tagAnalAnal in Grand Cayman

Anal in Grand Cayman

byscubaman7777©

Samantha could not believe her luck, a business trip to Grand Cayman in the Cayman Islands. Her normal days as an accounting controller was boring to most people. Just bookkeeping, this meant playing with the numbers until they looked good on their profit and loss statement to the shareholders. But with the economy as it was, finding a safe place to put your money was a challenge at best as there was nothing certain (besides gold, but that could even fall), so the company decided to put some of their money stashed away in a Cayman Islands bank for a rainy day, and they sent Samantha to go down and do the paperwork and close the deal.

As transactions went, it was pretty straight forward and Samantha had things wrapped up in one day and she still had 2 more days scheduled to be there, all on the company's dime. She was staying at the Westin hotel on 7 mile beach, one of the nicest beaches in the Caribbean and a great resort to say the least. Having feeling satisfied she had done all she could for the deal, it was time to relax, and what better place to relax than by the pool, so off she went in her white bikini (with a red summer dress over it) to the pool which just so happens was right on the beach, the best of both worlds she thought.

Samantha had worked hard on her body, not so much to look good, but to reduce the stress from work. Sitting all day in front of a computer tweaking numbers did not do the body any good, so she worked out 4 days a week at the all-women's gym near her office. It was a mix of aerobics, palates, jazzercise and some weights mixed in to keep her sane and her 40 year old body in what she considered good shape. Her black hair was below her shoulders, her 36D cup breasts were firm she thought, and her legs were very tone from all the exercise she did, not to mention the abs she had from the countless crunches and her ass was tight and firm.

Even though she had a good body, men never seemed to work out for her. The longest relationship she had ever been in was 1 year, and that ended with them never speaking to each other again, just like most of her boyfriends. Her family was starting to think that she was really a lesbian, but besides her being able to appreciate the female body for its beauty, she like to make love to men, even with all the problems that come with them.

Strolling down the pool, she chose a lounge chair that was not around anyone and started settling in for a quiet late afternoon. There was still plenty of sun, so she removed her sundress which caught the attention of at least a few men who were hanging around the pool looking to see just that, women in bikinis. After applying some sun screen, she got out her Kindle and lay down to enjoy the latest romance novel she was reading. It was her guilty pleasure to read stories of romance mixed with some eroticism, but wondered if they ever actually happened to real people, then again she thought, not much would happen when you spent your life in an office all day, so no wonder she never had any erotic things happened to her. All the guys in her office were accounting nerds and the ones at the bars were just creeps.

She looked up from her reading to see a man in his 20's asking her something. As she left her fantasy world in her Kindle, she heard the man asking if she wanted something to drink. It was a waiter with a thick Jamaican accent. There had been a lot of Jamaicans here on Cayman as she learned from the bank she worked with that day and his accent was somewhat difficult to understand. "Something fruity" she asked him, and off he went to get her fruity drink.

This is the life she thought to herself, sun, water, warm weather, the only thing she had not liked so far was the traffic. There is only one main road on the West Side of Grand Cayman, and the traffic was horrible as it was the only road in town so to speak, but right now, the only traffic were the people who were waiting to get a drink, and she was looking forward to her fruity drink.

After 10 minutes, she looked up to see a man standing over her, but this was not the waiter with the Jamaican accent she had spoken with, this man was about 6 feet tall, with dirty blonde hair that looked to have been bleached by the sun, and a dark tan. Samantha sat up in her chair as the man handed her a red fruity drink. She said "Thank you", and the tan man said, "I had to tip the waiter $20 to let me bring you this drink, for that may I know your name"? Now she was surprised and did not know what to say, who was this guy, and why in the world would he pay $20 to deliver her a drink? "Samantha", she said. "Hello there Samantha, my name is Charles, it is a pleasure to meet you and I hope you enjoy this drink on me".

