The Short Happy Life of Island Billy - Cover

The Short Happy Life of Island Billy

Copyright© 2016 by D.T. Iverson

Chapter 2: Ascent

Romantic Sex Story: Chapter 2: Ascent - As I mentioned yesterday. I have a series that I wrote over the period of a year and a half. All of these were written for different reasons. But they fit into a single narrative. Since this is a do-over I decided to repost them that way. This is Millie's story. It is the second in the series that began with, "A Totally Unromantic Love Story." If you recall Millie is the youngest of the Wilson sisters. Please enjoy and thank you for reading me. - DT

Caution: This Romantic Sex Story contains strong sexual content, including Consensual   Romantic  

Buster and I were sitting in the cockpit in the already blistering midmorning sun. I was having coffee and watching the parade of tourists strolling by. He was watching whatever dogs watch when they are staring blankly off into space. We were tied up at the Rodney Bay Marina. The place is one of those “full service” marinas that offers everything from diesel to high end shopping. So, it attracts a lot of tourists.

In the ten months since my divorce Buster had gone from companion dog to best friend. I had let my lawyer Bernie handle all of the details of separating me from Janet. And Bernie helped both of us get through that sad event with dignity. More important, he did it quickly and without bothering me.

As a result, I now only thought about Janet twenty times a day. In the year since I had shoved off from the Marina in DC, I had totally deconstructed the boring guy I used to be. And I had replaced him with the inner boat bum that I always knew was lurking in there.

I was outside in the tropic sun, doing all the chores that you have to do to keep a boat shipshape. Which gave me a deep water tan. My naturally blond well barbered hair was long and shaggy and it had been bleached almost white. And my sedentary body had been leaned down to the bone. I even sported a 39-year old’s version of a six-pack.

I lived in a pair of boat shorts. I added a t-shirt and sailing cap when I was dressed for public consumption. Looking in the mirror I would think, “If Janet could only see me now.” I didn’t recognize myself.

I was supplementing my generous University stipend by doing offshore tours in the boat. I’d take tourists out for a day of sailing and poking around the nearby islands.

I had enough to live on with my regular salary. But I like luxuries so I did tours. It wasn’t making me rich but I could have probably lived in St. Lucia for the rest of my life at a certain level of comfort. Meaning I could afford the REAL Cuban Cohibas.

And staying on St. Lucia was getting to be a very tempting prospect. Jean-Claude was my agent. He was a happy rastaman who lived somewhere up near Soufriere and spent his time on the beaches hawking outings for the tourists, among his other products.

Actually, tours were one of Jean-Claude’s more savory lines of business. I gave him twenty percent of anything that he brought my way. I had met him my first week on St. Lucia. I had reserved a slip in Rodney Bay for the duration of my stay and there was a place just off the dock called Spinnakers that had the right insouciance. Meaning, it was also handy enough that I could crawl back to the boat if I had too much to drink.

The feature that sold it though, was that they let Buster sit with me on their outdoor patio. The island IS French after all. I had been in that place every night since my arrival, drinking and trying to figure out the local scene. Buster would sit next to me, pant-pant-pant-slobber-slobber-slobber, looking attentively for anything that dropped on the floor.

I had just come down from the States. And I was a pasty-faced tourist back then. But I was quickly getting the lay-of-the-land and I was becoming a whole lot more comfortable in St Lucia. Jean-Claude came over and introduced himself about a week and a half after I had arrived and started hanging out at Spinnakers.

He was wearing an ensemble that could be best described as “weather beaten”. It was a type of ratty island chic, old aloha shirt and frayed shorts that looked like they had originally been long pants. He was coal-black. And he had one of those animated personalities that would have made Bobby McFerrin seem downright “Un-Happy”.

Jean-Claude was playing cheerful island creole when he came over. I knew he was trying to hustle me. But I asked him to sit down. Any guy who could game that well had to be knowledgeable. I bought him a drink and told him I had just moved down there and I wanted to learn how to thrive and prosper in the St. Lucia culture.

