The Mystic Adventure

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He finds sexual adventure on a sailing trip to the isles.
18k words
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Part 1 of the 5 part series

Updated 10/11/2022
Created 12/08/2009
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The alarm clock went off at 4:30 am sharp, dragging me back to consciousness from a sleep that I thought, last night, would never come. Things are usually better in the morning right? Let's see. Nope, this still sucks. I set the alarm last night because, well, what else am I going to do? I reserved the boat, bought the plane tickets, stopped the mail, all that stuff. Maybe a week in a tropical paradise will help me to forget her but, at this point, it's not looking good.

I got up, showered, dressed, and had a light breakfast - all in haze. I loaded the car and headed to the airport, analyzing the situation as best I could. OK, honestly, I knew this was coming. We had been drifting apart for a while now. She was hell bent on the race up the corporate ladder and I was trying to get away from all that. I was trying to simplify and she was trying to do everything, and have everything. At first, it was exciting to see her put so much of herself into it and to see her succeed. But little by little, she began to be consumed by it. Everything else took second place to "The Plan", as she called it.

The Plan called for her to make her way to the top of the firm in three years and then take over the division in New York City. We'd "get" to move to the city and get out of this "boring" little bedroom community on the lake. "Gee honey, that sounds great." I booked this trip to see if I could show her the beauty of simplicity and the magic of clean ocean air. I figured that once she was on that boat, disconnected from her Blackberry, unable to check email, she would relax and loosen up a little. I was also hoping she would unwind a little too. Get a little crazy. The sex we had was good but it just wasn't - oh hell, the sex really wasn't that good. It should have been. She was stunningly attractive. She turned me on visually but in bed, she had no, I don't know, adventure. No recklessness. I'm not looking for a slut (well not too much) but I want someone who is into it. Not someone who is thinking about what they are going to do when it's over.

Holy shit! I just about missed the exit for the airport! I must have been on autopilot the whole way, reflecting on the relationship and how we had gotten to where we were. Having re-analyzed the entire picture, I suddenly realized that I'm actually lucky to be rid of her. When she called last night to say she wasn't coming and that she wanted to be apart for a while, I was crushed, angry, and hurt. But now, it was like a giant weight had been lifted off my shoulders. I suddenly felt better than I had in probably over a year. I was heading to St. Thomas for a fabulous week of sailing in the Virgin Islands. I'd be alone but hey, it's better than Winter in Hartford right?

I headed to the long-term parking lot to begin the arduous process of boarding my flight to St. Thomas. As I shuffled through the security lines trying to hang on to my license, boarding pass, shoes, and carry-on, I was trying to figure out how I would convince the charter company to let me take the boat by myself. Chartering a bareboat in the Caribbean is ridiculously easy. From my past observation of other charterers, they will let practically anyone take a boat out. Of course, I had plenty of experience from years of sailing everything from tiny racing boats to large, ocean-going yachts so I was confident of my abilities. I just wasn't so sure they would see things the same way. A 43 foot boat is big and, while you can do it, they really aren't designed to be sailed by one person. Hmm, this could take some fast talking...

They finally called the flight and I made my way down the jetway and found seat 18A, a window seat that would provide a great view of the islands when we landed. Of course seat 18B was unoccupied but I don't care about that, remember? Seat 18C was empty so I had the whole row to myself. Please, oh please, don't let some motormouth take that seat. Or some large woman with way too much perfume. Or, please God, not a mom with a baby. I love kids but not on a 5 hour flight.

Person by person, they passed by the empty seat and I started to hope against hope that I'd escape the agony. Oh God, here comes a woman in a muumuu. Please, please, please... She passed by, loudly wondering where row 28 was. Then, I catch a glimpse of blond hair up ahead. An instant later, a flash of blue eyes. Then, I see a face that causes my breath to catch in my throat. All of a sudden, I'm hoping, praying, begging whomever might be up there calling the shots (not that I've ever thought there was) to let her have a boarding pass that says seat 18C. As she gets close, I try not to stare. I casually look around like I'm just taking in the crowd in general, but all the time, I'm stealing tiny glances at her, taking in the details, absorbing her features, learning her from a hundred photos in my mind's eye.