She thanked him for the drink and there was a moment of silence and awkwardness as he looked at her and she looked at him. Finally she said "Join me for a drink", why that came out of her mouth she had no idea, but she had said it so she figured she should at least have a drink with him. Charles sat down and immediately the waiter appeared with a martini for him. That was nicely played she thought to herself.

Over the next hour they talked about each other, she told him about her world of accounting and how she was on the island to finalize a deal with her company and a local bank. He told her about how he had owned a beauty supply company that made high end hair shampoo, conditioners and the like that catered to women. After years of building the company, he had sold it and was now enjoying the fruits of his labor as he called it. She was intrigued when he said he was not staying at the hotel, but on his 60 foot yacht that was moored just off shore (he had to explain that in Cayman, you cannot anchor as that would damage the reef, so you tied your boat up to moorings that were installed by the government to help protect the reefs).

After the 3rd drink, she was feeling a little tipsy, but was really enjoying talking with this handsome successful man who sailed around the Caribbean in his yacht, no one like that ever bought her a drink at home in her local bar. Charles asked her if she would like to go for a walk on the beach, as the sun was just beginning to dip into the trees and the sun was fading. Enjoying the conversation so much, she said "Yes, I would love to join you for a walk on the beach".

So she packed up her things and put her sundress back on and put her things in her bag and walked down to the water for a stroll on the beach with her handsome stranger. As they approached the water's edge, she could now see his yacht moored off shore. It did look like a big boat, but then again she thought to herself, she had never really been on a boat before, let alone a yacht. The air was warm, and the water was barely cool as they walked north towards the Turtle Farm that she had read about in the promotional material in her room at the hotel.

It seemed like miles they had walked, but had only been about ½ mile when he suggested they turn around and head back as it was getting darker and the sun was setting. Charles life story seemed like one of those in her Kindle books, wealthy, successful, but had the tragedy of being widowed and had never had the good fortune of having kids. With every word he said, she could not wait for him to keep telling her all about his life's accomplishments and failures.

Eventually they were back in front of the Westin hotel just as the sun was setting down below the water. They both stood there and silently watched the sun as it slowing melted into the ocean. Charles reached over and put his hand in hers, which made the moment that much better. Samantha felt like she was in one of her books as she had butterflies in her stomach and wondered what would happen next. Finally Charles asked her if she would like to join him on his yacht for a drink. "I don't think I can swim all the way out there she said", to which he just laughed and told her he had a dingy on the beach that would take them out to his yacht.

Normally Samantha would have said no, or maybe got his phone number, but she was on a Caribbean island and if she said goodbye to him right now, she thought she would never see him again, so she agreed to a cocktail on his yacht. They went off to his dingy and he dragged it back to the water, held her hand as she got in and he put the motor down, jumped in as he pushed it away from the beach. Starting up the engine, they sped through the water towards Charles's yacht.

They reached the yacht and he tied up dingy to the swim platform and helped her up and onto the back of the boat that he explained was called the transom. The area was large and surrounded along the edges with padded bench seating and a bar in the middle. The yacht moved more than she thought it would for its size, but quickly got used to the gently swaying back and forth moment. She sat down on the starboard (right) side of the boat on one of the benches to relieve her legs from trying to keep up with the yachts moving.

Charles went to the bar and retrieved two glasses and a bottle of champagne from the refrigerator under the bar. Popping the cork, she watched it shoot over the ocean and see it drop in the water as it made a splash, but then floated back up as a cork should do. It was then that she first noticed the moon that had risen in the night sky. There was no need for lights to be on the boat as the almost full moon illuminated everything and she easily took the glass of champagne that Charles handed her.

They continued their conversation under the moonlit night and the lights of Grand Cayman twinkling on shore and once again thought to herself that she was in one of her romance books. Just as she finished her second glass of champagne, he took their glassed and set them back on the bar where they had come from, sat next to her and without saying a words, kissed her gently on the lips which to her surprise, she kissed him back.

