Winner Takes All Round 01

Schluck. Schluck. Schluck. Schluck.

Ah

, Frank thought to himself, gazing down at the ravishing red curls cascading into his lap as the head beneath them bobbed up and down along his cock. The toned yet voluptuous woman attached shifted her weight from one knee to the other from her kneeling position between his legs on the floor in front of Frank's bed.

Nothing satisfies like the warm, wet mouth of a beautiful woman.

"Unngh," he groaned as the mane of red hair in his lap paused, lips pressing loosely around the base of his helmet, and massaged the underside with slow circles of her tongue.

Especially,

he amended to himself, savoring the sensation as she engulfed him again, his cock's head tracing the roof of her mouth towards her throat,

a mouth well and fairly won

.

As she continued to slurp, Frank leaned forward. He pressed her head deeper into his crotch with one hand while reaching around to pale white ass with the other. As his cock forced its way down her convulsing throat, Frank gave her glutes a hearty slap. Without letter her up, he inched his fingers in towards the crack of her ass until they brushed against her puckered anus.

"Mmph!" The redhead squealed in surprise, and Frank felt the back of her head push on his hand as she attempted to reel back. He held her for another two seconds, fingertip pressed against her asshole as she struggled to dislodge his cock from her throat, before finally letting her up.

"What the hell do you think you're going?" She sputtered, saliva dripping from her lower lip and chin.

"Hey now," Frank reprimanded. "No whining. I won you fair and square, did I not?"

***

Only three hours earlier, Frank raised his clenched fist and knocked the password: two knocks, one, and one again. The cadence, he knew, not only requested entry; it matched the syllables of tonight's only rule: Winner takes all.

Even over the dull roar of the main gambling room behind him, Frank heard the distinct thud of an abnormally heavy deadbolt turned aside, and the heavy, rustic wooden door swung open. The sound of conversational pleasantries and clinking glasses filtered out alongside the aroma of genuine leather, fine alcohol, and raw wealth. With a deep breath, Frank strode through the open doorway.

As the doorman lead Frank through the illicit gambling den, he noticed the tell-tale signs of an overprivileged, high-society clientele. For the ladies, sparkling jewels covered more skin than the thousand-dollar dresses they accentuated. The gentlemen substituted gemstones for crystalline glasses full of rich amber liquors and gowns for custom-tailored suits from across the ocean. Frank blinked his way through the cigar smoke hanging in the air and followed his guide toward another thick wooden door behind the bar. With a nod to the large males on either side of the archway, the valet pushed the door opened and beckoned Frank inside.

Frank found himself in a dark, modestly-lit chamber, large enough to house a small bar on the near wall, roughly three dozen-comfy looking chairs arranged along the remaining perimeter, and four central tables large enough to seat two people. Earlier arrivals already occupied most of the encircling thrones and five of eight central seats. The doorman showed Frank to his position in the center, across from one of the only two seats still unoccupied, and promptly exited back into the main parlor. Frank sighed and began to read the contract in front of him:

I, __________, hereafter referred to as "the Undersigned," being of sound mind and eligible legality, intentionally, and as part of my consideration for entry into this agreement, hereafter referred to as "the Contract," acknowledge and submit to the following stipulations, hereafter referred to as "the Rules" while participating in the "Winner Takes All" tournament, hereafter referred to as "The Game."

Binding contract - The Undersigned intentionally, legally, eligible, and as part of my due consideration exchanged for participation, agree to participate In the game.

Winner takes all - The Undersigned acknowledges that the Game is an 8 person, 3 round, single-elimination tournament. If the Undersigned loses, he or she agrees to submit completely to the stated instructions of the Undersigned's opponent to whom he or she lost for a period no less than seven (7) days, precisely 168 hours, measured from the minute victory is declared and concluding at the end of the nearest whole hour after 168 hours. Should the receiver of this obligation become similarly obligated, this obligation will transfer to the new victorious player of the subsequent round.

Limitations - The Undersigned, should he or she incur an obligation from another player, agrees that no severe or permanent financial or bodily harm shall befall the obligated player as a result of instructions followed pursuant to their obligation to the Undersigned. Physical and psychological discomfort are wholly permitted.

Officiation - The Undersigned acknowledges that, while he or she has the right to consult all Game officials, the decisions on the Game officials are final with regard to any disagreements between players in the Game.

