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Note: All characters are 18+ and fictitious. Any names or descriptions resembling actual people is purely coincidental.

§

It was a bittersweet day when they reached St. Thomas. They tied up at a marina on the southwest part of the island, and went out to a very nice restaurant for dinner right there by the docks. As they walked back together in the dark, Chloe had an arm around Dave and the other around Rick, their arms around her in turn, and she told them how much she enjoyed being their Yeoman, and Pirate Whore, and how much fun it was to learn all they taught her about sex. They would catch a cab to the airport in the morning, so she promised to spend the night with both of them just this once, so they could give her one more lesson before leaving.

When she arrived in Dave’s cabin to find him and Rick waiting for her, she handed them each a canvas lanyard, her blushing smile turning her cheeks red. Then she laughed when they each revealed the lanyards they had taken from the locker too.

It was more scary than Chloe had expected, to be tied down… but also much more exciting than she expected too. They had her wrists and ankles wrapped, her limbs pulled wide to either side, leaving her completely vulnerable. The lanyards ran under the cushions and tied together, so she couldn’t move more than a few inches on any of her limbs.

The Rick and Dave took turns fucking her. They didn’t let themselves cum, just fucked her until they were close, then switched out for the other to take over. Only after more than an hour of this did they indulge themselves with cumming in her tight little sex.

Chloe was reeling from her third climax when they untied her, flipped her over, tied her down again, and spent a little time lightly spanking her ass to make her yelp and giggle. The more they did it, the more turned on she became. And when one finger fucked her pussy while the other spanked her round cheeks, she was put through another lingering orgasm.

While she was still twitching, scented oil got poured over her rear, and a hard cock swam through it to slide up her ass. They switched out as they had before, taking turns sodomizing her for almost another hour.

For the finale, they left her tied face down, and Dave squirmed his way under until he could stick his cock up into her pussy. Then Rick mounted her ass, and they fucked the poor teen into two more orgasms before filling her at both ends with their cum.

Chloe lay there, panting and spent, waiting to be released, but they didn’t. They had decided they couldn’t waste any time with sleep on this last night, and would just sleep on the flight later. This meant they were staying up all night playing with their Yeoman. She got tied up in various ways as they finger fucked her, spanked her ass, and eventually managed to get hard again so they could fuck her just before sunrise.

When the first light of the morning came, Chloe was feeling sore and sticky when the door to the cabin opened. Mike ushered out Dave and Rick to get ready for their flight, but he left Chloe tied up where they left her, on her knees with hands behind her back, and viciously fucked her pussy and ass before releasing her. Chloe was a little shocked at how much more aggressive Uncle Mike was with her. He really seemed to enjoy pounding her in that helpless state, almost punishingly, spanking her butt and yanking back hard on her hair. But, as aggressive and forceful as he was, Chloe had the most intense orgasm of the night on his cock as he came in her tight ass.

She had to lay there on the cum covered sheets until Rick and Dave were done getting cleaned up before she was allowed to take a shower. Then she got dressed in the miniskirt and crop top her Uncle wanted her in, and they went with them to the airport.

Chloe had a tearful goodbye with her two shipmates, and they promised to come back soon for another ‘Chloe Cruise.’ She loved that idea, and made them promise that, even if they had girlfriends, they would still find a way to come back and teach her some more. Or even better, they could bring their girlfriends if they wanted to teach her some things as well.

After the airport, they spent the day running errands to get the Sea Nymph ready to charter. Registration transfers, taxes, a PO box, and various other requirements, and after a full day of this, they still weren’t even close to done. More appointments had to be made for the days to follow, and it seemed they would still have to wait for the bureaucratic machine to slowly turn.

§

That night, they relaxed on the deck, missing Dave’s cooking after Chloe’s attempt to make them dinner, and discussed how they would break the news to Diane, Chloe’s mother. That was a conversation neither of them looked forward to.

Chloe fixed her hair, picked out one of her less revealing one piece bathing suits, and joined Uncle Mike in the salon. “Well… ready?” she asked.

Uncle Mike shook his head. “Nope, but let’s do it.”

Chloe called gemlik escort her mom.

“It’s my baby girl!” Diane cheered when she saw Chloe’s face. “Oh, look at you! You’re so tan! I’m jealous!”

Chloe laughed. “Hi Mom!”