I told him that I thought he looked like the right guy. So I offered to pay him to teach me all of the things I would need to know to be successful in his society. His demeanor changed from happy to sly. I could see he was figuring the angles. I could also see that he was a very smart fellow indeed.

He switched into perfect French accented English and said, “How about you hang with me for free Mon Ami. I’ll teach you enough that they will think you were born here. And you can buy all of the food and drinks.”

I laughed and said, “Why do I have the feeling that I would have been better off if I had just handed you a couple of thousand dollars?”

He laughed and said, “You would be. You would be.”

That was the beginning of a beautiful friendship. Most evenings he and I and Buster would sit around Spinnakers listening to the music, which was really quite good. Then Buster and I would walk back to the boat and Jean-Claude would wander off to find another mark. He never seemed to sleep.

Jean-Claude took me everywhere and introduced me to everybody and by the time he was done I felt like I could have run for Mayor. One of the most disturbing outcomes of my divorce was my total lack of interest in sex. In fact, you could even extend that malaise to cover my attitude toward women in general.

I don’t know whether the fear of betrayal was keeping my desire for female companionship bottled up. Or it was a case of sexual dysfunction due to my sudden change in fortune. But I had no interest in interacting with any woman, no matter how hot she might be. In fact, it took six months after the day that Bernie informed me that I was single once again, before I began to even look at any woman in “that way.”

I was now at the point where I could appreciate a tight female body in a skimpy outfit. But I was still very aware that every one of their beating hearts was full of duplicity. At that time of year there are slightly more cruise ships in Castries Bay than there were vessels offshore during the invasion of Normandy. It was still semi-miserable in most cities north of the border. And all of those behemoths were disgorging passengers onto our tiny island.

Most of these people were American and frankly embarrassing. The natives were crowded around them like flies on honey, or another substance. Jean-Claude, must have been in the middle of all of that because he called me and said, “I’ve got a family that wants a tour up to Martinique. Pick them up at the Halcyon Sandals at 10:00. Good money for you and me Mon. The name is Wilson. He pronounced it Wheel-sone”

He said it “Will-sone” Jean-Claude lived for moments like this. The Sandals resort he was talking about was down the coast on the other side of Castries City toward Rodney Bay. I said, “Thanks my friend and you can pick up your share tomorrow.”

He laughed and said, “Slow down, you’re acting like a grockle Mon. I’ll get it by-and-by.” And he hung up. An hour later I was pulling into the Sandals dock under diesel. Buster was sitting splendidly at the prow, looking exactly like a canine figurehead, pant-pant-pant-pant.

I had assumed that the “family” would be dad, mom and the kiddies. But what was waiting for me was a “family” in the sense of brothers, sisters and spouses. There were five of them, two men and three women ranging in age from perhaps the mid-twenties to a guy who looked to be in his mid-thirties.

There was a woman in her early thirties who was slim and had “yuppie wife” written all over her. She was clearly with the oldest guy. Then there was a woman about the same age as the wife who looked so much like the first guy that she had to be his sister.

She was tall. And she had one of those aggressive bodies with the huge tits that scream “hot”. But she was dressed in slacks not shorts, like a “no nonsense” kind of woman. It was an interesting contrast of messages. She was clearly married to the other fellow because she was hanging all over him. Even though he looked to be several years younger.

The woman who was unattached was in her late-twenties. She was without a doubt the younger sister. That one was a total knockout. Not since I first laid eyes on Janet had I ever seen a complete package like the woman standing expectantly waiting for us to dock.

She was in a pair of white boating shorts and a blue polo shirt with an alligator on it. She had thick auburn hair that ran down past her shoulders. It was layered into a medium length waterfall that framed her gorgeous face. She had a golden tan and the most perfectly proportioned facial features. It was like looking at the women in a Vermeer, or a Waterhouse. She was stunningly beautiful.

She was maybe five six and had gorgeous muscled legs and a killer ass. I know that because she was bending down to pick up a cooler as I docked. I nearly rammed the docking fenders gawking at that exceptionally stimulating sight.

When she turned to board my first impression was “athlete.” She had big round full boobs. They weren’t in Janet’s league but very few women’s are. Nonetheless, they perfectly complemented her nubile shape without looking too out-of-proportion big.

