tagCelebrities & Fan FictionGood Times on Gilligan's Island

Good Times on Gilligan's Island


Thurston J. Howell III was even more unhappy than usual about being stranded on the uncharted island in the middle of the Pacific Ocean. Just that morning, he had heard the financial news on the radio in The Skipper's tent, and the information had started a chain of thought in his financially brilliant mind. In a few hours, he had concocted a scheme that would have netted him an additional umpteen million dollars. Unfortunately for Mr. Howell, he was unable to implement his idea, or even tell anybody about it, and that fact was what was making him even more unhappy than usual.

"It isn't fair," he groused. "I should be even richer than I am, and I would be, if I weren't stuck on this God-forsaken island."

Mrs. Howell, Lovey to her husband, but only to him, had somewhat mixed feelings about being on the island. She missed all the teas and other engagements that, as a social leader, she would have been hosting or attending, but her flower garden was thriving, and she was getting more and better and different fucking than she had ever gotten. There weren't very many young people around to give her opportunities to exercise her match-making skills, but there were no other busybodies around either, who would have competed with her in those endeavors. Furthermore, the match she had made of a young couple, Mary Ann and Gilligan, just that morning, had the potential to be one of her best. Ginger and The Professor, the other couple Mrs. Howell had fixed up, seemed to be doing quite well also, and she was proud of her accomplishments in that area. All in all, the island was really a marvelous place to be, despite what her husband said about it.

That day, at least, Gilligan and Mary Ann were almost ecstatic about being on the island. Mary Ann had always enjoyed the tropical evening breezes, swimming in the lagoon and everything else about the environment. Lately, she had started also enjoying the presence of Gilligan, the sweet little cutie. She was much too shy to mention that to anybody, until she told it, in the strictest confidence, to the motherly Mrs. Howell.

Gilligan liked the pleasant weather and laid back atmosphere but, mostly, he REALLY liked the beautiful, charming Mary Ann. After all, what young man wouldn't? His big problem was that he was too shy to tell her, or anybody else about it, except for Mrs. Howell, who was like a mother to him. She, of course, knew exactly what to do about both those pieces of information that had been told to her in absolute, cross-my-heart-and-hope-to-die confidence.

Right at that minute, those two lucky people were extremely happy she had chosen to break her solemn word. Mary Ann's red and white gingham blouse and pink bra were hanging from one bush and her cutoff denim jeans and white cotton panties were hanging from another. Completely naked, the beautiful farmer's daughter was lying on her back enjoying the view of Gilligan's bare shoulders and his white sailor's hat between her legs. He had removed his shirt, but his head was inside the hat, and he was avidly eating her pussy, which was vastly more fun for her than just looking at his hat, or shoulders, or the scenery or anything else. Mrs. Howell, busybody and inveterate matchmaker that she was, had passed the word on to either of them when she had the chance. After that, in the normal course of events, the two infatuated young people headed to a remote part of the island to demonstrate what they felt for each other.

Being unmarried, Mary Ann was, of course, a virgin, and she was determined to maintain that condition until her wedding night. That night would follow a church ceremony, which would be presided over by an ordained member of the clergy, and her father would give her away to the handsome, young bridegroom, who would also be a virgin. However, she knew of ways to maintain her innocence while still having fun sexually, and she was happily teaching them to Gilligan, who hadn't seemed very disappointed at the limitations she insisted on placing on him. Mary Ann was glad of that, because he seemed to be a very quick learner. Already, he was giving her a better time than her steady boyfriend back home ever had, although her advanced condition of horniness probably contributed to how much she relished what he was doing.

Most of Gilligan's sexual experiences had occurred, literally, under The Skipper. What he was learning from Mary Ann was about a zillion times better, and he was already hoping for frequent lessons in the future. Her pussy was the most beautiful thing he had ever seen, with its smooth, creamy white skin and its untrimmed sprinkling of dark brown pubic hair. A tight slit ran up the middle, and there appeared to be pretty, dark pink flower petals pushing their way through it. Her legs rested on his shoulders, while his arms were wrapped around her soft thighs, bringing his face inches from the view that held him in such rapture.

