"Hmm.." Ross took a second to collect his thoughts, before slowly getting up from the chair and walking the few steps needed to reach Erika. His mighty meat swinging with each step, the movement causing Jessica to focus on it.

"I see... Very well, It'll be removed from the list of rules". Ross turned around and looked Jessica in the eye.

"Now sit back and enjoy the show" Ross grinned before returning his focus fully on Erika.

----

Mike sat at the pool bar and enjoyed his highball while watching the sunset, this was truly relaxing. He didn't mind having to wait even a few hours on Jessica working with his uncle, if he could just sit here in peace.

A very rosy cheeked Jessica came walking out of the nearby reception building towards him. Mike just smiled at her, as she approached, noticing how she looked quite tired and thus revised his plans for the evening.

"So.. how'd your first work day go?".

Jessica just sighed loudly and ordered three shots of tequila.

Ross took that as a sign to not prompt further. His uncle didn't get to own a Resort such as this one by accident. Mike had heard the stories of how Ross overworked and pressured his workers. Nothing too serious, but enough that people knew that they had to perform while at work. Which was probably what had happened to Jessica, he imagined.

As the shots arrived, Jessica immediately downed one as she slid one of the remaining two towards Mike.

"You want one?"

Mike shrugged and barely manage to grab onto it before Jessica had downed another one and ordered two more.

"We need to talk... This work is exhausting..."

Mike raised his eyebrows, as he was extremely surprised at how much non-physical work could exhaust someone in only half an hour. No matter, he would let Jessica decide this herself, and support her in the endeavor, it could be her chance to get a way into a good company, with uncle Ross as a backer, a lot of doors would be open to Jessica.

A lot of different thoughts went into Mikes head, as he considered what Jessica could've been doing, that would've exhausted her this much in only half an hour.

He studied her face, as she looked down into the now empty shots glasses, and could only come to the conclusion that it was the all the new information she would be getting the first few days.

"So.. there's a lot of information to take in. His current strategy isn't a good fit with his plans expand his business".

Mike just sat and listened as Jessica ranted on about everything, smiling slightly at himself. It seemed like even though Jessica was exhausted, she liked the challenge.

She had always been an ambitious young woman, he liked that about her, it was something he lacked himself. Even if he did his best to excel in his craftsmanship, he didn't do it for prestige, money or power, it was purely for his own enjoyment, well mostly, he did have to pay his bills and money could get him things - like this vacation he paid for.

He mistook the fire in her eyes as purely being fuelled by her desire to rise the challenge, mostly mistaken by the indecent nature of the challenge given to her.

---

As Jessica once again looked at the ceiling during a sleepless night, she went over the 'work-meeting' today. Surprisingly Ross actually wanted her to look over his strategy and how to fit it with his plan to expand the resort.

It certainly didn't help with her focus, that she had to finish reading the executive strategy report while watching Ross abuse Erikas body, as he kept pumping and dumping his seed into her multiple times, all while Jessica tried to understand some of the more complicated points of the report, trying to make meaning of his grand plans to expand and become a leading resort here in the Caribbean.

Heat returning to her cheeks, at the mental image of how the stoich Erika had melted completely in Ross' embrace, as her silky voice moaned repeatedly throughout the ogasm filled reading session.

Jessica shook her head and refocused her thoughts. Unfortunately she couldn't find a way to modify the current strategy to be good fit to his desire to further expand his resort.

While his bottom line had been expanding slowly and steadily the last few years, he would need to get further investing or backing in order to get the proper funds for the expansion he wanted. Even though Ross' resort was quite large, the resort was merely a drop in the ocean for the Caribbean resort business.

Ross' resort hotel was catered towards a lot of different customer segments, from slightly wealthy businessmen to families looking for a all-inclusive getaway, unexpectedly the profit margin wasn't actually that high, hovering only around the low side of 6%, as he didn't attract the whales nor cash-cows.

