Gilligan's Island

I would like to thank GeekGirlie for doing a great job of editing this story. She made the text fit the voices we all have in our head for these characters.

Chapter 1: Shipwrecked

"Better get a move on, little buddy. We need to finish the roof on the hut before dark. I don't like the looks of the storm clouds," the Skipper said, staring off into the distance with a furrowed brow. "Gilligan, get some more palm fronds and hurry!" the Skipper waited and there was no response. The Skipper grabbed his hat off his head and looked around for Gilligan. He wasn't surprised by what he saw. Gilligan had wandered off to stand behind Mary Ann again.

Mary Ann was stranding on the third rung of a ladder and the roof was at her waist. She was bent over and stretched out across the roof tying palm fronds to the top. She had one leg stuck out to the side to keep her balanced. Today, she was wearing a small pair of tight red shorts that seemed to be painted on.

The shorts rode up into the tight crack of her ass as she reached forward and the Skipper could clearly see her shorts were no longer covering either side of her perfect little mound. He could see the outline of her pussy lips framed in her pink underwear that strained to cover her. Gilligan had wandered over and put his nose a few inches from her crotch, drawn to her again like a moth to a flame.

The Skipper had to admit he had had more than one nasty thought about Mary Ann. Thoughts about how he would love to fuck her and take her virginity; turn her into a nasty cock-sucking whore who would submit to his every wish. He was starting to get an erection just thinking about it.

He shook himself out of it. Time was of the essence!

"Gilligan," the Skipper called.

Again, the Skipper got no response.

"GILLIGAN!" he shouted, wringing his hat in his hand. Gilligan turned his head. "Gilligan, hmmp! Quit fooling around and get over here. NOW!"

"Right away, Skipper." Gilligan said and turned to run to the Skipper. The only problem is he had one foot under the ladder. When he turned, he pulled the ladder out from Mary Ann and tripped and fell down. She fell forward and ended up bent over the roof beam. She started kicking her feet, trying to free herself.

Inside the hut, as Mary Ann hung above them, the Professor and Mr. Howell were getting an eyeful of jiggling tits by looking up her blouse.

"Professor, help me. I'm stuck. I can't move," Mary Ann said looking him straight in the eye. She had a look of complete panic.

"Don't worry, Mary Ann. I'll come around and get you down. Just stay there," the Professor said.

"We're on our way. We will rescue you!" Mr. Howell added as they raced out the door.

Gilligan and the Skipper arrived at Mary Ann the same time as the Professor and Mr. Howell. They all stood for a moment gazing up at that round, perfect ass with the cheeks hanging out of the bottom of her shorts.

"Stay still, Mary Ann. We'll get you down," the Professor said, "Gilligan, you take one leg and, Skipper, you take the other. Mr. Howell, you get underneath her and I'll get her from behind."

They took their positions. The Skipper and Gilligan each grabbed a leg and pulled them apart. Mr. Howell placed his hands on her stomach and the Professor grabbed her by the inside of both thighs.

"Okay, when I count to three, pull her down," the Professor ordered, "One…Two…"

He never got to three. Gilligan pulled earlier and set off a whole chain of events. Mary Ann slid off the truss and Mr. Howell's hands slip up her blouse and found her breast.

The Professor let his hands slide up to cup her ass. As she came off the roof, she fell back on the Professor and knocked him down. Mr. Howell refusing to let go of her breast fell on top of both of them. The Skipper was pulled on top of all three of them.

Mary Ann was sandwiched between the Professor and Mr. Howell. She could feel the Professor's cock hardening in the crack of her ass and Mr. Howell was still fondling her breast. It seemed like an eternity until they all got up.

* * *

The Professor lay on the bunk in his new hut stroking his throbbing hard-on while thinking of Mary Ann. She seemed completely unaware of her ability to entice men. Was it an act or was she really that naive? The Professor new it didn't matter; he knew he had to have her either way.

She was driving him nuts and consuming all his energy.

Her perky little attitude matched her perky little breasts!

He thought as he started stroking faster. That ass was really driving him insane. The Professor had managed to have one great encounter with that tight little ass of Mary Ann's. How to have another was consuming his every thought. He started to think about yesterday.

