tagCelebrities & Fan FictionGilligan's Island: Temptation 03

Gilligan's Island: Temptation 03


Thank you very much for reading this story and supporting a new writer to Literotica! I'm beefing up this story now. The first chapter was written quickly to amuse myself but now that I'm publishing I want to make it enjoyable for everyone. Eventually all characters will join in the fun as the chapters progress.


Mary Ann bustled around the campsite fixing dinner and getting the table ready while all the other castaways did nothing. At least, that's how it seemed. She cooked, she cleaned, she washed clothes, she even repaired the Skipper's pants that he busted every time he sat down. She was happy to do chores- on the farm she'd rise daily at 5am and sometimes she wouldn't finish until dark. But when there were six perfectly healthy people just mooching around complaining that their dinner was late, she sometimes had naughty thoughts about sticking the soup ladle 'where the sun don't shine'. Six times.

As she put the finishing touches to the mixed salad, Mary Ann couldn't get thoughts of Ginger and Gilligan out of her mind. The look on Gilligan's face as he did that...thing...to Ginger, and the incredible noises Ginger was making. Was that the first time they'd done it? And why did he choose Ginger?

The answer was obvious. Gilligan was horny and Ginger was easy.

Mary Ann blushed at the thought of Gilligan being horny, but it certainly explained a few things. Why he was so keen to get her out in the jungle by herself. Why he kept lifting her over rocks and streams so that his hands went on her behind. Why he kept bumping into her with that hard thing in his pocket. Which she now knew was the biggest prong she'd ever seen, apart from the ones on the bulls and stallions back home.

Shy, sweet Gilligan. Of all people!

Mary Ann would never be 'easy', but the sight of Ginger with Gilligan's loveprobe buried deep between her cheeks set her mind and pussy aflame with longing. She also knew that Gilligan had a low boredom threshold and he would soon get tired of Ginger's constant willingness. He needed an alternative.

And Mary Ann was going to be that alternative.

Smiling to herself, Mary Ann began carrying dishes out to the table where they all sat making yummy noises. She gave an especially big smile to Gilligan, and decided she was going to tempt him with a treat. A special treat. She fervently hoped she was up to the task. It was something she had never tried before, something that the girls across the tracks might do, and she blushed just thinking about it.


Dinner on the island was always a noisy affair. As well as the scraping of forks and the clatter of coconut-shell cups there was Mr. Howell shouting about money and the Skipper shouting about the Navy and the Professor trying to ram scientific facts and figures down everyone's throats every night. Gilligan always finished eating before everyone else because he was so greedy. He sighed and propped his chin in his hand, listening to the droning going on around him and daydreaming about Mary Ann's sexy little tan legs spread wide, her virginal pussy just waiting for a big cock to bust through her cherry.

Gilligan couldn't believe how quickly things had happened with Ginger. He'd only had two or three sexual encounters in his whole life, and one of them had been a prostitute who sucked him off and then stole his wallet. But all those years of pent up frustration had finally taken its toll and had turned him into a man who wasn't prepared to wait any more. He was glad that Ginger was such a horny cumslut. She really didn't care what he called her, or how he treated her, as long as he gave it to her good. The feeling of being in control was very empowering, and he wanted to thank Ginger for it, only it would have ruined their game, and so he decided he'd just fuck her butthole extra hard next time as a way to show his gratitude.

Mary Ann was sitting opposite him, cutting her fish into neat little morsels. Every now and again she'd glance up and blush when their eyes met. The fifth time it happened, he winked. She went deep red and lowered her gaze to her plate and didn't look up again for ages, but he could see a smile playing on her pretty pink lips.

His thoughts, as always, drifted to her tight little virgin snatch encased in those itsy bitsy shorts. Mary Ann had become his best friend on the island after the Skipper, and he'd felt sure she would let him screw her when they first became shipwrecked. But it turned out she was proud of her virginity and wanted to keep it. Still, it didn't stop her tempting him by bending over while she did the laundry, or getting him to give her a leg up onto a rocky ledge to pick fruit. He decided she was repressed, like he had been for so many years, and that once she experienced a hot cock pounding into her tight hole she wouldn't look back.

If there was one thing guaranteed to give him a raging stiffy, it was thinking about reaming Mary Ann from behind while she squealed that it was a sin and then orgasmed like a whore. And he was getting a woody on right now.

"So I said to Ensign Wokowlski, if you don't shift your bony ass into first gear, I'll damn well do it for you!" the Skipper said, banging his fist down on the table and laughing.

"Who doesn't have change for a thousand dollar bill?" shouted Mr. Howell as he recounted a tale about a hapless shoeshine boy. "It's just petty cash!"

