Cruising Chloe Pt 05

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

§

"Take your time." Rick coached her. "It's a marathon, not a sprint."

Chloe bobbed her head on Mike's stiff cock, using her tongue the way she was told to. Her hand pumped him into her mouth while her other hand kept stroking Dave's big manhood. She switched and started sucking Dave while keeping Mike's shaft in hand.

"That's good." Rick said, sliding his fingers over her wet pussy as he knelt behind her. His other hand held a smart phone that was making a video of her performance. Her hips rocked in time with his hand rubbing her clit, and this set her pace for the blowjob and handjob she was giving. Her little moans and cries were helping too.

"Damn... I'm close." Mike groaned.

"Me too!" Dave replied. "God damn, her mouth is so fucking good."

"Keep going, girl." Rick encouraged from behind. "You got this, Chloe."

She switched again, taking her Uncle Mike's thick manhood down her throat, then bobbing on the head, eager for her two men to cum for her. And her pussy was convulsing on the verge of an orgasm of her own. She couldn't wait to finish sucking off Mike and Dave so Rick could fuck her.

"This is it!" Dave announced, and just as she was about to switch cocks to take Dave's load in her mouth, Uncle Mike grabbed her by the hair, shoved his length down her throat again, and cum flooded her mouth as Dave shot all over her face. Her squeaks and moans were filled with excitement, punctuated with the sound of her gulping down all the cum her Captain fed her.

At last she slurped her mouth off Mike's cock, swallowing hard and giggling with delight with streaks of Dave's cum shining on her cheeks and nose. "I did it!" she cheered. "I really did it! Two at the same time!"

"You did." Mike nodded, feeling like his heart was trying to beat a hole out of his chest.

"Fucking hell..." Dave groaned. "Genuine, Grade-A cum slut!" he groaned.

"Hey!" Mike was about to scold him.

"No!" Chloe giggled. "I am. I'm a cum slut! Watch!" She dove onto Dave's cock, sucking the cum from his shaft and milking him for every drop she could get, wiping more from her face and smearing it on his shaft to repeat the process. She made little yummy sounds, savoring the salty tang on her tongue just to prove her point.

When she was done with Dave, she shifted closer to her Uncle Mike, and the way she treated his cock was noticeably different. As she always did when she made him cum, she made love to his cock afterwards, licking, sucking, and kissing every tiny bit of cum she could get. "You see. Cumslut." She smiled up at Mike, then lifted up on her knees to kiss his neck. "Your cumslut, my Captain." she added in a whisper.

Mike ran his fingers into her hair, turning her face up to him. Before he could reply, she cried out, and grabbed onto his thighs.

"Ohh! Oh, Uncle Mike!" she groaned as Rick came up from behind and started fucking her. She held onto Mike the whole time, looking up at him as her pussy was ravaged by Rick's thrusting length. It was a wonderful reward for her successful performance. Thankfully, Rick was in no hurry, and he rode her for a long time until she was near exhaustion. She lay her head on Mike's lap, and on a whim, she took his spent cock into her mouth again. It was such a thrill. Every time Rick fucked his cock into her pussy, her mouth got shoved down onto Uncle Mike. Two cocks at once again.

Rick held his phone off on different angles, snapping pics of his cock in her pussy, her face being fucked by Mike, her eyes looking back over her should as she cried out. They had been taking a lot of Pics of Chloe in action, and a lot more of Chloe just being Chloe. Sunning herself nude on the tramp, behind the wheel, adjusting sails, or just lazing about with one of the crew while she read a book or listened to music. She never shied from the camera, and always wanted to see them after.

Toward the end, Rick passed his phone to Mike, grabbed their teen Yeoman by her ponytail, and went at it like a fiend until he came deep in her pussy while she screamed and got launched into her own orgasm. The convulsions of her clenching pussy massaged Rick's shaft, and he groaned with sheer pleasure. "Holy shit... she's so fucking tight!" He kept himself deep in her sex until her climax ended, then he pulled out, and sat opposite mike.

Chloe knelt there, with her head resting on Mike's thigh as she tried to catch her breath and savor the lovely tingle still reverberating through her like bell.

"You're not done yet, Yeoman." Rick growled. "This cock needs cleaning."

"Yes, sir. Right away, sir." Chloe, still panting, crawled over, and went to work sucking, licking and kissing Rick's cock clean while Mike snapped a few more pics. Over the last few days, she found she really enjoyed the taste of a cock that had just fucked her. The minglied flavors of her pussy and cum was lovely... not that she'd call it delicious, but she loved it anyway.

