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Spring Break Slaves 2: Reporting from Pirate Cay
- Thread starter windar
- Start date
M
montycrusto
Guest
I guess she's a virgin no moore,
Got deflowered by a fat senator.
But I'm willing to bet
It's not over yet;
Barb's other holes will come to the fore..
Got deflowered by a fat senator.
But I'm willing to bet
It's not over yet;
Barb's other holes will come to the fore..
Jackie1111
Tribune
Whips and chains make Barb mad
A cock at her lips makes her sad
In misery she will wallow
If she is forced to swallow
I personally wouldn't think it's so bad
A cock at her lips makes her sad
In misery she will wallow
If she is forced to swallow
I personally wouldn't think it's so bad
windar
Teller of Tales
Jackie's a very wise girlWhips and chains make Barb mad
A cock at her lips makes her sad
In misery she will wallow
If she is forced to swallow
I personally wouldn't think it's so bad
She's willing to give it a whirl
But Barb will not deign
Despite all the pain
Her tongue round the cockhead to swirl
CHAPTER SEVENTEEN
Barb woke with a start. Reaching for her iPhone, she checked the time ... 7:13 it read on the multicolored screen.
She felt disoriented and it took a few seconds to clear her mind and realize that she was in her ‘Companion’ room. She was lying naked on her bed, and must have fallen asleep from exhaustion there the night before. Her legal pad lay nearby, still open to the notations she had entered. Picking up the pad, and rubbing the sleep from her eyes, she read:
'Sensational scoop - Pulitzer Prize?"
1. Find out the identity of the 'Senator'. Make him pay for this with a forced resignation!
2. Get in-depth interviews with Delia and Tara. Get their 'stories' for depth and color.
3. Avoid any further whippings or worse, if possible (unlikely, but worth a try).
4. Sleuth out whether there is a way to somehow get off this friggin' island, preferably before Robert gets an opportunity to inflict permanent damage.
5. If and when I ever get back to Pitcher, investigate Dean Carter. He's got to be involved in this!
The shame and utter humiliation of the previous evening’s events came rushing back. She recalled with distaste how she had been compelled by Kelly, backed up by Robert, ‘the enforcer’, to give herself up for the ‘very first time’ to the likes of that pig of a Senator. Not the way she had ever imagined it happening!
That coupled with the realization that things would likely get worse for her before they got better if she didn’t come up with a sure-fire way to get off the island soon was more than she was prepared to face that morning. She felt like crying.
But ... on the other hand, the bullet points on the legal pad page also reminded her of the work to be done ... and the glory to be won if she could manage to hold fast to the investigative mission that had brought her to Pirate Cay! She may have been hoodwinked and debased, but she could still turn the tables and win in the end if she played her cards right.
“Yes, I can!” she said to herself out loud.
She had set her legal pad down and was just about to go get a shower when she heard the now familiar metallic clunk made by the externally controlled locking mechanism within the bedroom door. The door swung open and in waltzed Kelly, dressed in tee-shirt, shorts and flip flops, and sporting a big happy smile.
“Morning Barb,” she chirped breezily.
“Don’t you believe in knocking?” sniped Barb irritably.
“Oh, come on. Brighten up. It’s a beautiful morning. We should go for a nice swim together.”
“I’d prefer to be just left alone this morning, if you don’t mind.”
“What’s the matter, Barb. Still sore about having to let the Senator deflower you last night?”
“I was, for all practical purposes, raped.”
“No, you weren’t, Barb. You climbed onto that coffee table and rode him. I saw you do it with my own eyes. A pro couldn’t have done a better job of getting him off.”
“Under coercion, Kelly! You know friggin’ well, it was under coercion ... extreme coercion, I might add. One can get herself whipped around here for not playing along, and I’m not happy about it at all. Now, do me a favor and kindly leave my room.”
“His room, Barb ... not your room ... HIS room. You signed a contract. You’re here to serve him and that means everything, or else.”
Barb snorted derisively and turned her back on Kelly.
“Hey, Barb. What’s this?” said Kelly, frowning and reaching for the legal pad lying at the edge of the bed.
“That’s mine and it’s private,” cried Barb, her face showing alarm as she snatched it away and held it to her chest.
“Okay, sure Barb. I was just curious. Look, we got off on the wrong foot here. Let’s rewind and start over. How about that swim?”
“Okay, why not?” relented Barb as she stooped to slip the legal pad into her bag and zip it shut. “I’ll need to get something to wear.”
“Oh, no need for that. We’ll take a nice little dip in the nude. There’s no one around and even if there were, this is Pirate Cay. Everything here is private and uninhibited. He likes it that way. And the water’s so warm and nice. I do it in the nude all the time.”
“Well, okay.”
