At work it was almost always covered by a paint covered smock. Her 'uniform' was totally unsuitable for the occasion, but what was she to do?

A tap on the door and Simon entered. "I think that this will be more suitable for you than your own clothes." He held up a brightly coloured floral Mumu dress, one of those long flowing dresses common to the Pacific Islands.

She took it and slipped it over her head, the hem reached just to the top of her feet. She spun around and felt it float about her, it was freedom! "Thank you Simon, thank you so much. I feel wonderful, released, I feel free." She looked at herself in the full-length mirror. She looked different, even though this dress covered her more than her jeans and top it revealed more, it flowed over the twin peaks of her breasts in a way that her blouses could never achieve and when she walked the shape of her hips was highlighted in a way that tight jeans could never do. "Simon."

"Yes Miss?"

"This needs something else, would it be possible to get one of those flowers, hibiscus I think they are, for me to wear behind my ear?" Simon produced a plastic box with a bright red hibiscus bloom resting inside. "You think of everything don't you."

"It is my job to anticipate your needs Miss."

Dinner was a rather strained affair. Try as he might Michael couldn't get them to open up about their expectations of the fantasy vacation. He decided that the best chance to learn more would be in the one on one interviews that he and Beth would shortly conduct. A little more loosening up alcohol and they would be ready.

"Can I have your attention for a moment." One by one they gave it. "We will be discussing with each of you your choice of fantasy and why you chose it. I must prepare you for the possibility that the outcome of this process may not necessarily be what you expect, it will however, regardless of your expectations, be a positive outcome. You may not agree with it at first but in due course you will see that this is so. Beth and I will be speaking to you individually to get a better picture as to your fantasy and how best we can deliver on our promise to you. I will speak to Richard and Joseph while Beth will speak to Janice, Cindy and Julie. Richard, if you would come with me and Janice, you go with Beth, and the rest of you can talk amongst yourselves until you are called."

Richie followed Michael to his office. "Take a seat." Michael indicated a leather lounge. "Now, do you prefer Richard or Richie?"

"Richie, I hate Richard and really hate Dick or Rick."

"I'll remember that. Now, on your application you said that you wanted to live the life of a Sultan with wall to wall harem girls. Now just so that we get this straight, do you want all of the girls to be with you all the time and you choose which one you want to fuck, or would you prefer to be a little more discreet about it and see them one at a time?"

"Whatever. What's the difference?"

"If you were to have them all together and choose one to fuck there could be some jealousy among the others towards your chosen."

"Cool, I've always wanted chicks fighting over me."

"Yes, but if they're fighting they may feel less like helping you achieve your fantasy."

"I get it. One at a time and they all get the chance at me. Do I have a new one for each night?"

"Most assuredly, if that is your wish."

"Cool, when can I start?"

"No time like the present. Ruth is waiting outside to take you to your harem."

Richie almost sprinted out the door. Michael returned to the dining room to get Joseph.

"Please, sit down. Now Joseph you asked for a younger woman just like your wife used to be, is that correct?"

"Yes, that is correct."

"Why do you desire this?"

"I have been married for forty years to Rachel and, while I love my wife, I find her no longer physically attractive. I must admit to you that I am embarrassed, you see, because she no longer excites me I cannot get an erection and I'm embarrassed that she will notice and be offended."

"You don't think that she is offended that you no longer try?"

"I tell her I am too busy to go to bed until much after she does and she is fast asleep when I get to bed."

"I see. And you think that your fantasy of having sex with a younger woman will somehow solve your problem?"

"It will not solve that problem, but it will allow me to dream of what once was and I will no longer be worried by what is. It is about memories."

"Very well, Naomi is waiting outside the door to take you to your fantasy.

Beth asked Janice to take a seat. "Now you asked for a man with a big cock. I assume from that your husband doesn't have one?"

"No, it is tiny."

"What would you call tiny?"

"It would be no more than four inches long."

"Is that when it's hard?"

"What is hard, I don't believe that he has had an erection in five years."

"What do you mean? Was he able to achieve one before then?"

"Oh yes, we had a very active sexual life."

"What do you think changed all of that?"

"It was probably his promotion at work. You would think that when he reached Managerial status his work load would ease off, but not him, he seemed to devote more time to his work and when he gets home he has his dinner and is so tired that all he wants to do is go to bed, we have no family life, no love life."

"Do you resent his lack of interest in you?"

"Wouldn't you? You give up a large part of your life and your career to help him with his and this is how he repays you for what you have done, you bet I resent it. Now all I want to do is to have a monster cock inside my pussy."