Chapter 05
27 December
Andy awoke and found that both women were still in the bed with him, spooned against each other. He thought it was sweet and cute. Then suddenly a voice boomed out.
"Breakfast!!"
He wasn't sure who said it, but it woke both girls up. They looked over and smiled.
"Guess we should get up then," Charlie said, moving out of the bed.
"I'm gonna pee," Andy declared, "I'll meet you guys out there."
"Ok," Cassandra said giving him a small French kiss. All three of them got out of the bed and Andy headed to bathroom. After a good pee, he moved to the door, but someone was already opening it.
"Good morning, Andy!" Alex said coming into the room.
"Morning," Andy said slightly confused why she was in there when breakfast was out there.
"Morning, Andy," Natasha said right behind her with a rolling tray of food.
"We decided that you should have breakfast in bed today!" Alex declared, gently guiding him back in the bed.
"Wow, that's really nice of you guys," Andy said surprised.
"It's our pleasure!" Natasha said as she got the trays out and started arranging the food.
The two had schemed to have breakfast prepared early, declare loud enough that it was ready, and then steal Andy for a private breakfast. Within 90 seconds of them walking in, Andy had a tray in front of him in the bed, eggs, sausage, toast, grapefruit, and coffee all prepared.
"Wow," Andy said astonished at their effort. "Where's your food?"
"Oh, we ate already," Alex said getting close to him. "This is all for you, baby," she said getting in the bed with him.
"You know, I don't think I've ever actually had breakfast in bed before," Andy hypothesized.
"Really?" Natasha said as she got into bed on the other side of him. "What lousy girlfriends you must've had," she theorized.
"No shit," Alex said inching closer and closer to him, "I know we would give our boyfriend breakfast in bed. Right, Nat?"
"Absolutely," Natasha concurred. "We know how to treat a man right."
Andy ate while thinking about Alex's slip of the tongue, for some reason saying 'boyfriend' instead of 'boyfriends'. He shrugged it off as the women kept prodding him.
"Is it good?" Natasha asked after he'd sampled everything.
"It's amazing!" Andy said glowingly. "Thank you so much, you guys!"
"It was our pleasure," Alex said getting closer to him and rubbing his leg. "Our absolute pleasure."
Andy didn't see, but Natasha had slipped down under the covers and soon found his cock, engulfing it in her mouth. Andy jumped a bit and saw Natasha's head under the sheets. Alex redirected his attention.
"Breakfast is the most important meal of the day," she told him while giving him a kiss. "Don't neglect it. Eat up," she insisted, "you'll need your strength..."
Andy had never eaten anything while getting blown before, so he slowly took a forkful of eggs and ate them. Alex smiled at him, continuing to snuggle up to Andy while Natasha blew him. Alex even took a piece of bacon and fed it to him.
"Now this is how a real man has breakfast," she said with a smile and then started sucking on his earlobe, "how you deserve to have it."
Natasha just kept right on sucking, fingering herself as she kept going. She loved the taste of Andy's pre-cum and licked it from the tip of his cock.
"Mmmm," Natasha said under the sheet. "He tastes so good, babe."
"Let me have a taste!" Alex said. Natasha came up and kissed Alex deeply, ensuring that some of Andy's pre-cum got into her mouth. They sucked on each other's tongues for a few seconds before looking at Andy and smiling.
"So, who would you like first?" Alex asked seductively while both girls let their hands roam all over each other.
"Uhhh," Andy said really unsure what to do. "I really don't know how to choose between you both."
Both girls smiled at his comment, knowing that it was exactly what they wanted to hear.
"There's no need to choose," Natasha said pushing him down and moving the tray, "you can have us both any time you want."
Natasha started kissing Andy and Alex squared herself over Andy's cock. Alex was soon impaled on top of him, and Natasha put her pussy over Andy's face. Both girls were soon in heaven as they were being satisfied by the man they loved. Alex was not shy about letting him know.
"ANDY!" she said loudly. "God, your cock is perfect! I love it so much!!!"
"Your mouth is so perfect, Andy!" Natasha said, humping herself against Andy's face. "Make my pussy feel loved!!!"
Andy, by now, was becoming adept at satisfying two women at the same time and this was no exception. Alex and Natasha looked at each other, fully satisfied with the man they wanted.
"Alex!" Natasha said mid-orgasm. "I love him so much! I want to keep him forever!"
"Keep us forever, Andy!" Alex said, also climaxing. "Make us your whores and keep us forever!"
Andy dismissed all of this as sex talk and just kept going. Alex soon got off to allow Natasha to ride. Natasha got on Andy reverse cowgirl and Alex started licking Natasha's cum from his face. She kept talking nasty and loving all at the same time to him.
"Look at her ass, Andy," she said. "Don't you want that ass every day? I want that ass every day. Give it a smack so she knows you like her."
Andy gently smacked at her ass and Natasha wanted more.
"Smack my ass, Andy!" she encouraged. "Make it red and make it yours!"
Andy responded with a few more healthy smacks, encouraging Natasha to ride him harder.
