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Gillian's Isle

"A ship of fools. You must decide who was the biggest fool. Hopefully not the Author."

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Competition Entry: Foolish

My name is Gillian. I am the captain of a yacht called the Squirter. I am not your typical crusty ole ship captain. Most men and some women find me attractive if I may be so bold. I am blonde, brown eyes, and thirty-four b breasts. I have had my share of semen or is it seamen?

Please sit back and let me tell you about a four-hour cruise that went amuck. I have a first mate named Bob. Let us say Bob is not the sharpest tool in the shed. His parents named him Robert, but he goes by Bob. That way, he can spell his name backward or forwards. Bob is hardworking but dumb as a rock.

Why do I keep Bob around, you ask? Simple, he is hung like a horse and has a tongue like Gene Simmons.

Before each charter, Bob would give me a good licking. He used his tongue on me to get my motors humming. He then would bring me to climax using his monster-sized eel. Sometimes in the throes of passion I would call him by my pet name for him. I called him my little buddy. He would call me skipper. That would make me so horny.



Sorry for the blank spot. I was daydreaming about sea serpents suddenly. Now, where was I? 


That is right—our four-hour tour. Let me start with our guests. There was the Fowls. Mr. Fowl was a billionaire many times over. He is handsome in a Mr. Magoo kind of way. He had glasses that used more glass than the Hubble telescope. Mrs. Fowl? Let us say that it was a good thing Mr. Fowl could not see well. She was a high society sort that looked like she had kissed a train.

There were two supermodels. They had bodies that would make men drool. The first was known as Moi. She changed her name so that she would be known to have a single name like so many famous people had done. You ask what did she change her name from? It was Krissy Brinkley. She thought that did not sound like a supermodel's name. That is right. She is in the same gene pool as Bob.

The second model, not to be outdone by Moi, changed her name as well. She changed it to Me. What did she change it from, you ask? Kathy England was her name before, and she had the same rational as Moi did. So now there were three rocks in the same gene pool.

That brings me to the last guest, Mr. Wizard. He was a rocket scientist, auto mechanic, biologist, astrologist, meteorologist, proctologist, seamstress, gynecologist, and food critic. He also had hobbies like gardening and fishing.

My charter guests were like this most of the time, but this group took the cake. I always had Bob ready the yacht. He loads the guests' belongings. Sometimes they would bring a day bag. He checks the weather and makes the yacht seaworthy. I usually board the Squirter after they all board and the yacht is ready to go.

Bob and I would greet all the guests and welcome them to the Squirter. I would dress in my Captain’s short sleeve blue polo shirt and my Captain's hat with Bob in his long sleeve red first mate shirt and his inside-out sailor’s hat.

This time I went to the captain's control room and could not get in as luggage blocked my way.

I screamed out, "Bob, come to the captain's room."

He came running to me and asked, "What can I do for you, Miss Gillian?"

I asked him, "Bob, how many times have we done this cruise? Never mind, do not answer. How am I supposed to get the ship started if I cannot get to the controls? What is all this luggage for?”

He replied, “Part of it is the Fowls. Mr. Fowl takes most of his billions in luggage wherever he goes. Part of it is Miss Moi’s and Miss Me’s. They both like to have several months change of clothes with them. Mr. Wizard likes to have all his tools with him for all his occupations.”

As I rolled my eyes I asked Bob, "How long is this charter?"

He said, “Four hours, Miss Gillian.”

I told him, "Do you think all this luggage is necessary for four hours?”

In one of his brilliant retorts, he said, "Oh."

Bob moved all the luggage full of money, clothes, and tools to the galley so I could get the yacht underway.

The tour started pleasantly. All the guests moved up to the sundeck. They all seemed to be enjoying the weather and drinks. I did wonder what a group like them were talking about. I am sure the topic of their discussions had to be quantum physics.

Looking in the distance, the sky started turning black.

I called Bob up to the bridge and asked, “Did you check the weather before we left?”

He said, "Yes, Miss Gillian, and it showed the weather onshore as being nice and sunny."

Shaking my head, I asked him, “Are we onshore?”

As usual, Bob had another brilliant retort, "Oh."