When she was done, she sat back on her heels, and Mike snapped another pic of her satisfied expression, still streaked with smears of cum on her face. She was so beautiful in those moments. Always cute and pretty, but when she had this look of sexual bliss, or what she called her 'just laid look', she was absolutely stunning. Mike lovingly stroked her hair. "Well done, Yeoman."

She smiled proudly. "Yes, sir. Thank you, sir."

"Best damned breakfast on the planet." Dave snickered. "But I'm ready for some coffee. Can I get anyone a cup?"

All three of them raised their hands, and he laughed. "Right. Four coffees, comin up."

Mike helped Chloe up from her knees, and took her with him to the wheel where he took over from the auto-pilot. "You alright?"

She sighed, using a towel to wipe cum from her face. "Captain, I'm always alright with you and my shipmates." She wiggled her pert little rear between his legs and leaned back into his chest, taking one of his hands to pull it around and hold one of her breasts. "I did it, Captain." she said proudly. "So, you said that when I was successful, you'd give me a new assignment."

Mike snickered. "Wow! Ready for more so soon?" he laughed.

"What?" she giggled back. "You said you'd teach me. And I really want to learn. So, what are your orders, sir?"

"Well, I think, since she got two cocks down..." Rick began, "I think she should try for three next."

Chloe gave Mike a huge smile over her shoulder, and those bright blue eyes were filled with lustful excitement. "Can I'?" she asked eagerly. "How would we do it?"

"Well..." Mike smiled. "I think for starters, one of us will be fucking you while you give head to the other two."

Chloe's smile brightened even more. She loved it when Uncle Mike talked dirty to her like that. She felt like such a slut, but in a good way. And it made her feel like he saw her as an adult now, not just Diane's little girl.

"But... we could do it another way." Mike continued.

She nodded. "Okay. How?"

"We should probably get her used to some anal sex first before we try a DP with the kid." Dave said crudely as he handed Mike and Chloe their coffee mugs.

"DP?" Chloe gulped. "What's that?"

"Double Penetration." Rick grinned.

"Double?"

"One cock in your pussy," Mike explained quietly in her ear, "and another in your ass."

Chloe gasped, but her hips did a little involuntary wiggle, making Mike's spent cock rub against her bare bottom. "Oh my God! Would that even work? I mean... I can hardly fit one of you at a time." Chloe wriggled back at Mike again. Despite her objection, he could feel her nipple stiffen under his hand. "So... me on top, and one of you... behind me?"

"That's the idea." Mike said, giving her tit another fond squeeze and tug at her nipple. "What do you think?"

She nipped her lower lip, and took a breath. "I don't know. Sounds... a little scary. Have you done it before?"

Mike smiled, but shook his head. "No. Two on one, yes. Like today. But not three on one."

"So it's a first for you too." she breathed a little easier. "Okay... and, do you like doing... you know... that?" she asked in a shy whisper.

"Anal sex?" Mike hugged her and nodded. "Very much, yes."

"Then I want you to do it to me." she said at once. "I want you to be the first to do me like that. Okay?"

Mike snickered, hugged her close and kissed her bare shoulder. "I'd be honored to take your anal virginity."

Chloe brightened, and sighed. "Yes! I like that idea. Mmm, yeah. Giving you my virginity." She leaned back and whispered. "Will you do it to me tonight?"

"Tonight?" Mike asked.

"Tonight." she nodded. "I'll come to your cabin, and you can do it to me. Okay?"

Mike suddenly felt his cock trying to rise again. "Okay, Baby." he whispered in her ear, and got a soft purring moan from his lovely little step-niece. She just loved it when he called her Baby.

§

The rest of the morning was more relaxing. The wind was favorable, the sea was calm, and Chloe had done a great job at getting them all off, so nobody was feeling particularly hard up.

"That's our next port of call. Turks and Caicos." Mike announced as they turned towards land for the last tack.

"What's it like?" Chloe asked excitedly.

Mike laughed. "Never been there." he said.

"I have." Rick said. "Amazing hotels, restaurants, and beaches." He waggled a brow at Chloe. "I also know of a small island where there's... clothing optional."

"A nude beach?" She giggled. "Can we go, Captain?"

Mike laughed. "Oh, hell yes!" he nodded.

"The nude part only happens at night after the beaches are deserted." Rick added. "They have pretty strict rules against public nudity. So, hopefully they still have the beach parties. Pretty fucking awesome."

