Winner Takes All: Round 03

Frank stopped spanking her, and he was pleased with the dull red glow visible on Monroe's buttcheeks even in the dim light of the gambling den. With one hand, Frank cupped her mound. He pressed his middle finger firmly to her clit, not circling or stimulating, just impressing his presence upon her in the most intimate way he could, short of penetration. She stiffened, and Frank thought he might have heard a faint sound somewhere between a whimper and a moan.

"I suppose there's a lesson we can both learn from this experience," he mused, finger still pressed to her clit. "Anything can happen. To anyone.

"You can think about that," Frank said, his tone firming, "while you learn your other, more personal lessons: obedience and humility. Now get down on your knees, and suck my dick."

Quietly, the naked doctor fell to her knees. She shuffled around to face Frank's crotch, located and lowered his zipper, and fished his painfully erect cock out through his briefs, the tip already glistening with precum. She looked up, meeting his unyielding eyes one more time. Then she opened her mouth, exposed her tongue, and slid Frank's shaft into her waiting maw.

Apparently, Monroe's professionalism extended to fellatio. She may not have been enthusiastic, but she was methodical, working her mouth up and down the shaft in steady rhythm, tongue massaging the underside, one hand pumping the base while the other stroked his balls. Even as her swinging tits threatened to throw her off-balance, she maintained a surprising amount of poise, at least for a butt naked woman in a crowded room, on her knees with a dick in her mouth. Her posture seemed to say, "I may not control my circumstances, but I can control myself." She also probably figured her ordeal would end sooner, at least the public part, the sooner she could successfully suck Frank off.

Frank looked forward to disabusing her of both of those ideas. But first, he needed to set the scene a little better, as well as fix a few flaws in the previous power dynamic.

He wrapped one hand in Allison's hair, behind her head, and forced her head as far down his shaft as it would go. She almost reached the base before he felt her gag and resist. Then he turned to face the rest of the room, including the other past tournament participants, forcing the doctor to shuffle awkwardly around him on her knees as she struggled for air. Once they finished turning, he let her catch her breath. Then he pushed hard enough on the back of her head to indicate that she should keep sucking, and muffled slurping sounds filled the room again.

"Girls," Frank called, beckoning Charlotte and Colleen forward. They came, black- and purple-clad figures striding side by side. Charlotte smiled, wide and devilish, and even Colleen smirked faintly. They stopped on either side of the naked, kneeling, slurping doctor.

Frank pulled Charlotte in first and stage whispered in her ear, "Make the doctor's life a little more difficult, would you? Have fun with it."

Charlotte's eyes glittered mischievously. "Yes, sir," she murmured back.

Then she spun on her heel and spanked the doctor's bare ass. Hard. Monroe squealed around the cock still impaling her face.

"You call that sucking cock?" Charlotte asked loudly. "I don't see nearly enough slobber or hear nearly enough gagging. If you can still breathe properly, you're not doing it right. Here, let me help, if you're too stupid to figure it out for yourself."

Charlotte positioned herself behind Allison and started forcing her down Frank's shaft, longer and deeper than the doctor clearly preferred. She gagged more frequently, gasping audibly when she was allowed up for air. Tears sprouted from the corners of her eyes, trickling down her face and mixing with the excess drool spilling from Allison's overworked mouth, causing her immaculately-applied makeup to run. Even when Charlotte gave Monroe a breather, she maintained a steady rhythm of ass slaps and verbal jabs.

"Is that all you can take?" she mocked, forcing Allison's head back down onto Frank's shaft. "You'd better get used to it. I have a hunch you're gonna be sucking a lot of dick over the next few days. In fact, you'd better hope for it. The more time that cock spends in your dumb loud mouth, the less you'll find your other holes stuffed full. And I suspect those other holes will be pretty sore before Frank's done with you. Deeper, you dumb slut!"

Strictly speaking, having his cock repeatedly rammed into the back of Monroe's throat wasn't as physically pleasurable as when she had maintained her own pace, but seeing the doctor put in her place more than made up for it. Besides, Frank had other tasks to which to attend before he could really cut loose.

"Colleen, could you see to the new men under my command?" Frank asked his other vixen, indicating the gimps across the floor. "They look like they could use a little breathing room. No sex yet, unless you're feeling peckish yourself, but make sure they're ready to go."