She had broad shoulders and toned arms for a woman, and extra-long smooth sleek muscled legs. Janet’s hips are full and round. This woman had tight athletic hips that just radiated feminine power. I had already noted that jutting ass. But when she turned to put the cooler down I could see that her long waist was so narrow that it made her faultless, round hip structure almost voluptuous.

I might have lingered a little too long inventorying her because she caught me staring and looked back at me with total disgust. The Cruising 40 has a big comfortable cabin and foredeck but the cockpit is a little tight with six people and a burly dog. I immediately banished Buster to the galley.

He was happy to go down there since I had laid out some extra rations to keep him occupied. Plus, all of those people were making him nervous. The six of us were distributed around the upholstered benches as I headed back out under power on a course slightly west of north, headed for Martinique. Practically as soon as we hit the open ocean the older sister and her husband disappeared into the cabin. They left me with the impression that they were none too thrilled to be out there. It was like they expected a visit from Captain Jack Sparrow momentarily.

I had every variety of island beer in an iced tub and plenty of rum and tequila down below. The sound of the blender in the galley eased any concern about unhappy customers. They would be content sitting in the cabin with their Margaritas. And it looked like they were there for romance anyhow, not seafaring. Some of my couples are like that. The rolling of the waves makes them horny.

That only left the older brother and his wife and they were cheerfully sitting on the starboard bench watching the water bubble past as we progressed offshore on the diesels. My only thought was. “Empty headed, over-entitled, and rich.” I saw a lot of that type among the student body at the place where I used to work.

As soon as I got into the main ocean swells I raised the mainsail. I could have done it by myself but part of the tour is the opportunity to play with the boat. And so I asked for volunteers to haul sail. The brother looked at his wife and they both shook their heads. It was obvious that they thought that raising sail was something that the bought help should do, not the masters.

I looked at the goddess and her eagerness was written all over her face. She said, “I have never sailed before but I would LOVE to learn how.”

She rose graceful as a cat and came over to where I was at the wheel bringing the boat directly into the wind. Things can get a very interesting if you hoist the main and you are not aligned with the wind on the nose. That was something that I learned to my painful regret on the way down.

I put it on the auto-sailor and wrapped the line for the mainsail hoist over the power assist. I said, “We are going to need this to raise the sail. Once I finish unfurling it I want you to pull the line through this winch. Don’t stop until you get to the top of the mast. Can you do that?”

She said eagerly, “Aye-aye Captain.”

Her look was akin to a little girl concentrating on riding her first bike. It was so endearing that I almost forgave her for the “back off creep” that she had been radiating all of the time she had been on the boat.

We got the mainsail and jib up as efficiently l as I did with Janet. The woman was undoubtedly a physical specimen, perfectly coordinated and very controlled and precise with her movements. I wondered if she was a pro tennis player or something. Her rare athleticism was hard to miss.

The sails filled as I turned away from the wind off the nose and we laid over on a glorious port tack making maybe eight knots. It was so exhilarating that she actually cried out and clapped her hands in glee. The look of rapture on her face hinted at deeper feelings in other aspects of her psyche.

I turned back to take the wheel and reset the course for 350 degrees. I said, “Enjoy yourself. There is food and drink below and if you want to work on your tan the foredeck is a good place to soak up sun.”

She gave me the first friendly look she had given me since she came on board. She said, “I love the sun. We don’t get much of that in Ann Arbor this time of year. Can I just sit up front? Will anybody disturb me? How long until we get to our destination?”

I said, “If the wind holds we should be there in less than three hours. That will make it around 1:00 in the afternoon. Then your party can decide what you want to do from there. You can stay on the island for a couple of days, which I suggest. I will pick you up whenever you want to come back.”

I added, “The other option is to make it a day trip. We can run back around 7:00 tonight. I am up for doing whatever makes you folks, happy. You are the customer.”

She said, “Can we decide when we get in? What is Martinique like?”