Penalty - In the event the Undersigned fails to follow the preceding provisions of this agreement, the Undersigned agrees to submit to any and all penalties levied by the tournament organizers, including but not limited to any and all forfeiture of assets and indefinite acts of service.

I, the Undersigned, have read, understand, and agree to the above provisions without edits or reservation.

_______________________________ ____________________________

Participant Witness

Jeez,

Frank thought,

Leave it to the lawyers to give a guy last-second doubts.

Just then, the door opened again. The same doorman entered, this time followed by a downright striking female. Even in the dull light, her flaming red hair practically shone against the deep, muted tones of her solid purple evening dress. The dress, though flattering, left plenty to the imagination. Even so, Frank noted the athletic tone in her shoulders and the curve of her ample breasts. The redhead's hair only cleared the door by a few inches, and Frank suspected she'd push six feet even without the sharp black business heels that clicked as she strode across the room. The tall beauty stood straight and strode surely. She clearly hoped to be taken seriously, but Frank thought he caught some anxiety in the forward dead-set of her eyes.

Dare I get my hopes up?

Wondered Frank.

Yet sure enough, the doorman lead the lady in purple to the last empty chair, directly across from Frank. She locked eyes with Frank as she approached, and maintained the gaze as she took the proffered seat. Her eyes displayed the deep brown color of polished walnut, and her lipstick matched her hair. She held the gaze for a full five seconds before breaking to read her own copy of the contract still laying unsigned in front of Frank.

Fuck it

, Frank decided, and signed his name along the bottom. Another tournament employee promptly whisked the sheet away, leaving Frank to contemplate the beauty before him.

Alright, Frank

,

best time to play is before the timer starts

.

"Hi!" He ventured with more than a little false cheer. "I'm Frank."

The redhead looked up from her reading and locked hazel eyes with Frank again. "Charlotte," she snipped. Charlotte returned to her contract.

"I'm glad you're my first opponent," Frank said. "Looks like this tournament will prove a worthwhile endeavor for me."

"Do you mind?" Charlotte replied, this time without looking up from her legal review.

"You know, all guys fantasize about redheads." Frank replied, deliberately ignoring her response. "You're just so- exotic."

"Keep talking, prep boy." Charlotte retorted as she continued to read. "You're just digging yourself a deeper hole."

"Oh, come on." Frank whined. "You can't give me lines like that. I need at least a little challenge."

"Don't worry. You'll get it."

"I think I will." Frank smirked.

Who says psychology is a soft major? Combine it with neuroscience and you wield the most powerful force on the planet: people.

Charlotte inhaled to reply, then thought better of it. She elected to finish her contract review in silence before inscribing her name in a flowing, loopy script at the bottom and having it likewise whisked away.

Easy, Frank.

Don't overdo it. You've rattled the cage, now let the pretty bird fret.

As if on cue, a hush fell over the crowd. Frank looked around to find a late middle-aged, immaculately-dressed caucasian man with silver hair and a rigid pinstripe suit standing in the center of the game tables.

"Welcome, spectators and competitors," the man intoned. "All competitors have arrived, all contracts have be signed, and we're now ready to begin the first game."

With no further explanation, four deadpan-faced waitstaff emerged from the shadowy corners of the room, each carrying a large square tray overhand like a waiter bearing the main course. One each stopped by each game table and simultaneously lowered their burdens to their respective tables. Each tray turned out to be a marble chess board, each already set with finely-carved stone pieces of otherwise traditional design. White, Frank noticed unhappily, faced Charlotte.

"Ladies first, of course." The host intoned as chess clocks landed on each table. The courier pressed Frank's side down, starting Charlotte's clock. "You may begin."

Frank, fortunately, had studied and played a significant amount of chess in his day. Unfortunately, it appeared Charlotte could say the same. She lead with her King's pawn, and Frank followed suit, both nonverbally opting for a slugfest rather than a tedious battle for position.

"Wow," Frank commented as he picked the weaker but more aggravating of two moves, "you're actually not too bad at this. I might have to earn it tonight."

"Yuck it up, golf brat." Charlotte bit out. "You're certainly earning everything you'll get tonight. I promise you that."

Easy does it, lad

, Frank coached himself.

