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