Before he could say another word, the tiny ship was tossed around. We were in the middle of a hurricane. I stayed at my post as Bob gathered the guests and gave them life savers. He forgot the life preservers. Me and Moi fought over the lemon-flavored ones. He then had them huddle in one of the bedrooms.

The following day, we woke on an uncharted desert isle. My beloved ship, the Squirter, had a massive hole in her hull. All the guests sang our praise; saying the Squirter would be lost if it were not for our bravery. They kept saying the Squirter would be lost. It almost sounded like a theme song.

We all decided the first order of business would be to find food and water. The Fowls volunteered for that task. Mr. Fowl was blind as a bat, but we hoped he might fall into a hole filled with water. Mrs. Fowl, with her looks, could scare any animal out of its hiding place or any fruit off a tree. Bob and Mr. Wizard decided they would be best suited to build a crude shelter. That left myself and the two supermodels, Me and Moi. The three of us. We decided we were best suited to go lay on the beach and catch some rays.

We laid on the beautiful sand beach. The smell of the ocean and the waves breaking on the rocks it was like a postcard from a resort. The only thing missing was civilization.

Moi and Me started talking about sex and how they would miss it being stranded on this uncharted desert isle. I listened to them complain for about thirty minutes.

I got tired of it and cleared my throat and asked both, “Have you ever had a bisexual experience?”

Moi said to me, “You must be kidding. I would never.”

I said in a harsh voice, "No, I am not kidding. Since I am the captain, I order you to take off your bikini bottoms. I glanced over at Me and told her; you do the same."

Both looked frightened of me and did what I said. I also think they were curious.

I told Moi, “Lie down in the sand and spread your legs.”

I told Me, "I want you to watch me, and when I bring Moi to a climax, I want you to bring me to one. So, pay attention."

Moi had a perfectly waxed pussy, and Me had a nicely trimmed one. I became moist just thinking about my lips on Moi. The thought of Me licking me gave me goosebumps on a ninety-degree day.

I began licking Moi. She tasted like cotton candy. I could tell she was apprehensive about me licking her. That soon faded away to pleasure as she began to moan. I ran my nails down her legs as I tickled her spot with my tongue. Swirling my tongue in her folds as I started finger fucking her. With my ass in the air, I soon felt Me’s tongue on my pussy.

She asked, "Is this what you wanted, El Capitain?”

I looked at her, nodded, and told her, "That is exactly what I wanted."

If this was Me’s first time eating a pussy, she either watched me closely or was a liar and had done it before. She soon brought me to an orgasm with my juices soaking her beautiful face.

Moi’s moans soon became screams of pleasure. I had to muffle her so the rest of the castaways would not hear.

The three of us spent the rest of the morning trading positions. Me and Moi in a sixty-nine position as I watched. Myself eating Me as Moi watched. It was a constant changing of who watched and who was in on the action.

The three of us stood up to a chorus of applause. It seems Bob and the rest of the castaways had been watching for some time. Bob even masturbated and came on a coconut that Mrs. Fowl had found. Now I knew where coconut cream comes from.

After the three of us returned to a normal skin tone instead of the bright red face of embarrassment I tried to change the subject and asked, “How did you make out Mr. and Mrs. Fowl in your search for food and water?”

Mr. Fowl replied, “We found a stream of water that was endless and a supply of fruit that will last us a lifetime."

Bob spoke up and said to me, “Wait to you see what Mr. Wizard and I did.”

I said, “Let’s go see.”

We walked to see what they had done. On the way there, I thought I saw faces in the bushes but blew it off as having been in the sun too long. We all came to a clearing, and I stopped. What I saw seemed impossible.

Mr. Wizard spoke up and said, "As you can see, Bob and I have made some crude huts. There are five of them. Me and Moi can share one. The Fowls can share the one with the king-sized bed. The rest of us get our own huts with queen beds.”

I said, "Wait a minute, we have beds?"

He said to me, "Yes, we all do. I made them out of some of Me and Moi's clothes and stuffed them with Mr. Fowl's money. I used some of the palm trees Bob cut down to make our huts.”

I thought back and how I scolded Bob for all the luggage and now who was the fool. I was, apparently.

I asked him, “You did all this in just a few hours?”

