Billionaire Island Read online

  I couldn’t believe it. I had been invited to spend a year on an island, working for my company from the comfort of my own beach-front property. My salary was going to be doubled, and all my expenses were bought and paid for. As a 24 year old male, fresh into the technology sector, this was a dream come true. The company that hired me right out of college was a decent start up in my hometown, and we had just been scooped up by a Fortune 500 technology company. The CEO had picked me out for my productive numbers, and I basically won a sweepstakes to “work remotely” on a “special project”. The special project turned out to be an incredible vacation.

  I was in a private jet, being flown directly to the island, and had my own personal flight attendant - a sexy, buxom woman named Tatiana - who smiled at me over her ample cleavage. I was going to meet the CEO himself, William Dart, once I landed.

  “Mr. Hill, was there anything I could do for you?” Tatiana said with her big, bright smile. I smiled in thanks, and held up my hand in refusal. She really was an attractive woman, and dressed almost borderline slutty (inappropriate) for a flight attendant. Her teal dress was maybe too short by an inch or two, and her dress had a plunging neckline, with her breasts virtually popping out. The perks of being a billionaire; I could only shake my head in wonder. The wealthy lived in a different world than everyone else.

  “We will be landing shortly. Please put your seatbelt back on,” came the pilot's voice over the intercom. I followed the instructions and stared out the window. A fairly large Island lay a ahead, and from our height, I was able to make out a few shiny structures. It looked like Mr. Dart had established his Island quite well in the last few years. We touched down on the runway and I disembarked to find a handsome woman in her early 50’s wearing a pantsuit waiting for me in a golf cart.

  “You must be Mr. Hill. It's a pleasure to meet you. My name is Joanna. I've been instructed to take you to Mr. Dart,” the woman said with a smile and a firm handshake.

  “I'm meeting Mr. Dart already?” I asked confusedly. I assumed I'd have a chance to freshen up first.

  “Oh yes. He's very excited to meet you,” Joanna said with a warm smile. I sat back, elated with the VIP treatment, but there was a nagging feeling of doubt and nervousness in the back of my mind.

  The rest of the golf cart ride went by in silence mostly, as I was taking in the sights and sounds of the island. We went down a small paved road after leaving the runway, which was lined with lush, beautiful trees. The foliage was thick enough that I wasn't able to see the sky beyond the trees. I could smell the distinct scent of salt water, and everything felt clean and fresh. I felt like I was in paradise.

  The golf cart stopping jolted me out of my reverie. I thanked Joanna, shook her hand again, and looked at the place she had dropped me off at. It was a small, square house with darkened windows. It did not look like anything a billionaire would live in.

  “This looks like a really bad fucking idea…” i muttered to myself. Just my luck to be on a strange Island with no way off it, abandoned by myself to a shady house.

  Just as I was about to start walking back the way Joanna and I had come, a woman stepped out of the front door. Even from the distance I was at, she was clearly gorgeous. Tall, brunette, with a beaming smile, the goddess was dressed in a pink dress and heels. She was waving me over, so I figured why the hell not?

  “Hi, my name is Diana. I'm so sorry I wasn't at the door to greet you. Joanna called ahead, but I was cleaning up. Mr. Dart is just upstairs. If you would follow me Mr. Hill?” i was absolutely floored. Yeah, this seemed more like something a billionaire would do.

  I followed her into a house that looked nothing at all like the impression it gave off from the outside. Inside, there were exquisite and very tasteful leather couches, a top of the line wall mounted TV, ornate solid wood tables, and everything practically shone. The walls were made of wood and gave the living area a homely cottage feeling, while the open concept kitchen and dining area were more of a modern design.

  “Right this way sir,” Diana beckoned from the foot of the stairs. “Mr. Dart is upstairs.”

  I followed her up the stairs, and watched her incredible bubble butt sashay in front of me. Her dress clung skin tight to her body, and rode up ever so slightly. I guess this must be one of the many perks of having more money than God.

  We walked down a short hallway and Diana opened up a door for me. I entered into a small office, a couch, wall mounted TV over a small fireplace, and a computer table. Seated at the computer table in a high backed executive chair was a darkly handsome man with a sharp nose, and a mouth that seemed to curve up at the corners, like he was in on a joke nobody else was aware of. His coiffed hair was boyishly mussed at the front, giving him an air of aloofness. The man's dark eyes glittered with a hunger that immediately put me on edge, and was at odds with his otherwise friendly appearance.

  “Hello Mr. Hill,” the man said in a soft, rich voice. He stood and extended a long fingered hand to me, his grip strong in the handshake. “Please, grab a seat. My name is William Dart. Thank you for accepting my invitation.”

  I was taken aback. This man wasn't more than a few years older than me; how was he able to have run a Fortune 500 company for the last 30 years? He must have been in diapers when it first started.

