Grace's Caribbean Holiday

This continues Grace's exciting Summer holiday, with a very unexpected, shocking and lucrative ending. I suggest you start with chapter 1,

Grace struggled out of bed to meet with Werner as arranged, for a short boat trip and what would inevitably follow. She had met him once and much to her surprise, really enjoyed their time together. It had been an easy, but very stimulating start to her week's work and she was beginning to understand it was hard work. The previous night's threesome with Don and Ralph had been wonderful, but left her feeling bruised and battered.

No matter, a job was a job and she needed to be at her best for her German friend and she was sure, a quieter afternoon. So Grace showered and surveyed the damage, not as bad as she had expected. There were a few bruises and bite marks, she hoped might add to her allure, but she wasn't convinced. She really looked as she felt, very much the worse for wear. When she'd put on her barely decent bikini and sundress, Grace went to discuss it with Simon the hotel concierge, her arranger/pimp.

She entered his inner sanctum when the knock at the door was answered.

"Simon, can I discuss what I see may be a problem. Don and his friend last night, great, wonderful, but very intense and a bit damaging. Maybe i should have been more careful and set limits, my fault.

May I show you?"

"Of course"

She slipped out of her sundress and stood practically naked, turning round to show her injuries. All he could do at first, was marvel at the body, then of course, he took in the damage.

"Look, don't blame the boys, I might have encouraged them, I certainly didn't try to stop them. I'm not proud to admit I enjoy the rough stuff, even very rough.

It never occurred to me that it might reduce my street value, to put it crudely, over the week and I've only just started. Has the issue come up before?"

Simon sat to hide his erection, she certainly was a very stimulating piece of flesh.

"yes it has and I should have warned you, but I didn't want to frighten you more than you seemed on the first day. I have to say that some men might find the bruising attractive, but then that may make them violent too. I don't think we are going to lose bookings, but we need to protect you. No more group sessions booked and we won't make any more, except for couples and you do have one of those tomorrow Let's stick to single men and exclude the obvious Neanderthal brutes shall we. I'll make it clear that your clients must be gentlemen.

I can only apologise, but obviously over enthusiasm, shall we say, is an occupational hazard we shall try to mitigate."

Grace was grateful and touched by the obvious concern.

"One other matter Grace and don't worry about it, the problem often arises. You have been careful, but it's hard to hide the fact that you are making yourself available, shall we say. I say again, it's not your fault, but some of the American wives are concerned. They feel threatened, you are a young very beautiful women, who seems sexually available and that they fear, includes their husbands.

Just be aware if you could, avoid eye contact, you know. Now rush off before your next appointment with Werner.

Quickly putting on her sundress, she rushed off to the jetty, where Jim, the Captain from the snorkelling trip were looking impatient.

"sorry gents, I had to see the concierge."

She gave Werner a kiss on the cheek and they all climbed aboard. Jim used his engine to leave the area of moored boats, then raised the sails and they moved towards the island in a delightful cooling breeze. This truly was the life.

In it seemed too short a time, Jim moored the boat 50 yards from the island shore. They could have swum to the beach, but there was a hamper, towels, a blanket, so Jim rowed them in the dingy tied to the yacht and helped to unload. He had to admire the girl, way above his pay grade, but a man can dream. This was before she threw off her sundress and stood near naked 5 yards from him, with a nice tan already developing. She smiled at his lustful look.

Jim really didn't go for white women and he had a wonderful partner, always ready for sex. But this creature in front of him not only looked great, but looked like she was up for it, anything, gasping for it. That was something he rarely saw in a white bitch. This wasn't going anywhere, so he turned and rowed back to the yacht. After climbing on board and opening a cold one, he gazed back, better and better. They were both playing in the water and she wasn't hiding that she had no costume, as she jumped up and down her tits swinging.

The German gent grabbed her and pulled her to the beach. They kissed briefly, till she was thrown onto a blanket. Immediately she spread her legs for him and he fell to his knees then straight into her. She moaned and tried to raise her hips to increase the penetration. Jim was surprised the man had it in him, but Werner started slamming into her, with all his weight behind the effort. Grace started moaning and thrashing from side to side, it didn't seem put on, she was enjoying the hard fuck. Jim was even more surprised that Werner didn't come with the effort, if anything he increased the power of his thrusts, so that Grace seemed to shudder with each deep penetration.