“Great, come on then,” chirped Kelly taking Barb by the hand, and leading her out into the corridor. Together they proceeded to the double glass doors at corridor’s end and out onto the dewy grass, the azure waters beckoning but a short distance away.
When they reached the water’s edge, Barb ventured a toe to test the temp while Kelly stripped away her tee and shorts and tossed them aside. She flashed Barb a smile, took her again by the hand and led her into the water.
Wading out until the water was nearly chest high, Barb marveled aloud about how clear it was. “Look, I can see some cute little fishies down there,” she exclaimed with almost child-like glee.
“Yes, the Caribbean is remarkable,” smiled Kelly. “Look over there, Barb, that’s his yacht moored to that buoy. Why don’t we swim over there and sun ourselves on its deck?”
“Is the water deep there? I mean over my head? Because if it is I can’t. I don’t know how to swim.”
“Well, I suspect it is. We can just stay here, if you’d rather, Barb. You’re really lovely, you know?” cooed Kelly, turning to Barb and embracing her in a hug that drew their bodies closer together frontally.
“Well, I do try to stay in shape,” replied Barb, attempting to back away.
“No, you really are quite lovely, Barb,” insisted Kelly brushing her open hands across Barb’s erect nipples and then gently cupping and lifting both breasts.
“Uh, Kelly,” said Barb backing further away. “We’re really not close friends ... I mean, not THAT kind of close friends.”
“Ummmm,” replied Kelly, slipping herself deftly around behind Barb to nibble at one side of her neck.
“Kelly! Stop!”
“Why?”
“Because ... uh ... I’m not into that kinda thing.”
“Really, Barb! What do you do? You were a virgin until last night. You don’t give head. You can’t swim. You obviously aren’t much of a drinker. And now, you’re telling me you’ve never done it with another girl? You did live in a women’s freshman Pitcher College dorm, right? What did you think was going on at night? You’re telling me you never ... “
“Well, I am what I am and what’s it to you anyway? I just ...”
Kelly cut her off by turning her about, bringing them face to face and kissing Barb hard on the mouth. And before Barb could break free, she reached down for her pussy, probing expertly with her fingers.
“Mmphhhhh” uttered Barb, the only sound she could make as she was overcome by the sheer force and passion of Kelly’s full-mouth kiss, and the tingling sensation of Kelly’s finger pressing firmly against and rubbing her clit.
Then she gasped as Kelly’s quick hot butterfly kisses moved inexorably from Barb’s mouth to her neck and shoulders and down to her breasts and nipples. And as Kelly slipped one, then two, then three fingers in, curling them slightly and moving them in and out with rapid strokes, what remained of Barb’s resistance began to evaporate. She began to moan ... a soft guttural moan ... as her body relaxed and began to rock forward and backward in the water in rhythmic response to Kelly’s stroking fingers. Releasing a nipple, Kelly’s mouth retraced it’s meandering path in reverse until she was kissing Barb again on the mouth, receiving this time a far more welcoming, open-mouthed response.
They remained locked together like that for several minutes before Barb’s hand sought out Kelly’s pussy, tentatively at first but then rushing to reciprocate.
*************
High on the balcony that overlooked the shore, the Senator felt a tap on his shoulder.
“Something interesting going on out there, Senator!”
“There sure is,” grinned the Senator, removing the binoculars from his eyes and handing them over to his host.
“Seems your assistant, Kelly, is doing an admirable job of carrying out your orders.”
“Giving our innocent one some pointers, is she?” he laughed as he focused the binoculars on the pair in the water.
“You do remember what you promised me last night, I hope?”
“Of course, I do, Senator. The afternoon’s activities will be most memorable. I guarantee it.
“Hand me those binoculars again.”
“Sure thing, Senator.
**************
Kelly reclined on her side, head cradled on her hand, gently tracing little circles on the pebbled pink aureole surrounding one of Barb nipples.
“You actually enjoyed that, out there in the water, now didn’t you?” she said softly. “Felt good didn’t it.”
Barb stretched lazily on the sand where they lay at the water’s edge and murmured, “I guess I probably did.”
“Probably? Only probably, Barb?”
“Well ... what I mean is ... well, it probably wasn’t right.”
“Oh, of course it was right, Barb. Don’t kid yourself. It was hot, and you loved it!”
“Well, maybe so, but ...”
“No, give it time. You’ll see. This place opens new vistas. That’s what Delia and Tara came to accept. And you will too.”
“I really doubt it.”
“And that, by the way brings up something else that I need to say to you.”
“What’s that, Kelly?”
“Well it’s about the Senator. Do you remember what he wanted you to do for him and you refused?”
“Yes. How could I forget. Disgusting!”
“Well, I’ve been told he wants to give you another chance.”