  “I can see that you're a little taken aback. My family and I are very private people, as I'm sure you've noticed. I suppose I should say that I am William Jr., but everyone calls me Bill. My father is the man who started the company,” Bill said with a small smile. He was amused; playing with me and my obvious lack of knowledge. I needed to pull myself together and not be caught unawares.

  “Oh, yes, I had no idea. Sorry, I didn't mean to be rude,” I said meekly. I didn't think I was that transparent. Bill gestured to a seat in front of the desk, and I sat down.

  “Now, the job title that was picked out for you was that of ‘Coordinator’. I would like to lay out exactly why your job is very special, and what it will entail. But first, I believe there is a very important matter to discuss.” There was dead silence in the room as Mr. Dart regarded me intensely with his dark eyes. “This island that we're on currently was bought by my father over 40 years ago. He started the program that I would like to perfect in my lifetime, and I want you to help me.”

  This had to be a joke. I just met this guy! He knew nothing about me, yet, he was offering me a chance to be employed for life.

  “I don't mean any disrespect here sir, but you literally just met me. What could I possibly help you with?” I asked him, honestly concerned that he had called the wrong Matthew Hill into this island paradise.

  “Matthew, I would like to be absolutely honest with you, and for that to happen, I need you to sign an NDA about what you see and hear in this room. Can I count on you to do that?” Mr. Dart was looking at me intensely over his steepled fingers. It was unnerving.

  “Uh, yeah sure. I can do that,” I said uncertainly. Immediately, the darkly handsome man shifted a folder over to my side of the table. I opened it, and inside was a fairly standard Non Disclosure Agreement, built to protect anything and everything that was said or seen while on the island. I had no problem with signing something standard, so I signed it and shoved the folder back over.

  Mr. Dart inspected my signatures, and then looked at me gravely. “Mr. Hill, you know that my company owns a fairly large portion of many data mining companies, some search engines, and that these companies offer me a lot of power and information. I have been using some of this metadata for my own personal use. Some of this, includes keeping track of any IP addresses that have certain...search patterns. You were one such search pattern, and upon learning that, I had some of my people within the company hire you on. I monitored your prog
ress within the company, and upon seeing that you were everything that I had hoped you were, I decided to put forth my invitation to join me here.”

  I was stunned. If my jaw could unhinge enough to hit the floor, it would have. This guy just copped to breaking an INSANE number of laws, and had just told me he manipulated my adult life for his own gain. I wasn’t sure whether I should be livid, or whether I should just walk out and blow the whistle on him, NDA be damned.

  “What-, what are you talking about?” My throat felt dry. I was stunned. I felt like I’d been punched in the gut

  “Specifically? I’m talking about your search history. Your likes and dislikes. Your health concerns you like to search up. The video games you like to play, the movies you watch, the pictures you upload, your social media. I watched it all once you caught the attention of my algorithms. But mostly, I watched your porn tastes,” Mr. Dart had no humour to his voice, and it scared me. I made a croaking sound, but no words came to mind. What the hell did I get myself into?

  “Mr. Hill, you fascinate me. I saw how you were around everybody in your life. I also saw that you like your women in a special way. The reason that you caught my eye, Mr. Hill, is because I also see things your way.”

  Now I was sure this guy was just fucking with me. He called me to an island and offered me a job that was going to pay me so far and above what I was worth because we shared PORN tastes?? No fucking chance. But this guy was a privacy invading megalomaniac who gave exactly zero shits about what the whole might of the US government could do to him if they were ever to find out what an abuse of power he had committed, and I wasn’t about to tell him how I felt about it when I had no way off the island.

  “I can see you’re skeptical. The project I embarked on, the one that I wanted to finish that my father started, is to create a special kind of society. Everyone who lives on this island has been invited by me, and everyone who has seen the vision of what I offer has always chosen to stay,” Mr. Dart stood up, and loomed above me. He was a tall, athletically built guy, but leaned slightly toward the skinny, lanky side of things.

  “If you still choose to accept this job, the house we are in currently will be yours. I would like to give you a tour, if you wouldn’t mind? It will make things more clear for you,” Mr. Dart walked to the door and opened it for me, and I followed him out into the hall.

  He turned toward the only other door in the hallway, and opened it for me. I walked in, and saw Diana standing there, gorgeous in all her glory. What blew me away though, was what she was wearing. Gone was the sexy pink dress, and now she was wearing a black micro mini skirt, and a fishnet strapless bandeau top. She was in 6 inch clear plastic heels, reminiscent of a stripper. She did a slow turn for me, and bent over to show me that she had a butt plug inserted into her ass, with no panties on.

  Despite the incredibly slutty show, she still looked very pretty. It was amazing how my brain was still able to process that thought, considering how the rest of me was frozen in shock.

  “You see, Matthew, this is the society I wanted to create. Diana has volunteered to be your personal...assistant. Everyone on this island wants to embrace their sexuality, and not let sex be a taboo subject to broach anymore. I have allowed everyone to do this, man or woman, and in exchange for this freedom, they are all able to contribute to society. We are nearly fully self-sufficient. Volunteers farm, and cook, and clean, and everyone pulls their weight in some way, shape, or form. In exchange, every single person is able to live out their fantasies,” Mr. Dart said matter-of-factly as Diana straightened and turned to look at me.

