Jamaican Vacation Day 2 Pt 02

Author's Note:

If you haven't read the first part, I recommend stopping here and reading that first. Here is a quick recap of day two, part one. Hannah chose Staff Free Use and entertained various staff members on their breaks. The resort upgraded Sid's membership to gold, but if he wanted to keep it, he had to either pay $8,000 or loan his wife to his unknown sponsor for six weekends a year. While thinking over his options, another gold member, Cindy, arrived and gave him some advice. Meanwhile, Hannah was being used and taunted by the service staff of the resort a few hundred yards away.

***

The seabirds were calling to one another, and the waves crashed against the beach twenty yards away, yet Sid was oblivious to the beauty of nature. He groaned while looking at the naked woman splayed on the chair across from him as she tapped her shaven pussy.

"Like what you see?" Cindy slipped a finger inside her wet pussy before bringing it to her lips and licking the juices from it. Sid licked his lips and nodded. "Well, come over here and get some of it."

Sid almost dived off his lounger, landing in the sand, and knelt between Cindy's legs. For a few seconds, he just admired her pussy before sinking his tongue deep inside her.

"Oh, fuck. Yeah, right there." Cindy put her hands on the back of Sid's head, holding him against herself. He pushed two fingers inside her and curved them, starting a gentle rhythm that quickly became a blur as he sucked on her clit.

"Shit!" Cindy exclaimed as her body became ridged and jerked. Sid continued at a slow pace, gently nuzzling her clit. When he felt her body relax, he sucked hard on her clit again. His fingers moved in and out of her at the same pace as before, triggering another powerful orgasm.

He repeated that several times. He was still in the process of doing so when Cindy spoke up.

"Please, stop," she said. "I can't take this anymore."

Sid looked up from between her legs, an evil grin on his face. "What's in it for me?"

An exhausted Cindy brushed her hair away from her face as she opened her eyes and gazed at him. "Whatever you want."

"I want to fuck that ass of yours," he said. His cock was wagging in front of him as he reached over Cindy and picked up a small bottle of lube. The smile never left her face as she turned over and presented her apple-shaped rear.

Sid poured lube over her ass, rubbing it into her winking star before pushing a lubed finger slowly inside her tight asshole. A groan escaped her mouth as he quickly slid his finger in and out. Adding another finger earned him another groan.

By the third finger, Cindy was panting and had begun to lightly rub her clit. "I'm loose enough. Put that big cock of yours inside me before I go crazy."

After lubing his cock, he placed the head against her nether hole and watched as it slowly expanded to accept the tip. Looking down at Cindy, he saw one hand clutching a towel tightly while the other kept working her button. After her ass swallowed the head, he paused a few seconds to let her adjust before pushing forward. Slowly, he worked his cock deeper into her until his pelvis touched her buttocks. In and out, he fucked Cindy while she groaned. After a couple of minutes, he was fucking her at full speed, listening to her moans and grunts as he built toward his orgasm.

"Fuck me. Fuck me! Oh. Oh. Shit!" Cindy began to shake, her pussy contracting on an imaginary cock, spraying cum below her as she orgasmed hard. Sid's orgasm was right behind hers. The tightening of her ass pushed him over the top.

As Sid's cock began pulsing, he grunted, "Take my cum, bitch." He shuddered as his cock sent spray after spray of cum deep into Cindy's ass. When he finished, he pulled out of her, falling back onto the lounger next to hers. They both lay there breathing heavily for several minutes.

Cindy looked over at Sid. "God, I needed that."

"Me too."

After they recovered, they swam in the ocean for a while before departing.

***

Jaden walked through the doorway, taking a seat next to Tarone. "Hey, brother." Jaden clasped Tarone's hand while pulling him close for a hug.

Tarone glanced at his watch. "You done for the day already?" Usually, Jaden didn't show up until late evening.

"Naah. Just bring in a lively family and need to unwind a little bit before I drive them to Old Town. The mother and daughter want to soak up some real native culture while the husband relaxes by the pool, yuh know?" They both grinned, knowing Jaden would return a very used mother and daughter later that night.

Jaden quickly surveyed the Free Use candidates around the room before Hannah caught his eye. "I'm glad I stopped by; I've wanted to bang that ass since I picked her up at the airport. Any restrictions on her?" He watched her getting fucked by one of the waitstaff doggy style, right there on the floor.

