The Prize Day 01

Author's Note:

This is a work of pure fiction. All characters are inspired by real individuals but are not meant to bear their true selves. As always, all persons are 18+. This will be a multi part series and I hope you all enjoy!

Jamaica, 23 December 2012

Andy Benedict had just landed in Kingston, and he was already overwhelmed. He had never been out of the country before, and it was so different to him. So vibrant, crowded. Everyone spoke English of course, but that was not why he was nervous. This trip was the craziest thing he'd ever been a part of. He still couldn't believe he was doing this.

He still couldn't believe he won.

Two Months Previous

Andy was sitting at home, alone as usual. He lived alone and only really went out when his friends called him up. It was Tuesday and there were no bar trips tonight. So Andy was doing what most people do. Streaming shows on the TV and watching porn on his laptop. This was pretty normal for a weeknight for him. While "tooling" around his favorite site, he saw a streamer on the top.

"Holidays with the Stars!!"

This got Andy's attention a bit. Mostly out of boredom, he did what he never did. He clicked on a porn ad.

"Win the vacation that all men cream over! You could win a chance to spend Christmas and New Year's with 15 of your favorite porn stars!! You will fly first class to Jamaica and then be ferried to a grand villa via helicopter! You and your favorite stars will spend the holidays playing, exploring, swimming, boating, and "getting to know each other" all while enjoying warm tropical weather! Enter now for a chance for to have a holiday vacation Santa would be jealous of!"

A vacation with porn stars! It didn't name any, but it was still interesting. One thought was first.

No way this is as good as it sounds.

Then came the other thought.

Why not try?

Andy signed up using a dummy e-mail that he only used for porn verification. He had to give a phone number, which he wasn't crazy about; but he was moving after New Years' anyway and it wouldn't follow him there. He then went back to perusing his favorites, finishing off, then sleep.

One Month Previous

Andy was getting packed for his trip to Mom's for Thanksgiving dinner. He just about had everything in the bag when his phone rang. He didn't recognize the number but decided to pick up anyway. Andy sometimes got a kick out of annoying telemarketers.

"Hello?"

"Hi there, is this Andy Benedict?"

"Yes, it is, may I ask who's calling?"

"Andy, this is Bob Logan with Adult Metro Promotions. I'm calling to tell you that you are the lucky winner of the "Holidays with the Stars" contest!!!"

Andy blinked a couple of times in disbelief. He'd completely forgotten that he signed up for the damn thing.

"Oh, oh wow. Thank you."

"Absolutely, Andy! I'm sure you're very excited. Just a few quick things we need to go over, if you have some time?"

"Uh, yeah. Go ahead."

"Andy, first I need to ask you, do you have a passport?"

"Yes, I do."

"Great! And do you still live on Long Island?"

"Yes, Huntington."

"Fantastic! We are going to be sending you an e-mail in the next couple of minutes with a medical form. We need you to be checked for any STD's or anything else, before we book your tickets. There will be a list of approved doctors local to you and the tests will be done at no cost. Once we have the form back from the doctor's office. You'll be good to go!!"

Andy politely finished the call and hung up. He was in shock. He grabbed his laptop and opened up the mailbox of his dummy account. Sure enough, there was a medical form and several local doctors. He saw one was right down the street and gave them a call. They were able to get him in right away, so he printed out the form and headed over. They took blood and ran through all the tests necessitated by the form. The receptionist said that they would send it off as soon as the results were in. Thankfully, the form didn't say what it was for or who the company was.

Two Days Later

Andy was sitting at Mom's enjoying a cup of iced tea after a nice lunch. His mom always took care of him when he was home, when she wasn't pushing him to date more or give him grief about moving all the way to Las Vegas early next year. He was nice and polite about it all, but still hadn't told Mom about the contest. He wanted to wait until the test results were came in before upsetting her. It wasn't like Andy thought he had an STD; he was just being extra cautious. Plus he figured it would be easier to break this news to Mom over the phone.

Suddenly his phone rang, and Andy recognized the number from the other day. He told his mom that a work call was coming in and would need to take it outside.

"Hello?"

"Andy! Its Bob Logan again with Adult Metro, how's your Thanksgiving?!"

"Good, thank you. Yours?"

"Couldn't be better! You have a few minutes to talk?"

"Sure."

