Winner Takes All: Round 02

Colleen sighed, then slid off the bench and onto her knees on the floor. Charlotte, on the other hand, smiled.

"I'd love too, sir."

Charlotte reached for Frank's slacks. Soon, his pants briefs were around his ankles. His cock already stood achingly hard in anticipation of activities to come.

"I'll get him ready for you," Charlotte said to Colleen. "While I'm at it, you can start by worshipping his balls."

With that, Charlotte engulfed him. The now familiar warm, wet walls of her mouth hugged and squeezed Frank's cock as he worked her way up and down his shaft in several long, loving strokes. Charlotte shifted to the side to allow Colleen to nuzzle her own way in between Frank's legs. Seconds later, Frank felt another mouth on his right nut.

Unlike Charlotte, whose mouth always seemed to gently press on his genitals, this mouth was softer, more relaxed. Where Charlotte's hugged, this tongue and set of lips simply rested on his balls, sharing their warmth. It wasn't any better or worse, just different.

"Mmm, yes!" Frank rasped. "Just like that."

Charlotte looked up, and somehow she managed to smile deviously even with a mouth still full of cock. Colleen just kept lapping at his balls, eyes closed. Frank took a moment to relish the scene unfolding in the back of this limo: Colleen, nursing at his nuts with her petite ass poking out from her too-short maid's outfit, and Charlotte still dressed and grinning devilishly around the shaft in her mouth,

Charlotte kept up a steady up-down rhythm for a few minutes, pressing Frank's cock further and further into her throat with downstroke. When she felt Frank start to twitch in time with her strokes, she pulled off.

"Your turn," Charlotte said to Colleen. She took hold of Colleen's long, flowing blonde hair. Using it as a handle, she pulled the blonde off Frank's balls and redirected her to his shaft. Frank saw Colleen resist the instant before her lips touched the tip. Then she relented and allowed Charlotte to slowly force her mouth down his shaft.

"Mmm, yes," Frank groaned. He leaned back and closed his eyes. He felt himself hit the back of Colleen's throat as her nose brushed the edge of his pubes. Charlotte held her there, face impaled on Frank's manhood, until she began to struggle for air. Frank could tell, because her throat started twitching in efforts to inhale. Only when Colleen's hands braced against Frank's knees and began to push did Charlotte finally let her up to breathe.

Seconds later, Charlotte pushed again, and Frank felt Colleen engulf his cock once more. The blonde let her redheaded counterpart control her by the hair, and Charlotte gleefully pumped her up and down Frank's shaft at a steady pace.

Suddenly, Frank heard a sharp smack and felt Colleen's throat spasm. "Mmph!" She squealed around the cock gagging her.

Frank opened his eyes to see Charlotte's free hand still hovering over Colleen's bare bottom. Charlotte caught his eye and winked. As Frank watched, she spanked Colleen again, which elicited another spasm and squeal.

"Good girl," Frank mouthed softly to Charlotte.

Frank glanced at the rear view mirror and noticed McCurdy's eyes staring back. Apparently, Frank had an audience for his first double-blowjob.

Oh well, Frank thought. If he wants to watch these two gorgeous girls sucking me off, I guess he gets to know exactly what he's missing.

Charlotte kept up the spanking even as she continued to work Colleen up and down by the hair. With each slap, Colleen twitched and grunted, sending tremors of pleasure down the shaft and into Frank's groin. When eventually Colleen stopped reacting, Charlotte finally let go of the blonde's long locks.

"Keep sucking." She ordered.

Colleen shot a glance at Charlotte over her shoulder, then sighed and obediently went back to work. She kept roughly the same pace, but under her own control the strokes were smoother, more tender and more loving.

Charlotte gave a satisfied nod, then turned her attention back to Colleen's ass. With both hands, she gently pulled Colleen's cheeks apart, then probed at the object nestled between.

"Mmph!" Colleen squealed again at the new sensation. She pulled her mouth off Frank's cock. The head glistened from the saliva coating it, and several strands of spit hung from Colleen's lips.

"Please," she panted. "Not there."

"Shut up," Charlotte retorted. She spanked Colleen again for good measure. "Get that cock back in your mouth."

Colleen did.

"That's it. Good girl." Charlotte cooed before she went back to toying with the plug.

"Frank's going to fuck your ass so good," she continued. "He fucked mine last night, you know. He was such a gentleman. He even let me suck his cock while I got myself ready. It hurt at first, but Frank took good care of my tight little butthole. It still hurt, but it hurt so good. I can't tell you how good it feels to cum hard while a man like this pumps your asshole full of his warm seed, but you'll find out soon enough."