Lovingly, he placed his index fingers on the sides of the narrow opening, and gently pulled them apart. Inside the slit, Mary Ann was even more beautiful, with a pink lining that was shiny with her wetness. A cloud of incredible fragrance arose when he spread open the aperture, and he breathed deeply of it, finding it the most delightful aroma of his rather limited experience.

"Careful, Gilligan, Mary Ann admonished him. "Don't put your finger in there. You can put your tongue in, though."

He took her suggestion, but only the tip, and Gilligan was amazed that the flavor of her wetness was even more delectable than the scent. Eagerly, he started licking everywhere she was wet.

"Oooo, that feels wonderful. But don't be in so much of a hurry. Lick along the sides of the slit first."

So far, everything had been so much fun, and Mary Ann was so sweet and pretty that Gilligan did what she wanted, even though the place he had first licked felt and tasted better to his tongue than anything else ever had, even warm chocolate pudding. With broad, slow strokes, his tongue started caressing the place where Mary Ann had directed him. He was surprised at how good her soft pubic hair felt. Enjoying every second of what he was doing, Gilligan slowly licked all the way to the pleasant bulge just below Mary Ann's flat belly. Everything about her pussy was delightful, the looks, the aroma, the flavor and, especially, feeling that part of the beautiful young brunette's body against his tongue. He even loved the way her soft thighs felt, squeezing the sides of his face as her body squirmed under him. Being as fond of her as he was, he especially enjoyed the soft murmurs of happiness that his mouth was eliciting.

"Oooo, yeah, Gilligan! That feels really, really good! Now, do the other side! The same way!"

With great alacrity, he started moving his face to do as Mary Ann directed, but he had to stop when his nostrils detected a plethora of fresh juices that had seeped out of her. Greedily, he licked them from everywhere they had collected, until he had devoured them all. After savoring their deliciousness, his tongue caressed her other outer lip the same way, stopping at the same place. When he brought his mouth back to where he had started, there was almost a flood of her fresh nectar. Happily, Gilligan sluiced it all up with his tongue and swallowed it, relishing the flavor even more.

After he was through feasting, he raised his head and gazed upon Mary Ann's beautiful pussy again. It was squirming even more actively under his face, and the aroma seemed to be even more delectable than it had been. From her movements and her sighing, he could tell she was enjoying herself immensely, and Gilligan was truly glad to be giving the sweet, young charmer so much fun. Besides what he was doing for Mary Ann, he reveled in the wonderful new experience that he was having, and he resolved to do more of it, as often as he could, and to do it even better, resuming with the pink petals that were so inviting.

Waves of pleasure washed over Mary Ann's sexy young body from what the first mate of the Minnow was doing with his tongue. Her body writhed on the soft, warm grass that formed their love nest, and she moaned blissfully. "Oh! Oh, Gilligan, that feels so good. Keep licking me there," she urged him.

He needed no urging. His tongue had never tasted such a delightful treat, nor had his nose ever smelled anything as delectable as the pussy of the young woman lying on her back. The spongy texture of the petals was like nothing he had ever felt. Once again, he briefly raised his head to gaze on her lovely body, and was surprised at how frenetically she was moving, and how her head was rolling from side to side. Her delightful breasts, in particular, attracted his attention with the way they swayed so erotically from side to side. Mary Ann's eyes were closed too and, from the appearance of her face, she seemed to be having almost as much fun as he was. She had moaned, but didn't appear to be in pain, since she kept telling him to keep licking her. It had already been such a wonderful adventure that he had no desire to do anything but that.

Gently and carefully, as if fearing she might be fragile, Gilligan licked the petals on the other side of Mary Ann's pussy. Their flavor was just as heavenly as the first ones had been, and they felt just as delightful to his tongue. Wonderful as it was to him, she seemed to be enjoying it even more. He recognized her moans as being of bliss, and wanted to do all he could to produce more of them.

"I wonder," he asked himself. "Would the place where I started feel and taste as great now as it did a few minutes ago?" It was a silly question, because he would be unable to answer it until he actually went back to lick Mary Ann there.

Once again Gilligan spread her slit open, reveling anew in the incredible scent that arose. Wanting to be careful not to put his finger where she didn't want it, he leaned in and started licking the narrow pink opening. "It's even better," he told himself, and licked upward to the end. There he found something surprising, a soft, pink pearl nestled between the petal-like folds of skin. Gilligan licked there, and found the sensation of the pink pearl against his tongue to be the best he had felt that day.

