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Spring Break Slaves 2: Reporting from Pirate Cay

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‘This would be my life if I left him,’ Kelly thought. ‘Stuck in a room, probably not as nice as this one, with no maid service or room service.
No maid OR room service! I thought there were some limits on CF as to how realistically and graphicly punishments could be depicted! This is inhuman!
She had hated the communal showering that took place in the ramshackle old dorm in which she spent her freshman year.
Though I'll bet many of the men (and several of the women) in the dorm looked forward to Barb showering. :very_hot:
writing with a blue felt tip pen in her neat flowing girlish style,
:very_hot::very_hot:
she would dress very conservatively but attractively ... medium blue sweater, dark skirt to just above her knees, and low heels ... hair worn long and casual on her back.
:very_hot::very_hot::very_hot:
she chose to linger outside for awhile,
Barbara waiting in the light snow (a Minnesota girl would hardly notice).
793254.jpg

Nice section - the story, and narrative seemed to flow effortlessly. I can't help but hope (lust) for these two to finish the evening back in the hotel room, exploring the opportunities presented?
 
CHAPTER SEVEN

‘There’s really fuck-all to do here,’ Kelly thought. She’d been here for three days waiting for someone to call the number listed in the ad. Normally, she would have had a few responses by now, but the students had just returned from Spring Break and most weren’t looking to leave just yet.

Unfortunately, the Senate didn’t co-ordinate its recess with the colleges and next week was when the Senator could get down to Pirate Cay for some sun and fun. But there was talk of a bill that would hurt her employer’s business-not the monkey business with the female students, but the real money-making business.

The Senator would vote against it anyway on the grounds that it was a “socialist job killing something or other”, but if they really wanted him to go all-out to kill it dead and drive a stake through its heart, a play session with some hot young females was just the ticket.

And, most of all, the Senator liked to “break in a new one”, and Tara and Delia had already been broken in more or less, so Kelly really needed to find a raw recruit.

She’d spent time in the gym, which his donations had paid for, walked the few commercial streets of the town, stepping through the slush that lay there in the forlorn hopes of a spring thaw. She’d watched movies on her laptop and ordered meals from room service.

She’d sat in a few coffee houses trying to send out vibes in the direction of any attractive female students, but she didn’t think that “Hey, wanna come down to a private island to be the sex toy of a rich dirty old man and his pals?” was a line one could just toss out as you waited for your latte.

Last evening, Kelly had gone to one of the college bars. She’d been hit on by a bunch of male students-‘at least I still have it’, she had thought. She’d actually been tempted to take one of them up here to her room, but decided it was better to stay focused on her mission.

‘This would be my life if I left him,’ Kelly thought. ‘Stuck in a room, probably not as nice as this one, with no maid service or room service. Certainly none of the thrills that life at Pirate Cay held.’ And then, her phone rang.

Kelly glanced at the number. It was a local number, not him. “This is Kelly Winters,” she said.

“Yes, um, Ms Winters..um..I…I’m calling about the ad you placed. My name is Barbara Moore.”

“Hello, Barbara, you can call me Kelly,” she replied, putting on her sweetest, warmest voice. “It’s really nice to speak with you. Tell me about yourself.”

“You can call me Barb. I’m a sophomore, from Minnesota, majoring in business,” she replied.

“Well, that’s just perfect! The man you’d be working for is a very successful businessman. You would learn more about business in a week working for him than you will in a year of classes. And he has contacts allover. If you want an internship or a job when you graduate, he can help you.”

“That sounds great, Kelly!” Barb exclaimed. “But what is this job about exactly?”

“Why don’t we do this, Barb? Come over here to the College Inn for dinner and I’ll tell you all about it. I’ll show you pictures of the island, the house, the beach. You’ll be blown away, I promise! Dinner’s on me. I’ve eaten in your cafeteria and the food here is much better, trust me.” Kelly knew it was always good to get a prospective recruit to trust you, even on something trivial.

“Um..OK. That sounds good, Kelly. What time?”

“Let’s say 6:30. Is that good for you?”

“Yes,” Barb replied.

“Just come to the dining room and tell the hostess you’re meeting me and she’ll take you to the table. See you there. I’m really looking forward to it!”

“OK, Kelly, I’m looking forward to it, too.”

Kelly took a deep breath, then began typing on her laptop. “Got a possible prospect. More later.” She hit “Send” then headed for the shower.

***************

Barb checked her phone for the time. Nearly 5:30 ... time to get a shower and get ready for this dinner with Kelly Winters, she thought to herself.

Gladly setting aside the totally incomprehensible reading assignment she needed to plow through for next week’s meeting of her social theory course, she stripped down and headed for the shower. As she tested the water temp before stepping in, she reflected on how grateful she was to have won the lottery and landed a place in Pitcher’s much ballyhooed ultramodern ‘super dorm’, with its private rooms and en-suite bathrooms. She had hated the communal showering that took place in the ramshackle old dorm in which she spent her freshman year.

Ten minutes later she was out of the shower and lying naked across the bed, her hair wrapped in a towel. Pulling out a legal pad, she rolled over on her tummy and began to make notes regarding her earlier phone call with Kelly Winters as well as her thoughts about how she planned to handle their dinner date. One of the first maxims Barb had learned and committed to memory about investigative reporting was to always make careful notes, and include everything.

So, writing with a blue felt tip pen in her neat flowing girlish style, she began with the heading: ‘Kelly Winters: phone call impressions’.

The first thing she made note of was the woman’s easy manner ... her ability to put her caller instantly at ease, establish familiarity, exude warmth, instill trust ... in the latter case, even to the point of commiserating over the poor quality of campus dining-hall food. ‘The woman is a pro’, Barb wrote, followed by three exclamation points and underlined twice.

The second thing to note was how quick the woman was to discern an opening and dangle enticing promises. Barb had purposely lied about her major field of study, offering up business in place of journalism. Winters had pounced on it immediately, eager to plant the idea that embracing this opportunity could have long term business career benefits.

Then Barb started on a new section she dubbed ‘strategy’ in which she addressed a number of topics. First, she debated how she should present herself at dinner, deciding after listing pros and cons to play the role of a complete innocent from small-town Minnesota ... which would be relatively easy since she could be herself. Second, and going along with the first, she would dress very conservatively but attractively ... medium blue sweater, dark skirt to just above her knees, and low heels ... hair worn long and casual on her back. Third, she’d feign shyness and gullibility, but also show caution in the hope of prodding Winters to apply the full-court sales press, thereby offering Barb a complete, and hopefully incriminating, look at the recruitment process.

