The Island

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He's trapped on an island of pleasure.
4.4k words
4
45.1k
16

Part 1 of the 2 part series

Updated 09/22/2022
Created 08/15/2005
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"Is he still alive?" she said.

"Of course he is stupid!" another woman responded.

"Let's roll him over." another woman exclaimed.

"What the hell will that do?" he heard another.

He tried to open his eyes to asses the situation, but when he did all he could make out were dark and light spots; then just darkness.

He awoke and threw himself forward gasping for air in an unfamiliar location. In front of him was a rock wall, to his right a boulder with some empty water bottles and a book spread eagle with the pages down. The cover said "Eva Thomas: The Bride in Disguise", it was red flames with a shadow that outlined a woman's face.

There was light coming in from above and another area in front of him off to the left. He heard water, loud water as if it were somewhere inside this place. He looked at what he was lying on; it was a layer of grass with some type of wood under it. He swung his legs to his left and started to stand when he felt incredibly dizzy. He reached out and stabilized himself on the bed, then took a few deep breaths and tried again to stand.

He realized he didn't have any shoes or socks on when his feet touched the sand. It felt cold and damp and squished between his toes. He lifted himself off the make shift bed and grabbed a nearby wall to help keep him from loosing a battle with gravity. He walked toward the light on his left, he knew now that he was in some kind of cave; but he didn't know why or how he had gotten here.

He stood in opening of the cave and looked into the deepest forest he had ever seen. There was a 20 foot clearing right in front of the cave entrance, at 25 feet you could be swallowed in a river of trees.

"Hey sleepyhead, you shouldn't be out of bed!" a woman called. "Let me at least let the doc know your up."

He looked to his left and saw a woman at the beginning of a path. She turned and started running back down before he could see what she looked like. He leaned up against the entrance and tried to recount what had happened and how he might have found himself here.

He remembered being in the air... and then it all came back.

"Mayday Mayday!!! This is Two Sierra we have lost both engines!!" He screamed into his radio.

"Jim! Jim! The radio is dead from that last strike!! We have to set down some place!" his co-pilot said.

"Where the fuck do you want me to set down Ray? The middle of the fuckin' ocean?" He screamed back.

"There's an island about 65 miles ahead, I've made this run before! We can make it if we can get close enough!" Ray shouted back.

He didn't have much of a choice the plane was falling apart and out of the sky. He took off his head set and grabbed the controls with both hands. Another flash of lightning, he heard a pop from behind him and everything started to go black.

"Jim! Jim! J..i.."

"Take it easy Captain!" a woman said. "With a bump on the head like that, you need to save your energy. We don't want you to slip into a coma." She said.

He looked towards the path to see a dark haired woman approaching him. She could have been in her late twenties, about 120 pounds, dressed in shorts and a tank top.

"Have a seat and let me look at that wound." She said.

He lowered himself to the ground with the help of the wall that had been supporting him. She came up and squatted down, pushed his head down and said "Well it's gonna be a nice bump for a while, but it looks like your going to be just fine.. Probably have one hell of a headache for a day or two."

"Who are you?" he said.

"Sorry, I forgot we haven't met yet. I'm Sally, Sally Len. I was one of the passengers on the flight that brought us to this wonderful island." She said.

"Aren't you a little young to be a doctor?" He said

"Well, your more than welcome to get a second opinion! I think the nearest clinic is about a thousand miles away though." She snapped.

"Sorry, I didn't mean anything by it. I just ..." He started.

"Don't worry about it. I would ask for a second opinion too. I'm really only a lab technician, I just know more about being a doctor than anyone else here." She said.

"How long have we been here?" He said.

"It's been about a week now. We didn't think you were going to wake up, I'm glad you did." Sally said with a smile.

"Me too. How many other survived?" Jim said.

"Oh, almost everyone. Out of the 30 people we are only down to 27. I'm sorry to say, but it was mostly the crew. Ray the Co-Pilot, Jen the stewardess, and Max a passenger. Ray and Jen did everything they could to get us here, Max died from injuries once we got here." Sally said grimly.

