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Spring Break Slaves 2: Reporting from Pirate Cay

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windar

Teller of Tales
Sun, sand, palm trees, the soft waters of the Caribbean...Who doesn't love that? OK, a few of the broke college students lured to a rich man's private island as "Companions" have occasionally had to suffer whippings, depraved sexual exploitation, competitions where the losers pay a price, and other assorted torments, but the setting is lovely.

You may remember the first story in this series https://www.cruxforums.com/xf/threads/spring-break-slaves.7852/

which left two of our poor students, Tara and Delia, on the island after their classes resumed, due to circumstances beyond their control. Well, one of their fellow classmates (initials BM) notices that they haven't returned and decides to investigate. You will hear from her soon (a few complaints, perhaps?), so you won't have to suffer endless chapters of my writing.


This story should stand on its own, but for those who haven't read the first in this series, that would probably enhance your enjoyment. Now, sit back, mix yourself a nice rum cocktail and enjoy...



CHAPTER ONE



Delia Ortiz looked up when Tara Malone came back into their room. She was stretched out on her belly on her bed. Like Tara, she was naked. Also like Tara, her back and buttocks still had the marks of the whipping they had each received the previous day, tied together face to face, sisters in suffering, as punishment for their last place finish in the pony cart races.

They had been here on Pirate Cay less than a week and already their days as roommates at Pitcher College seemed a lifetime away. There, an ordeal had been a hard calculus test or a term paper on some obscure 18th century novel, not being auctioned as sexual playthings for randy Wall Street bankers or being flogged for some inadvertent failure to please, whether real, or made up to provide an excuse for them to suffer for the amusement of the assembled audience.

And at Pitcher, though neither of them were prudes, they wouldn’t have been so casually naked in front of each other. Even hanging in their dorm room, they would have been wearing T shirts and panties. But on Pirate Cay, when you were ordered to strip, you did so quickly, without questioning the reason. Besides, even though the welts that the cruel leather whip had scored onto their bodies had healed almost miraculously from the cream that the resident doctor had applied to them, the skin was still too sore to bear the touch of even the softest cloth.

Besides, here on Pirate Cay, Tara and Delia had become lovers, something that, as close as they had been back at college, Tara had thought about, but hadn’t dared to act on.

“What did he want?” Delia asked.

Tara could tell that Delia had been worried when their employer had summoned Tara to his inner sanctum after dinner. On Pirate Cay, one could well suspect that wasn’t good.

“It was so weird, Dee,” Tara replied.

“He wanted a blowjob? No, sorry, what would be weird is if he didn’t.”

“He didn’t, but that wasn’t the weird thing.” Dee looked at her strangely. “He wants to knock me up.”

“Get outta here!” Dee exclaimed.

‘You can take the girl out of the Bronx, but you can’t take the Bronx out of the girl,” Tara thought.

“That’s crazy! Why did he pick you? I mean, you’re great, Tara, but he barely knows you and as rich as he is he could have anybody, you’d think, like a movie star or a model.”

“He said that our DNA matched and that our kid will be some kind of genius who will rule the world.”

“He tested your DNA?”

“All of ours, Dee. They got it off of our water glasses at dinner. And he says mine is super Grade A1.” Tara couldn’t help feeling a bit proud of this, even though there was nothing she had done to accomplish this feat.

“So what did you tell him?”

“I didn’t feel I had much choice. You know what happens if you say no around here. I’m not up for another whipping or God knows what that might be even worse.”

“So, how are they going to do this? Artificial insemination? You jerk him off into a tube and the doctor sticks it up your girl parts?”

“He didn’t say, but I got the sense he wants to do it the old fashioned way.”

“Ewww!” Delia exclaimed. “Lucky you.”

“Well, you know, he’s not that bad looking, at least for an older guy. And he has a certain presence. I don’t know how to describe it, but you just find yourself listening to him.”

“A billion dollars will do that.”

