Jessica stopped breathing for a moment, as she let that sink in.

"What do you mean, I'm the prize?".

"I meant exactly what I said, you're going to be the prize for the winner of the concept stay." Ross elaborated, still feeding Erika his rod, but stopping before continuing. "What could be a better prize, than the one who came up with the concept itself?".

Jessica couldn't believe her own stupidity, once again she had thought, that she had found a way out, that showing her brilliance and strategy would lead her out of his filthy grip, only to be pulled in tighter in his lewd web.

Ross' Grand plan consisted on expanding his resort to become an exclusive place for gamblers. A plan which wasn't completed by just building a casino. Instead he wanted to create a place in which gamblers do not only feel only the luxury and exclusiveness of being on a resort, but where they can be and do things they cannot normally do.

A haven for all gamblers, where they can satisfy every single possible fetish, somewhat within the legal boundary of the law. From the feeling of owing another person as a slave, gambling for more than mere money, where pleasure, sin and business can coexist and thrive.

Whether that be something as simple wearing a mask, where you as a celebrity can stay anonymous, where it's possible to get a feeling of power, that wouldn't elsewhere be possible without breaking the law.

Jessica would have to use all of the common mechanisms that makes the rich people feel powerful, she would have to create a brand that cater to every gamblers dream, where they can win more than just money.

Pulling herself together, it was no matter, she just had to come up with a way to set up the concept for his grand plan, in a way where you couldn't just straight up win by just paying enough.

"If you don't want to end up as the prize of some rich old man, I suggest you come up a concept that is both enticing enough to attract investors and one where you don't sell yourself short". Ross deep voice brought her out of her daze, as he grinned at her before he continued pumping into Erika, as her muffled moans started to fill the room again.

Stunned at the brazen display of lewd action, Jessica just watched on, unable to keep her eyes of the moaning Erika. A grinning Ross finishing inside Erika with a satisfied huff, releasing her from his grasp, as he slowly pulled out and sat back down. As he sat down again, Erika started cleaning his beast with her tongue.

Jessica cringed involuntarily as she imagined herself standing on a stage in a skin tight red dress, looking out towards the audience but only seeing the bright lights from the projectors lighting the delicate details on her dress, as the loud shouts of numerous men bidding in an auction for a night with her.

Any moral scruples be damned, Jessica glared defiantly at Ross, as she already had a rough idea on how to implement a system for the concept stay. She would be borrowing the recipe to success straight from how cults and sects worked.

"Oh!, and also, we've only got a single minute left today, and you still have to pick a card game to play" Ross blurted out, looking very satisfied with himself.

Jessica slightly panicked, as she had completely forgotten about that rule, considering her her lack of sleep and now undivided focus on creating a system for the concept stay, she was afraid something like this would've happened.

She could only sigh loudly as fate and a simple card draw for highest card would determine the winner of the daily game today.

With a final slurp Erika stopped cleaning Ross and sat down at the dealer position before opening a freshly deck of cards, creating a fan of faceup cards to show both of them.

Somehow still managing to radiate professionalism as a dealer, as if she haven't just sucked dick for the last few minutes, and the ones before that being plowed hard, she masterfully shuffled the cards and created yet another fan of cards now only face down.

"Ladies first" Ross prompted as gentlemanly as he was able to, as his private were stilling on show.

Jessica took a random card in the middle of the pack and flipped it over.

"King of hearts".

Jessica smiled as she leaned back, sure of her victory.

Ross calmly took his time to put his pants back on, before he stood up and offered her another of his wolfish smiles.

"How about we double the bet?"

Another chill went down her spine, as Jessica quickly suspected foul play, seeing her chances to win quickly slimming, even though Ross had to get an ace to win or a king to draw. Why else would he want to double a bet with her already having drawn a king?.

"What's the catch?"

Jessica frowned, she knew that he would never take a disadvantages bet.

"No catch, I'm simply feeling generous today", Ross only continued to grin as several seconds went by. Jessica wasn't in a mood to gamble more today, and she wasn't feeling particular well due to her lack of sleep.

"I'll kindly refuse this time".

"Very well", Ross said before picking a card.

"Huh, what a shame", Ross sighed and threw the card on the table.