"No permanent marks, and you have to cum in her pussy." In response to Jaden's raised eyebrow, Tarone continued, "I guess it started as her husband's idea to push her boundaries, but I heard the sponsor is considering making it happen. Either way, it's part of her restrictions."

"How long is the list to fuck her?"

Tarone showed Jaden the tablet. "There are six ahead of you, brother, but you have more seniority. I can put you at the front of the line if you want the next fuck." Jaden chuckled as the waiter buried himself deep inside Hannah.

"Yeah, I'll take the next fuck," Jaden said, walking toward the couple.

"All my boys are strong and swim fast," the eighteen-year-old said as he pulled his limp cock out of her body. "I'm sure I just fucked a baby into you, bitch." The young man saw Jaden standing behind him. "Hey, Jaden. Going to fuck the cunt?"

Jaden pulled his pants and underwear off, folded them, and sat them on the chair. "I've waited for her to show up since I brought her here." Hannah looked back at Jaden, frowning at the driver's comment; her eyes widened slightly when she saw his cock; he was larger than any she had taken that day.

"It's a good thing you have been so popular today, bitch," Jaden said with a chuckle. "I just hope the thirty boys who fucked you before I got here loosened you up enough for me."

Hannah groaned as he pushed his cock slowly inside her, stretching her sore pussy as it went deeper. "It's too big. Oh God, please stop." Some of the teenage buck's cum was forced out by the massive invader, but the majority went deeper inside, causing the pressure to keep building. By the time his cock was fully seated, Hannah was in tears from the pain.

Slowly, Jaden pulled his cock back out, triggering another whimper from Hannah as her pussy stretched outward. With just the head inside her vagina, he pushed back in. As Jaden increased the speed of his thrusts, Hannah could feel the ejected cum leaking down her legs. He fucked her slowly for several minutes before deciding she was ready.

"You've had enough time to get used to my cock, bitch," he said. He pulled backward, stopping just inside, then slammed forward hard, quickly building a rhythm. Hannah sobbed and grunted as the cock rearranged her insides.

Jaden laughed at her, enjoying her tight pussy, and knowing it was only a matter of time before the first orgasm hit her. From his experience, once the first one happened, she would be nothing but a fuck hole, begging him for more.

"Please, stop," Hannah sobbed. "You're hurting me." Hannah sobbed, and Jaden ignored her. If anything, he fucked her harder. "Hun. Hun. Hun. Please. Oh. Hun. Oh. No. God. Oh. Hun. Fuck!" Hannah shuddered as a massive orgasm ripped through her body.

Jaden stopped fucking her until most of the shudders had stopped going through her body. That, however, was her only respite. A few quick motions and she started shuddering.

"Oh. Shit!" Hannah orgasmed again. Jaden picked up the pace again, the sound of his pelvis slapping against her ass practically echoing in the open space. "Fuck me," she began to chant as orgasm after orgasm washed over her.

He kept fucking until he felt his orgasm approach. "I'm going to cum, bitch. Do you want me to cum in your pussy? Maybe knock you up?"

The pain and the constant orgasms overloaded Hannah's mind; at least, that's what she told herself when she answered. "Please, cum inside me."

Jaden buried his cock inside the white woman and held her hips tight as he shot rope after rope of cum deep inside her. Each shot of hot cum triggered another orgasm in Hannah; by the end, she was only semi-aware of the cock sliding out, leaving a leaking, gaping hole behind.

"Damn it, Jaden," the next guy whined as he pushed his cock into the loose pussy. "You wore the bitch's cunt out!"

Jaden just waved over his shoulder, laughing. "You need to grow a more manly cock, my friend." Several others joined in. After a few seconds, even the man fucking Hannah did. They weren't really laughing at him anymore.

***

Sid had returned to his room and finished changing for dinner when a knock on the door pulled him from his thoughts about what his wife was doing. Opening the door, he found his butler, Amani, standing there.

"Hello, Sir. I hope I haven't interrupted anything."

"Not really; I was just getting ready for dinner."

"Ahh, good then. Before you head to dinner, I must remind you that the business office will close in half an hour, and they need your response before then."

