Winner Takes All: Round 02

Frank slid around Charlotte and out of the shower. He toweled off and dressed quickly in a comfy T-shirt and blue jeans. While he waited, Frank retrieved his phone from last night's pants, plugged it in for a quick charge, and made a pair of phone calls.

Ten minutes later, Frank heard the water stop. Another ten, and Charlotte emerged from the bathroom in a cloud of billowing steam. She had Frank's spare towel wrapped around her torso, positioned so it came up an inch above her nipples and maybe half an inch past the bottom edge of her ass. Her hands were up behind her head, airing out her still-damp crimson locks. She seemed- refreshed.

"Sorry I don't have a hair dryer." Frank said. "Don't usually need one. No worries, though. You've got an appointment at the salon later.

"Here, get dressed," Frank ordered, tossing her one of his smaller T-shirts and an old pair of sweatpants. "Your dress is still in the car, and I'm not gonna have you prance around naked in broad daylight. Not yet, anyways."

Charlotte shot him a glance at the last comment, then shrugged off the towel and dressed as told. Frank treated himself to one more eyeful of her banging body before it disappeared under his old clothes.

Damn, she looks good no matter what she's wearing, Frank thought. Even under her baggy ensemble, Charlotte's large, firm breasts and plump ass were evident.

I'll have to make sure I enjoy that fully today, Frank reminded himself. It could be my only chance.

****

First stop was the Lingerie store. "You've got to feel sexy to be sexy," Frank explained. "Besides, I've always wanted to do this."

"This" turned out to be an hour-long tour of the entire store. Frank picked out a dozen different ensembles, all of which Charlotte got to model for him in the changing rooms. In Frank's opinion, every set looked incredible framing Charlotte's body. In the end, he narrowed it down to two options: a black and red set complete with garter and stockings, and a more classic white lace thong and bra that, if not technically push up, certainly made Charlotte's tits appear even more appetizing than usual.

Of course, there was only one way to decide.

"Bend over," Frank ordered. "Hands on either side of the mirror."

Charlotte complied. "What are you-? Oh!" She exclaimed as Frank pulled aside the thin red-and-black fabric she now wore and plunged two fingers into her already damp snatch.

"Shh, you'll get us kicked out." Frank reprimanded as he smacked her lightly on the rear. "I need to see how they look when you're in heat. Now be a good girl and keep quiet."

Frank started pumping his fingers in and out of Charlotte's pussy and turned his head to watch her in the mirror. She had her eyes closed, teeth biting into her lower lip, and her ample tits were already swinging beneath her in rhythm with his thrusts, even contained as her breasts were in the upper half of her current outfit.

In fact, now that he thought about it. Charlotte's hips were definitely assisting him as he finger-fucked her. Frank added another finger and watched as she scrunched her eyes tighter and bit down even harder on her lower lip. He kept pumping, and within minutes he felt her pelvic floor begin to twitch as her orgasm neared.

"Okay, switch." Frank commanded as he withdrew his fingers.

Charlotte emitted a desperate mewl, still panting. "Wh- What?"

"Switch." Frank repeated. "We need to try the other set."

Charlotte turned her head to face Frank. With her pussy exposed, face flushed, and chest still heaving, she looked like she wanted to drag Frank to the carpet and mount him right now, to hell with his orders. After a second, though, she caught her breath regained control. The panties hit the floor, along with the attached garter and stockings. A second later, the bra joined the pile.

Charlotte quickly donned the simpler white lace set. Without waiting for orders, she bent over the mirror again. She made eye contact with Frank in the mirror, but instead of her usual dagger-gaze, this time she was silently begging him to continue. She even wiggled her ass at him.

"Good girl." Frank said. He yanked the panties down to Charlotte's knees and resumed her finger fucking. This time, Charlotte made no effort to hide her desires, violently bucking her hips back to meet each thrust. Seconds later, her orgasm built again.

"Ah. Ahhh! AHHH!" Charlotte wailed in a classic pre-orgasm crescendo.

Seconds before she would have cum, Frank removed his fingers. "Right, white it is," he commented nonchalantly, as though picking out groceries at the store.

"But! But!" Charlotte pleaded.

"No buts." Frank replied. "At least, not that kind. Be a good girl, and I'll fuck you in the next store. Promise."

Frank kept his promise.

"The next store" was a high-end fashion boutique with a good selection of exquisite and expensive evening gowns. Frank picked out a several different dresses in different colors, exchanged a few whispered words with the sales attendant, and lead a hot and willing Charlotte back to the changing room.