At this, Colleen looked up at Frank, questioning, though her lips were still wrapped around his helmet.

"It's true." Frank confirmed. He pushed Colleen's head back down, and she continued sucking. "The question is, are you a going to be a good girl about it? Because I guarantee you, good girls get to enjoy themselves. Just look how much fun Charlotte's having. Bad girls, though. Bad girls get punished, and they still get fucked whether they like it or not.

"So tell me," Frank said as he pulled Colleen back off his cock. "Are you going to be a good little buttslut for me?"

Slowly, Colleen nodded. "Uh-huh," she said nervously.

"Good," Frank replied, "because I believe we're here. It's time for the main event."

Sure enough,the car had just turned off the main road onto a long driveway. While "mansion" or "estate" would be a stretch, the house at the end was large enough and nice enough to prove that McCurdy had paid his own entry into the tournament. Seconds later, they braked to a halt.

"Girls, you can leave your clothes in the car. You won't need them." Frank instructed. "I'm just going to have a few words with Joe up there."

Frank hoisted his slacks back up and clambered out of the cabin, then walked around to the driver window. He gave McCurdy his instructions, then returned to the passenger door, opened it, and offered his hand to the ladies inside.

Charlotte emerged first. As ordered, she left her dress behind. She still wore her dress heels and ruby earnings, but the flesh between them was delightfully bare.

"I hope you don't mind, sir. I took some liberties with your instructions." Charlotte said, clicking her heels for emphasis.

"Not at all." Frank replied, looking her up and down in the dim glow of light from the house. "I'd say that's quite a good look for you."

He couldn't be sure in the dim light, but Frank thought he saw Charlotte blush and squirm just a little self-consciously under his gaze.

Next came Colleen. Likely by Charlotte's suggestion, she had also elected to accessorize. The maid's outfit and was gone, but the heels, hairpiece, and collar remained.

Oh, and the white apron and thigh-highs.

For the first time, Frank gazed on Colleen in all her glory. He followed the white stockings up to her hips. While Colleen wasn't even as thick as Charlotte, was curves she did have stood out nicely in contrast with the toned muscles of her calves and legs. Her buttcheeks were petite, but pert, and gripped the plug tight between them. Muscles in her lower abdomen framed her crotch, though the apron still hid her snatch. Her abs also led up to her breasts, B-cup at biggest, which perched proudly on her slim torso, tiny nipples erect in the cool night air.

Frank gently took hold of Colleen by the shoulder, hands brushing aside the blonde locks that still fell freely to her mid-back. He pulled her close and kissed her, slow but firm. Her lips, still flush and wet from her oral activity, melted under his mouth.

Colleen moaned softly and arched her chest toward him. Frank took the opportunity to probe gently, and found her snatch already soaked.

"Looks like you're ready to get started." Frank commented.

He repeated the procedure with Charlotte, and found her similarly primed. Unlike Colleen, she kissed back forcefully, wrapping her arms around him and pulling his head closer.

Before they could get too far, Frank broke the kiss.

"Let's go inside, shall we?" He suggested. "Can't have you lovely ladies catching a cold."

Frank nudged both girls forward and took a moment to admire their asses, one full and juicy, the other toned and tight, swaying as they walked in the dim light. When they reached the front door, Frank used the key he'd taken from McCurdy, unlocked the door, and ushered his companions inside.

The front hall boasted a traditional central staircase. To the right, Frank saw a well-furnished den, and to the right he found the dining room. The kitchen, he reasoned, would probably be around the staircase at the back of the house.

Frank led the girls to the den. Matching brown italian leather three-seat sofas, complete with a central ottoman and side walnut side side tables, wrapped the near left corner. The couches faced a large, luxury flatscreen in the far right corner. On the far wall he saw a genuine fireplace, logs stacked both on the grate and to the side for refueling.

After a moment's consideration, Frank pushed the ottoman up to rest flush with the center of one sofa. He beckoned Colleen forward, then guided her firmly down on all fours on the ottoman. In that position, Frank finally got a good look at her vagina. The lips, much slimmer than Charlotte's puffier pussy, glistened with moisture. From this angle, Frank could just barely make out the skinny landing strip framing her otherwise bald mound.

The plug, on the other hand, protruded proudly from Colleen's puckered anus.

Frank motioned Charlotte forward as he unbuttoned his slacks again.

