Celebrity Sex Stories

Chapter 2: Farewell to the Winns

Who else can join the excursion?

Spankmasters
Jun 7, 2024
8 min read
compersionpiercingsGone with the Winns Ch. 02
Gone with the Winns Ch. 02
Gone with the Winns Ch. 02

Chapter 2: Farewell to the Winns

Ana Foxxx speaks about herself, being an African American pornstar who has appeared in mainstream productions too. She is quite busy, receiving fan mail daily. One message received today is from a subscriber named John Smith, who gave her a $1000 tip on her latest video. He proposes something unusual, and she spends the rest of her story sharing his email.

John Smith, an introverted man in his late forties, shares his story. Previously, he worked in an office but after winning a lottery, he quit his job and lives in a camper van, traveling. He desires company more than anything but his introverted personality prevents him from mingling. He stumbles into a special YouTube channel that runs on a boat and he reaches out to Ana.

He asks her if she and her colleagues would consider joining him for an eight-week-long trip from the Philippines to Australia. He intends to pay for their travel and their lost income (assuming he'd pay them a good fee). The boat's owners haven't started using their new boat yet, so this might be a good opportunity. He hopes this could be fun for Ana as much as him. The dress code is "as minimal as legally allowed", which could mean being naked after in port or near land. There would be optional challenges for extra cash, but these challenges do not necessarily mean sex. It's possible they might challenge each other in different ways. He hopes, because of her profession, she'd feel more at ease with these challenges. He's aware the proposal sounds crazy.

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Ana Foxxx:

Let me tell you a story about a man called John Smith, a man who finds my job... delightful. He's a 40-something guy, shy and introverted. Yet he's rich now, thanks to a lucky lottery win. Owing to this, he's functioning as a full-time camper van dweller. This lifestyle didn't turn out as planned. While it's great he can stop wherever he wants, the requirement to be always on the road makes him lonely. More so, being a shy person, gathering people for some fun is a pain. He spends his nights mainly watching YouTube or browsing for porn.

To change things, he decides to fund a new adventure. Boats always excited him. So, he found an American couple with their own boat-living YouTube channel. They agreed to rent him their new boat and they'll be part of the crew on his journey. Their current boat's not ready yet, and it needs breaking in, so he has ample time to spice things up. His goal is to fill the boat with fun company and possibly, enjoy some jokes along the way. Now, about Ana that's in this story: I'm a pornstar.

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John Smith's proposal to Ana:

To Ana Foxxx:

I'm an eccentric fan reaching out with a proposal. Yes, I'm strange, but please take time to consider.

I'm John Smith, mid-40s, spent my life in a cubicle, but now I have millions, so I traded my desk to live in a camper. But even then, I couldn't find peace in seclusion. I like talking to people, it's a helpful skill I lack. I hit upon an idea of financing an interesting trip throughout the wildness: 8 weeks in a catamaran boat, sailing from the Philippines to Australia. I found a couple with a YouTube channel inside their catamaran. To my surprise, they're willing to rent it to me; hell, cash may have played a role. Incidentally, they are thrilled about the experience too.

I realize an 8-week journey will take away time from your job, so to ease that sting, I've made a 'strong' financial offer. Their new boat won't be ready for a while; time enough to create and post content in the meantime. They all must sign a confidentiality agreement to protect themselves from words reaching public eyes.

While I like the idea of a no-clothes dress code when near land, things might be less trivial when out of sight of civilization. During the trip, people could wear skimpy swimwear or slightly more sophisticated attire when interacting with local figures or nabbing supplies. Your unique profession might help you feel embroiled in this scenario more acclimated than the travelers.

Please consider this fantastical offer. Other travelers have a chance to potentially earn extra cash by coming to terms with different sexual challenges. Believe me, partial nudity, even semi-public skin, is not my first preference... Will I need to do this? No. Your talent can help boost up my will.

Crazy but true, John Smith. Can we arrange a meet for more detail?

I'm interested in talking with you through a video chat to respond to any potential questions and discuss other pornstars I wish to invite. This would consume approximately an hour of your time, for which I'm willing to pay you $10,000 upfront. Please take a few days to think about it, and if you're keen on conversing with me, reach out so we can arrange a meeting date and time.

Best,

John Smith

Ana Foxxx:

It's a strange yet captivating strategy. I'm 99% certain the YouTubers he referred to are Jason and Nikki from "Gone with the Winns," one of my preferred channels!

I decided to send John a quick response, letting him know I received his message and needed a few days to consider it, but it sounds incredibly intriguing.

Next, I tried to verify if Jason and Nikki were really the couple who had agreed to his plan.

Nikki Winn:

I can't fathom that John referred to my piercings in his message just as I was convinced that Jason would inform him we wouldn't accept his proposition. That was 36 hours ago, and I have just returned from the piercing studio, with bandages over my nipples and all the necessary aftercare products.

Jason's expression when I proposed getting double-diagonal piercings instead of horizontal ones.

"You mean like an X through each nipple?"

"Yes, I think that could be an intriguing spin on the norm."

"Really?!? Do you really like that idea?"

He seemed like a 4-year-old on Christmas morning, bouncing with pleasure.

Now I'm resting on the bed in our hotel, being taken care of by my adoring spouse. The initial pain from the piercings was severe, but now it's manageable, with the two Advils I took helping to dull the dull pain, so I persuaded Jason to bring me my laptop so I could do some work.

