Winner Takes All: Round 03

Colleen screamed. A distant part of Frank's mind worried that a passing pedestrian might hear it and investigate or call the cops, but he was too far gone to care. Colleen's entire body twisted as she orgasmed, and only Charlotte's weight on top of her kept her from falling off the bench.

Frank exploded. His nuts squeezed themselves almost painfully into the base of his shaft, and he unloaded into Colleen's bowels. His semen almost didn't make it past the tight ring clamped around his rod, but it managed to slip through between Colleen's spasms.

When his load was finally spent, he stumbled back, his shaft sliding out of Colleen's somehow still snug grip, even as she lay limp on the bench underneath Charlotte. He saw a few drops of semen dribble out of her asshole before it winked closed.

Frank's head spun. He sank to his knees, then his ass, then flat onto his back, before passing out.

When Frank came to, it was to the now familiar sensation of a warm mouth enveloping his cock.

He cracked his eyes open and found Charlotte, still naked, on her knees between his legs with her ass in the air, her tits hugging his leg and his half-limp cock in her mouth. When she noticed his gaze, she somehow smiled devilishly with her eyes despite the obstruction between her lips, then went back to work. She finished cleaning him with a few more swirls of the tongue and strokes of her lips, then let his dick pop free from her mouth.

"You okay, sir?" she asked, still grinning.

"Yeah," Frank breathed. "I just... needed a minute... is all."

Frank took a moment to collect himself. He took another moment, since it seemed like a shame to interrupt Charlotte, who was still sucking his dick with long, slow, relaxing strokes. When she eventually paused for a breather, he slowly sat up. Colleen stirred from her position still tits up on the bench. Her eyes opened, and she groaned softly.

"Right. Let's hit the showers." Frank declared.

The studio had a separate tiled room with a toilet and shower tucked into one corner. Frank ushered the girls in with a firm pat on each rear, fetched his phone and shot a quick text to McCurdy instructing him to come in and clean up the mess, then joined them under the hot water.

As they lathered and rinsed him, paying the usual special attention to his cock and balls, along with some extra massaging of the back and shoulders, Frank resolved to do everything in his power to make sure he never had to shower alone again.

***

The rest of the day passed much less eventfully. The trio finished showering, ate the sandwiches that McCurdy had so graciously delivered, and made preparations for the last round that evening. For the girls, that meant more fancy clothes and fresh hairdos, courtesy of McCurdy's seemingly limitless credit card. Frank rewarded him with a quick en route blowjob from Colleen, crouched naked in the passenger seat with her ass in the air and her head bobbing in McCurdy's lap.

Frank himself was feeling pretty spent, and hadn't intended to enjoy his winnings any more that afternoon. The sloppy sucking sounds and muffled grunts emanating from the front seat, however, apparently inspired Charlotte. With a mischievous grin, she slid to her knees in the backseat, slipping her fresh jeans and panties down over her ample ass and hiking up her new bra and t-shirt to free her breasts. She deftly unbuckled Frank's belt and started tugging at his trousers, and Frank, feeling gentlemanly, didn't stop her. He allowed Charlotte to slowly, leisurely suck him off as they drifted through traffic.

He let himself relax, emptying his mind, letting the soothing sensations wash over him. With long strokes, minimal teasing, and a little hands-on attention for Frank's nuts, Charlotte steadily worked him up to his peak and tipped him over the edge, her mouth wrapped around Frank's cock the entire time.

As he shot his load directly into the warm embrace of Charlotte's throat, listening to her giggle in satisfaction, Frank had only one thought: I have to win tonight.

McCurdy managed to get the town car to their destination without crashing, road head notwithstanding. While the girls were shopping and styling, Frank researched. So far, the tournament had revolved around pretty classic battles of wit, and it seemed prudent to assume that trend would continue. Besides, if they picked something completely random, the odds that Frank would happen upon it by random chance this afternoon were slim, and his opponent would probably be likewise unprepared. He focused instead on the usual suspects, reviewing the basics across the board and refamiliarizing himself with some more advanced concepts from games with which he was more familiar.

Maybe I should have spent more time studying, he thought, and he couldn't escape the traces of guilt and anxiety that accompanied that idea. But it would have been a shame to waste the time I'd already won with the girls, and it's not like I'd have any guarantees, no matter how much I practiced.

