Winner Takes All: Round 02

High Stakes: Winner Takes All

Round 2

Frank woke up with the faint smells of sex lingering in his nose, a gorgeous naked woman cradled in his right arm, and a fresh hardon itching for attention.

It's going to be a great day! Frank thought to himself.

Frank let Charlotte sleep for another minute. He admired the messy red curls covering his right shoulder, the cute pale freckled face resting slack on his chest, and the tops of her large, pale breasts pressed against his ribcage.

Memories of the previous evening danced through Frank's memory: Charlotte, strutting across the gambling den in her lovely purple evening gown; Charlotte, eyes wide in shock when she realized she lost the game, forfeiting herself to Frank for the week; Charlotte, on her knees in the passenger seat of his car, head bobbing in his lap while her pale ass and pussy reflected off the passenger window with the passing streetlights; Charlotte, buck naked on her knees in front of his bed with his cock stuffed in her mouth; Charlotte, impaled on his shaft in a standing reverse cowgirl as her warm pussy slid up and down his pole; Charlotte, face down ass up on his apartment floor, crying out in pleasure-pain as he reamed her freshly deflowered asshole, clenching and sputtering in her first anal orgasm as he came deep in her bowels.

It's enough to make a guy want seconds.

Frank began stroking the beautiful redhead's hair, and gradually Charlotte stirred. Still half asleep, she gave a comfy-sounding little moan and snuggled closer. Frank continued stroking her hair, and a few second later Charlotte's body went stiff and her eyes snapped open.

"Morning, beautiful!" Frank said cheerily. "Sleep well?"

"Well enough." Charlotte muttered.

"Glad to hear it." Frank replied. "Say, you know what? I could really go for a blowjob."

Charlotte glared daggers at him for a full five seconds. Then she pushed herself up to her hands and knees, shot Frank one last glance, and dutifully slid her way down to his groin. Frank pulled the blanket off the bed and treated himself to the sight of this milky-skinned nubile preparing to make his morning.

"Show some enthusiasm and you'll find yourself in my good graces," Frank advised.

Charlotte paused, mouth hovering over Frank's cock, long enough to consider the statement, then slowly and dutifully engulfed him. Frank threw his head back and moaned as the warm, wet feeling gradually enveloped him, soothing the ache that was equal parts morning libido and leftover tenderness from last night's activity.

"Mmm, good girl," he cooed. "Nice and slow. Just like that. Perfect. Stick your ass up. Make sure I can see it. Good girl. Feel free to moan if you'd like. Ooh, yes, nice. That's fucking great."

Once Charlotte found her rhythm, Frank stopped coaching and let himself enjoy the ride. Charlotte continued her steady, thorough pace. Occasionally she paused at the head, swirling her tongue around it while slowly milking the pole with one hand. Twice she moved down to bathe his balls with her lips and tongue, hand still stroking his shaft. All in all, Frank decided, it was an excellent morning blowjob, and soon he felt the pressure in his balls building.

"I'm getting close. Be a good girl and swallow for me, then keep milking with your mouth as I come down." Frank instructed.

Charlotte did just that.

There's something special, a distant part of Frank's mind noted as he climaxed, cock spasming where it rested on Charlotte's tongue, about cumming in a girl's mouth.

As Frank finished, Charlotte swallowed twice and continued to orally massage Frank's member. Frank twitched several more times out of sensitivity before letting out a long exhale and melting back into his bedsheets. When he opened his eyes, however many minutes or possibly hours later, he found Charlotte's mouth still wrapped around his now half-flaccid dick, eyes looking up questioningly at her liege.

"Good girl. That's enough." Frank breathed. "Give me another minute. Feel free to freshen up, and you're welcome to drink anything in the fridge."

Frank closed his eyes again as Charlotte released his cock, stood, and padded off to the bathroom, her toned asscheeks swaying as she walked. Frank heard the faucet start, followed by the sounds of water splashing and gurgling.

Frank waited another minute or two, letting himself come down slowly from his post-orgasm high. Then, with a groan, he sat up, planted his feet, stood, and made his way into the kitchen. He found Charlotte, still naked, bent at the waist with her head in the refrigerator. Frank admired her puffy lips, still tinged red from last night, framed neatly by her slender thighs. He also, he thought, noticed the faint traces of dried moisture running down the backs of her legs.