“That doesn’t hurt, but I think he’d stand out in a crowd even if he was poor. Anyway, that means I’ll be staying here for a while. Like 9 months, I guess, maybe a bit more, depending how long it takes for me to, you know.”

“But what about school?”

“He’ll arrange a leave of absence. After that, he’ll raise the baby with nannies or whatever so I can go back to my life. He’ll pay off my student loans and give me a full scholarship and a bunch of money.”

“Tara Malone, you’re not seriously thinking about becoming a brood mare for this man? And you’re going to spend the next year in this hell hole?”

“It’s not a really hell hole, Dee. The beach is wonderful, the food is terrific and this room is ten times nicer than the dorm and a hundred times nicer than my Mom’s trailer.”

“Sure. All paid for with floggings and sex with his charming guests whether you’re in the mood or not.”

“He said no one else will be allowed to have me. I mean, he wants the baby to be his, right? And I don’t think he’ll have me whipped while I’m pregnant.”

“Dream on, girlfriend! He’ll do whatever the fuck he wants. Count on it. Thank God he picked you, not me.”

“Well…” Tara hesitated. She felt a bit ashamed that her mentioning Delia to him might have given him the idea to decree that she should stay as well to keep Tara company. Of course, it’s likely that he had planned that all along anyway as a gift to his good pal, the Right Honourable Sir Frederick Bascome, the Prime Minister of Providentia, the Caribbean island nation to which Pirate Cay belonged. Big Fred, as he liked to be called, both for his overall girth and that of his male appendage, had taken a shine to Delia. Nevertheless, Tara couldn’t rule out that her asking about Delia had put the idea in their employer’s head.

“What?” Delia asked, alarmed.

“He wants you to stay here, too, so that I’ll have company. He worries that if I get depressed and lonely it will be bad for our project. Also, he says the Prime Minister likes you and will appreciate it if you stay.”

“No way, Jose! You do what you want, but I’m outta here!”

“You’re going to go in there and tell him no? Good luck with that. The wounds from our last flogging have just barely healed and you’re going to ask for another one?”

Delia thought for a minute. “No, but since he likes you so much, you go in there and tell him that we’re not a package deal and that you can handle things here by yourself. You have Kelly for company anyway.”

Tara rolled her eyes. “Oh, God, that bitch! I’d rather have a boa constrictor for company.” Kelly Winters was his long-time assistant, the one who had personally recruited them to come down here. “Come on, Dee, we’re the Two Musketeers. The Dynamic Duo. We can face anything as long as we’re together. Besides, it’s not like you really have a choice, do you?”

“Fuck that, Tara! And fuck him and fuck Kelly and fuck Big Fred and fuck Pirate Cay!” Delia balled up her hands and pounded the mattress with each imprecation. Tara knew how she felt. But she had lost the will to resist by this point. Resistance only brought pain.

Besides, who was she, or Delia for that matter, to resist someone as rich and powerful and knowledgeable as him? It wasn’t like either of their lives had been so fantastic before they came to Pirate Cay. If they had been, they wouldn’t have come. But they were here, and here, obedience was required, so she would obey. And Delia would do well to do the same.

Tara moved over to Dee’s bed. There was just enough room for her to lie down, also on her belly to protect the still sensitive skin on her back and buttocks. Dee’s skin felt good next to hers, their hips and thighs just touching. She reached out to trace her hand gently over the almost healed welts across her friend’s upper back.

“Come on, Dee,” she whispered. “It won’t be so bad. Sun and sand, and the soft waves breaking on the beach. “

“I really was looking forward to going back to Pitcher.”

“There’s probably two feet of snow on the ground there. And not that nice fluffy stuff. No it’s probably all brown and crusty.”

“Yeah, but I won’t have to fuck dirty old men or eat out that nasty bitch, Kelly, there.”

“Oh, come on, Big Fred isn’t so bad. He’s kind of funny. And Kelly usually returns the favor and she knows what she’s doing. And we weren’t lovers there.”