"Oh fuck, Andy!!" she said squealing in delight, "I love it so much!! You have the best cock ever!!!"
"He certainly does," Alex said licking and kissing Andy all the while rubbing his body up and down. "I want that cock forever."
"Ever and ever!" Natasha concurred as she gushed in orgasm, setting off Andy to spurt into her. "Oh GOD! Fill me, Andy! Claim it!!!"
Andy's body was shuddering from the force of his orgasm, and it was about a minute before Natasha, and he were both back to reality.
"Whoa," Alex said slightly shocked. "That was fuckin' intense!"
"Fuck yeah, it was!" Natasha said sliding off Andy's dick. Alex saw Andy's cum dripping from Natasha's pussy and immediately started lapping it up, causing mini orgasms in Natasha as she did.
"Mmm, that was tasty," she said returning to Andy's side.
"Me or his load?" Natasha asked with a smirk.
"Both!" Alex declared.
"You guys are unreal!" Andy said still panting a bit.
"That's just a warmup for what we have in store for you," Natasha whispered in his ear.
"All sorts of plans..." Alex concurred, kissing Andy on the cheek. Both girls got out of the bed, hand in hand, blew a kiss to Andy and were on their way. Andy just sat there stunned.
"Those fuckers!" Charlie said as Alex and Natasha had passed them in the hallway with Andy's breakfast.
"They definitely planned that out," Cassandra concurred, knowing that the breakfast call was false.
"Those two could very well scoop Andy up," Charlie concurred. "And don't forget about Angela and Karlee."
"I know," Cassandra said forlornly. Last night, they both seemed so close to getting Andy for themselves and now they were having to contend with two other duos who were after the same goal. Cassandra had at least made a decision on one important point. "We're in this together though," she told Charlie, taking her by the hand. Charlie smiled and gave Cassandra a deep kiss, sealing their pact.
The other girls saw what Alex and Natasha had planned. Gianna and Candace thought it was hilarious, the sisters wondered why they went to all that trouble, Liliana just shrugged, and the rest were pissed.
Angela and Karlee saw the two and were steaming. It was bad enough that Charlie and Cassandra stole him last night, but now Alex and Natasha got him for breakfast? They knew now what they had feared. Those two were not only trying to get Andy for the rest of the week, but beyond.
Sara was also upset, cursing herself for not thinking of it herself. She was now all alone and needed help. She felt lost and sad. She'd have to think of something to sway Andy.
Dillion was also depressed at the sight. She couldn't cook at all, so she knew that she couldn't've pulled that part off, but now she was stuck with all these other girls and no other support. She knew she'd have to be extra aggressive to get a leg up on the rest pursuing Andy.
Alex and Natasha came out soon with the breakfast tray and huge smiles. Natasha also had some of Andy's load dripping out of her pussy still, left there deliberately by the both of them.
"Nice breakfast?" Candace asked the pair with a smile.
"Yummy," Natasha said with a smirk.
Andy came out a few seconds later, with almost a guilty look on his face. Gianna couldn't resist.
"They fill you up or vice versa?" she said with a smirk. Andy went beet red. "There's my answer," she said cackling as Andy poured himself a coffee.
Dillion came up and kissed him Good Morning, making her sure her tight, flawless naked form was fully visible. "Are you excited for the boat?"
Today's activity was an excursion on a yacht with dinner on the sea. They were all told everything would be first class and everyone was looking forward to it.
"Definitely," Andy said as he took a sip.
"Have you ever been on a boat before?" Dillion asked innocently.
"Oh, yeah," Andy said, "I'm from Long Island, I grew up on them."
While Andy said it nicely, Dillion internally was crushed. She really should've known that, and it wasn't helping her toward her goal.
"I haven't really," she admitted, "but I sure feel safe knowing you'll be there to protect us."
"Aw shucks," Andy replied with a wink. Crisis averted, Dillion thought.
"We should go get ready," Sara opined trying to get to Andy. She was blocked.
"Yeah," Dillion said grabbing hold of Andy's hand. "Let's go!"
With that Dillion dragged Andy by the hand back into his room. Sara just stood there with her jaw on the floor. How stupid could she be to not be close to Andy before saying that? She just shook her head and went to go get ready.
Cassandra and Charlie saw Sara walk away sadly.
"I feel so bad for her," Cassandra admitted.
"Yeah, that was tough," Charlie admitted. "Her and Dillion are trying to get Andy and they're doing it by themselves."
That gave Cassandra a thought, as she looked at her friend walking away.
"Maybe we could help her," she said softly to Charlie. Charlie looked at her as if she'd lost her mind. Cassandra continued. "If she throws in with us, we now have the advantage over the rest."
Realization hit Charlie like a lightning bolt. Cassandra was absolutely right. Presenting Andy with a full, busty harem could be a clincher. Plus, Sara was an absolute knock out, and would have no trouble having hours of fun with her.
"Think she'd go for it?" Charlie said, now fully endorsing the idea.
"If we get her at the right time," Cassandra suggested. "We'll talk to her on the boat."