He would need some sort of value proposition to set himself apart from the nearby resorts, something with a fresh spin, that could attract both potential investors and present the grand concept which he envisioned.

Jessica sighed as she mentally prepared herself to another sleepless night. She would need to read through countless of yearly reports from the nearby resorts, going over marked trends and so on, before she was ready to give any advice or create any strategy.

With renewed determined, Jessica got out of the bed and went to press the power button on her laptop.

--

Jessica once again found herself in the meeting room, finding the decoration the same as last time. This time there was a different vibe, as a different receptionist had lead her to and now opened the door for her to the meeting room.

Ross and Erika were leaning over the table, eagerly discussing a detail in what seemed to be a report, so absorbed that they didn't register her enter at first.

"Greetings uncle Ross", Jessica prompted as she stood behind the player chair opposite of him.

"Ah Jessica, good of you to join us", Ross leaned back as he motioned her to sit down.

Silence took the room, as both Ross and Erika looked to Jessica to start the conversation.

"I believe it's possible, your grand plan that is~" Jessica started as Ross tilted his head, interested in hearing more.

"However... The current strategy isn't feasible. At least not with the timeline you've expected. I believe If you want the project to start, no one would approve nor invest in any of your grand plans without having seen a concept of it working beforehand."

Upon hearing that, Erika was about to interrupt Jessica.

"Not... That the current strategy isn't sound and ensures the continuous success of the resort". Jessica looked towards Erika, who glared back, but nodded as to agreeing to her statement.

As she had expected, it was likely Erika who had developed the current strategy, and she would have to be the one to be convinced of her newly created strategy.

Jessica then continued to explain her new strategy, and how she wanted to host a concept stay, where esteemed guests of his could explore and get a taste of his planned expansion and how he would be able to get major investors.

--

After almost twenty minutes of Jessica presenting her strategy of how to she wanted to implemented everything, going over all her found facts and concerns, as well as all the details that they would have to address at a later date. Ross almost couldn't believe it.

While Erika had challenged Jessica a few times during the presentation, he himself only noting a few points still needed to be ironed out, he was now convinced in her skills. Extremely surprised at her capability in creating such a complex and seemingly feasible strategy in such a short amount of time.

What a rough diamond he had been given. He would spare no effort in grooming Jessica to make sure that she, body and mind, would be the perfect addition to him and Erika.

He had been sceptical at first, but now completely convinced, Ross have an almost villany smile, as he couldn't contain himself any longer, he excitedly stood up, causing the chair he previously sat on to fall backwards, startling both Erika and Jessica, as he grabbed Erikas hand and pulled her in front of him, pushing her down on the table in front of him as he started to unbuckle his belt.

Erika caught on quickly, having sensed his excitement building underway and acted in accordance to his wishes, as she removed the lower half of her uniform while still half lying on the table. Not managing to undress completely, before an impatient Ross pulled her lingerie to the side and plunged into her depths.

"Aah!" was all Erika could muster, as waves of pleasure overtook her previous thoughts.

Jessica however, were not so prepared, as she just speechlessly looked at the now corpulating pair.

Ross continued to grunt as he grabbed Erika's hair, pulling her head back and up from the table.

"So Erika, I believe we're agreeing on letting Jessica try this Gambit?".

"Yes.. YES... YEEEEES." Was the only response from Erika, as he continued to fuck her.

Jessica tried to calm down, having reached her goal of getting Erika to believe in her strategy, maybe with a little convincing from a pounding Ross.

She felt herself getting slightly aroused, instead of embarrassment at the sight of Ross fucking in front of her.

The complicated knot returned once again, as to how naturally she had come to accept this whole ordeal, with the betting, rules and everything. Frankly it scared her quite a bit. If she could accept this so easily, how fast would she be corrupted by Ross?

Before she could finish her train of thought, a chill went down her spine at Ross' next sentence.

"Oh.. And you're gonna be the prize for the concept stay, that's how I'll use my additional rule".

--