There are two kinds of beautiful women. The first kind is the model type - stunningly beautiful, perfect hair, perfect skin, what most people would classify as "hot". These women know they are beautiful and they know that every guy is looking at them and wondering if they have a chance. The other kind is the "girl next door" variety. Pretty, but in an "I would actually talk to you" kind of way. This girl, approaching seat 18C with the force of every known or imaginary deity being brought to bear to will her into that seat, was the second kind. Actually, she seemed to be some kind of impossible mix between the two. She had blond hair and crystal blue eyes that seemed unnaturally bright. Her face seemed - "fresh" is the only way I can describe it. She gave off the kind of vibe that seemed to say she was just happy to be alive and off on adventure. And, perhaps more importantly, she seemed to be traveling alone.

As she got to my row, I saw her scan the number above my head, double check here boarding pass and give that little "I found it" look. Yesss! Then, as time slowed to a crawl from her looking at her pass and then shifting her eyes to me, I found myself wondering - is she really the girl next door type who will actually be as nice as she looks or will she turn out to be a stuck up snob. Should I try to start a conversation with her? What would I say? Does she have a boyfriend who's just behind her? Will she suck my dick in the lavatory at 30,000 feet? OK, that last one shouldn't have gotten in there just yet. All right, dream time is over, look at her. I slowly looked directly at her and as our eyes met, she smiled the most sincere, and therefore dazzling and wonderful smile I'd ever seen and said "Hi, I'm Kelly and I think I'm in 18C".

Yesss!

"Yup, this is row 18. Hey, I'm Brad."

It sounds cliche, but when our eyes met, there was a "spark", or whatever you call it when the connection lasts a fraction of a second longer than it would normally in a casual encounter. I don't know, maybe I imagined the whole "moment" but it sure boosted my mood and, I have to say, boosted the firmness of my cock ever so slightly. This stirring in my groin wasn't slowed when I got a look at her body either. She was wearing a light blue tank top and a pair of khaki shorts that were rolled up to become short-shorts. It was a perfect combination of casualness mixed with a hint of sexiness that is so hard to pull off. It's the kind where you can enjoy the beautiful view but not be embarrassed for her that she's out in public like that.

She set her purse on the seat and looked up at the overhead bin to find a place to stash her carry-on. As she reached up to put the bag up top, her tank top raised up to expose a perfectly flat, trim stomach. What's more, her shorts gapped away from her just enough to accentuate the view. I quickly looked away so as not to be the creepy seatmate that she was probably dreading sitting next to just as much as I was hoping not to get the muumuu lady. It was all I could do though. My heart was practically beating out of my chest. Did she do that on purpose? Did she spend a second or two extra adjusting her bag in the overhead? I had to will myself to calm down and not let my imagination run away with me. In all likelihood, she was just moving things around up there. She was probably going to visit a boyfriend or something and I was getting all fired up for nothing.

Whatever, there was one more physical attribute I had to get a look at though so I timed my look back from the window just as she was turning sideways to sit down so I could checkout her ass. Yup, perfect as I suspected. Perfectly round, firm looking, and no visible panty lines. I like thongs...

She popped down on the seat like you do when you have been on your feet dealing with getting through the airport and are finally able to sit down.

"Hi Brad, nice to meet you. How's life treating you today?"

I wasn't expecting that last question. It wasn't the typical "How are you" that nobody really wants to know the answer to. It was like she was actually asking me how my life was going on this particular day and was interested in the answer.

"Um, hey, nice to me you too Kelly. Well, to be honest, I'm on a bit of a rollercoaster today. It's been down, and then up and well, I'm not really sure where it's going."

"Well, I hope it's going up. Are you kidding, we are on a flight to St. Thomas in the Virgin Islands. The weather will be fantastic, we won't be working - you're going down there for play, not work right? What could be more perfect? I'd say life is treating us pretty good right now."

"That's a good point. I like your perspective on things." Yeah, that's the way I've always looked at things - the bright side. I have to get back to that.

"So Brad, are you on the cruise from St. Thomas? I'm meeting a friend down there. We've been planning to get away for this cruise for ages and we finally did it. I can't wait.

Crap! She's meeting her boyfriend after all. Oh well, that was certainly the likely scenario so I can't say I was surprised. Just a little disappointed. At least she'll be fun to look at and talk to for the 5 hour flight. It could have been muumuu woman.