Dillion gave Andy a through washing, head to toe with plenty of head. Andy, likewise, was through with his washing, deciding to clean her pussy walls with his sperm, which Dillion gratefully accepted. They dried off and Dillion went to go change.
Andy looked in the mirror for a long time, thinking about how crazy the last few days had been and how the next few days were going to be. This was all supposed to be a lark. Just a 'what if' entry into a contest and now, he was surrounded by porn stars that seemed to want him constantly and were almost fighting for his attention. It felt unnatural to him. He needed to take better control.
He then got dressed in a polo and swim trunks and went back outside, seeing a variety of girls in various states of readiness. He didn't join them at first. He just leaned against the wall, trying to control the pace a bit of what was happening and what was to come.
"Watching the girls like a fuckin' creeper?" Gianna said coming up to him, wearing a very small bikini and a thin wrap. Not helpful.
"Not really," Andy told her, "just taking a few minutes."
Gianna looked in his eyes and saw distress. Completely unlike her, Gianna changed her tack completely.
"Are you ok?" she asked with what seemed like genuine concern which kinda surprised Andy.
"Yeah," Andy said with a sigh. "Just kind of a lot, you know?" clearly indicating the house full of women and he their primary focus.
"For most dudes, this is a dream come true," she said with confidence.
"Yeah, it just gets overwhelming. Hard to let things settle in my head."
Gianna nodded at him thoughtfully.
"I get it. No time to yourself and all us bitches constantly pawing at you."
"It's not like I mind," he told her, "just need to get a minute to myself to process it all."
"It'll ease up," Gianna said, lying. She was fully aware of the machinations of half the girls in the house and knew they would only get bolder in their pursuit of Andy. But he didn't need to hear that right now.
Soon, everyone was ready, and the party bus arrived to take them to the boat. They all piled in and again there was competition to sit next to Andy. Gianna decided to save him this time and sat next to him, Liliana joining from the other side. The other's pouted as they made their way down to the docks.
The boat was huge. A true yacht with deck chairs, sauna, jacuzzi, and every kind of alcohol imaginable. While some of the girls had no experience with boats, Andy quickly made his way down the jetty and boarded the boat. A lovely woman with captain's rank insignia greeted him.
"Welcome to the Atlantia!" she said warmly. "I'm Captain Jane and I'd like to introduce my crew." They looked over all the deck hands and all were surprised to find them to be all female and attractive. Some of the jealous feelings were emerging up, but everyone soon got settled and they cast off.
The girls were all impressed with how easily Andy walked the length of the boat, the motion not bothering him at all. While no one felt seasick, none of them really felt too comfortable moving yet. Once the boat was moving steadily, everyone started moving around and looking at all the sights. An attractive steward gave Andy a tropical drink as he took in the sea air. He knew of all the things he would miss about Long Island; the smell of the sea was high on the list.
Soon the women felt much more comfortable, most ditching their wraps or other coverings. Andy got a full tour of the boat and Captain Jane was quickly impressed by his knowledge. She showed him all the bridge controls, Andy being one of the few guys that didn't hit on her while she did it. The deck chairs were filled with all the women soon enough and Andy had many requests for suntan lotion. Some of the deck hands offered as well and the girls not in pursuit took them up on it as they all thought they were hot.
Alex, Natasha, Dillion, Cassandra, Sara, Charlie, Angela, and Karlee however had no such intention of letting Andy escape from his manly duties. He greased all the ladies up, some insisting on him covering as much of their bodies as possible given the crew's presence.
Captain Jane guided the yacht expertly into a secluded cove that most captains didn't know about, anchoring up at a shoal with crystal clear water.
"Everyone!" she announced stepping out from the bridge. "This is one of my personal favorite spots in the area. Its restricted so we should be left to our own devices here. Our crew will assist with anything you need or want. We have inflatables, jet skis, and other fun toys for you all. Enjoy!"
"Can we skinny dip?" Gianna shouted loud enough for anyone back at shore to hear. Andy went red but Captain Jane just smiled.
"Of course!" she said with merriment and Andy's surprised. "We're a pretty liberal boat here. Especially since there's only one guy here," she said pointing at Andy. "Feel free! The crew can join if they'd like!"
The girls, porn stars and crew alike, all cheered, and Andy just sipped his drink quietly. Bikinis were soon shed, and the staff went below to get out of their garments. Captain Jane started the party music going, smiling at everyone having a good time. The staff soon returned with appetizers and more drinks, now completely devoid of clothing.
The girls were all impressed, thinking that anyone one of them could certainly have a career in the industry. The girls started dancing around with the staff joining them. Most of the girls were just enjoying themselves, forgetting all about their plans on Andy for the moment. All except one.
"Having fun?" Sara said, finally getting Andy alone for a minute.
"Yeah," Andy said wistfully, sipping on his drink. "You?"
"I always have a good time when I'm with you," she replied giving him a kiss on the cheek, eliciting a side grin from him. "Are you sure you're ok?" she asked with some concern while hanging on his arm.