"You tempt me, Red," Frank commented, "but we'll probably have to wait at least a few more minutes. Milk and OJ are both still good, if you were wondering. Hand me the eggs, would you?"

As Frank set about scrambling eggs for the two of them, Charlotte apparently decided on the orange juice and poured herself a tall glass. She sat down at the small table and began to sulk. Frank found it hard to take her pouting too seriously, given she was still buck naked.

When the eggs were ready, Frank divided them onto two plates, grabbed a pair of forks, and joined Charlotte at the table. Charlotte eyed the eggs hungrily. She looked up hopefully at Frank, and he gave a short nod. Without further hesitation, she began shoveling food into her mouth.

Frank took a more leisurely pace, and he gave Charlotte a few minutes to take the edge off her hunger. As she was slowing down and starting to hunt down the smaller pieces around the plate's edge, he spoke up.

"I've been thinkin, Red. It'd be nice to have an advantage in the next round. You know, something to tip the odds in my favor.

You were a little out of it last night, so you might not have noticed; every man in that room had is eyes on you, especially the men who won their rounds. I'll bet they were busting in their pants, imagining themselves plundering the hot mouth and that juicy ass. There were other hot girls, sure, but I'm not sure there were any hotter than you. That and your red hair makes you the exotic prize everyone wants. I honestly still can't believe I landed you in the first round. Lucky me."

"Yeah, lucky you." Charlotte grumbled.

"I mean, I knew that ass would be tight, but damn," Frank continued. "You. An anal virgin. Well, ex-virgin. What a treat. My cock's getting hard again just thinking about it.

"Anyways, here's the deal. I want you to be my trump card. I've got to make a few phone calls, then we'll go out and get your prettied-up for tonight.

"And not like a slut," Frank interrupted himself. "Most of the men in this game are wealthy enough to bribe any slut they want into bed. No, sex appeal to them is a classy, powerful woman that doesn't have a price. You've already got that, but we're going to turn it up to eleven.

"I need your help, though. I could just order you to wear whatever I say, of course, but you've got to sell it. You've got to mean it, feel it, and I can't order you to feel something. So here's the deal: you play along. Sell whoever I'm playing this fantasy. Make them want you so badly they can't think straight.

"Do that, help me win, and you'll be my second-in-command. You'll still have to follow my orders, of course, but I promised to take out my more extreme urges on the other girls. That, and you'll get to play with our toys, too. Way better than a week as some middle-aged man's sex slave, I'll bet. What do you say?"

"Do I really have a choice?" Charlotte grumbled.

"Yeah, actually, ya do." Frank replied. Charlotte recoiled slightly, blinking.

"I can't force you to feel anything." Frank continued. "You're hot, sure, but if you're going to be the smoldering blaze of oozing sex appeal we need, you're gonna have to choose to be into that."

Charlotte eyed Frank suspiciously for a few seconds, then zoned out, staring into the space over Frank's right shoulder and contemplating. Frank let her, content to admire the nude nubile with his peripheral vision.

After a full minute's consideration, Charlotte made eye contact again. "Fine." She answered. "I guess I'm in. What now?"

"Just so we're clear," Frank said sternly, "You're still mine. I won you fair and square. I think we'll both be happier working as a team, but I'm still in charge. You got that?"

"Yeah, I get it." Charlotte replied.

"Good girl. Now get under the table. I'm going to have you bent over it in a second, and you need to get me ready."

Charlotte flashed Frank a stern look, then sighed audibly. Her chair screeched softly as she slid it back from the table. Then Charlotte slumped forward and crawled under. Frank watched her pert, pale cheeks disappear under the table just before he felt Charlotte's warm hands on his thighs, near the knees. They slid upwards, eventually meeting at his crotch. One hand she rested on top of the base of his shaft, while the other gently scooped up his balls from beneath and began fondling. Soon, Frank felt Charlotte's tongue join the hand massaging his genitals. Only then, Frank allowed himself to look down. As expected, he found the pale nude redhead on her knees between his legs. Her messy auburn locks and freckled face would be downright cute if Frank couldn't also he her scrumptious ass and full, pale breasts with their erect, rosy-tipped nipples. That, and the fact that she was currently french kissing his left nut while tickling the right, eyes shut as she apparently focused on the task at hand.

After giving the right testicle the same oral treatment, Charlotte slid her warm tongue up Frank's shaft and, smoothly continuing the motion, lowered her head back down, only this time she impaled her face on Frank's cock as she descended.