"Look, I have to get back down to the beach. When your ready, just follow this trail; it'll take you right to us. I also left you a walking stick inside, just in case you woke up and nobody was here if you did wake up. If you want to go back in and rest up that's fine too, you need it, but since I'm not really a doctor." She smiled and stood up.

"If you don't come down I'll come back and bring you some food in about an hour; just don't expect steak and lobster." Sally said as she started back down the path.

He leaned forward and put his face in his hands. "Pull yourself together man!" he thought. Ray had been his co-pilot on his last three jumps, and now he was dead. He kept trying to piece together what had happened, but it was no use; his mind was processing too much right now.

"Finally awake I see." A voice came from his right.

He pulled his hands from his face and looked toward the voice. She looked like she was eighteen, 5'3" with slightly curly dark hair, her tan skin covered by blue bikini top that was slightly too small for her and jeans that had been cutoff at the upper thigh and no shoes.

"Don't worry, I won't bite; unless you want me too." She giggled.

"I'm Rachel, you must be Jim." She said.

"Yeah" he responded softly.

"Hey, I know that this is a lot to wake up to. At least you missed the first couple of days. What a power struggle, one of the other passengers actually got his ear bitten off!" she said.

He turned his head toward the ground again, he just couldn't believe he had lost the plane; what could have happened?

"Relax!" she shouted. "I know it's going to take some time to adjust. That's why I'm here." She said.

"What are you on suicide watch?" he responed.

"Should someone be?" she said.

"Look, I'm not going to kill myself or anyone else! I just need some time to wrap my head around this!" he shouted.

"Hey don't get pissy with me mister! I'm just trying to be nice and make the best of the situation! Besides, I don't think you should wrap your head around anything after that nasty bump." She hissed back.

He was starting to get really angry now. "Who the hell does this girl think she is?" He thought. Then he started to smile, he had thought she was right about wrapping his head around anything, "guess I have already done that." He thought.

"I'm sorry. Your right, I think I should try to make it down to the beach and see what I can help with." He said.

"Actually I was going to help get some of your things and move you into your hut." She said.

"What hut?" he said.

"We have been building shelters, and bathrooms.. well showers and a toilet area since day three here. Your hut was the last one we built, mostly cause we didn't think you were going to make it." She smiled.

"Wha.." He laughed.

"Well lets get what we can and head down there." He said.

She reached out her hand and helped him up.

"Wow, you go to the gym?" she said.

"Not for the last week or so." He said with a smile.

She laughed and started walking into the cave. He started to follow her, and his eyes fell down to her ass. "I wonder if she knows half her ass is hanging out?" he thought.

"Wow nice bed. Let me guess, you woke up because of the huge rock that was sticking in your back. I guess a rock slab with grass is better than on the sand with the bugs though." She said with a smile.

"I guess, I don't think I would have minded either way considering." He replied.

She was laying over the rock they were using as a night stand by the makeshift bed gathering up the hard to reach items. When she went to stand back up, her top had gotten snagged on part of the rock and her blue bikini top fell to the ground as she fell backwards towards Jim. It took her a second to realize what had happened, and she started to cover her exposed breasts but realized she couldn't possible stand back up while covering herself.

"Are you ok?" Jim said as he rushed towards her.

"Just a little embarrassed, I guess I made your day huh?" She said trying relax.

"Oh I didn't see anything." He was lying to her as he started to lift her back up.

"Stop!" She shouted. "You shouldn't be doing too much. You could have a relapse or something and then where will we be?" She said as she threw her hands to the ground and started lifting herself up. "Besides, what's a little peep show?"

She turned towards him with her arms to her sides fully exposing herself to him.

He didn't know what to say, he just stared at her magnificent tan breasts.

"Do you like what you see?" She said coyly.

He couldn't respond, they were the most stunning set of tits he had ever seen. He pulled himself back up, and forced his eyes to her face. She walked over to him slowly, took his right hand and placed it on her chest. It was even more wonderful then he could have imagined, firm, round, with perky nipples that were hard as nails. She reached around to his back, pulled him close to her and started kissing him on the neck.

The bulge in his pants was pressing up against her. She lowered her hand to his ass and pulled his waist even closer. He reached around her and pressed her into him as their tongues massaged each other. With his other hand he slowly moved down her back to her firm ass and slid his hand under her shorts. She lifted her leg around him to give him better access.