"I feel like my whole life has become nudity and sex in the last few days," he said earnestly. "Don't get me wrong, it's fun, and everyone's been great. But it's also overwhelming a bit."
Sara sighed, not really surprised at his thoughts. Honestly, she was surprised he'd handled all of it as well as he had.
"I get it," she said sympathetically, "you were supposed to have four other guys also occupying our time and now it's just you. It's gotta be a mind fuck."
"A bit," Andy said, nodding.
"I'm sorry," she said with sympathy. "But it is kinda fun, isn't it?" she added while pressing her body into his. He nodded his head a bit, acknowledging it. "Don't worry," she said wrapping her arms around him, "I'll keep you safe."
Andy sighed contently at her words, knowing that she meant it. By this time the other girls had also noticed the two of them. Cassandra and Charlie were the only ones who silently smiled, knowing that this would play in perfectly into their plan. The rest stewed.
The crew weren't sure why the vibe had suddenly changed, still just enjoying their fun guests. Almost all the crew went both ways and recognized the women as porn stars, figuring the guy was beyond rich. The crew slowly got the girls back to having fun, getting inflatables out and starting games.
Andy and Sara talked for a while about lots of things. The girls, life, work, hopes and dreams, even. She felt so much closer to Andy then before and knew that this was the man she wanted. Andy also felt really comfortable with Sara. Not as aggressive as the other girls and so easy to talk to. Sara looked behind her, seeing the other women contending for Andy all jealous. They all saw how comfortable Andy was with her and that she was not out of the running by any stretch of the imagination.
Andy cheered up some and joined the rest of the party, shedding his clothes just like the rest of them had. The staff were all impressed at his size as well as being impressed by him, personally. He didn't seem like a stereotypical rich guy who had a bunch of women around him. The staff were soon all warmly interacting with him as well, very pleased that he was respectful and kind.
Gianna and Dillion both availed themselves of the jet skis while many just swam in the warm water or played on the floats and slide. After a while, Captain Jane came down as well, equally naked as the rest. She had a very lean, athletic figure, Andy noted with full C-cup breasts and a heart shaped ass. She found Andy and went to see how he was doing.
"Having fun?" Captain Jane asked with a smile.
"Very much so, thank you," Andy said earnestly. "Your crew is so nice, fun, and professional." The captain's smile grew at his earnest complement.
"Thank you!" she replied. "It took a while to finally get this bunch together, but they've never let me down."
"I can tell," Andy said surveying the party unfolding, porn stars and boat staff.
"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.
"You should stick that in my pussy," Captain Jane offered.
"Ok," Andy said looking around the room, "do you have any condoms?" remembering that this woman was not under the protocols the porn stars had been in.
"I have an IUD and I'm clean as I know you are," she said, having talked to some of the other girls earlier about the disease protocols. "Just go for it."
Andy got himself up and behind Captain Jane, her pussy gleaning in the light coming through the porthole. He lined up and dove into the ship's captain, causing her to gasp at the new sensation. She immediately starting humping back at him, not letting up on Dillion pussy for a moment. Dillion was thoroughly impressed by the captain's skill but managed to look up and see Andy plowing Captain Jane from behind. She kept winking and teasing him with her tits.
Andy for his part looked at the scene before him and it turned him on more and more. Sure, he'd had more threesomes in the last few days then most men would ever dream of, but this one seemed so intimate. Like there was a clear connection between the three of them.
"Oh, FUCK!" Dillion howled at her orgasm from Captain Jane's attention. The captain wasn't far behind as Andy's cock seemed to be hitting all the right spots for her.
"SHIT!! ANDY!!!" as she collapsed from cumming harder then she had in a long while. She got her composure and found that Andy was still plugging away. She looked up at Dillion and smiled.
"Your turn?" she asked her.
"Fuck, yeah!" Dillion said excitedly. Captain Jane moved off of Andy's dick and Dillion laid down at the foot of the bed. He dutifully lined up his cock to her and plunged forward. "Mmmm!" was all that Dillion could say at Andy's cock being back inside her. He started off a bit slower than he had with the captain. Just gently thrusting into the young woman, her perky tits bouncing from the action.
The captain for her part was enjoying the show the two were putting on. This was one of the most erotic things she'd ever witnessed in her cabin, even more then the four-woman daisy chain she'd once entertained. She began making out with Dillion, their tongues dueling in a celebration of lust. Andy just watched the show and kept thrusting.
Captain Jane then sat up and straddled Dillion's face, her pussy resting on Dillion's lips. She then grabbed the back of Andy's head and pulled him in for a deep kiss. Dillion was apparently starting to cum given the constrictions in her pussy. This had a similar effect on Captain Jane as she started bucking hard against her mouth. Andy was still holding on, either from the tiredness or the booze, but he wasn't gonna last much longer.
"I'm gonna cum," he declared to anyone who cared to hear it.
"Cum in me!" Dillion requested, though muffled. Andy a few strokes later reciprocated, spilling his seed inside the young woman. He withdrew and collapsed on Captain Jane's bed, while she dove into Dillion's pussy to sample Andy's load. He drifted quietly off to sleep.
