The Prize Day 05

"So, according to the original charter, it was supposed to by fifteen girls and five guys, where are the other four guys and two girls?" Captain Jane inquired.

"Two of the girls went home early. Two of the guys never showed up and two were sent home after being rough with some of the girls."

"Fucking assholes..." she said under her breath. "Men are fucking horrible!" she said loud and clear, making Andy retreat a bit. "Oh, not you!" Captain Jane clarified, really not meaning to include Andy in that generalization. "So according to Bob, you're a contest winner, right?" Andy nodded in the affirmative. "Good," she said matter of factly, "most rich guys with pretty girls are horrible. Much better to have someone here who can be appreciative!"

The Captain and Andy talked for a long while, backgrounds, boats, all sorts of things. It didn't take long for Jane to figure out why the girls seemed to like him and his easy-going nature. She and her crew all mostly swung the other way, but Andy certainly did seem like the kind of guy she'd like to get to know better.

Angela and Karlee saw Andy and the Captain talking while everyone else was partying. They both looked at each other.

"You don't think..." Karlee asked her cohort.

"I don't know, but the last thing we need is more competition. Follow me," Angela said heading over in their direction. "Andy, could you help us find our stuff below? Karlee was looking for her eye drops."

"Sure," Andy said as he went into the inside cabin area to search for the bags with the girls. Captain Jane was no fool and knew that the two were just trying to get him away from her. On the one hand she was disappointed, but then again, making a pair of porn stars jealous doesn't happen every day. She smiled as she went back up to the bridge to check on something.

While Karlee and Angela may have thought no one saw them go below with Andy, they were very wrong. While Sara, Dillion, Cassandra and Charlie didn't; Alex and Natasha did. They looked at each other disappointed, but also remembered that they'd just had Andy this morning. Still, the two were troubled.

Andy went into the master cabin where the vast majority of everyone's stuff had been left. He started searching for Karlee's bag, finally finding it and getting the eye drops.

"Here they ar..." he managed to get out before he realized Angela and Karlee and closed and locked the cabin door behind them, both glaring at Andy with smiles and desire.

"Thanks, Andy," Karlee said, coming up slowly to him. "You're so considerate."

"Indeed," Angela said creeping up on Andy. "I think he deserves a reward, don't you babe?"

"Oh, yeah," Karlee said as the duo pounced on Andy, forcing him to the bed. The two planted kisses all over Andy as Karlee quickly had his cock down her throat. Angela fed Andy one of her large breasts, heavily encouraging licking and nibbling.

Karlee slobbered all over Andy's dick, playing with her own pussy to get it nice and wet for him. She also managed to get a few fingers inside of Angela to prime her. Once she was satisfied by Andy's hardness and her own wetness, Karlee climbed up and sunk down onto Andy. Angela reached a hand over to play with Karlee's clit.

Karlee was moaning loud, from the attention of Angela's hand and Andy's dick.

"Yes! Frig my clit! God, I love you guys!" Karlee moaned as she started bouncing harder. Andy was holding on while the young woman rode him, trying to moderate her pace a bit.

"Fuck her, Andy!" Angela yelled full of passion and desire. "Make her scream!" Angela wanted to make sure that Karlee got off and that the other girls would all hear her orgasm. Andy started thrusting harder up into Karlee, making her breasts bounce and her moans increase.

"Fuck, I'm gonna cum!" she declared to all. "Harder!" Andy complied and Karlee was soon shuddering in orgasm. "UNGH!!!" as she gripped Andy's cock in orgasm.

"That was so hot, you guys," Angela said, getting really turned on at the sight.

"Your turn," Karlee said getting off of Andy with a smile.

Angela turned her ass toward Andy, and he dutifully shoved himself inside.

"Oh, yes!" Angela said positively of the fresh invasion. "Fill me up, babe!"

Andy started sawing into her, thrusting with power and purpose. Karlee got behind Andy and started giving him a rim job, licking as well as she could while Andy continued to pound Angela.

"You're fucking me so good, Andy!" Angela moaned out. "Take that cunt!"

Between the attention to his anus and Angela's words, he knew he wasn't gonna last long. Karlee sent her tongue straight up Andy's back pipe and that did it. Andy spilled into Angela generating a powerful orgasm for her.

"YES!!!" she screamed out, loving that Andy dropped his load in her without even asking. Andy took a few seconds to come around to his senses.