It was a fantasy world as they kissed for what seemed like hours, until their mouths actually started to get tired. Finally they stopped kissing and sat there a few moment not saying anything to each other. Then Charles took his hand and slid her sundress off one of her shoulders. She was not sure what to do, but did not want the night to end so she let him slide her sundress off her other shoulder. Her white bikini shone in the moonlight and was in contrast with her black shiny hair.

Charles reached behind neck and slowly pulled her the string on her biking as the spaghetti straps fell in front of her. Without that support, her breast became more free a fell ever so slightly, but her firm breasts did not need her bikini to keep them held up and stayed up on their own. He now moved his hand behind her back and again slowly pulled at the back of her bikini strings until the loop unfastened and he pulled his hand back holding her bikini top in his hand which he then tossed onto the bar.

Fantasy was meeting reality she thought to herself as she sat next to him topless in the tropical warm night air. In a quick moment she asked herself if she should grab her top and ask him to take her back to the beach, then his hands reached up and cupped her breasts ever so gently. Any thought of leaving quickly left as she felt his warm hands on her tits as he slowly massaged them. His fingers then slid to the end of her breasts to find her erect nipples which he then began to close his fingers around and squeeze them.

Her nipples were on fire as he squeezed softly, but then a little harder, just at the point she liked her nipples to be squeezed and she let out a long breath. Charles seemed to be enjoying this as well and did not rush the moment. He firmly held her nipples between his fingers for a few minutes until he felt her body shake, then released her nipples, and put his mouth on one of her nipples. He did not suck on her nipple (at least not at first), instead he flicked his tongue around it, then moved over to her other nipple to repeat his tongue twirling.

Samantha loved to have her breasts played with, and Charles was doing it just as she liked, soft, then firm, then some teasing. He then lifted her up to her feet, and pulled her sundress down around her ankles, then picked it up and threw it on the bar to join her bikini top. Then inserting a finger on each side of her bikini bottoms, he pulled them down around her ankles and she stepped out again and he tossed it with the rest of her clothes on the bar.

Charles sat there and enjoyed what he saw, Samantha was a beautiful woman, her breasts glistened in the moonlight and he saw that she had a little landing strip of hair just above her pussy, and that was all. While she stood there in front of him, he slid both of his hands up the inside of her legs, starting at her feet, moving north past her knees until they came to that point between her legs, which he instantly felt the wetness on his fingers. He took one finger and slowly moved it up and down her lips, once he felt his finger was completely wet, he inserted it into her pussy and she gasped.

The yacht then moved a bit and she found herself sitting back down looking right at Charles while one of his fingers was half way into her pussy. That is when she realized that he was still fully dressed. She felt strange being completely naked in front of a man who was caressing her body and just beginning to finger her pussy. "You seem overdressed" she told him, "Indeed I am" he responded and then stood up and began to take off his shirt which he tossed onto the growing pile of clothes on the bar.

His chest was fit and tan, with just a little hair which also seem to be bleached by the sun. She was looking at the bulge in his pants that was just a foot in front of her face. He undid he belt, unclasped his shorts, and slowly pulled the zipper down. As his shorts hit the deck, he flipped their last piece of clothing on the bar and she found herself starring directly at what had to be one of the largest cocks she had ever seen. 9 or so inches long she guessed and reasonably thick and it was sticking straight up at her. She noticed that he was shaven, or at least did not have much hair around his big dick. Reaching up with her hand, she cupped his balls to feel that there was no hair at all on them, then moved her hand up and around the base of his shaft.

His cocked twitched as she held it and she looked up to see him looking down on her and smiling. She smiled back and then looked back to his big cock just inches from her face. Slowly she slid her hand up and down his hard dick and loved how it felt around her fingers. Opening her mouth, she put her tongue out and gave the big head a lick, to which it responded with another twitch. Her lust took over as she opened her mouth wide as she figured she would have to, in order to put it in her mouth, then leaned forward and just as the head of his cock was entering her mouth, he stopped and said "Ladies first".