I said, “It’s the Paris of the Caribbean, ‘nuff said. I like to tour the distilleries but I adore rum and they make some of the best in the world. The shopping there is supposed to be exquisite but Buster and I don’t shop.”’

In the meantime, my canine pal had wandered out of the cabin and was sitting by the wheel. I think the people getting sloshed down there were bothering him. He has turned into a sea-dog which is a long way from his street-dog origins. Of course my transformation from academic geek to beach bum wasn’t any less spectacular.

I offered my hand and said, “By the way, my name is Bill Butler.” I added to be witty, “It’s alliterative don’t you know? Everybody just calls me Billy Joe. May I ask your name?”

She said, “It’s Milly Wilson.” It’s short for Millicent. My sister down below is Marigold.

Everybody calls her Mary. My Brother is Lance, which is short for Lancelot. My parents had very strange ideas when it came to naming their children.

The other guy is somebody Mary picked up at the hotel. I don’t know his name.”

That was interesting. I had assumed that they were married because Mary and the guy were already getting rambunctious. In fact, they had gotten to the point where I thought we were going to have to batten the cabin hatch to dampen the noise.

Both Milly and Lance were completely ignoring that show. Apparently Marigold did that a lot. I said, “Which ship are you off of?”

She said, we flew into Hewanorra yesterday. My sister Maddie and her husband are going to join us here this evening. I used to baby sit their little boy. He is named Billy too. We all adore him.”

Then she realized that she had more-or-less implied that my name was childish and blushed. I said, “Don’t worry about it. I’m from Alabama and every William down there is either Billy Bob, or Billy Joe. So no offence taken.”

I gave her an affable smile and went back to steer. She gave me an odd sleepy smile and went up front to sun herself. Buster just sat next to me slobbering.

I watched the tell-tales on the sails for a little while in order to gauge the wind. When I looked back up the foredeck I nearly dumped the entire boat. She had taken off her polo shirt and shorts and was just spreading out a towel to lie down on.

I expected her to be in some sort of sexy bikini. Instead, she was wearing a microfiber one-piece swimsuit. It covered her entire body in black fabric. And if it had been made out of cotton she would have seemed stuffily modest.

But because the material was one-micron thick polymer every nuance and feature of that absolutely superb female body was visible. It was like she was wearing nothing but black paint.

It was such an erotic sight that I sprang something inappropriate. Thank God her older brother and his wife were watching the wake or I might have been keelhauled on my own boat.

To say that she had a superb body was an understatement. It looked like an idealized drawing of female anatomy. Janet has a body to die for. But it is built for sex, huge tits, tiny waist and the kind of ass and hips that you want to grab two handfuls of and ram yourself into.

This woman was designed for speed and strength, lithe and sleek. I have never seen anything so striking. When you looked at her, an image of a Cheetah, or a Formula One car, or a supersonic fighter plane came to mind, lethally effective and potent. It was the female form as originally intended by the Architect. But perfectly rendered in flesh. It was awe inspiring.

I changed my assessment from tennis player to dancer. You don’t get a body that perfect, tight and yet supple without years of dance training. It clearly wasn’t ballet though. Ballerinas are flat chested. They have to be in order to keep the straight physical lines of the ballet.

This woman had two very big round hills perfectly anchored as high as possible on her chest. Janet’s boobs are massive and of necessity float on her ribs. This woman’s tits didn’t move. It was like comparing a big cantaloupe to a watermelon.

I was actually kind of disillusioned by the faultlessness of her boobs. Because the only conclusion I could draw from their absolute perfection was that she had had bought them. And I am not interested in a woman who would do that to herself. It was just that she didn’t seem like that kind of person. She was the most forthright, open and modest soul I had ever known. I felt the first seeds of something growing.


I dropped my passengers at the Fort-de-France Marina Dock which is right in the middle of the city. The cruise terminal is next door and I was under diesel all of the way across Fort-de-France Bay. That was because I needed the agility to NOT end up under the keel of one of the monster cruise ships coming and going from there like elephants among chipmunks.

I saw all of my passengers off onto the dock and then pulled back into the harbor and dropped the anchors. Coming into Fort-de-France is a little like the approach to Calais, same waterfront and Norman church tower. But the housing that runs all the way up the surrounding hills is pure island creole.

