Working in Paradise Chapter 2

Warning:  The usual disclaimers apply here.  If you don’t like any of the following, leave now:  gay sex, vulgar or harsh language or underage wherever you are reading this.
This is pure one hundred percent fiction. No one in this story is a real person, living or deceased. Please do not copy without my consent.
Please practice safe sex as this is just fictional.

It was early Saturday morning when I woke to begin my job here on the island.  I left Jason in bed while showering before heading to the main house to prepare breakfast for Gary and Lewis.  I dress quietly and made the trek to the house. 

Being a weekend, the menu was my choosing for the day.  I scrambled eggs, fried some ham and toasted bread for their meal.  The juice and coffee were standard.  I served them right at 8 as expected.

“Caleb, you’re a young man.  What are your thoughts about our opening up the island to these college guys?” Lewis asked.

“Sir, I’m fine with the decision.  It will make for an interesting few weeks to say the least,” I replied. “For the most part, sir, it should be fun and give us a break from the norm.”

“You don’t think they will wreck havoc here do you?” Gary asked.

“They might be. They are still guys,” I replied.

“They are gay.  Young gay men are calm and controlled,” Lewis said.

“Sir, they are still guys.  If they are like my gay friends in college, it might get wild but still not be totally out of control,” I said.

“I see.  Lewis, we will have to keep a watchful eye on them.  This was your idea in the first place,” Gary said.

“I will take the blame but also the credit no matter what happens, Gary.  Like Caleb said it might be fun having more young blood here instead of the older crowd we generally cater to here,” Lewis said.  “I’ll have some more juice, please.”

I did as requested and quickly returned with juice and coffee for Gary.  Lewis had no qualms at us being his servants while Gary wasn’t so demanding and tried to be civil to us.  After they finished, I cleaned up and planned the day after a brief consultation with them on their desires.  Thankfully both wanted something light which made it easy on me in my planning and preparation.   I started a short list needed on the weekly run to Nassau that Monday.

As I was about to begin prepping for a light lunch, Roscoe came to the kitchen in his short shorts and a tank top.  He was a short guy probably 5’6” or so but was muscular in frame. 

“We are all at the quarters doing a little planning for our spring break guests.  It is our job to plan the menu.  Here’s a rough outline what I was thinking,” Roscoe handed me a computer printed sheet with each day’s menu.  I took some time and scanned it to see his ideas.

“Roscoe, this sounds great if it were a bunch of 30 or 40 year old guys.  You forgot we are catering to college guys,” I said only to see him give a weird look of disbelief.  “See here.  No college kid wants fried chicken on their visit to the Caribbean.  How about jerk chicken with a little island flavor?”  I pointed out a few other things such as his elaborate breakfast and desserts.  “For one, most will sleep in if it goes as I expect.  Think of food you would want with beer.  This elaborate wine list is unnecessary, don’t you think?”

Roscoe snatched the list from my hand and then smiled, “I’m glad you’re here Caleb.  What the hell was I thinking?  Let me go change to your basic beer drinking food and college fare items. It might be fun for change.”

“Roscoe keep like the steak the first night and lobster on the last night.  I know they probably don’t get those at college.  We can just see how the first week goes and adjust things on the fly.”

“Great idea.  I just figured it would be the same all 3 weeks but you’re so right.  We’ll have to be flexible and go from there,” Roscoe said and left after inspecting my menu.

The day was rather easy on me.  Normally, I dreaded a Saturday evening meal but Gary and Lewis just wanted to keep it light and healthy for a change.  I did have to consult Roscoe again for I was unsure the correct wine for the evening meal.  I was learning the wine culture but still had a lot to learn.

When I returned to the quarters that night, it was just Bill and Simian the older ones there for the rest were gone on the boat for a while. 

“I’ve worked all day on the activity schedule for the coming weeks,” Bill stated.  “I need a good opinion, Caleb.”

Again I was asked to give my humble opinion of what a 40 year old found entertaining and fun for gay college guys.  I scanned the fully detailed list that had something planned for each day they were there.
“Bill, it looks and sounds fun, but…”

“You don’t like, do you?” he interrupted.

