Jill’s Island: The story of castaways and a 3 hour tour

A Fantasy

“Call me Jill."

"Some years ago, it doesn't matter exactly how long, I had little money in my purse and having no real desire to go back to college, I thought I would sail about a little and see the watery parts of the world."

"My real name is Gillian. I was named after the star of the X Files.

I'd been at college for two years and, having learnt very little apart from random sex and copious drinking, I decided to take a gap year. A 'position vacant' ad in the local newspaper caught my eye.

'Deck hand required. No experience needed. Good pay, excellent conditions.'
What could be better! An opportunity to wear my bikini and enjoy some sun. I applied immediately.

Captain Jack, the owner of the boat, 'Tadpole', was very easy on the eye. Tall, tanned and looking about 25. His broad chest was barely covered by his t-shirt. The job interview took place in a waterfront bar, The Admiral Benbow Tavern, after work one Friday night. I had a coffee while we discussed the job. He had a beer. He explained that the Tadpole was a modern yacht, fully equipped with all the latest computer technology, so a crew of two was all that was needed. Navigation was computerised. Rigging was automated. Two crew were needed to ensure that someone was watching the equipment at all times. Most things like winches and rudders were computer controlled. He even explained that setting the sails was completely automated!

I was impressed by the workload.
He was impressed by my tits. He couldn't stop staring at them!

I must admit that I was very impressed when he headed to the bar to get another round of drinks, I was on the beers by now, and I watched his arse in his tight jeans as he walked away. Yum.

Captain Jack explained that he had a tour group booked for the next day and if I wanted, I could join them as a trial trip. I wasn't sure that I should start immediately but Jack said it was only a group of five and it was only a day trip. He would be willing to pay me full day rates, in cash!

"We leave at 11am and should be back by no later than 3pm" he said. "Do you want to come down to the dock and have a look at my Tadpole? It's moored just outside."

"It's 11pm! I need to get home," I tried feebly to complain. Jack took my arm and guided me to the pub door. The fresh air hit me in the face, sober me up enough to walk properly. Too many drinks and no dinner had left me a little tipsy. I grabbed his arm. His biceps were rock solid. His arm slid around my waist. I went a little weak at the knees.

I nearly slipped going up the gangway, and 'accidentally' fell into his arms. Our lips met. My body melted into his broad arms. He half carried me to the cabin while we kissed.

He lay down on the bed, his clothes quickly disappearing.

I climbed between his knees. My hands moved up his inner thigh while my fingertips lightly touched his wrinkled balls. His skin was warm. I placed my index finger on the base of his shaft. A long fingernail teasingly scratched him. Bending over him, my breasts hovered above his groin. He propped his head up on a pillow so he could watch as I worked to arouse him. Long strands of my blonde hair fell down to wash across his hips, like a waterfall. Slowly, wisps of hair tickled him. I watched, smiling, as his strength returned to his penis. I was entranced by the way it grew and moved on its own. The shaft straightened. I could see the veins pulsing. I moved her lips a little closer.
Hot breath touched his tip, and his knob lifted up from his belly. Bending over, my tongue pressed into his belly button as my firm breasts fell on either side of his penis. Passionately I kissed his belly button and I could feel him squirm between my breasts. His hands held my head, fingers clamping into my hair. It was oblivious that he wanted me to move down, to suck and kiss his cock, but I didn't move. I wanted so badly to feel him inside my hot wet cunt and if he wanted me to suck his cock, I wanted him to earn it.

I squeezed my breasts together around his erect cock and was delighted to see his ruby red knob poke up between them. A glistening of pre cum helped lubricate my skin. Watching his penis jumping up and down between my smooth milky breasts made me wet between my legs. My fingers snaked down between my thighs, darting briefly into my wet cunt, collecting some of my own juices. I placed two of my wet fingers on his knob as it moved, up and down.

He looked down, watching, as my two perfect breasts fucked his cock. My pale flesh a stark contrast to his tanned skin. Two firm nipples were sliding along his groin. Every time I moved down, my mouth got closer and closer to his cock and he thought with each thrust, "this time, she'll kiss his tip" and each time I didn't.

He knew that soon his arousal would be too much, and he would cum.

"Wait, lover, wait," I cried, feeling the tension in his body rising.

At the last possible moment, I jumped up straddling his hips. Several hands guided his penis as I pushed my aching pussy down on him. I grinned as I felt his knob pushing up against my lips. I was ready. He was more than ready. My cunt swallowed his cock eagerly.