"Great! I'm calling to let you know that we just got the test results in and you are all clear to go! We're gonna send you an e-mail on your flight information. It'll be a first-class direct flight from LaGuardia to Kingston where you'll be met by me to be taken over to the villa. Now there will be four other gentlemen going along on this trip. They are the paid customers, but don't worry there won't be any distinction in how you're treated. When you arrive, I'll have you sign a contract of conduct and other things, and you'll get to meet the other gentleman there!"

"Ok, is there a way I could get a copy of that contract before so I can just give it a quick review?"

"Absolutely! I'll send a copy to you as soon as I get off the phone."

That made Andy feel a bit better about all of this. They shared a few more pleasantries and ended the call. A few minutes later, Andy got an e-mail with the contract. He looked it over and saw nothing out of the ordinary. There was nothing about cameras in the house or some kind of surprises awaiting, which is what worried him to start with.

Time to tell Mom......

Kingston

Andy kept heading through the terminal until he saw a large gentleman in a suit holding a sign with his name on it.

"Excuse me, sir. I'm Andy."

"Hello, Mr. Benedict, I'm Jerome. Could I see your identification really quick please?"

He reached into the bag and pulled out the passport that he had just used for the first time 10 minutes ago. Andy handed it to Jerome who looked it over and checked it to his face. He then smiled and handed it back.

"Thank you, sir. Will you follow me please?"

Andy began to walk with Jerome.

"Do you have any luggage, sir?"

"No," Andy answered. "Just the duffle bag here."

"I'll carry your bag, sir"

"That's ok, I got it; thank you, though."

He nodded in appreciation, and they continued walking. Eventually they made their way to a helicopter pad area and Andy saw a gentleman with a clipboard. He saw them and immediately smiled.

"Andy! Good to meet you in person! Bob Logan," extending his hand.

"Good to meet you."

"Just need you to sign the contract really quick and we'll be all set." Bob then handed Andy the clipboard he'd been holding.

Andy looked it over and saw that it was the same contract as before. He identified all the benchmarks and found it to be exactly the same. He signed and handed it back to Bob.

"Great! Come with me!"

They walked into a small area with two other guys already seated.

"Andy," Bob introduced, "This is Kevin and Hunter. Gentleman, this is Andy."

Andy went to shake their hands but only got up nods from them. They looked like douchebags and seemed like the entitled types. Bob then directed Andy to a seat. Bob then got up and talked.

"So, a few things before we head out to the villa guys. First, originally it was going to be the five of you with 15 stars. There has been a late change from yesterday."

Andy figured something like this was coming and rolled his eyes.

"The other two gentleman that were to come cancelled." Andy immediately sat up a little more.

"Apparently, they booked this for a bachelor party and the intended's fiancé found the e-mail. So, it will just be the three of you for this!" Andy just nodded as Bob continued.

"I just want to go over a few of the ground rules again with you guys. I'm sure you all know them by now, but I want to make sure I stress them. The girls are under no obligations to sleep with you, perform sexual favors or anything of the kind. But, if they so choose, all are tested and are on birth control; so have no concerns there. Any attempt to coopt them against their will result in your trip being ended and you being immediately sent home without refund. Any unwelcome advances or aggressive activity will be dealt with swiftly by Jerome, who you've already met," indicating back to where Jerome was smiling.

"Other than that, I'm sure the girls can't wait to meet you guys, so let's head out!!"

With that, they all got up and boarded the helicopter. Andy tried several times to strike up a conversation with the douchebag twins, but they were too busy talking about the "crazy pelt" they were gonna get for the next week. Andy mostly talked to Jerome instead most of the ride, his first in a helicopter. He was a New Yorker too, the Bronx. Talked about the Jets and Knicks sucking mostly before they reached their final destination.

Andy got his first look at the place and was in awe. The house was enormous, huge patio with swimming pools and hot tubs. It looked like paradise. He half expected George Clooney to be on the front lawn. The douche brothers didn't look as impressed and thought it should've been nicer. Andy just rolled his eyes as the helicopter landed softly on a small pad near the house. Bob got out and got us together.

"Ok, guys. Here it is! There is a full staff that works on the other property you saw on the way in. The meals and everything will come from there. The girls are waiting to meet you if you're ready!"

Kevin and Hunter just high fived each other and Andy just followed them all into the house. The sun was starting to begin its setting phase as they entered the house. They all heard giggling and whatnot coming from inside and then someone shushing everyone. They turned a corner and there they were.

