Jamaican Vacation Day 2 Pt 01

The alarm woke Hannah from the nightmare she was having, though it was more memory than a dream; her mind hardly needed to invent anything outlandish or extreme for her to suffer through. She lay looking at the ceiling, not wanting to wake but unwilling to be haunted yet again by the evening she'd spent in Harold's suite as a prostitute.

Sid turned the alarm off before rolling over to look at his wife. "You have to get up, baby. Breakfast is in half an hour, and then you must choose how you spend the day."

Hannah pulled the covers back over her head; she didn't need the reminder. She wasn't ready for another day with Sid calling the shots; she was legitimately afraid he might sell her back to Harold again. Just thinking about the previous night sent a shiver through her. That left one of the free use days- everyone or just the staff being allowed to have their way with her- or a day of being some stranger's submissive.

The covers flew off. "Come on, honey. If you don't get moving, you will run out of time and start your day without anything to eat."

"Fine," she snapped, swinging her legs over the side of the bed and standing. Even on her way to the bathroom, she still couldn't let it go. "You could have let me sleep a little more." Sid watched her naked ass as she left the bedroom, getting hard just thinking about what might happen that day.

As they made to leave the room, Sid stopped Hannah and forced her to face him. "Do you want to talk about things?"

She bit her lip and thought for a moment. "Not right now."

He smiled and kissed her, holding her briefly before she pulled away. "We have breakfast to get to before my day starts," she said with a sad smile.

Sid let it go, knowing she was right about how short time was.

They were still sitting at breakfast when the tablet the resort had given them dinged. Sid unlocked it and saw a new message, reminding Hannah that only thirty minutes left to decide on the day's task.

Sid passed the tablet to his wife. "Hey, no pressure, but you have thirty minutes to pick, or the resort will choose for you." Sid saw that she was indecisive. "Babe, you will be doing all of them. Let the resort do it for you if you can't pick one. Maybe that will make it easier."

Closing her eyes, Hannah randomly tapped one of the buttons, locking in her choice: Staff Free Use. Sid chuckled as he accepted the tablet back from his wife.

"What?" she asked, flushing slightly.

He pointed to her wristband, which had gone from neutral to white, and said, "Nothing. I think Amani and Sabryna will have a fun day."

"I didn't choose it for..." Hannah started to protest but stopped when Sid held up his hands.

"It doesn't matter to me why you chose it, honey. I'm glad you decided before the resort decided for you." Sid was going to say more, but Amani walked up.

"Sir, I hope you had a pleasant evening and are well rested."

Sid happily shook his hand. "The room was superb, and breakfast was fantastic."

Amani shifted his gaze towards Hannah. "How was your evening, Madam? Did you enjoy your festivities?"

Hannah blushed and looked down. "It was great," she said unenthusiastically.

Amani chuckled, placing his large hand on her naked shoulder and gently squeezing it. "Many of our guests are overwhelmed the first few days after they arrive." He leaned closer, whispering into her ear, his hot breath sending shivers down her spine. "Truth be told, some don't appreciate the experience until several months after they return home. I have heard they try to find similar experiences closer to where they live, but it isn't the same. That's why over ninety percent of our first-time guests return at least once."

Leaving his hand possessively on her shoulder, he turned to Sid. "Congratulations, Sir. After escorting Madam to her duty station today, the business office instructed me to bring you to the membership office."

Sid was relieved that Harold had kept his side of the bargain. He had been worried when his band had remained blue, and the tablet had still displayed associate status in his profile. "Thanks, Amani. I was getting a little worried since the status hadn't changed."

"I understand, Sir. The membership office opened half an hour ago and started processing the changes." He turned to Hannah. "It's time to go, Madam. You don't want to be late."

Hannah stood, feeling very nervous. She bent over, kissing Sid. "I don't know if I can do this," she said.

Sid took her face in his hands, feeling her trembling as he kissed her back. "This is one of your favorite fantasies, babe. You are perfectly safe here, so embrace the role and enjoy yourself."

Giving Sid a nod and a half-smile, she turned to Amani. "I'm ready."

