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.