Satisfied, she tossed the legal pad on the bed and got up to dry her hair, apply light makeup, and get dressed. Satisfied with her appearance, she checked her phone and seeing that it was time to go, headed out to keep her appointment at the Campus Inn, which was about a ten minute walk from the dorm.

She arrived a bit early, but rather than go in she chose to linger outside for awhile, figuring that if Winters might be watching she would interpret the lingering as indecision and hesitation, which would play into Barb’s plan.

At 6:38 she went in, spoke to the hostess who nodded and led Barb into the dining area.

Off to one side, seated alone at a table set for two and, as Barb had expected, next to a window with a view of both the street outside and the street entrance to the restaurant, was an expensively dressed, quite attractive-looking brown-haired woman, who appeared at a distance to be in her late-20s or early-30s.


The woman spotted Barb immediately, flashed a dazzling smile and waved her over.
Barb seems supremely confident in herself - has she never read these tales before! The plot is building nicely...
 
CHAPTER EIGHT

From his office, he watched the helicopter descend slowly towards the landing pad, the blur of the rotors slowly resolving itself into individual blades before stopping. After a few moments, the hatch opened and two figures descended. One was Kelly and the other would have to be the new recruit, Barbara Moore. Kelly led her into the house and out of sight.

Even after all this time, the sight of a new recruit gave him a little thrill. Thinking of how they would find out that things here weren’t quite as Kelly had promised, what they were expected to do and the consequences of refusing or even resisting gave him a tingle in his groin.

Seeing their reaction the first time they watched someone being whipped or subjected to some other painful treatment, the first time they experienced it for themselves, the first time they were ordered to have sex with someone they would never have agreed to have anything to do with in their previous lives was a moment he savored.

He particularly liked when they were students at his alma mater, Pitcher College. Back when he had attended there, he had been a shy nerd, easily rejected by the few girls he had screwed up enough courage to ask out. He hadn’t done much better after graduating, working at a few places making a modest salary.

Then, he had started dipping his toe in the markets, studying the charts, reading the financial press, and found that he had an aptitude for picking winning strategies. As the few dollars he could spare doubled and then doubled again, he could take bigger risks and make bigger profits. Soon, he was doing that full time.

He could have found a woman and settled down like most people did. A man as wealthy as he could always find someone who’d be happy to marry them, even guys much less good-looking than he was. He’d even considered doing that with Kelly. But he knew he’d miss the thrill of seeing the expression on faces like Barbara Moore’s when what she had signed up for hit her.

And this would be very special because he would be sharing it with the Senator, who was also a Pitcher alum, though from a class a few years ahead of his. The Senator could only come down to Pirate Cay very occasionally because of his busy schedule and his fear of some nosy reporter digging into his comings and goings, but when he could make it down, he liked to play hard.

He had forwarded the photo of Barbara Moore that Kelly had taken to the Senator as soon as he’d had received it last night. The Senator had liked what he saw and would be arriving tomorrow bright and early.

In the meantime, he would let Kelly show the girl to her room and let her settle in. He’d see her in the flesh soon enough. First, it was time for a good workout and a shower.

***​

He sat back in his chair, clad only in a terry robe after his shower, staring out through the plate glass window at the palm-fringed beach and the blue-green sea beyond. He never got tired of that view.

There was a knock at the door. “Come in!” he said.

Kelly came in first. Behind her was Barbara. Kelly had dressed her conservatively, or at least conservatively for Pirate Cay, in a low cut T-shirt that covered most of her belly, showing just enough of her breasts to tantalize, shorts that went at least a few inches down her long, shapely legs, and flip-flops, nothing that would look too out of place at any of the beach resorts on the nearby islands.

Barbara stared, open mouthed, first at the view, then at him. She stopped, frozen in her tracks, but Kelly took her arm and led her firmly but gently towards the desk. “I’d like you to meet Barbara Moore.”

He stood, smiling warmly. She looked every bit as delectable as she had in the photo, only more so, clad in clothes that revealed more of her body than what she had worn to dinner with Kelly in the cold climes of Pitcher College.

“I’m very glad to meet you, Ms Moore,” he said, standing. “What do your friends call you? Barbara? Barb?”

“Uhh…Uhh...Barb,” she stammered, staring at him. The robe he wore covered his crotch, so he was decent, at least for the moment.

“Well, Barb, we’re all friends here, so that’s what I’ll call you if that’s OK.”

“Yes, sir, Barb is OK,” she replied, though it was clear she didn’t find the whole situation or his attire OK.

“Kelly, would you bring over a couple of chairs, please?” he asked. Kelly brought them and placed them in front of the desk. “Please, sit down.”

They sat, Barb, looking as though there might be a scorpion on the chair. He walked over and perched on the front of the desk, a few feet in front of them. “You’ll excuse the way I’m dressed, I hope. We’re very casual and open here on Pirate Cay and I just got out of the shower after my workout.” Barb looked down at the floor. “How was your flight down?”

She looked up. “It was very comfortable, sir.”

“Have you ever been on a private jet before?”

“No sir. It was much more luxurious than the airlines.”

He laughed. “Yes, they really pack them in like sardines these days, don’ they?” He continued, switching gears, “Kelly tells me you’re a freshman at Pitcher, majoring in business, is that right?”

“Yes, sir.”

“And how do you like it?”

“It’s fine, sir,” she replied. “The professors are good and I feel I’m learning a lot.”

“No doubt, you are, Barb. I went there as Kelly probably told you.” Barb nodded. “But I can assure you, you will learn more about business, how the world really works, here than you will there. Not that you shouldn’t go back and get the piece of paper.”

“That’s my plan, sir. I’m eager to learn.”

“That’s wonderful, Barb. You should be open to new experiences. That’s how you grow, both professionally and personally. I’m eager to teach you whatever you’re open to learning. I’ve done well in life as you can see and I like to give back.”

“Of course, I donate generously to many good causes, Pitcher being high on the list, but I like to also do so in a more personal way as well, by mentoring young people. Two of your fellow students, Tara Malone and Delia Ortiz, came down during spring break and enjoyed things so much that they have agreed to stay on for a while. I believe you know them.”