“Oh no! Never!” exclaimed Barb, sitting up suddenly. “There’s a limit beyond which I refuse to go!”
“Barb! Be reasonable. Refusal can be costly. You’ve learned that already. They’re capable of anything.”
“And you’re one of them. Kelly. You’re an enabler.”
“No Barb, I’m your friend and protector. You need to trust in me. I know it can look bad, but I’m really on your side. Take my advice and you’ll walk out of here one day when you’re contract expires.”
“And you’re advice is to go along with whatever they demand?”
“Essentially, yes, but with my guidance. I can and will protect you from the worst, Barb. I really will.”
“Thanks. I do believe you may be sincere in that, But I’ll make my own judgements. And right now my judgement is that there’s no way in the world that I will take the Senator’s ugly pecker in my mouth and swallow any of his vile spunk. And I will tell him so to his fat ugly face!”
“I admire that. I wouldn’t want to either, But we are both in a tight spot here. If you go down, Barb, I do too as the one responsible for bringing you here. And remember what happened out there in the water. You and I, Barb. I hope we mean something to one another and can somehow beat this thing together. But openly contesting their sordid little games might not be the best way. Think about it. Now, we’d best get back to the house.”
Barb woke with a start. Reaching for her iPhone, she checked the time ... 7:13 it read on the multicolored screen.
She felt disoriented and it took a few seconds to clear her mind and realize that she was in her ‘Companion’ room. She was lying naked on her bed, and must have fallen asleep from exhaustion there the night before. Her legal pad lay nearby, still open to the notations she had entered. Picking up the pad, and rubbing the sleep from her eyes, she read:
'Sensational scoop - Pulitzer Prize?"
1. Find out the identity of the 'Senator'. Make him pay for this with a forced resignation!
2. Get in-depth interviews with Delia and Tara. Get their 'stories' for depth and color.
3. Avoid any further whippings or worse, if possible (unlikely, but worth a try).
4. Sleuth out whether there is a way to somehow get off this friggin' island, preferably before Robert gets an opportunity to inflict permanent damage.
5. If and when I ever get back to Pitcher, investigate Dean Carter. He's got to be involved in this!
The shame and utter humiliation of the previous evening’s events came rushing back. She recalled with distaste how she had been compelled by Kelly, backed up by Robert, ‘the enforcer’, to give herself up for the ‘very first time’ to the likes of that pig of a Senator. Not the way she had ever imagined it happening!
That coupled with the realization that things would likely get worse for her before they got better if she didn’t come up with a sure-fire way to get off the island soon was more than she was prepared to face that morning. She felt like crying.
But ... on the other hand, the bullet points on the legal pad page also reminded her of the work to be done ... and the glory to be won if she could manage to hold fast to the investigative mission that had brought her to Pirate Cay! She may have been hoodwinked and debased, but she could still turn the tables and win in the end if she played her cards right.
“Yes, I can!” she said to herself out loud.
She had set her legal pad down and was just about to go get a shower when she heard the now familiar metallic clunk made by the externally controlled locking mechanism within the bedroom door. The door swung open and in waltzed Kelly, dressed in tee-shirt, shorts and flip flops, and sporting a big happy smile.
“Morning Barb,” she chirped breezily.
“Don’t you believe in knocking?” sniped Barb irritably.
“Oh, come on. Brighten up. It’s a beautiful morning. We should go for a nice swim together.”
“I’d prefer to be just left alone this morning, if you don’t mind.”
“What’s the matter, Barb. Still sore about having to let the Senator deflower you last night?”
“I was, for all practical purposes, raped.”
“No, you weren’t, Barb. You climbed onto that coffee table and rode him. I saw you do it with my own eyes. A pro couldn’t have done a better job of getting him off.”
“Under coercion, Kelly! You know friggin’ well, it was under coercion ... extreme coercion, I might add. One can get herself whipped around here for not playing along, and I’m not happy about it at all. Now, do me a favor and kindly leave my room.”
“His room, Barb ... not your room ... HIS room. You signed a contract. You’re here to serve him and that means everything, or else.”
Barb snorted derisively and turned her back on Kelly.
“Hey, Barb. What’s this?” said Kelly, frowning and reaching for the legal pad lying at the edge of the bed.
“That’s mine and it’s private,” cried Barb, her face showing alarm as she snatched it away and held it to her chest.
“Okay, sure Barb. I was just curious. Look, we got off on the wrong foot here. Let’s rewind and start over. How about that swim?”
“Okay, why not?” relented Barb as she stooped to slip the legal pad into her bag and zip it shut. “I’ll need to get something to wear.”
“Oh, no need for that. We’ll take a nice little dip in the nude. There’s no one around and even if there were, this is Pirate Cay. Everything here is private and uninhibited. He likes it that way. And the water’s so warm and nice. I do it in the nude all the time.”
