Gilligan's Island Ch. 01

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
The tease
The tease
45 Followers

"I'm right with ya on that one," the Skipper said, "But how are we going to be able to tell, Professor?"

"I know…I know what to do," said Gilligan.

"Quiet, little buddy. I'm asking the Professor."

"But I know what to do!" Gilligan said again.

"What would you do, Gilligan?" Asked the Professor

"I'd take a picture of us now and a picture of everyone later and compare the photos and we'll be able to tell if anyone got skinnier or fatter. We can save one photo because we know the Skipper won't lose any weight."

"Ha-ha, very funny, Gilligan, but that's the dumbest thing I ever heard," the Skipper said. "We don't even have a camera!"

"Brilliant idea, Gilligan! We ought to elect you king of the island and all bow down to our new ruler!" Mr. Howell chimed in. He was still a little upset with Gilligan. He still had a lingering feeling that if it were not for Gilligan screw-ups, they wouldn't have been stranded here in the first place.

"But he is on the right track," said the Professor, "What we need to do is get a medical photo, or history, on everyone here. This will give us something to compare ourselves to later on."

"Great idea, Professor!" squealed Ginger. "I can be a lot of help, too! I have a nursing outfit that I used to wear while I was doing an old burlesque revival show Off-Off-Broadway. I look great in that nurse's outfit, too. It's very sexy and revealing!" She was beaming and obviously feeling better and was eager to help.

"Oh, and I have my nurse outfit too," cried Mrs. Howell, "I used to give comfort to the boys back in the Great War as part of the Beverly Hills USO. I was always the most popular nurse they had. The boys all used to request me for their sponge bath. Even the ones who could take showers asked for my help. They all loved me so much!"

"Always the caring soul, lovey," Mr. Howell said.

Since they had gotten on the island, Mrs. Howell had become insatiable. Every morning he awoke with his stiff cock buried all the way down her throat. Before he could get fully awake, she would climb on top of him and ride him. He was hoping he could keep up with her but she was always hinting and wanting more.

Everyone was shaking their heads and agreeing with the Professor's idea. It seemed a reasonable request. The Professor was thrilled it was so easy after his initial hesitation.

"Good we'll start first thing this morning. Who wants to go first?"

Six hands shot up and Gilligan even did a little "pick-me dance" but the Professor was looking squarely at only one person.

He never took his eyes of her as he said, "Good, Mary Ann will go first then! Thanks for being my first volunteer, Mary Ann, I'll try to be gentle!"

"I'll get dressed and be right over!" Ginger and Mrs. Howell cried in unison.

Oh, shit they'll ruin everything! Thought the Professor.

Acting quickly he said, "I need you both to do me a favor first...um...we're...we're going to need boiling water! Why don't you two gather up the water, first, and get it boiling. Then, I can start on the preliminary exam of Mary Ann."

"Okay, Professor" said Ginger and Mrs. Howell.

"I'll help you get the water, Ginger, and that will leave Mrs. Howell to help the Professor with Mary Ann," the Skipper said, trying to be helpful. He liked the idea of getting Ginger alone. He thought of her like a movie queen. She was larger than life in his eyes. He didn't think for one moment she would lean over the edge of the ledge and expose her ass like Mary Ann had.

She was too worldly not to realize the situation immediately. His thoughts were interrupted and his dick immediately started to harden when he heard.

"Why, aren't you the big, strong, hard...working one?" purred Ginger in her sexiest voice as she moved closer to the Skipper. "We just might have to start a reward program for you and all the help you've given me!" she went on in a sultry voice.

She teased the Skipper by letting her thigh brush up against the front of his pants. She could see her teasing was having the desired effect by the bulge building in the front of his pants. She decided to play some more.

"There are, after all, many, many, ways a big strong man like you can cum in handy. I bet you can think of all kinds of handy things you could do to, uh, I mean with me, eh, Skipper?" She said the last part as she was stroking his arm, giving him a great view down her low-cut evening dress and pressing her thigh into his stirring member. He blushed and thought she was just teasing him, doing some part sexy part out of a movie or something.

The Professor was frantic and had to think quickly about what to do with Mrs. Howell.

