Winner Takes All: Round 01

Charlotte rolled her eyes, but grudgingly took Frank's hand and allowed him to help her out of the car. Now, for the first time, Charlotte noticed their surroundings: the parking lot for one of the off-campus dorms sandwiched between her school and Frank's. "You mean I'm walking all the way to your room like this?" she realized.

"Yes, dear." Frank gloated. "If you're lucky, nobody will notice at 3am on a Friday night. Best not to dawdle, though." Frank snaked his hand around Charlotte's waist to rest his palm on her right cheek and firmly nudged her forward. With no better option, Charlotte allowed him to lead her by the ass. Thankfully, Charlotte thought, Frank led her in through the side door, which at least meant no exposure to the security guard. The elevator took an eternity to arrive as they waited, Frank drumming his fingers where his hand rested on Charlotte ass. When finally the door opened, Charlotte darted inside and, after Frank followed, mashed the door close button repeatedly.

"Hold up, please!" A male voice came from down the hall. With a devious grin, Frank blocked the closing door with his free hand.

"Sure thing!" He called. "Get on in."

"Thanks," replied the voice's owner as he entered the elevator, female friend in tow. "Almost missed-." He trailed off mid-sentence upon noticing the beautiful naked woman sharing his elevator. His female friend, equally aghast, simply stared at Charlotte-open mouthed. Charlotte, for her part, hunched her shoulders and wished she could shrink into the floor.

"No problem," Frank replied nonchalantly. "I hate waiting for the elevator. Well, enjoy your evening!" The elevator arrived at Frank's floor, where he guided Charlotte by the ass out of the elevator and down the hallway as the doors closed on the gaping couple left behind them.

***

Schluck. Schluck. Schluck.

After Charlotte's protest to Frank's anal probe, Frank had pushed her head back onto his still-glistening cock and graciously, he thought, allowed her to continue blowing him from her kneeling position on the floor beside his bed. Every so often, he'd pull her off his shaft and direct her towards his balls. Charlotte, to her credit, gave no protest, but grudgingly lathered and swirled Frank's nuts with her tongue.

"Damn, Red." Frank finally commented after a half hour of enjoying the ginger's oral skills. "I could let you go all night. Lucky for you, I've been an endurance athlete for years, so I've got the stamina to let you suck to your sexy little heart's content."

"Hmpph," replied Charlotte indignantly around the shaft still filling her mouth.

"I know. I know." Frank continued. "We have another big day tomorrow, and we'll need our rest. I guess that means it's time for the main event."

Frank pulled Charlotte off his share and helped himself to another tongue bath for his balls before finally releasing Charlotte and allowing her a second to catch her breath.

"Stand up. Turn around, and ride me." Frank instructed. Still panting, Charlotte briefly considered talking back, but instead let out a small sigh and stood to perform as instructed.

"Good girl." Frank cooed. "Nice and slow. That's it." Slowly, tantalizingly, Charlotte lowered her pussy onto Frank's saliva-lubed shaft. Frank had deliberately avoided probing Charlotte's snatch and instructed her to do the same. Now he reaped his reward as the nubile redhead's unstretched cunt hugged his invading dick ever so snugly. Despite the lack of manual preparation, the nudity and humiliation and fellatio had apparently whetted Charlotte's appetite, and between her natural lubricant and the saliva still coating Frank's shaft she sheathed him snugly but smoothly.

"Excellent," encouraged Frank as she bottomed out. He flexed his pelvic muscles, causing his already full mast to straighten an extra millimeter. "Stay right there for just a second. I want to savor this."

"Pig," snapped Charlotte. She turned her head to look at Frank over her left shoulder, tossing her gorgeous flaming locks into a cascade down her back as she did, and fixed a defiant stare on Frank.

"On the contrary," he replied smugly. "You'll be doing all the squealing tonight. Especially when I stick you like a pig. Now ride"

Charlotte began to bounce, gradually increasing the pace as her pussy stretched to accommodate Frank's cock. "What do you mean?" She demanded. "You're already impaling me. What do you mean, 'when you stick me?'"

"Ah, even when fucking you're observant. I like that. What I meant was, you'll probably be the one squealing when I'm reaming your tight little ass."

"What? No! You can't!" Charlotte cried, even as she continued to slide up and down Frank's mast.