No use worrying about it now, man. You've made your choices. Soon, you'll get to live with them.

The mental self-coaching didn't eliminate Frank's doubts, but he made an uneasy peace with them, accepted them, and relegated them to a distant corner of his mind.

At least the girls would hopefully give him an advantage again. Charlotte's charms had been invaluable against McCurdy. He'd probably face Clark Brenner, the middle-aged gentleman he'd met last night, although in all the excitement the previous evening, he'd never discovered whether Brenner or his brunette opponent won the round. Brenner had struck Frank as more composed than McCurdy, and correspondingly more mentally formidable, but he'd also seemed quite taken with Charlotte, so Frank might still have an edge.

The girls eventually emerged from their errands, and Frank was not disappointed. He'd left Charlotte in charge, and she'd selected an upscale, if classic, black number for Colleen that emphasized both her slim, athletic frame and her more modest curves. The minimalist black heels that completed the ensemble further accentuated the muscular calves leading to her firm, pert butt. Against the background of her dark dress, Colleen's brilliant golden locks, now polished, straightened, and styled to perfection, stood out even more vibrantly, and a set of sparkling diamond earrings and necklace pendant completed the ensemble.

Charlotte, somehow, still outshone her. Her fiery red mane shone just as brilliantly, falling in waves past her ears and resting in perfect, seemingly natural curls on her shoulders, bouncing slightly as she walked. Amethyst earrings complemented the purple evening gown she'd chosen for herself, similar in some ways to the one she'd worn that first night, but a much brighter, bolder shade. It was somehow less revealing but more suggestive, showing less skin than her previous evening ensembles, but sewn and cut with accents and contours that flaunted exactly what treasures were so well hidden under the fabric.

Both dresses were tight enough in the right places without any bumps or lines that, other than whatever support was sewn into the garments themselves, Frank was confident that the girls weren't wearing anything except their dresses.

Perfect.

As the afternoon grew late, McCurdy chauffeured them back to the manor. Frank immediately retired to the bedroom for a power nap, with instructions for McCurdy to behave himself and have something suitable delivered for dinner, and for the girls to wake him in two hours.

One hour and fifty-five minutes later, Frank awoke once again to the feeling of a warm mouth wrapped around his cock.

It was Charlotte's. She crouched on her knees on the right side of the bed, still looking immaculate, her head in his lap, face impaled on his dick. Colleen crouched on the other side, her appearance also unblemished, carefully holding Charlotte's hair out of harm's way while she worked. Colleen noticed Frank's now open eyes on them, and she flashed him a shy smile.

Colleen waited patiently while Charlotte savored the flavor of Frank's shaft. Then she nudged Charlotte aside and murmured, "My turn."

They swapped. Charlotte protected Colleen's hair while the blond bobbed in Frank's lap, her smaller mouth clutching Frank's cock tightly but soothingly. As she worked, she emitted delightful little moans, as if she was sampling some kind of scrumptious appetizer.

Frank was glad to hear her enjoying herself. Blowjobs were always better when the girl sucking your dick took pleasure in the process.

The girls traded every minute or two, helping each other stay clean in the process. Frank carefully hooked a finger under the hem of each dress and pulled each one over its respective ass, at which point he belatedly realized why he hadn't noticed any panty lines earlier.

Even though Frank had already put his penis through some considerable paces today, the sight of both girls with their asses in the air and the mixed stimulation of the double blowjob soon sent him over the edge again. He cried a warning as he reached the point of no return, and Charlotte hurriedly forced Colleen out of the way to wrap her lips around Frank's head, twirling her tongue around the tip.

Frank erupted, again, as Charlotte sucked and swirled. As Frank came down, she slowed, then stopped, then carefully removed her lips from his softening member. She didn't spill a drop. She sat back, tilted her head back, and visibly swallowed.

"Mmm," she cooed, and smiled at him. "Yummy."

They cleaned up the minimal mess with a towel from the bathroom, then marched downstairs. As instructed, McCurdy had dinner waiting, apparently catered and delivered from the family owned Italian joint a few streets over.

They ate in the dining room, making a little small talk but mostly focused on their meals, except McCurdy, who was exiled to the kitchen with his food when he couldn't stop staring at the women.