He said, "It was easy with a helper like Bob, and there is more to see. The stream that the Fowls found, I used that to give us all indoor plumbing.”

I shook my head in disbelief and asked him, "What is next, air conditioning and refrigerators?"

He looked at me and smiled, then told me, “That will have to wait. I am working on making us a car to drive around in.”

I thought this is getting ridiculous and asked him, "Why do we need a car? There are no roads here."

He replied, “I am working on the freeway system as we speak, and I will put that next to the high-rise buildings that we will build.”

I said to him, "Excuse me, I do appreciate all that you have done. Have you thought about putting some of that energy into getting us rescued?"

It was apparent that he had been hanging around Bob too long when he replied, "Oh."

I thought all of this must be a dream or maybe I was magically transferred to a cartoon or a television sitcom. I would not have been surprised if Wylie Coyote showed up and he finally caught the Roadrunner and was fucking it in the ass. Beep Beep indeed!

It had been a long day. We all decided to go sleep on our money mattresses. I still had that feeling we were all being watched, but I was so tired from all the sex I needed the sleep.

I woke the following day and felt like a million dollars, literally. I never knew money felt so good.

Mr. Wizard and Bob had made a lovely dining table for all of us. They also made loungers, all made from local trees and palm fronds.

Bob had made breakfast for everyone. It was a nice fruit salad, and a glass of coconut milk served in hallowed out coconuts.

After breakfast, Me whispered in my ear, "I would like to learn more about eating pussy. What do you say we go back down to the beach, and you coach me and Moi some more?"

I whispered back to her, "I would love to, and this time I will bring Bob along. He has a tongue like an anteater.”

I stood up and said to Mr. Wizard, “I need Bob today. We have some urgent business to attend to on the beach. Your freeway will just have to wait a day or two. Maybe you could spend some time today thinking about how we get off this uncharted desert isle.”

Mr. Wizard replied, "That is fine. You take Bob today. I am a little tired today anyways."

I grabbed Bob by the hand and told him, "Come with me. I will show you what I need you to do today."

Moi and Me followed us down to the beach.

We got to the sand, and all three of us stripped naked. Then I told Bob, "Today, you are in luck. We are going to allow you to eat all three of our pussies, and if you are a good boy, you might even get to fuck all three of us."

As predictable as the sun rising, Bob's pole began rising too.

Bob said to me, “Whatever you say, Miss Gillian."

Bob began eating Moi as I and Me watched.

I was beginning to feel like a voyeur with all the sex I had seen the last couple of days.

I then gently started playing with Me’s pussy. I had Me lie down in the sand so I could give her a good licking. She was wet as the ocean. So was I. I flicked her clit with my tongue. She grabbed my hair and pulled me in closer. Her scent filled the air so much I could not smell the ocean.

I stopped for a minute and asked Me, “Have you ever tribbed before?”

She replied, "No, what is that?"

I told her, “Lay back and open your legs and I will show you.”

We began rubbing our pussies together. She pushed into me harder and harder.

It was not long before we heard the moans of pleasure coming from Moi’s mouth. Bob’s third leg was hard as a rock.

Moi screamed out, "Do not let him stop, Gillian. Gawd, I love this.

This was becoming an orgy of sorts.

I then suggested to Moi and Me that we let Bob Fuck all three of us.

It took a nanosecond for Moi to yell out, "I want to be first."

I nodded my head at her.

I told Bob, “I want you to fuck each of us but for only fifteen seconds at a time. Just move from one to the next until you are close to cumming. I do not want you to cum in any of us. I want to take your load in my mouth. I think I will need the protein. Fruit does not provide much of that. Do you understand me, Bob?"

He replied, "Yes, Miss Gillian."

We all laid next to each other, and Bob did as I instructed him to. When he slid his sea serpent into Moi, her eyes about bugged out of her head. When he pulled out and moved onto Me.

Moi whimpered, “I want more.”

Me told her, “It is my turn.”

She had about the same reaction as Moi. I was used to Bob’s girth and length.

Bob lasted almost thirty minutes before telling me, "Miss Gillian, I cannot hold it anymore.”

I grabbed his cock and finished him off in my mouth. He came so much it dripped down the side of my mouth.