Andy awoke and found that both women were still in the bed with him, spooned against each other. He thought it was sweet and cute. Then suddenly a voice boomed out.
"Breakfast!!"
He wasn't sure who said it, but it woke both girls up. They looked over and smiled.
"Guess we should get up then," Charlie said, moving out of the bed.
"I'm gonna pee," Andy declared, "I'll meet you guys out there."
"Ok," Cassandra said giving him a small French kiss. All three of them got out of the bed and Andy headed to bathroom. After a good pee, he moved to the door, but someone was already opening it.
"Good morning, Andy!" Alex said coming into the room.
"Morning," Andy said slightly confused why she was in there when breakfast was out there.
"Morning, Andy," Natasha said right behind her with a rolling tray of food.
"We decided that you should have breakfast in bed today!" Alex declared, gently guiding him back in the bed.
"Wow, that's really nice of you guys," Andy said surprised.
"It's our pleasure!" Natasha said as she got the trays out and started arranging the food.
The two had schemed to have breakfast prepared early, declare loud enough that it was ready, and then steal Andy for a private breakfast. Within 90 seconds of them walking in, Andy had a tray in front of him in the bed, eggs, sausage, toast, grapefruit, and coffee all prepared.
"Wow," Andy said astonished at their effort. "Where's your food?"
"Oh, we ate already," Alex said getting close to him. "This is all for you, baby," she said getting in the bed with him.
"You know, I don't think I've ever actually had breakfast in bed before," Andy hypothesized.
"Really?" Natasha said as she got into bed on the other side of him. "What lousy girlfriends you must've had," she theorized.
"No shit," Alex said inching closer and closer to him, "I know we would give our boyfriend breakfast in bed. Right, Nat?"
"Absolutely," Natasha concurred. "We know how to treat a man right."
Andy ate while thinking about Alex's slip of the tongue, for some reason saying 'boyfriend' instead of 'boyfriends'. He shrugged it off as the women kept prodding him.
"Is it good?" Natasha asked after he'd sampled everything.
"It's amazing!" Andy said glowingly. "Thank you so much, you guys!"
"It was our pleasure," Alex said getting closer to him and rubbing his leg. "Our absolute pleasure."
Andy didn't see, but Natasha had slipped down under the covers and soon found his cock, engulfing it in her mouth. Andy jumped a bit and saw Natasha's head under the sheets. Alex redirected his attention.
"Breakfast is the most important meal of the day," she told him while giving him a kiss. "Don't neglect it. Eat up," she insisted, "you'll need your strength..."
Andy had never eaten anything while getting blown before, so he slowly took a forkful of eggs and ate them. Alex smiled at him, continuing to snuggle up to Andy while Natasha blew him. Alex even took a piece of bacon and fed it to him.
"Now this is how a real man has breakfast," she said with a smile and then started sucking on his earlobe, "how you deserve to have it."
Natasha just kept right on sucking, fingering herself as she kept going. She loved the taste of Andy's pre-cum and licked it from the tip of his cock.
"Mmmm," Natasha said under the sheet. "He tastes so good, babe."
"Let me have a taste!" Alex said. Natasha came up and kissed Alex deeply, ensuring that some of Andy's pre-cum got into her mouth. They sucked on each other's tongues for a few seconds before looking at Andy and smiling.
"So, who would you like first?" Alex asked seductively while both girls let their hands roam all over each other.
"Uhhh," Andy said really unsure what to do. "I really don't know how to choose between you both."
Both girls smiled at his comment, knowing that it was exactly what they wanted to hear.
"There's no need to choose," Natasha said pushing him down and moving the tray, "you can have us both any time you want."
Natasha started kissing Andy and Alex squared herself over Andy's cock. Alex was soon impaled on top of him, and Natasha put her pussy over Andy's face. Both girls were soon in heaven as they were being satisfied by the man they loved. Alex was not shy about letting him know.
"ANDY!" she said loudly. "God, your cock is perfect! I love it so much!!!"
"Your mouth is so perfect, Andy!" Natasha said, humping herself against Andy's face. "Make my pussy feel loved!!!"
Andy, by now, was becoming adept at satisfying two women at the same time and this was no exception. Alex and Natasha looked at each other, fully satisfied with the man they wanted.
"Alex!" Natasha said mid-orgasm. "I love him so much! I want to keep him forever!"
"Keep us forever, Andy!" Alex said, also climaxing. "Make us your whores and keep us forever!"
Andy dismissed all of this as sex talk and just kept going. Alex soon got off to allow Natasha to ride. Natasha got on Andy reverse cowgirl and Alex started licking Natasha's cum from his face. She kept talking nasty and loving all at the same time to him.
"Look at her ass, Andy," she said. "Don't you want that ass every day? I want that ass every day. Give it a smack so she knows you like her."
Andy gently smacked at her ass and Natasha wanted more.
"Smack my ass, Andy!" she encouraged. "Make it red and make it yours!"
Andy responded with a few more healthy smacks, encouraging Natasha to ride him harder.