Frank showered and dressed, donning a new dress shirt from their earlier shopping expedition to go with his only tailored suit, which had at least been freshly dry-cleaned with same day delivery at McCurdy's expense.

Finally, it was time to play.

***

Frank knocked on the door in the same pattern as the previous two nights: two quick, then two slow. Same rhythm as the rules: Winner Takes All.

He heard the thud of the deadbolt, and the heavy wooden door swung open. Frank strode inside, a gorgeous woman hanging on each arm, McCurdy following meekly behind.

The doorman led Frank and his posse along the now familiar path to the back room, inside which a moderate crowd of people already mingled.

Frank and his escorts quickly attracted a crowd, lovely ladies in exquisite evening gowns and refined gentlemen in pristinely tailored suits gathering to shake Frank's hand, congratulate him on his successes thus far, and of course, to ogle his prizes. Air of elitism or not, most of the men, and many of the women, were practically drooling over Charlotte and Colleen.

Charlotte played her part, engaging in polite conversation, laughing or giggling when appropriate, and graciously accepting the many compliments she received, but she stayed on Frank's arm and always diverted the attention back to him.

Colleen started out much shyer, but she picked up on Charlotte's mannerisms and mimicked them in her own way. Her smile was more cursory and polite than Charlotte's flattered grins, and she clung even more closely to Frank, even wrapping her arms around his shoulders and pressing herself to his side, as though trusting him to protect her from the hungry masses.

Frank obliged his admirers, trading handshakes and exchanging compliments, but he kept his eyes peeled for his final opponent, presumably Brenner. Ideally, he could use this opportunity to get a better sense for the competition, maybe even throw Brenner off his game, assuming he was susceptible to the girls' charms.

Brenner didn't make an immediate appearance, but it wasn't hard to figure out why. While several of the guests mingled in twos and threes around the room, exactly one other large cluster had formed at the other end. If Frank's crowd had attracted more men than women, the other group made up the difference.

Once he endured the first wave of greetings, Frank politely excused himself and placed a hand on either girl's hip. Then they made their way across the room to meet the competition.

The new crowd parted around the trio, and Frank quickly located Clark Brenner in the center.

Or, at least, he assumed this was Brenner. The height and frame seemed correct, but it was hard to recognize him in his new gimp outfit. Especially with another figure trapped in an identical leather getup beside him.

Startled as he was, Frank surveyed the scene. In the small clearing in the middle of the crowd stood two stiff figures in full gimp costumes. Behind them stood Claire, Brenner's dirty blonde prize from the first round, who Frank and Charlotte had met the previous evening. She'd traded her business attire, ball gag, and handcuffs for a dominatrix outfit, complete with the riding crop she was tapping in one palm. As Frank made eye contact, she flashed him a devious smile. The riding crop flashed out twice in quick succession, a lash across the ass of each man in front of her, eliciting quiet muffled cries from the recipients. Frank grimaced.

"Ah," a sharp feminine voice cut in. "You must be my opponent and future prizes. Do you like what I've done with my winnings so far?"

Frank turned his attention to the speaker, a brunette in maybe her mid thirties. At first glance, Frank would guess she was come kind of high-powered doctor, though she wore a brilliant white blouse and jet black blazer and pencil skirt, rather than a lab coat, and she bore a necklace with a single dark black gemstone pendant, rather than a stethoscope, in addition to the identical gemstone on her one ring and the brilliant silver Rolex on her wrist. The Pendant hovered just where her cleavage began. Despite the fashionable but conservative attire, she was clearly well-endowed, her breasts too large for the blouse to conceal, though it was still quite modest.

Her brown hair was done up in a tight bun, not a strand out of place. Simple, reddish-brown horn-rimmed glasses perched high on her nose in front of piercing blue eyes. The crisp, tall, no-nonsense black heels on her feet completed the ensemble. She sat in one of the thick wooden armchairs from the gaming tables, a nearly-untouched glass of wine swirling in one hand, and her gaze drilled into Frank, cold and calculating as she sized him up while awaiting his response.

Frank took a breath. It would have been better, he noted, to have a quick response ready to fly, but he didn't, and giving the wrong answer, or letting his voice crack, would not serve him well.