Minutes later, true to his word, Frank had Charlotte once again bent over in front of the changing room mirror. He had one fist wrapped in her auburn locks for leverage, the other clamped over her mouth, and his cock buried in her cunt. She was wearing the first dress, a minimalist little black number that left her shoulders bare and would have come down in a tight cut to mid thigh, though the lower half was currently bunched up around her waist. Her brand new panties, of course, were once again around her knees.

"Be. Quiet. Red." Frank grunted with each thrust. "Sales. Guy. Knows. I'm. Fucking. You. But. We. Have. To. Keep. It. Down."

"Mmph. Mmph. Mmph." Charlotte replied through the hand gagging her.

Charlotte came quickly, legs spasming in what Frank now recognized was her typical fashion. Frank didn't even slow down. He continued to plow her even as she slumped forward against the mirror, causing Frank's thrusts to audibly shake the walls.

"Excuse me!" A female voice said from just outside their stall. "Are you alright in there?"

Frank reluctantly slowed and pulled Charlotte off the wall. She didn't respond. She just let her upper body hang, legs still splayed and ass in the air like a cheerleader stretching her inner thighs before a routine.

"Yeah, we're fine." Frank replied, trying to force himself to sound calm even as he kept thrusting. "She just, uh, slipped while we were wrestling her into a dress. Damn things don't have much wiggle room."

"Alright," the voice replied hesitantly. "Just... Try to be more careful."

"Will do." Frank responded, even as he built his rhythm up again. He left her in her folded standing position, ass in the air, as he continued to thrust, using his hands to work her hips back and forth in time with his dick. Charlotte whimpered softly as he went.

Charlotte's perfect ass suspended in the air, her pathetic whimpers, and the feeling of her warm, tight pussy post-orgasm were too much. Minutes later, Frank came, continuing to pump steadily even as he shot his seed deep into Charlotte's womb.

As he felt his post-orgasm high coming on, Frank held out long enough to lower Charlotte and himself gently to the floor. Charlotte lay sprawled on her side, semen leaking from her snatch, while Frank reclined against the wall, silently grateful that the changing rooms in this boutique were floor-to-ceiling.

They laid there a while, each content to enjoy the afterglow. Somehow, no one else came to check on them. Either the female employee had decided she didn't want to know what was going on, or the twenty Frank slipped her male colleague had eventually done it's job.

"Right." Frank finally said. "Not this one. Too generic. Try the next dress."

Eventually, they went with a deep green garment that came down to just above the Charlotte's knee. According to Frank, the cut emphasized her outstanding ass; the neckline dipped just enough to expose a hint of white lace from the right angle, and most importantly, Charlotte's crimson crown stood out even more brilliantly against the dress's cooler, darker tones. The dress, with matching shoes, carried a substantial price tag, but Frank forked over his card without hesitation.

"Money well spent." Frank responded to Charlotte's curious look. "Besides, I have excellent financing."

Finally, they stopped at the salon. For once, Frank kept sex off the agenda. While the stylist went to work on Charlotte, Frank made himself comfy in the waiting area and browsed game strategy articles on his phone.

An hour later, Charlotte remerged. Frank took his time examining his prize, walking slow circles, gaze sweeping up and down Charlotte's slender form. Her hair was now immaculate, falling in gently cascading waves that weren't quite curls to rest on her exposed shoulders. Her locks stood out sharply against the dark green of the dress. The contrast drew attention to the curve of per pale neck, then drew the gaze down to the curve of her bust and hips. Frank couldn't be sure, but it looked like the undergarments were doing their job too, as Charlotte's already impressive curves looked exquisite framed under the dress. Where the dress ended, Charlotte's toned knees and calves extended, ending only where the matching heels completed the ensemble.

Frank grinned. "Perfect."

After forking over another pretty penny to the salon, Frank and Charlotte headed back to the apartment, stopping only for food to bring home for dinner. When they got back, the digital clock over Frank's bed read 4:22pm.

"Okay, Red. I'm gonna take a nap. The game starts at 10pm, so give me a friendly wake-up around seven. Until then, your only responsibility is making dinner. Other than that, get some rest."

With that, Frank made his way straight to his bed and collapsed. He closed his eyes, and memories of the afternoon's escapades danced pleasantly through his mind.