"As you wish," Colleen answered, still with her slight smirk. She crossed the floor and busied herself helping the other men extract themselves from their leather getups. The men stripped with visible relief and eagerness. Although Colleen didn't strip down or suck them off herself, Frank noticed her hands coaxing their cocks to life with more enthusiasm than was strictly necessary.

"Claire," Frank called to the erstwhile dominatrix, who was watching Colleen work with a dissatisfied grimace. "Front and center."

She apparently knew better than to disobey. She crossed the floor and stood behind the doctor, still gasping and slobbering on Frank's cock at Charlotte's behest.

"Your turn," Frank stated, projecting his voice over the sucking sounds. "Strip."

Claire still looked displeased, but she did it. With some squirming, she located the zipper in the back of her outfit, opened it, then peeled the outfit down and off her slender body.

Frank got his first good look at his final prize's body. In many ways, she resembled Allison: thirty-something with smaller breasts, C-cup, but the same healthy perkiness just starting to sag with age; not quite as curvy, but still plenty of ass to grab; smooth, hairless, lightly-tanned skin on every inch of her body, with the faint tanlines to suggest several hours spent in a bikini at the beach last season; nipples that were probably pink in brighter light, and small, tight pussy lips that would probably be considered "cute."

She glared at Frank, not disrespectful, but clearly displeased with this turn of events. Frank smiled back. Claire would have a hard time spoiling his mood with the doctor still slurping away in front of him. In fact, the blonde was going to improve the situation.

Frank took hold of Allison's hair again and removed her from his cock. She gasped for air, drool falling from her mouth and running down her breasts.

"Get up," he commanded. "Bend over the table. Reach back and spread your cheeks."

Charlotte stepped back, and the doctor did as instructed, trying to maintain some semblance of poise as she exposed herself to the room.

"Your prop, please," Frank said, holding his hand out for Claire's riding crop. She reluctantly placed the handle in his palm.

"Rim her," Frank ordered, nodding to Allison. "She's going to need it."

Claire looked at him disgustedly.

"Don't make me say it again." Frank warned, brandishing the riding crop.

Claire sighed, then approached Allison from behind. She bent at the waist and hesitantly brushed the exposed bunghole with her tongue, then recoiled and made a face.

Frank struck her on her own exposed ass with the riding crop, not full force, but definitely enough to sting. Claire flinched.

"Get used to it," Frank told her. "You're going to taste a lot more ass than that. If you want extra punishment too, I'll oblige you."

Claire glared, but turned back to Allison's asshole. She probed again, then reluctantly went to work with her tongue. The doctor let out a muffled moan.

"Good girl," Frank acknowledged.

"Here," he said, holding the riding crop out to Charlotte. "I think this suits you better. Make sure everyone's on their best behavior. Pay extra attention to Claire, here."

"As you wish, sir," Charlotte murmured. She took the crop and immediately swatted Claire across each cheek. Claire let out a muffled squeal from between Allison's asscheeks, but continued the rimjob.

Frank stripped from the waist up as he watched Claire work, relishing the blast of cool air against the sheen of sweat on the lean muscles of his now bare back and chest. His cock still protruded proudly through his fly at full mast, shining with saliva in the dim light. Whenever Claire's enthusiasm waned, or even when she just seemed to settle into a rhythm, Charlotte swatted her on the ass or thighs again.

When Claire didn't require her attention, Charlotte turned to Frank, hot fire in her eyes. She kissed him hungrily, moaning into him, her mouth clutching desperately at his lips as she stroked his exposed shaft.

They broke the kiss, and Frank took a second to compose himself and catch his breath.

It seemed like Monroe was just getting into her rimjob, so Frank figured it was time to move to the next phase.

Wordlessly, Frank approached the two naked women. He got Claire's attention with a firm smack on her bare ass, then grabbed a fistfull of her hair and removed her from Allison's asshole. Monroe groaned softly in disappointment.

Frank positioned Claire with her head resting on Allison's lower back, still bent at the waist with her ass out at a right angle to Allison's.

Frank stepped up behind Allison, placed his cockhead against her glistening anus, and pushed.

Instantly, Monroe's head snapped up, her back arching in a desperate attempt to put some distance between her vulnerable anus and its invader. She cried out wordlessly in protest, but Frank didn't relent, and half the helmet slipped past her tightly-clenched ring.

"Don't fight it." Frank instructed. "Relax; push out, and let me in."

