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Cruising Chloe Pt 01

Cruising Chloe Pt 01

by wyrdwilly
19 min read
4.7 (32900 views)
adultfiction
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Note: All characters are 18+ and fictitious. Any names or descriptions resembling actual people is purely coincidental.

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At first, Chloe was a little nervous about the cruise. She would be gone for at least a month, and probably more! But it was the opportunity of a lifetime. When she told her mom that she wanted to go on a cruise for her graduation gift, she thought it would be on one of those big luxury liners in the mediterranean, or to The Bahamas. This was way better, but still a little intimidating.

Her real dad died when she was eight, and a couple years later, her mom remarried to an older guy named Kevin. And Kevin's little brother, Mike, was a hoot. He had this crazy personality, always cracking jokes and telling stories she knew were either made up, or embellished. But the best part about Uncle Mike was that he was a boating fanatic, just like her father was... and Uncle Mike shared the same love of the open water she inherited from her dad. Because of that, Uncle Mike was like her hero.

He had gone to the NY Maritime Academy, and after graduation he worked on cargo ships, then landed a job on one of the beautiful cruise ships, which is where Chloe wanted to be some day. He had to quit that job when his wife had a baby so he could be home more. He then used the money he saved, and the connections he had, to buy a boatyard in Maryland. Whenever they went to visit, he would take her sailing or fishing on the Chesapeake.

It had been a couple years since they got together with Uncle Mike, so she was really excited to see him again. Her mom said that after his divorce, he bought himself a gorgeous yacht, and was planning to take it to the Caribbean where he would charter it. To do that, he needed a crew, and he invited Chloe to be one of them!

Mike had big plans for the Sea Nymph. She was a stunning 50 foot catamaran he got for a great price after it had been damaged in a storm. He fixed her up, got the engines purring beautifully, and even replaced all the sails and rigging. When chartering, appearances can be very important.

When Diane, his sister in law called about Chloe's graduation, and suggested he take her down to the Islands with him, he was pretty skeptical. Chloe loved sailing, for sure, but could she handle weeks on the open ocean? And it wasn't like she'd just be along for the ride. She'd have to help crew the boat. That wasn't always so easy. But Chloe was a good kid. Very smart, funny, and she loved sailing. He figured, wherever she didn't know, he could teach her.

Mike was taking a month to sail his beautiful Sea Nymph to the Virgin Islands where he was going to charter it. In truth, he was just trying to get away from his miserable ex-wife who had taken him for nearly everything in the divorce. Luckily, his brother was a half owner in the boatyard, so she didn't get that. Mike sold his half to his brother, and used the money to buy and fix up the Nymph. He needed a change... bad! A cruise to clear his head, and bumming about the Caribbean sounded like just the thing.

He arranged for Dave, his best friend, to do the cruise down to St. Thomas. Ricky, Dave's cousin, seemed a lot like Dave. They both had the same quirky sense of humor, the same Boston accent, and they both prided themselves on their ability to turn almost anything into an edible meal... a valuable asset on a boat.

Diane dropped-off Chloe at the marina, made Mike promise to take good care of her little girl, and had a teary goodbye, making Chloe promise to call or text whenever she could.

Mike was... stunned. The last time he saw Chloe was over two years ago at her Sweet 16 birthday party. She was this skinny little kid back then, with no figure to speak of, freckles, and braces. Cute, but not... well... not this! She was still a cute little thing, but she had developed breasts since then. Not big, but respectable. Her face still had that girlish quality and some remaining freckles, but the braces left her teeth perfect, and she had a dazzling smile. Then there was the rest of her.

"Oh my fucking god..." Dave groaned as he got a look at Mike's niece in her tight little shorts, crop top and deck shoes. She was a gorgeous blend of cute and sexy, with great legs and a perfect ass!

"I know." Mike groaned back. "Not a kid anymore."

"Nope." Dave agreed. "Oh geez! Four weeks with her on board? Talk about torture."

"Uncle Mike!" Chloe ran over and threw herself onto her uncle that she hadn't seen in years. "Thanks for letting me tag along." she kissed his face and slid back down to her feet.

"No tagging involved here, missy." he chuckled. "You're not coming along for a ride. You're part of the crew. So, get your butt moving. Stow your stuff in the forward port bunk, and report on deck for orders."

"Aye, aye, Captain!" she giggled, and hurried off with her overstuffed duffle on her shoulder.