Only minutes later, it seemed, Frank felt a warm, wet sensation envelop his cock. He inhaled sharply, and his eyes flashed open.

Charlotte stood next to his bed, still dressed to the nines. She was bent at the waist, her sculpted locks held carefully out of the way in one hand, her mouth impaled on Frank's cock. Though Frank could have sworn he just laid down, the clock now read 6:59pm.

As he watched, Charlotte began to ever so slowly bob her head. Three seconds up, three seconds down. Clearly, Charlotte intended to keep her hair out of harm's way. Not that Frank minded. The slow, sensual pace created the perfect sensation to chase Frank's drowsiness away. He placed his hands behind his head and exhaled, content to let Charlotte work her charms. Frank savored the pressure of her lips working its way slowly up and down his shaft, along with the heat surrounding his head.

Frank always woke up horny, and in spite of his and Charlotte's earlier activity he felt the pressure once again build in his balls. With the hand not holding her hair, Charlotte reached between Frank's legs and began not-quite-tickling the base of his scrotum, a light many-fingered stroking rhythm that only further coaxed the cum from Frank's loins.

"Ungh!" Frank grunted in surprise, and seconds later erupted into the soft furnace still sucking at his shaft. Rather than recoil, as Frank had expected, Charlotte seized the opportunity to shove her face further into Frank's crotch, sliding Frank's cock into her throat until her nose brushed his pubic hair. She swallowed as Frank came, her throat contractions milking even more semen from his now-depleted reserves. Frank arched his back in response to the pleasure-pain, somehow shoving his shaft an extra inch into Charlotte's mouth. He gave a few more involuntary twitches before collapsing back onto the bed, and his now softening member finally sliding out from between Charlotte's lips and flopping limply onto his lower belly.

"Good girl." He breathed.

Charlotte swallowed again, then grinned. "Thank you, sir," she answered. "When you're ready, dinner is served."

She straightened, tugged her dress back into place here and there where it had bunched while she bent over, and strutted back into the kitchen.

I have to win tonight. Frank thought to himself. No way in hell I'm giving that up.

***

Two hours later, both had eaten, Frank had dressed himself (casual two-piece gray suit, slim cut, and a fresh white button-down), and Frank and Charlotte found themselves pulling in to park next to Charlotte's car where she'd left it in the gambling den parking lot the night before.

"Aren't we a bit early?" Charlotte asked, indicating the car clock. It read 9:05pm.

"Maybe, but I want to give our audience and our competition a chance to see you," Frank answered. "Let their desire incubate, you know? You're my secret weapon, after all. I want to dangle you in front of everyone before they have the game to distract them."

"You're the boss, sir." Charlotte replied. Frank wasn't sure in the dark car interior, but he thought he saw her smirk."

"Good girl. Let's go have some fun."

Frank stepped out, walked around, and helped Charlotte out of the passenger seat. At first, he wasn't sure he recognized the woman that emerged.

Gone was the beautiful but young and visibly nervous girl Frank had first met last night. A smoldering, fiery succubus had apparently replaced her.

First, Charlotte swung her long, slender calves out of the car, like an actress exiting her limo onto the red carpet, rather than Frank's economy sedan in a parking lot. Light from streetlamps reflected off the pale, toned skin, with promises of more to come.

Those promises were soon fulfilled. With a hand from Frank, Charlotte planted her heels and stood. As she emerged, she subtly pushed her chest out, causing the contours of her breasts to stand out against the tight fabric. She tossed her hair and brushed a few stray strands away from her eyes, and for a moment Frank could have sworn he was watching a shampoo commercial. She turned to face him, lips pouting ever-so-slightly and eyes smoldering with sex appeal.

"Ready, baby?" Charlotte cooed as she stepped closer, wrapped an arm around Frank's waist, and pressed her chest to his ribcage.

"Y'know? I think we are!" Frank replied cheerfully.

Charlotte looked up and locked gazes with Frank, and for a moment the nervous young girl was back. "How was that?" She stage-whispered.

"Perfect."

With Charlotte's arm still around his waist, Frank wrapped his around her shoulder and guided her to the front door. Just like last night, Frank knocked out the password: two knocks, then one, then one again. Same rhythm as the rules: winner takes all.

Once again, Frank heard the deadbolt slide open, and the smells, noise, and sheer atmosphere of the gambling den washed out the door and enveloped the young couple. The doorman beckoned them inside, and soon they were once again in the back game room.