“Yeah, but we could have been. Why didn’t we do it there, Tara?”

“I don’t know. I sort of wanted to, but I was afraid to ask. Here on Pirate Cay, you don’t need to ask; that kind of thing seems to just happen.”

Delia turned to look at her friend. “Yeah, it sort of does, I guess.”

Tara took her friends face in her hands and brushed the hair out of her eyes. “So, you’re not mad at me?”

“Well, maybe a little. Mad at your DNA anyway, because it means we can’t go home.”

“But it’s not my fault my DNA is so great. Or so great with his. There’s nothing I can do about that, is there?”

“No, I guess not,” Delia admitted.

“So we’re still friends, still the Two Musketeers, ready for anything?”

“Yeah,” Delia replied. “Sure.”

Tara pulled Delia’s face towards her and kissed her hard on the mouth. She felt a tingle running down her spine as her breast brushed against Delia’s breast. Delia returned the kiss, reaching out to stroke Tara’s hair.

Tara moved down to her lover’s neck, planting small kisses as she descended. Reaching Delia’s back, she encountered the first of the welts where the supple leather of the whip they had both endured had carved its mark into her skin. Only a trace of the angry inflammation was left, thanks to the doctor’s miraculous cream.

Tara let her tongue trace the faint, but still noticeable, line down her lover’s back. Dee sighed. “That doesn’t hurt, does it?” Tara asked.

“No, it feels good.”

When that line ran out, Tara found another one, letting her tongue lick across Delia’s shoulder blades and onto the side of her breast, where the tip of the whip had scored the flesh. Then, she moved down to Delia’s buttocks where a number of mostly healed welts crossed the succulent globes.

Tara let her tongue trace a few of the lines, inhaling her lover’s scent. She knew that Delia was right; that even with him having selected her that some hard tests still likely lay ahead, but together they would come through it, as they had come through their ordeal so far.

“I don’t suppose you want to roll over onto your back?” Tara asked.

“I don’t think so,” Dee replied. “Still too sore.”

“Then get up on all fours.” Delia pushed her torso up, supporting her weight on her hands and knees. Tara kissed her way down Delia’s ass until she reached the pouting lips of her friend’s pussy. She slid down the bed until her face was right against Dee’s crotch.

Tara reached down with both hands and spread Delia’s legs apart, giving her full access to her friend’s most intimate parts. Slowly, she ran her tongue up and down her lover’s slit. Delia moaned with pleasure.

Tara reached her hand up and spread the outer labia apart. Then, she just brushed the tip of her tongue against Delia’s clit before quickly pulling it away. Delia gasped. “You like that?” Tara asked.

“Do you really have to ask?” Dee replied.

“Then, I’ll do it again,” Tara said, flicking her tongue out again, just making contact. She felt Delia’s body shiver. “So, you’ll be good and do as he says and not get us into trouble?” she asked.

“Sure, Tara, whatever. Just stop teasing me and get down to business.” Satisfied that Delia meant it, at least for the moment, Tara reached her tongue out again, but, this time, she didn’t pull it away, but kept it inside Dee’s slit, moving it slowly up and down, lingering at the top with each pass to circle the sensitive bud.

“Oh, yes!” Dee moaned. “Please don’t stop. Please…”

And Tara didn’t stop. In fact she kept going, listening to her lover’s breathing, feeling her ass wriggling as the pleasure mounted, feeling Dee’s thighs pressing against her head to make sure that the she kept the delicious pressure against Dee’s clit.

“Oh, I’m going to come!” Delia exclaimed. It took only a moment longer before Delia yelled “Fuck! Oh, shit!” as her ass thrusted rhythmically against Tara’s head and her feet kicked madly against the mattress.

Tara kept the stimulation going as her friend’s gyrations slowly ebbed, then finally withdrew from between her legs and slid back up the bed. Delia lowered her torso to lie flat next to Tara, her skin slightly damp with sweat. She turned her head to look at Tara.