“It’s okay but you have to consider these guys are vacation not some summer camp like school kids.  I think a few of these are fine but don’t have something every day, plus you’ll wear us out too.  Now the best ass might be fun one night but we’ll have to see what kind of crowd we’re dealing with.  Beach volleyball contest is good for maybe the last day.  I really think they will be here to kick back, get a tan, get wasted and have sex,” I said.

“See I told you this was over the top,” Simian said.

“Do like me and Roscoe are doing.  Just see what goes over the first week and go from there,” I said.  I turned and saw the others coming in the door right as the sun began to set. Jason came and sat right next to me and gave me a nice smile. They passed around the list of activities and agreed with me that Bill’s list was nice but way too much.

“Dude, all these boys are coming for is to fuck and drink,” Javier said in his usual blunt tone.  “I know I wouldn’t want to do all this shit on my vacation.”

“Javier, sex is all you think about but you’re right.  These boys probably paid a shit load to come.  They don’t want to be so structured every minute and feel like they have to do this to have fun.  Have some drinking games and shit like that,” Jeff said.  He was usually not outspoken but gave an honest assessment.  “I can take them out say Tuesday for a short fishing trip.  Not everyone will want to do it but it might be nice.  Then one day, say Jason can take them hiking in the woods to explore the other part of the island.”

“Guys, let me trash this and start all over.  To think I wasted a whole damn day racking my brain to come with some fun ideas,” Bill said, shaking his balding head.

“Bill, it’s a good starting point,” Simian said while patting Bill on the back for support.

We tossed ideas back and forth for a good while that night.  It was actually fun and gave us a break from our normal routine of servicing the owners and their uppity guests.  We all knew and agreed it would take a complete team effort to make this a successful week but one that could have some nice eye-candy along the way.

After we finished, the drinking began.  I was up for a good night of drinking since I didn’t have to work the next day.  We grabbed a few bottles and headed to the beach along with a cooler filled with beer. We were, more or less, family here stuck on this island in the Atlantic Ocean.  We had our ways of entertaining ourselves but it usually revolved around getting drunk and partying then having hot sex. 

The night was relatively calm until Javier and Pedro decided to change things.  Both were small thin Hispanic guys who were generally fun loving guys.  Both had too much alcohol and fueled a basic throw down.  This happened occasionally since we were around each other 24/7.  We all watched for a minute as they cursed each other in Spanish loudly.  Pedro had enough and went after Javier.  We let them get out of their system until we finally pulled them apart.  Javier had blood dripping from his forehead while Pedro had a fat lip.  I don’t know what fueled the fight but just assumed it was something stupid like always plus small things can cause the biggest fights.

After the commotion ended, we all headed inside but kept the two apart.  Jason grabbed my hand and let me to what was now our room.  I fell on top of him in our small double bed. 

Jason looked me in the eyes, “Let me take you tonight.”

I smiled at him even though I did enjoying bottoming for him and his thick meat.  We exchanged wet sloppy blow jobs for a little time before I had the pleasure of eating out his tasty hole.  My tongue darted in, out and around this wanting hole.  Jason was worked to a frenzy and begging to get fucked.

The second my 7 inch cut cock sank in him, it was pure joy and delight.  His ass sucked up my cock while he was on knees.  I gave it him like he wanted it, hard.  His moaning and grunting filled our small space.  I could hear we weren’t alone enjoying hot gay sex that night as well through the rather thin walls of our quarters.  Sweat poured off my forehead during this hot encounter. 

Jason flipped over and spread his muscular legs wide.  He pulled me close and deep.  I just stared into his bright blue eyes while fondling his small nipples.  He grabbed the back of my long growing dark hair for a short kiss.
“Caleb, you feel so good in me tonight,” Jason said while his eyes rolled back in great pleasure.

The sound of my skin slapping against his mixed with his deep lustful moans filled our space.  Ramming him hard send me over the top and sent shot after shot deep in his body.  I caught my breath still buried in him and fucked him a little more while he vigorously jacked his thick meat.  I slowly exited his dripping ass and tasted my good work.  After licking him clean, my mouth wanted more and headed straight to his hard throbbing cock.  My mouth began to tire working his fine cock until Jason shot down my throat.  In culinary school, I had the reputation as a certified cum whore and continued the reputation on the cruise line as well, tasting many foreign flavors of man juice. 