"I might have dried off a bit on the way in. Be a good girl and get me lubed up again, would you?" He suggested.

Charlotte smiled and dropped to her knees. As soon as Frank's not-quite-fully-erect cock reemerged, she leaned forward and engulfed him. Sloppy sucking sounds and soft but enthusiastic grunts and moans soon followed.

Frank tore his gaze from the crimson curls bobbing between his legs and turned his attention back to Colleen. As Charlotte sucked, Frank reached out and grabbed a handful of cheek with head hand. After kneading a few times, he let his hands drift inward. With his right thumb, he began massaging slow circles around Colleen's wet entrance, eliciting a needy groan. With the left, he then toyed with the plug. Colleen squeaked, and Frank felt her vaginal walls tighten.

"Shh," he soothed. "I'll take good care of you. You've been so good so far. I'll make sure you enjoy this almost as much as I do. Charlotte?"

"Mmm?" She responded, even though she didn't stop.

"I think you've earned some attention, and Colleen needs a distraction anyways. Get on up there."

Frank pointed to the couch in front of Colleen. Charlotte got the idea. She pressed Frank deep into her throat more more time, so deep she gagged. When she pulled off, Frank's cock came out rock hard and generously coated in saliva.

Charlotte wasted no further time clambering onto the sofa, legs spread wide in Colleen's face.

"You heard the man!" She exclaimed. She grabbed hold of Colleen's head and pulled her in. Frank saw Colleen freeze from shock, then slowly, uncertainly begin lapping at Charlotte's slit.

"Mmm. Fuck yes. More. More. More!" Charlotte ordered, grinding her hips into Colleen's face. "Lick me. Eat me. Pleasure that sweet pussy, bitch."

Frank chuckled, then positioned his steel-like rod at the entrance to Colleen's folds and pushed.

Even with all the foreplay, and even with Frank's cock covered in spit, Colleen was tight. Frank moaned as he felt her vaginal walls grip his shaft. As he slid in to the hilt, Colleen groaned too, though in her case the moan was muffled by Charlotte's snatch.

"Mmm, that's good." Charlotte said as the moan's vibrations rippled through her. "Fuck her, Frank. Fuck that bitch while she eats my pussy. I want to feel her groan over and over again."

Frank obliged.

He started slow, pumping his full length in and out in measured strokes. Over time he quickened, and soon his balls were slapping Colleen's clit with every thrust. The blonde quickly gave up on any form of oral finesse; she resorted to wiggling her tongue more or less randomly as Frank fucked her, letting Frank's thrusts move her head up and down Charlotte's snatch.

Charlotte didn't seem to mind. A second hand joined the first gripping Colleen by the hair, and Charlotte began grinding her groin even more forcefully up and down Colleen's face.

Frank felt his balls begin to boil, but he still had one more activity in mind. Reluctantly, he slowed his pace. Not that Charlotte slowed down in the slightest.

With his cock still sliding slowly in and out of the blonde woman's tight pussy, Frank began working at her buttplug in earnest. Colleen squealed again, apparently much to Charlotte's delight as she squealed in turn. Frank ignored them, gently but firmly pulling on the plug until the widest part popped free of Colleen's anus.

Frank took a moment to admire Colleen's puckered hole as it slowly contracted again. It gaped slightly from the plug's daylong invasion, but looked like it would be a tight fit nonetheless.

I love a challenge, Frank thought.

He reached down, retrieved some juice from Colleen's pussy lips, and slathered it as best he could on her rosebud. Then he finally pulled his cock free of her pussy, repositioned it, and like her pussy before, pushed.

Even with all the preparation, Colleen's ass was at least as tight as Charlotte's the night before. He took his time, letting Colleen's rectum adjust to each inch before feeding it another. Eventually he bottomed out, balls deep in the blonde bombshell's tight butthole.

"Don't you dare stop," Charlotte warned, breaking Frank's focus. He looked up to see Colleen frozen in place, eyes and teeth clenched, forcing herself to breathe.

Frank admired the scene. There was Charlotte, splayed out in front of him with the blonde's head in her lap, freckled D-cup breasts bouncing on her heaving chest. Colleen still had her face buried in Charlotte's crotch. Her white stockings and apron framed her ass perfectly, only improved by Frank's cock lodged deep in her asshole.

"Keep licking, cunt." Charlotte ordered. "Eat my pussy while Frank fucks that ass. I'm going to come while he fucks that tight little asshole, and you're going to keep licking when I do. Got it?"

"Mmm hmm," Colleen managed through clenched teeth.

