Island Adventures Ch. 01

Introductory chapter where Mike meets Cheryl and takes a job working on her charter sailboat.

Chapter 1

Meeting Cheryl

I'm 27 years old and have spent most of the last six years bumming around the Florida Keys, Bahamas, and Caribbean Islands. I graduated from college in three years with a business degree and absolutely no interest at all in trying to put it to use. I felt burned out and wanted to get away. What started as a two-week vacation to the U.S. Virgin Islands turned in to a complete lifestyle change and I never went back to the mainland.

I took odd jobs that mostly involved nothing more than physical labor and moved on when the job was over or I got bored and decided on a change of scenery. I learned a lot of different skills and met a lot of wonderful people along the way, and quickly discovered that I needed very little in the way of material possessions to live and enjoy life. I had just finished working with a small crew that floated around the Florida Keys and Bahamas digging in-ground swimming pools, mostly by hand, for some of the well-to-do residents, and took a job tending a small beach bar in Nassau while deciding what to do or where to go next.

The bar's owner and other bartender was a middle-aged American ex-patriot named Monica who took a liking to me and hired me on the spot. At 40, she looked older than she really was from spending most of her adult life outside. Her body was deeply tanned all over and covered with tattoos. She also had several piercings including a couple that were not visible to the public. Monica was very laid back and laughed a lot, but I also witnessed a very tough side of her when an occasional customer misread her friendliness for something more, or wouldn't take "no" for an answer. She was a keen businesswoman who didn't tolerate laziness or dishonesty in her staff. Employees that were more interested in hooking up with patrons or tried to skim some of the profits for themselves quickly found out the hard way how mean Monica could be.

I had been working for her for about six months and we would hook-up from time-to-time for some really great sex, but neither one of us was interested in more than that. She knew I was transient and would be leaving with little notice, but her staffing had always been like that and she accepted that fact. One morning when we were setting up the bar and kitchen before the lunch crowd straggled in, she asked me, "Have you ever done any sailing?"

I looked across the bar at her. "I used to sail when I was young and crewed a couple boats down here long enough to get from one island to another. Why?"

"A friend of mine has a charter sailboat down at the marina and she's looking for a new mate. Interested?"

I thought about it for a few seconds. The islands were coming out of the slow season and business at the bar would more than triple in just a few weeks. Monica was going to want someone experienced behind the bar when she wasn't there, and at the moment, that was me. "You looking to get rid of me?" I asked.

She grinned back. "Not if I have a choice. Even if I didn't need you working behind the bar here, I'm not anywhere close to getting tired of riding that dick of yours." Her smile dimmed. "But, I know you're already getting itchy to leave and I'd rather start breaking in someone new before the things get busy. Of course, if you want to stay the rest of the summer, I could probably make it a bit more interesting for you." Her implication was clear, just like the twin points of her long nipples poking out through the loose tank top she was wearing.

I don't think I ever saw Monica wearing a bra; tank tops and halters were her standard uniform over a pair of close-fitting shorts that emphasized her slightly broad hips and very round ass. Her 36DD breasts were beginning to droop from age and gravity, but were still quite firm and enjoyable. She probably increased her profits by dressing like that and having men stay around drinking longer hoping to get a peek at her breasts whenever she leaned forward.

I returned her original smile. "You are quite the temptress," I acknowledged. "What kind of charter work does your friend do?"

"Mostly day trips out around the islands, but she also makes trips between the islands just to have a change of pace and locale," Monica answered.

I mulled it over as I resumed wiping down the bar and restocking the various cups holding drink garnishes. "What's the name of the boat?"

"Pussy Galore," Monica said with a straight face.

I stopped what I was doing and looked back over at her. "You're shitting me."

"Nope, not even a little bit. If you're interested, she's berthed at Pier 3 at the marina. My friend's name is Cheryl. Don't get any ideas about messing with her, though. She's not easy, like me." I couldn't figure out if Monica was joking around with her last comment or not. Despite the relative ease that she and I hit it off and landed in bed together, I don't think anyone would ever call her "easy".