“I know both of them casually. We aren’t good friends or anything, but they were in my Psych class. I knew that if they came here, it must be a great place.”

He smiled. “You’re a very smart young woman, Barb. I can see that.” Barb smiled.

“Now, Kelly, I trust you’ve explained to Barb how things work down here on Pirate Cay. How the more she is willing to accommodate the needs of others, the more money she can make and the more mentoring she can benefit from.”

“Certainly,” Kelly replied, and, choosing her words carefully, she elaborated by saying, “We spoke about it generally at dinner and a bit on the plane down. Barb is aware that working hard and learning from you will please you greatly, and is something for which she can expect to be handsomely rewarded.”

“And, Barb, being a smart young woman, you want to get the most that you can from your time here, I should think.”

“Yes, sir, I do, but perhaps I need some time to get used to this place. This is all very new for me.”

“I understand perfectly. Many of your fellow students who come down here feel that way. That’s why we always start slowly and ease into things, right, Kelly.”

“Sure,” Kelly responded. “Absolutely.”

“Umm…that’s good, I guess,” Barb replied.

“So if I were to tell you that I’ve been occupied in some very important business and then a vigorous exercise session and could use some relaxation, what would you say, Barb?”

“Uh, I think you certainly should relax, then, sir. All work and no play makes Jack a dull boy, right?”

“Exactly. And since I sent my private plane for you and flew you down to this beautiful spot, surely you wouldn’t deny me a little help in relaxing.”

Barb looked taken aback. “I’m not sure I get what you mean, sir.”

“Like if I were to lie down on that massage table by the French doors and you were to give me a back rub. Just a nice back rub, like you’ve probably done with friends. That wouldn’t be too much to ask, would it?”

“Uhh, I really don’t think that’s appropriate. I suspect you’re naked under that robe and I really don’t think that’s something I’m prepared to do.”

He validated Barb’s suspicions by shifting his body so that the lower flaps of his robe drew open. He was semi-erect. Barb stared at him open-mouthed.

She started to stand. “Really! That isn’t what I came here to do. I’m sorry, but, no, I can’t. I mean, I won’t.”

He pulled the robe closed. “That’s fine, Barb, we’re all friends here and I considered that something that friends would do for each other. We’re very open about nudity and sex here, as you will see. None of those inhibitions that keep people back in the States from enjoying life.”

“But no one is forced here. Everyone is offered a choice. One can do what’s asked and be rewarded or refuse and see what happens. Think about it, Barb. It’s never too late to say ‘Yes’”.

Barb shook her head and turned towards the door.

“Kelly, why don’t you take Barb to see her classmates, Tara and Delia? The three of them can have a nice chat and they can explain things to Barb and she can think about what they have to say and maybe come back and see me later.” Kelly hurried towards the door to catch up with Barb.
 
CHAPTER EIGHT

From his office, he watched the helicopter descend slowly towards the landing pad, the blur of the rotors slowly resolving itself into individual blades before stopping. After a few moments, the hatch opened and two figures descended. One was Kelly and the other would have to be the new recruit, Barbara Moore. Kelly led her into the house and out of sight.

Even after all this time, the sight of a new recruit gave him a little thrill. Thinking of how they would find out that things here weren’t quite as Kelly had promised, what they were expected to do and the consequences of refusing or even resisting gave him a tingle in his groin.

Seeing their reaction the first time they watched someone being whipped or subjected to some other painful treatment, the first time they experienced it for themselves, the first time they were ordered to have sex with someone they would never have agreed to have anything to do with in their previous lives was a moment he savored.

He particularly liked when they were students at his alma mater, Pitcher College. Back when he had attended there, he had been a shy nerd, easily rejected by the few girls he had screwed up enough courage to ask out. He hadn’t done much better after graduating, working at a few places making a modest salary.

Then, he had started dipping his toe in the markets, studying the charts, reading the financial press, and found that he had an aptitude for picking winning strategies. As the few dollars he could spare doubled and then doubled again, he could take bigger risks and make bigger profits. Soon, he was doing that full time.

He could have found a woman and settled down like most people did. A man as wealthy as he could always find someone who’d be happy to marry them, even guys much less good-looking than he was. He’d even considered doing that with Kelly. But he knew he’d miss the thrill of seeing the expression on faces like Barbara Moore’s when what she had signed up for hit her.

And this would be very special because he would be sharing it with the Senator, who was also a Pitcher alum, though from a class a few years ahead of his. The Senator could only come down to Pirate Cay very occasionally because of his busy schedule and his fear of some nosy reporter digging into his comings and goings, but when he could make it down, he liked to play hard.

He had forwarded the photo of Barbara Moore that Kelly had taken to the Senator as soon as he’d had received it last night. The Senator had liked what he saw and would be arriving tomorrow bright and early.

In the meantime, he would let Kelly show the girl to her room and let her settle in. He’d see her in the flesh soon enough. First, it was time for a good workout and a shower.

***​

He sat back in his chair, clad only in a terry robe after his shower, staring out through the plate glass window at the palm-fringed beach and the blue-green sea beyond. He never got tired of that view.

There was a knock at the door. “Come in!” he said.

Kelly came in first. Behind her was Barbara. Kelly had dressed her conservatively, or at least conservatively for Pirate Cay, in a low cut T-shirt that covered most of her belly, showing just enough of her breasts to tantalize, shorts that went at least a few inches down her long, shapely legs, and flip-flops, nothing that would look too out of place at any of the beach resorts on the nearby islands.

Barbara stared, open mouthed, first at the view, then at him. She stopped, frozen in her tracks, but Kelly took her arm and led her firmly but gently towards the desk. “I’d like you to meet Barbara Moore.”

He stood, smiling warmly. She looked every bit as delectable as she had in the photo, only more so, clad in clothes that revealed more of her body than what she had worn to dinner with Kelly in the cold climes of Pitcher College.

“I’m very glad to meet you, Ms Moore,” he said, standing. “What do your friends call you? Barbara? Barb?”

“Uhh…Uhh...Barb,” she stammered, staring at him. The robe he wore covered his crotch, so he was decent, at least for the moment.

“Well, Barb, we’re all friends here, so that’s what I’ll call you if that’s OK.”

“Yes, sir, Barb is OK,” she replied, though it was clear she didn’t find the whole situation or his attire OK.

“Kelly, would you bring over a couple of chairs, please?” he asked. Kelly brought them and placed them in front of the desk. “Please, sit down.”