Rick was just coming out of the main cabin, and almost ran into Chloe on her way in.

"Whoa!" he gasped at the cute little blonde. "Umm... you're Chloe?"

She nodded. "That's me." she offered her hand.

"Uhh, Rick." he shook her hand.

"Hi Rick. I have to get my stuff below. Be right back." She scurried past him and down the steps to the cabins on the port side.

Rick came up on deck looking like he'd been smacked with a silly stick... big shit-eating grin, wide eyes, lost expression. "That's your niece?" he gasped at Mike.

Mike nodded and gave a little shrug. "I had no idea she'd grown up... or grown up like that, anyway."

"This cruise just got a lot more interesting." Rick snickered.

"Hey!" Mike frowned. "She's my niece... or step-niece... or something. Whatever. Just... keep it in your pants."

They made sure everything was secured, checked the fuel, water, batteries, wind generator, solar panel, compass, radar, and everything else in fine detail. No sense in leaving without making sure they were at 100 percent. It's a lot easier to fix stuff at port than at sea.

By noon, they were ready to cast off, and started their first leg from Miami to Bimini. Mike was the skipper, so he called out the orders when sails needed adjusting or course needed correcting, but all of them knew what they were doing. Even Chloe with her limited experience was on task, and had a real feel for setting the jib for best results.

Just as the sun was setting, they cruised into a lovely marina, and found the dockmaster for a place to tie up for a couple days. Mike had some worries about the weather, and wanted to let a storm out at sea decide where it was going before setting off. They squeezed their wide catamaran into a slip that was only just big enough, got her secured, and settled in for the night. Dave fixed them a terrific meal, and they ate on deck, enjoying the warm night.

Chloe had noticed how Dave and Rick looked at her. She knew she was good looking, but these older men stared like she was a supermodel or something. It was very flattering, if a little awkward, considering their age. But she also noticed how Uncle Mike didn't do the same. Maybe he was just really trying not to look. She figured him being her uncle... or step-uncle, made a difference. Or maybe he just didn't find her attractive. She remembered that his ex-wife was stacked! Huge breasts, a big butt. Maybe that was more his style.

After dinner, they sat on deck with some nice boating music playing on the boat's soundsystem. Lots of calypso, Jimmy Buffet, and steel drums.

"Here you go." Mike said as he took a seat next to Chloe, handing her a rum drink. She took a sip, and made a cute little squeak when she tasted the liquor.

"What is this?" she asked excitedly.

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"Pina Colada." Mike grinned back.

She sipped it again, and rolled her eyes in pleasure. "So good! I had one of these at Nichole's wedding. It wasn't this good!"

"Well, I make them better than some catering business." Mike said proudly.

"Why is yours better?" she asked.

"I actually put rum in mine."

Chloe giggled and sipped some more. "Mom would kill me if she knew I was drinking."

"It's legal here." Dave said.

"Really?" Chloe asked.

He nodded. "Drinking age is what... 16 or something?"

"18." Rick corrected him.

"Oh! Then I'm legal!" Chloe said cheerfully, and wondered why Dave and Rick snickered to each other.

They drank more, enjoying the company and the quiet. Dave even got Chloe up to dance a little. Mike was cautious of it. His adorable niece in her little bikini wasn't a kid anymore, but she was still his responsibility. He just sort of wished she wasn't so damned pretty!

Four weeks with her on board! Shit!

Chloe took herself to bed a little before midnight, and the guys followed suit a little later.

They spent the next day there, and decided to take their dinghy out to the beach for a swim. Mike, Dave and Rick got the flippers, masks and snorkels into the little launch, and waited for Chloe. She finally came out of the main cabin, and all three of them just gawked. She'd chosen a very skimpy bikini with a thong back, and her cute little butt cheeks were cleft by a little yellow trip that just seemed to accentuate her bare bottom! So cute!

They drove around the harbor entrance out to the sandy cay, and snorkeled with the stingrays and fish for a while. Chloe caught Dave and Rick checking her out again, and showed off a little, diving down to pick up some interesting shells or chase some fish. It was kinda fun, watching them follow her with their eyes. But still, Uncle Mike was oblivious. Like he wouldn't look at her no matter what.