"I can't wait!" Chloe giggled.

Dave laughed. "I think we turned her into a nudist."

Chloe proudly thrust her tits out at him and blew a kiss. "Oh, that reminds me." Chloe said. "I need some more pics of me with clothes on to send to mom."

"Wait... one more for the archive." Mike dug out his phone from his pocket, and held it out to take a selfie with Chloe, stretching his arm so he could get his hand covering one of her modest little tits in the frame. She smiled her winning smile for the first, then turned and kissed Mike full on the lips for a second.

§

Chloe remained naked until they were entering the harbor. Then Mike ordered her below to put on something while they lowered the sails and started the engines. She returned minutes later in a string/thong bikini that left little to the imagination. When they drove toward the Marina, she stood on the bow with a hair brush turning her disarray of blonde hair into a smooth wave of gold. More than a few heads were turned on their way past boats at anchor to admire this pretty little bow ornament.

There were no slips wide enough for the Nymph remaining, so they found a good mooring and prepared their launch to take them ashore. Chloe tagged along with Dave who went to the harbor office to pay for the mooring, and scout out the supply store.

She thought it was fun to see all those faces looking in surprise, amusement, or even shock, when they saw her walking arm in arm with a man more than twice her age, especially when they passed and could see he had a hand planted firmly on her bare butt cheek.

In the store, Dave settled up with the dock master while she browsed the shelves. She tried on a pretty red beach wrap, checking herself out in the mirror, when Uncle Mike came up behind her and topped her head with a matching red straw hat.

"Ooo! That's cute!" she giggled.

"Should match that red bikini of yours." Mike nodded.

"Is that a request, Captain?"

Mike grinned. "Not really. I prefer you without a bikini."

The man behind the counter gawked, but didn't say anything. His face was comical though, especially when she got a long Kiss from Mike as they browsed, and another from Dave at the counter. The poor guy looked terribly confused.

Mike bought Chloe the hat and beach wrap, and they got several cans of spray sunblock. They needed ice too, but decided to pick that up on their way back to the boat.

At the check out, Dave came up and plunked down a bottle of intimate massage oil. "Gotta lube that ass, right Yeoman?"

Chloe blushed a smile at the clerk who looked like he'd just swallowed a bug. "Yes, sir. Thank you, sir." she replied, and slid the bottle over with her hat and wrap. She was so tickled inside, she could hardly stand it.

There was a hotel nearby with a pool and sundeck that looked very inviting, but only guests were allowed. As they walked by close enough to see all the amenities, Chloe groaned with longing.

"Oh!" She pouted. "I love the ocean, but I would kill for that hot tub. Ohh! And a really long shower! Wouldn't that be great?

Mike and Dave walked with Cloe arm-in-arm between them, and they both looked at each other with the same idea in mind.

"You know..." Mike began. "All four of us on one bunk might be a little crowded."

"And we can't just go up on deck and gangbang our Yeoman where everyone can see." Dave added.

Mike grinned and nodded. "Well, not here, anyway. Buy, you know... a nice big king sized bed would be a lot more comfortable for Chloe's first time."

Chloe looked excitedly up at each of them. "Really! We're going to stay in a hotel tonight?"

"You and I have a date tonight." Mike said, giving her a knowing wink. "But tomorrow night, for sure. And maybe the night after."

"We have a date?" Chloe asked, then her eyes went wide and a huge smile lit her face. "Oh! Right!"

Dave frowned. "Want to clue me in?"

Chloe hesitated, but only because she wasn't sure if Uncle Mike wanted anyone else to know. But, in the end, she no longer cared who knew about how she felt. She wanted everyone to know, and if she couldn't trust her shipmates with it, who could she trust. "Uncle Mike is taking my anal virginity tonight." she announced proudly. "My Captain is going to be the first."

Dave lifted a brow at Mike. "Without us?"

Chloe nodded. "Just this first time." she insisted, and leaned closer to Mike. "I want my first time to be special."

Dave frowned. "Hmm... but when we're in the hotel...?"

Chloe giggled. "If my Captain orders me to, then yes." Then she gulped and looked up at Mike with worried eyes. "Umm... will I be able to fit Dave... umm... in there? He's kinda big."

Dave proudly nodded. "It'll hurt like a bitch at first, but I haven't met the ass yet that wouldn't open up for the beast."

"You'll be alright, Yeoman." Mike assured her. "I'll be gentle and you'll see. It's a whole other world."