"Mmm," Frank vocalized as her hot mouth engulfed him. "That never gets old."

Frank allowed Charlotte to pleasure him for several minutes. Unlike the previous evening, when she'd been trying to get him off as quickly as possible, she went slowly. She pressed him deep into her mouth and throat, even gagging two or three times when Frank felt himself hit bottom and start to curve downward.

Frank gently but firmly grabbed hold by the roots of Charlotte's hair and pulled her in for one more deep stroke. He held her there for three seconds, and Charlotte, for her part, relaxed and took it.

"Good girl," Frank exclaimed as he pulled her off and released her. Charlotte stayed on her knees, breath panting and chest heaving beneath her breasts, several strands of deep-throat saliva dripping from her open lips.

"Now get up here and straddle me," Frank ordered as he, still sitting, pushed his own chair away from the table. "I want you to get yourself off. You've earned it."

Charlotte swallowed and seemed to catch her breath. She obediently crawled out from under the table and stood. She swung one leg then the other over Frank's splayed legs, pressing her breasts into Frank's face in the process. Frank wrapped his arms around Charlotte and, with one hand on her lower back, directly above her ass crack, guided her hips onto his stiff member.

Apparently, Charlotte hadn't gone unaffected by the morning's activities. Frank's tip found the entrance to Charlotte's pussy dripping in anticipation. As Charlotte lowered her hips and Frank slid inside, the rest of his cock found an equally warm reception.

"Now ride me." Frank commanded. "I want to feel you pleasure yourself with my cock."

Charlotte needed no further encouragement. Her first few strokes she made relatively slow and long as she loosed up and got used to the cock filling her. Then, she began to impale herself in earnest, withdrawing almost to the head before slamming herself back down, ramming Frank's cock into her over and over.

The motion itself wasn't as pleasurable as the long, fluid motions Charlotte used to get Frank off the night before, but what the rhythm lacked in technique it more than made up for in the desperate heat Charlotte exuded as she worked herself into a frenzy, combined with the twitches and spasms from insider her pussy. Frank helped himself to two handfuls of her incredible ass and pressed his face deeper into her cleavage. Every few seconds he let one cheek go long enough to spank her, prompting her pelvic muscles to spasm again.

"That's it. Ride that cock. Fuck that cock. Impale yourself on it. You've been such a good girl. You deserve this. You earned this. Get yourself off. Make yourself cum. Fill every crevice of that pussy with my meat. I'm going to enjoy fucking you into a limp puddle of pleasured pussy. I know you want it. I know you need it. Cum for me, baby. Ride that cock and let me feel you cum."

"Oh fuck. Oh fuck. Oh FUCK! OH FUCK!" Charlotte cried, her voice getting higher and louder with each thrust. Frank could sense the pressure building, could feel her spasms become more chaotic and her rhythm falter as her orgasm neared. Frank found an even firmer purchase on each asscheek and guided her, enforcing the rhythm, ensuring Charlotte couldn't have stopped even if she wanted to.

"Oh fuck! OH FUCK! OOOHHH FFUUUUUUUCCCCKKKK!" Charlotte screamed as Frank felt her entire vagina clamp around his cock like a vise, felt through her ass as her legs shook uncontrollably from orgasm and muscle fatigue. Charlotte slumped on top of him, but Frank slowly pumped his hips up and down in time with his hands as they manually worked her ass in the same motion. Frank felt the effects of his efforts through his cock as the inspired after-tremors radiated outwards from Charlotte's cervix.

Had he been trying, Frank probably could have cum right then and there. As it was, his prick was painfully hard and demanded prompt relief.

Charlotte still slumped limply against him, her breathing slowing but still heavy. Frank didn't let that stop him. He wrapped his arms around Charlotte's back and stood, cock still buried to the hilt inside her. He took a half step forward and released her onto the table. Plates and silverware from breakfast clattered to the floor, but Frank ignored them. He pumped into Charlotte's snatch a few times. He admired her naked body laid out in front of him, breasts bouncing in time with his thrusts, hair splayed out in a halo around her head, eyes still closed and mouth hanging slightly open. Apparently, her mind had yet to return from post-orgasm oblivion.