Just enough to take her game down a hair. She's not bad. Better she makes a mistake than to rely on skill alone with these stakes.

"So what, uh, favors got you a seat at the table?" Frank asked. He postponed an attack in favor of a pair of even piece-for-piece trades that nonetheless swapped his own undeveloped pieces for those Charlotte had fought to place. "Young girl like you, must have had to, uh, grease a few gears."

"Look who's talking," Charlotte ground out from behind teeth clenched in aggravation. "And your favors can't be worth as much as 'a pretty girl like me.' Guess you must have made up for quality with quantity." Charlotte pushed her knight forward, positioning for another attack. "All that, and you're going to lose in round one."

Frank paused only briefly before moving his bishop, apparently to pressure the knight. "As if I'd lose to a girl."

Charlotte inhaled sharply, then allowed herself a grin and met his eyes with hers. "Oh yeah, asshole? I'd say sorry to disrupt your fantasy, but I'd be lying." Charlotte moved her knight again, out of range of the bishop and simultaneously forking his rook and queen. Frank couldn't rescue one without sacrificing the other, and even the rook represented a near-insurmountable deficit.

Good thing Frank didn't plan to rescue either one. He darted the bishop forward, checking the Charlotte's un-castled King and, ironically, sandwiching it between the same rook and queen the Charlotte's knight threatened, if only she could move it instead of dodging the bishop.

"Check," Frank spoke into Charlotte's stunned stare. "Mate in two."

***

After the game, Charlotte remained, dazed, in her chair as Frank signed the necessary paperwork with the tournament officials and patiently endured the bare minimum in congratulations from men in the audience. Then, still seemingly in shock, she allowed Frank to take her hand and lead her back through the main parlor, past the smirking doorman guarding the entrance, and into the passenger seat of his car. Even his hand, which found its way firmly onto her ass halfway across the parlor, failed to snap Charlotte from her numb obedience. Only in the parking lot did she step away with a feeble, "My car-"

"-will still be here when we return tomorrow night." Frank interrupted, guiding her firmly towards his own Honda Accord. "Trust me, Red, until then your schedule, and plenty else, is full."

After a minute in the car, already on the road and headed for Frank's apartment, Charlotte finally caught up with his comment. "Oh, ha ha, very clever," Charlotte retorted sarcastically, a grimace on her face. "You don't need to be a jerk about this, you know."

"First," Frank retorted cheerfully, "who said anything about need? Tonight, I get whatever I

want

.

"And second," Frank interjected as Charlotte opened her mouth to speak, "it's really up to you. We can both enjoy ourselves, or I can have all the fun. Makes no difference to me." Frank flashed a grin at the beautiful redhead frowning at him from his passenger seat before returning his attention to the road.

"Jerk," Charlotte muttered. She turned to stare stubbornly out the window.

"If you insist." Frank sighed, fierce grin still evident. "Give me your panties."

"What? Why?" Charlotte gasped.

"Because I said so." Frank answered, extending his right hand. "If you can't mind your manners, you lose your panty privileges. Now hand them over, before you forfeit anything else."

"Fine!" Charlotte grumbled. With a quick glance around for passing cars, Charlotte reached her thumbs up her dress at the hips, gave a scoot, and quickly slid a pair of lacy purple panties to the floor before collecting them and handing them to Frank. "Happy?"

"Ecstatic," Frank replied, tossing the panties into the back seat. "Give me your bra."

"What? Why?" Charlotte repeated. "I did what you said!"

"I know. I just want your bra. Don't make me ask again."

Charlotte opened her mouth to retort, then thought better of it. Grumbling under her breath, Charlotte popped the clasp of her bra through her dress's thin fabric, yanked it out through her left sleeve, and disdainfully presented it to Frank. As the car crossed a large bulge in the road, Frank glanced over to observe Charlotte's previously-hidden D-cup breasts bouncing freely under the dress, puffy nipples protruding slightly from underneath the fabric. Smiling to himself, Frank took the bra, gave it a twirl around his outstretched finger, then tossed it next to Charlotte's panties in the backseat.

"Good girl!" Frank cooed sarcastically. "We're still about 10 minutes from my apartment. Swallow my cum before we get there, and I'll let you keep your dress until we get inside."

"No fair!" Charlotte protested, horrified at the prospect of public nudity. "You've wasted half the trip already!"