They sat, Barb, looking as though there might be a scorpion on the chair. He walked over and perched on the front of the desk, a few feet in front of them. “You’ll excuse the way I’m dressed, I hope. We’re very casual and open here on Pirate Cay and I just got out of the shower after my workout.” Barb looked down at the floor. “How was your flight down?”

She looked up. “It was very comfortable, sir.”

“Have you ever been on a private jet before?”

“No sir. It was much more luxurious than the airlines.”

He laughed. “Yes, they really pack them in like sardines these days, don’ they?” He continued, switching gears, “Kelly tells me you’re a freshman at Pitcher, majoring in business, is that right?”

“Yes, sir.”

“And how do you like it?”

“It’s fine, sir,” she replied. “The professors are good and I feel I’m learning a lot.”

“No doubt, you are, Barb. I went there as Kelly probably told you.” Barb nodded. “But I can assure you, you will learn more about business, how the world really works, here than you will there. Not that you shouldn’t go back and get the piece of paper.”

“That’s my plan, sir. I’m eager to learn.”

“That’s wonderful, Barb. You should be open to new experiences. That’s how you grow, both professionally and personally. I’m eager to teach you whatever you’re open to learning. I’ve done well in life as you can see and I like to give back.”

“Of course, I donate generously to many good causes, Pitcher being high on the list, but I like to also do so in a more personal way as well, by mentoring young people. Two of your fellow students, Tara Malone and Delia Ortiz, came down during spring break and enjoyed things so much that they have agreed to stay on for a while. I believe you know them.”

“I know both of them casually. We aren’t good friends or anything, but they were in my Psych class. I knew that if they came here, it must be a great place.”

He smiled. “You’re a very smart young woman, Barb. I can see that.” Barb smiled.

“Now, Kelly, I trust you’ve explained to Barb how things work down here on Pirate Cay. How the more she is willing to accommodate the needs of others, the more money she can make and the more mentoring she can benefit from.”

“Certainly,” Kelly replied, and, choosing her words carefully, she elaborated by saying, “We spoke about it generally at dinner and a bit on the plane down. Barb is aware that working hard and learning from you will please you greatly, and is something for which she can expect to be handsomely rewarded.”

“And, Barb, being a smart young woman, you want to get the most that you can from your time here, I should think.”

“Yes, sir, I do, but perhaps I need some time to get used to this place. This is all very new for me.”

“I understand perfectly. Many of your fellow students who come down here feel that way. That’s why we always start slowly and ease into things, right, Kelly.”

“Sure,” Kelly responded. “Absolutely.”

“Umm…that’s good, I guess,” Barb replied.

“So if I were to tell you that I’ve been occupied in some very important business and then a vigorous exercise session and could use some relaxation, what would you say, Barb?”

“Uh, I think you certainly should relax, then, sir. All work and no play makes Jack a dull boy, right?”

“Exactly. And since I sent my private plane for you and flew you down to this beautiful spot, surely you wouldn’t deny me a little help in relaxing.”

Barb looked taken aback. “I’m not sure I get what you mean, sir.”

“Like if I were to lie down on that massage table by the French doors and you were to give me a back rub. Just a nice back rub, like you’ve probably done with friends. That wouldn’t be too much to ask, would it?”

“Uhh, I really don’t think that’s appropriate. I suspect you’re naked under that robe and I really don’t think that’s something I’m prepared to do.”

He validated Barb’s suspicions by shifting his body so that the lower flaps of his robe drew open. He was semi-erect. Barb stared at him open-mouthed.

She started to stand. “Really! That isn’t what I came here to do. I’m sorry, but, no, I can’t. I mean, I won’t.”

He pulled the robe closed. “That’s fine, Barb, we’re all friends here and I considered that something that friends would do for each other. We’re very open about nudity and sex here, as you will see. None of those inhibitions that keep people back in the States from enjoying life.”

“But no one is forced here. Everyone is offered a choice. One can do what’s asked and be rewarded or refuse and see what happens. Think about it, Barb. It’s never too late to say ‘Yes’”.

Barb shook her head and turned towards the door.

“Kelly, why don’t you take Barb to see her classmates, Tara and Delia? The three of them can have a nice chat and they can explain things to Barb and she can think about what they have to say and maybe come back and see me later.” Kelly hurried towards the door to catch up with Barb.
"... I suspect you’re naked under that robe and I really don’t think that’s something I’m prepared to do ..." Oh dear Ms Moore, copy book already very blotted! Another great read Windy.
 
To our dear readers: Barb screwed up (as she often does) and omitted the last part of Chapter seven. For that act of sheer inexcusable incompetence she’ll undoubtedly pay a stiff price at the whipping post. But for you, our readers, kindly regard the following as a flashback and enjoy:

CHAPTER SEVEN POINT FIVE

Remembering the role she intended to play, Barb was purposely awkward as Kelly rose to greet her. She shook hands only tentatively and then knocked over a water glass when she quickly withdrew her hand, which forced she and Kelly to stand uncomfortably side-by-side while a waitress and busboy fussed over cleaning up the mess and resetting the table.

“Oh, I’m so terribly sorry!” Barb wailed.

“No, don’t be,” replied Kelly. “Those things happen.”

“Well, meeting you like this had made me so nervous. I mean this sounds like such a great opportunity. I want to learn more.”

“It is, Barb! But let’s sit down and order dinner before I fill you in, alright?”

“Yes, ma’am.”

“No, no. Call me Kelly.”

“Alright, I will.”

“So, choose anything you like on the menu. It’s all great food.”

“Okay, let’s see. I think I’d like to try the Chicken Kiev,” if that’s alright.

“Excellent choice, I’ll do the same. And I’ll order us glasses of wine.”

“Um, I’m only nineteen.”

“Don’t worry about it, I’ll take responsibility,” said Kelly, blithely pointing to an item on the wine list held by the waitress.

“Okay ... I guess.”

“Of course it is. Now, let me fill you in on this golden opportunity while we are waiting for our drinks. My employer is a very wealthy man. Wealthy beyond anything you can imagine or what I could have imagined when I was a young student like you. He’s also brilliant. He started out with nothing and made a fortune by coming up with investment strategies that even the best minds on Wall Street couldn’t match.”

“Wow, he must really be brilliant.”