A draw. Jessica frowned as another king was shown, this time the king of spades. She was slightly disappointed at the prospect of not winning, even with the odds stacked heavily in her favour, but alas such is gambling.

--

Jessica headed straight to hers and Mikes room. Going straight to sleep, having told Mike that she wasn't feeling too well since last night and thus had hardly slept.

When he got slightly angry at her for working while feeling unwell, she could only smile at him for caring such much for her health, giving him a kiss before going to bed. Mike sighed, as he knew reprimanding her even further was a lost cause, and instead went down to the bar again, letting Jessica sleep.

Mike had a quiet night talking with a few other guests, having more than a few drinks and was about to call it a night, when suddenly Erika sat down next to him.

"Hey Mike, how's the resort treating you?"

"Very well, thank you for asking".

Erika only smiled sweetly in return, and maybe it was the alcohol talking, but he swore she moved a bit closer to him.

She was not wearing her traditional work suit, but instead wore an elegant yet simple strapless blue dress, which looked quite lovely on her.

"So Mike, tell me about Jessica, how'd you meet?" Erika inquired.

Feeling talkative, Mike eagerly responded.

"Huh, actually it's a common story. When I was doing the last part of my thesis, I went out drinking a lot on fridays, and thus met Jessica at one of the bars".

Mike were reminded of his past, smiling slightly at the memory.

"There she was, the center of the party with a perfect hourglass figure and emerald green hair. Every guy at the bar were stealing glances at her, when suddenly one of my friends had the brilliant idea to dare me a crate of beers to go talk to her and get a kiss. And well... Being drunk I figured why not."

Mike laughed as he continued.

"Funnily enough, the first thing she said to me was exactly that. 'So you're friends dared you to go talk to me, huh? Hah, well let's them regret their bet then!'.

She always had a thing for betting, and to my luck, it meant that bet went my way". Mike grinned widely.

Erika smiled coyly at Mike, before putting a hand on his leg.

"Haha, that's a cute story Mike... But to be fair, that sounds nothing like a common story". Using her other hand to to cover her mouth to muffle a laugh.

"Seems like she has a thing for betting?" Erika inquired.

"Oh.. You have no idea". Mike responded, slightly shaking his head.

"Hey... What do you say, we try to create that night and bet again?" Erika suddenly asked, Mike only now noticing the warmth of her hand on his leg, as it crept slightly upwards. Feeling his excitement rise at the womanly attention.

"Erika, what ar..?"

"Hush Mike, I've seen the way you look at me when I walk away, I'm know when I'm wanted."

"I would nev.."

"I know Mike, you would've never betray Jessica, which is not what I'm asking. As you might've figured out, I'm quite happy with your uncle, thus I'm not seeking another partner."

Mike raised his brows at that statement, slightly confused but still feeling his exhilarated at the touch.

"I'm afraid I don't quite follow, Miss Erika".

"Your uncle is quite impressed with Jessica's ability, and frankly he would like to employ her to help with growing his business. I know this doesn't sit well with your vacation plans, but as you probably know, this opportunity doesn't come often. And as Jessica's partner I know you would like to see her get success in her career".

Determined to help Jessica out with her career and their future together, he motioned for Erika to continue.

"However... there's a catch".

Mike held his breath as Erika's hand brushed over his crotch, waiting a moment before she continued.

"Both your uncle and me are running this resort by mixing business with pleasure, as such, it might be... required for Jessica to engage in indecent activities at time".

Shocked at the revelation, Mike was about to storm off, but a hard squeeze at his private parts kept him seated.

Erika turned around on her chair and looked him straight in the eye, leaning forward she used her other hand to caress his now growing manhood through the fabric, still looking him in the eye.

"Thus Ross and me however, enjoy what you call swinging among other things."

Mike held his breath as he felt his boner grow with her touch.

"While it wouldn't be required for Jessica and you to engage in... Swinging activities. I would like to propose that you two have a long talk about your future. Erika paused as she looked down at his crotch.

I've seen and.. felt your... lust." Erika dragged out the last part of the sentence, now giving him a few strokes through his pants, now keeping eye contact with Mike.

Only feeling the moment and pleasure, Mike didn't respond initially, thinking back on the look on both Jessica and Ross at they met at first.