"I'm sorry," he said breathlessly to Angela.

"Don't be!" she said emphatically, cupping her pussy to keep as much of Andy's cum in her as possible. "You can cum in me whenever you want!"

"Same," Karlee added, kissing the back of his neck. They both felt they'd made a real strong step toward getting Andy.

All three wound up on deck soon after, seeing what was now unfolding. Some of the naked crew were now hooking up with the stars, a few daisy chains being formed around the deck. The sisters were working on two of the deck hands while Gianna was scissoring a steward. The others were all sitting, watching, and drinking.

Andy took this opportunity to slip away and jump into the water, wanting to clean up a little bit from his hard work below. He loved the feeling of the fresh water on him, being the perfect temperature and feeling very refreshing. He was again alone and was able to try and process all these women surrounding him and what their intentions were.

He was no fool and knew that some of these women seemed to be pursuing him. To Andy, it seemed like some were actually seeing if Andy wanted a relationship with him after this trip had ended. He was attracted to them sure, but how would such a relationship work? Not only that, but some also seemed to want a thruple relationship. How would that go down with his mother and how would he explain it if she discovered the background of the women?

Another part of him thought that this might all be in his head. They weren't serious about him; they were just engaged in a friendly competition for his attention as a sort of distraction. Maybe the best course was just to see what develops and enjoy his vacation.

From the boat, several of the girls on board had noticed that Andy was in the water. Gianna noticed after she'd finished with the steward and smiled a bit at Andy, getting some alone time. Alex and Natasha also saw him. They knew full well what had happened below deck earlier and were trying to calculate their next move. Sara also saw him there and thought of joining him.

But it was Dillion who jumped off the boat first, Liliana joining her. They swam up to Andy.

"Relaxing, isn't it?" Dillion said obviously talking of the water.

"Very!" Andy said. "The water feels so good."

"I can't believe its December," Liliana offered. She wasn't blind to what the other girls were doing, she just wasn't interested in Andy like that, being the only girl not to fuck him. But she also saw that Dillion was and decided to prod a bit as Andy and Dillion were swimming close to each other. "You two look so cute next to each other!"

"Don't we though?!" Dillion said smiling and throwing an arm around Andy, grateful to Liliana for the assist.

"How's your first boat trip going?" Andy asked Dillion.

"It's so cool!" she replied. "This is like a dream!" She then took in the sight around them, including the boat and Andy could only silently nod and agree.

After a few more minutes they all climbed up back to the boat, Charlie and Cassandra waiting for them.

"Feeling refreshed?" Cassandra asked Andy.

"It's pretty invigorating," Andy said smiling.

"Maybe you can go swimming with us later?" Charlie asked.

"Sure!" Andy said, keeping to his self-agreement to let things play out as they would. They got onto the main deck and some of the girls were sunning, some were still fooling around, and some just enjoying the ability of the bartender. Andy decided to take the latter choice and got a tropical drink from one of the naked crew members, who was obviously eyeing his cock.

And so it went for the next couple of hours, relaxing and enjoying their stay on the boat. Captain Jane asked if anyone wanted to move locations, and everyone liked where they were too much and said no. Before long, it was time for dinner and the crew got everything done to accommodate the large group. Seafood, buffet style was the order of the day, Andy insisting that the captain and crew join them.

Captain Jane liked this man and his style and agreed, the crew delighting in the relaxed atmosphere of the charter. The captain went upstairs to her cabin for a minute before returning with a smile on her face.

"Good news, everybody!" she said to the guests and crew. "I checked the books and there is no reason we need to return tonight, our next charter not being until tomorrow night. You guys wanna stay the night aboard? We have plenty of beds for everyone."

The crew, which normally would've loathed extending a charter, looked hopefully at the guests, having such a good time with them. The girls all looked at each other and all decided that this was too good a thing to miss. Everyone agreed and the cheers rang out again, the captain smiling before sitting down next to Andy.

"You can use my cabin if you'd like," she told him with a smile.

"Oh no," Andy said quickly. "I couldn't do that to you."

"I insist and this is my boat," she replied with a wink. Andy acknowledged her authority and nodded. Captain Jane smiled, delighted that these fun people were gonna stay longer. The crew all got together to make preparations for the evening and morning. Andy was relaxing with a drink on the deck, Natasha and Alex talking and teasing him. Cassandra and Charlie saw Sara looking at that trio and decided that it was time to talk with her.