Chloe's boyfriend, Adam, said she had a great ass. She let him take her V-card the day she turned eighteen. After the little birthday party her mom put together for her, Adam took her to the movies, and she gave him a handjob in the theater. Then, after the movie, he took her home, and they snuck down into the furnished basement while her mom and stepdad were sleeping in front of the TV in the living room.

It was quick. They didn't want to get caught. And it hurt a little. But she felt so proud of herself for finally having sex! And it was so much better than just playing with herself. But that night, when they had sex, Adam said that she had the best ass ever!

Round, and firm and perfect

he said. So... why wasn't Uncle Mike checking her out too? Probably because he was

Uncle

Mike. That made sense.

They had cold grilled chicken on the sand, and Chloe was given her own bottle of beer. She decided she preferred Pina Coladas, but drank it all just the same. A little more swimming, then they were back on the boat to check the weather updates. The storm was moving off, leaving them a clear course to the Bahamas. They checked the charts, plotted the next leg, and topped off the fuel tanks so they could leave early.

That night, Mike made her another drink, and she danced some more with all three of them. At one point, Mike noticed Rick slip a hand around Chloe's back, and slowly let it drift down to her ass... and she didn't stop him. He felt like he should say something, or cut in or something, but Dave got to her first. Then, after a little time, he did the same, resting his hand on her round cheek, and he even gave it a squeeze.

Chloe just giggled along with their touching. They were so much older than her, it wasn't like it was really flirting or anything. This was just a bit of fun. But she kinda liked how it made her feel when they did grab her ass. Adam's words kept creeping into her mind.

Round, firm, and perfect,

he said. Maybe they thought so too.

She danced by herself for a bit, and felt so... strangely excited, watching them watch her. She just went with the calypso beat, swaying her hips and running her hands through her hair and over her body. It felt so good to be out in the hot island weather.

A second drink, and she felt even better. Uncle Mike finally danced with her, and she practically had to move his hand for him to get him to touch her. But he got the idea, and just like Dave and Rick, he got one hand over her ass, and she smiled up at him with that brand new smile. The braces had done wonders.

"Make me another drink, Uncle Mike?" she asked.

"It's late." he replied. "And you've probably had enough."

"Oh, come on! I'm legal! remember?"

Damn, yeah he did. She was legal... for all sorts of things. Against his better judgment, he fixed her another, though with a bit less rum this time, and her dancing became more and more provocative as the night wore on. Finally she let Uncle Mike talk her into going to bed, and stumbled down to her cabin to sleep it off.

Dave and Rick, deprived of Chloe for entertainment, went to their cabins, leaving Mike on deck to look up at the stars alone.

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At some point, he fell asleep, and didn't wake up until he felt something move next to him. Chloe sat beside him on the cushion, and sleepily leaned over and kissed his cheek. "Thanks for bringing me." she slurred. "I'm having such a good time."

"I'm glad." he replied, and shifted over to give her more room... which she scooted closer to take up. She rested her head back against his shoulder, and looked up at the stars with him.

"Never seen so many." she sighed.

"Wait till we get out on the open ocean." Mike grinned. "No light pollution out there. You'll see them all."

"Can't wait..." she yawned and cuddled closer... making Mike's shorts suddenly tighter. Soon after, she was breathing slow and steady. She had fallen asleep.

Mike repositioned her to lay her head on his lap, and tentatively rest his hand on her hip. She felt so slim and firm... like the gorgeous girls he used to date when he was younger. Firm, sexy, and smooth as silk. Damn! Four weeks of her? That adorable ass in those thong bikinis. Her perky breasts, toned legs, cute face with her bright smile and youthful freckles. And the way she felt when they danced, her tight little ass under his hand, just so... perfect.

As he remembered it, his hand moved and slid down over her ass again. She made a cute little cooing sound, and shimmied her hips to get more comfortable... making his fingers rest into the cleft of her round cheeks.

Oh crap!

he thought to himself. The firm globe of warm flesh just filled one hand, and he dared to gently squeeze. So sweet and young... and his brother's stepdaughter! Shit! He needed to stop.

She shifted her shoulders and her little breasts under her bikini top came into view. He sat there, just staring down at her, struggling to not do what he wanted to do. He couldn't. Obviously. But if he didn't move, and soon, he was going to do damage. His cock was so stiff, it hurt. The shorts he was in left no room for an erection like the one he had.

Should I? I shouldn't. But damn... it feels like it's gonna snap in two! Maybe... just make a little room...?