“Diane.” Mike said, leaning into the frame next to Chloe. “You look good.” And she did. He could easily see where Chloe got her good looks. She was 43, but could easily pass for mid 30’s, and had the same beautiful smile and bright blue eyes her daughter inherited. She wasn’t quite as small in the breast department, and had a somewhat broader build all around, though still on the petite side. And, like Chloe, she was a bottle blonde.

“Mike! You’re looking good!” Diane grinned. “The sailing life must agree with you.” She always thought he was a very good looking man. And there was always something about him that made her feel a little uneasy, like she was guilty of something. She assumed that was just because she was attracted to him, and considering her past which only her deceased husband and Kevin knew about, she sometimes fantasized about him. If only she’d know him back when she was still an avid swinger.

Mike grinned. It wasn’t just the sailing that made him look and feel younger than he had in years. Of course, he couldn’t tell Diane it was because having sex with her 18 year old daughter was exhilarating. “It doesn’t suck.” he agreed, making Diane laugh.

Kevin leaned into the frame next to her mom, and grinned. “Hey, kiddo.” he said.

“Hi Kevin!” Chloe smiled.

“Mike. You taking good care of my step-daughter there, little brother?”

Mike snickered. “Oh yeah. She’s doing great here. Couldn’t have done this trip without her. She made the whole trip a lot more enjoyable.” Mike pitched Chloe’s ass, making her giggle.

“I’m sure she did.” Kevin nodded, sounding a little… smug maybe?

“Mom. I have something important to say.” Chloe said quickly before she lost her nerve.

“Sure, honey.” Diane replied, more serious.

“I’ve been really enjoying this sailing life too, and… and… I want to stay and crew for Uncle Mike.”

“Really! That’s great!”

“No, I’m serious, and… wait. What?” Chloe shook her head like she was dislodging something from her deceived ears. “That’s okay?”

Diane laughed. “It’s wonderful.” She sighed. “Oh, I wish I had an opportunity like that when I was your age.”

“So you’re okay with me staying?”

Diane laughed. “Of course, honey! But what about school? You know the first semester begins in just a few weeks.”

“Yeah, about that. Umm… I thought I’d… take at least one semester off.” If she said she wasn’t going back to school ever, her mom would totally freak! She needed to do this in stages.

“I understand.” Diane nodded. “It’s actually a good idea. This will give you a chance to decide on a major.”

“Right! Exactly!” Chloe breathed easier.

“Oh, but what about Adam?” Diane asked.

Chloe’s mind raced. Something believable. “Oh, we talked. He’s fine with it too. We’re not being exclusive anyway. He sees other girls, I see other guys… you know how it is.”

“Did you two break up?” Diane asked, sounding a little concerned, even worried.

Chloe knew her mom liked Adam a lot. Chloe had been friends with Adam since middle school, but only got involved in the last couple years. And she knew Adam was her first lover. Chloe made a casual shrug. “Not really broken up. We just… want to give each other some space.”

“But you’re still together?”

Chloe nodded. “Oh, sure. Yes. We’re still…”

“Oh good!” Diane sighed. “That would have been awkward.”

Chloe squinted back at her. “What would be awkward?”

“Well…?” Her mom looked over at Kevin, then they each nodded to one another. “Okay, we were gonna surprise you, but… we thought we’d book flights down to St. Thomas for the end of the summer! Isn’t that great? We’re going to charter The Sea Nymph!”

Chloe felt her heart freeze in mid beat. “You’re going to what now?”

“If that’s okay, little brother.” Kevin said. And there was that tone in his voice again. “I’m not asking for a freebee. We’re paying customers, okay?”

“Umm…” Mike wanted to say ‘No! You’ll find out I’ve been fucking your step-daughter! Stay away!’ but he managed a smile and nodded. “Sure. I guess… we could use the business, right?”

“Exactly!” Diane said. “And I talked to Adam about it, and I thought we’d take him with us. That would be great, right? A week sailing in the Caribbean! Oh, I can’t wait!”

“Adam is coming?” Chloe choked.

“If that’s okay.” Diane smiled. “He wasn’t sure you’d want him there, but I said you’ve probably missed him, and would love to see him again. Right? And, I know you two have been… you know, so I think it’s okay for you to share a cabin. You’re still on the pill, right?”

Chloe’s head was starting to hurt.

Think, girl! Think! Why can’t Adam come? Shit!

“Chloe?” Her mom altıparmak escort had that confused/worried expression again.

