The Man's Challenge

Hanna was the only one who still seemed in control of herself. Like Kim, a blush had crept to her cheeks, but her mouth was set in a hard line and Jessica hadn't heard her make a sound throughout the game. She had even managed to keep the majority of her chips despite being unable to win a hand.

Jessica suddenly noticed that the current hand looked like it would finally be played to completion. She, along with Anya and Kim, had folded before the flop. But Hanna and the Man had been raising back and forth aggressively. The ten of diamonds, queen of spades, and king of clubs were all face up. Hanna appeared to be straining to stare at the cards in front of her, or perhaps straining not to return the gaze of the Man, who was looking at her intently. The fourth card was flipped, queen of clubs.

Hanna smiled and made her move. "All in."

The Man didn't flinch. "Call."

An avalanche of chips were pushed into the pot by the two combatants. Hanna took a deep breath and flipped over her cards. Pocket queens, hearts and diamonds. Four of a kind. The Man smiled and flipped over his cards. Pocket kings, diamonds and spades. Three of a kind. All that was left was the river.

Charles dealt the last card and flipped it over with a flick of his wrist. King of hearts.

Jessica watched as the realization that she had lost washed over Hanna. The beautiful Asian woman's mouth popped open and her hands gripped the table in front of her tightly. A powerful tremor wracked through her lithe body and she shook violently. The muscles of her shoulders strained and her abdominals clenched. Then it was over and she nearly collapsed. Hanna looked up and met the Man's gaze. There was a wild look in her eyes.

"Oh fuck. I was so close." She whispered.

The Man chuckled and turned to Charles. If the dealer was concerned by the women's behavior it didn't show. Throughout the entire game he had remained blissfully calm and unassuming.

"Some privacy please." The Man said.

"Of course Sir." Charles replied and he left the room through the same door the party had come in, no more than forty minutes ago.

The Man looked at the women. "So. I feel it's fair to say that the game is over. That being the case, it appears you ladies owe me a considerable sum of money."

None of the women responded. Kim was watching Hanna, who was still trying to catch her breath. Anya was openly panting now, her tongue lolling out of her mouth. Jessica just stared dumbly and squeezed her thighs together, trying not to think about how much her pussy was aching to be filled.

"How's this for a proposition?" The Man continued. "We'll go double or nothing. I'll fuck each one of you in turn. If I cum before making each of you orgasm at least once, then I'll forgive your debt and you can go. But if I make each one of you cum before I do, then you all agree to spend the rest of the night with me, and I'll forgive your debt anyways."

This time, the women all responded immediately and in unison.

"Yes Sir."

Jessica felt the pushing on her mind again and quickly moved into position with her friends. They lined up in a row and bent over the poker table. Each pulled their dress up over their ass. Kim slid her tiny white thong off her shapely rear and let it fall to the ground. The little scrap of a garment was already translucent with her juices. Hanna's black thong and Jessica's red g-string, both stained with girl-cum, quickly joined it on the floor. Jessica wasn't surprised to learn that her suspicions regarding Anya's lack of underwear were correct, but was a bit surprised to see that her curvy little Indian friend kept her pussy perfectly shaved.

The Man walked around the table and appraised the sight before him. Four gorgeous asses all lined up in a row, just for him. And four tight wet pussies, each on display, waiting to be fucked. The Man hadn't even touched them and yet the smell of their sex already permeated throughout the room.

The Man slid off his suit jacket before undoing his belt, which fell to the ground with a loud clunk. The women each peered over their shoulders as the Man shed his pants and underwear. Anya moaned softly in Jessica's ear as the Man's cock came into view. It was thick and strong and dangerously hard. Jessica felt her pussy quiver as she laid her eyes on it. The Man's cock swung between his legs as he moved behind Kim.

Once the Man had planted himself behind Kim, he abruptly grabbed a fistful of her long shiny black hair and pressed her cheek against the poker table, making sure her face was pointed in her friend's direction. Then he lined up his shaft with Kim's sopping pussy. Kim whimpered as the head of the Man's cock kissed the entrance to her cunt.

Then the Man began to push. The rest of Kim's bachelorette party watched her face contort as the Man began to fuck her. She shut her eyes tight and her mouth popped open in a silent scream. When Kim's dark eyes opened, Jessica saw nothing but lust and submission behind them. It wasn't until the Man buried his entire member inside of her pussy that the words started tumbling out.

