Billionaire’s Retreat

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Author’s Note- This is my first story. Any feedback would be greatly appreciated!


At age 43, at the height of his business career, billionaire Robert Helm sent out an open casting call for volunteers. Told nothing more than the fact that they would move to live out on his private island in the Caribbean, thousands applied. Applicants faced a lengthy process involving questionnaires, medical examinations, background checks, and interviews. We don’t know how many were accepted, but we estimate about 150 were chosen. Once he made his selections, Robert and his wife Miranda vanished with his wife and the accepted onto his island.

A year later, I was sent on assignment to interview Robert and live on his island. Given the mystery and high media profile of his retreat, the world was fascinated to find out what had happened.

In June, I found myself on a boat bound for Robert’s island. I had no idea what to expect. The crew of my ship didn’t either. They had been told only to drop me off at the one dock on the island, than to depart. I figured that the worst case scenario would be spending a month or two on a billionaire’s playground. So needless to say, I was excited.

When we docked, a beautiful blonde met me at the pier wearing a red bikini under a translucent white dress.

“Hi, Alex?” She shook my hand. “My name is Molly, I’m Robert’s personal assistant. I was told to acquaint you to how we operate on the island before your meeting with Mr. Helm later this evening. Please follow me.”

We made some small talk as we made our way to a building at the end of the dock. I don’t remember much of it- I was distracted by the beautiful white sand beaches, coconut trees, and the swaying ass of the woman leading me. I try to be professional on assignment, but there’s only so much I can do when a skimpy red bikini bottom barely covers an athletic, tanned woman’s rear.

She led me inside, to what looked like an average hotel lobby. She turned to face me. “As part of the negotiations with your magazine, you’ve agreed to live by our rules and procedures, right?” I nodded. She continued, “As a part of that, I’m first going to need to confiscate all of your electronic devices. They’ll be returned to you once you leave.”

I handed her my cell phone, before hesitating with my laptop. “I’ll need something to take notes and write on if I’m going to profile what Robert’s doing here.”

She took the laptop out of my hands anyway. “We’ve put a computer limited to word processing in your room. We’ve also put several pads of paper in your room for note taking.” She hesitated a moment. “We’re also going to need you to undress.”


“Mr. Helm can explain, but I’m afraid it’s island policy that all males are forbidden from wearing clothing.”

I stared at her, looking for signs of a joke. The boat to take me home had already left, and I wasn’t in a position career-wise to refuse an assignment. What the hell. I had already done some weird stuff in my career, urfa escort might as well add this to the list right? Still, there was something disconcerting about stripping in front of a beautiful stranger like Molly. I disrobed and handed her my clothes.

“Great.” She glanced down at my naked body, taking the time to thoroughly inspect my crotch. She clapped her hands excitedly. ” Ooh! You’re not circumcised? We don’t have many of those around the island!”

“Um… really?” It’s hard to make small talk when your cock is on display for the world to see. “Do all guys really walk around here naked all the time?”

She smiled. “Oh yes, it’s very fun. I love watching penises flop and jiggle around, and the variety is pretty fun.” She gave my crotch a sly glance. “And they’re fun when they’re hard too.”

Just hearing her talk about her love of penises was enough to get me semi-hard. I covered my crotch with my hands, mortified. She swatted my hands away. “Oh don’t be shy. Didn’t I just say they’re fun to look at? Besides, you’re done with clothes for a while. Better get used to it!” She motioned for me to follow her, “Come with me, I’ll take you to meet Robert.”

I glanced down at my still-hard penis. “Um, Molly, do you mind giving me a momen-“

“Alex!” In walked Robert Helm himself, also completely naked. This was a man I was used to seeing wearing the finest suits on the cover of Forbes. It was extremely disconcerting to see him standing before me, stark naked. Molly reacted to none of this, as if seeing her billionaire boss naked was the most normal thing in the world.

Robert shook my hand and grinned at me. “I see Molly’s gotten you into the spirit of the island.”

I managed a weak chuckle, hoping my erection would subside quickly. Molly’s persistent stare wasn’t helping, however. Robert motioned to me. “Come with me, Alex. I’ll take you to meet my partner Miranda. She’s waiting for us in my office.”

He led me down a hallway into his office, where an older woman of about forty was sitting on a couch. She was wearing a two-piece charcoal dress that showed a firm midriff despite her age. She smiled and rose gracefully as we entered.

“You must be Alex.” She reached forward to give me a handshake. While maintaining eye contact and a smile, she reached in and instead gave my hard-on a gentle squeeze and a few strokes. “It’s great to meet you”, she continued while stroking me. “Uncircumcised, how fun. I’m Miranda.”

I looked at Robert, dumfounded and horrified. While scrambling to come up with some excuse for what just happened, he laughed at my obvious consternation. “As you can see, we’ve changed some of the social customs as a part of what we’re doing here. Have a seat, we can talk all about it.”

He gestured to a chair across from the couch where he sat next to Miranda. Taking the initiative and excited finally for the answers, I leaned forward. “So, what’s going on here? What’s…?” I shrugged, lost for words. escort urfa Again, it’s hard to be articulate with a full-blown erection in front of two strangers.

