The Man’s Challenge

The red dice flashed across the green table in an instant. They bounced off the far side wall dramatically and fell to their resting place. Six and two.

“Eight!” Eight pays out!” The stickman bellowed.


“Oh fuck yeah.” Muttered Jessica as one of the dealers plopped a fresh two-hundred dollars worth of chips in front of her.

“Fuck yeah is right. The table is hot!” Replied her friend Anya, significantly louder. She was pressed up against the table to Jessica’s left and a huge grin spread across her cute face as she watched the dealer doll out her portion of the winnings.

“Anya! You’ll jinx it you idiot!” Said Kim, standing to Jessica’s left. No chips for Kim this time, she was still waiting for a six to reappear. Jessica didn’t feel particularly bad for her though; considering Kim had landed a near eight-thousand dollar profit earlier in the day off a parlay she made on a basketball game.

“Relax Ms. Moneybags.” Said Hanna, standing a few feet away from the table and looking at her phone. “We’re all still up big. Even if you crap out on the next roll.”

“Oh now you’ve fuckin done it!” Kim retorted.

The stickman pushed the dice back over to the girls side of the table in front of Kim. She picked them up and swiftly tossed them to the far side again. Three and four. The crowd of ten or so at the table groaned in unison.

“You see! You see what you did!” Kim cried over her shoulder at Hanna as the dealer scooped up her bet from the pass line.

“I’m soooo sorry.” Hanna said, her voice dripping with mock sympathy as she rested her hands on Kim’s slender shoulders. “I hope I didn’t ruin your last weekend on freedom.”

Kim’s face relaxed and she leaned back into Hanna’s arms as the other woman wrapped her arms around her in an embrace. “Of course not. This weekend has been perfect and you’re all perfect too!”

Jessica smiled at her friend’s dramatics. She had to concur, the weekend had been perfect so far. The four of them had landed in Vegas for Kim’s bachelorette weekend yesterday. They had been friends since college. Kim and Hanna had been roommates their freshman year and so had Jessica and Anya, all on the same dorm floor. The four were soon inseparable and they lived together in an off campus apartment for their last three years of schooling. They had stayed in touch since graduation but Kim’s engagement to Mark had been their first excuse to all meet together in person again.

And Mark was a very lucky man, thought Jessica to herself. Kim was a knockout. A slender Asian woman of Japanese descent, she was blessed with a gorgeous face marked by soft features, deep dark eyes, and long black hair that fell almost to her ass. Today she was rocking a sparkly silver mini dress that cut low between her small breasts. The dress, as well as Kim’s eyes, twinkled as she twirled in Hanna’s arms.

Hanna was also Japanese and was every bit as svelte as Kim. But Hanna’s face was more angular and the muscles of her arms and legs more defined, evidence of her active lifestyle of biking and rock climbing. Her shiny black hair was pulled into a high ponytail. Jessica thought that the gold mini dress she was wearing contrasted pleasantly with her friend’s silver.

As for Jessica herself, she was also Asian, both her parents were born in Taiwan. However, she was a little bit shorter than Kim and Hanna and definitely curvier. The mid-length red dress she had chosen for tonight clung to her body tightly, accentuating her heavy D cup tits as well as her wide hips and plump rear. Anyone lucky enough to have gotten a peak underneath her outfit would see she was wearing a set of lacy red lingerie to match her dress. Jessica looked hot and felt hot.

But maybe, she thought to herself, not quite as hot as the final member of their group. Anya was an adorable Indian woman. She was the shortest of the group, barely an inch over five feet tall, with soft light brown skin and wide innocent looking eyes. Her dress, on the other hand, was significantly less innocent. It was a sexy dark green piece that barely covered her pert little ass and showed plenty of cleavage from Anya’s perky apple-sized boobs. Helped, no doubt, by the fact that Anya had chosen to skip a bra today in lieu of glittery star stickers to cover her nipples. If she had to take a guess, Jessica would presume Anya had also foregone panties for that evening as well.

Yes, the foursome was quite sexy, and four sexy women let loose in downtown Vegas could be dangerous enough as it is. However, there was something else about this group that made them a terror in a town like this. A detail the average observer would never guess. That detail was that all four of them were incredibly sharp gamblers.