Good for you man, Jim thought, give her what she wants. He could hear her moans increasing, till she screamed with her first orgasm and shook from side to side. Jim couldn't believe it, the man kept going on and on, it seemed even harder, till they both came together after another 5 minutes and Grace was twitching and gasping for breath for some time. When they both finally recovered and sat up, they high 5'd each other and laughed, hugging and kissing. Definitely my kind of gal he thought.

Werner stood up and pulled her to her feet, then they walked slowly into the sea. Werner seemed oblivious to Jim, but Grace smiled and gave him a wave. He waved back and felt the stirring in his old denim shorts. Dear Lord, what he wouldn't give for even 5 minutes alone with her. Dream on boy he thought.

They both swam for several minutes, they were strong swimmers, till they returned to the beach to explore the picnic basket. Grace unpacked and Werner opened the chilled bottle of white wine and another of water. They were hungry after all the effort and ate greedily, laughing and chatting like old friends. Considering her occupation, a whore, at least for a short time, this girl was good, a natural. She was eager, obviously enjoyed sex and put her partner at ease. Perhaps she should do it for a living, it would pay more than her current job, whatever that was, if she had to pay for a two week holiday on her back.

When they finished lunch and packed away, they both lay down for a sleep. Jim was not sure what it meant, but she lay with her thighs spread, maybe for him to see, he couldn't know, but for the first time, he reached for binoculars for a good look. But my word, what a beautiful, shaved fanny, still leaking a little cum.

After a short sleep, the man stirred and reached over to Grace, his hand going straight between her legs. She woke and responded immediately, kissing him as he groped at her beautiful breasts, gripping them hard. She spread her thighs wide for him and gripped his cock, pulling him towards her. He was nearly erect, but she swallowed him, then sucked and licked him to a good size. He bent down to her ear and she giggled and waved her finger at him. What had he asked?

It didn't take long to find out, as she sat up, reached into the basket for a small bottle of olive oil. Sitting up a little she squeezed a generous amount above her anus, then pushing a finger, then two more into the pretty pink hole. Man he wasn't going to do that and she couldn't be going to agree, but they were. Grace spread herself wide and pulled her knees up as far as she could. He immediately positioned himself. It can't have been deliberate, but she was lying a little to one side, giving him a better view, then a perfect one as he moved to the back of the boat, taking the glasses with him. He felt guilty, a pervert, as he focussed the lenses. Werner was just pushing at her tight hole. He was gentle, but Grace shuddered, threw her head back and groaned, as he pushed his glans past the resistance. Then she seemed to relax a little, till he started gently thrusting, going deeper each time. Despite the pain, she seemed to be whispering encouragement. After a couple of minutes, his groin touched her ass cheeks and he rested a little. Then he drew back and pushed in, each time a little harder, till finally, he seemed to be thrusting into her ass as hard as he had in her fanny. No question, she was enjoying it too, despite the obvious pain. She seemed to try to push herself towards him, to increase the penetration. What a woman he thought. It took a long time, but finally they both reached a climax and she really shrieked as she did. It was so loud. he thought they might hear it back of the hotel.

It took longer for them to recover, then they pulled themselves to their feet, staggering with the effort. She was, definitely was, looking straight at him. Werner was oblivious of Jim's presence, but Grace put her hand o her mouth and giggled, as Jim mimed roaring applause and clapping. Grinning, she gave a little bow to acknowledge his enthusiasm for her performance.

After another swim, they returned to the beach, fell onto the blanket and slept in the hot sun. At 3pm, Jim pulled round the little dingy and rowed to the shore, then gently called over to wake them. Werner pulled on his swim shorts and a T shirt, but Grace didn't bother. She collected up her dress and costume, but went back aboard naked,

Quite relaxed, she actually said to Jim.

"I hope you weren't bored waiting for us Captain?"

"No mam, I kept myself busy on the boat."

"Yes I saw how engrossed in your work you were." and grinned at him.