"Bullshit. You lost, you pay the price. Plenty of girls do anal, so don't even begin to think the "no permanent bodily harm" clause applies. Cooperate, and you might actually enjoy it. Don't, and my cock's still plundering that work of art you call an ass."

"Please don't. There must be some way." Charlotte had apparently decided that begging might succeed where defiance wouldn't.

"Hmm, I'll tell you what." Frank mused. Charlotte stopped bouncing and cast a hopeful glance back over the same left shoulder. Frank took just a moment to admire the sight of her: buck naked, plump pale ass hovering over his crotch with the tip of his cock still nestled between her labia, bottom lip of her mouth pouting ever so slightly, and eyes wide and hopeful.

"No, don't stop. Good girl." Chided Frank as Charlotte resumed. "If you make me cum in your pussy, I won't have any more for you before bed. You have until I get tired of this sweet snatch."

Charlotte's hope-filled eyes went wide for a moment before she redoubled her efforts. Now, rather than a simple up and down motion, Charlotte pulled out all the stops. First, she allowed body rolls to ripple down her back, ending at her hips in a twerking motion that Frank found both aesthetically and kinesthetically pleasing. She interrupted herself only to drop her hips and bottom out on his shaft, slowly rising and falling while flexing her pelvic floor to grip Frank's cock firmly but comfortably. It felt like a loving handjob, but with Charlotte's delightfully warm pussy instead of her hand. After three or four strokes, Charlotte would resume her regular twerking motion.

"Yes, baby," Charlotte moaned. "Give me that cum in my pussy. I need your cum in my pussy. Please cum in my warm tight snatch and let me clean you with my mouth."

Frank nearly lost it at "clean you," but managed to narrowly dodge the point of no return. Amazing, he thought, the effect of proper motivation.

Sensing that she'd nearly succeeded, Charlotte twerked even faster, but Frank had himself back under control. Frank allowed Charlotte to continue another 10 minutes, savoring the sight of this red-headed wet dream bouncing her hips frantically on his pole. Now that she was fucking in earnest, Charlotte felt waves of intense pleasure begin to pulse out from her pussy into her abdomen and down her legs, making it difficult to focus on the task at hand.

"Mm, fuck." She muttered as she paused her rhythm long enough to grind her hips in several circles. "Mm, fuck, I'm gonna cum. I'm gonna cum. I'm gonna-"

Charlotte's last word got lost in the indistinct guttural sound that next escaped her mouth. From his front row seat, Frank could feel Charlotte's pelvic and abdominal muscles clenching sporadically as her orgasm washed over her. Damn, but this chick's pussy was made to pleasure his cock.

"Right then," Frank announced. "Face down, ass up if you please."

"Nnooooo." Charlotte lamented, though she stopped bouncing and simply sank all the way down on Frank's well-worked pole, panting softly into the ensuing quiet. "You haven't even done anything to get my asshole ready for this thing."

"Hmm, I suppose you have a point. Fine, you may pleasure me with your mouth again while you get yourself ready."

With a sigh, Charlotte stood again, allowing Frank's cock to spring free with an audible squelch. With only the slightest hesitation, she dropped to her knees again in front of her soon-to-be anal invader. She leaned forward, breath still hot and panting on the dick in hand, before pausing to look around.

"Do you have any lube?" Charlotte asked.

"Not this time." Replied Frank. "Saliva only. I want you raw the first time. Guess you better make sure my cock and that asshole are good and wet."

Charlotte made puppy dog eyes for all of five seconds before she let out another sigh and began sucking on her fingers.

"Ah, ah, ah." Frank chided. "If I'm not being entertained, somebody is going to lose her prep privileges."

Charlotte removed her fingers from her mouth and promptly swallowed Frank's shaft. While she sucked, Charlotte tentatively probed her reluctant anus with wet fingers. Frank felt her tense as she slipped one finger inside. Despite her best efforts, Charlotte couldn't get more than a knuckle and a half inside the vice-like hole, and instead opted for slowly stroking half her finger in and out as she slurped.

All too soon, in Charlotte's opinion, Frank grabbed her red mane and pushed her down for one more deep stroke before yanking her off his cock. She had done a good job, Frank noticed, and his pole glistened with ample amounts of saliva.

"Face down, ass up, my dear. I won't ask again."

With one last timid look at Frank's proud wet member, Charlotte resigned herself to her fate. She obediently faced away from Frank and set her head on the floor, leaving her ass up in a position that, Frank thought, practically begged to be fucked.