“He is, Barb. And what’s more, he likes to associate with bright young people like you. He likes to know what you think about and like to do. ‘It’s my way of staying in touch with the future, Kelly,’ he likes to say to me. He’s also an alumnus of Pitcher and he gives generously to the school, so it’s natural that he sends me here to look for bright young people he can help. He understands how hard it can be to be poor among so many of your fellow students who are so much better off.”

“That’s so noble of him!”

“Yes, he’s remarkable. But look, here’s our wine. Let’s toast to the exciting prospect of you getting to know him.”

Barb took a sip, and made a face.

“Sorry, I am not much of a drinker.”

“You’re young. Take it slow and give it a chance. It’s an excellent wine.”

“I’m sure it is. I’m just nervous. So tell me ... uh ... Kelly ... who exactly is he, and how do I get to meet him, and what will he expect of me?”

“He lives in Providencia. It’s a small country in the Caribbean. Two larger islands and a number of smaller ones. He owns one of the smaller ones, an island called Pirate Cay. He’s there now and that’s where you would go.”

“So I would have to travel there?”

“Ah, here come our salads,” Kelly announced, seeing the waitress headed their way.”

While they ate, Kelly pulled her phone out of her purse. “Let me show you where you’d be going.” There was an aerial view of a lush tropical island. “You can just see the house over there,” she pointed at a large structure along the shore that was surrounded by several smaller structures. The outbuildings are where staff stays-cooks, gardeners, and such. And here’s a photo of a bedroom like the one you might occupy as a Companion.”

“Companion? What exactly does that mean. Seems a strange word?”

“Ah, our entrees are here,” Kelly announced. She put her phone down. “Let’s eat and I’ll continue when we’re finished.”

They ate in silence for several minutes. Barb figured Kelly was stalling while she figured out exactly how to define ‘Companion’.

Setting her fork down, Kelly leaned forward, a look of kindly earnestness on her face. “Yes, the word ‘Companion’ can be misleading. A more appropriate word might be ‘Mentee’. He’s a brilliant man and knows a lot about the world. He can teach you how to live, how to succeed, to have some self discipline, something many young people nowadays lack, especially those who come from modest means, like yourself. You’ve heard of ‘paying it forward’, right? Well, it’s through bright earnest young people like you, Barb, that he likes to pay it forward.”

“So, assuming I’d like to meet him, from what I gather the only option would be to go down there. Is that right?”

“Yes, he rarely leaves the island. And you’d have to be there for at least a month, maybe two.”

“Then, when would this be? The semester here at Pitcher has resumed now that Spring Break is over, and I have a full load of classes.”

“I’m afraid it would have to be right away ... as soon as you can get a passport if you don’t have one and travel arrangements can be made.”

“I have a passport, but what about my classes?”

“That can be taken care of. He is a Pitcher alumnus and gives generously to the Pitcher Foundation in addition to all kinds of campus initiatives. Most recently he funded the construction of the College’s new state-of-the-art dormitory.”

“Wow. That’s where I live.”

“There you go ... look, he prefers to keep his name out of the limelight, but the College knows who he is, and we can easily make the necessary arrangements, through the Pitcher Dean of Students Office, to engineer a ‘workaround’ for your spring semester classes. We’ve done that for Pitcher students in the past.”

Barb was tempted to tell her that, just that very morning, Dean Carter had disavowed any knowledge of the ad, or of Delia and Tara, but she bit her tongue and slyly asked instead, “If other Pitcher students have done this in the past, I wonder if I might be able to talk to them to find out how the experience was for them?”

Watching closely over her wine glass as she emptied it, Barb was sure she noted a fleeting look of discomfort cross Kelly’s face before she said, “Yes, but I’m afraid that’s not possible as my employer’s need for privacy in all his affairs requires that the identities of the beneficiaries of his generous gifts must remain closely guarded secrets. You’ll be asked to honor this need for confidentiality as well.”

“I see.”

“But let me get to the best part,” continued Kelly, brightening up. “If you agree to go down there, he’ll arrange with the College to grant you a full scholarship. I mean the real thing ... no loans, no work-study. He gives the College plenty of money, after all, including a big chunk of its scholarship endowment funds. And you’ll walk away with a check for $ 20,000 for your time. He’s a very generous man, Barb. If he’s pleased with you, you could walk out with as much as $100,000 as well as references that can open doors for you beyond your wildest imagination.

“This is unbelievable,” cried Barb, doing her best to look starry-eyed. “But what exactly will I have to do for him in return?”

“Keep him company, Barb. Make him happy. Learn from him. He’s worked very hard to get where he is and wants to share with someone like you. In return, he just wants your companionship. He deserves some relaxation.

“There’s that word “companion ‘ again. That doesn’t mean sex, does it?”

“It means make him happy within the limits of whatever you are comfortable with. No one is going to force you. There are no expectations. Just going there will earn you a good payday. And the happier you make him, the more you will come home with. And besides, you’ll have the run of the place. It’s an island paradise and you wouldn’t believe the amenities ... beaches, azure waters, tennis courts, entertainments, fabulous food, expensive clothing, everything you can imagine and more.”

“Well, it does sound intriguing.”

“Believe me, you won’t regret doing it. I was young and broke like you ten years ago when I went to work for him as a Companion. It changed my life. I live well, better than I had ever dreamed of. I’ve worked for him ever since.”

“Well, I guess you’re living proof, Kelly.”

“I am. Now how about dessert? Their triple chocolate cake is to die for!”

“No, thank you. Sounds yummy but I’m stuffed.”

“Well, good. So am I, Barb ... now look, there’s a lot to think about, but time is short and I will need an answer by 9 am tomorrow morning, and you have my phone number. I really hope you decide to come. Now that I have met you, I’m certain that we’ll get along great together and I know him well enough to be very confident that he’ll like you.”

“Okay. I will I’ll need to mention this to my parents, of course, but I can call them tonight. I’m sure they’ll be thrilled and I am definitely very interested.”


“Great. Listen, before you go, let’s get a pic of the two of us,” Kelly said, motioning the waitress over. “Would you mind?” she asked, handing her the phone and pulling Barb to stand on one side of her. The flash lit up the room.
 
