The Island: Meghan Ch. 01

"That's horrible! Have you ever tried to escape? Has anyone ever found a way off this island?"

"No, Anna, no one has ever left the island. Except the women who went to maintenance and were taken to the neighboring island where the native workers live. You don't want to go there."

"No doubt, those didn't look like the kind of men I want in my life."

Anna continued chatting with the maid but quickly came to the conclusion there was not going to be an option for leaving this place. At least not now. 7pm was approaching and she went back to the bedroom to get dressed for dinner. She took time to make herself look presentable to him, figuring that staying on his good side certainly could not hurt. Jason showed up a few minutes before seven and sat at the dinner table. He raised an eyebrow when Anna came into the room.

"You look spectacular, Anna. I think you are starting to adjust. That pleases me."

"I'm trying. I will do my best to make the best of things as you said."

Dinner was served by the maid along with some expensive red wine. Anna took advantage of the drinks and was feeling pretty buzzed by the time dinner was finished. Jason stood and walked over to Anna. He pulled her hair back and kissed the back of her neck. She reacted with a sigh of pleasure. The back of her neck was particularly sensitive and she loved it when a man would kiss her there. Jason helped her out of the chair and led her outdoors to look at the sunset. They walked down to the beach by his house and strolled beside the palm trees for almost an hour. He told her more about the island and all of the different amenities for the members that had been developed over the years. Anna asked questions too and became familiar about different jobs she may have as a host.

They finally came back to the house and were standing out by the pool when Jason moved in for a deep kiss. She responded eagerly and felt his hand on her ass. His strong touch felt so good and she started to get wet from his touch. He moved his hand around as he slipped his fingers inside of her panties. She moaned as he played with her clit. After a few minutes of additional foreplay, Jason moved them into his bedroom.

He placed her on the bed and laid on top of her. She could feel his hard cock against her and realized how much she wanted to be fucked. Jason pulled up her dress and moved down to her pussy, finding it soaked. His oral skills were much better than any rich and arrogant guy she had been with previously. He worked his way around her clit and pussy lips until she was arching her back. Aching for him to put his cock in her, she wriggled beneath the weight of his body. Jason pulled up between her legs and placed his massive cock head at the entrance to her pussy. Slowly he worked his way into her, watching to make sure she was not in pain. Her wet pussy gradually accommodated him as he pushed in farther and farther. She thought that this had to be the biggest cock she had ever had. Certainly the thickest. After a few minutes of slowly opening her up he fucked harder. Anna moaned loudly as her body responded by matching his rhythm.

"Fuck me Jason. Oh my god. You feel so good. Fuck me harder."

That prompted Jason to go deeper and harder. After a little longer he flipped her over into the doggy position and hammered home once again. Anna loved the doggy position and could feel her first orgasm getting close.

"Oh my god Jason, you're going to make me cum! Keep fucking me,, oh god."

Her orgasm was more powerful than any she could remember. The size and thickness of his cock completely filled her and her pussy could feel every inch of him. Both of them were sweating heavily and Jason pulled out to lay on his back. Anna knew what to do next. She climbed on top of him and rocked back and forth. He grabbed her tits and played with them while she was grinding on him. She knew this position was great for most guys and before long he was ready to explode. She could feel him tense up as he flooded her pussy with cum, which then dripped out around his cock. She climbed off him and lay next to him, kissing and cuddling up to him in the hope they would spend the night together. Jason drifted off and Anna lay beside him, exhausted from the day and the hot sex they just had. She was glistening with sweat and had cum still flowing out of her pussy. She thought of getting up to clean herself off, but thought the better of it. She wondered what would come next. Would she ever find a way off the island? Could she find a way to be with Jason? She soon drifted off to sleep.

Morning came and the sun was shining through the windows, accompanied by a warm breeze. Anna opened her eyes and took inventory of her surroundings. Jason was not there but she could hear the shower running. There was a new sundress waiting for her on the end of the bed along with a bra and panties. She got out of bed and walked into the bathroom to find Jason in the shower. Anna walked in and joined him by pulling herself up against him from behind.

"Well good morning," said Jason. "I was just about to wash up, care to help me?"

Anna grabbed the sponge and emptied the body wash bottle onto it. She rubbed it all over his back and around to his chest, then down to his crotch. She made sure to spend a lot of time on his cock and noticed it starting to grow in her hand.

"Mmmm now don't just tease me, be prepared to finish the job, Anna."

Desperate to have him in her mouth again she took his cock. She could feel him instantly start to grow in her mouth. After a couple of minutes, Jason pulled out and pulled her up onto her feet. He kissed her and fingered her cunt, getting her wet instantly. He then bent her over so her ass was sticking out toward him. He rubbed his cock along the outside to get it nice and slick before pushing it inside of her. Anna let out a moan and pushed back onto his cock. She wanted all of him and was getting used to taking his girth and length by now. Jason grabbed onto her hips and pounded away. Anna was in heaven and wanted more. They fucked for about 5 minutes before Jason pulled out and grabbed a bottle of lube from the shelf.

"Have you done anal before, Anna?"

"Once," she replied."But the guy was horrible and it hurt. He didn't use any lube."

"Well I'm going to reintroduce you now, and while it will be uncomfortable at first you will come to accept and enjoy it." He reached down and rubbed lube along her asshole, slowly inserting a finger and then two to get her opened up a bit. Anna responded to his working her ass with some quiet moans and whimpers. "Many of the members are going to want anal sex, Anna, so you might as well start with someone who knows what they are doing." He put a large amount of lube all over his cock and slowly pushed the head up against her tight opening. He pushed in slowly and could feel her tense. "Just relax, once I'm in the pain will get better. I want you to play with your clit as I'm working myself in to you."

Anna obeyed and rubbed her clit. There was pleasure along with the pain and after a little while Jason was well inside her ass. Anna was getting turned on even more as his probing cock completely filled her insides. She could feel an orgasm building, and while it felt incredible it was different from those she normally had.

"Oh my god Jason, I'm going to cum! It hurts but I'm so fucking horny and wet."

With that she did something totally unexpected. She squirted all down thighs as she came. Jason could sense her getting ready to cum and emptied his balls into her ass almost at the same time. They kissed passionately and took their time enjoying what had just happened. "I don't know what that was but it has never happened to me before. I felt like I peed all over my legs but it felt so much better than that."

"You just squirted Anna," said Jason "It sometimes happens with women who have an orgasm from anal sex. Most tell me that it is more intense than a clitoral orgasm."

"Well it was different for sure. I felt like I was totally out of control, but in a wonderful way."

"I'm glad you enjoyed Anna. It will be something that will evolve with you as you spend time with men in different situations. Getting to know your body is important."

They took their time getting ready for the day. Jason thought to himself how beautiful Anna was. There were plenty of beautiful women here on the island but something was different about this one. He thought to himself that he needed to make sure to have more time with her in the future. He liked her.

After a late breakfast the two traveled down to the residence building where Jason introduced Anna to the resident mother. Maris introduced herself to Anna and promised to help her get acquainted with the housing and work environment. Jason kissed Anna goodbye and left to attend to another project.

Anna was assigned a one bedroom furnished apartment with a small balcony that overlooked the ocean. It was small but comfortable. Her first job would be working the pool bar and within a few weeks she was fully incorporated into the host program. She was working and entertaining members on a regular basis. Escape from the island slowly faded from her mind and she was becoming used to her new life.

Until....