The first thing I did was check our Patreon messages. There were a few, but nothing new from John. Scanning the subject lines, I spotted one that stood out: "Do you know John Smith?" Was my stomach dropping at the thought that John mentioned our wild charter trip?!? So, I opened this message from "FoxxxyLady":

The message from Ana to Jason and Nikki:

Hey Jason and Nikki.

If you do know John Smith and have agreed to his charter voyage, fear not - your secret will be safe! However, I'd like to discuss some topics with you since he asked me to be one of his guests.

If you're not acquainted with John Smith or his boating plans, just disregard this message.

All the best from a fan,

Ana

Nikki Winn:

"All the best from a fan"! How could that be possible?!? What are the odds that John invited a pornstar who watches our channel? Unbelievable!

I must've seemed startled, as Jason asked how I was doing.

"I just bumped my arm against my nipple."

Jason manages the majority of the editing of our videos, while I typically handle our messages, so he hasn't seen our Patreon messages. I decided to send Ana a reply to gather additional information before I mentioned her to Jason.

"Dear Ana, Nicki here. Your message astounded me, but yes, John Smith booked a charter with us. Can you divulge more details about you?"

On the verge of clicking "send," Jason inquired what we should have for dinner. We agreed on a curry from the restaurant down the road. My computer then indicated a new message:

"Hi Nikki! What a small world. John never disclosed your names, but the description he provided corresponded to you! Like I said, I'm a fervent fan and I plan on agreeing to his offer to join the trip. You inquired about me; simply Google "Ana Foxxx" to see some of my work."

This was a prompt response. I searched "Ana Foxxx" on Google and was stunned to discover a gorgeous, agile African American woman. She must engage in a great deal of physical activity!

Bing! I had a new message:

"Of course, Ana Foxxx is my stage name. My interests include working out, yoga, hiking, and swimming. I've resided near the California shore for the majority of my life, but I've only been on a boat a few times. I came across your channel throughout lockdown. Watching travel videos aided me immensely."

Ping. Another prompt response appeared on the screen. Despite using Patreon's message system for communication, it felt like chatting.

"Yes, I understand what you mean," Nikki responded. "I initially started with some modeling work. When someone mentioned I could earn a significant income in the porn industry, I dismissed the idea because I didn't think he was serious. Little did I know, porn isn't just for women with large breasts."

"For years, we've lived on the road, and getting a reliable internet connection was always a hurdle. In the initial years, if we had a strong connection, it was used to upload our most recent video and to communicate for work and with friends. Watching porn was never my concern."

"That's okay, just as I stated, I had to learn about it as well. I'm convinced you're in a hotel somewhere in Asia right now. I'll offer you a free pass to my website, so turn on your VPN and check out some of my performances."

"Thank you so much for that! I'm certain Jason will enjoy it as well. By the way, our meal has just arrived. I need to wrap this up for now."

"Alright. Have fun and I'll talk to you later!"

Interesting conversation indeed. She seemed like an amusing person. I can't help but feel that viewing porn is something I've not done in the past. Although it might be intriguing, it'll have to wait a few more days until my nipples stop hurting.

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Ana Foxxx:

The conversation I shared with Nikki last night was thrilling and revealed she was a funny character. I quickly contacted John on a video call. Viewing John's anxious yet fit figure on the screen, I exclaimed, "Hello John, nice meeting you!"

"Hello Ana, glad to meet you... but the fact that you answered so promptly makes me question if this will be a thank you but no thank you conversation," John replied.

"Absolutely not, John! This is a confirmation that I'm in on your plan to charter the Winns boat. It sounded intriguing at first, but I wasn't quite sure if it was genuine. Fortunately, Nikki assured me of its authenticity, giving me complete confidence."

"I'm thrilled you're aboard, Ana. I'm left with only two more spots for passengers. I was considering inviting Natalie Mars, Kenzie Reeves, or possibly Piper Perri. Could you discern who would fit perfectly into this group?"

"Natalie and I are friends; she just might accept your invitation. As for you, you seem to have a preference for women with body piercings."

John blushed at this with a bashful grin, apparently amused by the suggestion.

"I do like piercings, and caring for them is something I do often. It seems Nikki didn't know who I was before she searched about me online. She had a stereotype that a pornstar is nothing but a platinum blonde with enormous breasts."

"Your selection of Natalie, Kenzie, and Piper dispels that myth, as these ladies don't match the usual stereotypical standards."

"You're absolutely right. I'll avoid selecting those with large breasts."

"I'd suggest Chloe Temple for the trip. She's a close friend of Natalie and me. I sense she'd be a great fit for this adventure as she enjoys running around naked whenever she can."

"With all those piercings, she really seems fitting."

"Indeed, Julian's story about convincing Jason to charter the boat should provide you with more insight. It's good to know you appreciate her!"

"Do you think you could convince Natalie to join this experience? I'm looking forward to being surrounded by four beautiful, naked women."

"I feel the same, ganging up on Jason and Natalie will be incredibly entertaining. I'll stay in touch about the trip later this week."

We both bid goodbye, and John said, "Super! Thank you very much. It was great speaking to you."

It's amazing how charming he is and how impressive it is that he wants my opinion on who else to invite. This is sure to be a great time.

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