"Uh, Mrs. Howell, I don't need your help right away. I think it would be best for you to take Gilligan and Mr. Howell to the forest to collect whatever tapioca root you can find. We will need it to make a flu shot to prevent tropical fever." It was a barefaced lie but it was all he could come up with under short notice.

Mrs. Howell said, "How splendid, a tapioca hunt! What does one wear to a tapioca hunt?" She asked no one in particular. She was actually thinking of what to wear to entice Gilligan. She loved to teach young shy boys how to use their cocks and the fine arts of pleasuring a woman.

The real reason she was so popular at the USO is she could suck cock better than anyone alive! Her proudest achievement was that she had made every man she had ever sucked cum before the fourth stroke of her mouth on his dick.

That's how she landed Mr. Howell in the first place. One fantastic earth shattering blowjob and he gave her everything she could ever want. She missed the things he had given her: her gardener with his oral abilities, the grocery boy she had taught to slam her in the ass, and the paper boy's gigantic member. She would also miss the lesbian exchange student living in their beach house! Such gifts!

She was trying to get all of her needs satisfied by Mr. Howell but he was running out of steam. Gilligan could prove the entertainment she so desperately needed. Now what does one wear to entice a galley boy? She contemplated as she ran to change.

Ginger said, "Let me change out of this long dress, first, Skipper, and then we'll go get water.

You do know where to get water don't you, Skipper?"

"You betcha," the Skipper replied. It dawned on the Professor that Ginger, because of her recent illness, had not been to get water. The Skipper was grinning from ear to ear like a schoolboy. He'll probably spill the bucket a dozen times! The Professor thought.

With everyone busy, the Professor had averted a disaster and would have Mary Ann alone for hours. His dick was already at full mast thinking about all the places on Mary Ann that needed examining.

Mary Ann changed and decided to wear some revealing clothes. She was feeling funny about the Professor. She had never thought about having sex and, now, that was all she could think about.

She knew she should wait to have sex until she was married, but now she was actually hoping the Professor would be her first. It made her tingle to be dressing nastily for him.

* * *

A short while later Mary Ann entered the Professor's hut. She had chosen a short midriff top with the top two buttons open and an old pair of tight cotton shorts. The shorts were red with thin white vertical stripes on them. They looked extremely sexy on her. She figured if the Professor liked looking and stroking her ass so much, she would give him what he wanted.

When she passed by the Professor to sit on the makeshift table, he could see the white lines pointing toward the crack of her ass, half of which was exposed below the curve of her shorts.

"Outstanding," he muttered as she hopped up on the table, "Let's get started."

She looked at the row of makeshift instruments he had spent the night fashioning and suddenly her demeanor change as her eyes fell on a hypodermic needle.

"Please don't give me a shot, Professor, please! I'm so scared of shots." Her face grew all concerned and she was starting to tremble. "I just hate the thought of a needle. Please tell me I don't need a shot!" she said with frightened, pleading eyes.

He moved forward and hugged her. He put both of his arms around her, pressing her breasts into his chest, and held her tight. She trembled. She was sitting too far back on the table for him to press his erection into her crotch but he still tried to pull her forward without being too obvious.

"It's okay Mary Ann," he said as he rocked her gently, "If you do exactly as I say, I don't think I'll have to use a needle at all."

She became visibly relieved and stopped shaking and started to hug him back.

He stepped back and asked, "You okay?"

She shook her head yes.

"Okay. Let's start the exam. Everything will be just fine, Mary Ann. I promise. Just think of me as your doctor," He paused and with added authority said, "Now, take off your shirt and bra so we can get started."

She blushed and instinctively shielded her breasts by crossing her arms over them. She had not even considered that she would have to get naked for any reason.

"I don't know if I can," She murmured starting to have second thoughts.

"Nonsense, this is a medical exam, Mary Ann and I'm as good as your doctor. You're going to have to take all your clothes off to be examined by me."

"I know it's hard, but you have to. It's for your own good, in case you get sick later." By this time, he was holding her chin up and she was nodding slightly.

"Will you turn around?" she asked.

"No, I won't, Mary Ann. Look if you fall and hurt your chest or sprain your leg, say, up here." He placed his hand just above the top of her pussy. "Who's going to patch you up then? Eh?" He pressed a little harder and moved his hand a little lower.