"Oh fuck, Andy!!" she said squealing in delight, "I love it so much!! You have the best cock ever!!!"
"He certainly does," Alex said licking and kissing Andy all the while rubbing his body up and down. "I want that cock forever."
"Ever and ever!" Natasha concurred as she gushed in orgasm, setting off Andy to spurt into her. "Oh GOD! Fill me, Andy! Claim it!!!"
Andy's body was shuddering from the force of his orgasm, and it was about a minute before Natasha, and he were both back to reality.
"Whoa," Alex said slightly shocked. "That was fuckin' intense!"
"Fuck yeah, it was!" Natasha said sliding off Andy's dick. Alex saw Andy's cum dripping from Natasha's pussy and immediately started lapping it up, causing mini orgasms in Natasha as she did.
"Mmm, that was tasty," she said returning to Andy's side.
"Me or his load?" Natasha asked with a smirk.
"Both!" Alex declared.
"You guys are unreal!" Andy said still panting a bit.
"That's just a warmup for what we have in store for you," Natasha whispered in his ear.
"All sorts of plans..." Alex concurred, kissing Andy on the cheek. Both girls got out of the bed, hand in hand, blew a kiss to Andy and were on their way. Andy just sat there stunned.
"Those fuckers!" Charlie said as Alex and Natasha had passed them in the hallway with Andy's breakfast.
"They definitely planned that out," Cassandra concurred, knowing that the breakfast call was false.
"Those two could very well scoop Andy up," Charlie concurred. "And don't forget about Angela and Karlee."
"I know," Cassandra said forlornly. Last night, they both seemed so close to getting Andy for themselves and now they were having to contend with two other duos who were after the same goal. Cassandra had at least made a decision on one important point. "We're in this together though," she told Charlie, taking her by the hand. Charlie smiled and gave Cassandra a deep kiss, sealing their pact.
The other girls saw what Alex and Natasha had planned. Gianna and Candace thought it was hilarious, the sisters wondered why they went to all that trouble, Liliana just shrugged, and the rest were pissed.
Angela and Karlee saw the two and were steaming. It was bad enough that Charlie and Cassandra stole him last night, but now Alex and Natasha got him for breakfast? They knew now what they had feared. Those two were not only trying to get Andy for the rest of the week, but beyond.
Sara was also upset, cursing herself for not thinking of it herself. She was now all alone and needed help. She felt lost and sad. She'd have to think of something to sway Andy.
Dillion was also depressed at the sight. She couldn't cook at all, so she knew that she couldn't've pulled that part off, but now she was stuck with all these other girls and no other support. She knew she'd have to be extra aggressive to get a leg up on the rest pursuing Andy.
Alex and Natasha came out soon with the breakfast tray and huge smiles. Natasha also had some of Andy's load dripping out of her pussy still, left there deliberately by the both of them.
"Nice breakfast?" Candace asked the pair with a smile.
"Yummy," Natasha said with a smirk.
Andy came out a few seconds later, with almost a guilty look on his face. Gianna couldn't resist.
"They fill you up or vice versa?" she said with a smirk. Andy went beet red. "There's my answer," she said cackling as Andy poured himself a coffee.
Dillion came up and kissed him Good Morning, making her sure her tight, flawless naked form was fully visible. "Are you excited for the boat?"
Today's activity was an excursion on a yacht with dinner on the sea. They were all told everything would be first class and everyone was looking forward to it.
"Definitely," Andy said as he took a sip.
"Have you ever been on a boat before?" Dillion asked innocently.
"Oh, yeah," Andy said, "I'm from Long Island, I grew up on them."
While Andy said it nicely, Dillion internally was crushed. She really should've known that, and it wasn't helping her toward her goal.
"I haven't really," she admitted, "but I sure feel safe knowing you'll be there to protect us."
"Aw shucks," Andy replied with a wink. Crisis averted, Dillion thought.
"We should go get ready," Sara opined trying to get to Andy. She was blocked.
"Yeah," Dillion said grabbing hold of Andy's hand. "Let's go!"
With that Dillion dragged Andy by the hand back into his room. Sara just stood there with her jaw on the floor. How stupid could she be to not be close to Andy before saying that? She just shook her head and went to go get ready.
Cassandra and Charlie saw Sara walk away sadly.
"I feel so bad for her," Cassandra admitted.
"Yeah, that was tough," Charlie admitted. "Her and Dillion are trying to get Andy and they're doing it by themselves."
That gave Cassandra a thought, as she looked at her friend walking away.
"Maybe we could help her," she said softly to Charlie. Charlie looked at her as if she'd lost her mind. Cassandra continued. "If she throws in with us, we now have the advantage over the rest."
Realization hit Charlie like a lightning bolt. Cassandra was absolutely right. Presenting Andy with a full, busty harem could be a clincher. Plus, Sara was an absolute knock out, and would have no trouble having hours of fun with her.
"Think she'd go for it?" Charlie said, now fully endorsing the idea.
"If we get her at the right time," Cassandra suggested. "We'll talk to her on the boat."