"Yeah, my girlfriend Kim and I decided we needed to get out of the city and the hustle and bustle and just go for a little alone time. From what I've heard, this cruise is the way to do it. It's kind of a party boat and less of a senior citizen center than other ships."

"Oh, your girlfriend. That sounds great. I'm sure you two will love it. It's good to get away from the 'real world' and reconnect with each other." Hmm, so it's not a boyfriend but a girlfriend. How is it that my cock can go from totally let down to contemplating a kinky fantasy faster than my brain can? Hold it there buster, she's still getting on a ship when she gets there and you'll never see her again. Nothing has changed. Just enjoy the ride and try not to load yourself up.

I don't think I conveyed any of those thoughts in my head with my response but she paused for a second like I'd said something that confused her.

"Oh, I don't mean my girlfriend-girlfriend" she laughed as she air-quoted "girlfriend-girlfriend". "Nah, she's just my best friend since grade school. Of course, if I was going to have a 'girlfriend-girlfriend', she would be the one. She's so funny and has the most beautiful... Oops! That's probably too much information. Sorry! So, are you going to be on the cruise?"

"No, I'm actually renting a sailboat and I'm going to sail around the islands for 10 days. It's called a bareboat charter."

She did a sort of double take. "Really? I've never heard of that. So how many people are on the boat? Do they have a crew that helps you sail it?"

"No, it's just me. Bareboat means that you sail it yourself - no captain or anything. I've been sailing all my life and I've done this before so it's not a big deal. I had a crew member but she backed out at the last minute. Now I have to convince them to let me still take the boat by myself. Otherwise, I'm going down there for nothing."

"Oh man, that's sounds really cool! But wait, your crew - was it your girlfriend? - just decided not to come? What's up with that?"

"I guess she decided that now was the right time to tell me that she didn't want to spend time in a sailboat, away from her email and the amenities of city life. I'm not actually surprised but the timing sure sucks. That's why I said it had been a rollercoaster of a day. I was feeling sorry for myself earlier but when you said hello and just seemed so happy - looking forward to whatever came your way, it put me in a much better mood. So thanks for that."

She reached over and put her hand on my arm. I swear I felt a tiny jolt of electricity race from my arm directly to my dick. "Hey, I'm sorry she did that to you. I can't imagine turning down an adventure like that in favor of more time on my Blackberry but I guess some people just don't think the way we do, do they?"

"Thanks, I guess not."

We continued talking as the rest of the passengers came aboard and got settled in. I asked about the cruise itinerary and the islands she would visit and gave her some recommendations for things to see on each one. She wanted to know more about the bareboat charter and how that worked - how do I know where to go, where do I sleep, all that stuff. I found myself just gazing into her eyes as she talked. I was hearing what she was saying but I was also just drinking her in. She was so comfortable and easy to talk to. She just seemed to enjoy life and look forward to anything that might come her way. Of course, that attitude, coupled with the way she looked and smelled - I think I caught a whiff of some sort of light perfume or soap that was again, in keeping with her "fresh" vibe - was slowly intoxicating me.

After a while, I came back to reality and realized that we had been sitting there for a long time. The passengers were all seated and nothing was happening. Just then, the Captain came over the loudspeaker.

"Ladies and Gentlemen, this the Captain. I'm afraid there is going to be a slight delay. There have been severe thunderstorms across the country today and many flights have been redirected to this airport. In order to let those planes land, we will not be able to take off for about an hour or so. Since this is a direct flight to St. Thomas, hopefully, you don't have connecting flights that you would be in danger of missing. We'll try to get you to St. Thomas as quickly as we can."

There were a few groans from the other passengers but when I looked over at Kelly to give her an "Oh well" smile, she looked very concerned.

"Looks like we might get to St. Thomas a little later than planned huh? You're catching the ship tomorrow right?"

She turned to me with a pained expression. "No, it's leaving today! We didn't want to spend the extra money on a hotel room so we timed our flights to get there by 1:00. The ship leaves at 5:00 so we figured we would have plenty of time."

"No problem. The airport is not far from the cruise docks. Even if you are a few hours late, you'll be able to make it. Don't worry".