"Jim, Jim, I need you!" She moaned as she broke away from the kiss and tilted her head to give him access to her neck.

He lowered his head down to her neck and softly kissed it down to her nipples. He started to go lower towards her navel, and she grabbed the sides of his head to guide him. He got to the buttons on her shorts and started to unbutton the top one.

"I want you to fuck my ass Jim!" She said as she pushed him away.

She turned towards the bed and let her shorts fall to the sandy floor. He wanted to burry his face in that firm, round, ass. The thought of stuffing his ever hardening member in brown eye made him almost cum in his pants. She spit into her hand leaned over the makeshift bed, reached around, spread her cheeks and wiped the saliva all over her asshole.

He stood back up, undid his pants, slid them off and walked right up behind her. She was holding her ass cheeks wide so he could see his wet target. His cock was warm against her asshole as he slowly started pushing it in her. He only had to push twice before he was halfway inside her.

"OH! Yeah!" She shouted.

He pushed in and out of her ass as she got up on her elbows and arched her back. The feeling was amazing, she had obviously done this before; but not enough that she didn't have a tight grip on his cock. He reached up and started to play with her nipples.

"Oh fuck my ass! Give it to me, pump your hot cum into my ass!" She moaned.

He felt his balls slamming into her, but there was something different. Something was smacking into him. He put his hand on her waist and reached for her pussy when her hand grabbed onto his and pulled it up to her other tit. He kept pumping his cock into her ass, he was getting close, he could feel the cum building; it was going to be a huge load he was going to dump into her ass. He took his hand off her tit and again went for her pussy.

"Oh! FUCK ME! Harder Jim, harder, pump me full of your cum!" She shouted not realizing he had removed his hand.

He reached under her waist and could feel where the pubic hairs started. He slid his hand lower and felt something far different than he was expecting; "she has a cock!" He screamed in his head as he pulled out of her.

"What the fuck!" He screamed.

Rachel pushed herself up and turned towards him. Her cock must have been nine inches and was fully erect.

"Don't stop baby. I want that hot cum in my ass." She said.

"Don't you think you should have told me about this big problem you have? I would never have done any of this if I would have known you were a guy!" He shouted.

"I'm not a guy, I am a transsexual. I am becoming the woman you see, I have never felt good in my body and since I have to live in it; it should suit me. Look I didn't mean to deceive you, but ever since I first saw you I knew I wanted you inside me. Look at me, I am a woman! You were attracted to me! You were fucking my ass and loving it a minute ago! Don't let this little thing fool you; I was on my way to finish the procedure when we took our little detour. If you would have met me three days from when we should have landed, you never would have known and you would have wanted me just as badly as you did while you were pumping my ass!" She responded.

"You should have told me. I would have made my own choice instead of being duped into fucking you!" He said.

"What now? We are trapped on an island for who knows how long, we have already gone this far. Tell me what you want, I still want you. I wouldn't have let you fuck me if I didn't, I'm not a slut." She said

He thought about it, she held the cards right now. Even if she didn't know it, she could let everyone know what he had done. She could ruin his life when they get back to civilization.

"If she is going to fuck you when you get rescued, you may as well finish what you started." He thought. He grabbed his hardening cock and started to rub it.

"All right baby, lay that cock on me!" Rachel said as she started to turn around again.

"Wait, now that I know your secret; lay on your back." He said.

She turned back to face him, lifted herself onto the makeshift bed and laid back. He walked up to her and lifted her legs into the air and placed them on his shoulders. He adjusted himself and slid backup up in her warm, tight asshole once more. He kept looking down at her cock as it stood up, smacking him in the stomach. He wanted touch it, but was afraid to.

"It's ok baby, you can touch it." She said as if she was reading his mind. "We're sharing our bodies, you can do anything you want; touch anything you want." She continued.

He ran his hand down her leg, across her waist to her rock hard cock. He ran his fingers up and down the shaft, it was smooth and he could feel the veins in it. As he continued pumping her ass, he ran his fingers up to the head of her cock. He felt all around the mushroom head, and then wrapped his hand around her shaft. He started stroking it up and down, it was an odd sensation for him; he had masturbated before, but now he was jacking off someone else.