It was quite the sight, Frank noted. Still, he knew she'd look even better face down ass up. He pulled out long enough to throw one of her legs over the other, flipping her onto her stomach. She went tits down on the table, legs hanging down to the floor without supporting any weight, ass up in offering. Just like he'd imagined.

Frank pressed the tip of his cock, still wet with Charlotte's juices, against her puckered rosebud. At this, he felt her tense, and heard her let out a small grunt.

Not yet, Frank decided. He moved the head down an inch and plunged back into her warm, relaxed cunt. Charlotte melted back into the table and let out a low, soft moan, apparently all the communication she could currently muster.

Fine by me, Frank thought. He started fucking in earnest, slamming his hips into Charlotte's full round ass over and over and over again. The table slid an inch or so with each thrust, until the other end bumped up against the near wall. Frank shuffled forward as he went, never stopping. Hell, but he didn't think he'd ever tire of plundering this woman's hot snatch. The way the warm walls hugged his cock, particularly after she'd orgasmed, soft and relaxed but still tight, drove him wild. Charlotte, for her part, just let him have her. She continued to grunt softly with each thrust, eyes still closed, a small puddle of drool forming under her open mouth. Frank felt the pressure in his balls build for the second time this morning, and he didn't hold back.

With a half-groan, half-roar, Frank emptied was remained in his loins into Charlotte's willing pussy, continuing to thrust wildly until he felt his dick start to protest from overstimulation. He slowed to a stop with a few more strokes, then slowly withdrew his already shrinking member. He stumbled back the now several steps to his chair and collapsed, breathing heavily, as Charlotte continued to moan quietly from her own resting place on the table. They both remained in place for a minute, recovering, the only sounds in the room their heavy breathing and the faint sound of Frank's semen trickling and dripping down Charlotte's still-splayed legs and onto the floor.

Frank recovered first and reluctantly hauled himself to his feet. "I'm going to hop in the shower," he spoke towards Charlotte. "When you've got your wits back, come join me."

Frank half walked, half stumbled into the bathroom and turned the water on. Within minutes, the bathroom filled with steam. Frank gladly stepped into the tub and immersed himself under the hot water. How long he stayed there, letting the almost painfully hot water cascade down his neck and back, he wasn't sure. Eventually, the far edge of the shower curtain was pulled back, and Charlotte's adorable freckled pace poked its way in.

"Get on in," Frank ordered. "Soap's in the dish. I want the VIP treatment."

Charlotte, still naked of course, pulled the curtain back further and stepped into the shower stall. The stall wasn't really designed for two, but there was enough room to maneuver if the occupants didn't mind some incidental contact, which Frank certainly didn't.

She started with his chest and arms, working the soap into a lather and slowly, sensually running her hands and the bar over Frank's bare skin. Frank watched her, admiring the water running down her breasts, core, and hips. Then he turned around, leaning his forearms against the near wall, and let Charlotte wash his back. She went slowly, taking the time to gently massage around his shoulder blades. Frank let out a long sigh of relief and let her work. She worked her way down his back to his ass, then dropped to her knees to work his legs, all with the same care she'd shown up top.

When she finished the legs, Charlotte gently grabbed Frank's hips and encouraged him to face front again. Still on her knees, Charlotte lathered more soap onto her hands and gently took hold of Frank's genitals. He twitched at first, from surprise and lingering sensitivity, then forced himself to relax. Charlotte gently pumped one soft, soapy hand up and down Frank's still-limp shaft, while the other swirled around and over his balls. Even though he'd already gotten off twice that morning, Frank felt his loins stir again.

At the sight of Frank's cock twitching and beginning to harden, Charlotte looked up and smirked. Once she had his cock and balls good and clean, she rinsed her hands in the water running down Frank's abs. Then she snaked her hands around to his ass cheeks, pulled gently, and slid Frank's now half-erect cock back into her mouth. Guiding him by the ass, she slowly pumped Frank into her mouth a half dozen times, eliciting several groans from the man towering over her. She pulled off slowly after the last stroke, sat back on her heels, licked her lips, and looked up questioningly.

"That's my girl." Frank cooed. He bent at the waist, lifted her chin, and kissed her softly on the upper lip. He felt Charlotte respond, subtly thrusting her chest and breasts out and sucking hungrily at his lower lip in turn. Frank let her have a moment, then broke the kiss. "That was wonderful. I'm not quite ready to go again, and we have errands to run. Take a few minutes in here for yourself, then we'll get going."