That afternoon when I was off for a couple hours, I wandered down to the marina to check out the Pussy Galore. It turned out to be easy to do-it was the only boat at Pier 3 when I got there. Pussy Galore was a 40 to 45-foot ketch that looked immaculate. As I neared the cockpit area of the boat, I saw a tall, thin woman cleaning and polishing the chrome railings and fixtures in that area.

"Are you Cheryl?" I called out. The woman straightened up and looked out at me.

"Who's asking?" she asked politely, but guardedly. Cheryl was a long-limbed and very slender woman who appeared to be about my age. She was well-tanned and wore a large flop hat over her short, sun-bleached hair. Her very long, lean, muscular legs were her most noticeable feature from a distance. Above her legs, she wore an over-size, long sleeve t-shirt that effectively obscured the upper part of her body underneath. Her shirt sported a logo for her charter business and underneath, she wore a bikini. I approached to stand on the dock right across from her.

"My name's Mike. I've been working for Monica and she suggested that I stop by and see if you were still looking for a mate."

At the mention of Monica's name, Cheryl's face relaxed and she gave me a small smile. "I am. Do you have any sailing experience on something like this?" she asked with a small wave of her hand in the general direction of the boat's bow.

"Like I told Monica, I learned to sail when I was young, and crewed on a couple of sailboats over the past three or four years. One was a charter and the other was a private boat owned by an older couple who wanted to spend more of their trip enjoying themselves than working the boat."

Cheryl invited me aboard and I think I noticed a small nod of approval when I took off my flip-flops before stepping over the gunwale. She took me around the boat in a tour that was more about checking out my own knowledge than showing off her boat. As I followed, I was struck by her very sure, efficient, and graceful movements and wondered if she had ever studied dance. When we returned to the cockpit, she sized me up one more time. "When can you be available?"

I almost said "Tomorrow", but paused. "I'm not sure. I need to talk to Monica first and let her know I'm leaving. I want to give her time to hire someone else so I don't leave her in a bind. Maybe a week from today at the latest?" Cheryl nodded thoughtfully.

"Sure you can't be here tomorrow? I have a two-day charter going around the island and need a mate to make it work," she pressed.

"I'd really like to, but I really don't want to leave Monica hanging out. She's always treated me well," I said wistfully.

"Okay," Cheryl said without much expression. One thing I decided about Cheryl is that she probably played a mean game of poker. Her face never gave away anything. I left her boat and headed back to the bar to grab a bite to eat before my evening shift started.

When I got there, Monica was waiting for me. "So, tonight's your last night," she said. I looked confused before recognizing that Cheryl had called Monica after I left and relayed at least her version of our conversation.

"I never said that. I told Cheryl I need to work out leaving with you first," I answered.

"I wasn't asking a question. I was making a statement," Monica said. "This is your last night here. Tomorrow, you're working on Cheryl's boat." Monica wasn't upset at all. In fact, she seemed happy.

"Don't you need to hire a new bartender?" I asked.

"Shit, I've run this bar by myself for almost as long as you've been alive," she said in blatant exaggeration. "Besides, I already have a new bar maid already picked out and she starts out tonight, so train her well!" Monica came out from behind the bar and gave me a big hug. "If you ever get tired of doing something else and want to come back and have some fun with an old lady, you're always welcome here," she said as we embraced.

After the bar closed that night, Monica took me back to her place and we fucked for two hours before falling asleep in each other's arms. That night was different from earlier sessions and seemed more serious, despite the teasing, laughing, and fun we still had with each other. I think for the first time, we both felt like it meant something when we joined and neither one wanted to lose that feeling. Our movements were unhurried and full of deeper feeling. We fell asleep on our sides facing each other with my cock still inside her pussy after enjoying a mutual climax.

That morning, we woke a couple hours after sunrise and took a lazy intimate shower together pretending like it wasn't different, but it was. For all her toughness, I saw Monica's eyes tearing up as we hugged for the last time before I left to pack my duffel and head to the marina.

When I arrived at the boat that morning, Cheryl was standing in the middle of the cockpit surrounded by items that she was checking and stowing away in various compartments. "I wondered if you were going to actually show up," she said without a trace of mirth when she saw me walking down the pier.

"Permission to come aboard?" I asked rhetorically as I kicked off my sandals and prepared to step over. Cheryl gave me a strange look over her shoulder.