Mary Ann had come bouncing across the camp looking sweet and innocent.

She asked him, "Professor, would you help me get water from the stream?"

"Well, of course I'll help, Mary Ann," he replied, " This is a rudimentary task that will take some planning. We need to round up some gourds and buckets...and maybe get the Skipper and Gilligan to help..."

"Oh, come on, Professor, we can do it. Just you and me!" Mary Ann said encouragingly, with a wide-eyed innocence that froze the Professor. He decided to take the opportunity to get Mary Ann alone.

"Okay, Mary Ann. You are right. We can do it alone. You lead the way," The Professor made a sweeping gesture toward the path to the stream, waited for her, and fell in behind. He couldn't take his eyes off her little ass as she went joyfully bouncing up the path.

At one point, she had to climb over some rocks.

"Can you help me up, Professor? Then maybe I can help you get up!"

The Professor gave her a " hand up" by placing it squarely on her butt with his finger pressed into the crack of her ass.

"OOOOOOHHHHHHH!" she cried as his finger grazed the lips of her pussy. "That tiicc-klees! He-he!"

"OOPS, sorry, Mary Ann. My hand must have slipped when I was lifting you by your leg...." the Professor let his statement trail away.

That's okay, Professor. Here, let me get you up," she said and reached down to pull him up.

Later, while Mary Ann was well above him on the path, she turned around and could see the Professor was looking right up at her butt. She couldn't figure out why he was so interested. Why didn't he just get over it?

The way he had stroked her pussy had just sent shivers down her spine. She remembered that she had felt that feeling once before. It was the same feeling she had had at Aunt Erma's when her and Cousin John had seen two of the horses mating.

Watching that beautiful stud slamming his two-foot cock in and out of the mounted filly mesmerized her. She couldn't take her eyes off the stud as he kept pounding away! That huge cock was like a piston ramming in and out! It had gotten her tingly just as the Professor had.

Thinking about the horses had made her even more aroused and she shivered and wiggled her ass a little, putting on a nice little show for the Professor. When the horse finished, she noticed a huge erection in the front of her cousin's jeans. She always wished she had just reached out and touched it!

They finally came to the place were the Professor had rigged a bucket that could be lowered over a rock cliff to get water from below. The Professor stood back a couple of feet to watch the view unfold as Mary Ann slowly lowered the bucket by leaning over the rock ledge.

There were many other places where they could get water by simply scooping it from the stream. The Professor had chosen this place because the water was cascading over a small rock waterfall and aerated water was the safest and best. He never dreamed he would be watching the squirming ass of Mary Ann because of it. Because he had decided to get water here, she leaned against the rock ledge with her legs spread to maintain her balance. It was just dumb luck!

She concentrated entirely on letting the bucket down smoothly, hand over hand, while trying to hold it close to the cascading water so the bucket would fill quickly. She was straining on her tiptoes, bent over at the waist and stretching to reach over the ledge. She shifted her weight from foot to foot, giving the Professor a spectacular view of her twin butt checks poking out of the bottom of her shorts and her pussy squirming against the seam of her denim cutoffs.

About half of her cheeks were visible as her shorts rode up her ass and her pubic hairs stuck out on either side of her white panties! He could clearly make out the lines of her cunt as her pussy strained against the confines of the tiny piece of denim material now stretched too tight to hide any part of her beautiful pussy!

His nine-inch cock was standing at full attention. He was rock hard as he reached to shift it in his pants. The problem was he was so horny he couldn't let go and started stroking it through his pants as he watched Mary Ann put on a show.

GOD I HAVE TO FUCK HER!

His mind screamed as he pumped his cock faster.

"Can you give me a hand, Professor?" Mary Ann's question snapped him back to reality and he jumped forward.

She needed help because she had a full bucket of water and her arms were starting to get tired. Her shorts had ridden up into the crack of her ass causing a tingling sensation that knifed through her entire body as the fabric pressed hard into her clit.

She was shifting her butt from side to side, trying to relieve the strain on her pussy. This only caused her shorts to bunch up more and apply more pressure to her pussy lips. The added pressure caused by her squirming was setting her pussy on fire! She needed desperately to let go of the bucket and pull down her shorts but she didn't want to let go of the rope now that the bucket was full.