"Oh my god! He's so fucking big! This is the biggest cock I've ever taken!" Kim squealed. The Man started fucking her slowly, pulling back only a few inches before driving his length back into her depths. Kim's moans became more frantic. "He's so fucking deep! He's hitting my deepest spots! Oh fuck! It's so fucking good!"

The Man picked up the pace, his hips slapping against Kim's ass. The slender Asian woman trembled and shook against the powerful thrusts. Jessica thought for a moment that her friend was trying to fuck the Man back, but soon realized that there was no way Kim still possessed the level of control necessary to do so. Her body was merely reacting to the dominant screwing she was receiving.

"I'm gonna cum! I'm gonna cum! I'm so sorry but I'm gonna cum!" Kim screamed.

"It's okay baby girl." Anya replied. "Go ahead and cum all over."

Her friend's permission had scarcely left her lips before Kim's orgasm overtook her like a freight train. She writhed helplessly against the hard table. A jet of her pussy juice escaped and splattered to the floor. After thirty seconds of convulsions, she collapsed onto the table.

The Man slid his still hard cock out of the young woman slowly and took a step back. "That's one." He whispered gruffly. He wasn't even breathing heavy.

The Man took a step to the right and was behind Hanna now. Jessica heard her take a sharp breath of anticipation. Jessica could see that the Man's cock was still shiny and slick with Kim's juices; but she could also see that the extra lubrication wasn't necessary. Hanna's pussy was absolutely drooling with need. Jessica watched as trickles of liquid cascaded down the athletic woman's thighs as the Man rubbed the head of his cock against her sex.

Suddenly the Man drove his entire cock inside of Hanna all at once, slamming the entirety of his cock into her cunt with one smooth motion. Hanna straightened involuntarily and let out a grunt as if she'd been punched in the gut. The Man took advantage of this moment to grab her ponytail tightly and hold her head in place as he began to fuck her hard with quick violent thrusts.

"Oh oh oh oh oh!" Hanna managed to gasp out. "Fuck! He's tearing my pussy apart! He's splitting me open! He's ruining my pussy!" Her eyes were rolling into the back of her head.

The Man's onslaught continued. He hammered away at Hanna's tight little hole, his hips making an impressive "thwap" sound each time they connected with her muscular ass. Hanna's hands flailed desperately for a few seconds before Kim and Jessica reached out and each grabbed one, providing the poor women with something to grip as she was pounded mercilessly.

This continued for a few minutes with Hanna just barely holding on against the Man's assault. Jessica knew that Hanna couldn't stave off her impending orgasm for long but was nevertheless impressed by her friend's determination. Hanna gritted her teeth between moans and was clearly using all of her willpower to fight the rising urge to cum. But then something happened that shattered her resolve.

Jessica watched in disbelief as Kim suddenly leaned over, cupped Hanna's face in her hand, and began passionately kissing her. Hanna immediately melted against her friend's soft lips and kissed her back. The two sexy Asian woman's lips smacked together sloppily and their tongues wrestled one another. The Man continued pumping into Hanna's pussy and before long a powerful quake ran through her lithe body. She came hard on the Man's cock, moaning and gasping into her friend's mouth as her pussy convulsed again and again.

Kim was still planting small kisses on her defeated friends lips and forehead when the Man pulled free from her wet channel. "That's two." He said in a satisfied tone.

Then he turned his attention to Jessica and somehow her burning need to be taken grew even stronger. She wiggled her big ass back and forth enticingly. The Man stepped behind her and took a moment to grab and spread her ass cheeks with his strong hands. Her tiny pink flower opened up for him in a clear invitation to be used.

The Man accepted and steadily pushed his throbbing cock into her. Jessica squealed loudly and squirmed around the invading shaft. She had many lovers in the past but had never felt anything like the overwhelming masculine power that the Man's cock seemed to radiate. Her pussy was so wet it felt like it was melting. The Man's cock reached to her innermost parts, stirring up places where nothing, not even a sex toy, had ever reached.

"Thank you Sir! Thank you for fucking me!" Jessica babbled. "Thank you for owning me with your thick cock!"

"You're welcome." The Man responded. There was no condescension in his tone.