Dillion gave Andy a through washing, head to toe with plenty of head. Andy, likewise, was through with his washing, deciding to clean her pussy walls with his sperm, which Dillion gratefully accepted. They dried off and Dillion went to go change.
Andy looked in the mirror for a long time, thinking about how crazy the last few days had been and how the next few days were going to be. This was all supposed to be a lark. Just a 'what if' entry into a contest and now, he was surrounded by porn stars that seemed to want him constantly and were almost fighting for his attention. It felt unnatural to him. He needed to take better control.
He then got dressed in a polo and swim trunks and went back outside, seeing a variety of girls in various states of readiness. He didn't join them at first. He just leaned against the wall, trying to control the pace a bit of what was happening and what was to come.
"Watching the girls like a fuckin' creeper?" Gianna said coming up to him, wearing a very small bikini and a thin wrap. Not helpful.
"Not really," Andy told her, "just taking a few minutes."
Gianna looked in his eyes and saw distress. Completely unlike her, Gianna changed her tack completely.
"Are you ok?" she asked with what seemed like genuine concern which kinda surprised Andy.
"Yeah," Andy said with a sigh. "Just kind of a lot, you know?" clearly indicating the house full of women and he their primary focus.
"For most dudes, this is a dream come true," she said with confidence.
"Yeah, it just gets overwhelming. Hard to let things settle in my head."
Gianna nodded at him thoughtfully.
"I get it. No time to yourself and all us bitches constantly pawing at you."
"It's not like I mind," he told her, "just need to get a minute to myself to process it all."
"It'll ease up," Gianna said, lying. She was fully aware of the machinations of half the girls in the house and knew they would only get bolder in their pursuit of Andy. But he didn't need to hear that right now.
Soon, everyone was ready, and the party bus arrived to take them to the boat. They all piled in and again there was competition to sit next to Andy. Gianna decided to save him this time and sat next to him, Liliana joining from the other side. The other's pouted as they made their way down to the docks.
The boat was huge. A true yacht with deck chairs, sauna, jacuzzi, and every kind of alcohol imaginable. While some of the girls had no experience with boats, Andy quickly made his way down the jetty and boarded the boat. A lovely woman with captain's rank insignia greeted him.
"Welcome to the Atlantia!" she said warmly. "I'm Captain Jane and I'd like to introduce my crew." They looked over all the deck hands and all were surprised to find them to be all female and attractive. Some of the jealous feelings were emerging up, but everyone soon got settled and they cast off.
The girls were all impressed with how easily Andy walked the length of the boat, the motion not bothering him at all. While no one felt seasick, none of them really felt too comfortable moving yet. Once the boat was moving steadily, everyone started moving around and looking at all the sights. An attractive steward gave Andy a tropical drink as he took in the sea air. He knew of all the things he would miss about Long Island; the smell of the sea was high on the list.
Soon the women felt much more comfortable, most ditching their wraps or other coverings. Andy got a full tour of the boat and Captain Jane was quickly impressed by his knowledge. She showed him all the bridge controls, Andy being one of the few guys that didn't hit on her while she did it. The deck chairs were filled with all the women soon enough and Andy had many requests for suntan lotion. Some of the deck hands offered as well and the girls not in pursuit took them up on it as they all thought they were hot.
Alex, Natasha, Dillion, Cassandra, Sara, Charlie, Angela, and Karlee however had no such intention of letting Andy escape from his manly duties. He greased all the ladies up, some insisting on him covering as much of their bodies as possible given the crew's presence.
Captain Jane guided the yacht expertly into a secluded cove that most captains didn't know about, anchoring up at a shoal with crystal clear water.
"Everyone!" she announced stepping out from the bridge. "This is one of my personal favorite spots in the area. Its restricted so we should be left to our own devices here. Our crew will assist with anything you need or want. We have inflatables, jet skis, and other fun toys for you all. Enjoy!"
"Can we skinny dip?" Gianna shouted loud enough for anyone back at shore to hear. Andy went red but Captain Jane just smiled.
"Of course!" she said with merriment and Andy's surprised. "We're a pretty liberal boat here. Especially since there's only one guy here," she said pointing at Andy. "Feel free! The crew can join if they'd like!"
The girls, porn stars and crew alike, all cheered, and Andy just sipped his drink quietly. Bikinis were soon shed, and the staff went below to get out of their garments. Captain Jane started the party music going, smiling at everyone having a good time. The staff soon returned with appetizers and more drinks, now completely devoid of clothing.
The girls were all impressed, thinking that anyone one of them could certainly have a career in the industry. The girls started dancing around with the staff joining them. Most of the girls were just enjoying themselves, forgetting all about their plans on Andy for the moment. All except one.
"Having fun?" Sara said, finally getting Andy alone for a minute.
"Yeah," Andy said wistfully, sipping on his drink. "You?"
"I always have a good time when I'm with you," she replied giving him a kiss on the cheek, eliciting a side grin from him. "Are you sure you're ok?" she asked with some concern while hanging on his arm.
"I feel like my whole life has become nudity and sex in the last few days," he said earnestly. "Don't get me wrong, it's fun, and everyone's been great. But it's also overwhelming a bit."