“Well, okay.”
“Great, come on then,” chirped Kelly taking Barb by the hand, and leading her out into the corridor. Together they proceeded to the double glass doors at corridor’s end and out onto the dewy grass, the azure waters beckoning but a short distance away.
When they reached the water’s edge, Barb ventured a toe to test the temp while Kelly stripped away her tee and shorts and tossed them aside. She flashed Barb a smile, took her again by the hand and led her into the water.
Wading out until the water was nearly chest high, Barb marveled aloud about how clear it was. “Look, I can see some cute little fishies down there,” she exclaimed with almost child-like glee.
“Yes, the Caribbean is remarkable,” smiled Kelly. “Look over there, Barb, that’s his yacht moored to that buoy. Why don’t we swim over there and sun ourselves on its deck?”
“Is the water deep there? I mean over my head? Because if it is I can’t. I don’t know how to swim.”
“Well, I suspect it is. We can just stay here, if you’d rather, Barb. You’re really lovely, you know?” cooed Kelly, turning to Barb and embracing her in a hug that drew their bodies closer together frontally.
“Well, I do try to stay in shape,” replied Barb, attempting to back away.
“No, you really are quite lovely, Barb,” insisted Kelly brushing her open hands across Barb’s erect nipples and then gently cupping and lifting both breasts.
“Uh, Kelly,” said Barb backing further away. “We’re really not close friends ... I mean, not THAT kind of close friends.”
“Ummmm,” replied Kelly, slipping herself deftly around behind Barb to nibble at one side of her neck.
“Kelly! Stop!”
“Why?”
“Because ... uh ... I’m not into that kinda thing.”
“Really, Barb! What do you do? You were a virgin until last night. You don’t give head. You can’t swim. You obviously aren’t much of a drinker. And now, you’re telling me you’ve never done it with another girl? You did live in a women’s freshman Pitcher College dorm, right? What did you think was going on at night? You’re telling me you never ... “
“Well, I am what I am and what’s it to you anyway? I just ...”
Kelly cut her off by turning her about, bringing them face to face and kissing Barb hard on the mouth. And before Barb could break free, she reached down for her pussy, probing expertly with her fingers.
“Mmphhhhh” uttered Barb, the only sound she could make as she was overcome by the sheer force and passion of Kelly’s full-mouth kiss, and the tingling sensation of Kelly’s finger pressing firmly against and rubbing her clit.
Then she gasped as Kelly’s quick hot butterfly kisses moved inexorably from Barb’s mouth to her neck and shoulders and down to her breasts and nipples. And as Kelly slipped one, then two, then three fingers in, curling them slightly and moving them in and out with rapid strokes, what remained of Barb’s resistance began to evaporate. She began to moan ... a soft guttural moan ... as her body relaxed and began to rock forward and backward in the water in rhythmic response to Kelly’s stroking fingers. Releasing a nipple, Kelly’s mouth retraced it’s meandering path in reverse until she was kissing Barb again on the mouth, receiving this time a far more welcoming, open-mouthed response.
They remained locked together like that for several minutes before Barb’s hand sought out Kelly’s pussy, tentatively at first but then rushing to reciprocate.
*************
High on the balcony that overlooked the shore, the Senator felt a tap on his shoulder.
“Something interesting going on out there, Senator!”
“There sure is,” grinned the Senator, removing the binoculars from his eyes and handing them over to his host.
“Seems your assistant, Kelly, is doing an admirable job of carrying out your orders.”
“Giving our innocent one some pointers, is she?” he laughed as he focused the binoculars on the pair in the water.
“You do remember what you promised me last night, I hope?”
“Of course, I do, Senator. The afternoon’s activities will be most memorable. I guarantee it.
“Hand me those binoculars again.”
“Sure thing, Senator.
**************
Kelly reclined on her side, head cradled on her hand, gently tracing little circles on the pebbled pink aureole surrounding one of Barb nipples.
“You actually enjoyed that, out there in the water, now didn’t you?” she said softly. “Felt good didn’t it.”
Barb stretched lazily on the sand where they lay at the water’s edge and murmured, “I guess I probably did.”
“Probably? Only probably, Barb?”
“Well ... what I mean is ... well, it probably wasn’t right.”
“Oh, of course it was right, Barb. Don’t kid yourself. It was hot, and you loved it!”
“Well, maybe so, but ...”
“No, give it time. You’ll see. This place opens new vistas. That’s what Delia and Tara came to accept. And you will too.”
“I really doubt it.”
“And that, by the way brings up something else that I need to say to you.”
“What’s that, Kelly?”
“Well it’s about the Senator. Do you remember what he wanted you to do for him and you refused?”