"Good, then get to it." Charlotte commanded as she pulled Colleen back into her crotch.

At that, Frank resumed his own activities. He slowly, ever so slowly, pulled most of his shaft free of Colleen's anal vise. When just the head remained, he reversed, driving his dick back into the depths of her bowels. Colleen tried to recoil, but Charlotte just pulled her head right back down. Over and over Frank repeated the procedure, feeling her anus clench tightly around every inch. Over time, Colleen's asshole relaxed just enough to let him get a steady rhythm going. Frank couldn't go as fast as he wanted, but the sensation of Colleen's clenched butthole squeezing the cum from his cock more than compensated.

Sure enough, Frank felt that familiar feeling in his loins, and this time he didn't stop. The orgasm built slowly, each stroke pumping the pressure higher and higher until he couldn't have stopped had he wanted to.

"Yes, yes yes!" Frank roared as he pounded Colleen's ass, launching the first spurt into her bowels.

"Oh fuck! Yes! Fill that bitch's ass!" Charlotte screamed. She came seconds later, writhing in place on the couch. She released her hold on Colleen's hair and slumped sideways, eyes closed, hips still twitching with after tremors.

Frank came down with her. He pulled out for the last time, his now limp dick popping free of Colleen's anus with a squelch. He stumped around the Ottoman and collapsed onto the couch next to Charlotte.

Colleen, finally free of Charlotte's grip, rested her shoulders and right cheek on the now wet leather. Her ass, still dripping semen, stayed in the air. Colleen breathed heavily, clearly not yet satisfied herself. After a few seconds, her hand made it's way cautiously to her still drenched pussy. Within seconds she was whimpering desperately, her fingers flying furiously in a frantic attempt to reach an orgasm of her own.

Charlotte was still down for the count, but Frank took notice. He sat up, scooted in, and took hold of Colleen by the chin. Reluctantly, Colleen slowed long enough to prop herself up on her free hand. Frank lifted her chin and kissed her, gently, even as she panted.

"Cum for me." He whispered. He kissed her again, harder this time.

"Cum for me, Colleen." He murmured. "I want to feel you climax." He reached under and tweaked her nippled.

"Cum for me. I want to hear my good little buttslut scream." This time he reached over and spanked her still upraised ass.

"Cum for me!" He bellowed, shoving his finger up her ass two knuckles deep.

Finally, she did.

Frank watched, amused, as Colleen shivered and shook with her long-awaited orgasm.

"Ooohhhhhhh." She half cried, half moaned as the climax took her. As the sound trailed off, she slumped face down into the couch once again, ass still up.

"Told you," Charlotte gloated. Apparently, she regained consciousness sometime during Colleen's climax. She was still curled on her side, but her eyes were open, and she grinned smugly.

Suddenly, the doorbell rang. Charlotte bolted upright, then looked questioningly at Frank.

"Ah, I was wondering when our company would arrive," Frank answered. "Charlotte, be a dear and let them in, would you? Dressed as you are, of course."

Charlotte still looked unsure, but nodded. She hauled herself off the couch and, still wearing her heels, clacked over to the door.

"Clean this off for me, would you?" Frank asked, turning his attention to Colleen. He slid over to the middle seat, in front of Colleen's head, and looked at her expectantly.

Colleen's eyes shot daggers at him, but did as she was told. As she took him in her mouth, her scrunched nose provided the only clue that she could taste her own ass on Frank's cock.

In the hall, Charlotte open the door to a pair of enthusiastic wolf whistles. Charlotte turned her hips ever so slightly, probably a subconscious effort to shield her snatch, but otherwise stood her ground.

"Umm, would you like to come in?" she asked. "I believe Frank is expecting you?"

"Right on!" came the enthusiastic response. Charlotte stepped aside to allow two men, both clearly college boys around Frank's age, into the house. The first to enter stood about 5'10'' with short, dusty brown hair and a square jaw. The second topped out a few inches higher, with a rounder face, tanned skin, and dirty blonde hair down to his ears. Both wore burgundy polos, khaki shorts, and loafers. For a few seconds they just stared at Charlotte's naked body, until the blonde one noticed Frank and Colleen in the next room.

"Dude!" he exclaimed. "Living the life, I see. Fucking awesome!"

Even as Colleen continued to suck Frank's cock, the blond walked over and gave Frank an enthusiastic high five.

"You know it, Cam. Max." Frank replied, acknowledging the shorter man as he followed. Charlotte and McCurdy, who'd come in after the boys, stood in the archway between rooms.