Sara sighed, not really surprised at his thoughts. Honestly, she was surprised he'd handled all of it as well as he had.
"I get it," she said sympathetically, "you were supposed to have four other guys also occupying our time and now it's just you. It's gotta be a mind fuck."
"A bit," Andy said, nodding.
"I'm sorry," she said with sympathy. "But it is kinda fun, isn't it?" she added while pressing her body into his. He nodded his head a bit, acknowledging it. "Don't worry," she said wrapping her arms around him, "I'll keep you safe."
Andy sighed contently at her words, knowing that she meant it. By this time the other girls had also noticed the two of them. Cassandra and Charlie were the only ones who silently smiled, knowing that this would play in perfectly into their plan. The rest stewed.
The crew weren't sure why the vibe had suddenly changed, still just enjoying their fun guests. Almost all the crew went both ways and recognized the women as porn stars, figuring the guy was beyond rich. The crew slowly got the girls back to having fun, getting inflatables out and starting games.
Andy and Sara talked for a while about lots of things. The girls, life, work, hopes and dreams, even. She felt so much closer to Andy then before and knew that this was the man she wanted. Andy also felt really comfortable with Sara. Not as aggressive as the other girls and so easy to talk to. Sara looked behind her, seeing the other women contending for Andy all jealous. They all saw how comfortable Andy was with her and that she was not out of the running by any stretch of the imagination.
Andy cheered up some and joined the rest of the party, shedding his clothes just like the rest of them had. The staff were all impressed at his size as well as being impressed by him, personally. He didn't seem like a stereotypical rich guy who had a bunch of women around him. The staff were soon all warmly interacting with him as well, very pleased that he was respectful and kind.
Gianna and Dillion both availed themselves of the jet skis while many just swam in the warm water or played on the floats and slide. After a while, Captain Jane came down as well, equally naked as the rest. She had a very lean, athletic figure, Andy noted with full C-cup breasts and a heart shaped ass. She found Andy and went to see how he was doing.
"Having fun?" Captain Jane asked with a smile.
"Very much so, thank you," Andy said earnestly. "Your crew is so nice, fun, and professional." The captain's smile grew at his earnest complement.
"Thank you!" she replied. "It took a while to finally get this bunch together, but they've never let me down."
"I can tell," Andy said surveying the party unfolding, porn stars and boat staff.
"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.
"You should stick that in my pussy," Captain Jane offered.
"Ok," Andy said looking around the room, "do you have any condoms?" remembering that this woman was not under the protocols the porn stars had been in.
"I have an IUD and I'm clean as I know you are," she said, having talked to some of the other girls earlier about the disease protocols. "Just go for it."
Andy got himself up and behind Captain Jane, her pussy gleaning in the light coming through the porthole. He lined up and dove into the ship's captain, causing her to gasp at the new sensation. She immediately starting humping back at him, not letting up on Dillion pussy for a moment. Dillion was thoroughly impressed by the captain's skill but managed to look up and see Andy plowing Captain Jane from behind. She kept winking and teasing him with her tits.
Andy for his part looked at the scene before him and it turned him on more and more. Sure, he'd had more threesomes in the last few days then most men would ever dream of, but this one seemed so intimate. Like there was a clear connection between the three of them.
"Oh, FUCK!" Dillion howled at her orgasm from Captain Jane's attention. The captain wasn't far behind as Andy's cock seemed to be hitting all the right spots for her.
"SHIT!! ANDY!!!" as she collapsed from cumming harder then she had in a long while. She got her composure and found that Andy was still plugging away. She looked up at Dillion and smiled.
"Your turn?" she asked her.
"Fuck, yeah!" Dillion said excitedly. Captain Jane moved off of Andy's dick and Dillion laid down at the foot of the bed. He dutifully lined up his cock to her and plunged forward. "Mmmm!" was all that Dillion could say at Andy's cock being back inside her. He started off a bit slower than he had with the captain. Just gently thrusting into the young woman, her perky tits bouncing from the action.
The captain for her part was enjoying the show the two were putting on. This was one of the most erotic things she'd ever witnessed in her cabin, even more then the four-woman daisy chain she'd once entertained. She began making out with Dillion, their tongues dueling in a celebration of lust. Andy just watched the show and kept thrusting.
Captain Jane then sat up and straddled Dillion's face, her pussy resting on Dillion's lips. She then grabbed the back of Andy's head and pulled him in for a deep kiss. Dillion was apparently starting to cum given the constrictions in her pussy. This had a similar effect on Captain Jane as she started bucking hard against her mouth. Andy was still holding on, either from the tiredness or the booze, but he wasn't gonna last much longer.
"I'm gonna cum," he declared to anyone who cared to hear it.
"Cum in me!" Dillion requested, though muffled. Andy a few strokes later reciprocated, spilling his seed inside the young woman. He withdrew and collapsed on Captain Jane's bed, while she dove into Dillion's pussy to sample Andy's load. He drifted quietly off to sleep.
- Next page: Chapter 06
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