It was the best for Mary Ann too. "Yes! Yes!" she cried joyously. "Lick my clit! Suck my clit!"

While Mary Ann begged him to lick and suck the pink pearl, she was thrusting her pussy up against his face. That felt wonderful to Gilligan too, so he enveloped the little cutie in his mouth and started sucking. His tongue just naturally started licking the sides and top, really liking the way it felt.

"Oh! Oh!" Mary Ann cried, liking it even more than he did. "Oh, God! I'm cumming!"

Gilligan was wondering what she meant, because she hadn't gone anywhere, so how could she be coming, when Mary Ann's hands went to the back of his head, pressing his face against the delectable place he was licking. Her legs, which he had been thinking of as soft, suddenly developed muscles of steel as Mary Ann clamped them around the sides of his head. She bounced up and down with her legs swinging from side to side carrying Gilligan's head between them. He enjoyed the ride, and kept his arms wrapped snugly around her thighs and continued sucking the pink pearl and caressing it with his tongue.

Her ass had been churning up the grass for the last few minutes, when Mary Ann's muscles seemed to all clench simultaneously, and she gave out with a loud and joyful cry. After that, she relaxed completely, almost seeming to melt into the ground. Gilligan raised his head and smelled a great quantity of the fresh juices that had been so delicious, and started licking them off the lovely young woman who had produced them. She lay quietly and let him devour them all and, when he had finished, he again raised his head from her nakedness and smiled at Mary Ann's beautiful, happy face. .

She smiled back. "Gilligan, that was just wonderful. You did that better than anybody else ever has. Now, you lie on your back here, and I'll do the same for you."

Gilligan wasn't sure what she meant by that, but he did lie down next to her. Sometimes, after The Skipper was through fucking him, he would go to his bunk and jack off, but he didn't know if she meant that or not. He became even more unsure when Mary Ann rose up to a sitting position and unzipped his dungarees. When she started to pull them and his underwear off, he raised his butt from the grass to help her, but he still wondered what Mary Ann had in mind, even when he was just as naked as she.

Mary Ann knew what she had in mind, and she smiled when she saw the cock that was sticking up in the air and waiting for her. It was big and hard, and just what she wanted. Although not very bright, besides being inexperienced, Gilligan could tell that something very, very nice was about to happen to him, although he couldn't have known just how nice it would be. The beautiful, naked young brunette got back onto her knees beside him, took his hard shaft in one hand and started licking the head. Before she went any further, she turned to compliment the owner of the cock she was about to start sucking.

"You sure have a nice tool here, Gilligan. How come you've been hiding it from the girls?" He was too flustered to answer, and that was okay with Mary Ann. She had much better things to do with her mouth than chatting.

The first of those things was licking, all over the head and under the ridge and up and down on the shaft. After that tongue exercise, she didn't change her mind in the least about conversation, preferring instead to open her mouth wide and slowly engulf Gilligan's entire hard cock. Mary Ann reveled in the way the thick shaft forced her lips apart and filled her mouth until the tip pressed against the back of her throat. She raised her head again, eagerly licking the hard cylinder as she withdrew her mouth from around it. Taking his cock out of her mouth again, she turned, faced Gilligan again and blew him a kiss from her pretty red lips.

"Don't worry. I've found it now, and I know what to do with it," she told him, teasingly.

Seconds later, those same pretty red lips were wrapped around the young man's cock again, and she lowered them until they were being tickled by his curly pubic hair. The tip of his cock pushed against the back of her mouth again, but this time, Mary Ann opened her throat to let it slide down and in. She very much enjoyed deep-throating men, and did it for all her cute boyfriends, even those she had just met.

Although looking forward to being a wife and mother after being eventually rescued from the island, Mary Ann had some regrets about the changes that would take place in her sex life. She was concerned that, once she had been deflowered, her husband would just want her pussy, and she wouldn't get to suck him off. She was willing to make the sacrifice for her husband, but she was not very happy about it. Mary Ann hoped to partly make up, with Gilligan, for all the cocks she would some day no longer be able to enjoy taking into her mouth and down her throat and sucking off.