"Me, that's whom. So enough shyness! Take off that blouse and bra so we can get started," he knew he had to overcome her protests to get her to do as he wanted. He stood back and waited silently.

She slowly unbuttoned her blouse and he could see her hands were trembling. She finished unbuttoning her blouse and removed it. She unclasped her bra and let it slide off her breasts.

He smiled, happy with himself, as she crossed her arms over her breasts and looked away. Here she was naked from the waist up, alone with the man she wanted to take her virginity! She was a little embarrassed.

The Professor didn't comment on this touch of modesty. It was, after all, really turning him on that she was acting so shy and demure. He pressed closer and brought his makeshift stethoscope to his ears. He made the stethoscope out of vines and bamboo last night. It looked real but was totally useless for listening to her heart.

"I'm going to listen to your breathing Mary Ann. Breathe deep and release it when I tell you."

He placed the stethoscope on her back and told her to take a deep breath and let it out.

He then moved the instrument around and repeated the scenarios a few times. He felt her relaxing and getting comfortable being naked with him.

"Drop your arms," he commanded and she did so. Now he knew why she was covering up. She had the longest nipples he had ever seen. They stood out proud and long and were as big at the end, not tapered at all.

WOW! MAGNIFICENT TITS! His mind screamed.

He decided he had to get his hands on those tits right now! He kept his left hand on her shoulder and with his right hand moved the stethoscope to her right breast. He held the metal part of the stethoscope in the V of his fingers so the tips of his fingers were free. He let his fingers stretch out until they came into contact with her nipple.

He lodged her nipple between two fingers while he moved to different examination points. He gently squeezed the nipple between his fingers and was amazed at its size and thickness as he pretending to carry on the exam.

"Ohhh!" she cried, as her nipples had always been extremely sensitive. She jumped as the Professor applied more pressure to her breast and gentle rolled her nipple between his fingers.

"Breathe deeply." He said and, as she inhaled, he cupped her entire expanding breast in his hand.

"Hold it in," he said.

He couldn't believe her nipple grew even larger and stuck out a good half inch past his fingers! He repeat the same examination to her other nipple and when he was done they were both rock hard and pointing straight at him.

He finally put down the stethoscope and said; "Okay, that's done. Now we need to check your breasts for lumps. This is an early detection procedure for breast cancer," he added. He placed one hand on each breast and began to knead them gently in a circular pattern.

"This is how you check for lumps." He was squeezing her breasts together and pinching them. The Professor then moved to another area and began pinching it. He was taking his time and squeezing her breasts ever so slowly!

She had her eyes closed and her breathing was becoming rather ragged as he continued to stroke her breast. He was now gently twisting her nipples between his thumb and forefinger with just the slightest pressure. She felt dizzy and disoriented but loved how he was making her feel.

Part of her wanted him to stop and part of her just wanted to let it happen. She decided she should just be quiet and try to enjoy the "examination". It was better than a getting a shot, after all!

The Professor, tired of just rubbing her breasts, decided to move on. He took out a flashlight and shined it into both ears and then down her throat.

"You have your tonsils still?"

"Yep. I never had them out," Mary Ann replied.

She felt funny. She wished the Professor hadn't stopped checking her breast. Her pussy was on fire. She crossed and uncrossed her legs quickly trying to press some part of her thigh against her inflamed pussy. She want to rub her clit and cum like last night.

It was just a medical exam, she told herself, think about something else and you can go make yourself cum when he's finished.

The Professor left her and went to another table, which was full of books. He grabbed a big, professional-looking book. It was actually a world atlas but it had a big and important looking cover and gold-lined pages. He flipped through the pages pretending to look something up.

"Tonsils, tonsils, lets see…throat problems…ptomaine poisoning…ahh… here it is, tonsillitis."

He frowned and looked at her. "You don't like shots, do you?"

"No. No shots!" she pleaded.

"Well, here, it recommends a shot of potassium-sulfated-chloride to prevent infection of the tonsils in an adult female. It is, I'm afraid, a very large and painful injection, Mary Ann."

"No, no shots!" She started to tremble again as her face turned to fear. " Please, no shots, Professor."