“Yes. How could I forget. Disgusting!”
“Well, I’ve been told he wants to give you another chance.”
“Oh no! Never!” exclaimed Barb, sitting up suddenly. “There’s a limit beyond which I refuse to go!”
“Barb! Be reasonable. Refusal can be costly. You’ve learned that already. They’re capable of anything.”
“And you’re one of them. Kelly. You’re an enabler.”
“No Barb, I’m your friend and protector. You need to trust in me. I know it can look bad, but I’m really on your side. Take my advice and you’ll walk out of here one day when you’re contract expires.”
“And you’re advice is to go along with whatever they demand?”
“Essentially, yes, but with my guidance. I can and will protect you from the worst, Barb. I really will.”
“Thanks. I do believe you may be sincere in that, But I’ll make my own judgements. And right now my judgement is that there’s no way in the world that I will take the Senator’s ugly pecker in my mouth and swallow any of his vile spunk. And I will tell him so to his fat ugly face!”
“I admire that. I wouldn’t want to either, But we are both in a tight spot here. If you go down, Barb, I do too as the one responsible for bringing you here. And remember what happened out there in the water. You and I, Barb. I hope we mean something to one another and can somehow beat this thing together. But openly contesting their sordid little games might not be the best way. Think about it. Now, we’d best get back to the house.”
M
montycrusto
Guest
Am I the only one hearing the “Jaws” theme...?
Fossy
SEXPIOGENTUS
“… She may have been hoodwinked and debased, but she could still turn the tables and win in the end if she played her cards right. “Yes, I can!” she said to herself out loud …” - reminding me a little of the redoubtable Amanda in PrPr’s ‘Imprisonment and Execution in Modern Singapore Part III of Barb’s Singapore Saga.
“… Barb’s hand sought out Kelly’s pussy, tentatively at first but then rushing to reciprocate …” - Our girl is very quick learner!
“… the Senator felt a tap on his shoulder …” – Is that like Water On The Knee?
“… If you go down, Barb, I do too …” – Never was a double entendre so apt!
A very arousing chapter indeed! ...
“… Barb’s hand sought out Kelly’s pussy, tentatively at first but then rushing to reciprocate …” - Our girl is very quick learner!
“… the Senator felt a tap on his shoulder …” – Is that like Water On The Knee?
“… If you go down, Barb, I do too …” – Never was a double entendre so apt!
A very arousing chapter indeed! ...
Praefectus Praetorio
R.I.P. Brother of the Quill
That is not just new. In 1964, Bob Dylan wrote (in jest?)
"Now, I'm liberal, but to a degree
I want ev'rybody to be free
But if you think that I'll let Barry Goldwater
Move in next door and marry my daughter
You must think I'm crazy!
I wouldn't let him do it for all the farms in Cuba."
Praefectus Praetorio
R.I.P. Brother of the Quill
Who says Barbara is not a pro? So hot!
And we are all very thankful to you for that!
I find that very hard to believe.
Oh, I'm not sure. That episode relieved some of my tension.
Sorry. TMI?
windar
Teller of Tales
CHAPTER EIGHTEEN
“Do you really think that was Barb’s first time, Dee?” Tara Malone asked her friend and former Pitcher College roommate, Delia Ortiz as they waited inside the exercise room for their daily workout under the strict supervision of their personal trainer, former Providencia Marines Drill Sergeant and Pirate Cay’s resident disciplinarian, Robert. They were clad in string bikini tops, shorts that barely dipped below their lower cheeks and sneakers.
“Well, Big Fred said she was certifiably a virgin.”
“What the fuck does that mean?”
“I assume it means that the doctor examined her the way she did with us when we first arrived. You know, the full pelvic. I guess Barb was intact. I don’t think he’d lie to the Senator.”
“I guess so,” Tara replied. “He never tried to pass us off as virgins.”
Delia laughed. “Good luck with that, girlfriend! In my neighborhood they’re few and far between."
Tara laughed also. “Yeah, most of the girls in the trailer park got started pretty early. Who was your first?”
“Some friend of my older brother’s. Yours?”
“A guy in high school.”
“Anything beats the Senator, I’m sure.”
“You’re not kidding, Dee. That guy is a pig and I bet we haven’t even seen the worst of him yet.”
“Yeah, poor Barb. Though she actually seemed to get into it after a while.”
“She did, didn’t she? That’s Pirate Cay for you. Once you give in and go with the flow, you can actually have an OK time.”
“I wonder if she’s gay?” Delia suggested. “That would explain not having done it with a guy.”
“Well, I’ll bet Kelly is checking that out very carefully.”
Delia laughed. “Count on that, Tara!” she replied. “It’s just another rite of passage down here.”