"Were you in the Navy or did you just watch too many movies about boats?" she inquired. From her tone, I gathered that she didn't have much sense of humor. Cheryl straightened up, and once more I was surprised at how tall and lithe she was. I'm 6'2" and she didn't seem much shorter than me in her bare feet. I couldn't tell if she was wearing a different t-shirt from the previous day since it had the same charter sailboat logo as the one did yesterday, but she definitely had on the same bikini.

"You can put your gear down in the bow cabin for now. We need to inventory and check all this gear before putting it back where it belongs, double-check the rigging, wash down the topside areas, and then pick up some food for the two days we'll be out. The passengers are due here at noon, so that gives us three hours to get everything done," she said very business-like. She also sounded a little perturbed that I didn't report in earlier.

I dropped my duffel off where she told me and commenced helping her with the equipment inventory. I found a box of emergency flares that were out of date and a couple life preservers with straps that were badly dried out and frayed. Despite not being thrilled about having to replace some of the gear, Cheryl actually seemed happy that I actually knew what to look for. Once everything was stowed again, Cheryl left me to wash the topside surfaces while she went shopping for food and supplies. She returned after I had finished the freshwater washdown and found me inspecting the rigging on the mainsail for worn or frayed areas.

She put the food, stores, and new equipment away before joining me on the foredeck where I was finishing up. "Any problems?" she asked.

"Nothing serious. You'll need to replace the main halyard soon. It's got a couple of worn areas, but should be fine for a while. Everything else looks almost new," I replied as I secured the last line. She nodded and I noticed her eyes moving critically over the deck and cabin top as she silently evaluated my work.

"Looks good. Let's head below and take a break until our passengers show up," she suggested. I followed her down into the cabin and plopped down on the thickly cushioned bench seat across the small table from where she sat.

"We haven't talked about salary, yet," she began. Her eyes looked up at mine as she paused. I just nodded. She continued, "You get twenty percent of what we earn, paid when we finish the trip. I live on the boat and if you really need it, there's space for you to stay as well when we're in port, but don't get any ideas. I'm not looking for a relationship or casual fling, and my bed is off-limits to you and anyone else on this boat." She paused again to gauge my reaction.

"Works for me," I said simply.

Cheryl continued in a serious voice. "I'm the Captain of this boat and what I says goes. I'm not looking for arguments or discussion. If you aren't sure you can deal with that, save us both the headache and leave now. You won't hurt my feelings." From my limited interactions with Cheryl, I doubted much, if anything, could hurt her feelings.

"There are three ways to leave this boat. You can walk off, get carried off, or swim ashore. You do your job and follow my rules, you can walk off. If you try to get physical with me, you'll get carried off. And if you piss me off when we're at-sea, I'll move in close enough for you to have a 500-yard swim to the beach. Don't test me. I've had men bigger and badder than you try to pull shit on me and I'm the one left standing."

I kept my expression neutral but thought, "Holy shit! Monica wasn't kidding after all."

"One more thing. I offer clothing optional cruises and most of my clients take advantage of that freedom. If that's what they want, then we follow their lead. Is that a problem for you?" she asked quizzically.

Now I had visited a couple nude beaches as I bopped around the islands and even a few that people turned in to spontaneous nude beaches. At first, I have to admit, I felt a bit shy and self-conscious, and was afraid I might get aroused. However, I quickly discovered that most of the people at those beaches were much older than me, had skin that looked like tanned leather, and were generally not very attractive. I also discovered that they were all very friendly and none of them seemed interested in what my dick was doing or not doing.

"Not a problem for me," I assured her. Cheryl stared at me for a few more seconds and suddenly got up.

"Want a beer?" she asked as she reached down and opened the small refrigerator across from the table. She pulled out two bottles of the ubiquitous Red Stripe beer and we sat back sipping the cold brew and lost in our own thoughts.

"How did you come up with a name like Pussy Galore for your boat?" I finally asked after a minute or so of silence.

Cheryl actually smiled. "That was the name of the boat when I bought it," she replied. "The original owner was a big James Bond fan." I looked at her blankly.

"Pussy Galore. One of the characters in the James Bond novel, 'Goldfinger'" she explained patiently. I shook my head.