Almost immediately, he climaxed. I flexed my thighs, gripping him, my hips riding him as my own orgasm rocked my body. I could feel waves of cum shooting up into my body until I felt like they would explode out of the top of my skull. My whole body was on fire.

Exhausted, we fell back on the bed. We both needed a rest, before I took his limp penis in my mouth, kissing and sucking until life was restored and I could feel his hot blood pumping into his growing shaft.
We made love over and over again, until dawn.
When the sun first kissed the horizon, he kissed me awake.
"You put on the coffee and I'll get the guest list. It's a bit of a motley crew, but they've all paid up in advance."

Sitting in the galley with our coffees, he showed me the list.
Dr Ernst Grafenberg. A high school physics teacher
Marilyn Minogue, actress formerly of Home & Away
Dorothy Gale, a Kansas farm girl
Mr & Mrs Ernest Howard III entrepreneurs

"An interesting bunch," I said, "good thing we only get to see them for a few hours."
"Yeah," Captain Jack said, "they are due at 11 but by the time they all arrive and get stowed away, we probably won't cast off until noon, so it's only a 3 hour tour."

And so it was, a 3 hour tour, with the skipper of the Tadpole, Captain Jack. Together with the Professor of Physics, Dr Grafenberg, the farm girl Dorothy, the TV star Marilyn and the rich entrepreneur and his wife.

And of course, with me, the first mate, Jill.

After we finished our coffees, I went back and collected my kit and checked out of the room I had rented. With my bag over my shoulder, I waved goodbye to my old life on the land and whistling, I skipped down the dock and ran up the gangplank to board the Tadpole. Captain Jack had kindly said that I could bunk, rent free, on board. I was 23 years old, free and keen to learn everything Captain Jack could teach me, about sailing and sex!

I smiled as I remembered our late night lovemaking. The morning was still young. We had a couple of hours before our guests were due to arrive.
I followed Jack down into his cabin and quietly closed the door. I moved up behind him and put his hands on his shoulders and kissed his neck. I watched as he stood before me and slowly undressed.
First his T-shirt, lifted over his head and shoulders, revealing a broad solid chest. I bit my tongue at the thought of wrapping my arms around that body, sinking my teeth into his sun kissed skin. His hands undid his cutoff jeans and as the boat softly rocked, he dropped them and easily stepped out of them, kicking them across the room.

My eyes widened and I'm sure I smiled in delight as I caught sight of his erect penis. It sprang up as it was released from his underwear and I'm sure it bounced with happiness.

I remained on the bunk, watching the show as he moved towards me. He leaned over me and we kissed. I almost didn't notice as his thumbs hooked under my shorts, easing them off my arse. I arched my hips to help as he gently pulled my shorts down and off my legs. He knelt between my knees. I leaned forward to grab his hips. His hands wriggled around my back to unclasp my bikini top. I wriggled my legs around his waist. My arms were locked around his neck and he lifted my completely off the bunk. My hips were wide open and my cunt was dripping at the thought of his cock. My body slide down his and I was impaled!

There was no foreplay this time. We both knew what we were doing and we both wanted it badly.

I gasped as his big knob pushed up against my clit. I was wet with anticipation and he eased himself slowly into me. I moaned softly as I felt him pushing inch after inch of his hot flesh deep inside me.

My legs gripped him tightly. My arms pulled his chest down on top of me. He thrust quickly.

I screamed as I came. His climax was seconds after mine. His hot spunk gushing deep into my cunt. He pumped twice and collapsed, entirely spent.

Entwined together, we lay still. The sweat dripping down our bodies. My cunt spasmed around his cock, as it slowly lost its firmness. My juices mingled with his. After a few minutes of restful bliss, I pushed him off me, laughing as his cock plopped out of my wet vagina.

I pushed him onto his back. He had been in charge the first time. Now it was my turn.

He was on his back and I was ready to enjoy his taut body. The night was hot and unseasonably steamy, or maybe it was just this cabin! Waves lapped against the boat, making it gently rock. I wanted to lower myself into him and I wanted to rock up and down in time with the ocean. I looked at his cock. It had withered like an old garden hose that had been left too long in the sun. It was limp and almost lifeless. I smiled. I liked a challenge. I'd get him pumping again, pumping his cum across my face!

My hands gently lifted his penis up. It was damp and soft between my fingers. I ran my fingernail up the length of his shaft and softly circled his knob. There was a twitch of life as my nail traced its way back down to the pubic hairs around the base. I was tempted to squeeze his balls but I thought I'd save that for later.
I lowered my lips to hover just above his slowly growing cock. My hot breath drying the wet skin. My tongue snaked out to lick his shaft. I wanted to taste him, all hot, sweaty and salty.