Crap, I completely forgot about that,

Sid thought, walking over to the paperwork sitting on the table. "Hey! Sorry, I lost track of time. No worries, though--I've already filled it out! We can drop it off on our way to dinner."

"Excellent, Sir."

The two men walked through the resort until they reached the business office. As before, Amani waited outside while Sid entered.

Jada was closing one of the other office doors when Sid walked in. "I was almost afraid you would not return before the deadline." She took the papers from him and motioned him to follow her. "Please have a seat." She went through the documents and signed them in several places. "Everything looks to be in order. Getting them into the system will only take a few minutes." Sid impatiently waited as she scanned the documents. A minute or two later, she handed him a binder with his copies inside.

"Is there anything else I need to do?" he asked. Sid was still unsure about signing his wife up without talking to her beforehand and was worried about her reaction.

"No, Sir. The board has already accepted your contract, and I have upgraded your membership to a yearly one. Congratulations on joining. I will send you a welcome gift in your room later tonight." Jada shook his hand and guided him out of the office to where Amani stood. "Amani, Mr. Davis is a full gold member. Please make sure he has access to everything he is entitled to."

"I will indeed." He turned to Sid. "Welcome aboard, Sir." Amani pulled Sid in for a warm embrace. Sid awkwardly patted the larger man on the back, stepping away when he was released. "If you follow me, I will take you to the gold member dining room." With Sid behind him, Amani took a different route to another dining room.

"This way, Sir," Amani prompted when Sid paused to admire the room's elegance. Their path led them across several bridges that spanned a series of water channels within the ample space. Finally, they arrived at a table near the glass half-wall, which offered a breathtaking view of the sun setting over the ocean. "I hope you don't mind, but I reserved this table for you and Madam for your stay with us."

Sid smiled as he sat down. "No, this is just perfect! Thanks so much, Amani."

"If there is nothing else, I have a few things to attend to while you dine."

Sid turned back from the view to look at his butler. "I'm fine. Go take care of whatever you need to do."

"Excellent, Sir," Amani said before he walked away.

Ninety minutes later, Sid returned to his room. A quick check of the tablet confirmed that Hannah was still in the staff lounge area. He changed into shorts and a shirt before moving onto the balcony.

I wonder how her day has been,

Sid thought, adjusting his stiffening cock as thoughts of what she might be doing filled his head. Those thoughts were interrupted by a knock on the door. Grumbling, he answered it, tempted to go off on whomever it was. The words died in his throat as an eighteen-year-old Jamaican woman dressed in revealing lingerie stood there with an amused Amani behind her.

"I hope we haven't interrupted anything, Sir."

"No, nothing at all. I had just changed and was thinking about watching TV while waiting for Hannah to return." Sid glanced at Amani before returning his gaze to the young woman's barely covered body.

"I am glad to hear that," Amani said, the smile never leaving his face. He turned to the young woman. "May I introduce Cedella; she will be your suite maid for the remainder of your stay."

"Not that I'm complaining, but I don't remember requesting a maid."

"It's part of your gold membership, Sir. All permanent members receive them. If she is not to your liking, I can show you how to find another on the tablet."

"I appreciate the offer, but..." Sid struggled with how to approach the topic. Hannah wasn't going to like an attractive young woman who wore almost nothing all the time hanging around.

"I'm sure that Madam will have no issues with me, Sir," she stated, moving closer and placing her right hand on Sid's chest.

Fuck it,

he thought.

What's one more thing to explain to Hannah?

He retreated into the room, with Cedella and Amani following.

Cedella immediately began cleaning the room while Sid and Amani walked onto the balcony.

Without turning to Amani, Sid asked, "Are there any restrictions or things I should be aware of?"

"Regarding Cedella? She is solely designated for in-room service and is available to assist you in any capacity you may need during your stay. We want to ensure you have a pleasant experience, so please feel free to utilize her services fully." Sid did turn to regard his butler, then, and returned the smile the other man gave him. Sid then returned his attention to Cedella, who was moving about the suite and tidying up with practiced efficiency. As she moved, her apple-sized breasts would almost pop out of the top, and her bottoms were loose enough that Sid could see she had no pubic hair.

Sid's staring might have gone on longer if Amani hadn't cleared his throat. "There are a few things I need to show you before leaving. If I might have your tablet?" Sid took the tablet from the counter and handed it to Amani, who opened it to find that the previously grayed-out navigation was active.