  I was floored. I had no idea what the hell was going through my head, but the only rational thought I was able to get out was, “So...what do you need me to do?”

  “Matthew, I need your help to run this place. You have created some incredible processes for my firm off-island. I want you to help maintain and update tasks that need getting done to make sure this society can be fully self-sustaining. It will be boring work, but you will have full amenities to the rest of the island, and all the facilities are available to everyone. Can I assume that you would like to work here?”

  I nodded meekly.

  “Good. I will leave you to it then. In the study we just left, you will find a laptop in the drawer, as well as an envelope. The envelope contains a contract, with an electronic copy on the laptop. I would advise you to read it over, as it contains the terms of your employment here. I know Diana will be more than happy to assist you with anything you need. The phone on the desk has my phone number saved onto it, so just call or text me anytime if you need to ask me anything. I have some business to attend to off-island, but thank you, and I look forward to working with you over the next year.” And with that, Mr. Dart turned on his heel and walked out the door, leaving me with the most beautiful woman I had ever met in my life, who was scantily clad and practically naked for me.

  “Uhh, so, umm….” I was at a total loss for words.

  “Don't worry,” Diana said with a friendly smile. “I realize this may be coming on a little strong, but I've actually been really excited to meet you, and totally forgot to take your feelings into account. I'm sorry for that. How about we start from the beginning again?”

  I nodded, my mouth hanging open.

  Diana held out her hand. “Hello, my name is Diana Masterson. It's a pleasure to meet you.”

  “Matt.” I gave myself a little shake of the head. I had to get my shit together. For fucks sake, get a hold of yourself! And close your mouth before you catch a fly! I refocused. “My name's Matthew Hill. Everyone just calls me Matt though.” I just had to treat this like a business meeting. Ignore the fact that she had a sex toy stuck inside of her, and she had put herself at my mercy mere minutes ago.

  “Well then, Matt. I believe our boss, Mr. Dart has instructed you to take a look at some paperwork and to sign a contract before starting your term here? If you could follow me please,” Diana said. She was all business too, and I sincerely did appreciate the effort she was putting into making this conversation as normal as possible for me.

  Naturally, all that went out the window the second she took the lead, as I could now see her luscious ass, half covered by the skirt, and the butt plug showed itself in flashes. I felt my cock tent my pants again.

  Once we were back in the room, Diana had me sit down at the desk. Pulling out the laptop and the papers, she now hovered over my shoulder, out of view. That made things much easier.

  “So pretty much, the contract is essentially just a rundown of what this island allows and what isn't really allowed. It's a lot of legalese, but it's mostly there to protect you, Mr. Dart, and the other residents of the island,” she began as I flipped through the sheaf of paper. “Basically, any sexual fantasy you might have is allowed here. People have various fetishes, and there's so many kinks to explore. If you have a problem with doing something, simply saying that you aren't interested is going to be fine. If you'd like to explore something new, finding someone who's already into it or asking a partner to join you is totally ok. Truthfully, the primary kink around here is exhibitionism. You might see some bondage happen right out in the open. It's a pretty huge departure from what the main land is like.”

  As I flipped through the pages, paying close attention to what Diana was saying, I realized that the contract prevented anyone from violating consent, and everyone could move at their own pace.

  “So how do we know that everyone is OK with the general tone of the sex play on the island?” I asked her.

  “Good question. Remember how Mr. Dart said he used his algorithm to pinpoint people all over the world to get specific types of people out here? Well, that algorithm takes into account the fact that people are all mostly going to be into the lifestyle on this island, and also that nobody feels awkward for too long. It’s surprisingly adept at gathering people who have the same general personality mold,” she explained patiently.

  I looked at her, and a thought occurred to me. “So,
wait. How come you’re here?”

  Diana smiled shyly at me. “Umm...actually, it’s really just because Mr. Dart knew that I really wanted to be a live-in personal slut for someone..and when he told me that there was a new guy coming who was kind of into that as well, I thought it would be worth a shot to see if I could volunteer. I hope that doesn’t come on too strong, though!” She looked at me wide-eyed, a blush creeping up her cheeks.

  I couldn’t help but laugh. She looked incredibly cute like that.

  “Hey, don’t worry about it. Honestly, I’m kinda starting to warm up to the idea of this place, but before we jump into anything like that, let’s see if we can get along first, alright?” I said, attempting to put her at ease.

  The attempt worked, Diana relaxed visibly. She was smiling, and everything felt normal for me at least. I just had to continue pretending she was fully clothed. I turned back to the contract in front of me, picked up the pen, and signed on the dotted line. I was willing to take the plunge into this absolutely crazy world. It was like a perverted dream that was every guilty pleasure and fantasy of mine. And hell, it was a once in a lifetime opportunity. I couldn’t let this get passed up.