I opened my mouth just as I saw a bead of pre-cum form on the ruby red tip of his cock. My tongue dipped into it before my lips closed around him.

He tasted fantastic!

I could feel his penis throb as I slobbered all over it. It grew in my mouth, getting hard and firm. I kissed the base near his balls and I could taste my own juices. I licked my lips before carefully kissing both of his balls. Gently I took them, one at a time, into my mouth. I wanted to suck all of my juices off him.

I felt his body moving beneath me. His hands guiding my hips towards his face. I almost choked on his cock when I felt his hot breath panting on my wet pussy. I squirmed as his tongue touched my delicate flesh. I had to spit out his cock as his mouth closing on my engorged lips made me squeal.

I wriggled my bum and pushed down on his face. I clenched my teeth as waves of passion rocked my body. I shook my head. I had to concentrate on the job at hand and that job was my hand on his firm penis. My fingers were wet and slick. I took a firm grip on the base of his shaft and slowly, at first, pulled up. My pace increased.

My fingers teased his tip before pushing down the shaft.

"Have you ever felt a pussy as tight as my hands," I asked. He mumbled something in response but my juicy cunt muffled all the words.

I could feel him wriggling between my legs as he struggled to speak. Finally he managed to splutter.

"The guests!"


I don't know how I did it. Somehow I achieved the impossible. I was dressed in my best bikini with the Tadpole all clean and ship shaped. Food and drinks were all prepared and set out on deck, ready and waiting for the first of our passengers and it was only 10.55am.

The "Welcome Aboard" cocktail party was in full swing with all guests on board and accounted for when I slipped the mooring ropes, hauled in the gangplank and cast off. With the Captain at the helm of the good ship, Tadpole, taking us carefully out of port, I had a chance to settle back and study our passengers as they mingled on the deck.

My eyes were immediately drawn to the Movie Star, Ms Marilyn Minogue. She was short, maybe 5'2" or 5'3". It was hard to tell. The heels on her designer shoes added at least 7 inches. Small, tight gold lame' hot pants barely contained the sweetest, firm arse. Peachy! Tiny wisps of string secured her halter style top, leaving her entire back uncovered. The first gusts of the cool ocean breeze highlighted her tiny nipples as her breasts bounced freely under the scrap of gold fabric. I giggled at her broad Australian accent.

Marilyn was making small talk, Hollywood style, with the billionaires. Mr & Mrs Ernest Howard III were young, I thought, for billionaires. For some reason, I expected Uber rich people would be much older. He was in his late 30s and she was only a couple of years younger. I suppose that inheriting millions as a teenager from your doting grandparents, and turning that into billions before turning 21 via the stock market and a couple of cheeky tech companies means your lifestyle is short on physical labour and high on luxury gyms and personal trainers. He was tall, tanned with dark hair. His wine barrel chest was barely covered by a Ralph Lauren shirt. His designer brand cargo shorts had far too many pockets but they looked great on his firm peachy arse.

Mrs Bunny Howard was mid 30s looking mid 20s due to some very expensive cosmetic work. Everything was firm, rounded and pointing in the right direction. Her designer dress was very floral, sheer and probably cost more that it cost to build the Tadpole. She appeared to be very shallow, but deep down she probably was.
At the other end of the deck, farm girl Dorothy, was deep in conversation with physics professor Dr Grafenberg. I wandered over with a tray of drinks and eavesdropped on their chat.

"And so, by reversing the polarity you can align the interface and automatically set the time on your microwave."

"Wow," Dorothy said, "that's awesome. If I had a boyfriend, I'd wish he was as clever as you. Back in my hometown of Adverse Camber in Kentucky, none of us had high fangled things like microwaves."

"Of course," continued Dr Grafenberg, "the microwave is often thought of as a complex piece of technology, but it's not that complicated. I'm sure that I could build one."

Dorothy was wearing a pair of tight faded jeans and a little T-shirt, cutoff to highlight her toned midriff. I guessed that she was about my age, early 20s. The Professor of Physics was mature. His tweed jacket with leather elbow patches, thick horn-rimmed glasses and comfortable trousers meant he could be anywhere between 30 and 50.

I took a drink up to Captain Jack at the helm.
"Thanks little buddy," he said as he gave me a quick kiss on the cheek. "You better get some sunscreen on those girls. I can see lots of bare skin and it will quickly burn on a day like this."