“So, it isn’t all pain and suffering here, right? We’ll survive, won’t we?” Tara said.

“I guess we will,” Delia replied. “I suppose you’ll want me to return the favor?”

“Do chickens have lips?”

“I don’t know about chickens,” Delia said. “But we do.” And, with that, she pulled Tara towards her and kissed her hard.
 
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CHAPTER TWO


Kelly Winters was pissed. In case a casual observer couldn’t tell from the angry expression on her face, the fact that she threw the small leather-bound notebook that she had carried with her into his office against the glass door leading to the patio of her room was a dead giveaway.

Kelly had been with him from the start, not long after graduating from college-a state school, not a fancy private one like Pitcher. She’d answered a classified ad-in print as they were in those days, not on-line-in one of those free community newspapers that had littered the cafes and bodegas in gentrifying city neighborhoods back then.

“Personal Assistant Wanted” it had read, much like the ones she placed on campus sites to recruit girls like Tara and Delia. He wasn’t a billionaire back then, just an ordinary millionaire who’d made some stock trades that he would have called brilliant, but that others might have called lucky.

Word of his success had quickly gotten around, and soon quite a few very prominent people had started asking for advice, advice for which they were willing to pay handsomely. It turned out that the only thing better than investing your own money profitably was investing other people’s and taking a cut, win, lose or draw.

At first, their relationship had been professional. She was his only employee at the time, handling correspondence, booking travel, accompanying him to dinners so clients could stare down her blouse as he gave them his pitch. Despite herself, she had found herself drawn to him, his self-confidence, his ability to charm powerful men.

So, when, one evening after a dinner at a very chic French restaurant with a grocery store heir from Ohio (or was it Michigan) he had invited her for a nightcap at his townhouse on the Upper East Side, she had accepted the invitation with only a little hesitation. The nightcap had turned into a few and when he had told her how attractive she was and how much he valued her work, she found herself unable to say anything but yes.

After that, they saw each other a couple of nights a week. Kelly hadn’t thought of herself as the kind of woman who slept with her boss, but she felt flattered to be desired by a man of such wealth and knowledge of the world.

And the sex was good. Not out of this world good, but good enough.

Then, one day, he had called her into his office from the small anteroom where she sat to answer the phone and greet clients. A bottle of bubbly mineral water sat on his desk. He picked it up. “This is Perrier, not Badôit,” he said, matter-of-factly.

“They were out of Badôit.” This was true-the gourmet market around the corner where she picked up water, cookies, sandwiches and other things for him and for various clients who might stop by had been out of it, so she had picked up another brand instead. Who could tell the difference?

Obviously, he could.

“Did you ask if they had some at another branch?”

“No,” she replied, nervously. “I thought the Perrier would do fine. It’s very popular.”

“Kelly, I pay you well, don’t I? You accompany me to dinners at very nice restaurants, don’t you?”

“Yes, you do.”

“And for that, I expect you to show some initiative, to take some responsibility.”

“I’m sorry,” Kelly replied. “I’ll go call around right away and see if I can find some Badôit.”

“Sure, but what do you propose I do in the meantime?”

Confused, Kelly had stammered, “I..I don’t know. Drink Perrier, I guess.”

“Well, I do know. That’s not good enough. Bend over the desk.”

Kelly’s heart skipped a beat. “What?”

“You heard me. Now!” he had said, not sounding like he was kidding.

Kelly’s head was swimming. He couldn’t mean to spank her like a disobedient child? But he was standing, removing his belt from his pants and pointing at the front of his desk. Kelly stood, frozen. What would happen if she said no? Would he fire her, send word around to his powerful clients that she was bad news? What would happen if she said yes? There were no guideposts in any of the career advice books she had read for how to handle this situation.

But he was staring at her and it seemed like the route of least resistance, as it usually was with him, was to obey. So, she laid her torso down on the desk, her head turned to watch him as he walked behind her, the belt dangling loosely in his hands.