"I... I can't." Monroe protested hoarsely.

"Too bad." Frank responded. He didn't shove his cock all the way up her ass in one thrust, but he kept pushing. No matter how hard Allison clenched her cheeks, or how much she whined, he slipped in millimeter by millimeter until her sphincter slipped past the widest part of the helmet to grip the top of the shaft.

"That's the widest part," Frank announced, "but we've still got the whole shaft. Still want to make this more difficult on yourself, or do you want to demonstrate some self control?"

Allison mewled in discomfort again, but she took a deep breath and let it out. As she did, Frank saw the muscles in the arch of her back relax, and he felt her grip on his cock loosen slightly, though she was still wrapped tightly around him.

"Good girl," Frank praised. "Now push out steadily, and I'll go slow."

She did, and he did, burying his cock inch by inch now, savoring the friction on his shaft. In seconds, he was balls deep in Allison's impossibly tight asshole.

"Good girl," Frank said again. "You did it. Now here comes the fun part."

Frank withdrew slowly, then plunged in again, watching Allison's butthole curl slightly in and out with his motion even as it still clutched at the invader with the occasional uncontrolled spasm. Allison groaned, but didn't object, and Frank managed at least half a dozen long, slow strokes before the next learning opportunity presented itself.

"Ugh," Allison grunted. "It's getting too dry."

Frank ignored her and bottomed out in her ass again.

"Hey, are you listening? I said it's getting too dry." Allison repeated, louder this time.

Frank shot Charlotte a meaningful look as he pulled out to the head. The redhead grinned and nodded, but waited.

"Argh, fuck, stop!" Allison cried as Frank plunged back in. "I said it's too dry, you bastard!"

"That's not how you address our master," Charlotte chided, lashing out with the riding crop. Allison flinched.

"If you want better treatment, you should try 'sir,' or better yet, 'master.' He likes when the girl he's sodomizing calls him by his proper title. I think he likes being reminded who's fucking the ass and whose ass is getting fucked. And what the master likes, you'll like. I guarantee it. Now, be a good girl and treat our master with some respect."

"No fucking way," Allison said through clenched teeth as Frank buried his cock again.

"Have it your way," Charlotte said, nodding to Frank.

Frank took the cue and upped the intensity, plundering Allison's ass in a steady rhythm and with more force than was probably necessary.

It didn't take long.

"Ow. Ow! Okay. Okay! I'm sorry! I'm sorry, master. Please, I'm sorry I was disrespectful. Please, I need more lube. I, uh, need more lube so my butthole can pleasure you properly. Please, sir, have mercy on me."

"Good girl," Charlotte gloated.

Frank pulled out, watching Allison's ass gape briefly before it winked closed again. He placed one hand firmly on the back of Claire's head, still resting on Allison's lower back, then plunged into her mouth.

Claire tried to pull away, but Frank held her in place, and from her awkward position she couldn't fight back. Even with her mouth full of cock, Frank could see the look of utter disgust that washed across her face.

Frank sawed in and out of her mouth, gently but undeniably fucking Claire's face.

"Use your tongue," Frank commanded. He felt her obey, and if he hadn't been ready for it, Frank might have shot his load down her throat right then and there. Despite the day's activities, he'd now enjoyed Allison's ass and mouth for long enough that he could easily unload at any time.

But he still had work to do.

Once Claire had him slicked up again, he pulled out of her mouth and slid slowly back into Allison's ass. Saliva wasn't exactly the best lube, but Frank enjoyed the resistance, and it at least helped enough that Allison gritted her teeth and didn't object.

Frank alternated between Allison's ass and Claire's mouth several times, always waiting for Allison to swallow her pride and ask politely for more lube before he relented. Whenever she did, Claire grimaced, but she settled into her role as lube-slut without complaint.

Frank beckoned Charlotte to join him, and his first conquest obliged. She locked lips with him again, this time probing his mouth with her tongue. Her hands roamed over his back, chest, and shoulders, exploring his muscles appreciatively as he plundered the ass and mouth of his two newest prizes.

After he finished his fourth or fifth cleaning session in Claire's mouth, he grabbed Allison by both hips and pulled her a foot or so towards him, shuffling back to leave space between her legs and the table on which she still rested.

