The Prize Day 09

31 December

Gianna woke up and went for coffee. She got up early cause she and Candace had gone to bed right after she'd yelled at the other girls the night before. Part of her felt bad for it, but she felt protective of Andy now and wanted him to actually have a say in all this. Also, she saw that if things had kept going the way they were, there was gonna be a physical fight at some point.

She stretched out and got some coffee from the kitchen. As she poured the coffee into her cup, she looked back toward Andy's part of the house and wondered to herself if he was still there. She decided not to bother him, figuring if he was there, he needed some sleep. She sipped on the coffee and wondered what'd happened last night. She didn't listen on the discussion the other girls were having but wondered if they actually figured out their shit.

Staggering out of the bedroom in the back came Andy, grateful that it was Gianna there to greet him and not any of the women he'd yelled at the night before. He smiled meekly.

"Morning..." he said in an awkward tone.

"Hey there, killer," she replied trying to keep it light.

"I'm really sorry," Andy said right out of the gate. "I shouldn't've yelled at everyone."

"First off," Gianna said, wanting to make herself clear to him, "you were 100 percent right in what you said. Those bitches were acting crazy, and someone needed to smack them down."

"I just hope that you and Candace and Liliana..." Andy said while Gianna waived him off.

"We knew who you were talking to," she said, "we made them all talk their shit out in the living room."

"And?" Andy asked, wondering if what he'd done had any merit. Gianna just shrugged her shoulders, causing her massive boobs to bounce gleefully.

"Dunno," she admitted. "I let them talk that shit out."

"Huh," he said while Gianna slid him a coffee that he took gratefully.

"You sleep any?" Gianna asked him while Andy nodded.

"A bit," he replied. "Not well though."

"Andy?" they both heard from the side, seeing Natasha standing there. "Can we talk to you for a minute?"

Andy looked at Gianna and she indicated to him that he should, though she had no clue what the girls were gonna tell him.

"Ok," he said, taking his coffee with him, following Natasha. He soon was treated to a sight of women all sitting around the living room. Natasha joined Alex, Cassandra, Sara, Charlie, Angela, Karlee, and Dillion in the room. They all looked sad or remorseful while Andy looked them all over and started feeling guilty.

"Andy, we're so glad you didn't leave," Karlee said emphatically.

"Look," Andy said, trying to compose himself, "I'm sorry I blew up at everybody last night." Andy looked genuinely remorseful while the girls were all having none of it.

"Andy, you had every right to be mad," Sara said honestly. "We acted like bitches and have been for a while."

"Look, here's the thing," Angela said sitting up a bit. "We really all do love you and want to be with you," she admitted to him with the other girls all concurring. "But we realized that none of us really asked you what you want. So, we want to ask, all of us, what do you want?"

Andy stood there motionless, like a deer in the headlights, now fully on the spot. He'd thought about this long and hard all night, taking a deep breath as he looked over the group of gorgeous women in front of him.

"Honestly," he started, "I never even considered what I wanted. At first, I was just going along with what you guys wanted, trying to make up for the assholes from before and how they treated you guys." He got a series of warm smiles from the girls as he continued. "I'm attracted to all of you," he admitted, "and I think I could be happy with any or all of you. But is that what you want?"

The girls looked at each other pensively as Charlie spoke up.

"We've talked about it and we're willing to go along with whatever you want. If you want just one of us to be with, we won't stand in the way. If you want more than one of us, I can only speak for myself in saying I'd be game." The other girls nodded at this as Andy continued thinking.

"I guess the next question is, are you all planning on staying in the industry? I'm not saying that's a deal breaker or anything, just something to know."

The girls all looked at each other, knowing this would likely be a question asked of them as Dillion actually spoke up first.

"Well, I'm just starting off, so my answer is yes, I do."

"Me too," Karlee replied.

"Honestly, no," Sara said. "I think I'm done with it."

"Same," Charlie admitted, already thinking along those lines before the trip even started.

"I was planning to go more into solo and lesbian stuff," Cassandra said.

"I'm..." Alex started say, "I'm not sure."

"Same," came from Natasha and Angela.

"Ok," Andy said taking this all into account.

"Do you want us to quit?" Dillion asked.