15 gorgeous women dressed seductively, but not slutty. Kevin and Hunter just looked them up and down. Andy was in awe. Bob got in front so that he could make the introductions.

"Well gentlemen, here are your roommates for the next week or so. Ladies, why don't you introduce yourselves to your bunkies!" They started from left to right.

"Hi, I'm Sara." As if Sara Stone needed the introduction, her perfect boobs and beautiful smile said it all.

"Hi, I'm Charlie." Charlie Chase was a blowjob queen with tits and ass that wouldn't quit with a restraining order. She was also one of the loudest performers Andy ever saw. He had to turn the volume down more than a few times on some of her scenes.

"Hi, I'm Alex," said Alex Chance. A bigger girl, but with a rack that could make any man drool.

"Hi, I'm Natasha." Natasha Nice, the French born porn actress with dazzling eyes. Plus DD's and a fine ass.

"Hi, I'm Whitney and this is my sister Britany." The Stevens sisters. Infamous for performing together.

"Hi, I'm Candace." Candace Von smiled and waved while her ebony curves enticed.

"Hi, I'm Gianna." The goddess herself Gianna Michaels. Tall, busty, and balsy.

"Hi, I'm Cassandra," said Cassandra Calogera. One of Andy's absolute favorites.

"Hi, I'm Sasha." Sasha Knox, maybe not as busty as the rest, but her ass was worth a human sacrifice.

"Hi, I'm Karlee." Karlee Grey was brand new to the industry, but with very womanly curves.

"Hi, I'm Liliana." Liliana Moreno hadn't done much in the industry, but she was eager and adorable.

"Hi, I'm Dillion." Dillion Harper was also a new "cummer," but her tits looked so cute and perky, it was heart melting.

"Hi, I'm Melanie." Melanie Hicks was another "bigger" girl. She had done a lot of taboo productions that Andy watched.

"And hi, I'm Angela." Angela White, the legendary Australian performer known for F cups and giving no "F's"

"Ladies," Bob took up, "This is Kevin, Hunter, and Andy."

Hunter and Kevin just licked their lips and made some obscene looks with their faces. Andy just nodded politely and the assortment of women and was surprised that some paid him attention back with looks, rather than the duo of douche.

"Well," Bob interjected, "The girls are going to get ready for a welcome party here in about 15 minutes. Why don't I show you guys to your rooms, and you can freshen up before the party?"

Andy again nodded and indicated a goodbye to the women while Hunter and Kevin were still making lewd exchanges. He was surprised that more than a couple of the women winked and looked at him favorably. Bob escorted Kevin and Hunter to their individual suites. He then turned to Andy.

"So, originally we were going to put you into one of the "junior" suites, but since the other two guys backed out; you get the upgrade!"

Bob showed Andy his room with a great view of the water, California King bed if not larger, and a private bathroom with a huge bathtub and a large shower. Bob clapped Andy on the back.

"Well, I'm gonna head out, Andy. You freshen up, enjoy your vacation, and take care!"

Andy shook his hand, and he left the room. He found his bag already in there and started to unpack. Mostly he had shorts and bathing suits, but he also thought enough ahead to pack nicer clothes. He rinsed off quickly in the shower, cleaned up and threw on some clothes. He took several deep breaths and then left his room. He headed to where the music was and saw a sight.

All the girls were there in the same outfits they'd been. A few were over with Hunter and Kevin and seemed to be placating them, the rest were hanging out amongst themselves just grooving to the music. He saw Jerome again hanging by the bar and went over to say hi.

"How's it going?" Andy inquired.

"Hey, Andy," Jerome greeted him, finally dropping his formal stance with him. "Just keeping an eye out and watching these two," indicating the wonder douches. "They better slow down and keep themselves in check," he warned. "How are you doing, man?"

"Doing good, just gonna make myself a drink. Want anything?" Andy inquired. Jerome appreciated the gesture.

"Naw, man. Gotta rock the water on duty. You enjoy," as he walked away.

Andy took stock of the bar and mixers and was very impressed with the drinks available. Then he saw the mixers and found a bottle of Limeade. Andy immediately smiled and pulled it out. He grabbed the gin and started making one of his favorite drinks.

"Andy, right?" said the inquiring Alex. Andy smiled back, slightly nervously. After all, he'd never been this close to a porn star before.

"Yeah, hi. How are you, Alex?" She smiled that he remembered her name. Stage name, anyway.

