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."