"I don't want anyone doing anything they don't want to do," he stated honestly. "I'll be honest, performing with women I don't think would bother me," he admitted, "but for some reason, performing with guys may be a mental thing for me. I know..." he said holding up his hand to let them know he knew what they were gonna say, "I know it's just performing and doesn't mean anything, but I'm not sure that's something I get past. I'm really sorry."

All the girls appreciated the honesty he'd showed, but now they had to deal with reality. Dillion was the first to react.

"I understand," she said standing up and hugging Andy. "I'm just not ready yet. I'm sorry, Andy."

"There's nothing to apologize for," he said reassuringly.

"I'm sorry too, Andy," Karlee said standing up and hugging him too, making clear that she wasn't willing to leave the industry either yet. Angela was shocked, but understood, her career just starting. Karlee and Dillion then left the living room, thinking they should leave the rest to keep talking.

"Well, this is awkward," Andy said, still just standing in front of the remaining girls. They all giggled at the weirdness of the situation before Sara started talking again.

"So, what now?" Sara asked not just Andy, but the rest of the room.

"Here's what I think," Cassandra suggested. "You, me, and Charlie all said that we were willing to either leave or not perform with guys anymore, right?" Both girls nodded, while Cassandra looked at the other three girls. "And you three aren't sure yet right?" They all nodded again, wondering where she was going with this.

"What are you suggesting?" Alex asked flat out, "that we don't love Andy?"

"No, no, no," Cassandra said rapidly, trying not to start another fight, which Alex saw. "What I meant was that you're not sure yet about the industry, not Andy."

All three women instantly relaxed, feeling the sincerity in Cassandra's words and accurately stating their position. All three nodded toward Cassandra as she continued.

"I think that you three should really think and decide what you want to do," Cassandra said conservatively, knowing that it could come off as bitchy. "None of us," she said indicating Sara, Charlie, and herself, "will do anything to influence or sway Andy. Which reminds me," she said turning back to Andy, "Andy, are you willing to be with all of us?"

"All of you?" Andy asked again, for clarity.

"Possibly," Alex said, while still unsure, hopeful.

"Jesus..." he said to himself, now having it right in front of him.

"Are you ok?" Sara asked out of concern.

"It's just a lot," he admitted. Of course, in theory, he knew this was a possibility with so many groups all vying for him that he would be in a non-traditional relationship, but now the reality of it was stark in front of him. He took a deep breath trying to keep his wits about him. "I mean, I'm willing to try it," he said with some hesitation and completely unsure of himself. "Is that what you all want?"

The girls looked at each other, letting Charlie speak up.

"Look, Andy, I really do love you," Charlie said, saying plainly what was in her mind, "but I've also fallen for Cass and Sara too. Sure, I've performed with girls, but it was always just that. Now..." she said looking at the two lovely women.

"Same," Cassandra said as Sara hugged Charlie to let her know her feelings as well. "I think we could all," Cassandra said, also looking at Angela, Alex, and Natasha, "be very happy together if that's what they choose."

"Would anyone get jealous?" Andy asked, "cause here's the thing. I don't want to wind up as some pawn again. I don't want to be something to fight over. That'll just tear everyone apart and I'll just wind up alone again."

"NO!" all the women shouted at the same time. Natasha quickly got up and sat next to Andy.

"Andy, you will never be alone again, that I promise you," Natasha said, taking Andy's hand into hers. All the other women nodded as well. "You are so wonderful and thoughtful and caring," she said looking into my eyes with affection. "I've made up my mind, I wanna throw in with you, if that's ok with all of you?"

Cassandra, Charlie, and Sara all looked at each other and smiled and soon there was a group hug in the middle of the room with all four of the girls. After a few seconds, Sara beckoned to Andy to join them, which he did amidst the hugs and kissed.

"I'm in too!" Alex said joining the hug trying to suck as much of Andy's face up as possible, one second of which made her know that she made the right decision. Angela fidgeted in her seat for a moment, but the sight of so much beauty and Andy at the center of it was more than enough to get her to join them all.

After the session in the living room, peace had finally returned to the house for their last full day. The girls were all getting along, and Andy felt at ease. He still wasn't fully sure how the future would look with all these women in his life, but he wasn't in fear anymore. There was pool time, laughing, and genuine joy. Even dinner was nice, everyone talking happily with more than enough innuendo for both the girls and Andy.