"That's enough," Frank instructed, grasping the Charlotte's wrist attached to the finger still cautiously exploring her puckered hole and pinning it to her lower back. "You're as ready as you'll ever be. Relax, breathe, and focus on the good feelings. Who knows, you might even enjoy getting buttfucked."

Without further ado, Frank placed his swollen tip against the tiny inviting ring and pushed. What little resistance remained gave way quickly, and Frank half-watched half-felt his shaft slide into her hot, rubbery rear entrance.

"Ffuuuuuuuuuuuuuuuuuuuuuuuuucckk," both moaned simultaneously as sphincter slid along shaft and Charlotte's rectum stretched to accommodate Frank's throbbing cock. Soon enough, Frank bottomed out, and he paused only a second before pulling out to the ring around the helmet. His second stroke he made quicker than the first, the third quicker, building to a rhythm that soon had Charlotte grunting in sync with the sound of Frank's balls slapping her labia.

Unngh. Unngh. Unngh. Unngh. Unngh.

"Yes, yes, yes, yes, yes." Frank exclaimed, building to a near frantic pace. Frank could outlast the best of them, but more than an hour of this young bombshell's unrestricted attentions had him at his limit. As her own loins began to burn again, much to Charlotte's surprise, she sensed Frank begin to twitch and jerk from within her rectum, and added her own encouragement to his enthusiasm.

"Yes, baby, yes. Fuck this tight asshole. Make me your buttslut. You won me fair and square. You deserve to violate this anus as your reward. Take my tight virgin anal cherry as your prize!"

At "virgin," Frank came. He continued to piston into her upraised asshole as his cock convulsed, spewing shot after shot of backed-up semen into the flaming vixen's deflowered rectal cavity until the post-orgasm sensitivity overwhelmed him. As his hot seed flooded her with warmth from within, Charlotte climaxed again, knees shaking and rubbing the floor as she released another guttural moan.

He bottom out one last time, pushing Charlotte flat to the ground with his hips, before slowly, carefully, extracting his semi-erect pole from Charlotte's cum-lubed sphincter. With considerable effort, Frank pushed himself back to a sitting position on the edge of the bed, admiring the sweaty, semi-conscious, cum leaking nubile sprawled out in front of him. Her asshole, he noticed, though wider than when it arrived and with a new raw red tinge, was already contracting back to its original size. Her breathing gradually returned to normal, and she opened her eyes.

"Wow. I hope you enjoyed that half as much as I did." Frank said. Charlotte pursed her lips and didn't respond.

"I'm afraid I only have one bed, so we'll be sharing, unless you prefer the floor. Of course, I only have the one blanket, and I'm sure you understand room policy prohibits women from wearing clothes while visiting."

Once again, Charlotte said nothing, but she made eye contact with Frank and gave a slight nod.

"Splendid! Clean this up for me," Frank instructed nonchalantly, wiggling his still semi-erect penis at her, "and you can clean up yourself in the shower before bed."

With disgust evident on her face, Charlotte crawled forward and once again engulfed Frank in her mouth. After a allowing her a few deep, thorough strokes, Frank gently pulled her off his cock by her hair.

"Good girl. I think we'll have lots of fun together. Now be a dear and get yourself cleaned up for bed."

Charlotte stood from her sore needs and disappeared into the bathroom. The shower starting running soon after. As he wiped himself off and re-made the bed, Frank reveled in his as-of-yet good fortune and contemplated his next move. Charlotte would serve nicely, Frank decided, provided she was willing to assist him in his plans for the next round.

Frank busied himself tidying some of the mess they'd made while waiting for Charlotte to finish. Apparently, her exhaustion won out over obstinance, and after only fifteen minutes the water shut off and Charlotte emerged wrapped in Frank's towel. At the sight of Frank wagging his finger, Charlotte pouted but removed the towel and hung it back on its place inside the door. Frank lifted the blanket, motioned the nude now freshened redhead into bed, and followed her in.

"You are quite the prize." He whispered into her ear as he spooned her. "In the morning, remind me that I have a proposal for you that I think you'll find ... attractive."

With a soft, satisfied cock and contented smile on his face, Frank left Charlotte to ponder his last words and drifted off to sleep.

***

If readers like the story, stay tuned for round 2.