"Aye aye skipper," I replied. "I've got a good party idea." I ran down to the cab and quickly changed into my string bikini. It was incredibly small, with 3 tiny bits of fabric barely covering anything. It was a guaranteed attention grabber and I wanted all eyes on me. Snatching half a dozen tubes of sunscreen, I ran up on deck.

"Hiya, anyone want to put some lotion on my back?" I wasn't surprised when both Dr G and Mr Howard volunteered. What took my breath away was the eagerness from both Dorothy and Marilyn.

"Steady on girls," I cried as I threw a couple of tubes of lotion to the boys. "Many hands make light work."
I was quickly surrounded by eager bodies, hands covered in lotion clutching at my skin.

I laughed as my bikini top was 'accidentally' undone. Delicate female hands started to caress my boobs. I watched as Mr Howard slipped out of his shorts and shirt. Mrs Howard was also naked and squeezing a whole tube of lotion onto her body. Mr Howard pushed up against her and they squirmed together.
The Professor of Physics was standing naked behind Marilyn, massaging lotion onto her bare back.
Before long, the deck was covered with naked bodies, slick with lotion.

There was no risk of sunburn as everyone writhed in ecstasy. Unfortunately, there was a serious risk of a change in the weather. Dark, ominous clouds were forming on the horizon. The temperature dropped as the winds picked up. Captain Jack ran to the helm. The image of his toned body, naked in the storm, as he struggled to control the Tadpole, will be forever etched into my brain.

I thought I was incredibly lucky to get all of our passengers safely below deck as the waves grew higher and higher.

"Get dressed and stay here," I told them, shouting to be heard above the storm.
I ran back on deck, as waves almost as tall as our main mast, crashed across the Tadpole's deck. A flash of lightning revealed nude Jack as he fought to keep the boat steady. I cowered as the thunder broke directly above the boat.
Cold sea spray whipped my naked body as I struggled to keep the endless waves from breaking into the Tadpole and sinking us all.

Down in the cabin, five people were on the verge of panic.
"This is not the scenic tour I paid for," complained Mr Howard as he struggled with his sun lotion smeared clothing.

Dorothy moaned, "we will all be killed. These giant waves will crush us all."
"Not exactly, my dear," lectured Dr G. "We will surely drown first."
"Oh,"cried Dorothy, "I'm too young to drown. There are so many things that I've never done!"
"Come, my dear, let me hug you," said the good Doctor, wrapping his arms around her naked body, feeling her flesh slick with lotion.

"I can't die like this," she sobbed quietly into his dark eyes, "I've never been with two men before."
In the crowded cabin, Mr Howard turned towards Dorothy, a gleam in his eye. "If it's something that you really want," he offered.
Dr G smiled, "if you think it might distract you from the fear of the storm, I'm happy to assist."

"I've always wanted to have a man shoot his hot cum into my mouth while another man unloaded deep inside my tight young pussy, but I've always been too shy. I don't want to die with my body empty of cum," explained Dorothy as she positioned the Professor of Physics behind her.

"Please Mr Howard, stand here," she instructed, "so I can bend over and suck on your monster cock." Bending at the hips, her firm arse was pointed directly at the Professor. "You can suck my pussy first if you want," she offered him, "before you skewer me with your dick."

Meanwhile, Mrs Howard was seeking comfort in the arms and lips of Marilyn the movie star. The two women hugged and kissed, trying to keep their balance as the boat was tossed around.

"Dearest Marilyn, I've always been a fan of yours. To die in your arms with your fingers inside my cunt and your lips on my breasts would be a dream come true," Mrs Bunny Howard said as she passionately kissed Marilyn.

"I've always wanted my fans to come first," Marilyn replied, "and I would be so lucky, so lucky, lucky, lucky if you would come in my arms."

Back up on deck, the storm raged on. It seemed like days, but was probably only a few hours, as the Skipper and I battled nature.
We formed an expert team, working together instinctively. Jack steered into the waves, avoiding the risk of being capsized, while I manned the pumps, keeping the Tadpole above the wild water.
Just as I was beginning to give up, totally exhausted, the wind and waves dropped. I staggered to the helm in time to catch Jack as he slumped totally spent.

Side by side, we collapsed on the deck as the Tadpole finally entered calm waters. We drifted aimlessly across the ocean at the mercy of wind and tide.

Neither of us noticed as one final wave picked up the Tadpole and carried it across a coral reef, before dumping it onto a white sandy beach.

We were stranded, but alive.

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