They found the layout unchanged: central well-lit game area, three tiered rows of plush chairs in in the shadows around the arena. Only the number of tables had changed, now two instead of the previous evening's four. Frank took it as a not-so-subtle reminder that half the field had already enslaved themselves to their opponents.

Even though Frank and Charlotte were an hour early, a small crowd had already arrived. Frank couldn't be sure, but he thought he recognized several faces from last night, one or two of whom he hoped were fellow competitors.

"Let's play." Frank whispered to Charlotte. He allowed himself to break into a well-practiced high society smile, and a sideways glance showed him Charlotte had done the same.

They spent the next forty minutes or so schmoozing. As expected, Charlotte quickly attracted a crowd, especially among the better-dressed middle aged men present. Two, in particular, continued to converse with Frank and ogle Charlotte far longer than anyone else in the room seemed to find appropriate.

The first, a fifty-something mildly balding man, introduced himself as Joe McCurdy. Joe initially kept up the pretense of conversation with Frank, even though his eyes never stopped scanning the redhead on Frank's arm. Charlotte played her part well. She arched her back, causing her breasts and butt to stand out against her dress. As McCurdy watched, she would subtly shift her weight from foot to foot, causing her ass to undulate under the fabric already stretched tight across it. Frank thought he even saw Charlotte briefly lick her lips. Whatever she did, McCurdy trailed off mid-sentence for the second time.

After McCurdy lost his train of thought twice, he finally gave up any pretense of courtesy.

"Damn, that is one fine piece of ass you've got there, son," he commented. "I remember it from last night. You're one lucky son of a bitch. I can't wait for the chance to add that hot tail to my collection. Of course, I made out pretty well myself last night. Won myself a hot little blonde number. Now that I mention it, where did that little minx get to?"

McCurdy finally took his eyes off Charlotte to look around. Within seconds, another woman emerged from where she'd apparently been lurking in the crowd. She wore an honest-to-god old-fashioned maid's outfit, complete with short black dress accented with white lace, black hairpiece, white thigh-highs, and five-inch heels. The hairpiece framed her platinum-blonde hair, currently tied in a bun to suit her costume. Frank guessed that she would naturally measure five foot eight or nine; with the heels, she topped six feet, a fact only emphasized by the too-short maid's dress threatening to expose whatever she might be wearing (or not wearing) up that skirt. The heels put her bust almost at Frank's eye level. Frank could tell she wasn't overly busty, but the push-up bra she clearly wore made the B-cups she did have quite appealing nonetheless. She also wore a simple black collar and circular metal tag tight around her neck, clearly McCurdy's personal addition to the ensemble.

Her face was set in a neutral expression, but Frank thought he could see the scowl it hid, an expression that quite clearly communicated her displeasure that McCrudy had remembered to look for her. She held an expensive-looking glass of scotch in one hand, which she offered toMcCurdy.

"Right here, master." She intoned. "Here's your scotch, master, just as you requested."

"See! What'd I tell you?" McCurdy exclaimed as he took the drink. "Total bombshell. And let me tell you, she looks just as good without the outfit, if you know what I mean." He winked.

"I can imagine." Frank replied.

"I'll be you can, m'boy. I'll bet you can. And Colleen here would just love to indulge those fantasies, wouldn't you my pet?" Joe asked. Colleen nodded her head slightly in a gesture of grudging acceptance. "Well, best of luck to you. Unless, of course, you're my opponent. In which case, I promise to treat your chew toy just as well as I treat mine."

McCurdy winked again. He placed his hand on the back of Colleen's upper leg and snaked it quickly up beneath the hem of her dress. Colleen flinched, but otherwise ignored the grope. With his hand still up Colleen's skirt, McCurdy and his prize finally wandered away.

"Interesting chap," remarked a velvet smooth voice at Frank's side. "I find myself wondering how he made it this far."

Frank and Charlotte turned to face the voice, who turned out to be a well-dressed, graying gentleman in an immaculate suit. Given his hair, tone, and posture, Frank put the man in his late forties.

After that, Frank and Charlotte's attention was quickly drawn to the woman on his arm. She was also blonde, but a dirtier, more natural tone sometimes achieved by brunettes when they spend time in the sun. She wore a white blouse, charcoal blazer, and matching pencil skirt. Sensible stud earrings with gleaming rubies and a similarly sensible pair of three inch white monotone heels completed the ensemble. All told, the dirty blonde looked like she'd come straight from the office.