It was about nine when Gianna called everyone into the living room and had Andy sit in a chair in the middle of the room. He sat down as Gianna placed a blindfold on him.

"So, we're gonna play a fun game called "Guess the Pussy!" she declared. "I'm gonna get you hard," Gianna explained to Andy, "then we're gonna have a girl ride you, anyway they want. You get three guesses a pussy, if you guess right, they're eliminated, if you guess wrong, they get to spank you."

"No pressure there..." Andy said both aloud and to himself.

"Oh, relax," Gianna said, slapping his arm lightly while laughing, "it's gonna be fun."

Once Gianna was convinced that Andy's blindfold was firmly secure, she got to work on getting him hard. While her oral skills may not have been up to the level of Charlie's, they were still very skilled, using suction and saliva to have Andy's totem pole at full readiness.

"Ok," Gianna said, getting up from her position between his legs, "it's time for our first rider."

Andy felt motion happening and he soon felt a woman straddle him, grab his cock and guide it into her pussy. He noticed it wasn't as tight as others, so he quickly discounted the younger girls. She was riding him with full vigor and passion, it seemed to him. Since his hands were free, he allowed himself a feel of the woman's ass, trying to make a determination. After a few seconds of groping, he made his first guess.

"Nat?" he asked out loud.

"Fuck!" Natasha said getting off his cock, knowing she'd been defeated. She went around to his side and whispered in his ear, "I'm glad you know what I feel like."

"Next!" Gianna bellowed, another rider impaling herself on his cock. She was tighter then Natasha and lighter. She put her hands on his shoulders, really wanting to make the most of this ride. She did her best not to moan, worried that her voice would give herself away. Andy noted the thin frame and figured there were two guesses to make.

"Dillion?" he asked, hearing a resounding no and a strike one from Gianna. "Liliana?" however got the cheers and Liliana promptly got off of him, having finally had Andy's dick in her.

"Next bitch up!" Gianna said as another girl came up. She got on him quickly and started riding away. This girl was riding him like she was escaping a posse. He notice that she was heavier than the previous two, feeling a meatier ass against his lap. He could also feel a heavy pair of tits hitting my face, and suddenly he knew.

"Gianna," he said simply, getting cheers from the girls.

"Fuck!" she bellowed getting off of his lap, as the rest of the girls laughed. Andy himself was smiling at it all, even Gianna's frustration. And so it went for about a half hour. Andy was more accurate then he thought he'd be, even impressing some of the girls too. The only ones who Andy couldn't guess were Brittany and Sara, Sara being a little pissed her man couldn't guess her cunt.

It was decided that Brittany and Sara deserved a cum bath for "winning" and Andy quickly covered the two in his seed, having been fairly worked up from all the fucking he'd endured. It was that scene that Captain Jane and her crew walked into.

"Damn," she said with a smile, "seems like we missed the show!"

Andy was shocked to see her and moved to cover himself a bit, an idea he later realized to be ridiculous. Dillion went over to Jane and gave her a hug, neither seeming to be upset at the nudity.

"I'm glad you got my text," Captain Jane said with a smile.

"What happened?" Andy said, having found a pillow to cover up a bit while Whitney got towels for her sister and Sara. "I figured you'd have a big charter for New Year's."

"Cancelled," Captain Jane said with a shrug. "I reached out to Dillion to see if we could join the festivities. That is, if you guys don't mind..."

All the women cheered, and Captain Jane and the crew were soon naked. Candace got the music going through the house, drinks seemed to come out of nowhere, and soon everyone was dancing and having a fun time. Andy had managed to extricate himself briefly to go to the bathroom, with more than a few of the women offering to "help" him out.

He managed to get to his bathroom alone, took a pee, and then looked at himself in the mirror. 'How the hell did I get into all this?' he thought to himself, looking at the dizzying prospects before him. Not so much the current party, which he had no doubt was soon to become a full-blown orgy, but after.

At least six of the women there had told him that not only were they in love with him, but they also all wanted to live with him! Part of him thought it was the island atmosphere, that all of this would blow over when they all got to their respective homes and had a chance to think. For the moment, however, he decided he would make the most of his last night there. He looked at the mirror, smiled, and headed back out.