She felt his hand lifting her skirt over her waist, then taking hold of her panties and starting to lower them over her hips. She started to get up. He pressed his hand down on her lower back. “Stay down, Kelly,” he ordered. He lowered the panties below her knees.

She sensed him taking a step back, then she heard the “Whoosh” and the “Smack!” as the leather struck across her soft, rounded globes.

“Oww!” she protested, squirming.

“Stay still!” he ordered.

“It hurts!”

“It’s supposed to,” he told her as he gave her a second swat. It had felt like fire across her ass.

Kelly wasn’t sure how many times he had hit her with the belt, perhaps a dozen or so. By the end, her ass was burning and tears were running down her cheeks. But, she remembered even this many years later how wet her vagina had been and how her entire pelvic area had tingled with excitement.

“Can I get up now?” she had asked, her voice choked with a mixture of pain and the humiliation of having been forced to submit and of having been aroused by it.

“No,” he had said coldly. She turned around and saw that he was lowering his pants and underpants. He was hard, as aroused from having punished her as she was from having been punished. None too gently he pried her legs apart and was inside her, her well-lubricated passageway allowing him easy entry.

He took her hard, looking only for his own pleasure, pounding deep within her, but it was what she needed. She gripped the desk, even harder than she had when he was whipping her, gasping as the orgasm tore through her. Then he pulled out and rubbed his cock against her flaming ass cheeks until he groaned with release, the warmth of his cum joining the heat left by his belt.

***​

Kelly poured herself a large glass of pinot grigio from the fridge in the small kitchenette of her room and took it out to the table on the balcony where she could stare out at the ocean. The ever-changing palette of greens and blues never failed to soothe her.

All those years she had served him loyally. Whatever he had wanted, she had done her best to fulfill. She had never asked for anything, just accepted what he had given. Not that he wasn’t generous in his way. She had lived well as he had prospered, in the city and then when he had bought Pirate Cay and built the house and its compound.

Still, it had come as a slap in the face when he had told her of his planned project with Tara. He had never told her that he wanted an heir, though it was understandable that he would. All that money had to go somewhere when he died and she never expected that he would leave it all to her, though she certainly had hoped to get something.

But if he did want an heir she would have been happy to provide him with one. The doctor checked her out regularly and had never told her that anything wasn’t working down there. He had insisted that she be on birth control and the doc had been giving her regular shots, but there was no reason to think she wouldn’t be fertile if those stopped.

But, she supposed, her DNA wasn’t good enough for him, not like that bitch Tara, whose genes were apparently going to give the world its next Einstein or something. Well, if Tara was so smart how come she had swallowed the lies that Kelly had fed her and her friend Delia to get them to come down here?

But his mind was made up and she would have to swallow it like she swallowed everything else over the years. To add to it, he was going to be entertaining an important guest, one who had been to Pirate Cay a couple of times before and liked to play rough. Kelly and the doctor had had to clean up a bit of a mess the last time he’d been down here. He had had to write an extra big check to the girls to smooth things over, but he made a lot of money through this guest, so it was worth it, he had told her. Plus he had enjoyed watching. So had she, for that matter.

Apparently, Tara, with her new found status, was protected from having to please this guest, and, it seemed her friend Delia was as well, so Kelly was being dispatched back up north to recruit a couple of newbies.

She opened her lap top, went to the Pitcher College Financial Aid Office job site and entered the standard ad that had worked so many times before: “Discrete Personal Companions wanted. Excellent pay. Paid travel. Not just a job, an Adventure! Call Kelly xxx-xxxx”. She hit “Post” and took another sip of wine.
 
She opened her lap top, went to the Pitcher College Financial Aid Office job site and entered the standard ad that had worked so many times before: “Discrete Personal Companions wanted. Excellent pay. Paid travel. Not just a job, an Adventure! Call Kelly xxx-xxxx”. She hit “Post” and took another sip of wine.
The Pitcher College Office of Financial Aid really ought to be scrutinizing such advertisements. They have a responsibility to protect as well as serve students, one would think. Wait till the lawyers get hold of this!
 