They had decided to just spend the day shopping since they were going to meet their older sister and her family that night. Mary and her boy-toy wanted to stay on-board and drink. But I convinced them that the local distilleries had tasting rooms so it was worth the trip.

Seemingly, the prospect of free high grade rum piqued their interest more than sex. Plus, they had already had enough of THAT to tide them over for a while. Mary was a puzzle. She was clearly a first-class, buttoned-down preppie woman, very much in command. At the same time, she had spent the three hours it took to get over to Martinique drinking and carousing with a stranger who was about ten years younger than she was.

Plus, it was obvious that the two of them had gotten quite friendly in my little forward cuddy. It was no skin off my nose. And I had plenty of spare sheets to change the bed. But the contrast between her uptight exterior and her unselectively voracious appetite was thought-provoking.

Milly spent the time on the way over to Martinique on the foredeck working on her tan. She was alternating lying on her back, and then her front. Whatever side she was lying on, she was so distracting that I stopped looking straight off the bow.

She was comfortable with her family there. And not trying to be exhibitionistic in any way. But the material of the suit was so thin that it was like she was naked. It smoothed out the valleys. So some things were still left to the imagination. But her woman goods were on full display.

As a result, when she was lying on her stomach her magnificent jutting buns and her powerful hips were giving me a hard-on. And when she was on her back her big round meaty boobs were even more disturbing. Particularly because the sun made her nipples sprout to acorn proportions.

Even covered by the suit those two features looked like stalwart watch towers standing proudly on the magnificent mounds of her chest. That vision was making me harder than titanium. And

I am not even going to get into what happened to me when she turned over. For a very short period she was on all-fours in that classic doggy position. The suit kept things from being too explicit. But the outline of those big fat lips in between her full muscular legs was giving me thoughts that I hadn’t had in over a year.

In fact, on the short ride over to Martinique, Milly and that suit seemed to have completely cured me of whatever sexual dysfunctions Janet might have created. It was a fucking miracle! Pun intended.

Milly changed back into the polo and shorts to go into the City. She would have set off civil insurrection among the male population if she had appeared there in that suit. As she was stepping up onto the dock she said rather hopefully, “Would you like to come with us?”

I said, “I would love to but I have to keep an eye on the boat. You guys have a good time. The Rue Victor Hugo is the place where the expensive shops are. And if you want to eat try Chez Carole. The Rum Distillery Tour at Le Diamant is to die for.”

She said, “Thank you” and shyly squeezed my arm. I knew what THAT meant.

Buster and I sat in the sun all day and waited. I normally kill the time playing on the internet, or reading. Today I was just thinking. I had been badly burned by a beautiful woman and I was not interested in revisiting that experience.

But this girl, and she was still only mid-twenties, seemed different. There was something special about her. It was her rock solid sense of personal integrity, which she just exuded. She was a giver, not a taker. And in that respect she was poles apart from Janet.

For one thing she was not a vamp. Janet for all of her intelligence and common sense knew the effect that she had on men and she was always up for using it. Milly either didn’t know that she was smoking hot gorgeous, or it didn’t matter to her.

Janet was a professional games player. That is what all sales people really are. Milly was so forthright in the way that she approached people that she was like the girl next door, almost naïve in her worldview. It was refreshing.

Janet’s intelligence was like a guy’s, always on display for others to see. You could tell how smart she was just by talking to her. Milly might be smarter in some respects. But it was a woman’s intelligence, subtle, nuanced and less conspicuously egocentric.

And did I mention her innate sexuality? She had wanted to burn me at the stake, for checking her out. But there was something in the way that she walked and held herself that made me think that once you got her motor running she might be even hotter than Janet. And Janet was like an active volcano.

Her mention of her sister’s children also fascinated me. We were childless because Janet wanted a career. Milly seemed to have a special love for children. That fit perfectly with all of the other elements of her personality. And I wanted kids.