The Man began fucking Jessica's pussy in earnest. Pleasure was overwhelming Jessica's senses. Every thrust caused her pussy to spasm helplessly around the Man's thickness. Jessica could feel the most powerful orgasm of her life building deep within her core. She knew that when it came it would break her.

The Man's strong strokes continued and soon Jessica reached the mountaintop. The Man slammed once more into her pussy and this time stayed there, leaving his entire cock inside of Jessica, filling her pussy to the limit. Her vision went white and her pussy clamped down on the invading shaft. Jessica gasped and shook as the powerful orgasm rocked her. The Man held her in place through it all, making sure she couldn't wiggle away from his cock and forcing her to feel the full brunt of the orgasm he had driven her to.

After nearly a minute of pure ecstasy, the Man released Jessica and she collapsed onto the table. A tiny moan escaped her lips when the Man finally pulled his cock from her gaping pussy. Jessica's teeth were chattering and she fought the urge to pass out. She felt strangely empty now that the Man was no longer filling her needy pussy, but she couldn't even remember feeling so completely satisfied.

"That's three." Jessica heard the Man say over her collapsed body. "Just one more."

Jessica managed to turn her head to watch the Man step behind Anya and line his cock up with her gushing pussy. Apparently watching her three best friends effortlessly dominated by the Man had been too much for the poor little slut. She came helplessly and loudly before the Man's cock was even halfway inside her, her juices added to the growing puddle on the floor.

The Man laughed at the display. "I guess that's four. Looks like I won." He said as he continued to push his rock hard cock into the still cumming Indian woman.

"Yes! Oh fuck yes! You win! You win Sir! Please let us be good little whores for you!" Anya shrieked.

"If you insist." The Man said with a grunt and then began fucking Anya with hard short strokes. In less than a minute the tiny woman was cumming again. She flailed so hard that her tits fell out of her low cut green dress and the sparkly stars covering her nipples bounced wildly as she convulsed.

When Anya finally calmed down after her second orgasm the Man pulled out of her with a wet "plop'' sound and took a step back. After a moment he proceeded to pull his pants and underwear back up although the outline of his impressive bulge was still clearly visible.

"Alright ladies pull yourself together." The Man said as the four women gathered around him. Kim, Hanna and Jessica all left their ruined panties on the ground. Anya nearly forgot to put her boobs away until the Man gave her a gentle smile and she sheepishly readjusted her dress. Then the Man said, "Let's take this to my apartment. Okay?"

For the second time that night the bachelorette party answered in unison. "Yes Sir."

Jessica felt as if she was walking through a haze as the Man led the group out of the poker room and then out of the casino onto the busy street corner. Her thoughts didn't become clear again until a stretch limousine pulled up in front of the party. The Man opened the door invitingly and each girl climbed into the spacious backseat. The Man followed them into the backseat and the limo took off into the night.

As soon as he sat down the Man immediately pulled Jessica in for a deep passionate kiss. Her mind went blank as the Man frenched her. She was only aware of the softness of the Man's lips and the renewed need growing between her legs. After a few minutes the Man drew away and let out a deep groan, allowing Jessica to take in the erotic scene that was unfolding around her.

Anya had been the one to draw out the groan from the Man. While he had been kissing Jessica she had moved in between his legs and managed to free his cock from his pants again. Now she was bobbing her mouth up and down on the head of his cock. Jessica and the Man both looked down at the gorgeous woman as she blew him, but her big brown eyes were trained on the Man's steely blue ones. Jessica was both aroused and a little scared by the depths of devotion and lust she saw in Anya's eyes.

Jessica peeked over at Kim and Hanna who were entangled in their own embrace. The two were making out again, except now Hanna was clearly the aggressor. Jessica watched as Hanna bit down hard on Kim's soft bottom lip. At the same time, Hanna slipped her hand inside of the deep neckline of the bride-to-be's silver dress, and quickly found her braless, perky tit. Kim moaned deeply as her friend rolled her nipple back and forth between her fingertips, bringing it to a hard point. Jessica watched as Hanna broke their kiss for a moment, and instead nuzzled her nose against Kim's affectionately.