To our dear readers: Barb screwed up (as she often does) and omitted the last part of Chapter seven. For that act of sheer inexcusable incompetence she’ll undoubtedly pay a stiff price at the whipping post. But for you, our readers, kindly regard the following as a flashback and enjoy:
Well, now I'm torn. In business, when you screw up, you are supposed to admit it and correct the error. You have done that, so our billionaire should laud you for having done the right thing. On the other hand, you didn't give him his "back rub" (to be administered, oddly enough on his front:confused::rolleyes::popcorn:) so he's not entirely pleased. But I'm sure you'll come around like the smart young student that you are.;)

PS-I failed to notice Barb's mistake, so I may have to join her at the post:eek:
 
To our dear readers: Barb screwed up (as she often does) and omitted the last part of Chapter seven. For that act of sheer inexcusable incompetence she’ll undoubtedly pay a stiff price at the whipping post. But for you, our readers, kindly regard the following as a flashback and enjoy:

CHAPTER SEVEN POINT FIVE

Remembering the role she intended to play, Barb was purposely awkward as Kelly rose to greet her. She shook hands only tentatively and then knocked over a water glass when she quickly withdrew her hand, which forced she and Kelly to stand uncomfortably side-by-side while a waitress and busboy fussed over cleaning up the mess and resetting the table.

“Oh, I’m so terribly sorry!” Barb wailed.

“No, don’t be,” replied Kelly. “Those things happen.”

“Well, meeting you like this had made me so nervous. I mean this sounds like such a great opportunity. I want to learn more.”

“It is, Barb! But let’s sit down and order dinner before I fill you in, alright?”

“Yes, ma’am.”

“No, no. Call me Kelly.”

“Alright, I will.”

“So, choose anything you like on the menu. It’s all great food.”

“Okay, let’s see. I think I’d like to try the Chicken Kiev,” if that’s alright.

“Excellent choice, I’ll do the same. And I’ll order us glasses of wine.”

“Um, I’m only nineteen.”

“Don’t worry about it, I’ll take responsibility,” said Kelly, blithely pointing to an item on the wine list held by the waitress.

“Okay ... I guess.”

“Of course it is. Now, let me fill you in on this golden opportunity while we are waiting for our drinks. My employer is a very wealthy man. Wealthy beyond anything you can imagine or what I could have imagined when I was a young student like you. He’s also brilliant. He started out with nothing and made a fortune by coming up with investment strategies that even the best minds on Wall Street couldn’t match.”

“Wow, he must really be brilliant.”

“He is, Barb. And what’s more, he likes to associate with bright young people like you. He likes to know what you think about and like to do. ‘It’s my way of staying in touch with the future, Kelly,’ he likes to say to me. He’s also an alumnus of Pitcher and he gives generously to the school, so it’s natural that he sends me here to look for bright young people he can help. He understands how hard it can be to be poor among so many of your fellow students who are so much better off.”

“That’s so noble of him!”

“Yes, he’s remarkable. But look, here’s our wine. Let’s toast to the exciting prospect of you getting to know him.”

Barb took a sip, and made a face.

“Sorry, I am not much of a drinker.”

“You’re young. Take it slow and give it a chance. It’s an excellent wine.”

“I’m sure it is. I’m just nervous. So tell me ... uh ... Kelly ... who exactly is he, and how do I get to meet him, and what will he expect of me?”

“He lives in Providencia. It’s a small country in the Caribbean. Two larger islands and a number of smaller ones. He owns one of the smaller ones, an island called Pirate Cay. He’s there now and that’s where you would go.”

“So I would have to travel there?”

“Ah, here come our salads,” Kelly announced, seeing the waitress headed their way.”

While they ate, Kelly pulled her phone out of her purse. “Let me show you where you’d be going.” There was an aerial view of a lush tropical island. “You can just see the house over there,” she pointed at a large structure along the shore that was surrounded by several smaller structures. The outbuildings are where staff stays-cooks, gardeners, and such. And here’s a photo of a bedroom like the one you might occupy as a Companion.”

“Companion? What exactly does that mean. Seems a strange word?”

“Ah, our entrees are here,” Kelly announced. She put her phone down. “Let’s eat and I’ll continue when we’re finished.”

They ate in silence for several minutes. Barb figured Kelly was stalling while she figured out exactly how to define ‘Companion’.

Setting her fork down, Kelly leaned forward, a look of kindly earnestness on her face. “Yes, the word ‘Companion’ can be misleading. A more appropriate word might be ‘Mentee’. He’s a brilliant man and knows a lot about the world. He can teach you how to live, how to succeed, to have some self discipline, something many young people nowadays lack, especially those who come from modest means, like yourself. You’ve heard of ‘paying it forward’, right? Well, it’s through bright earnest young people like you, Barb, that he likes to pay it forward.”

“So, assuming I’d like to meet him, from what I gather the only option would be to go down there. Is that right?”

“Yes, he rarely leaves the island. And you’d have to be there for at least a month, maybe two.”

“Then, when would this be? The semester here at Pitcher has resumed now that Spring Break is over, and I have a full load of classes.”

“I’m afraid it would have to be right away ... as soon as you can get a passport if you don’t have one and travel arrangements can be made.”

“I have a passport, but what about my classes?”

“That can be taken care of. He is a Pitcher alumnus and gives generously to the Pitcher Foundation in addition to all kinds of campus initiatives. Most recently he funded the construction of the College’s new state-of-the-art dormitory.”

“Wow. That’s where I live.”

“There you go ... look, he prefers to keep his name out of the limelight, but the College knows who he is, and we can easily make the necessary arrangements, through the Pitcher Dean of Students Office, to engineer a ‘workaround’ for your spring semester classes. We’ve done that for Pitcher students in the past.”

Barb was tempted to tell her that, just that very morning, Dean Carter had disavowed any knowledge of the ad, or of Delia and Tara, but she bit her tongue and slyly asked instead, “If other Pitcher students have done this in the past, I wonder if I might be able to talk to them to find out how the experience was for them?”

Watching closely over her wine glass as she emptied it, Barb was sure she noted a fleeting look of discomfort cross Kelly’s face before she said, “Yes, but I’m afraid that’s not possible as my employer’s need for privacy in all his affairs requires that the identities of the beneficiaries of his generous gifts must remain closely guarded secrets. You’ll be asked to honor this need for confidentiality as well.”

“I see.”

“But let me get to the best part,” continued Kelly, brightening up. “If you agree to go down there, he’ll arrange with the College to grant you a full scholarship. I mean the real thing ... no loans, no work-study. He gives the College plenty of money, after all, including a big chunk of its scholarship endowment funds. And you’ll walk away with a check for $ 20,000 for your time. He’s a very generous man, Barb. If he’s pleased with you, you could walk out with as much as $100,000 as well as references that can open doors for you beyond your wildest imagination.