Kelly poured herself a large glass of pinot grigio from the fridge in the small kitchenette of her room and took it out to the table on the balcony where she could stare out at the ocean. The ever-changing palette of greens and blues never failed to soothe her.
inline_image_preview.jpg

Not a manip. Only a photo for illustration.
 
Kelly poured herself a large glass of pinot grigio from the fridge in the small kitchenette of her room and took it out to the table on the balcony where she could stare out at the ocean. The ever-changing palette of greens and blues never failed to soothe her.
View attachment 995003

Not a manip. Only a photo for illustration.
Makes me want to join her...

I hope people aren't finding Kelly's story too much of a distraction. When I wrote the original, I found myself wanting to know how she came to be doing what she is doing...
Introducing Limericks to the work of Windar,
May be going one step too far.
He`ll not be best pleased,
At being so teased,
And later on, your tight little he`ll scar.
With limericks, I can't be too mad
Nor even too terribly sad
For I started the trend
And must make amends
So I'll try not to be a real cad
 
CHAPTER THREE

Kelly relaxed into the plush seat of his private plane as it banked north after take-off from St. Francis, the main island of Providencia, where flights from the mainland and other Caribbean islands landed. The flight crew had stowed her suitcase, in which Kelly had packed a couple of heavy sweaters, boots and a down-lined jacket for her trip to the frozen tundra of late-winter Pitcher College.

By now, Kelly couldn’t even count how many recruiting trips she had made up from Pirate Cay to some college town or other to recruit new blood for him and his clients. Once she had been enough to satisfy him all by herself, but those days were gone now.

She remembered the time after the belting he had given her in the office. That incident had awakened something that had lain dormant in him and in her as well. He had bought some “equipment” from a store in the Village that specialized in kinky fantasies and set up a little playroom in the basement of his town house.

It wasn’t something they did all that often, but now and then, when he felt the urge, he would order her down to the basement, have her strip naked and they would enact some fantasy that he had picked up God knows where that would end up with her shackled to the ceiling or bent over a wooden horse taking a dozen with a cat o’ nine tails or a cane, punished for some misdeed, real or imagined. Then afterwards they would fuck.

The whippings and canings hurt a lot, much more than the belt, and left marks that lasted a week or two. Kelly often asked herself why she accepted it. She was free to leave, of course, and she had thought about it more than once. But he would buy her something nice after the sessions to ease the pain.

More importantly, though she wasn’t proud of it, she was honest enough to admit that it turned her on to be tied up, helpless, under the control of a powerful man. The orgasms she had afterwards were always amazing and his seemed to be pretty damn good, too.

Eventually, he had the idea that it would be fun to “share” her, perhaps with a friend or an important potential client. Kelly had resisted that at first. Sleeping with your boss was bad enough, but she was hardly the first to do that. However, being passed around would definitely make her a whore in almost anyone’s book.

“Look, aside from the fact that it will be good for business if a few select clients can not just look down your shirt, but actually enjoy your very lovely body, more importantly, it will turn me on,” he had told her.

“Really, why?”

“It’s hard to explain, Kelly. Male bonding perhaps, something in our DNA from back when we lived in caves. I don’t know, but I think it would. I want you to try it once and let’s see.” As usual, when push came to shove, she did what he asked.

The first time was with one of their biggest clients at the time, in both the financial and physical sense, a Texan who owned a bunch of oil wells and was looking for advice to diversify his investments. He decided that they should entertain the Texan at his town house.

The dinner was brought in from a very well-regarded caterer, so Kelly didn’t have to cook. She did, however, have to serve the food dressed in a ridiculous-looking serving wench costume whose front started just below her tits and ended just above her pussy. As for the back, there wasn’t any.

Kelly was thoroughly embarrassed to be seen in it. But, she not only had to serve, but had to stand there as they ate and discussed the markets and tax shelters (she had eaten in the kitchen before their guest arrived). The Texan spent so much time feeling her up that it was a wonder he was able to clean his plate.