Anya’s family had been majority owners of a casino/resort that was located less than an hours drive away from their college campus and the group had regularly spent weekends there. At first, it was just a place to drink underage where the staff would turn a blind eye to their discretions. But Anya had spent plenty of time amongst the gamblers growing up and was already skilled in many of the various games and she shared her knowledge with her companions. It didn’t take long for the group to begin sidling up to the craps table or indulging in a few spins of the roulette wheel.

But their favorite was trying to join the Texas hold ’em tables. The young women became incredibly good at reading tells and playing off the other gamblers’, mostly older men, inclination to underestimate them. By the time the gentlemen, who had so graciously allowed them to join their game, realized that their “beginners luck” wasn’t wearing off any time soon, they could be hundreds of dollars in the hole. When they graduated, the foursome had amassed quite the reputation as card sharks around their local casino. And several years later, when choosing a spot for Kim’s bachelorette weekend, Las Vegas was the obvious choice.

“Alright. Time to step away.” Jessica said as she scooped up her chips. “I know a table that’s about to hit a cold streak when I see one.”

“Agreed.” Said Anya, following suit. “Plus, I’m ready to hit the clubs!”

“Ooh! Yes let’s dance!” Kim squealed excitedly. “But can you guys cash me out? I wanna go check and see if the line on the Lakers game has moved at all.”

“Yeah I got you.” Jessica replied. She picked up the last couple of chips Kim had remaining.

“I’ll go with her. Make sure she doesn’t get too excited and blow her dowry.” Hanna said.

“Oh fuck you!” Said Kim. “I’m a responsible bettor!”

“Mmm hmm. Totally.” Hanna replied sarcastically before looking back at Jessica and Anya. “We’ll meet you at the entrance in just a bit, okay?”

“Sounds good!” Anya replied for both of them. “You gotta hurry though! I’m ready to shake what my momma gave me!” She accompanied her words with a quick shimmy causing her healthy tits to shake freely from side to side.

“Me too darling! We’ll be fast!” Kim said over her shoulder with a big smile as she and Hanna started heading towards the sportsbook. She also made sure to wiggle her cute ass in Anya and Jessica’s direction, earning a giggle from Jessica and a short burst of applause from Anya. Hanna just rolled her eyes but couldn’t hide her smile.

Jessica and Anya walked over to the cashier station and exchanged their chips for cash. Jessica had been the one designated to carry the parties’ cards and cash for that evening and she carefully organized each woman’s winnings in her purse to keep them separate. “Hmm. Maybe I should drop the purse off at the hotel and we can each just grab our own ID and credit card.” She thought to herself. “I think we’re done gambling for the night.” She was wrong.

While Jessica was still pondering what she wanted to do with the purse, she realized Anya had wandered off somewhere. Jessica scanned her surroundings for a second and quickly located the tiny brown woman standing over by a row of brightly colored neon slot machines. She was talking to a Man.

Jessica opened her mouth to call out to her friend, but then the Man turned his gaze from Anya to her and the shout froze in her throat. He was certainly handsome. His simple black suit was sharp and well tailored to his powerful frame that towered over Anya. He had a full head of thick brown hair and his face was pleasant, with a light five o’clock shadow. But it was his eyes that caught Jessica, even from a distance. They were a lovely blue color and they seemed at once both hard and unyielding, but also inviting. It was the Man’s eyes which held Jessica in place for a moment, and then instructed her to walk over and join Anya in front of him.

When she arrived the Man turned back to Anya for a second. “And who might this be? One of your friends?” He asked. His voice was deep but clear.

Anya turned to see Jessica. She looked almost dazed. Her eyes were wider than Jessica had ever seen them and there was a slight tremble to her bottom lip.

“Umm yes this is my friend Jessica.” Anya said.

“Hello Jessica.” The Man said and reached out his hand to shake hers. His hand dwarfed hers and she noticed how pleasantly warm his palm was as he gently shook her hand before releasing it.

“How do you do?” Jessica heard herself ask.

“I’m doing great.” The Man replied with a slight chuckle. “Better now that I ran into you two.”

“Yeah I literally ran into him.” Anya said, giggling. “Almost knocked me off my feet.” She seemed to have recovered slightly.

“Right. I’m still sorry about that.” The Man said.

“Oh don’t be. I was just clumsy.” Anya responded. The Man smiled brightly at her and Jessica felt a warm fuzzy feeling stir inside of her while she appreciated how the Man’s dimples appeared when he smiled.

“Anya told me you’re here on a trip with some friends?” The Man said to Jessica.