The Professor moved forward and then hesitated. He didn't quite know how to help. The opening was too small to get on either side of her and he scratched his head trying to figure out how to get hold of the rope.

Mary Ann sensed his hesitations and said, " Place your arms around me and grab the rope with both hands."

He placed his arms around her and reached for the rope. The first thing he felt were her breasts as he let his hands slide slowly over them. He grabbed for the rope to take up some of the weight.

As he did, he pulled on the rope. Mary Ann rocked back to get some of the pressure off her pussy and ended up jamming her tight ass into his awaiting erection. It was like a thousand bolts of lighting stuck him. He stiffened up and pressed forward with all his weight driving his cock into the folds of her ass cheeks. He was in heaven!

She jumped forward as soon as she felt her ass encounter his erection. It was huge and felt like a small stump pressed tightly against her ass cheeks. By instinct, she tried to move forward but there was nowhere to go. She ended up with his cock stuck firmly in between her ass cheeks and pressed firmly against the wall.

"Pull up quickly, Mary Ann, or we'll tip the bucket!" he said.

She stretched forward, raising her ass high in the air. This allowed the Professor to press his hard nine-inch dick directly along the slit of her pussy. Every time he pulled on the rope he rocked on his heels and slid his cock along her pussy lips. He started to dry hump her pussy mound in time with the swaying motion as they raised the bucket.

He moved his right hand inside her arm so his arm pressed firmly against her tit every time he took up the weight of the bucket. He could fell her nipple harden as it rubbed against his arm.

The Professor couldn't stand the pressure of her ass on his prick anymore. He was frantically humping his cock against her ass. He knew Mary Ann had to feel his hardness and must know what was going on, but she was either to shy to say anything or too naive to care. The thought of her being submissive turned him on even more and he was driving his cock against her as hard as he could.

He felt the pressure rise in his balls and he knew he was about to cum as he rocked his hips and slammed her ass hard. He thrust hard just as Mary Ann reached the handle of the bucket, hoisted it up, slid to the right, and spun away from him at the last possible moment before he would have shot his cum all over the inside of his pants.

"Oh no! Wait a minute!" the Professor mumbled forlornly, " I was so fucking close. AGHHHHH!"

His cock was throbbing and the pulse of his heart sounded like a freight train in his ears. His ass was still humping air because his mind was in denial.

"Are you okay Professor? You look a little flushed!" Mary Ann asked as she bent over with her back to him to pour the water from the bucket into the gourds.

The Professor's only consuming thought was to mount her ass and fuck her here and now. It felt like slow motion as he shuffled toward his target like a zombie in one of those horror movies. Just as he reached her and grabbed for her she turned around and placed the straps of two gourds over his outstretched hands.

"Here you are," she said as she spun on her heel and headed back toward camp.

The Professor got an idea. He didn't grasp the handles of the gourds and they slid off his arms, dropped to the ground, and spilled.

"Oh! Sorry, Mary Ann. I'm afraid we'll need to haul up more water. I am so clumsy sometimes!"

"That's fine Professor, the Skipper did the same thing when we were here and we had to do it twice too!"

She grabbed the bucket and took up her position at the rock ledge. He shimmied up behind her. His raging hard-on thanking him the whole way.

As she lowered the bucket he looked down to see the rope sitting by his foot. This gave him an idea! He stepped forward on the rope and shifted his weight at the same time so his cock pressed into Mary Ann's tight little ass. The bucket stopped moving down because he was standing on the rope.

"I think the rope is caught, Mary Ann. Give it a couple of quick tugs to see if you can dislodge it?"

She tugged twice and it didn't budge. She then started tugging rhythmically, causing her hips to shift from side to side. His cock was on one hell of a joy ride as she worked her firm ass across his cock again and again trying to free the bucket.

God, she's too good to be true!

The Professor thought of his new playmate. He could go on like this for days, but he knew that the fun had to end. He let his foot off the rope and with one more tug from Mary Ann the bucket "came loose." She bounced for joy.

"We did it, Professor!" She said.

