Gone With The Winns Ch 02

This is part 2 of a story about a couple who have a YouTube channel, I have spelled their last name differently as not to mess up their search-engine results (as in, this story won't show up if you search for them in Google). If you are curious about them, replace the "i" in the name for a "y".

During the telling of the story the narrator changes a few times, this is made clear by a line of dashes and the name of the new narrator.

Word of warning, English is not my first language; I don't have any editors, just Word spell checker.

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Ana Foxxx:

For those of you that don't know me, I'm an African American pornstar and I've also played a few parts in more mainstream productions. I get a lot of fan mail, which I try to handle myself. This morning I got an intriguing message from a man named John Smith. I check and he is one of my OnlyFans subscribers, he even left a $ 1000 tip for my latest video. I'm not sure if his proposal is real, but I don't see how this could be some kind of scam to get my personal info or money. See for yourself:

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The email from John Smith:

Dear Ana,

This is a long letter from an eccentric fan, please read my entire letter (even when it gets crazy) and think about my proposal.

My name is John Smith and I'm in my late forties. People might call me a loner and they might be right. It's that I don't like to be around other people, but I am rather shy and my self-esteem is not the best. I used to work in an office, but last year I won a LOT of money in a lottery. So, I quit my job and bought a camper to travel. Turns out that traveling on your own is not as fun as I had thought it would be. Sure, you can stop wherever you want, as there is nobody to argue with, but being an introverted person meant that it was hard for me to connect to people. I have always admired people who can strike up a conversation with a complete stranger, it's a skill I don't have. Which meant that most nights I would spend in my RV watching YouTube or porn via my Starlink internet connection.

After another solo visit to a national park, I decided to see if I couldn't use some of my winnings to persuade some fun people to travel with me. So, this is my attempt of trying to find out if I might be able to persuade you and some of your colleagues to join me for an 8-week trip on a catamaran (sailing boat) trip from the Philippines to Australia.

I am subscribed to a YouTube channel of an American couple who live on / travel with a catamaran. The are having a brand-new boat built right now and somehow I have managed to convince them to charter (rent) their boat to me for my trip. The fact that I'll be paying them about 75% of the cost of their new boat might have something to do with it, but I do believe that they are looking forward to the new experiences they will have along the way (they will be the crew during the trip).

I know that an eight-week trip will mean that you can't work during those 2 months, so I plan to compensate your lost income with a $ 75.000 fee. The trip won't happen for another 8 or 9 months from now, their boat won't be ready for a while and then they have to break it in first for a few months. So that might give you some time to create some extra content, that you can post during our trip. Everybody will have to sign a non-disclosure agreement (NDA) about what happens on the trip. This is mainly to project the YouTubers from any backlash with their subscribers / sponsors.

The dress code for everybody on board will be "as minimal as legally possible". Which means that when we are in port or near land, we will probably can get away with wearing skimpy swimwear, maybe something slightly more formal when we have to deal with authorities or when we are getting supplies. As soon as it's possible to get naked, everybody (including the crew) removes all clothes.

As I said, I will be paying you to come on this mostly naked trip, but that does not mean that you have to have sex with me or anybody else on the trip. However, there will be a list of OPTIONAL challenges by which you can earn a cash bonus. And to be clear, some of these challenges will be for you to have sex with one or more of the guests, others will be more mundane like flashing a local.

Of course, I hope that you profession means that you will more at ease with a lot of these challenges then the owners of the boat. Yes, they will also be able to make some extra cash with these challenges, the wife seems to be the more adventurous of the two.

I know that this sounds totally crazy, but please consider my proposal.

I would like to video chat with you to answer any questions you might have and to discuss some things, like the other pornstars I would like to invite. This would take up about an hour of your time, for which I would like to pay you $ 10.000 up front. Please think all of this over for a few days and if you want to speak to me, send me a message so we can setup a date and time.

Regards,

John Smith

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Ana Foxxx:

Like I said, a strange but intriguing plan. Especially because I'm about 99% sure that the YouTubers he mentioned are Jason and Nikki from `Gone with the Winns`, one of my favourite channels!

I decided to send John a quick reply, to let him know that I read his message and needed a few days to think about it, but that it sounded very interesting.

My next step was trying to confirm if Jason and Nikki really are the couple he had convinced to charter their boat to him.

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Nikki Winn:

I can't believe that John mentioned getting my nipples pierced just as I was sure that Jason was going to tell him that we wouldn't accept his proposal. That was 36 hours ago and I've just come back from the piercing studio with bandages over my nipples and all the proper aftercare products.

The look on Jason's face when I asked him what he thought about me getting double diagonal instead of the normal horizontal piercings.

"You mean like an X through each nipple??"

"Yes, I think that might be a cool variation on the norm"

"Really?!? Please tell me you are not messing with me!"

"So, you do like that idea I gather?"

He looked like a 4-year-old on Christmas morning, jumping up and down of joy.

And now I'm relaxing on the bed in our hotel, being waited on hand and foot by my loving husband. The initial pain from getting pierced was intense, but right now it is OK. The 2 Advils I took help to numb the dull pain, so I asked Jason to get me my laptop, I might as well get some work done.

The first thing I do is to check our Patreon messages. There are a few, but nothing new from John. Scanning the subject lines, I see that most are questions about our new boat, but one stands out: `Do you know John Smith? ` For a second my stomach drops, who knows about our crazy charter trip?!? So, I quickly open this message from `FoxxxyLady`:

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The message from Ana to Jason and Nikki:

Hello Jason and Nikki.

If you do know John Smith and have agreed to a charter trip, relax you secret is safe! But I would like it if you could send me a message so we can discuss somethings, as he asked me to be one of his guests.