“Well, Kelly is very…skilled,” Tara said.
“I can’t stand the bitch, but, yeah, she is. So maybe Barb will get into that, too.”
“Maybe,” Tara allowed. “We’ll see if she wants to join us some time. But I’m pretty sure the boss won’t let her get away without giving the Senator that b.j. I don’t get why she makes such a big deal out of it. It’s just one of those things guys want, so you do it.”
Delia shook her head. “Hard to figure, but you know who’s going to win any test of wills. His island, his rules.”
“Yep, she can do it the easy way or the hard way, but do it she will.” Glancing up, Tara saw Robert’s muscular figure entering the gym.
“Alright, you two!” he announced, his voice authoritative despite the soft island lilt. “Your classmate didn’t join you?” he asked.
“I think she’s down at the sea with Kelly,” Tara replied, rolling her eyes.
“I’ll speak to the boss and see if she will be joining you tomorrow. Now drop and give me thirty.”
The two students looked at each other. “Thirty?” Delia asked nervously. “I thought we were supposed to do twenty.”
“You’ve done twenty, now we have to step it up,” he replied. “That’s how a training regimen works. Always more. Now, down we go.”
Reluctantly, Tara and Delia got down on the floor. Robert pulled out his phone and reset the stopwatch. “Ninety seconds, let’s go!” he ordered.
The two women pushed their upper bodies up, straightening their arms, then let gravity lower their torsos back to the prone position. Then up again, and down, each counting in their heads, focusing on breathing as Robert had taught them.
They were on seventeen when Robert called “Sixty seconds!”
‘Shit!’ Delia thought. ‘There’s no way I can do thirteen in the remaining thirty seconds.’ Yet, she knew that failure would almost certainly have a price, so she pushed harder, gasping for breath, her heart pounding, sweat covering her skin.
“Time!” Robert called all too soon. “That’s twenty four for Tara, twenty three for Delia. He will be disappointed.” Tara knew it wasn’t good to disappoint him.
After a brief rest, Robert ran them through their treadmill routine-up and down imaginary hills. Robert’s eyes were glued on Delia’s tits, which were bouncing furiously as her legs worked. Finally he announced “OK! That’s enough. You can go cool off in the ocean. After lunch, you are to report poolside. You got that?”
“Yes, sir,” they both replied.
The beach was deserted when they got there. They quickly took their shoes off and headed into the water, feeling the buoyancy easing their sore muscles. “What do you think this poolside after lunch is all about?” Tara asked.
“I don’t know, “Delia replied, “But this is Pirate Cay, so you can bet that Barb will find herself faced with a tough decision.”
“Better her than us,” Tara said.
***
Tara gasped as she and Delia entered the pool enclosure after lunch. She had never seen anything quite like the heavy wooden structure that stood on the concrete deck near the deep end of the pool.
“What the fuck is that?” Delia muttered.
As they approached, Tara could see that there were thick leather straps attached to the base of two of the upright pieces and to one of the crossbars. She reached out a hand to push against one of the uprights. It didn’t budge. This wasn’t surprising, since the bottom of each of the wooden uprights ended in a bracket that was screwed onto a bracket that was firmly set into the concrete.
Tara shook her head. “Whatever they plan to do with this is not going to be good.”
“I hear that, girlfriend,” Delia added. And, hearing the voices of their employer and the Senator approaching, she added, “I don’t think we’re going to have to wait too long to find out either.”
The two men entered the pool enclosure, trailed by Kelly and, behind her, by Robert, who was carrying a duffle bag, which he set down next to the wooden frame. They sat on deck chairs under a large canopy that shaded them from the harsh tropical sun, facing the apparatus, which was in full sun.
“Don’t be shy, you two, come and join us” he said, beckoning Tara and Delia over. He took hold of Tara’s arm, pulling her onto his lap. The Senator did the same with Delia, untying and removing her top as soon as she sat, and pawing her large breasts.
“Where is little Miss Too Good to Give Blow Jobs?” the Senator asked.
“Would you please go get Barb?” the billionaire asked.
Robert and Kelly left, returning in a few minutes with a completely naked Barb between them, each of them holding firmly on to one of her arms. She was biting her lip trying hard to look brave and determined, but Tara could tell she was scared shitless. Her eyes darted back and forth between the two men and the intimidating wooden frame.
“Barbara,” he began. “You came down here to Pirate Cay of your own free will, did you not?”
She looked down at her feet, then up at him. “Yes, sir, but…”
He shook his head. “I flew you down here, provided you with a nice room, did I not? You have shared my food at my table.”
“Yes, sir, that’s true.”
“You just had a most enjoyable swim with Kelly, I am told.”
Tara could see that Barb looked very uncomfortable at the mention of that. She didn’t know exactly what had happened between Kelly and Barb, though she had a pretty good idea.