“Oh, umm… yeah. Sounds awesome! I can’t wait.” Chloe’s stomach hit rock bottom, and she felt a little sick.

They spent a few minutes picking dates and decided they’d be flying into St. Thomas in just 11 days. When the call was over, Chloe hung up, and immediately dialed Adam. How could he not warn her about this?! A phone call! An email! A text message! Something!

“Hey!” Adam answered.

“Hey nothing! Why didn’t you tell me about my mom flying you down here?” She barked.

“What are you talking about?” Adam growled back. “Did you even check your messages?”

Chloe blinked, then tapped up her messenger. “Oh…” she gulped. 22 unread messages.

Talked to your mom. She wants to fly down and see you.

Your Mom is asking if I want to come. What do you want me to say?

She’s really excited to see you. I need an answer. What should I tell her?

Where are you? Get back to me ASAP!

Getting worried! Are you out of cell range?

She’s pricing tickets! Hurry and get back to me!

Sent email. Hope you read it soon. Text me as soon as you do!

There were more in the same vein, all trying to warn her. Then, toward the end of all the warnings came this.

She kinda put me on the spot. She won’t take no for an answer. She’s buying me a ticket.

Chloe frowned back at Adam’s smirking face. “We must have been out of cell range.” Chloe mumbled. “And… my phone ran out of charge last night. And we’ve been out all day. I plugged it in when we got back to the boat.”

“You see!” Adam barked. “I tried to warn you.”

Chloe nodded. “Yeah, I see.” She groaned. “Fuck! What am I supposed to do now?”

§

Eleven days went by in a blink. The Nymph was registered, and they had a temporary copy of the registration to keep on the boat until the official one arrived. They met with several charter companies to see about working with one of them. And Chloe begged Adam to help make a web page for the Sea Nymph to post on the wildwaters.org site. He agreed on the condition that when he was down there with her, he’d get to share her cabin. She had expected that anyway, and readily agreed.

The page came out great. They joined wildwaters.org, and learned that the boat could be registered with any of the popular chartering companies, and still be part of the wildwaters network. Adam made a picture gallery, and added a lot of pictures of the Sea Nymph, both inside and out. Then he made a private gallery for members only. The first cover pic was just Chloe, topless on a beach at sunset, and her face and cleavage were dripping with cum, obviously much more than one cock could provide. Since it didn’t actually show any sex happening, the site admin said he was allowed to use it.

He added more pics of Mike and Chloe as Captain and First Mate, as well as a ton of shots of Chloe making out with Mike, Dave, and Rick. One of her on her hands and knees, smiling back over her shoulder… which was pretty obviously taken by someone fucking her, though he had to crop out the best parts.

There were a couple of her in the sailor’s costume/uniform with the captain’s cap on her head, and the top unbuttoned so you could see part of both nipples. Several of just Chloe naked on the boat. And one where she was sitting on Mike’s lap, her face in what looked like orgasmic bliss, with Dave and Rick on either side feeling her up. This one just squeaked by, because it technically met the restrictions. He cropped out Chloe’s pussy with Mike fucking her, and both her breasts were, technically, covered.

Over those eleven days, Mike started to feel like he and Chloe had become a real couple. They woke up to sex every morning, and went to bed for more sex every night. They went shopping together in the market, cooked, ate, and cleaned together. Went to the bar, the restaurant, and the supply store together. And people around the marina became friends, accepting that, somehow, this middle aged man and that pretty teen were a couple.

The night before Diane, Kevin, and Adam were due to arrive, Chloe was particularly clingy.

“If I have to sleep without you for nine days, I want to get as much time together as possible.” she said.

Mike agreed. “Maybe we can sneak off for a quickie, now and then.”

She giggled. “Oh, I am all about that!” she sighed in his arms. “Maybe you should take some of that sex oil with you all the time. This way, if we have the opportunity, we’ll be ready.”

“But your little pussy is always ready.” Mike teased her.

She purred back. “Yes, but I don’t just want you to fuck my pussy, you know.”

It was another night of wild sex. Chloe loved the gentle love making, but every so often, she wanted it rough, and considering that she might not be able to fuck her Captain for over a week, or at least not much during that time, she osmangazi escort wanted a night to remember.