Robert gave an understanding smile. “For centuries now, us technologists have been trying to make the average person’s life better through new gadgets and toys. For most of my career this consumed me. And I was good at it too, it’s how I made my fortune. Over the last couple of years however, a nagging thought grew in my head. I think the world’s problems don’t stem from immature technology, but rather from our social norms and customs. I own an island- a perfect place to experiment with culture. I have the financial means to do whatever I like. Why not try to solve these problems?”

“So everything here is part of a social experiment?”

Robert nodded. “And it’s been going pretty well so far. Nearly all the people here are pretty content with their lives. Though they now have the option, none have chosen to leave here and go back to their previous lives.”

Things, to a certain degree at least, were starting to make sense. “So why do men have to be naked?”

Robert gave a wry smile. “I thought you would ask about that. One of our goals here is to build social unity. When men and women typically get together to discuss an issue, men often dominate the conversation because of their egos. Demanding men to be naked while allowing women to wear whatever they want changes the dynamic by forcing humility on the men. It ensures the best idea is heard.”

“Plus,” Miranda added with a playful smile, “it’s very fun. Cocks everywhere!” She leaned over and began fondling Robert, handling his balls before slowly stroking his shaft. “It’s great to get a show every time you walk outside.”

“People here are also very open about love and physical intimacy.” Robert said, noting my stare. “Forcing people to hide their affection is to hide something that we all should celebrate, not shame. It’s healthier for everyone.”

“Mmmhmm”, Miranda said in agreement, licking her lips. She leaned over and took the head of Robert’s cock in her mouth, slowly sucking on it while stroking his shaft.

“We also don’t have a concept of marriage here,” Robert continued. “People are free to take as many lovers as they like and leave them whenever they like.”

Miranda began to suck with more passion, taking the entire length of his shaft into her mouth. I stared at her performance. “How do you deal with issues of jealously?”

Robert’s words became more disjointed as Miranda began to stroke his cock faster. “Well… you have to take things on a… ahhh… case by case… ahh… basis. Some people want many lovers… some people only want one. Oh fuck.”

Miranda left the couch and knelt in front of Robert with her back to me. Pumping him faster and faster, Robert climaxed, send white ropes of cum shooting into his partner’s waiting mouth. She gave a happy moan as he came, as if urging him urfa escort bayan to shoot as much as he could. He finished, then relaxed and gave a laugh. “Thanks for that, dear. What a pro, not even a drop spilled!”

Miranda smiled back, showing Robert and I her mouthful. She winked at me then swallowed, and then gave Robert a kiss. He looked back at me. “It’s getting late, and I’m sure you’re tired from your travel. Follow me, I’ll take you back to Molly.”

He took Miranda by the hand, and led her and I back down the hallway to the reception area, his cock now wilting and now glistening with Miranda’s saliva. As we walked, I heard some faint moaning that grew louder and louder as we approached the reception area. “What’s that noise…?” The question died in my throat as I looked in.

Facing us, Molly was bent over the reception desk. Though she was still clothed as I saw her before, a naked man was pumping into her from behind. She was moaning in ecstasy, her eyes unfocused and glazed over.

“Oooh, how delightful!” Miranda said. While enjoying the performance, she unconsciously reached down and began playing with Robert’s cock again.

Robert gave a bemused smile. “Well, I was going to have Molly here show you to your room”, he said to me, “but I guess she’s somewhat occupied at the moment.”

The man began pounding faster. Her moans grew louder and took a higher and higher pitch. The sounds of flesh slapping together grew louder, and her tits, still held behind the red bikini, began to bounce more and more.

“Molly?” Robert called over the noise. “I’m going to take Alex here to the kitchen. Can you please join us when you’re finished?”

Molly managed a nod.

Miranda let go of Robert’s cock and playfully squeezed his ass. “You go, dear. I want to stay and watch the show.”

Robert grinned. He turned and led me down another hallway into the kitchen. “Can I get you a drink?”

From the reception area, I could hear Molly’s moans getting louder and louder.

“Um, sure, I’ll take a water.”

Robert walked to the cabinet, grabbed me a glass, and began filling it up. Molly’s moans grew louder and louder until they peaked in a final yell. Robert handed me the glass and winked. “I’m sure you’ll enjoy your stay here. It’s not yet paradise, but we’re working on it.”

Molly walked into the kitchen, breathing hard and slightly disheveled. “Molly, could you lead Alex here to his room?” He glanced down. “And would you mind cleaning up a bit, dear? You’re dripping.”

I followed his gaze. Cum was sliding down her thighs onto the floor.

She managed another tired nod, then turned and led me out of the kitchen into the hallway. She didn’t try to make any conversation as we walked. I wouldn’t have been able to anyway. I could see the white stains on her bikini bottom. As her hips shook with each step, cum would slide out from the red triangle covering her ass and drip down to the floor. She led me to my room, then turned and left quickly leaving me a white spot in the carpet by my door to remember her by. I’m sure she was off to find some cleaning supplies.

It was incredibly tough to not masturbate that night, but given the events of the day I was fairly sure I could have some fun of my own soon. I fell asleep, excited about what tomorrow would bring.

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