“Yes. It’s our friend Kim’s bachelorette.” Jessica quickly replied. She wasn’t sure why she was providing this information to a stranger but she couldn’t deny that she felt good and safe in that moment speaking with the Man.

“Really? And could Kim possibly be this lovely woman in silver who is coming over to join us?” The Man asked.

Anya and Jessica turned their heads to see Kim rushing through the crowded casino over to them, Hanna in tow.

“There you are!” Kim exclaimed when she reached the group. “No movement on the line. I thought we were meeting at the…” She suddenly stopped as she locked eyes with the Man. For just a moment there was a pause. Jessica watched as the expression on Kim’s face morphed from scrutinizing to serene in the span of a second. “Who is this?” She asked, her eyes not leaving the Man’s.

The Man smiled again. “Just a new friend.” He replied. “You must be Kim.” He said as he reached out and shook her hand just as he had with Jessica a moment before. A noticeable tremor ran through Kim as she shook the Man’s hand.

The Man finally turned to Hanna. “And what’s your name?”

Hanna had never cared much for strange men and Jessica half expected her to tell the Man to fuck off. But instead, after locking eyes with the Man for a moment, a beautiful smile split across her pretty face and she reached out to accept the Man’s handshake.

“I’m Hanna.” She said cheerily.

“Nice to meet you Hanna.” The Man said in his deep, even voice. Jessica saw Hanna quickly bite her bottom lip when the Man said her name. But then the Man began speaking again and she couldn’t remove her attention from him.

“Congratulations Kim. I hear we are celebrating your upcoming nuptials.” The Man said.

“Why thank you!” Said Kim sweetly. “It’s just nice to have all my friends here with me.”

“I’m sure it is.” The Man said and for a moment he glanced at each woman in turn. For the split second his gaze was on her, Jessica felt as if something was pushing on her subconscious. It wasn’t unpleasant. In fact the warm and fuzzy feeling was back and stronger than before.

“I’m interested in your choice of venue, though.” The Man continued as he gestured at the casino around them. “Wouldn’t a bunch of beauties like you be more comfortable on a beach somewhere?”

Anya tittered at that. “I’m sure a beach would be nice but we love places like this. We spent a lot of time gambling in college.”

The Man raised his eyebrows. “Really? So I’ve fallen in with a bunch of sharks huh?”

Now Hanna laughed. “Hardly, but we’ve played our fair share.” Her eyes glinted mischievously.

“Oh so you know your way around a table?” The Man followed.

“Of course.” Hanna replied.

“Hold’ em?” The Man asked.

“My favorite!” Now it was Kim who had spoken up.

“Excellent!” The Man exclaimed heartily. “I actually have a private table upstairs if you four would be interested. Of course, I entirely understand if you’d rather spend your evening elsewhere.” The Man’s eyes landed on Kim as he made his proposal.

Kim hesitated, but not for long. “I think that sounds like fun. Plus the night is still young, we can gamble a little longer before clubbing.” She said, glancing around at her friends.

Anya couldn’t agree fast enough. “Oh yes. I think that sounds like a lot of fun.” She said as she took one step closer to the Man, the angle putting her cleavage on full display as he smiled down at her.

“I’ve got some more gambling in me.” Hanna said confidently.

Jessica could tell that Hanna thought the group had reeled in a whale and she was going to try and pull a big score off of him. Jessica wasn’t so sure. Each of her friends looked at her expectantly. However, it wasn’t until the Man’s eyes were upon her that she knew what her answer was.

“I’m in.”

The Man led their little party over to the elevators and they rode up to the fourth floor of the casino. Then the Man led them down a brightly lit hallway to an inconspicuous looking door. Reaching into his pocket the Man produced some kind of key card which he pressed to a sensor next to the door. The lock opened with a hiss and the Man ushered them inside.

The room was impressive. Softly lit with walls that appeared to be made of real oak, the room was cozy and Jessica felt more confident in their decision to accept the Man’s offer. There was no furniture save an expensive looking poker table, which took up most of the center of the room, and five comfortable looking chairs forming a semi circle around it. A young man wearing the customary red vest of a card dealer was already standing at the table.

“Good evening Charles.” The Man said as he sauntered up to the table and took the chair furthest to the left.

“Good evening Sir.” Charles replied demurely.

Jessica thought his expression seemed rather strange, as she and her friends moved to take their seats. Almost like he didn’t really know where he was. But, as soon as the group was seated he swiftly reached into a hidden compartment on his side of the table and produced a heap of brightly colored chips, which he began doling out to each of them.