“Yes, sir,” Barb replied shifting her weight from foot to foot.
“You have been promised a large sum of money with the possibility of bonuses for good performance, haven’t you?”
Barb nodded.
“And what is asked of you? That you provide companionship for me and my guests. That is how business works, by a mutual exchange of things of value.”
“The Senator is my guest. He requested a favor from you, something that women do for men every day all over the world. And you refused.”
Barb looked like she was about to speak, but he glared at her and she held her tongue. “The Senator was, to be very frank, displeased by your refusal. I don’t like my guests to be unhappy. Nevertheless, we realize that you are innocent and all this is new to you. You were whipped for the first time and lost your virginity yesterday. The Senator understands this. And he is willing to give you a second chance, Barbara, in the spirit of generosity that guides us at Pirate Cay.”
“I’m sorry,” Barb replied. And Tara had to admit that she did look sorry.
“That’s good Barb. Sorry is a start. Now I want you to get down on your knees and crawl over to the Senator and provide him the pleasure he deserves.” Delia started to get up so that the Senator could receive his tribute from Barb.
“I’m sorry, but I can’t,” Barb said.
“What the fuck did you say?” the Senator demanded. “What do you mean can’t you little bitch?”
“I don’t mean any disrespect, but it’s gross and I can’t do it.”
“Barb, what did we talk about just a little while ago?” Kelly asked her. “You have to.”
Barb shook her head.
“Well, now I’m sorry,” he said. “In business and in life one doesn’t get an infinite number of chances. Put her on the frame.”
“No!” Barb protested. “You can’t!” This is outrageous!” She tried to break free, but Robert had an unshakable grip on her left arm and Kelly, despite being slim, was stronger than she looked and had Barb’s right arm immobilized.
Barb tried kicking out at Kelly who dodged the attempt with practiced skill. They dragged the protesting, wriggling student over to the frame. Robert used his considerable bulk to pin the squirming naked Barb against the crossbar on the far side, while Kelly knelt and fed the straps attached to the uprights around each of Barb’s ankles and pulled them tight.
Then Kelly went around to the other side. Robert pressed down on the small of Barb’s back, bending her waist at a ninety degree angle. Kelly strapped her wrists to the cross bar on the far end. Barb was now more or less immobilized.
Barb’s struggles and the way she had been forced to submit to the superior force had made the boss quite aroused. Tara could feel his erection pressing into her ass.
Tara watched Robert open his duffle bag and remove a fearsome looking cane, as thick as his smallest finger, though small was a relative term in his case, and a bit longer than his arm. He swished it around. The sound sent a chill down her spine. She could only imagine how it must sound to Barb, who was completely vulnerable to its bite.
Robert brought the cane close to Barb’s face. Her eyes were fixed on the concrete, trying hard not to look at the instrument that would soon be used to break her will, but she couldn’t resist giving it a quick glance.
“Look at this cane, girlie,” Robert ordered. “When I was in the Providencia Marines, we used to use this now and then on misbehaving recruits. Grown men, and they would howl and cry. After that, no more trouble from them. Now imagine how this will feel when it bites into that tight little ass of yours.”
Barb looked up at the cane for a moment, her eyes wild with fear. She stared at Tara and Delia, hoping, perhaps for their help, but what could they do? Tara was just glad not to be facing that awful cane herself.
“Let me up Delia,” the Senator said. He lowered his shorts and underpants and stepped out of them. He was semi-erect. He walked over to stand in front of Barb. His crotch was at the level of her face. “Last chance, cunt,” he said.
Barb shook her head.
“Don’t be a fool, Barb,” Kelly advised, but it was too late.
“Give her a taste, Robert,” their employer ordered.
“It will be my pleasure, boss,” Robert replied, striding purposefully behind Barb. He tapped the cane a few times against her buttock cheeks to find his range. Then, he took a step back, drew the cane behind him and lunged forward, his arm driving the implement of punishment in a vicious arc towards the target.
Tara heard the “Whoosh” as the rattan sliced through the air and the crack, like a pistol shot as it struck the soft flesh. Barb’s head shot up. Her eyes were wild with pain and fear.
Tara could hear Barb’s sharp intake of breath and then the deep throated cry of shock and protest. “Owwww! Fuck!” Barb yelled.
“Give her another one,” he ordered.
“Yeah, make the bitch pay for her insolence,” the Senator seconded the motion.
Robert struck again. “Oh, god! Ohhhh!” Barb cried.
The Senator moved in, his penis now fully erect, the tip just an inch or two from Barb’s face. He reached down and grasped her hair, pulling her face up. Tara could see tears rolling down Barb’s cheeks.