"I trust you, sir." she said more calmly than she felt.

Rick caught up with them later, and they spent some time splashing in the ocean, body surfing, and enjoying a quick grope now and then. For her part, Chloe encouraged the groping, almost daring them to come for her. In the end, she was surrounded by her Captain and two shipmates, and they kept her neck deep to hide what they were doing to her under the water. Rick finger fucked her while Dave fondled her tits, and Mike got his finger up her tight ass in preparation for the evening to come. Her orgasm was so loud they made heads on the beach turn.

§

They had an early dinner back on the Nymph, and spent the evening enjoying a few drinks and some live music at one of the open air bars. Chloe loved making 'the straights' look concerned or confused when she danced with her three older men. And as so often happened, younger men flocked to her, and Mike was more than willing to share his beautiful Yeoman for dancing. She got rather good at the calypso style and moved so seductively. Most of the guys tried copping a cheap feel, and most of the time, she let them.

Mike couldn't figure out how to feel about it. On the one hand, he was uncomfortable about strangers playing with his teen Yeoman, but on the other hand, she looked so damned hot doing it, and she always came back to him more eager than ever for him and their shipmates to teach her more sex.

He was getting hard again as he watched her with a muscular looking black guy, his leg between her thighs, and hers between his and they did a slow bump-and-grind with one another. He could see the guy's hand holding her ass under the short summer dress she wore. And the look on her face was similar to the one she got when Mike was getting her pussy warmed up before they all had sex with her. At one point she closed her eyes and her body lurched against her partner. Then she favored him with one of her perfect smiles, got her arms around his neck for a short kiss, then came tiptoeing her way back to the bar and her shipmates.

"From here, it looked like he had his hand in your panties out there." Dave snickered.

"That's impossible, sir." Chloe sighed with a cute smile. "I'm not wearing any."

They all gawked at her for a moment. "Did he know that?" Mike asked.

She giggled and shrugged. "I think the wet spot on his thigh might have given it away."

"You came, didn't you?" Rick asked.

She nodded. "A little, yeah." she giggled again, her eyes still bright with that youthful lust. She turned to Mike, and slipped into his arms. "Requesting permission to return to the Sea Nymph to continue my training, sir?"

Dave and Rick both got a surprised look, and gave a nod.

"Permission granted." Mike settled with the bartender, and they all went back to pick up bags of ice on their way back to the launch and returned to the Nymph.

No sooner had they stowed everything, when Chloe went out to the cockpit where her shipmates had settled in, and lifted her little sundress over her head and tossed it onto the captain's seat.

"Whoa, there, Baby." Rick snickered. "Remember, they have some pretty strict rules around here about public nudity. Dave, kill the lights except the running lights and mast."

Dave did as suggested, and when he got back, Chloe was already on her knees with Rick's cock halfway down her throat. She had improved in the deepthroat department, though she still couldn't handle more than a few seconds at a time. She was getting better at not gagging though.

Mike was there with his phone, taking a few more pics of his niece with Rick's hardon between her lips, eyes smiling at the camera. Dave removed his trunks, dropped them on the deck for him to kneel on, and got down behind Chloe.

Her moan around Rick's cock was a delight to hear. She arched her back and lifted her ass to give Dave a better angle, and resumed bobbing and licking as that big shaft impaled her from behind. She loved this 'doggie style' position, and having a cock to suck at the same time was such a thrill. She imagined what a shock it would have been for poor Adam if she let him and John have her like this that night in John's car.

She never told Adam that a couple days later, John asked her out and she gave him a blowjob in the back of the movie theater. She didn't even particularly like John, but when she saw what a nice big cock he had, she couldn't resist the temptation.

Her body arched as Dave yanked back on her hair, making her shriek around the stiff length in her mouth. A smack on her ass, and she screamed as a little orgasm shot out from her pussy to her fingertips.

"Wanna switch?" Rick asked.

"Hell yes!" Dave agreed, and Chloe got spun around and mounted again by Rick.

She always struggled to blow Dave's cock. He was too long and too thick for her to get down her throat on her own, but he didn't care. He grabbed her by the hair as he usually did and plunged his whole length right down her throat as she gagged and tried not to let her stomach revolt. Eyes tearing as she endured it, Rick's thumb was stuck in her ass as he force fucked her in one of the rare but increasingly more common ravagings they gave her. All the while, she could hear Uncle Mike's phone snapping pic after pic.