If you don't know John Smith and his charter plans, please just ignore this message.

All the best from a fan,

Ana

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Nikki Winn:

"All the best from a fan", how is that possible? What are the chances that John invited a pornstar that watches our channel? Unbelievable!

I must have looked flustered, as Jason asked me if I was alright.

"Yeah, I just bumped my arm against my nipple."

Jason does most of the editing of our video's and I tend to answer most messages we get, so he doesn't open our Patreon messages. I figured I would send this Ana a reply, to try and get some more info before I mentioned her to Jason.

"Dear Ana, Nikki here. Your message surprised me, but yes John Smith booked a charter with us. Can you tell me some more about you?"

Just after I had hit send, Jason asked me about what we should do about dinner. We decided on another curry from that place just down the road and then my laptop made a sound to signal that I had a new message:

"Hi Nikki! What a small world. John never mentioned your names, but the description he gave ticked so many boxes, it just had to be you! Like I said I'm a big fan and this means I'm going to accept his offer to go on this trip. You asked about me, just Google Ana Foxxx to see some of my work."

Well, that was a quick response time. Let's fire op Google and get some more info on this Ana. Imagine my surprise when I did not see a picture of a big boobed blond bimbo, but a very beautiful and fit African American woman. Man, she must work out a lot!

Ping! Another new message:

"Of course, Ana Foxxx is my stage name. My hobbies are working out, yoga, hiking and swimming. I have lived near the California coast for most of my life, but I have only been on a boat a few times. I discovered your channel during lockdown, watching travel videos kept me sane."

"That is funny, John said the same thing about finding our channel during lockdown! I'm going to be honest here and admit that my image of a pornstar was a big boobed blonde. I have just seen some photos of you and you were not kidding when you said you liked to work out!"

Ping, another almost instant reply. Even though we were using the Patreon message system, it felt like chatting.

"Yeah, I know what you mean. I started out with some modelling and when somebody suggested I could make a lot of money in porn I just laughed because I didn't think he was serious. But it turns out porn is not just for chicks with enormous boobs."

"We have lived on the road for the last 10 years and getting a decent internet connection was always a problem. Especially in the first few years and if we had a good connection it was used to upload our latest video and communicate for work and with friend. Using it to watch porn was never on my radar. So, I don't know not a lot about porn."

"That's OK, like I said I had to learn about it as well. I'm pretty sure you are in a hotel somewhere in Asia right now. I'll send you a free membership to my site, so fire up your VPN and watch some of my videos."

"You didn't have to do that, but thank you! I'm pretty sure Jason is going to appreciate your gift as well. Oh, our food just arrived, I've got to wrap this up for now."

"OK. Have fun and speak to you later!"

Well, that was an interesting conversation and she seemed like a fun person. This charter is going to be so much fun! I must admit that watching porn is not something that I've done before, but it might be fun. Especially if it gets Jason just as worked up as he was after reading them erotic stories. It will have to wait a few more day though, my nipples hurt too much right now.

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Ana Foxxx:

It was cool to chat with Nikki last night and very cool to confirm that this trip would take place on their new catamaran. I sent a message to John to setup a video call as soon as possible and within the hour we connected the call. On the screen I saw a nervous looking middle-aged man with a fairly fit body (definitely no dad-bod).

"Hello John, nice to meet you!"

"Hello Ana, nice to meet you as well although the fact that you responded so quickly has me worried that this is a thank you, but no thank you conversation?"

"Far from it John. In fact it's an I know you chartered the Winns boat and I'm in as I'm also a big fan of theirs kind of call!"

For a second he looked surprised and then very happy, but still confused.

"How on earth did you find that out?"

"Like I said, I'm also a fan and all the clues where there. So, I followed your lead and contacted them via a Patreon message. I just asked if they knew a John Smith and Nikki got in touch."

"I'll be damned, what a small world. So, you said you are in?"

"Yes, your plan was intriguing from the start, but I wasn't sure if you were for real. Then Nikki confirmed it was real and they are the icing on top. Who else are you going to ask for trip?"

"There is room for 4 passengers, so with you and me confirmed that leaves room for 2 more people. I was kinda hoping to invite Natalie Mars and maybe somebody like Kenzie Reeves or Piper Perri, but you might be able to let me know who might fit the best in such a group?"

"Natalie Mars, cool were friends and inviting a trans person also tells me that you are not a macho asshole."

"So you might be able to convince Natalie to come on this trip? I figured it would be cool to have her on the trip, half the people will have a dick, but Jason and I get to enjoy looking at 4 beautiful ladies."

"I like the way you think, John. And when I quite that line to her she will probably be convinced to sign up for this trip. And then a spinner as the last team member, it's funny Nikki told me she had no idea who I was before she Googled me, but to her a pornstar was a blonde bimbo with big tits. Al the ladies you have picked don't fit that mould."

"You got me there, anything over a C cup is overkill for me."

"You mentioned Kenzie and Piper, I know them both but I have a feeling that Chloe Temple might be a better fit for this trip. Natalie and I know her a lot better and I think she has the right attitude for this trip, she likes to run around naked anywhere she can."

"Really, she would be perfect with all those piercings"

"Are you into piercings John"

Look at him blushing, it's adorable.

"Yeah, that's one of my things. Didn't Nikki tell you about the way she convinced Jason to agree to this charter?"

"No, do tell"

"You better ask her, she can give you the full background on this story."

"OK, I will and I will also talk to Natalie and Chloe. They will probably want a videocall with you after I have told them all about the trip. I'll be in touch later this week."

"Super! Thank you very much. It was lovely meeting you."

"You too, have a nice day."

What a charming man and cool that he wanted my input on who else to ask. This is going to be so much fun.