"Excellent, Madam," Amani said. He turned to Sid. "I will return shortly." He put his arm around Hannah's waist and guided her toward the exit. They hadn't moved two feet before his hand dropped and cupped her ass. After another few steps, he had a finger in her asshole and pussy. Despite her shuddering, she continued walking, doing her best to pretend that nothing was happening.

Sid watched them until they turned the corner, then sat and drank coffee, watching the parade of men and women walk through the breakfast area. Sid glanced at his watch at one point and was surprised to find that his butler had been gone for almost forty-five minutes. His first instinct was to feel annoyed, but then a thought occurred to him.

I wonder if he fucked Hannah before coming back?

He smiled as he took the last sip of his second cup of coffee.

Almost like magic, Amani appeared next to the table. "Sorry for the delay, sir. It took a little longer than expected to get Madam situated."

"No worries. I'd been watching the scenery myself and had lost track of time until I saw you walking back. Was everything okay?"

"Oh, yes, Sir. Madam is amongst the others awaiting a day of serving the staff. Would you follow me?" Amani turned and walked a few steps away, then waited - clearly, for Sid to stand and follow, which he eagerly did. A short walk later, they came to an unassuming door they had passed the day before when they'd left the reception area.

Amani turned the knob and pushed it open for Sid. "If you need me, Sir, just page me, and I will find you."

"Thanks," Sid said as he walked into the room. He was startled when the door shut behind him, assuming Amani had closed it before walking away.

Likely to fuck Hannah again

, he thought. The images of Amani's cock in Hannah's small hands were interrupted by a young woman walking into the room.

"Hello, Mr. Davis. My name is Jada, and I will be assisting you today. If you will follow me?" The young Jamaican woman then turned and walked through a doorway.

The whole "asking" thing is a formality, huh?

Sid couldn't get too upset about that, however. He felt his dick rise in response to the sight of her fit yet curvaceous body moving inside the tight-fitting dress. He followed her down the hallway to an office, which, besides the large desk and leather-backed office chair, offered a white chaise lounge, plus a few other chairs on the desk's opposite side. Jada moved around the desk and took her seat. The slit in her dress ran almost to her waist, exposing most of her thighs as she turned and began typing.

After a few moments, she looked away from her monitor and towards Sid, who'd taken one of the chairs in the meantime. "Okay," she said, "first, let me congratulate you on attaining gold status; it's rare for anyone to receive it on the first visit. Here is the paperwork to sign before I review your benefits." She handed Sid a clipboard with a multi-page contract attached.

Sid skimmed the contract; most were standard boilerplate, but one section gave him pause. Sid looked up. "It says I must make yearly payments of eight thousand dollars, USD., for the next twenty years. I thought gold status included everything."

"The eight thousand is a maintenance fee all gold members make to help sustain the resort," Jada replied smoothly. "That fee also covers a stay of up to two weeks per year. Of course, you can divide that into multiple weekends if you like; several of our members do that."

Sid did a quick calculation. "That is over four times the cost of a blue-level membership for the same timeframe."

Jada nodded. "Yes, Sir. Gold membership comes with many more benefits than blue-level."

"Do I have to sign this? My deal with Harold was this level of membership." Sid didn't say for using his wife like a whore, but the smirk Jada gave him said she knew.

"No, Sir. You will remain a gold-level member for the remainder of your stay, but you cannot access any other benefits after leaving the resort like a standard member unless you sign the contract."

He turned to the last page, listing all those extra benefits. The first item was the two weeks of resort usage that Jada had already mentioned. The second benefit was access to the resort's archives of his visits. The archive allegedly included videos captured while fulfilling contracts at the Terrace or during private parties. He would also gain access to an extensive network of swinging and BDSM clubs located around the world, as well as the opportunity to bid on auctions at the Terrace. He also would gain full access to live feeds from the resort's public areas. The last item on the list was special access to private events.

"What are private events?" he asked.

"They are varied. The last one was an orgy with a professional sports club's cheerleader squad. As you can imagine, it was trendy, and spots went quickly."

"It seems like a lot of money..."

"The agreement you made last night paid half of the first year's dues. I am happy to give you credit for that and your current stay. That drops your first-year cost down to two thousand."

Wow,

Sid thought,

Harold paid four thousand for Hannah being a whore at his party last night.