She was certainly enjoying herself with this one. Over and over, Mary Ann raised and lowered her face, pulling Gilligan's cock all the way into her mouth and down her throat. It felt wonderful, long and thick enough to give her a perfect mouthful, but not so big that she couldn't move it around with her tongue for maximum pleasure. On some strokes, she tilted her head slightly so the tip slid along the inside of her cheek until it reached the back of her mouth and slipped down her throat. Sometimes she positioned her head so the tip caressed the roof of her mouth and her palate before pleasuring her throat muscles. Whatever way she chose to fill her mouth with it, Mary Ann's tongue caressed all sides of the entire length of the shaft, reveling in the way the smooth skin was stretched so tightly around the hard cylinder.

For a long time, the happy young woman slowly sucked off Gilligan, until she felt his cock starting to throb in her mouth. From her experience, she knew that meant she was about to get a mouthful of his delicious semen. That payoff was her favorite part of giving a boyfriend a blow job, but she enjoyed the sucking itself so much that she always wanted to make it last as long as she could. Mary Ann continued sucking just as slowly, but no longer taking his cock down her throat. One time a new boyfriend had ejaculated early, and she had been deprived of enjoying the taste and texture of his cum, and she never wanted that to happen again. Her tongue continued to be just as active, but she made sure that she could quickly reposition it and catch Gilligan's semen when he shot it into her mouth.

From frequent masturbation, he knew he was close to cumming also, and Gilligan wondered if he should tell Mary Ann. Since he was still too shy and didn't quite know how to do that, he didn't, figuring she would find out for herself. He continued watching the young beauty as her head bobbed up and down, drawing in and releasing his cock and bringing his climax closer and closer.

Groaning out loud and thrusting his cock up into Mary Ann's mouth, Gilligan started cumming. The first gush of semen was quite prodigious, and covered her tongue, pleasing her taste buds and running off into the bottom of her mouth. She knew he wasn't done, and kept sucking. Her diligence was rewarded when Gilligan gave Mary Ann another gift, squirting more of the tasty fluid into her mouth exactly where she wanted it. This was just as delicious as the first had been, but she believed he wasn't through yet. Her guess was right. Continued sucking brought forth another, although smaller spurt of his cum. That was the last time, even though Mary Ann continued stroking up and down with her lips, hoping for more. Finally, she accepted that he was through, relished the flavor of what was in her mouth, and swirled it around, enjoying the texture also. After deriving as much pleasure as she could, she swallowed all of it, letting it slide down her throat, the way she loved to do.

Although Gilligan was through cumming Mary Ann knew she hadn't gotten all of his juices. Being careful not to let any drip off and be wasted, she slowly removed his cock from her mouth and held it in her fingers. Greedily, she licked everything off the head and under the ridge and from the sides of the still-hard cock. She still wasn't through. Placing her right thumb in front of his scrotum and her fingers on the top surface of his shaft, Mary Ann slowly drew that hand toward her mouth, squeezing out whatever was inside Gilligan's shaft. As his juices oozed out, she caught them on her tongue, and they tasted just as good as the cum that had squirted out. When Mary Ann was through draining everything, she licked Gilligan's cock again, wanting to get anything that might be left, and because it was so much fun for her tongue and lips.

Finally through sucking off Gilligan, she lay in the grass next to him. Neither of them had anything important to do, and they enjoyed the warm sun and the soft breeze on their naked bodies. It was very pleasant and, once they returned and rejoined the rest of the castaways, they would probably have to listen to Mr. Howell gripe about the island, and how much money he was losing by being stuck there.

"Besides," Mary Ann told herself. "After an hour or so, Gilligan might be ready to be sucked off again, and maybe I can get him to eat my pussy at the same time. All girls like a nice 69 with their boyfriends, don't they? Well, maybe not all of them, but I always have." She really loved being on the island, and the good times she was having there. Gilligan, if he thought about it all, would have agreed with her.

Ginger and The Professor were extremely happy about being on the island, and they had felt that way since Mrs. Howell had gotten them together. As always since that time, when the opportunity arose, they had sneaked off to a place The Professor had located in a grassy, sunny glen surrounded by shrubbery, which gave them privacy. He had actually found the spot while hunting butterflies for a biology project he was working on, and he remembered it when he and Ginger needed a place to demonstrate the feelings that had been aroused in them by Mrs. Howell's skillful matchmaking.

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