"Sorry, never read many spy novels," I answered after taking another swig of my beer while Cheryl stared at me in disbelief. "Did you ever watch any of the movies?" she asked incredulously.

"Just a couple about ten years ago or so. I'm not much of a spy movie person, either."

Cheryl just shook her head and took another big pull from her bottle. "You're the first person I've met who never heard of Pussy Galore." Just then, we heard two voices calling from outside and we hurried out to meet Cheryl's clients. It turned out, they were four men in their mid-thirties to mid-forties carrying large backpacks and a large duffel with fins, masks, and snorkels for diving.

"Come aboard!" Cheryl called out cheerfully. "Please take off your shoes first, though. We stay barefoot on the boot to keep from leaving scuff marks on the deck."

I stepped off to help bring their gear aboard and stowed it below in the cabin while Cheryl welcomed them aboard. She called down for me to bring up four more beers and I joined everyone as they sat around the back of the cockpit. Cheryl went over the basic safety rules and showed her clients where life preservers were kept.

"I assume you all swim," she stated smoothly and all four men nodded in response. "I plan on stopping in a couple of coves I know about where the diving is nice and we'll probably stay overnight at one. Unfortunately, there's not much to see there if you want to do any night diving." The men just grinned at her and I saw two of them holding hands. "Oh!" I thought.

Cheryl showed them to interior of the cabin and the four bunks where they would be sleeping. I think a couple of the guys were let down that the bunks weren't large enough for two to sleep comfortably, but otherwise, they were quite happy with the arrangements. "When are we leaving?" the oldest one asked.

"If you're ready, we can leave right now," Cheryl said briskly. All four men broke out into smiles. "Let's go, then!" they replied eagerly.

Cheryl told the dock master that we were heading out and would be back the following evening as I readied the lies to cast off. As soon as she climbed back aboard, I set the jib sail and cast off with a strong push that had us gliding slowly into the harbor. The wind caught the jib and Cheryl smoothly handled the helm to point the boat out towards the breakwater. I hurried back to raise and set the mizzen stay sail and we started picking up more speed to move out gracefully. Then, Cheryl had me wait up on the foredeck to raise the mainsail as soon as we cleared the harbor.

Two of the men remained in the cockpit and tried to stay out of the way, while the other two climbed up on the foredeck to join me. One of them knew a little about sailing and was very complimentary about Cheryl's boat. "So, are you two...?" he asked out of the blue.

I looked at him with a slight smile. "No, I just work for her." He nodded, but I don't think he completely believed me.

When we were about four miles offshore, the man who had been talking with me asked if he could get undressed. I shrugged my shoulders. "Whatever you want to do," I replied. Looking at the island in the distance and all the boats in view of us, he looked a little uncertain, but both men headed back to the cabin. I rejoined Cheryl in the cockpit where she skillfully handled the helm.

"You did well getting us out of the harbor," she told me pleasantly. "Maybe you'll work out after all." I had to look at her carefully to see how serious she was being. When she glanced briefly my way, I saw a small smile on her lips and I relaxed. Perhaps Cheryl did have a lighter side, after all.

All four men came trooping up from the cabin, sans clothing but carrying large beach towels. They slowed to look around. Seeing no other boats in the immediate area, they headed up to the foredeck and sat or laid down on their towels in the bright sun. Cheryl looked at me. "You're now in Rome...," she commented with a hint of amusement. I looked back at her and shucked off my shirt before dropping my shorts. It was hard to see her eyes behind the sunglasses she was wearing, but I felt them traveling over my body as she appraised me.

Digging pools by hand for four months built up my shoulders and arms and I still carried that muscle even after tending Monica's bar for six months. Similarly, my dark tan never faded and the pale area from my waist to my upper thighs stood out in sharp contrast to the rest of my body.

After I stripped, Cheryl smoothly raised her t-shirt and I caught my first glimpse of her upper body. Just like her arms and legs, her torso was lean and showed no signs of softness. Her stomach was flat and taut so that her navel was barely a depression in its surface. Her breasts were smallish, perhaps a 34B cup, but didn't seem out of place with the rest of her trim frame. After tossing her shirt on the bench behind her, Cheryl untied the top of her string bikini and tossed it on top of her shirt.