I looked to the side of Bob and back about twenty yards I saw the bushes move, and I know I saw eyes looking at us. I have had this feeling since we first stepped on this beach, and now, I was becoming more alarmed that we were not alone here.

As I pointed to the bushes, I whispered to Me, "Look over there. Did you see the bushes move?”

She shook her head no.

I was beginning to think the sun was making me lose my mind.

Life went on for several weeks with no fundamental changes. Mr. Wizard and Bob worked on the freeway now that they had built a car powered by pedals. They also took what was left of the radio from the Squirter and made a stereo system for us. The supermodels and I would have almost daily sessions of sex on the beach. Bob would join in when I let him. Sometimes the Fowls would watch us as they fished for food. I never knew I enjoyed exhibitionism, but sex almost seemed empty without an audience.

I kept pushing Mr. Wizard to come up with a plan to get us rescued. Nothing ever seemed to budge him from the idea of a freeway system. I was losing my patience with him and the rest of the rocket scientists were beginning to get on my nerves as well. Bob needed to be told over and over what to do.

One day Moi asked me, "Why do you treat Bob so poorly? He always does what you ask him to do. I do not understand why you yell at him.”

I told her, “You do not know Bob like I do. He is an idiot. He works hard, I agree. He wears me out, having to tell him the same thing over and over. I hate to sound like a bitch, but please stay out of my business with Bob."

One night this all changed. All of us were kidnapped by a tribe I thought to be cannibals. They took us to their village, where they tied me and Mrs. Fowl and the two supermodels to stakes. They bound the three men and sat them down right in front of us. I just knew they were going to bar-b-que the four of us.

They lit a huge bonfire right behind us. I started crying, thinking this was the end. I was going to end up a T-bone for some cannibal.

They took mine and the two supermodel's clothes off until we were naked. They then put all our clothes on Mrs. Fowl to cover her up.

At least they had some taste.

Who I thought to be the chief started speaking gibberish.

I looked over at Mr. Wizard and asked him, "You are the one with all the brains. Do you have any idea what he is saying?"

He replied, "I am fluent in over one million dialects in the universe. Oops, I thought I was C3PO for a minute. Sorry, wrong story. I do understand some of it. They are a tribe that came from a big island here. I think he meant Jamaica. The tribe is known as the Longadong’s.”

Some of the tribe started playing some instruments. One played the drums, and others played what looked to be crudely fashioned guitars. The rest of the tribe broke out singing Jamming by Bob Marley.
That let us know Mr. Wizard must have been correct, and we were near Jamaica.

The entire tribe started dancing around us as they sang.

I thought they were having some dinner music before we became the main course. I was right in a way.

A couple of the Longadong males took their loincloth off, and I now knew where the tribe got their name from. Their cocks made Bob’s cock look like a Vienna sausage.

They did not have us for dinner, although they ate us. Their tongues were magnificent. They had tongues as long as Bob’s. Soon the males took turns fucking each of us as we were bound to the stakes. I never came so much in my life. I could tell Moi and Me had the same experience.

The rest of the castaways watched, as did the entire tribe. I knew I liked exhibitionism now, but this was a bit much.

This lasted most of the night until all the male Longadong’s came.

This became a breakthrough for us. Soon all of us were close to the tribe and became fast friends.

We discovered how the tribe jumped from one island to the next. What they did was lay three of the male Longadong’s on a raft side by side. Then three females Longadong’s would put a sail on their cocks then push the tiny raft into the ocean where the women would start masturbating the men. The men became hard. Their poles would rise, and the sails would catch the wind, and off they went.

There was one small problem, and many Longadong’s perished from this plight. If one of the males came before they made shore, two could probably get them to their destination. If two came, it became very iffy. If all three came, they were doomed.

Bob became very friendly with a lot of the female Longadong’s. They liked him because he did not stretch their pussies as the male Longadong’s did. They felt pleasure instead of constant pain.

I suggested that we try and make the trip on a raft with the Longadong’s. That was met with a chorus of "Not a chance.”

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Or my personal favorite that Mrs. Fowl told me, "You go masturbate those poles yourself. Best of luck."