As they approached the dock, she remembered again about using condoms, too late. Oh well, she'd just visit the clinic for swabs and a check up, when she got back to London. When Jim moored the boat, Grace made a small concession to modesty and pulled on her string bikini bottoms That just made her look more sexy.

As they got off the boat, she turned and thanked Werner for a wonderful day. He slipped a small bundle of notes under her bikini and she kissed him to say thankyou.

"Werner, the captain has been so kind, waiting hours for us, I'll just help him unload and tidy the boat."

"No need for that mam, it's my job, what I'm paid for."

"I know that, but I'd like to, is that OK?" and she gave him a very warm grin.

"Of course it is mam, always welcome help from a beautiful lady."

Grace lifted the picnic basket, blanket, towels onto the dockside, as one of the staff walked up to collect them, transfixed by the vision in the boat. Grace couldn't resist turning round and bending to the floor of the boat to show her ass. As she did so, a trickle of cum squeezed around the micro piece of material in the cleft of her buttocks. As she stood up and turned around, the man was actually shaking.

Jim was collecting up ropes and other bits off the boat, the oars from the dingy, carrying them into the boathouse at the beach end of the dock. She took the last load inside the door of the old wooden building. Standing there, hands on her hips, she stared at him hard. No she couldn't do this, it had been clear that there was to be no fraternising with the staff and she had another client that evening, in only 3 hours. It was no use, she had too.

"Captain, I really don't know how to thank you, it was a such wonderful day."

As she made that innocent remark, she pushed her bikini down to the floor and stepped out of it. This time she had picked a condom out of her bag already. Jim gave out a deep growl, pulled off his shirt, tore off his shorts and shoes. He didn't even go to the back of the hut to close the doors, just reached for her waist and pulled her into his chest, as his hands moved down to grip her ass. She reached down to his swelling cock. My word, no anal sex this time, he'd have ripped open her ass. Dropping his head down to suckle her beautiful tits, he forced his cock against her tender pudenda. Oh my word, he was big and so strong. Grace struggled to her knees, as he held her so tight and expertly fitted a condom, then stuffed him in her mouth. She'd never liked sucking on rubber, but his cock was so beautiful. He held her head, trying to force in as much as he could. Despite her renowned cock sucking ability, she still only managed 3/4 of his length and that made her choke and gag.

Jim wasn't interested in her mouth, or foreplay, so he pushed her down on a dirty old sail by their feet. He knelt down, forced her willing thighs open and pushed a large pile of rags under her ass. With no warning he positioned his cock and pushed in hard. Luckily she was swollen and lubricated by Werner's semen. Still, she tried to push his chest, push him away from the tender hole between her thighs, gasping with the effort and discomfort. He wasn't to be denied and he started fucking her hard, really hard. Her buttocks were grazed by the coarse rags she was lying on and she could only try and hold on for the very rough ride. Fortunately, he came quickly with a roar, as he ground against her pubic bone, pumping into the condom. She didn't come, but she didn't need to every time. It had been a wonderful, fast, hungry fuck. He stood up quickly, no thanks, no gentle stroking, he just pulled her to her feet and handed her the bikini bottoms. Werner's tip was still in the folds and she took off a couple of notes and handed them to him. He took them without comment.

She pulled on her bikini and looked for the top and her sundress. As she bent down, he gave her a hard slap on the ass and said.

"You're beautiful and a great fuck girl."

She turned and smiled, somehow it seemed the perfect thing to say, no thanks, no gratitude, just, you are a great fuck girl. Oh well, she pulled on her sundress and picked up the rest of her stuff. Neither of them said anything else, but she turned and waved as she left the boathouse. She thought to herself that is if it were possible, she was becoming more of a shameless tart everyday.

Following a familiar pattern, she staggered to her room, exhausted, had a quick shower, carefully douching her fanny as best she could, with the shower head. After setting an alarm, she fell into bed and fell asleep in a few seconds.

True to his word, Simon's appointments for the rest of the week, were uneventful, enjoyable though. They were one to one with nice, attractive, gentle men. Her poor aching pelvis started to recover and she looked less like she had been run over by a truck, each day.