To say that she was disappointed somewhat was an understatement as it had been a long time since she had a dick in her mouth and much longer since she had actually wanted a dick in her mouth (sometimes she would give the obligatory blowjob when her boyfriend begged her to, but that was mostly it). She felt him guide her up so her knees were on the padded bench, and she was bent over the side of the boat while she was hanging onto the side. Charles grabbed a cushion and set it on the deck, then got on his knees which gave him a glories view of Samantha's beautiful ass which was right in front of his face.

He lifted her ass a little, then moved his tongue so it could lick her pussy lips which he did. As he gently sucked on her pussy, she let out a little moan. Charles pulled his head back and said "You can make all the noise you want out here, let it out". To Samantha's surprise, she let out a loud moan as he went back to licking her pussy and added a finger to the fun and was massaging her clit much to her enjoyment. "Do you like me playing with your clit" he asked her, "oh yeah, play with my clit baby, I want to come sooo bad", she replied. Who said that she thought to herself, which was not like her, but neither was being bent over a stranger's yacht and having her clit rubbed just hours after meeting him.

His fingers were magic on her clit, she felt her real life erotic story coming to life and she was loving it. The whole scene of a Caribbean island, yacht, handsome stranger was everything she had dreamed of and more, although being bent over the side of the yacht was something she had never imagined, but it was working for her. Two fingers made their appearance at the entrance to her pussy, the two slowly made their journey deep inside her love canal and she let out another moan into the night air "That's is sweetie, stick your fingers deep inside my little pussy", she said and could not believe the words were coming from her mouth. This gave Charles encouragement to continue his intense attention he was giving her.

As his fingers worked her clit and pussy, he

put his tongue to her lips and began a slow long lick all the way up the crack of her ass until his tongue reached that taboo spot of her round little hole. When his tongue hit her little rosebud, she felt electricity shoot through her body and her eyes opened and looked at the large moon just beyond the dark horizon. This is new she thought to herself as no one had ever licked her asshole before and that area had always been off limits to her boyfriends. She was about to say something to Charles, like "stop that", but as he continued to give her a rim job, some part of her actually enjoyed the feeling of his tongue on her asshole and another side, her fantasy side was enjoying the kinky aspect of having this rich, handsome man lick her there.

Charles paused from licking her little hole to begin more long slow licks up and down the crack of her ass from her pussy to her tight sphincter and even to the small of her back. Every time he reached her tight hole, her legs would quiver. He took the fingers that were massaging her clit, and moved them to where his tongue had been. With two fingers still probed her pussy, another started moving up and down her ass crack just as his tongue was just moment before. Samantha was in a daze with all this attention going on down there, more than she had ever had.

After a while, one of the fingers stopped right at the entrance to her virgin ass. It swirled around the rim for a minute, than she knew the real intention of his devilish little finger. She felt it slowly enter her asshole and she looked back at him to tell him she was not that kind of girl, but he stopped and said "let me get something to make this easier". What the hell did that mean she thought, but at least his finger was not probing her ass, but then again, the two fingers that were in her pussy were out as well, and she missed them.

He had gone over to the bar, opened a drawer and came back with a bottle of sun tan lotion, and then she felt the lotion being dripped down her ass crack and quickly realized what he had in mind. His finger returned to her asshole and rubbed the lotion around, to which she was just about to tell him to stop, but paused for just a moment as the slippery feeling of the lotion and the finger playing around her hole gave her a wild sensation that made her curious as to what would happen, so she did not stop him.

The finger stopped right on her virgin hole and slowly entered her ass down to his first knuckle. The feeling was indescribable to her right then, a mixture of pressure, a tiny bit of pain, but a feeling like she had never ever felt. Then she felt him move behind her and wondered what in the world this erotic mystery man would do next. She did not have to wait long as she then felt the tip of his hard cock at the entrance to her extremely wet pussy. He pushed forward slightly and to her surprise, his large cock slid into her. It must have been all the time his fingers worked on her pussy and the clit massage that made her so wet, and now that made it easy for him to begin his journey inside of her.

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