And Mike was more than happy to indulge her kinky side. He wrapped her wrists with the lanyard behind her back, and yanked on her long blonde hair while brutally fucking her pussy and ass. Her screams and whimpers were like a tonic. There was just something wonderful about how she wriggled and struggled, always with that desperate smile. And she’d taken to begging him to ‘do it harder, faster, deeper’ and the like. It all worked to keep him hard long enough to fuck her through three orgasms before he pulled out of her ass and decorated her face with his cum. There was something wonderful about her pretty face wet with his cum. She looked so cheap and slutty, and still so sweet and innocent, like a perfect picture of contradictions.

Afterwards, Mike released her, and they showered together. It was very tight with two people in the small space, but they sort of liked it that way. Clean and sexually sated, they lay on the bunk, dreading the morning to come.

§

Mike stood by the gate waiting for the flight to disembark, and the baggage carousel to begin. Chloe was looking twice as nervous as he was, and he reminded her several times that they needed to act natural or all sorts of hell would break loose. Then he saw that unmistakable bottle blonde with her still stunning legs and firm butt. For a woman in her forties, Diane was a MILF. Kevin saw him right away, waved, and got into position by the carousel while he waited for the baggage.

“Where’s Adam?” Mike asked.

“There he is.” Chloe said, and waved at the tall, not very athletic kid who looked too young to be in college. He still had that goofy school boy haircut, and golf shorts with a floral shirt like he was in Orlando. She suddenly realized how much she now preferred older men. Boys were just not doing it for her anymore.

Diane skipped over to the gate, and threw her arms around Chloe. “My baby!” she shrieked. “Look at you! I think you may have added a few pounds…” she said and winked. “In all the right places! Wow! I love that sundress!”

Then she threw her arms around Mike, and kissed his cheek. “Hey, stud.” she whispered next to his ear. “Oh, God! It’s so unfair how men look better with age!”

Mike snickered. “You’re not too shabby yourself, Diane.” he said, and gave her rear a little pat before she got away. “How was the flight?”

“Terrifying!” she gasped. “I thought we were going to hit a mountain as we landed.”

Chloe laughed. “Oh, if you liked that, you’re gonna love the cab ride to the marina.”

When Adam and Kevin had collected all their bags, they joined them, and Chloe got a big hug from her stepdad, and a two-hand grab on her ass from Adam as he picked her up in a big kiss. They trooped out to the livery station and got a huge van to take them back to the other side of the island. The ride was everything Chloe had promised, and Diane was white-knuckled the whole time.

After stowing all their baggage, Chloe and Mike took them to their favorite restaurant in the marina; a cute place called the Drunken Mermaid. The food was great, the prices even better, and they enjoyed a great dinner before returning to the Nymph.

The flight had taken a lot out of them, so Diane and Kevin retired early. This left Mike, Chloe and Adam on deck to make a dent in the rum supply. Chloe had learned her limit at last, so she only drank enough to be relaxed and a little silly. Then Mike went below and returned with a goodly portion of the pot Esteban had given them, and rolled them a joint.

The smoke and the booze took its toll, and Chloe was feeling her inhibitions melting away. Having her Captain and her, she supposed, ex-boyfriend together was giving her wicked ideas.

“Shove over.” she told Adam, and slid with him to make room on her other side for Mike. “Come sit here, Captain,” she encouraged him.

Mike sat next to Chloe, and she turned Adam’s lips to hers, then turned and did the same with Mike. Adam’s eyes were as big as saucers. He sort of knew all this had been happening, but to see it up close was different. She kissed him again, then back to Mike.

“Keep an ear out.” she whispered to them, then went to work opening the zip on Mike’s shorts. She reached in and fished out his stiff cock, then turned and did the same with Adam, getting his stiff length poking out. She then sat back between them, jerking them both off at the same time as they proceeded to unbutton her sundress and play with her pert little breasts.

“This was my first two-cocks-at-once experience.” Chloe said quietly. “You and John in his car.”

Adam nodded and groaned quietly as her hand, now more talented and experienced, glidied expertly up and down his hardon.

She took another look toward the aft cabin hatch, then to the main cabin inside, and convinced they were alone, she bent down and sucked Mike’s hard cock into her mouth. All the while, she kept her hand sliding deftly up and down Adam’s shaft, making him struggle not to moan out loud.

“Shit! You’re good at that!” he hissed.

Chloe lifted her mouth off Uncle Mike’s cock and licked her lips seductively. “I’m even better at this.” she boasted, and bent to suck Adam’s cock into her mouth.

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