"The deepest part of the ocean is 35,813 feet deep and occurs in the Mariana Trench in the Pacific Ocean," the Professor blathered. " I'm sure Gilligan could tell us how deep that is in fathoms!" he added with a chuckle.

Not as deep as Ginger's Trench, thought Gilligan, while he nodded and smiled benignly at everyone.

Midway through a delightful daydream about inserting a pineapple into Ginger's snatch, Gilligan felt something tickle against his lower leg. He squawked and his hand shot out and knocked the Skipper's drink over.

"Gilligan! Watch what you're doing, you nitwit!" the Skipper yelled.

"Sorry, Skipper, there was a bug on my leg!" Gilligan blustered. He tried mopping up the mess but he pushed the liquid off the table and into the Skipper's lap.

"You idiot! Now look what you've done!" Skipper smacked Gilligan's hand away and stood up revealing a large wet patch all over his crotch. "Now I'll have to change my pants!" He stomped off, muttering, while Ginger giggled and Mrs. Howell went "tut-tut".

"The first electronic digital computer was developed in 1946 and contained over 18,000 vacuum tubes," said the Professor, oblivious to what had just happened.

"Just like Gilligan's head," said Mr. Howell.

"Mr. Howell! That's not very nice!" said Mary Ann, defending Gilligan, as usual.

"Well, it's true! The boy is a bumbling idiot!"

"He most certainly is not!"

"It's okay, Mary Ann," said Gilligan. "I'm used to it."

"Well, I don't think it's very nice."

"Mary Ann, it's okay. Really." Gilligan smiled at her, and she smiled back, her cheeks going pink.

It bothered Gilligan that the others would never stop treating him like a birdbrain, but he was grateful for Mary Ann's friendship. She always stood up for him when the others were against him. They were so smug, always convinced everything was his fault, even when it wasn't. But they weren't as great as they thought they were, and besides, did any of them have their own personal fuck slave, like he did?

Next to him, Ginger squealed and babbled every time anyone said anything, even when it wasn't worthy of a comment. This was because Gilligan, in his boredom, had slipped his hand in under her dress and was now idly tormenting both of her moistened holes while he continued to gaze out into the distance with his chin in his hand.

"Ginger, dear, are you all right?" asked a concerned Mrs. Howell.

"Ooooh! Eek! Yes, Mrs. Howell, I'm, eeeek, perfectly fine, thank y-ooooh!" Ginger giggled, trying to move her ass around on Gilligan's hand without being noticed.

Meanwhile, the tickling sensation on Gilligan's leg had reappeared. This time he realised it wasn't a bug, after all.

It was a toe.

He glanced down to see a small, tan foot disappear up his pants leg. He stared in complete disbelief at Mary Ann. She kept her head down and carried on eating, ignoring him completely. Gilligan was surprised and delighted at this new development. The eternal virgin Mary Ann playing footsie with him under the table was the very last thing he'd ever expected. The feel of her toes tickling his leg hairs made his cock swell and harden until he had to spread his thighs apart to get comfortable.

Ginger sidled closer to Gilligan until their arms were pressed together. He buried his fingers even deeper inside her. Her love tunnel was saturated with juices and her inner muscles clenched and unclenched around the two fingers he had inserted. Meanwhile his thumb was deep inside her ass. He was holding her like a bowling ball and he thought how funny it would be to launch her down the alley and into the pins for a strike.

Mary Ann's foot crept up Gilligan's leg to his thigh. He glanced down at her slim, dainty toes and perfectly pedicured toenails. Her small foot was perfect in every way. Her arches were high and her ankles were supple and slender. He liked the contrast of tan skin and smooth, pink sole. He wondered, not for the first time, whether she was tan all over. He sometimes had dreams about her in which she was naked and carefree, cavorting around on the beach like a little water nymph with her long chocolate brown hair hanging loose on her shoulders and a garland of seaweed around her head. Her firm, round breasts would be tipped with chocolate nipples the size of dollar bits and her pubic area would be as soft as velvet. He would catch her by the arm as she skipped by. She would squeal in surprise as he spun her around, and he'd ignore her squeals and hoist her onto his rigid pole, sheathing his monster cock inside her delicate lovenest and putting an abrupt end to her innocence and virginity. At first she would be shocked and bewildered, her eyes wide and questioning, but then she would start bouncing up and down, laughing girlishly while he thrust up hard and deep inside her, full of the joys of life, happy to be joined with him at last. Sometimes when he awoke from these dreams he found he had exploded in a giant mess inside of his pants.

Just like he was about to do now.