The days turned to months. There was much to like about our imprisonment on the uncharted desert isle. Sex was the best with always fresh food. The weather was unbeatable except for the occasional hurricane.

I grew tired of the models and the rest of the castaways. It was hard to live around such dumb people, no matter how good the sex was. What I would give for a cheeseburger and fries or a juicy steak.

After repeated attempts, Mr. Wizard consented to try the raft trip.

I asked him, “Can’t you build something better than those flimsy rafts? You built huts and a car, and now the freeway is about done. You must have something better in mind?"

He replied, “I have not given any thought to it, and I am sure I will be fine on the raft.”

We all became worried because, without Mr. Wizard around, we might all perish on this island.

The morning came when the tide was right, and off Mr. Wizard went. We waved and watched from the shoreline as the women masturbated the men, and the sails caught the wind.

The trip was to take two days, and we heard and saw nothing for a week. I felt so bad pushing Mr. Wizard, and now he was shark food. I cried myself to sleep that night, making Mr. Fowls money all wet.

One month later, a giant cruise liner parked off our shore. We saw a small boat deploy from the liner, and it was headed our way. We all jumped for joy, knowing soon we could get off this island.

We were happy knowing that Mr. Wizard might have made it.

The small boat arrived, and the first mate told us to pack up we were going home.

I was happy and sad at the same time. I would miss our friends with the giant cocks and the life on the island.

We all came to the shore and started packing several small boats with all the money and clothes.

I asked Bob, “Where are your belongings?”

He replied, “I am not going. I love the female Longadong’s, and they love me. I want to finish what we started here and make this a resort. I even came up with a name for it.

I interrupted him and told him, "Bob, you must come with me. I will never find a first mate like you again."

He said to me, “Are you forgetting you have no boat now?”

I told him, “I will get a brand new one.”

He said, “When and if you get a boat come for me, and I might go with you."

I snarled at him and said, "In your dreams. Goodbye, Bob, and good luck."

He walked over to me as I was about to board one of the rescue boats and handed me a coconut. He then said to me, “Inside the coconut is a letter I wrote to you. You must promise you will not open it until you have sailed at least one day away from this island. Do I have your word on that as a captain?”

I told him, "Sure, whatever you say, Bob."

We all got on the huge cruise liner and were so happy to be headed home. The first thing I did was order a cheeseburger and fries.

I forgot about Bob's letter for almost three days. I was so happy. I wrote a book about our adventures and sent it via carrier pigeon to my uncle Sherwood Schwartz. I think he had something to do with the television show The Bratty Bunch.

One night I decided to read what Bob wrote. I was not even sure he could write. The letter read as follows.

********************************************************************
Dear Miss Gillian.

It has been my honor to serve as your first mate for almost ten years. I loved all the times I could taste your pussy and loved it even more when I got to fuck you.

There is a thing or two I would love to clear up about me.

Number one, I did not think you treated me very well some of the time. I took it because I cared about you. You were never able to pick up on that.

Number two, I know you always thought I was dumb, stupid, or a nitwit.

I want to clear that up. My IQ is over one hundred and seventy-five. I am a member of the Mensa society. I taught at MIT and Oxford. I was the chief engineer for NASA. I could go on, but I think you get the message.

Mr. Wizard was brilliant, but he lacked being able to put that knowledge to any practical use. What was done on the island was all me as far as ideas go. He helped with the labor, and he was good at cooking. He also could translate the Longadong’s language, but so could I. I asked Mr. Wizard to take all the credit so I would not blow my cover as being a fool.

If you wonder why I pretended to be dumb, it was because I was tired of the pressure of teaching, NASA, and all the other things I was doing. I wanted a simple life, and your yacht provided me with that. You were a bonus that I did not see coming.

I never finished telling you the name of the resort as you interrupted me. I am going to call it Sandals resort.

I hope you treat this letter with the intent it was meant to have.

Best regards, Bob.

P.S. I will never stop caring about you.
*************************************************************************

I thought what an asshole. He was sending me a Dear John letter.

Like anyone would go to a resort named after shoes. I do not care what the letter said; he was dumb as a rock.

‘It did not matter. I was safely on my way home with the supermodels and the Fowls. We all loved this new ocean liner, the Titanic.

 

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Written by AAnna
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