“This is unbelievable,” cried Barb, doing her best to look starry-eyed. “But what exactly will I have to do for him in return?”

“Keep him company, Barb. Make him happy. Learn from him. He’s worked very hard to get where he is and wants to share with someone like you. In return, he just wants your companionship. He deserves some relaxation.

“There’s that word “companion ‘ again. That doesn’t mean sex, does it?”

“It means make him happy within the limits of whatever you are comfortable with. No one is going to force you. There are no expectations. Just going there will earn you a good payday. And the happier you make him, the more you will come home with. And besides, you’ll have the run of the place. It’s an island paradise and you wouldn’t believe the amenities ... beaches, azure waters, tennis courts, entertainments, fabulous food, expensive clothing, everything you can imagine and more.”

“Well, it does sound intriguing.”

“Believe me, you won’t regret doing it. I was young and broke like you ten years ago when I went to work for him as a Companion. It changed my life. I live well, better than I had ever dreamed of. I’ve worked for him ever since.”

“Well, I guess you’re living proof, Kelly.”

“I am. Now how about dessert? Their triple chocolate cake is to die for!”

“No, thank you. Sounds yummy but I’m stuffed.”

“Well, good. So am I, Barb ... now look, there’s a lot to think about, but time is short and I will need an answer by 9 am tomorrow morning, and you have my phone number. I really hope you decide to come. Now that I have met you, I’m certain that we’ll get along great together and I know him well enough to be very confident that he’ll like you.”

“Okay. I will I’ll need to mention this to my parents, of course, but I can call them tonight. I’m sure they’ll be thrilled and I am definitely very interested.”


“Great. Listen, before you go, let’s get a pic of the two of us,” Kelly said, motioning the waitress over. “Would you mind?” she asked, handing her the phone and pulling Barb to stand on one side of her. The flash lit up the room.
"...Their triple chocolate cake is to die for! ..." - A potentially prophetic statement ... Barb did well to refuse it ...
 
CHAPTER NINE

As Kelly escorted Barb along a long corridor which she explained led to the living quarters for the Companions and where they would find the other two resident Companions, Delia and Tara, Barb’s mind was spinning.

“Ummm...” she said, turning towards Kelly to block any further progress along the corridor, “Excuse me, but I have to tell you that I was quite taken aback by what just happened back there. I mean ... you know ... the way he exposed himself right in front of me!”

“Oh, please don’t think anything of that, Barb. Like he said, things are very casual down here. This is the Caribbean, not upstate New York, and certainly not Minnesota. We’re all adults here. No one pays any attention, really.”

“Well maybe so, but I thought it both strange and disgusting. And, I have no intention of being his masseuse. And another thing, Kelly, I still haven’t gotten a straight answer to the meaning of this term, ‘Companion’, which keeps being thrown around. I’m beginning to wonder whether you’ve been straight with me. From what he said back there, it sure sounded like he expected things to get ... uh ... physical.”

“No, Barb. You haven’t been misled. I told you when you raised it at dinner back at The Campus Inn, and you heard it said again just minutes ago ... nothing here is forced. You are free to work with him in any way you feel comfortable.”

“Yes, I got that ... but there have been implications made, haven’t there? I mean ... um ... how did he put it ... um ... I think his exact words were: ‘One can do what’s asked and be rewarded or refuse and see what happens. Think about it, Barb. It’s never too late to say 'Yes’.”

“What’s your point, Barb?”

“My point is that ‘refuse and see what happens’ has what I would call an ominously threatening ring to it! And another question, Kelly ... why is he always referred to as ‘he’ or ‘him’. The man does have a real name, doesn’t he?”

“Barb, the trip down here was a long one, and it’s understandable that you’re feeling tired and stressed, but I can assure you that everything is just fine. You’re taking things all wrong. Now let’s find your friends from Pitcher and get you some relaxation so that you can unwind. Oh, here now, as a matter of fact, is the room they share together. Let’s see if they’re in.”

Without knocking, Kelly threw open the door and ushered Barb in, singing out cheerily, “Hey, girls, I’ve got a surprise for you ... an old friend from Pitcher College!”

Two young women, wearing black string bikinis and just about to step out through the room’s sliding glass doors, spun around in surprise.

“Delia and Tara, this is Barb Moore. You two remember her, right? Barb tells me you were all together in a fall semester Psych class at Pitcher.”

“Uh ... oh yeah ... I remember you,” said Tara, “You used to sit in back and never said much, right?”

“Yeah, that would be me, alright,” grinned Barb sheepishly. “The class was pretty boring and too early in the morning.’

“Right about that, and welcome to Pirate Cay,” giggled Delia. “I take it Kelly here must have recruited you, like she did us.”

“Uh-Huh. But it looks like you two were just leaving. I shouldn’t hold you up.”

“No, we were only going out to lie on the beach. There’s a lovely breeze off the water and it’s the best time of the day to work on one’s tan. You’re welcome to join us if you like. After a long bleak winter hanging around Pitcher, I’m sure you could use some sun.

“Well, thanks, but I’ve just arrived and haven’t even had a chance to unpack yet. And my swimsuit is buried somewhere in my bags. You two go ahead and enjoy the beach.”

“Nonsense,” intervened Kelly. “As Delia and Tara will tell you, he takes pleasure in providing all his Companions with nothing but the highest quality fashions. I’ll run and grab you something off the rack!”

Delia laughed and Tara rolled her eyes as Kelly vanished. Barb took a close look at the string bikinis worn by the two girls, which in her estimation were definitely on the skimpy side. In fact, she wondered how Delia managed to keep her quite sizable boobs from getting away.

“Shhhh. Don’t say anything,” joked Tara. “She’ll be back before we know it.”

Moments later, Kelly returned, bearing a fistful of white string connected to some rather minuscule scraps of fabric.

“Thanks, Kelly, but I can’t wear that,” said Barb.

“Oh but you must,” gushed Kelly. “You’ll look smashing in it, Barb. So, come on. Go ahead and try it on so we can all see.”

“Oh, alright,” sighed Barb. “Where can I go to change?”

“Right here is fine. We’re all girls,” laughed Kelly.

“Just imagine you're back in the old dorm at Pitcher,” giggled Delia.