Her bouncing had given the Professor an unexpected surprise. Jumping up had caused his cock to embed itself against the crack of her pussy lips. The continued bouncing of her ass on the end of his cock caused enormous pressure on the head. He felt it and he knew he was going to cum!

He pressed hard against her ass and felt the cum rising from his balls. He started cumming hard and exploded into his pants with each stroke against her ass. He shoved his cock as hard as possible wishing he was cumming in her cunt.

He actually lifted her off her feet for a moment in an attempt to enter her, as he pressed hard during the final load. He finished cumming and shifted his weight back a little bit, letting his dick ease out of the crevice of her ass.

They finished getting the water and headed back to camp. Good thing he had jerked off a couple hours before! He didn't have too big a stain on the front of his trousers.

* * *

Later that evening Mary Ann lay in bed. She was excited thinking about what happen at the stream. The Professor definitely had a "hard-on" like that horse and was excited by pressing it against her ass, she could tell by his heavy breathing against her neck.

It was so exciting when he was rubbing it fast and hard against her pussy! She started fantasizing about what might have happened if he had put that cock into her like that horse did the mare.

She wondered if the Professor would mount her and fuck her like that horse did. Her hand reached between her legs. She was wet. She started rubbing her pussy and it felt good.

What if he had ripped her pants down and taken her right there! She was attracted to him and loved the fact he was unable to control himself. She started rubbing her clit harder. She became flush and short of breath. She stroked her nipples with her left hand squeezing one nipple then the other.

She had no idea have sexy her nipples were. They stuck out a full two inches when hard and were as thick as a pencil eraser. She did however know the slightest contact with them made her dizzy with desire so she had always been careful to keep them tucked away in a soft bra.

Her right hand was busy lightly stroking her clit to match the movements of her left hand on her tits. She started to run a finger frantically along her slit as she thought about the Professor's hard dick pressed firmly against her ass.

This sent fire up and down her spine and she stroked faster and faster. Her hips rocked to the movement of her fingers and she kicked off the blanket. She thought about how the Professor's dick pulsed and throbbed when they lowered the bucket the second time.

Is it possible he came?

She wondered. She could still feel his dick throbbing as he pressed into her ass.

God, what if he actually came just by pressing against my ass!

The thought of him cumming sent her over the edge. Wave after wave of intense pleasure rolled over her body as she stroked herself to her first ever climax.

"Oh, oh-oh, oh-ooohhh-oooooooohhhhhhh yey. Yes unnngggg, yeeeeeeesssssssssssssssss! I want you so bad Professor. I want you to FUCK ME. I WANT YOU TO FUCK ME HARD!" she cried as she stroked her clit in circular motions riding her climax out to the end by bucking her hips hard against her fingers.

* * *

Gilligan came with Mary Ann, squirting his cum against the outside of the hut watching her bring herself to a shuttering climax. He had a great view of her wide-open pussy and tits in the moonlight when she kicked the covers off her body in a fit of passion.

The moonlight came though the opposing window and fell across her chest and legs. He chuckled to himself about his good fortune as he tied up his pants and stole one last look at that now angelic face in the moonlight. Mary Ann had retrieved the covers and pulled them up to her neck and was drifting off to sleep.

He had come to the hut hoping to catch a glimpse of one of the girls undressing but never expected such a magnificent show! From Mary Ann, too! He started to wonder if he could get to fuck her, even if she was calling out for the Professor. Little did he know he would get his wish soon, if he could just play dumb! Lucky for him he was a natural.

* * *

The Professor came up with a brilliant idea to get Mary Ann alone and naked. He sat in his hut alone and thought it through from every possible angle. He convinced himself it was perfect plan and drifted off to sleep.

* * *

The next morning as the group settled in eating the fruits and nuts they had gathered, the Professor decided to propose his idea. In the light of day, he wasn't as sure about his plans as he had been the night before but he new he would regret it if he didn't try it.

"Look, everybody," he started, "I know we all hope to get off the island soon but we also have to be practical. We may be here a very long time and need to start thinking about our long-term health."

"Ginger here has just gotten over being sick and our diets do not contain as much protein as I would like," he continued, "The lack of variety in our diet is also a concern. I feel we need a way to gauge how our health is doing over the long haul if we want to survive here on this island."