Mary Ann's toes were now pressing gently between Gilligan's legs. She tickled and groped the flesh of his inner thighs while above the table she carried on eating her dinner and laughing at the Howells' and the Professor's chatter as though everything was completely normal. Meanwhile, for Ginger, everything was definitely not normal. Gilligan worked on her clit, rubbing it in small circular motions, sometimes grazing directly over it, revelling in the way she wriggled and twitched, knowing how much she wanted to let go and start screaming. He flicked the little wet pearl with his fingernail. Ginger bit down on her fork and murmured softly. Her bulbous breasts strained at her evening gown, her giant, hardened nipples poking through the fabric. He wished he could chow down on her glorious tits while he made her cum like a bitch.

A few more flicks, some more circular rubbing, and Ginger finally started cumming. He felt her entire body shudder on his hand. She leaned forward and lifted her buttocks up and her internal muscles clenched around Gilligan's pumping fingers. Her engorged pussy lips pulsated and twitched and opened up, coating his wrist with rivers of cum. Right at that moment the Professor asked her a question, something stupid about atoms and molecules, which she had no idea about, and she shook her head and made a noise like a mouse caught in a trap while orgasmic tremors coursed through her.

At the same time Ginger was cumming, Mary Ann's foot pressed into Gilligan's ball sack and her toes squeezed his nads. He gasped, muffling the sound with his hand. His fingers flexed inside Ginger's twat and she kept cumming and cumming, gyrating like a pro belly dancer from the waist down while everything above the table appeared relatively normal, although you'd have to be blind not to notice those enormous tit bullets poking through her dress.

Mary Ann laughed musically at the Professor's boring science 'facts' while her big toe played gently over Gilligan's nuts, relishing their firm but spongy texture through the material of his pants. Gilligan bit the inside of his lips, both of them. He started seeing spots in front of his eyes. Mary Ann began stroking his huge erection up and down, up and down, pushing her foot against the throbbing bulge and gently kneading his balls. He pushed forward, she pushed back, and then she began to jack him off with those glorious little brown toes that were tipped with perfect little white nails.

Ginger tried to ease herself off Gilligan's hand but he held her firmly in place. He was going to need something to hold onto when he started cumming. His thumb stayed buried in her sticky ass, his fingers inside her cavernous fuck hole. Mary Ann's toes were gliding up and down his solid shaft and pretty soon there was going to be one heck of a mess inside his pants.

Gilligan couldn't believe what was happening. The two girls who had treated him like their loveable dopey brother for so long were now competing for his sexual attentions in the most spectacular way. He wondered why Mary Ann was suddenly coming on to him- the coy little virgin had always kept him at arm's length. The only thing he could think of was that she knew he'd started banging Ginger. It was probably written all over Ginger's face that she had spent the whole afternoon fucking like a bitch in heat. Her eyes were vacant at the best of times, but now the actress looked like a total idiot, sitting there impaled on his hand like some grotesque ventriloquist's dummy with her makeup slithering off her face. Yes, that was probably it- girls could sense that sort of thing.

Mary Ann's technique was not bad for a girl who thought a cock was just a male bird and sex before marriage was a sin. She used the sole of her foot to caress his loveprod, pumping up and down, then she rubbed her big toe firmly over its large, bulbous head before pumping it again between two toes. It wasn't long before Gilligan felt his balls getting ready to unload, and to help bring himself off he went back to his water nymph fantasy and imagined her smooth, silky cheeks bulging outwards in her little face as he pushed his raging tumescence into her mouth and whacked off down her throat.


Gilligan's dick shot a hot wad of cum into the crotch of his jeans, and then another, and another, pumping it out like a squirt gun. His hips jerked and the bench he and Ginger were sitting on rocked backwards. Mary Ann gave him one last squeeze with her pretty little toes. He launched backwards, the bench tipped over, and both he and Ginger landed flat on their backs in the sand with a loud thud.

The Howells and the Professor stood up and peered over the table in astonishment to where they were both sprawled out. Gilligan was thankful that Ginger's gown was long enough to cover her hips and pussy. His fingers were somehow still inside it and he thought it lucky he hadn't busted his wrist! To all intents and purposes, it just looked as if Ginger had fallen on top of him. Which was good, because no-one could see the large wet patch forming on his now-softening crotch, either.

"What on earth?" cried Mr. Howell.

"A bug bit me!" Gilligan babbled. "A bug, a bug!"

"Gilligan, you idiot!" said Ginger, acting like she normally did.

"Sorry, Ginger," he said meekly, giving her an extra firm jab up the ass with his thumb just to let her know she wouldn't be getting away with it.

Mary Ann's sweet, innocent face peered over the table at last, smiling down at Gilligan like an angel. "That must have been quite a bug," she giggled, as perfectly innocent as the day she'd been born.

"Oh, it was, Mary Ann," Gilligan nodded. "It was. But don't worry. Next time I see that bug, it'll get what's cumming to it, I'll make sure of that!"

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