Seeing that Sid was still unsure, Jada's smile thinned. "We may have another way to resolve the cost issue," she said, taking the clipboard back from Sid. "As you know, you require a sponsor to become a member at any level. Since you were not referred to us by an existing member, the committee vetted your application. It turns out that one of the committee members knows you and your wife."

Sid was shocked that anyone he knew would be involved with the resort and began wracking his brain to see if he could figure out who it was.

Jada kept talking, not caring that Sid was distracted by his thoughts. "They were intrigued and decided to sponsor you. Before you ask, they want to remain anonymous since they don't know how you would react."

He gave up trying to guess who it might be; he was too shocked by the revelation even to begin sorting through years of possible missed hints. "You said there might be a way to offset the cost?"

Jada smiled. "Yes. If you agree, when your wife goes for her Submissive day, the party that sponsored you will take ownership of her. Typically, that is randomly assigned, and there is a safe word. I will warn you that their tastes can be abusive, and no safe word will be honored. They will cover this year's fees in exchange for your wife's use. In addition, if you agree to allow them one weekend every other month of complete control, they will cover the membership fee for that year."

Sid thought about it for a few minutes. "What happens if I agree but change my mind later?"

"You can break the contract without penalty, but you must begin paying the maintenance fees from that point forward."

"Can I think about it? The thought of pimping my wife out for an upgraded membership is kind of..." He struggled with the word he wanted to use.

Jada smiled, giving him a conspiratorial wink. "Yes, Mr. Davis. Take until the end of business today and think about it." She typed on her keyboard, and Sid's band turned gold when she hit enter. "You have full gold member status for the remainder of your stay." She stood, extending her hand. "Please remember, the offer we discussed expires when this office closes today. It was very nice meeting you, Sir."

Sid took the hint and stood, shaking her hand. "It was nice meeting you too, Jada." She escorted him to the outer door and left him in the hall. Retracing his path, he was soon back on the beach, listening to the sounds of the waves and the moans of the other guests. He grabbed a drink from the bar, found a lounge chair, and settled in to watch the water - or, more precisely, to gaze in its general direction whilst thinking about the offer and wondering what Hannah was doing.

***

Hannah was terrified as Amani escorted her away from Sid; it was made worse by the way he palmed her ass and forced his fingers inside her asshole and pussy.

Once outside, she felt the heat of the Caribbean sun on her skin. Amani looked over at her as they walked down the path. "How are you enjoying your stay, Madam?"

Hannah cast a nervous glance at him, blushing at the casual way he spoke while taking liberties with her body. "It's very pretty here," she said wistfully. "I wish there were some time to enjoy it."

"You have only just arrived, Madam. I am positive that you will find time to enjoy the beaches and swim in the ocean before you leave us." They turned off the path and walked past the sign that had had her so nervous during the initial tour:

Staff and Service Personnel Only Beyond This Point

.

As they reached the back, Hannah nervously stepped away from Amani and positioned herself exactly where he had instructed her to wait. He approached Tarone, the activity supervisor, leaving her alone with the others.

Amani clasped Tarone's forearm before pulling him in for a brief hug. "Hey man, I'd heard you pulled activity supervisor today." He glanced around at the other staff members on break.

Tarone offered up a heavy laugh. "Yeah, it's a tough job, but someone has to do it." He looked at Hannah, who was standing across the room. She had moved to the wall and crossed her arms over her chest. "She is a very fine-looking woman."

"She is at that, my friend," Amani replied. "Did you notice the special instructions for her?" He pointed to her name on the activities tablet and the special instructions:

Fuck any hole you want, but only cum in her cunt. Degrade her as you use her. Make sure to tell her you are fucking a baby in her. She is to return to her husband full of cum.

Tarone chuckled. "Does her husband know?"

"Yeah," Amani said. "It's one of her darker fantasies." He walked back to where Hannah was trying, unsuccessfully, to blend into the wall. "You are all checked in, Madam."

"Ahh, thanks, Amani," Hannah said, nervous and unsure why she'd thanked him.

"It was my pleasure, Madam. Now that you have officially checked in, you understand our relationship has changed. I'm no longer your butler, nor will you be addressed as 'Madam' until your wristband reverts to its natural state."

