After such an eventful day two of their vacation, Jessica couldn't sleep at all, which wasn't really that surprising, considering the drastic turn her life had suddenly taken. From being taken advantage of, losing a bet and now having signed a contract that would likely form her future many years ahead.

 

After the dinner Mike and Jessica had retired to their room, where they talked about the order of which they would visit the resort facilities over the next few days. While they small talked, she vaguely explained her whereabouts during their time apart, while omitted the juicy details completely, especially about her time in the onsen.

 

Almost immediately after their talk, Mike had been out like a light, he had always been a quick and deep sleeper and today was no different.

 

Thus Jessica was laying awake, staring at the same ceiling from when she woke up earlier from her post-orgasm blackout, this time a lot less confused, but with just an uncertain future.

 

Again she contemplated if she could have done anything different. Even if Jessica had won the last bet while sitting on Ross lap, enduring the humiliating grind of his rod, would she be able to explain everything to Mike in an way where they could continue their current relationship and grow it together? She knew that trust was a fragile thing, once is it broken, it will never come back to its original shape.

 

And even if Mike didn't consider the current events to be some sort of betrayal, could Jessica even live with herself, having done what she'd done.

 

Many similar thoughts came and went during the restless night.

 

One thing was certain however, she had signed that contract, and from now on, she had to navigate the narrow path between bending the rules just enough to not break the the contract, but still enough to come out on top, such that she had the options to tell Mike everything on her own terms.

 

Unfortunately for her, she didn't have a copy of the contract, but luckily her memory was quite keen, and she could recall the content almost flawlessly, maybe not word for word, but enough to be able to form a plan that would allow her to come out on top.

 

And thus she spent the long night scheming.

 

--

 

The next morning, Mike and Jessica was eating at a table in the brunch area.

 

"So, when exactly are you going to work today?" Mike asked.

 

"Hm, good question, I actually don't know." Even with Jessica laying awake and spending all her time pondering about the contract, she hadn't come up with any excuse as to why she shouldn't meet up with Ross for pretend-work each day due to Ross' already told lies.

 

But that didn't worry her too much, as Ross was the one who offered the contract. Thus it was his problem, if they didn't meet up and discussed anything within 24 hours. And if that happened, as she interpreted the contract, the current rules were the ones that would be active. Thus she didn't spend more time pondering that angle.

 

Also while the contract didn't mention anything about her and Mike just suddenly leaving the resort and abruptly stop their vacation, except it no longer being active, Mike wouldn't likely accept that decision, as he was quite thrilled to explore the resort and enjoy the vacation, so Jessica had to keep up the facade, at least for now.

 

Jessica had devised a reactive strategy, as it was very much depending on how many of his lewd rules she had to abolish, she considered using one of her two initial rules to do something about the daily meetup. When she signed the contract, she knew that she had a slight disadvantage due to the rules already being against her. Thus she had to at least establish a rule which Ross could violate, so she could gain leverage to abolish the already existing ones.

 

She was prepared to let the existing rules stay, if she could get Ross to be caught with his hands full of her tits as one of the first rule violations, she could control the flow for the rest of the continuous bet. It was all about initially creating violatable rules where Ross could mess up, thus she couldn't necessarily just abolish the two existing rules and be happy with that, she had to go on the offensive as well.

 

"Ah, there's Erika, maybe she knows" Mike waved for Erika to come over.

 

"Hello Erika, me and Jess was wondering when she had to work for Uncle Ross today, as we wanted to explore a bit of the resort today, do you know when Ross is expecting her?" he continued when Erika came within speaking range.

 

"Good morning Mike, Good morning Jessica, unfortunately no, I do not know when Ross is expecting her, however I do have his schedule with me." Erika proceeded to pull out a tablet and tapped it a few times.

 

"It seems", Erika continued while swiping a few times on the screen "that he has quite the busy schedule today, so he only has time for an appointment for half an hour time during dinnertime. Will that work for you?". She put on a professional smile and looked towards Jessica.

 

Jessica was hesitant to reply as that didn't sit well with her, why would Ross make her sign the contract and then not have time to discuss the details with her? As far as she knew, he should immediately be trying to finalize the details of the rules, and afterwards immediately try to take advantage of the rules to do lewd things to her.

 

"That's perfect then!" Mike answered enthusiastically , before Jessica could give a reply, "then we have plenty of time to explore and unwind today, and we can have a late dinner instead, maybe with some drinks after you've worked with uncle".

 

"It's settled then" Erika tapped the screen a few times and put the tablet away, "I've updated his schedule, meet me at the reception at the scheduled time. I'll go inform Ross immediately, enjoy your food". She bowed before walking away.

 

Slightly annoyed at the development, she went along with Mike's plan, not wanting to disappoint him nor making him suspicious of uncle Ross having ulterior motives.

 

"So, what do you say we go for a beginner golf course, eat lunch there and then unwind in the onsen afterwards?". Mike was quick to suggest a plan for the day, one to which Jessica smilingly accepted, despite everything that was going on, she looked forward to seeing all of Mike's failed swings while enjoying quality time with her boyfriend, and she wouldn't let Ross come between Mike and her enjoying their vacation time together.

 

--

 

Erika knocked on the door twice before hearing the commanding voice of Ross "Yes? Come in".

 

As she entered, she could see Ross standing up and staring out the window of his office on the second floor, which was looking over the pool area of the resort. As he turned around, Erika entered the room, closed the door behind her and approached the expensive looking desk.

 

"I've scheduled an appointment with Jessica as requested, it seems like she was deep in thought when I made the suggestion, Mike however jumped on the opportunity, making it natural for me to schedule the desired timeslot". Erika made her report, while looking straight ahead at the empty office chair behind the desk.

 

Ross proceeded walk around his desk to stand beside Erika, who was still looking straight ahead. "You did? Excellent work Erika, you're a natural". Erika's natural and stoic attitude broke, a small smile forming on her face as Ross continued to walk around her in a half circle.

 

"I believe you deserve a reward" Ross voice boomed, he had now made a full circle around her, and was standing in front of his desk, leaning back onto it. "On your knees" he commanded and Erika quickly obliged, kneeling down in front of him as he unfastened his belt.

 

Erika knew what she was supposed to do, and proceeded to help him lower his trousers and boxers and started to work on his flaccid beast, using both hands to slowly stroke the shaft while she prodded the tip with her tongue. "If everything goes according to plan, you'll have a playmate before you know it" Ross continued.

 

After a half-moaning exhalation, Erika eyes widened as she continued stroking the shaft with newfound energy, but with one hand going towards her own lower folds, to ensure her own pleasure. "(Fuck... Jessica's the best thing that's happened in the last ten years!)" was all that Erika could think, before trying to shove the now semi-erect beast down her throat.