"I am afraid that that's the remedy," he lied. He flipped a page and pretended to find something, "Wait there's a homeopathic remedy here on the back of this page. Let me read what it says."

"Anything, oh please, I'll do anything to avoid a shot," Mary Ann said.

This was too easy. He was thinking this stuff up on the spot too! He was proud of himself as he stated, "It says here that native tribes in tropical rain forests use "Mans-seed" on a daily basis to cleanse the tonsils and prevent infection. Lab studies proved it effective in 1953."

He was so proud of himself when she brightened immediately and said, "No shots?"

"No shots!" he replied.

She threw her arms around him and rocked forward in her relief practically throwing him off balance in her excitement. His cock made contact with the front of her cunt. He ground away while her hard bare nipples poked through his shirt and pressed into his chest.

"Professor?" She asked.

"Yes."

"What's in "Mans-Seed" and what do we have to do to get it?" she was pretty sure what it was but wanted to make sure.

He almost came right there. Lord, this child is so naive! He thought. What a sweet innocence this woman contained.

"Well, Mans-seed comes out of a man's penis. Getting "Mans-Seed" to come out of a penis can be very difficult, Mary Ann. I'm not sure you can do it. It takes a special talent. You will have to take my cock in your mouth and suck it with all your might, just right, for a long time. Your jaws will probably get sore before you will get any sperm, which is what "Mans-Seed" is."

"Oh please, Professor, please. I'll do exactly what you tell me to do! I'll try really hard and do whatever you tell me!"

"Are you sure you'll do everything exactly as I tell you?"

She shook her head eagerly and he smiled. He laid her down on the table and she curled into the fetal position on her side with her face at cock level. He unzipped his fly and took out his cock, stroking it as he approached her mouth.

She couldn't take her eyes off his cock! It was so small compared to the horse but she wanted to reach out and feel it. She could feel juices flowing out of her pussy as he approached her. She remained transfixed on his hand stroking his throbbing member.

W-w-what are you gong to do with it?" she asked finally.

"Well, Mary Ann, sperm comes out the end of a man's dick when he gets over-stimulated. What you need to do is suck my cock until my sperm heats up to sprays down your throat? That will coat your tonsils and prevent any chance of infection, understand? You will have to listen to my instructions and suck hard or it won't work."

She shook her head yes that she understood and opened her mouth wide and closed her eyes. He moved forward and slowly eased his cock into her mouth about an inch and then pulled it out. He slowly increased the depth and the speed of his motion. She lay motionless as his cock moved slowly in and out of her mouth a few more times.

"Wrap your lips around your teeth and lick the shaft, right here, a few times like it was a lollipop." He pointed to his favorite location.

She licked the underside of his cock and, like a pro, zoomed in on his most sensitive spot. Making slurping and sucking sounds as she licked along his shaft.

"That's it! Right there!" he cried as her tongue circled the head of his shaft. "Lick it hard right there! Good!" he said as her tongue kept up its circular motion around his cock.

She eagerly did it all. She was concentrating hard at her task of trying to make him cum. She knew if she failed she would get a big painful shot. He placed her right hand on the base of his cock and started stroking his balls with it.

"Hold the base of my cock with one hand and stroke my balls with the other." He then took her pigtails in his hand and started using them to aid in fucking her mouth. He pressed deeper into her throat but met resistance. He knew she was close to a gag reflex. He felt he was getting close to cumming and wanted to prolong it. He decided it was time for her lesson in deep throating.

"Ummmp, ummmp, ummmp," was all she could manage and he thrust deeper and harder trying to get his whole cock down her throat. He was now pumping about half of his cock in her mouth.

He was getting even more excited thinking that she would do anything he instructed. It was time to turn this virgin into a full-fledged cocksucker. He pulled his cock out of her mouth to get her attention.

"That's not deep enough in your mouth, Mary Ann. Now, I'm going to have push my cock deep in your mouth, all the way in, to cum. You might be tempted to gag but you have to overcome that and let it go all the way down your throat. When my cock is all the way in, start rubbing my balls hard, okay? This will get my sperm hot enough to come out the end of my dick. Otherwise...."

She shook her head yes but wasn't sure she could do it. She had to try! Relax and just have fun with it! She told herself and that calmed her down.

The tease
The tease
45 Followers