Using the word, “together” to describe somebody is so 1960s. But that was Milly in a nutshell. She was comfortable within her own skin. She knew who she was and she had nothing that she needed to prove. She was cheerful, open and kind and spontaneously affectionate. And for the first time in almost 14 months I found myself speculating about romance.

That was the point where my little voice reminded me that I was at least thirteen years older than she was. So it was unlikely she would even find me attractive. She probably had plenty of hot young twenty-something studs to take care of her needs at home. But I was wondering if she might like to try an island fling with an older man, just to get me back in the game so to speak.

They finally called at 7:00 and told me to pick them up. The women were loaded with bags and boxes from the nearly Parisian shopping experience that Martinique offers. The older brother wanted to tell me about the Central Market like I had never been there. Then he and his wife went up forward holding hands. It was kind of sweet.

Mary and her boy-pet were sloshed from the rum tour and they quickly retired to the cabin closing the hatch behind them. Definitely an unsubtle hint.

Milly came and sat with me and Buster at the wheel. She was doing that woman thing where they start to want to get to know you better. The sun setting in the tropics is very romantic and it was off our right shoulder in all of its purple and gold glory. She was sitting on the bench next to the helmsman’s chair with her arms wrapped around those fabulous legs solemnly studying me, watching me steer.

I said, “Do you want to try it?” She looked absolutely delighted and said, “Can I?”

I shifted over to let her onto the bench. Her rock hard flank and leg against mine was doing wonderful things for my libido. I showed her the compass and said, “Make sure that little arrow is pointing toward 170 and keep it there. A sailboat is like a living thing. The helmsman, the boat and the wind are all parts of the same entity. So steer by feel.”

She gave me a dreamy look and then went back to steering. She was chewing on her lower lip, concentrating furiously. It was totally endearing. I was aware of that superb female body plastered against my side but it was more like companionship, a bonding experience rather than a sexual moment.

As she steered she casually said, “Were you born down here?”

I knew what she was fishing for. I have not talked to a single solitary person on that island about my former life. I was a boat bum to her and that is the way I was going to keep it. I said, “No, I am from the States but this is where I want to be.”

I didn’t add, “Until my heart heals.”

She said, still fishing, “Are you married, do your wife and kids live here with you?”

I said, “I have neither. It’s just me and Buster.”

She said, “Aren’t you lonely?”

I said, “Once in a while.”

She had no idea HOW lonely I was and I was never going to enlighten her. There was nothing left to say after that. So we just sailed along in comfortable comradeship in the rapidly growing darkness.

I took over when it became full dark. She lay back on the bench with her hands behind her head and said with wonder, “Look at those stars?”

I said, “The Ocean at night puts you in touch with the universe. Reminds you how small and unimportant you are in the great scheme of things.”

For the past 400 or so days I had needed the continual reminder that the events in my life meant nothing to anybody else. It kept me sane. But sitting here with this woman was thawing me out. I was beginning to think of future rather than past. That fact TERRIFIED me.

I dropped them at the Sandals dock. Their tip was generous. Milly had been getting more and more agitated as we came in on the diesels. Finally, she turned to me and said with anxiety in her voice, “Can I hire you to show my sister and her family around tomorrow? They could use a good guide.”

I said, “Certainly, just call this number” and I gave her one of my cards. I was disturbed by how happy that made me. They all trooped up the dock carrying the booty they’d gotten from pillaging the shops in Martinique.

Actually Mary and her beau, who seemed to have fucked several times from the sounds emanating from the cabin, were staggering. And Milly was walking ahead of them with pantherish grace. She was an absolutely stunning woman. A trophy that any man would be proud of.


My phone woke me the following morning. It was 8:00 already. It was Milly and she sounded disgustingly chipper. I had gotten the boat docked and done the usual post excursion maintenance and cleaning by midnight. But for the first time in a long time I drank myself to sleep.

I always keep the door to the cuddy open so I can use the head at night. And Buster always sleeps at the foot of the ladder leading down into the cabin for our mutual security. But for some reason I had closed the cuddy door and it was already getting hot in there. I think that was an indication of my confused state of mind.

Milly said, “My sister and her family want to take an excursion. Can you pick us up at the dock again?”

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