True to his prediction, while some of the girls were up and dancing to the music, others had broken off into various groups and started having fun. Andy saw that a box of sex toys was now out, with a variety of dildos, strap-ons, and devices that Andy couldn't even recognize. Karlee was using a double dildo with one of the yacht stewards, Angela sucking on her tits while playing with her own pussy.

Alex and Natasha both had strap-ons on while spit roasting a steward, high-fiving each other as they did. There was also a massive daisy chain that involved the Stevens Sisters, Cassandra, Charlie, Captain Jane, Sara, Candace, and a random deck hand all licking, nibbling, and sucking on each other.

Part of Andy thought he should maybe slink away, letting them have their fun, and he could go in the pool and relax, maybe join them closer to midnight. Gianna put a quick end to that.

"ANDY!!!" she shouted loud enough that Andy thought the whole island heard her. She extended her arms to him, getting him to come over and start dancing with some of the crew and Liliana. "This shit is legit!!"

He was soon surrounded by girls on all sides, all of them seeming to grind on him with various body parts. After a few minutes of this, Andy was dehydrated and needed a water. It probably took him another two minutes just to extricate himself from the mass of women and get over to the fridge and grab a water bottle, chugging it down pretty hard.

As he put the bottle down, he felt a soft pair of tits at his back and arms wrapping around his front.

"How are you?" he heard Alex ask him from behind.

"I'm good," Andy said, taking another swig of water.

"I just love you so much," Alex admitted, finally relieved that she could finally properly tell him her feelings. "I can't wait to start our lives all together."

"Really?" Andy asked, turning toward her. "You're really ok with all this? All of us together?" Alex took a deep breath, still holding onto Andy.

"I'm not saying it's gonna be easy," she admitted. "But I'd rather have part of you then nothing at all. Andy," Alex said softly, taking his hand into hers, "I had no idea what to expect from this week. I never planned on you. I never planned on falling for you. But I'm really glad it did."

"You know what, me too," Andy said with a smile as Alex smiled and kissed him. Just then, they were interrupted.

"Can't keep him all to yourself," Cassandra said with a smirk coming over to join the duo. Alex just smiled and kissed Cassandra deeply. They all knew if this had any chance of working, the women were gonna all have to be comfortable with each other and by Andy's eyes, Cassandra and Alex were off to a good start. They then turned to Andy and smiled, Cassandra now kissing Andy deeply.

"Come on," she told him, and also Andy, "your lack of presence has been noticed. Both girls hooked an arm to him and led him back to the living room. By this time, the scene had devolved into a full-on orgy, moaning and grinding everywhere. There were now two separate daisy chains going on with a mix of porn stars and yacht crew all enjoying each other's talents.

Captain Jane was rocking a strap-on and plowing Karlee at the moment, who herself was eating out Whitney. Captain Jane saw Andy and smiled.

"There he is!" she said while continuing to thrust her fake cock into the young star. "Wanna fuck me while I fuck her?"

"Uh..." Andy was able to say before Alex and Cassandra pushed him forward, thinking this could be a fun show. Captain Jane smiled and leaned forward a bit allowing Andy access to her snatch easier, even with the straps of the hard-on in the way. Tentatively, Andy got behind her and sunk into her pussy, it already being red hot from the scene in front of all of them and fucking Karlee.

Andy had no reason to be gentle as he quickly started thrusting into the yacht captain, who used the extra energy to fuck Karlee even harder. Both women were now screaming, Karlee for Captain Jane and Captain Jane for Andy.

"Fuck Andy, pound that tight pussy!" Captain Jane screamed out loud enough to get the attention of the group. The crewmembers looked at Andy fucking their captain, having never seen a man fuck her before, while the rest were all looking at Andy, fucking a girl wearing a strap on. Alex decided to join the trio by licking Andy's ass as he plowed the captain while Cassandra decided to have Karlee lick her pussy, which Karlee was more than willing to do.

Andy was now in the middle of a five-way and was astounded that something like this was happening. Sure, he might've thought he might get laid at some point in this trip, but nothing like this. While some of the girls were still playing and teasing with each other, most were focused on the five of them going at it.

Captain Jane didn't take much to cum from all this and she clamped onto Andy's cock and sprayed it with her cum. The sight caused Karlee to cum, and Cassandra followed in suit. Seeing all this cumming all at once caused Andy to get close. Not being one to be rude, Andy started to let the captain know what was coming.