“Come on, girl, do your job,” the Senator ordered.
“Barb, just do it,” Kelly urged. “They won’t stop until you do. Why prolong your suffering?”
Barb shook her head.
The Senator nodded at Robert, who wound up and struck again, provoking a spate of wordless howls from poor Barb.
Tara could feel her employer’s cock pressing into her ass even more insistently. “I want you, Tara,” he said. She stood and stepped out of her shorts as he did the same, then sat back down in the chair. Tara got back on his lap and slipped his penis inside of her. She was very wet and it slid in quite easily.
He beckoned Delia over. She stood next to them. He nuzzled her breasts as Tara rode him up and down.
Robert struck again, three more times without a pause, each one eliciting a shriek of pain that finally fell to a soft moan. “Please stop, please,” Barb begged, her voice hoarse from screaming.
“Oh, you want him to stop, cunt, do you?” the Senator said, yanking hard on Barb’s hair to raise her head. He thrust his pelvis forward so that the tip of his rock hard penis was against her lips. “All you have to do is take it in. Otherwise, he’ll keep going.”
“Barb, the decision is yours,” their employer added, his voice strained with trying to hold back his pleasure as Tara rose and fell on his lap. “In business, sometimes you have to cut your losses.”
Barb kept her lips closed. Robert struck again, then once more. Tara was feeling very good riding the hard cock that pressed against her cervix each time she slid down onto his lap, before rising again.
With the next lash, the dam broke. “Oh, God, it’s too much! I can’t take any more!” Barb cried. The Senator slid his erection into her open mouth. She didn’t resist.
“Now you’re finally getting smart, you little slut,” the Senator cried. “Take that all the way in!”
Tara felt her employer thrusting his hips against her ass, and, then, as he moaned her name, she felt the wetness inside of her. She went over the edge, too, shivering with pleasure. She idly wondered if this would be the moment when his heir was being conceived.
As Tara came down from her orgasm, she watched the Senator slowly fuck Barb’s mouth. “Swirl that tongue around the head,” he panted. “That’s a good little whore.”
Soon, the Senator announced, “Get ready. I’m going to cum. And you better swallow every goddamn drop if you know what’s good for you.” His body went rigid and he shouted. “Fuck!” and pulled Barb’s head tightly against his crotch, holding it there for several seconds before he finally relaxed.
Tara couldn’t tell whether Barb really did swallow every drop. It seemed to her that quite a bit dripped down her chin onto the concrete below.
But the Senator didn’t seem to notice. He seemed happy, at least for the moment, that he had forced her submission. He came over to his host and high fived him in triumph. “Goddamn, that little slut has a nice mouth! Now that she knows what it’s good for, she’ll make some man very happy!” he crowed.
Meanwhile, Robert glanced over at the boss, who nodded wordlessly. Tara watched him strip off, his body gleaming with sweat from his exertions in the sun. His cock was pointing up, large and hard.
Robert moved in front of Barb to the spot where the Senator had stood moments before. Wordlessly, he slipped his erection into Barb’s mouth and began thrusting. “That’s it, Barb, thank Robert for teaching you the error of your ways,” Kelly said.
Tara watched as Robert used Barb’s mouth like one of those sex dolls, caring only for his own rising pleasure. Soon he groaned loudly, pulled out and emptied his balls all over the poor student’s face, before collapsing into one of the pool chairs for a well-deserved rest.
“Wow! That was hot!” Kelly exclaimed.
“Feel free to take advantage, Kelly,” their host exclaimed. “Barb’s job is to satisfy. Man or woman, we’re all friends here.”
Kelly quickly stripped off. Naked, she placed herself in front of Barb where the two men had stood. Being shorter than them, she had to stand on tiptoes to have her crotch at the level of Barb’s face. “Go on,” she urged. “You know what to do.”
And it appeared Barb did, as she let her tongue out of her mouth to lap at Kelly’s slit. Soon, Kelly was bouncing up and down on her toes, rhythmically, chanting, “That’s it, Barb, that’s a good little slut.”
The rampant nature of Kelly’s pleasure had made the billionaire and the Senator hard again-a tribute to the doctor and the wonders of modern pharmaceuticals. “Get down on all fours, Tara,” he ordered. “You, too, Delia.”
Quickly he slid into Tara, while the Senator entered Delia. The sounds of their pleasure mingled with Kelly’s as she pressed her crotch hard against Barb’s face.
Later, after pitchers of iced tea and margaritas were brought out for the thirsty participants-all except Barb, that is-their host asked Robert, “How are these two doing by the way?” indicating Tara and Delia.
“Some progress, boss, but they came up short of thirty push-ups today.”
“Well, let’s see how they do tomorrow, Robert. But leave the caning frame there as an inducement to try harder.”
M