Mike carefully unzipped his fly, and reached in, letting his fingers make a path that gave his cock an escape. Seven stiff inches popped out, and he sighed. Now what? He couldn't move, not like that anyway. His right hand, the one he usually used in situations like this, was occupied with Chloe's tight little rear. He couldn't reach over her without waking her up.

Okay, time to become ambidextrous.

Chloe shifted, trying to get more comfortable. She slid up, nestling her head on the firm pillow, trying to rest her head on her side... but the darn pillow kept moving. It was like it was rocking back and forth, and she wondered if maybe a boat had driven by and left wake... but it was rocking too quickly. She reached up to adjust the pillow, and touched... what was definitely not a pillow. A leg. A bare leg. She bleerilly opened one eye, and struggled to see in the dim light of the marina.

She was resting her head on someone's lap in the cockpit, and there, just inches from her face was... was...

oh god!

It was the second cock she'd ever seen in real life! Stiff, and hard, and standing right up in front of her face. And he was touching it with his hand, rubbing it with his fingers.

As her mind came back to the land of the living, she realized his other hand was resting on her ass, and she could feel it grab and squeeze her gently. Wow! How did she end up like this? She remembered going to bed, and the cabin was spinning. She remembered laying on her bunk, and deciding not to get undressed. Then... then what...? Oh! Right! She got up to pee! She went to the head and peed, then... then saw someone on deck. She went to see who it was and...

Uncle Mike! It was Uncle Mike up there. I went out to see him, and we looked at the stars, and then... laid down next to him and... oh boy!

For a while, she just lay there, watching Uncle Mike rub at his stiff cock with his fingers. She recognized the same musky smell she remembered when she gave Adam a blowjob that first time in his car. They'd been having sex pretty regularly by then.

After her first time, Chloe had confessed to her mom that she was sexually active, and wanted to get on the pill. She'd been on them since, which was about three months now. And soon after learning how to have sex without discomfort, and really starting to enjoy it, Adam asked her to give him a blowjob. She had no idea what she was doing, and the first few times, she couldn't get him to cum. When she finally talked to one of her girlfriends who had more experience, she got some good advice, and tried it.

The same musky scent, the same tang she could feel in her sinuses. But it was dark, and his cock was up by her forehead. This was so weird. Why would Uncle Mike take out his cock with her right there? Another grab on her butt, and she felt her insides do a little tumble. This is what it was like when she was with Adam. She was getting horny!

How? This is Uncle Mike! We couldn't... but... I wonder...

She wanted to see if the tip was wet like Adam's had been. Was he going to cum like Adam did? Would she get to watch it?

She shifted, still pretending to be asleep, and slid herself a little further up Uncle Mike's hip so she could rest her head on his abdomen. At this angle, she was able to get a clear view, and sure enough... the tip of his cock did glisten a little in the light from the boardwalk.

Mike stiffened when she moved, resting her head right on his belly. Shit! She was just inches away. If only he could angle the head a little, he could touch her face with it. Stupid to even think it, but she looked so sweet and sexy there beside him. What in the hell was he supposed to do?

Still trying to do the best he could with the wrong hand, he went back to rubbing himself. Maybe if he could just get it out of his system, he'd be okay.

Just cum on your hand, and wipe it off later. That's all.

He was having a hard time of it, considering he couldn't really put the effort in that it required, and that he wasn't used to that hand. It was tormenting! Infuriating! Maddening! He thought, maybe just wake her up, send her back to bed, and go to your cabin and rub one out in there.

Then a poorly timed stroke waggled his shaft, and it batted poor Chloe on the face! He froze, wondering if he woke her. Would she get up and be horrified? Call her mother? Leave the boat and they'd be short handed... and his sister-in-law would probably kill him?

Shit, shit, shit!

Oh my god! It hit my face!

Chloe wasn't sure if she should do anything. Should she pretend to wake up, and stumble off to bed again? Maybe Uncle Mike was drunk too, and he wasn't thinking clearly... like she obviously wasn't. Maybe she should just lay here and see what happened next.

Yeah. That's the best idea. Just stay still, and see what he does.

She must be out cold

, Mike mused as he held still, waiting to see if Chloe would wake up. She did have a lot to drink. Maybe more than he should have let her have. But she didn't move. What possessed him to even think of it, but Mike took his cock by the base, and moved it slowly to touch her face again, gently this time. Not a smack in the face. Just a touch.

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