Doubling Down Into Diapers Chapter One (Patreon)

Sorry it took so long to get this done, everyone. I had a major home improvement problem this week and I haven't had time to deal with much else for the last couple of days... hopefully, I'll be able to update this story on a more regular basis from now on.

As always, if you're enjoying the story and you want to see more like it in the future then please don't forget to hit the like button and leave a comment below.

Sipping her drink and breathing steadily, Vanessa tried to clear her mind and put her anxieties to rest. It was a ritual she went through before every game, a way of focusing herself and suppressing any remaining fears she may have had. Ordinarily, she was cool as a cucumber by this point in the evening... but tonight was special.

     Beverage in hand, she wove her way through the crowd, pretending not to notice the glances she was getting. The outfit was carefully selected, and not just for it’s distracting effect in the heat of a high-stakes game... with no sleeves (or much of anything else) to stash cards in, it made it more difficult for anyone to accuse her of anything... untoward.

     She sipped her drink, selecting a slot machine at random. It was the most important part of her ritual-- she settled back into the seat and fed her money into the slot, ready for the one spin that would predict her fortunes for the evening.

     Hitting the button, Vanessa watched the characters spin on the screen, the lights flickering across her finely chiselled features, letting the alcohol settle into her belly and fill her with it’s relaxing warmth.  

     The symbols fell into place, the machine binging pleasantly as three cherries clacked down into a neat little row, a couple of coins clanking into the dish before her. A good start for most people... But it was a frown that Veronica wore when she rose from her seat and left, not even bothering to collect her winnings. Not exactly a great omen for tonight, she thought, sipping her drink and making her way through the lounge. Tonight, she needed to make a big score, and for that, she would need more on her side than just luck.

     She swayed her hips as she walked, wiggling her butt in just the right way to attract attention, a move she’d practised until it was as natural as breathing. She prided herself on her body, worked hard to keep it looking good... and she was an expert on using that to her advantage.  

     Draining the last of her drink, she left the lounge and entered the casino... but she didn’t make her way to one of the tables on the floor. Tonight, she’d manage to score an invite to a private game with some of the wealthiest people in the city. A rare opportunity, one she had to hustle her well toned buns to get... and one fraught with peril, even for someone with her skill. The host, William J. Howard, was both very wealthy and generally considered one of the best amateur poker players in the country... as well as a well know eccentric, with enough strange rumours swirling around him to keep TMZ busy for years. He was also quite handsome, and very single ... Vanessa smiled to herself-- she was always in the marketplace for a new sugar daddy. Maybe if she wasn’t lucky in cards tonight, then perhaps they could...

     She forced all that out her mind, showing her invitation at the desk and gaining access to Howard’s private elevator, and moments later she was on her way up.

The game went on into the night, the players growing louder and more rowdy as the evening wore on... all except Vanessa, who stuck to ginger ale, and Howard himself, who maintained both his sobriety and  his money. She played smart, utilizing the bottom dealing and slight of hand tricks she’d learned from her father and uncles sparingly to accumulate a modest pile of winnings that grew by inches as the evening wore on.  

Vanessa played smart, and cheated smarter, her small pile of chips growing fat in front of her. While the other players consumed larger and larger amounts of booze, most leering openly at the flesh generously displayed by her outfit, she just smiled and pretended she didn’t notice the looks she was getting when she leaned forward far longer than necessary to place her money in the pot, or sat sideways in her seat to reveal almost the entirety of her smooth bare legs.

Of course, the extra attention meant she had to be extra careful when she “tilted” things in her direction, but her hands were nimble and quick, the cards fitting perfectly into her palm, and she transitioned them between her hand or the deck and back again effortlessly.... all while building herself a nice pile of winnings.

At last, the evening was coming to a close, with the other players having either cut their losses or lost their chips entirely. One by one, they drifted away from the table, until it was just Vanessa, Howard, and a big pile of cash... and she intended to work him with everything she had.

She batted her eyes and smiled invitingly, flirting shamelessly, doing everything in her power to keep him focused on her face, her tits, her legs... anything but her fingers, which massaged the deck in her favour, putting the cards she wanted into her hand when she dealt or deftly cupped a spare ace, king or queen in her left palm, ready to be deployed when needed.

The game went on, the betting growing faster, more intense... Vanessa’s eyes gleamed as she gazed into the pot, trying to calculate it’s worth, her soft, pink tongue wetting her lips as she studied her cards and watched Howard make his bets, determining that either he had a solid hand himself-- or that he was a calculating and fearless bluffer.

     With an ease that was born out of hours of practice, she swapped the ace she had palmed for a lowly two before reaching out to drop her chips in the pot...

What should happen next?

Vanessa gets caught cheating

She gets away with it... but loses the hand anyway