Hannah swallowed as she nodded. A shiver ran down her spine as Amani's expression changed from helpful and smiling to something much harder.

"Good, bitch. That will keep things from getting awkward. Now, get on your knees and pull my cock out." Trembling, she slowly dropped to her knees before unzipping his loose pants and fishing his semi-hard cock out. "That's a good cunt. Now put my cock in your mouth and get it good and wet."

Hannah had been mesmerized by the sight of Amani's dick as it had quickly hardened in her hands, but his command snapped her out of it. Putting the large, black member into her mouth, she played with the shaft and gently squeezed the balls below it.

Amani began to move his cock slowly back until just the head was inside her lips. Then he took Hannah's entire skull in his two large, strong hands, holding it in place. He felt Hannah tense, and it made him smile.

The first instroke was slow and steady, but then he got more aggressive. After withdrawing again, he thrust forward and buried about a third of his meaty shaft in Hannah's mouth before hitting the back of her throat. She choked despite everything that had happened the night before.

Amani pulled back a bit. "You need to work on swallowing a real cock, cunt." He pulled out almost all the way and then pushed back in hard, striking the back of her throat again and again. After a few minutes of her choking, Amani relented and pushed her backward off his dick.

He let her lay on the floor for a few minutes, gasping, before he grabbed her arm and pulled her to her feet. "I ain't got all day, whore. Turn around and bend that ass over. Spread your legs a little wider. Perfect. Pull your ass open. Now, don't you fucking move."

Amani placed his cock against the soaked lips of her pussy and pushed. Her vagina opened and stretched to accommodate his massive member.

"Oh, fuck. It hurts. Please, it's too big."

Amani laughed at her as he kept pulling her hips backward. Once about half of his cock was inside, he pushed her away. Pulling back, he went a little deeper. Hannah was grunting as tears streamed down her face, blurring out the crowd of black men who had come over to watch her getting fucked. Pushing forward hard while he jerked her hips back, he managed to get about two-thirds of his cock buried inside the pretty blonde.

"Oh, God," she said. "Please, stop." She felt like a baseball bat was inside of her. After a couple more small in-and-outs, he slammed into her hard, burying his cock fully inside of her. She opened her mouth in a silent scream; the pain was so intense that she couldn't push out any noise at all, never mind words.

He let her adjust to the invader for a minute before slowly pulling back out. With slow and steady motions, Amani began to fuck Hannah's tight pussy. At first, the pain reminded the petite woman of nothing so much as giving birth to her daughter, but slowly, it turned from pain to discomfort. Then, inevitably, she heard herself moaning.

"That's it, whore. Let everyone know how much you are enjoying getting fucked by a real cock." His comment reminded her that they had an audience. Shame and embarrassment coursed through her, yet they were also woven in with arousal.

Amani pulled her upright by her hair, his cock fully impaling her body. He held her throat, licked her earlobe, and brought his voice down to a whisper despite the eager voyeurs all around him. "I'm going to fuck you until I cum and fill your fertile womb. Then, every one of my associates will do the same thing, fucking you all day long. Who knows? One of us might be the father to your next child."

Those violent, taboo words were enough to trigger Hannah's first orgasm. For a few seconds, as her body shook, the only thing holding her upright was Amani's cock embedded in her pussy and his hand around her neck. People around the circle laughed at her as she shuddered again.

"That's it, slut," he said, playing to the audience once more, "every time you cum, it's that much more likely that you will conceive." Shifting his hands down to her breasts, he lifted her limp body upward before slamming back down, burying his cock inside of her. It hit her cervix on every new stroke, and she orgasmed again, wondering if what he had said was true.

Amani became rougher and fucked her faster as he approached his orgasm. Hannah felt his cock swell, stretching her already distended vagina as he began to pump shot after shot of cum deep inside her, coating her womb. His orgasm triggered a massive one in her, and she passed out from the strength of it. The large black man leaned Hannah forward and pulled his spent cock out of her tight pussy, enjoying the gaping hole full of cum he saw when it popped out.

As another woman on her Staff Use day helped Hannah reach a chair, Tarone laughed and smacked Amani on the back. "That's the way to break in a woman."