Once each of them had an equally sizable stack in front of them, Charles spoke softly again, “Small blind is two-fifty, big blind is five hundred.”

“Jesus!” Jessica thought to herself as she glanced at her tokens. “This is fifty-thousand dollars worth of chips!” She glanced around the table to see if any of her friends shared her alarm but none met her gaze. Kim had taken the seat closest to the Man and seemed perfectly content just sitting there smiling prettily. Hanna was in between Kim and Jessica, and her eyes darted back and forth between Charles and the Man. Anya had chosen the seat furthest to the right, directly across from the Man, whom she was staring at dreamily and leaning forward to allow easy viewing of her plunging neckline. Jessica caught a quick glimmer of the sparkly star stickers covering her nipples.

“Shall we begin?” The Man asked.

“Oh yes please.” Anya replied breathily, and the other three women nodded. Charles dealt two cards to each player and the game was on.

Jessica’s apprehension at the stakes was immediately eased as soon as she had cards in her hand. Here, she and her friends were in their comfort zone. Not only were they each a skilled card player in their own right, over years of playing together they had grown to innately understand each other’s tells and strategies. It made them a nightmare to play against in a group. “He won’t know what hit him.” Jessica thought.

Jessica checked her cards. Jack of spades and four of diamonds. Garbage. Anya started with a small raise. A simple feel out play. Jessica immediately folded.

As she slid her cards away a peculiar sensation struck her. It felt like a pair of soft lips were lightly kissing her neck. Jessica took a sharp intake of breath through her nose. The feeling was so real. She could even imagine a warm wet tongue lightly tracing a small circle on her sensitive skin. The sensation faded after only a moment, leaving Jessica with only a slight warmth in her belly.

Hanna and Kim both quickly folded as well. The Man called Anya’s raise and raised again, but only slightly. The attention shifted back to Anya. The Man was watching her thoughtfully. Anya hesitated for a few seconds.

“I fold.” She said and then let out a small gasp. Jessica watched as the beautiful Indian woman squirmed uncomfortably in her seat for a few seconds after giving up her cards. The Man had won the first hand before they even got to the flop.

“You ladies are very kind to go easy on me.” Said the Man in an amused tone.

The next hand was dealt. Jessica had a five and six of diamonds. Not bad. After a short flurry of early bets Kim and Anya both folded. The flop revealed the queen of hearts, the ace of clubs and the four of diamonds. The Man raised by a small amount, Jessica called and Hanna folded. The next card revealed the eight of diamonds. The Man bid aggressively and stared at Jessica.

Jessica pondered for a moment. Calling was an easy decision. She had good odds at a flush and a straight flush was still in play. She looked at the Man, trying to find a tell. Instead she found herself trapped in his eyes. They pierced right through her, making her feel naked and vulnerable. Jessica could feel a pushing sensation on her subconscious. She gulped and folded.

As soon as she did, the powerful sensation returned. This time it felt as if a powerful pair of hands were mauling her heavy tits. Jessica could feel strong fingers knead the tender flesh and felt each of her fat nipples pinched between a firm thumb and forefinger. She let out a soft, weak, feminine squeal. The sensation faded after a few seconds but Jessica could feel her hard nipples straining against the lacy fabric of her lingerie and the heat inside her belly had moved to her pussy.

The Man smiled across the table at her. He had won again.

The next dozen hands were a blur. Some lasted longer than others but each ended the same, with the women all folding and more chips being placed in front of the Man. Each time she gave in a new sensation overwhelmed Jessica. Once she felt the hands again, this time squeezing her plump ass. Another time she felt a thumb run across the lips of her now soaking pussy. And yet another time she felt as if someone was blowing a tiny gust of air directly onto her clit. Soon she was an overstimulated mess, her pussy was positively leaking down her thighs and it was all she could do to pay attention to what cards she was dealt.

Kim and Anya seemed similarly affected. Kim was blushing furiously and Jessica could make out the imprints of her hard nipples beneath her silver dress. Every time she folded it was accompanied by her biting her bottom lip and looking at the Man pleadingly. Anya was doing the worst job of hiding her arousal. She was openly moaning each time she lost a hand and scooting her cute little ass back and forth on the seat of her chair. Her left hand had crept between her legs and was gripping tightly onto her inner thigh. Her eyes never left the Man and there was a helpless look in them.

Updated: October 13, 2020 — 5:56 pm

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