"I'm not the one who needed two tellings to get her underwear off. Nine and a half minutes."

"Jerk." Charlotte spat, as she reached for Frank's crotch and lowered his zipper.

"You can try," Frank replied, "But 'suck' is a better strategy if you want to keep that gorgeous dress out of my backseat."

Rather than respond, Charlotte focused on maneuvering her way through Frank's briefs and extracting his erect cock.

Could be worse

, Charlotte thought to herself.

Probably five or six inches, slight upward curve, enough girth I can barely get my hand all the way around. At least this won't bore me or rip me in half. Thank god for mid-sized favors.

With a sigh to herself, Charlotte began stroking Frank's cock. Frank permitted himself a satisfied sigh at the touch of Charlotte's soft skin, but otherwise appeared unaffected.

Shit,

Charlotte thought to herself as the car's clock ticked off another minute.

This isn't working

. With an audible sigh, Charlotte stopped stroking long enough to coat her fingers with a thin layer of saliva.

"Better," Frank commented as another minute passed. "But please, keep wasting time. It's your dignity on the line."

Shit.

Charlotte thought.

Well, I'll probably be blowing him soon anyways. I might as well avoid disgracing myself in public.

With a little maneuvering, Charlotte brought her legs to a kneeling position underneath herself and turned her ass towards the passenger door. Then, with one more resigned sigh, she leaned over the gearbox and pushed Frank's cock past her lips.

"Hnnggh,"

Frank moaned as he felt Charlotte's lips and tongue slide along his shaft. "Much better. We may make a good girl out of you yet." With his left hand still on the wheel, Frank reached with his right to grab the hem of Charlotte's dress. With a quick pull, Charlotte's panty-free pussy and posterior came into full view of any drivers lucky enough to pass them passenger side. Frank took a moment to admire the sight: bare unsunned skin, stereotypically pale for a redhead, pleasantly curved and perfectly-sized for grabbing a handful, up in the air and exposed for all to see. He also noted the reflection of her pussy in the window, a pair of soft, pouting lips bare of any carpet to match the beautiful drapes bobbing in his lap. With a chuckle, he brought his open palm down squarely on Charlotte's right cheek.

"Mmpph!" Charlotte protested around the flesh filling her mouth. Frank savored the vibrations.

"Shh," Frank cooed, resting his right hand on the back of Charlotte's head and lacing his fingers into her scarlet locks. "Don't get distracted, now. You have a job to do."

Rather than respond, Charlotte focused on the task at hand, or rather at mouth. She started with a slower rhythm, slow downward strokes and even slower up, with the intent to speed up as she felt Frank near his climax. Each time she hit bottom she relaxed her lips and throat, allowing the soft flesh to press in on and envelop the long pole penetrating her mouth. After a prolonged slide up Frank's shaft, she paused long enough to swirl her tongue around the head, breathe, and repeat the process. Too soon, however, she felt the car slow, turn, and park. As a last resort, Charlotte shoved another inch of shaft down her throat and gave several swallows, hoping the throat massage would send Frank over the edge.

"Good girl!" Frank exclaimed, then pulled the desperate redhead off his now glistening cock and up to his mouth. "Mmpph," Charlotte protested before surrendering to the kiss. With her lips still soaked and breath still hot with exertion, Frank and Charlotte skipped sensual and went straight to a downright invasive exploration of one another's open lips.

"Not a bad blowjob," Frank commented, the same shit-eating grin reemerging as he held his hand out, palm up. "If only you'd gotten started sooner. Fork it over. Keep the heels."

With a moment's hesitation and an angry glare toward Frank, Charlotte reached back down to the hem of her dress and, with an exaggerated sigh, rolled it up and over her hips, bosom, and head like a wet T-shift, auburn curls popping free from the neckline and falling back to her now bare freckled shoulders. Charlotte quickly balled up the dress and chucked it past Frank's outstretched hand into his face.

"Thank you." Frank tossed the dress into the backseat to join Charlotte's erstwhile undergarments. "Shall we?" Frank exited through the driver door, walked around to Charlotte's side, opened her door, and held out his hand like a gentleman escorting a date. "Best hurry up, dear," he remarked, eyes dropping to her puffy, fully-erect nipples. "Looks like you're feeling the chill."