After dinner they retired to the living room for brandies while she cleared the table. Finally they called her over. The Texan was on the big leather sofa, while her employer was sitting in an armchair facing their guest.

The Texan indicated a spot next to him. “Come and join us, Kelly, darlin’. I don’t bite,” he said. “Not hard enough to break the skin, anyway.” The two men laughed.

She sat next to him. He draped an arm around her shoulders, his hand stroking her breast, the fingers pinching each nipple in turn. “Your boss tells me that you’re a very skilled young lady.”

“He’s a great business mind and a terrific teacher and I try to learn as much as I can.”

“I’m sure you do, Kelly. But your boss and I have talked business for a goodly while now and I’m ready for some fun. He tells me your skills go way beyond business, if you know what I mean.” In case she missed his point, he stared down at his crotch.

Kelly looked at her boss. He nodded. Whatever doubts she had about carrying through with this, it seemed a bit late to worry about that now.

The Texan pushed himself partway off the sofa so that Kelly could open his trousers and lower them before he plunked his ass back down on the fine leather. Kelly took his dick in her hand and started stroking. She could feel it getting hard.

‘Well, it’s now or never,’ she thought, sliding off the sofa onto her knees. As she arranged herself, she stared over at her employer. He had, like his guest, lowered his pants and was sitting in the chair slowly stroking his penis, which was hardening rather quickly.

The Texan was fully erect now. Kelly stuck her tongue out and began licking slowly up and down the shaft. The Texan sighed. “That tongue is soft as two minute egg, as we say down in Texas.”

Her boss had his eyes closed now, stroking in time to Kelly’s tongue. After a few minutes, he stood. “You mind if I come in from behind?” he asked their guest.

The Texan was breathing heavily now. “Course not. This lil’ gal could handle an army, I’ll bet.”

Knowing what was expected, and, despite her sense of shame at being portrayed as a whore, being quite wet and wanting him, Kelly lifted her ass, presenting herself to him so that he could slide right into her, as she continued stimulating the Texan.

“Now this is a business partnership a man could get used to,” the Texan exclaimed, his voice tight with his rising excitement.

Kelly continued working on his cock, pursing her lips around the head and slurping her tongue against the shaft. Meanwhile her employer was fucking her hard from behind, his eyes fixed on the action in front of him.

“Get ready, little lady, this is going to be a Texas-sized load,” their guest proclaimed, shortly before he moaned and began cumming in her mouth. His climax stimulated her employer to make his final thrusts. Kelly could feel his warmth flowing inside of her as he collapsed on top of her, pushing her body down onto the fully satisfied Texan.

***​

Kelly looked at her watch. She guessed from experience that the plane was somewhere off of Florida. Still another couple of hours to go. She stood and walked a few steps to the small galley. She took out a bottle of champagne from the refrigerator-the good stuff, Veuve Cliquot La Grande Dame. ‘Might as well enjoy,’ Kelly thought. She loved the popping sound of the cork, extra loud up here due to the lower atmospheric pressure.

She poured herself a glass and selected one of the sandwiches from the tray in the galley drawer and returned to her seat.

‘Yes,’ she thought, ‘That is what I did for him back in the day.’ Which is why this thing he was planning with Tara was such a slap in the face.

Kelly often tried to calculate how much she had contributed to his success back then. While there were certainly plenty of clients whom she didn’t sleep with, and his financial acumen was valuable all by itself, she couldn’t help but feel that the Texan wasn’t the only client who sent business his way because of her efforts to please them.

Regardless, his business took off, and soon there were more clients than she could service even if he had wanted her to. And he could hardly have the type of parties he wanted in a city townhouse. How exactly he found it, he had never told her, but one day, he had called her in to show her a set of aerial photos.