"Oh yeah baby, that's it fuck my ass and stroke my cock." Rachel said.

As he realized that he was massaging a cock and fucking this girl in the ass, he could feel that big load of cum was building. He knew that this would be even bigger than he had originally thought, this was a whole new experience for him. He thrust into Rachel hard, again hard, and again even harder.

"That's it baby cum in my ass! Fill me with cum!" She moaned

This was it, he was going to cum in her. Once more he thrust hard into Rachel, then again even harder. This time he stayed in her, spewing fresh hot cum in her ass. He must have squirted eight or nine times in her ass before he started to pull back. He gave her one final thrust and one more shot of cum in her ass, then let her legs slide from his shoulders.

"That was GREAT baby! I can feel your cum in my ass, there is so much of it." She said as she clinched her muscles around his cock trying to drain more out of it.

He lifted himself up again and reached for Rachel's cock. He took it in his hand and started going up and down on it, without ever taking his eyes off of it. It was still rock hard, and he wanted to take it in his mouth. He pulled out of Rachel's ass, lowered his mouth down to her waiting cock and engulfed as far as he could. He could feel it at the back of his throat, moved up to the head and worked his tongue around it, then went back down until it touched the back of his throat again.

"Oh Yeah, suck that cock baby!" Rachel said

He continued to move his head up and down on her member, each time going farther back into his throat; until his nose touched her pubic hair. He had swallowed nine inches of cock, and wanted more. He lifted his mouth off her cock and started to suckle her balls, taking each one in his mouth and working his tongue around them. He lifted his head up and looked at her face and said,

"I want you to fuck me."

Rachel smiled, she had hoped this would happen. She had wanted to cum in him as much as she wanted him to cum in her.

"Gladly baby." She smiled and stood up.

He moved into position on the makeshift bed, lying on his elbows and spreading his legs. She touched his ass cheeks, they were smooth and hairless. She began working her hands towards the center and spread his cheeks.

"We are going to need something." She said.

He looked back to see her reach around to her own ass and empty some of his cum into her hand. It was warm and runny when she smeared it on his waiting asshole. She slid a finger slowly into him as he tried his best to relax his ass. She worked her finger in and out of his ass until his muscles relaxed enough that she could slid in and out with some ease. She then inserted another finger and worked it until he was used to it, then another finger. It only took a minute for him to get used to all three fingers in him, then she pulled them out and rubbed her own cock. She reached around once more, got even more of his cum on her hand and smeared it on her cock, then his ass.

She put the head of her cock to his waiting asshole and slowly pushed into him. He had never felt this, he was actually going to get fucked in the ass for the first time; and he loved the idea. Rachel pressed even farther until she was buried deep inside him, the she slowly pulled back. It was burning in him, he could feel every vein in her cock, he could feel himself opening up as she pushed back into him. With every motion, he would relax a little more, and his cock would get a little harder. Rachel was moving in and out of him easer now, and his cock was once again rock hard.

Rachel was pumping faster now, and Jim knew that she was going to cum inside him. Suddenly she slammed hard into him and almost split him open, then again, once more and she had stopped. He could feel her hot cum blasting into his ass, squirt after squirt her cock pulsated in his ass. She held onto his hips and pushed as hard as she could into him, spending every last drop of cum into him.

"Oh baby, you were so tight I couldn't control myself. Your ass felt so good around my cock." She sighed.

He just laid there enjoying the feeling of her cock in him. He could feel it getting softer and removing itself from him.

"Excuse me, is this a private party?" Another woman said.

Rachel and Jim both looked over towards the redhead standing by the entrance to the cave. She was 5'10", fiery red hair, and a light tan. She had one hand down her light green shorts and was obviously masturbating to the two of them fucking. She had already removed her top and her D sized breasts where being rubbed by her other hand.

"Come on in, let's get this party started!" Rachel exclaimed.

The redhead took no time getting over to them, laid back on the ground, and engulfed Jims cock in her mouth. Rachel pulled out of Jim, lowered herself and started licking her cum off his ass as it oozed out of him. The redhead reached down and slide her shorts down, kicking them the rest of the way off so as not to interrupt sucking Jims cock.

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