Jessica thought back to their time in college. Anya had told her multiple times that she suspected Kim and Hanna had experimented with one another, but she had never provided any evidence to back up her claim. At the time, Jessica had simply dismissed the idea as one of Anya's horny fantasies. But now...watching how passionate they were, Jessica was starting to think she might have been on to something.

Her train of thought was ruined when she felt the Man's strong and warm hand reach down the grip the inside of her thigh. It was as if liquid heat poured from his fingers up to her cunt. Her pussy was soaked again and aching to be touched. Jessica bit her bottom lip and spread her legs, hoping the Man would move his hand a few inches north and grant her sweet release.

Anya was still busy using her mouth to pleasure the Man. She was now alternating between the Man's nuts, sucking each testicle into her greedy mouth, one after the other. The Man's imposing shaft rested on her face, covering almost half of it. But Jessica could see that the one eye that was not covered by cock flesh was still staring up adoringly at the Man.

Anya released the Man's testicles from her mouth and licked the shaft from base to tip once, twice, three times. On the third time, when she reached the tip, she enveloped the Man's cock between her lips again, and then slid slowly down, taking an impressive amount of the Man's cock into her throat. She almost reached the base before coming back up to about the midpoint of the dick.

The Man let out a growl. "Amazing." He said. "Do you not have a gag reflex?" He asked.

Without removing his cock from her mouth, Anya managed to shake her head no.

"Well then little one." The Man continued. "Would you like me to skullfuck you?"

Still with her mouth full, Anya desperately shook her head yes.

The Man's other hand, the one not between Jessica's legs, reached up and easily palmed the back of Anya's head. He steadily and forcibly pushed her head down until she had taken the entirety of his length in her mouth. The Man let out a grunt as the last few centimeters of his cock disappeared. Then, taking a fistful of Anya's hair, the Man began to move Anya up off the base of his cock, only an inch, before plunging her back down. Jessica watched how Anya's cheeks and throat bulged as the Man facefucked her. Even Kim and Hanna cease their assault on one another and watched as the Man used their friend as a fuck toy.

"Wow. You are a good little slut, aren't you?" The Man said between gritted teeth.

Anya shuddered at the Man's words. It looked to Jessica as if the Man's praise alone had just caused her to have a miniature orgasm. With a gasp, the Man pulled Anya off of his cock. Anya came up choking and took several deep breaths as she tried to compose herself. Thick strands of saliva still hung between her lips and the Man's cock. As she looked at the Man's glistening pole, Jessica thought how amazing it was that he had still not cum yet.

Suddenly, the limo came to halt. "Looks like we're here." The Man said with a smile.

The Man led the party out of the limo in front of a posh looking apartment complex, then across a short path and into a unit located on the ground level. The apartment itself was spacious and modern but Jessica paid it little mind as the man ushered them into a room in the back.

The room was, to no one's surprise, the Man's bedroom, and was dominated by a massive California king style bed located in the center of the room. The women formed a small semicircle around the Man and he appraised each of them for a moment.

The Man leaned in and began kissing Anya. She eagerly kissed him back and yelped with delight when he reached down with one hand and grabbed her juicy ass. The Man pulled back for a moment and then moved to Hanna, kissing her now. Hanna responded in kind, kissing the Man back and swirling her tongue around his. The Man kissed a trail from Hanna's lips down her neck and she let out a girly squeal when he bit down on her collarbone. The Man withdrew again and pulled Kim in for a crushing kiss. As his mouth dominated Kim's, the Man stuck his leg out just a bit, allowing the sexy Asian woman to writhe pathetically against his thigh for a few moments. Finally the Man pulled away from Kim as well, leaving her panting and shaking slightly.

Finally, the Man turned to Jessica. She welcomed his kiss and enjoyed the contrast between his soft lips and the hardness between his legs. The Man reached behind her and unzipped her dress and then unclipped the bra holding back her heaving breasts. When the Man stepped back from her, the garments fell from her body, leaving her delicious curves on full display. Kim and Hanna helped the Man unbutton and then shed his shirt, revealing his muscular torso. Then Anya stepped in and took off the Man's belt and helped him to step out of his pants, then his underwear. Finally, the Man was fully nude in front of him. The oversexed bachelorette party quickly shed whatever clothes they had left on. After Anya peeled off the star stickers covering her chocolate brown nipples, the whole group was naked.

The Man pushed Jessica on to the bed. "You first." He said, softly.