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Setting Sail Southbound
Back when I was in my early 20’s, I was fresh for adventure & I wanted to see what the world had to offer, so when an opportunity to travel somewhere nice became available, I was usually pretty proactive in getting myself involved. Luck came my way one Wednesday afternoon in bar called the Lee Side in Woods Hole MA. I somehow ended up chatting with a couple who wanted to take their 70’ sailboat down to Florida for the winter, but they needed an extra hand or two to make the trip more comfortable. There would be no pay involved, but food & travel expenses would be covered. 3 or 4 drinks later, we had an agreement & a planned departure date. Apparently, they had one other person they planned to pick up on the way, in Point Judith.
The departure day came & I showed up at the docks as planned. They looked well ready for the voyage. The boat was polished. Supplies were stowed. He looked like something out of a J Crew catalog & she was wearing a thin flowing dress that you could easily see though when the sun was behind her. A cooler full of drinks was in the cockpit.
I quickly stowed my bag in the cabin they assigned to me & found my way back up on deck for my assignments. After a quick briefing on safety gear, basic duties & shift schedules, They had me cast off the lines & we headed out of the harbor. It was a nice day. It was picture perfect.
Once we were out in the open ocean, Sherri popped open a beer & handed it to Rob, then popped another and handed it to me. She then poured a glass of wine for herself. She explained that while underway, the helmsman normally limited himself to one drink per 4 hour shift, but the rest of us could dip a little deeper into the cooler if we pleased. She commented that they liked to have fun when they traveled & they often carried more booze than fuel. She then kissed me on the cheek, & said that she was glad to have me along on the trip. I gave Rob a slightly uncomfortable look. He smiled & commented that after another glass of wine, the next kiss would probably be on the lips, so if I became uncomfortable that easily, I would probably need to be sure that I got another drink before she did. He didn’t seem to be kidding.
After a few minutes of small talk, Sherri decided it was time to loose the dress & get some sun. She stripped it off in a single motion, that could only have become so flawless from plenty of practice. I got the impression that she liked to spend a lot of time with her clothes off. She asked me to run down below to get a towel to lay out on the forward deck for her. I complied quickly. As she laid down, she asked me to keep her company. After a few more minutes of small talk, she was asking me to fetch her another glass of wine. I was right on it. 2 or 3 sips into that glass, she made a comment about me being overdressed & started to loosen my belt. I gave Rob a quick glance, but he just smiled & nodded. Apparently this was not out of place for them.
Once my shorts came off, she giggled & commented about my tan lines, as she had none. She ran her fingers along the edge of the tan line on my right leg, then when she got to where my two legs came together, she moved her hand up & grabbed my already growing member. She popped it into her mouth for just a second or two & commented that was just a taste of things to come. She then flipped over on her stomach & closed her eyes.
I didn’t know what to do, but Rob was still smiling so I figured that my options were probably pretty open. I climbed on top & straddled her to give her a bit of a back rub, with my member laying on the crack of her ass. She smiled & purred. She wiggled her butt a little now & then. I slid a little deeper into her crack when she did that. Eventually, she reached around with her right hand & grabbed my dick again. She gave it a gentle stroke, which was all it took at this point for it to become rock hard. She then wiggled a little more & worked my dick down between her legs, where I easily slipped inside her. She was not particularly tight & she was very well lubricated, so it was a sloppy fuck. I gently worked in & out of her deep & slow, which made her moan & wiggle some more. It wasn’t long before my hands had left her shoulders & moved down to her ass. I had a form grip on her two butt cheeks as I moved in & out of her. She seemed quite happy, as she matched my motion & rhythm. She also had the apparent ability to control her contractions at will. She tightened up when I pushed in & went almost limp when I eased out. It felt like I was going deeper & deeper with each thrust. She played me like a fiddle until I couldn’t hold out any longer. I pulled out just in time to let my load go on her left cheek, rather than inside her. She reached down, took a sample with her finger & tasted it. She said “thick & salty, you haven’t been getting it very much lately, have you?” I blushed. a bit. She said “don’t worry, I’ll have you thinned out by the time we get to Rohde Island, but do be a dear & get me a cloth so that I can clean up a bit.”. When I brought her the cloth, she let me know that next time, I could let it go inside her. She liked to feel gushy.
Somehow, time had flown by & it was my turn on the wheel already. I took over steering & Rob went to pick up where I had left off, keeping a smile on Sherri’s face. This little round robin rotation went on for the next day & a half. I didn’t get a whole lot of sleep between steering 4 hours then playing with Sherri for much of the 8 hours that I had before my next shift. When we pulled into Point Judith, it was close to midnight. We put the boat at anchor & the three of us passed out.
In the morning, the sound of a small outboard & the smell of coffee & cinnamon buns woke me up. I looked out the port hole to see Sherri with a new hairdo being dropped off back on the boat from a small tender boat. It seemed strange that she would have gotten a haircut so early in the morning, but I didn’t know the area, so I didn’t know what was available. When I went up on deck, Sherry was back to her old haircut. What? Was she wearing a wig? Then I saw that there were two identical women there. Sherry introduced me to her twin, Helen. I did a double take.
Helen was a bit forward. She commented that Sherry had informed her that they had brought a boy toy along for the women’s pleasure & it was a good thing because Rob couldn’t keep up with both of them.
Aside from the haricuts, the two sisters were exactly alike, right down to their lack of tan lines & outstanding muscle control. They were both heavenly to play with.
Now with 4 on board, the boat, the schedule was the first thing to learn. I would have 4 hours on & 12 hours off, so there was plenty of time for frolicking & a full 8 hours of sleep. The next 9 days flew by in a haze of whisky, women and waves.
I can’t even count how many times I came. Life was good & I was living it. I arrived in Florida with an allover tan, a big smile on my face & some VERY fond memories.
That was the most outstanding boat trip I have ever taken. Later in life, I would settle back into that area & continue playinginpalmbeach with an SLS handle of the same name.