"I'm good, thanks. What are you making?"

"Well, since I saw the limeade here; I thought I'd make one of my favorite drinks." Alex watched as Andy mixed the limeade with the gin, not knowing what he was thinking. Andy took a sip of it and was pleased with the result. "Jericho Turnpike," Andy explained.

"Can I try it?" Alex inquired.

"Sure!" Andy insisted handing her the drink. Alex was normally on her guard when people handed her drinks, but she saw Andy make it and knew he didn't add anything to it. Also, he had sipped it himself. She took a sip and was amazed.

"Holy Fuck! That's really good!" Alex praised.

"Yeah, the tart of the limeade helps the gin be more palatable," Andy explained. "You can have that one, if you'd like."

"Oh, no. I don't want to take your drink," Alex insisted.

"Please, go ahead," Andy insisted. "I'll make another one."

"Oh, thanks. That's really nice of you," Alex commented.

"Don't worry about it," Andy retorted with a slight smile and started making a new drink.

"Whatcha drinkin?" Charlie inquired.

"It's a drink Andy made me, called a.... what did you call it?"

"Jericho Turnpike," Andy replied.

"He made it for himself and let me have it, wanna try?" Alex inquired.

Charlie took the drink and had a small sip. Her eyes went wide with how good it was.

"Wow, that's pretty fuckin good!" Charlie critiqued. "Any chance you'd make me one?"

"Sure, have this one," Andy insisted giving Charlie the drink he just made himself. He took a sip of it first to make sure it was up to his standards. Charlie saw this and thought the same as Alex, that he was showing he didn't put anything in it. She, like Alex, appreciated the gesture and took the drink.

"Oh my God, those guys are arseholes," Angela declared making her way to the bar. She was somewhat careful to only be heard by those at the bar and not them. "They can't stop trying to grab my tits and put their hands on me!" Angela complained. Andy heard this and interjected.

"Classy individuals." Everyone at the bar laughed at that and diffused the tension somewhat. Andy decided to keep an eye on the two and saw that they were being dicks, but for the moment, keeping their hands to themselves.

"Ange, try this," Charlie insisted. Angela took the drink and liked it immediately.

"I needed that," releasing some of the stress she had. "That was really good, you make that?" Angela asked Charlie.

"Andy made it," Alex answered. "We kinda turned him into our own little bartender," she said joking/seriously.

"I'd be happy to make one for you if you'd like," Andy offered.

"Thank you! I appreciate it," Angela answered, watching Andy make the drink. She couldn't help thinking that this guy was so much nicer than the other two fucktards. Andy again sipped the drink to make sure it was good and gave it to Angela. Then, Andy was finally able to make his own drink.

"Let's all grab the couch over there so we can sit down," Charlie suggested. "Otherwise, we'll have poor Andy up here all night and he'll never get a drink."

Everyone laughed a bit and Andy agreed. He grabbed his drink and came from behind the bar. Alex took him by the hand and led him to the couch with Angela and Charlie following. Even the hand grab had Andy's dick twitching a tad. They all say down and got comfortable.

"So, where are you from, Andy?" Charlie inquired.

"Long Island," Andy answered.

"Oh, where is that?" Angela asked. Being Australian, she had no idea where a lot of things were in the states.

"New York, near the city," Andy explained.

"Ooh! That sounds fun," Angela said.

"Yeah, but I'm actually moving to Vegas soon for work."

"Nice, my territory!" Alex said. "What do you do?"

"I design websites and write computer code for companies. Nothing exciting," Andy said shrugging his shoulders.

"What kind of companies?" Charlie asked, sounding genuinely interested, which she was.

"A few tech companies, some medical companies, and others."

"What's going on over here?" Natasha inquired.

"Enjoying these drinks and keeping clear of the dipshits," Angela said indicating Hunter and Kevin.

"Yeah, they're a bit much. What are ya drinking?"

"These great gin drinks Andy made for us," Charlie said. "Try it!" offering up hers to Natasha. She liked it immediately.

"That's really good! Can you make me one, too?" Natasha asked sweetly. Andy couldn't say no to those eyes/tits.

"Sure, excuse me," he said to everyone getting up to make the drink. Natasha took a seat in the same area as the other girls.

"Andy seems really nice," Natasha commented.

"I know, right?" Alex agreed. "He acts like someone in a house full of beautiful girls who was raised right. Not pawing at us and shit."