"Not my style," he managed, pleased that he at least sounded calm and collected, "but to each their own, I suppose."

"You'll join them soon," she responded.

"No thanks." Frank answered, falling into the flow of the banter. "Those facemasks make it hard to give orders, and besides, black leather clashes horribly with my complexion."

"Shame. You do seem to have an appropriate sense of style," she responded, finally taking her eyes off him to examine Charlotte and Colleen appreciatively. Then she locked gazes with him again. "But my wardrobe will suit you better."

"Disagree. I'm Frank Jones," he said, holding out his hand. It was close, but not quite within reach from her perch.

"Allison. Dr. Allison Monroe," she answered, extending one hand, wrist dangling in ladylike fashion. She made no effort to reach for Frank's hand, or to move at all.

Rather than leave his hand hanging in limbo, Frank took the half step forward and bent slightly, closing the gap and taking her hand in his. He gave a polite squeeze, then stepped back.

"Doctor?" he asked.

"Psychiatrist."

Figures, Frank thought.

"How does a lady like you end up entering a tournament like this?" he probed.

"Oh, I'm sure you can infer. The human mind is an endless puzzle, and while I of course enjoy my work, professionalism dictates that I never get to play this sort of game with my patients. I thought it would be fun. I was right."

"And when you lose?" Frank prompted.

Monroe said nothing. She just smiled, eyes still locked on Frank's.

Silence stretched between them, and Frank didn't break it. A hush even fell over the crowd around them, as the onlookers observed the exchange.

"Ladies and Gentlemen," the announcer cried, "I believe it's time for our final round to begin. Please, take your seats. Sir, Ma'am, if you'd be so kind as to relocate to the table at my side, we can determine, once and for all, the winner of tonight's contest."

Frank kept his gaze locked with Allison's for a moment longer, then broke eye contact, looking instead to the announcer and table. He wore the same tuxedo as always, or at least an identical copy, and stood next to a waist-high semicircle topped with green felt, accented by two simple but stylish chairs arranged around the curved edge.

Frank made his way to the table and took the seat on his right. He had a hunch about where this was going, and preferred to use his left hand for peeking at playing cards.

Monroe watched. Then, as if she had all the time in the world, she held out her mostly full glass of wine for one of the staff to take away and rose from her seat. Her sharp outfit, while stylish, didn't reveal much. She had a healthy figure, at least from what Frank could see, lean but not too skinny, with accented curves in all the right places. Some high-end tailor probably helped with that. She strode nonchalantly across the floor, heels clacking, with the confident air of someone who maintains a flawless physical appearance for the aura of power it projects, and joined Frank at the other end of the bend.

The crowd took their seats, and the past participants, now the game's stakes, retreated to the edge of the gaming area, each posse positioned behind their current owner. The host took his place standing in the middle of the table's straight side and produced two small shrink-wrapped cardboard boxes, one cover red and the other blue. Another staff member appeared next to him, carrying two matching sets of small, colorful ceramic disks.

"The game," he declared, "is Poker. Texas Hold'em Style. A fitting end to a week of impossibly high stakes.

"My associate and I will handle the cards, of course," he continued, "although for a betting position, the lady will be considered the first dealer. Each player starts with $100,000 in chips. The blinds will start at 500 and 1000, and will increase every half hour until one player claims victory.

"Let's begin."

He and his helper cracked the packs open, shuffled up, and dealt the cards. The host switched decks every hand, dealing from the fresh stack while his assistant shuffled the previous cards.

As expected, the doctor was no newcomer to Poker. She knew what cues to use for communication, and she never once stumbled on her game actions or moved out of turn. Also as expected, unfortunately, she seemed to understand more than just basic strategy, and Frank quickly found himself frustrated as he tried to analyze her play patterns and develop a counter strategy.

Frank was no stranger to the game. It wasn't hard to pick up some solid experience playing in dorm lounges and frat houses around campus, and with his personal interest in games and psychology, Frank had studied Hold'em until he was confident sitting down at any table of classmates. Even when he occasionally ran into a better player, he could tighten up, minimize losses against the shark, and punish the rest of the fish at the table enough to turn a profit most nights. He'd also figured that some form of Poker was a prime candidate for this tournament, and had spent several hours over the last few days and weeks brushing up.