She visibly relaxed a bit. "Yeah, you're right. It's only going to be an hour. I'll text Kim and tell her I'm going to be a little late."

Our conversation continued, like we were old friends catching up on each other's lives after a long time apart. About 45 minutes later, the Captain came on the speaker again.

"Ladies and Gentlemen, I'm afraid there's going to be another delay. The weather pattern that affected all the other flights is now affecting our departure. It's hard to tell but it looks like it's going to be at least another hour before we can leave. Our estimated arrival time in St. Thomas is now 3:15 pm. We do apologize for the inconvenience and we'll do everything we can to get you to St. Thomas as quickly as we can."

More groans from the other passengers, a bit louder this time. I looked over at Kelly and saw the worry creep back into her expression.

"Don't worry Kelly. You'll make it. Besides, if worse comes to worse, and you don't make it there in time, you can catch a flight to, where is the first stop, Cayman?, and get on the ship there. People do it all the time."

"Really? Oh that's a relief." Again, her face shifted back to her "everything's an adventure" expression and her concern was over. I looked down at the empty seat between us and thought of the person who would have been there and how she would have reacted. She would have been demanding to speak with the pilot or the president of the airlines, wanting to know what they were going to do to get her to her destination. Didn't they know that she had a printed itinerary for god's sake? Ugh.

I looked up to see Kelly looking at me. "Will you have a problem getting your boat if we get there late?"

This time it was my turn for a little double take. Here she is, faced with potentially missing her ship but not so self-centered that she can't still be concerned with how the delay might affect me. It was so refreshing to see someone who doesn't assume the world revolves around them - you know who you are 18B. "No, I'm picking up the boat tomorrow. I booked a hotel room for tonight. These kinds of delays happen enough that I wanted to be on the safe side. Besides, it's fun to hit the nightlife in Charlotte Amolie... Hmm, might not be so fun alone."

"Aww, I'd hit the bars with you. We'd have a great time wouldn't we?"

"Yeah, I think we would." Oh man, this girl is killing me. Does she even know what effect she is having on me? My mind drifts to thoughts of her in a crowed bar with me being pressed up close to her. The dance floor is so packed that people are jammed together barely able to move except for the rhythmic pumping in time with the beat. I'm trying desperately to think of muumuu woman to keep my cock from jabbing her in the stomach as she grinds into me. It's not working though is it? I picture her looking up at me with a sly grin as she grinds a little harder.

I'm snapped back to reality by the Captain's voice again. "Ladies and Gentlemen, we've been cleared to depart for St. Thomas." The passengers clap and cheer but quickly quiet as the Captain keeps speaking. "But we are going to have to re-route around the weather which will result in a further delay in reaching our destination. We should arrive in St. Thomas at around 4:30 pm."

More groans from the passengers.

"I guess I'll be trying to get a flight to Cayman," Kelly says but she doesn't look that happy about it.

"It'll be easy," I say.

"The only problem is that I don't know if I have enough money. This trip just about maxed me out. If it's more than about a hundred dollars, I may not be able to afford it."

"Listen," I said as I contemplated if I should really be making this offer. "If it comes to that, I'd be happy to loan you the money. I know how much this trip means to you and I'd hate for a weather delay to ruin it all for you. Let's not worry about things until they happen. Until then, let's just enjoy the flight."

"That's so sweet of you Brad. I'm not sure I could accept your offer but you know you're right. Let's not think of it right now. Let's just have fun on the way down there and see what happens when it happens. I like the way you think."

As the plane taxied away from the terminal, Kelly looked over with a sheepish grin. "Do you think I could switch over to the middle seat? It'd be so much easier to talk and I just love looking out the window."

"Absolutely," I stammered. Yes, I feel you down there buddy. No, she didn't just offer to give you a blow job, she's just sitting a little closer. Relax man. Everyone else has these conversations with their dick right?

She unbuckled, raised the arm of the seat, and slid over next to me. I could smell her much better now and god, did she smell good. I don't know what it was, either some sort of body cream or just some kind of fresh smelling soap but it was absolutely wonderful and sent new waves of sparks to my head and my cock. Muumuu lady, where are you? What did you look like? How much did you weigh? Come on think about that. Just that.

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