The meeting with a married couple was a new experience for her. Though she wasn't bisexual, she had enjoyed a number of encounters with girls, but never one man shared by two women. The wife was very pretty and her gentle hands and mouth were a delightful contrast with her husbands rougher more demanding attentions. He had fucked them both twice, the first time on their knees on the bed, bent forward on their elbows. He had switched back and forth, doing both hard and for a creditably long time. The girls had reached to kiss and fondle each other as he worked on them. Neither girl came, but that wasn't surprising with two to please. As he watched, the girls got into a 69 position, lapped and sucked each other to an orgasm.

They collapsed in a heap into an exhausted sleep until they woke in the middle of the night and ended flat on their backs, thighs spread, legs entwined and asses lifted high by pillows and cushions. Again the man worked hard till he came, but the two girls then helped each other.

It really had been delightful and Grace decided to try and find a willing couple back in London, for regular sessions. In fact she was to arrange her own repeat ménage a trois the following week, by carefully approaching another couple, unmarried this time. Her gentle hints were eagerly picked up by the couple and they hurried out of the bar arm in arm. There were more ugly comments between several of the small group of her established enemies, as they left. She hadn't sought this antagonism and there seemed nothing she could do to defuse it.

In fact, after the end of her first working week, the only session in the second week, was with the man and woman. Grace was grateful just to relax, swim, sleep on the beach loungers, sipping cocktails and enjoy the wonderful food. She did enjoy several evening meals with attractive men, but discouraged suggestions to join them in their rooms. Grace needed to recover her strength before returning to her very demanding job.

Then, three days before her return flight, the crisis happened, out of the blue, no warning, it was a real shock. She received a message to please go to Simon's office for a chat after breakfast. When she arrived, he was clearly worried, as he poured her a coffee.

"We have a problem and I mean the hotel, not you, but I want to talk to you about it. Nothing like this has happened before."

Grace was getting alarmed.

"For goodness sake, what is it Simon?"

"You remember we talked about the restlessness and antagonism towards you, with some of the American wives? Well, it has boiled over. I had an angry delegation from six representatives last night. You can guess the gist of it. Why was the hotel tolerating a whore picking up men whilst staying in the hotel? Why hadn't we done anything, thrown you out, called the police? They feared you had approached, even fucked their husbands, whom clearly they don't seem to trust.

So on and so on, then the really alarming part, if the hotel wouldn't act, they would, call the police, give the story to the island newspaper. There was an alternative, we must arrange to take you down. Even I was shocked. They wanted a group of our largest staff members to attack you, even I'm sorry, but to beat you, gang rape you.

Relax Grace, of course that isn't going to happen, that is quite clear and I have been to the hotel directors and we are all absolutely firm on that, no chance at all. You may be surprised, you are popular with the boys and girls who work here, your courteous and considerate to them. Even if we had entertained it, I am sure no member of staff would have agreed to take part.

So, what are we going to do, well we thought up a plan where we might both win, let me explain. By chance we have an American film director staying, not Martin Scorsese I'm afraid, this man makes porn films, well someone has to. One of his projects is a subscription channel where viewers pay for an event to be live screened and they only use amateurs, no porn stars.

Well, just a thought and we have talked to him briefly, what if he did one of his shows, with you and a few of the boys? These women insist that they watch your punishment, with their husbands, as a treat for them. So we could film it, with a feed to the room with these sadistic bitches and the main transmission to the subscribers.

Why on earth should you agree? Well, each viewer will pay $100 for the show and there will be hundreds, maybe thousands. If we film a scene setter today, that gives nearly 2 days to bring in viewers. It would be you on a lounger being rude to the staff, threatening to report them. This is the director's idea and he knows that you near naked on a lounger, will bring in a lot of viewers. Evidently they pass each other messages of what is coming up. The scene will shift to the staff angrily complaining about how awful you are. They are overheard by a couple of the women. The Director should be speaking to them now about filming for them and he'll try and catch them asking some boys at the pool to help them, for money of course. They want you punished and are happy to pay these guys to do it. They talk about what they are going to do to you, beat you, rape you, sodomise you, all the gory details. of course the men agree and we are set up to film it all tomorrow evening.