So, Barb laid the string out on a nearby bed, top then bottom, and turning her back on the others, she slipped her tee off over head, undid her bra and laid them on the bed. Then she wiggled out of her shorts and panties before attempting to don the string.

“Let me give you a hand, Barb” cooed Kelly, moving in before getting an answer.

Minutes later, after a bit of fussing, she spun Barb around to present to the others, announcing, “Tah dah!”

Barb blushed, acutely aware that the three tiny triangles of fabric, while artfully positioned, left her all but naked.

“You look great, Barb,” enthused Delia.

“For sure!” agreed Tara. “Come on, let’s go. Are you going to join us, Kelly?”

“No, no. Duty calls. He’s expecting me back in his office. There are things to which he wants me to attend. You girls go right ahead. Have fun and enjoy getting reacquainted.”

And with that the trio headed out across the perfectly manicured verdant lawn, headed for the sandy Caribbean beach at the foot of a gentle slope. And when they got there Delia rounded up three chaise lounges which she, with Tara’s help, lined up side-by-side. Tara then spread beach towels, which she had fetched from a nearby locker, across each of them, and tossed a tube of sunscreen on each.

“Last one in is a rotten egg!” laughed Delia, and all three ran to the water, waded in, and took the plunge. The water was warm, like in a bathtub.

A quarter of an hour later they returned to the chaises to stretch out under the sun, but not before taking turns applying sun screen to one another, interspersed with good spirited joking and laughing.

Eventually they settled down, stretched out on their tummies, the back strings on their tops undone, with Barb in the middle flanked on either side by the other two.

“Okay, you guys,” said Barb after a period of silence. “Tell me who ‘he’ really is. Why so mysterious?”

“We would if we knew,” said Tara. “But we’ve never actually been told.”

“Well ... let me tell you ... when Kelly took me to see him in his office a while ago, he exposed himself ... right in front of me! I couldn’t believe it! That’s not something that happens here often, I hope!”

“Oh, dear girl,” cried Delia, turning over on her back, tossing her top aside, reaching for the sunscreen and rubbing a handful on her breasts, “You have a lot to learn about this place and what goes on here!”

“I do?”

“You do,” said Tara, sitting up and going topless too. “We can tell you a lot, if you want to hear it?”

“Please,” replied Barb, turning over herself, but making no move to remove her top, self-consciously preferring to remain covered.

“Well,” began Delia, and was about to go on when the long dark shadow of a man suddenly passed over them.

“You two are late for your workout session at the gym!” growled the newcomer, a rather fit and very muscular looking character with what Barb thought was a head too small for his body.

“Oh, forgot all about it!” said Delia, making a show of pretending to smack her head with her hand.

“Barb, meet Robert. Robert this is Barb,” said Tara quickly and adding, “Robert is the fitness trainer here.’

“Pleased to meet you, Robert,” responded Barb with a half-smile.

“Likewise," he said, eyeing her up and down, she thought with a look in his eyes that put her off on him. “These girls need to go the gym with me now. Want to come along?”

“No, but thanks. I’ve just arrived here and am weary after a very long trip. I think I’ll just go to my room now and rest.”

“Suit yourself, come on girls.”

And with that Delia and Tara got up and followed him off, without even bothering to put their tops back on.

Barb went her own way, returning to the big house. Thinking that she would need a key to get into her room. she remembered that Kelly had said she had work to do with him in his office, so she went there and rapped gently on the door,

From inside she heard Kelly’s voice telling her to come in.

She opened the door to enter and was about to explain her mission, when she was stopped in her tracks by the sight of him stretched out naked on a portable table with Kelly leaning over him and massaging his back. She was wearing nothing but a black thong.

“Oh my God. Excuse me!” cried Barb, starting to backpedal out the door,

“No, it’s quite alright. Come on in Barb,” he said, turning over on his side to face her. “Kelly here was just giving me that massage I mentioned to you earlier. You’re more than welcome to assist her, or even take her place if you’d like. And I see you’ve come appropriately dressed for it too. I always like my masseuses to be bare-breasted though, so you’ll have to ditch the top.”

“N ... no ... I mean ... uh ... no thanks. I just dropped by to ... uh ... see about getting a key to my room. I am very weary and I thought I’d rest up a bit,”

“Barb, none of the rooms here have locks on the doors. Your room is the one across the hall from the one shared by Delia and Tara,” said Kelly evenly.

“Oh, I see ... well then .., I‘ll leave you to ... I mean ... well. I’ll go now.”

“Sure you don’t want to stay?” he said, raising his eyebrows,

“No thank you. I’d rather not.”

“Pity. I would have liked to have seen you without that top.”

She backed out quickly, closed the door, and fled.

And after she had left, he said to Kelly as she resumed massaging his back, “You don’t think she could possibly be a virgin do you? Where did you say she was from ... wasn’t it someplace in Minnesota?”

"That's right. She could be rather naive. She even said that she wanted to check with her parents before giving me an answer.

In the meantime, Barb located her room. Inside she found her bags resting on the floor by the far wall. Rummaging through the contents of the smaller bag she pulled out her legal pad and pen. Then she went over to the bed, stretched out on her tummy, flipped the pad to its second page, and began to write under a new heading, that read ‘Day One: First Impressions’:

1. Met the man, whoever he is. They never mention his name. Very strange.

2. it’s pretty obvious that what ‘Companion’ really means is ‘sex toy’. They claim that anything that happens here of that nature is entirely voluntary. Yet there is an implied threat that there may be consequences for non-compliance.

3, Kelly is not to be trusted.

4. Delia and Tara are here. Their whereabouts is no longer a mystery. Why they are still here is a mystery.

5. I might have found out if it weren’t for Robert the ‘trainer’. I don’t like him.
 
This is the Caribbean, not upstate New York, and certainly not Minnesota.
It's too frickin cold to expose yourself there!
I’m beginning to wonder whether you’ve been straight with me.
Really? You think?
My point is that ‘refuse and see what happens’ has what I would call an ominously threatening ring to it!
Stop being paranoid, Moore...
The man does have a real name, doesn’t he?”
Please allow me to introduce myself
I'm a man of wealth and taste

You used to sit in back and never said much, right?”

“Yeah, that would be me, alright,” grinned Barb sheepishly.
No, you must be mistaken. She complained non-stop...
“Let me give you a hand, Barb” cooed Kelly, moving in before getting an answer.
Very helpful. You see, it's all good.
 
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