Amani opened one, pointing to the different sections. "Here are the various live cameras around the resort. You can livestream any of them 24/7. Generally, there will be something going on that one of the cameras will capture. You can also access the library for each camera from here." Amani clicked on a camera where a young woman was sucking a wrinkly old man's cock and pointed to an archive folder in line with the controls. "As a rule, videos are kept for 30 days. If you find one you want to keep longer, you have a ten-terabyte personal storage area you can use." He gave Sid a quick demo on how to do just that.

"Some cameras have pan/tilt/zoom controls," he continued. "If you are the only person in that camera, you can control it." Closing the screens, Amani opened another set of menus. It had dated folders; the first stamp was from the prior day. Opening that folder, he clicked on the first video. It showed Sid and Hannah in the resort registration office. The video zoomed in on Hannah and her interaction with Sabryna. The next couple of videos were from different places in the resort where they had stopped and where Amani had abused Hannah. It appeared to Sid that the resort recorded everything that happened outside their suite.

The last file had a lock icon next to the name. "Is that the party with Harold?" Sid asked. He had tried to get details from his wife, but she'd kept changing the subject.

"Yes, Sir. The resort recorded the party because Mr. Johnston hosted it in a shared suite."

Sid tried unsuccessfully to open the folder. "I thought I had access to everything Hannah was involved in."

"Normally, all activities that Madam is involved in are recorded and available for your review. The exception to that is when you sell her services or when your sponsor is involved. In this case, you sold her services. If you would like access, please message Mr. Johnston."

Damn,

Sid thought.

I would have loved to watch that video. Maybe I will ping Harold and see if the old guy will give me access.

Sid thought.

Amani skipped over the last folder - the one for the day that hadn't yet ended -- and opened the previous tab: Terrace. "This section is where you can look for services being sold or traded." Amani slowly scrolled down the page. Sid noticed it was the first page of 3000. "The search feature is very powerful; I recommend using it to narrow down what you are looking for. If you decide to request services, use this form."

Amani turned to Sid with a solemn expression on his face. "I would advise caution and verifying the constraints and limits before signing any contract. I have heard horror stories about misunderstandings where ownership transfers have occurred, or permanent changes were made to the property that were not well received." Amani waited until Sid nodded that he understood the seriousness of his comment. "Of course, while at the resort, you can visit the Terrace in person if you choose."

Amani handed Sid the tablet and watched with an amused smile as Sid opened offers and requests on Terrace. After a short while, he said, "If you don't need anything else, I have another task to finish before my shift ends."

"Oh?" Sid looked up from the tablet, embarrassed. "Sorry, I guess I got carried away with this." He glanced around to see Cedella walking into the bathroom. "I don't think there is anything else for today."

Amani walked to the door. "Excellent, Sir. If something comes up, please contact me; otherwise, I will see you at breakfast tomorrow."

Sid opened the folder for Hannah's videos from earlier that day and found all the videos listed as in progress.

Crap, I guess I have to wait until later,

he thought, flipping to the video of Hannah at Harold's party and requesting access. After sending the request, he went back to the ads on Terrace.

***

Hannah was tired and felt nasty with all the cum leaking down her leg. Although things had wound down, a glance at the clock showed she still had a few more hours before her time was up.

I wonder what Sid has been up to?

Hannah thought, feeling slightly jealous that he might have hooked up with the woman from last night again. Lost in thought, she didn't realize anyone had approached her until she felt a hand on her arm.

"Daydreaming about all the hard Jamaican cock that you've been fucking today, Madam?" Amani asked.

"What? No, I was thinking about Sid."

"Oh, you don't have anything to worry about there; he is well taken care of, Madam." Amani's smile grew as he saw her eyes widen slightly. "Now, are you ready to return to your suite?"

The thought of a hot shower drove her worry about Sid out of her mind. "Yes, please." She started to rise from the lounge when he stopped her.

Amani looked pointedly down at his own crotch. "There is just one more thing to take care of before we leave." Hannah groaned internally but moved to her knees in front of the black man, pulling his semi-hard cock out of his pants. Without waiting, she sucked and licked the head and shaft until it was rigid and slick with saliva.