"Having fun?" Cassandra asked as she sat down next to her, Charlie close behind.

"Yeah," Sara said half convincingly. "It's really nice out here."

"It is," Charlie said, Cassandra looking at her in a subtle 'let me talk' way.

"So, I saw you and Andy talking for a while," Cassandra said. Sara inadvertently smiled.

"Yeah," she said with almost a giggle. "He's really a sweet guy."

"We think so," Cassandra said getting closer to her friend. "That's what we wanna talk to you about." Sara looked at Cassandra confused. "I know you like him just as much as we do." Sara looked over and saw Charlie nodding in agreement.

"Yeah," she said almost painfully, "I really do."

"So do we," Cassandra said taking her friend by the hand, "so do some others," she noted acknowledging the other girls all near or looking at Andy. Sara looked over at them and got depressed all over again, slinking her head down. "How would you feel about an arrangement?" Cassandra said, causing Sara's head to come up in confusion.

"What are you talking about?" Sara asked.

"Look," Cassandra said, "we figure people are pairing up all over to try and tilt the scales with Andy. Clearly Alex and Natasha are, Angela and Karlee too. Charlie and I have decided to also team up, figuring we can share Andy. We'd like you to join us."

"So," Sara said trying to wrap her head around this, "we'd all date Andy together. We'd all live together and date each other?"

"Exactly!" Cassandra replied, now giving Charlie the cue to start talking as well.

"It could be wonderful," Charlie said somewhat seductively.

Sara started thinking immediately. She really didn't want to share Andy, wanting him all for herself. But as she looked at the other couplings that had already appeared in their group, she realized it probably wasn't practical. Then she looked at the two women talking to her. Cassandra had always been a good friend and she was an animal in the bed. Before Cassandra, she'd never really considered herself as into girls, mostly just playing with them or for scenes, but she was different.

Charlie she didn't know well. She'd seen some of her scenes and knew that she was a tornado of sex virtually. Her pussy started to moisten just at the thought of it. A permanent foursome? Maybe this wouldn't be so bad after all. She smiled a bit and looked at both women.

"I think if this is gonna work," Sara said getting a little warm in her neither regions, "we'd need to make sure we're all compatible with each other."

Cassandra smiled, knowing that she had her. She stood up and took Sara and Charlie by the hand, leading them down to the cabins below. With 12 orgasms, three daisy chains, and a fingerbang DP; the three sealed their new alliance.

Amazingly, the other girls really didn't notice that the three had gone. Gianna was trying to get everyone to take shots, Angela and Karlee were seducing one of the deck hands, the rest of the girls were playing in the pool, and Andy was once again alone with his thoughts. He snuck away from Alex and Natasha saying that he needed to pee. They offered to "help", but he managed to get to the head alone.

His talk with Sara earlier in the day had calmed him down some, but he still felt overwhelmed. The fog from the drinking wasn't helping much. He thought of diving into the water, but Captain Jane had asked that they not do that as it was dark out and could be dangerous. He splashed some cold water on his face and took a long look in the mirror.

He really saw nothing that special about him. He wasn't bad looking, but he wasn't gorgeous. He had pleasant traits, but it was nothing to write home about. The same thought kept coming into his mind, over and over again.

Why me?

He dried off and went back onto the deck, mostly trying to stay out of the way, watching everyone else. He leaned back on a couch, grabbing a stray water bottle he'd found and took some large gulps. He privately wondered how long it would be until someone noticed him and who it would be.

It wasn't who he'd thought it would be.

"Having fun?" Captain Jane asked coming to sit next to Andy on the couch.

"Yeah," Andy told her. "Just taking a breather."

"Kinda weird being the only guy surrounded by girls, huh?" Captain Jane surmised.

"I've been getting used to it," Andy replied while starting to hear the moans and words coming from the trio or Cassandra, Sara, and Charlie. Andy just rolled his eyes while Captain Jane was intrigued.

"They all seem to have a lot of energy, huh?" Captain Jane said, trying to keep it to small talk.

"That's an understatement," Andy said, the girls' moans starting to have an understandable effect on him.

"So," Captain Jane started, scooting closer to Andy, "what do you think of my crew?"

"They're great!" Andy said earnestly, "they seem to be on top of everything."