“It’s called Pirate Cay. It’s presently uninhabited, but the government of Providencia is looking to develop it. For the right price and a promise to hire some locals from adjacent islands, it’s mine.”

Kelly glanced through the portfolio. There were palm-fringed beaches with sparkling white sand leading down to crystal blue waters. The interior was jungle with a high point that looked to be a few hundred feet above sea level. “It’s gorgeous!” she exclaimed. “And you want to build there?”

“Yep,” he said, pointing to the largest and most beautiful stretch of beach. “Right here. It will be totally private. We can play to our hearts’ content. And with a good satellite connection, I can do business just as well from there as from here.”

“Wow!” was all Kelly could think of to say.

Shortly thereafter, he showed her some preliminary plans from the architectural firm he had hired. He wanted her input and she had given it freely. It wasn’t an exaggeration to say that many of the house’s features had come from her suggestions.

As the house was nearing completion, he started talking about his plans. “Kelly,” he told her, “Once we move down to Pirate Cay, I don’t want or expect you to entertain me and my guests. I see you as in more of a management and supervisory role.”

Kelly smiled. ‘A promotion! Recognition for her abilities!’ This was what she had hoped for.

“I see you as recruiting talent. I’m thinking we can attract desperate college students. Offer them a nice sum of money, more than they could make in a year, for a week of sun and fun during winter break, spring break, whenever. I’m thinking we can start at Pitcher College.”

“It’s my alma mater, you know,” he continued. She nodded. “Not to mention I give them a ton of money. So they can smooth our way, if you get my drift.”

Kelly nodded again. “So what do you see me doing?”

“Interviewing the girls, selling them on what a good time, they’ll have down there. The beach, the pool, the money they can earn. I don’t have time to do that and even if I did, they are going to be creeped out by an old guy like me. They’ll be much more willing to trust a woman, especially one close to their age.”

“That’s certainly true,” Kelly responded.

“And then when they get down here, you can show them the ropes, be a friend, a shoulder to cry on if they find things aren’t exactly as they had planned, if you get my drift.”

Kelly certainly got his drift.

And she found it was a role that she was good at. She could handle the inevitable questions of innocent undergraduates, make them believe they’d have a great time on Pirate Cay, be the sympathetic, but firm big sister when they got there and found out some of the things they were expected to do and what would happen to them if they didn’t.

Moreover, Kelly found that she enjoyed the work. As wet and aroused as she’d gotten from being tied up and whipped, she found it even more arousing to watch some girl that she had recruited suffering under the lash or other tortures that he and his guests devised, sometimes with her input.

And then there were the delights she could enjoy with them in their rooms, “comforting” them after a particularly hard session. Though she had only been with men before, she quickly found she liked women’s bodies, pleasuring them and being pleasured by them in her turn. After years of doing these things they had gone beyond a pastime to a way of life.

As hard as his taking up with Tara, whom Kelly had, of course recruited, was to swallow, could she really give up all that she had become accustomed to?

Once the plane landed and the car took her into town, she could walk away from it all. Catch a bus to the city and disappear. But where would that leave her? She had only the cash he gave her for incidentals on her trip and a credit card on his account, which he would cancel as soon as it was clear she’d skipped out.

The money he had supposedly paid her over the years was in an account in one of his funds. She got regular statements and there was a decent amount there, but she couldn’t access it without him. Sure, she had a legal right to it and could sue, but he could tie it up for years with fancy lawyers.

And with no employment record besides with him, what work could she get? She saw herself ending up as hostess at a chain restaurant in a mall somewhere, living in a crappy apartment with a couple of co-workers. No Caribbean beach, no Veuve Cliquot, and no hot young students to play with and manipulate and watch writhing under the whip.

Taken in totality, the choice was easy. She’d check into the College Inn as she always did when she was recruiting at Pitcher and she’d put on her most charming smile and her most ingratiating manner and con a desperate poor student or two into coming down to Pirate Cay. And once back there, she’d look for every opportunity to undermine that bitch, Tara, and her friend Delia.
 
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