It all made sense to him now. When Jessica had somehow cured his uncle of impotence, his sexual interest in her was of course a given. How come he didn't give it a thought earlier? Was he to focused on them enjoying the vacation? Ross was probably extremely interested in keeping her around, afraid of going impotent again if Jessica left.

Mikes arousement suddenly mixed with embarrassment keeping him from facepalming at the realisation.

Shame washed over him, as his guilt flared to life, a deep shame for not flat out refusing was was going on. For the current situation he was in, having another woman indirectly stroking him, he was essentially cheating on his girlfriend.

Yet he sat completely still and looked into Erikas eyes, conflicted as he enjoyed the pleasure of her soft hands through the fabric.

"I..." Was all Mike could get out, before the slightly squeezing hand of Erikas went to his zipper and unbuttoned his pants, the other hand following up, now caressing his manhood through his boxers.

Once again his mind wandered, as he remembered himself panicking at getting an erection of seeing Jessica and his uncle's bodies touching. When he a few days ago came out of the shower stalls, and Ross was more or less pushing Jessica's body up against the pool wall. His arousal spiking as he remembered seeing her not resist, but instead seemingly blushing heavily at the attention.

His mind quickly brought back to the current situation, as he could feel his lust build up, tension rising as he felt himself getting closer to climax.

"Mike... You should relax and enjoy yourself" Erika whispered, sliding the chair even closer, now talking directly into his ear, Mike now feeling the warmth of her breath on his skin, he could feel himself almost climaxing.

"Wait... Please..." Mike pressed down on her hands, stopping her completely. Erika didn't resist his attempt, and paused her actions.

Giving himself time to calm down from his high and almost climax, Mike took a few deep breaths as he collected his thoughts.

"Let me talk to Jessica, before we cross this line even further".

Erika only smiled at him slightly before withdrawing her hands, now sitting up straight in her chair, turning sideways. That gave Mike an opportunity look at her profile, as he took in the gorgeous proportions of her body.

Erika used her hands to pull up her hair and neatly tucked it into in a bun.

"You know.. Maybe a small bet could spice up your relationship? See if the swinging lifestyle could be for you? It doesn't have to be anything big Mr. Mike".

Erika nonchalant said, turning her head to look him in the eye again, as she finished tying her hair.

"(A bet?)" Mike thought, scratching his cheek, as he gave it some actual serious thought "(Maybe that doesn't sound too bad, Jessica would love to do a bet.. But do I really want to see her do indecent things.. Potentially with other men?)". Mike felt a pang in his heart, as he started imagining the previous scene with Ross and Jessica. The feeling of guilt coming over him, for not stopping, whatever what had happened with Erika earlier.

Yes, it was every mans dream to have a harem of multiple women to pleasure them, and he was no different. But he hadn't even considered swinging to be a thing to consider. How would Jessica even react to what had happened here?. Would she feel the same?.

Putting his guilt aside from his current actions, he tried to imagine what Jessica would feel about Erikas proposal.

"(Who am I kidding?, I already know Jessica answer to this. Her ambition and love for betting would probably be enough on its own.)".

Seeing a sudden tequila shot being poured in front of him, Mike looked up to see the bartender give him a wink.

"(Ugh.. At least I now know that the bartenders are big voyeurs)".

Hoping he wouldn't regret his decision in the future, slightly frustrated as a stray thought made him wonder if he could get Erika to finish him off before going to bed.

"What the hell.. I'm in.." Mike said, as he downed the shot. Letting the burning sensation take his intrusive thoughts with it.

Erika with pleased expression and a raised shot-glass, nodded in return before taking the shot in turn.

--

Full list of rules

• Jessica must always refer to Ross as her uncle.
• Ross can fondle Jessica's tits at any given time, as long as Mike doesn't notice.
• During the daily meetup, Jessica must watch as Erika services Ross.
• Ross is not allowed to actively touch Jessica during the daily work meeting.
• Jessica is only allowed to relieve her sexual tension during the daily work meeting.
• During the daily work meeting, Ross and Jessica must play at least a single round of any card game of Jessica's choosing. The winner gets to add or remove a rule.
• Jessica will be the prize for the concept stay.