"Have they been top of you yet?" Captain Jane asked with a grin before laughing to break the tension. The look on Andy's face was enough to tell her the answer was no.

About the same time, one of the girls interested in Andy noticed he was on his own and decided to give him some more company.

"Hey guys!" Dillion said coming over toward Andy. "This is so great! Thank you, Captain, for everything!"

"Oh it's my pleasure! Dillion, isn't it?" Captain Jane asked, fully knowing her name as Dillion shook her head in the affirmative. Captain Jane loved porn and knew full well who all the girls on board were and was very intrigued by the tight-bodied Dillion, who she'd been eyeing from early on.

"This is Dillion's first time on a boat," Andy offered.

"Really?!" Captain Jane said. "Well I should give you the complete tour then. Interested?"

"Yeah!" Dillion said, excited to see more of the boat. "Come on, Andy!"

Andy obliging went with the duo, not really minding seeing more of the boat. Captain Jane took them everywhere from the laundry to the engine room, showing them everything she could think of. She even let them on the bridge, showing Dillion all the controls and switches she'd pointed out to Andy before. Captain Jane loved the young girl's curiosity.

As she'd planned, the final stop on the tour was her own cabin showing the pair the perks of being in charge. She went over to her personal bar ad offered both some of her private stock.

"This is lovely!" Dillion said, amazed at its luxury.

"Very nice," Andy agreed. "Perks of being the captain!"

"And the owner."

"Really?" both Andy and Dillion said simultaneously.

"Yep," Captain Jane said with pride, "she's my baby."

"That's so awesome!" Dillion said, amazed at the young captain/owner.

"Yeah," Captain Jane said wistfully, looking around. "Dream come true."

"Have you always been on the water?" Andy asked.

"Oh yeah," Captain Jane answered. "My dad had me on the water from diapers, anything that floated on the water, he took me on. I was hooked."

Dillion and Andy both sipped their drinks as they heard more and more about the captain's life story, both finding it fascinating. Captain Jane had other thoughts on her mind however, while showing them various things around the cabin.

"I even had the bed made special. Feel it," she encouraged. Dillion needed no encouragement and jumped onto the captain's bed, feeling its comfort immediately.

"This is really comfy," Dillion opined. Andy went over and felt the bed with his hand.

"Very nice," he said.

"Andy, you gotta lay down on it to get the full experience," Captain Jane told him. Dillion scooted over and Andy laid down next to her.

"Isn't that better?" Dillion asked him, with a twinge of evil in her voice. Andy nodded in agreement. Captain Jane smiled, things going according to her plan as she urged both to scoot over so she could also lay on the bed.

"Mmmm, so relaxing," the captain said, sinking onto the bed, always loving the comfort of it.

"Yes, it is..." Dillion said looking over Andy at the Captain. Andy had his eyes shut, but Captain Jane didn't. She saw the smile from Dillion and took it as a green light for what she'd intended, which it was. Captain Jane propped herself up and extended over Andy, Dillion matching her movements. Their lips collided and both moaned softly. Loud enough to get Andy's attention and open his eyes.

He now had a full visual of the lesbian make out session happening above him. The women were sensually massaging their tongues with each other, sort of a 'getting to know you' way. Captain Jane then used one of her hands to fondle Dillion's right breast, loving its firmness and bounciness. Dillion followed copping a feel of Captain Jane's breast. Her 32 C's felt like butter in Dillion's hand.

After a few minutes, the two broke off their groping make out session, smiling at each other. They then turned and looked down at Andy, both smiling wide. They descended on him, kissing and licking all over his face. Both women started rubbing his body, caressing and groping. Captain Jane quickly got her hands around Andy's cock. While it was true that she normally only slept with women, Andy was a definite exception.

Dillion was busy giving Andy a hickey, also whispering dirty talk to him.

"Isn't she hot?" Dillion whispered in Andy's ear, Andy only being able to nod in agreement.

"You wanna talk to me about hot?" Captain Jane asked before disengaging from Andy's crotch and moving over to Dillion's. She buried herself in the young girl's pussy, causing Dillion to squeal in delight. The captain clearly had skills as Dillion came to orgasm fairly quick. This did nothing to stop Captain Jane as she kept munching on Dillion's box.

Andy just watched the two women, content to be a spectator. His dick was still standing proud from watching the two and soon Dillion indicated to Captain Jane that Andy could use some attention too.