"Make her cum," Frank commanded Claire as he placed the head of his cock against Allison's rosebud and slipped inside again. After so many entries, her asshole wasn't the nigh-impenetrable barricade it had once been, but her warm bowels still hugged him snuggly even as they allowed his shaft to slide smoothly in and out.

Claire glared at him, but obeyed. She slid off Allison's back and under the table, arching her back and craning her neck to press her mouth to the doctor's slit.

Allison stiffened, then moaned involuntarily. With what little leverage she should muster, she pressed her hips urgently into Claire's face and her flickering tongue, even as Frank held tight to her hips and continued plundering her ass in long, steady strokes.

Claire reached up and grabbed one of Allison's asscheeks in each hand, using the leverage to pull herself deeper into Allison's folds, licking with a frantic desperation that let Frank know she just wanted the ordeal to end.

Not that Frank was finished with them yet.

But whatever Claire's motivations, her efforts seemed to work on Allison, who in addition to the extreme sexual stimulation, seemed more and more to succumb to a complete breakdown of her standards and self control. She ground herself furiously on the blonde beneath her, which translated to a pleasant twerking motion on Frank's impaled cock, even as her anus began to twitch and spasm around his shaft.

Frank bent, his cock still lodged deep in Allison's ass, to whisper in her ear.

"Do you want to cum? Are you going to orgasm in front of all these people? You'd better ask for permission. You better not cum without my approval, or I promise you'll spend the rest of the week regretting your decision while wishing I'd let you come again."

"Fuck you," Allison grunted in reply.

Frank tsked, then straightened. As he slowly plowed Allison's ass, he got a grip on Claire's neck and held her at bay, just far enough that she could barely reach Allison with her tongue, but not provide the deeper stimulation the doctor needed.

"Ugh, no!" Allison moaned.

"You lost. Accept it." Frank instructed as he fucked her. "Be a good girl for me, and I promise you'll be much happier for it. I know you're stubborn, but you know it's the right decision. It's only logical.

Frank managed another half dozen thrusts, all the while keeping Allison from getting too close to Claire's tongue, before he felt her sag in defeat, and she responded.

"Fine," she sighed. "You win."

"What was that?" Frank asked mockingly. "I couldn't quite hear you."

"I said, 'Fine, you win!'" Allison all but shouted. "You win. You beat me. Now can I fucking cum?"

Frank didn't respond. He just kept thrusting. He might have let Claire get a little closer with her tongue.

"God damnit. Can I please fucking cum?" Allison asked again, desperation in her voice.

Three more thrusts.

"Please, sir! Master! I need to come. I'll be a good girl. Please let your good girl come while you fuck her ass!" Allison screamed.

Frank let go of Claire's neck and Allison's hips. Claire's mouth latched onto Allison's mound like a magnet, and the doctor's entire body arched like she'd been struck by lightning.

"Fuck!" she screamed, and her anus clenched, choking the life from Frank's cock as she climaxed.

"Fuck," Frank echoed more quietly. Suddenly, Charlotte's mouth was on his again, her lips riding his as he reached his own peak. His balls tightened, squeezing semen past Allison's impossibly tight ring as he ejaculated deep into Allison's bowels, spurt after spurt filling and coating her insides.

When Charlotte released him, Frank gasped for breath, mimicking the sweaty, disheveled brunette on the table in front of him. He removed himself once again from Allison's now well-abused asshole, gripped Claire behind the head, and fed his deflating member back into her warm, soothing mouth. Claire tensed, but complied, soothing Frank's sensitive shaft with her slowly swirling tongue.

When Frank was satisfied, he pulled out of Claire's mouth and nudged both naked women to their feet.

"Switch," he ordered.

Both new girls glanced at him in disbelief, then at each other, but they didn't argue. With a little bit of awkward shuffling between naked bodies, they did as they were told. Claire ended up tits down on the table, ass up and puckered anus exposed to Frank in offering. Allison bent over the table, legs visibly trembling, and laid her head on Claire's rear end, looking at Frank with wide eyes.

"Good." Frank commented. He quickly stepped out of his shoes, then peeled off his now sweaty slacks, briefs, and socks. He stepped up to the new arrangement of nude women and placed the tip of his cock against Allison's pursed lips. After a momentary look of disgust, they parted and welcomed him back into her mouth.

As Allison slowly sucked him back to life, Frank could tell from his member's sensitivity that the day had taken its toll. He was almost out of steam, but he had one more hole to plunder, and he wasn't going to come this far without taking his due.