Jason pulled me up, “To think I actually had thoughts of leaving here.”

I stroked his face with my index finger while my other hand petted his flaccid meat, “I hope you do stay around a little longer.”

“I’ll tell Lewis Monday that I’m staying for another go-around,” Jason said. 

The next day Sunday was finally my day to sleep in and take it easy.  Both Jason and I stayed in bed to at least nine.  Our door busted open.  “Jason, the water treatment system is clogged.  I really need your help,” Jeff said.

“Okay, give me a few minutes and I’ll be right up,” Jason said, rubbing his eyes and stretching. 

With nothing better to do, I decided to join Jason and Jeff.  I wasn’t very mechanical but I could watch and maybe learn something.  We both threw on shorts and headed to find Jeff.  Jason opened the door to a large room filled with a variety of equipment.  Jason jumped right in and gave Jeff a hand.  Sand and other debris in the filtering system were the problem.  I just stood and watched while they tried to find the clog.  It took some time and many test before the exact location was discovered.  I helped then by handing out the necessary tools as requested.  If nothing else, I did get to see first hand how the inner workings of this island were done.  After the problem was fixed, Jason and Jeff tried to explain the electrical and sewage treatment, but it was a little over my head.

We headed back to the quarters to relax and enjoy our day.  We ate and then headed down to the beach where just Bill and Pedro were swimming in the cool waters.  “Caleb, you wanna grab the sail boat and head out?” Jason asked.

“Sure, it sounds like fun.  I take you know how to operate it,” I remarked.

“Of course, I do,” Jason said.  One thing Gary and Lewis did have were plenty of water toys for us to take advantage of.  Jason pulled out the small sail boat.  I shed my shorts and knew sailing naked would be a blast.  Jason got us offshore and manned the controls. 

“This is the fucking life, huh?” Jason smiled, naked as I was.

“So you are staying,” I asked just to make sure he hadn’t changed his mind.

“Yes, I am,” Jason said.  “Why leave when I have a cute boyfriend?”  Even though that now was obvious to the others, we kept it quiet.  It was fine for Bill and Simian to be lovers but with the turnover, the others weren’t expected to get that close. 

Sailing just a few hundred yards off shore in the bright late February sun was the best.  Jason and I just laid back and enjoyed the vast open water.  The water was so blue and fairly clear that day with a calm ocean. 

“Caleb, it would be beyond hot if we were to have sex out here,” Jason smiled.

I just smiled and went down on him right there in the open water.  After sucking his tasty meat, I slid my ass on top of his throbbing cock.  The combination of the waves and Jason made for one hell of a great ride.  I was screaming to the top of my lungs in pleasure and just the sheer excitement of the moment. 

Jason then laid me on my side and continued to use his hard thick cock for my ultimate pleasure.  We let the wind control the boat while we had hot sex.  It was the best sexual experience I had had so far in my gay life.  Jason came quicker than normal and shot his creamy load up my back.  I shot mine all over my abs and chest.  The rest of the sail we just sat close and enjoyed being with each other.  We circled the small 35 acre island and finally were ashore after a good 3 hours. 

“Welcome to the open sea club, Caleb.  I know Jason fucked that hot little ass out there,” Javier said while we pulled the boat ashore.

“I’m a full fledged member now Javier,” I smiled and noticed how much sun I had received during our sail. 

“Javier, I would have made you proud,” Jason smiled.

“OOO Caleb man, your ass is red as a lobster,” Pedro said.

“Oh well, it was worth it,” I said.  “I’m trying to get as dark as you and Javier.” 

“Caleb, you have too much white blood for that shit, man,” Javier laughed.  “You can keep trying though.”

The upcoming week was pure hell for all of us.  Gary and Lewis were on pins and needles now with Lewis being a complete ass to all of us.  The worst part was the resentment that was mounting towards him among all of us including Simian.  He normally was very even keel but was as moody as ever from the mounting pressure.

Friday after a rough week, I headed back to the quarters.  I found Jason walking outside. 

“Caleb, I’ve changed my mind,” Jason said quietly.


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