Winning Is Losing, Losing Is Winning

Kenny sat tied to his computer chair, hardly glaring at the older redhead standing before him. His face was void of all emotion beyond determination, and Bella's couldn't have look more amused by the fact. I don't like this, Bella looks way too relaxed, she thinks that this isn't even going to be a challenge. Kenny flicked his eyes over to Ellie who nervously watched him. Fuck, even Elle looks scared. No! Stop, thinking about this. I have to win no matter what happens, I have to protect Elle.

Bella cross her fingers and stretched out, cracking them, "So, before we begin, I want to make sure we are completely clear on the stakes. No confusion," Kenny wet his lips and gave one firm nod, "If you win our game, I keep your dirty little secret away from the rest of the world, but if I win, I'm free to do whatever I please with the information, and you become my new best friend,"

"****," Kenny bitterly corrected,

A devilish flash glossed over Bella's eyes, "Mhm, if you'd like. My ****," She corrected with a smile and pulled out her phone.

She's having too much fun with this already. The only chance I have is to try and throw her off her game somehow. Make her just a little nervous, crack that armor of smug confidence...Oh, I got it! Kenny cleared his throat. Bella peered up at him, "You know, hearing you say that, it doesn't sound very fair. I mean, if I win, I get to keep my secret, but if you win you expose it and I become your ****? That's not fair,"

Bella frowned and narrowed her eyes, "So?"

"I'm just saying, let's make it completely fair here. If I win, you keep my secret, and...you'll owe me a debt. To be repaid when and how I see fit," Kenny suggested with a smile,

"A debt? What, so you can have a few booty calls? So you can show off to your friends that you scored a college girl? Are you that pathetic?" Bella sneered back,

"I have nothing in particular in mind, but the debt would be anything I want, so that could be it...or it could be something way worse," Kenny grinned, trying to give Bella his best intimidating glare. The redhead stared back at him blankly. Haha, that got you didn't it? Threw you right off, suddenly losing to me sounds a little scary, huh?

"Okay," Bella plainly accepted without even a hint of worry. Ellie's eyes widened and the duo shared a quick surprised glance as Bella finished pulling up a timer on her phone, "Got any other complaints or can we get this started?"

"Uh...no, I'm...I'm good with the terms if you are?" Bella gave another nod, looking utterly apathetic,

"Good, the timer is set for five minutes," Bella tossed the phone to Ellie who made a fumbling catch, "The game is simple, you cum before time is up, and you lose," Kenny swallowed hard as Bella toward over him, "Ready to start? Because once we're going, there is no breaks or stopping until that time is up,"

Kenny took in a long slow breath, Bella Greene was one of the hottest, sexiest women that he'd ever met. Her breasts beat even Nikki in size, and her round perfect bubble butt was something to die for. As much as she might be pissing him off he couldn't reject his primal attraction to the woman, but five minutes? He could handle five minutes...right? Kenny exhaled, calming his body, "Give it your best shot," He challenged and Ellie started the timer.

Bella took a step back and reached down, grabbing the bottom of her dress and slowly pulling it up at a snail's pace. Kenny's cock twitched; inch by inch, Bella's long slender legs was revealed until a glimpse of red silk panties caught Kenny's eyes. The redhead tilted her head as she finished pulling the dress up to her waist, letting it remained bundled up around her stomach, "Do you like them?" Bella leaned forward as she eased her panties down her legs, letting her cleavage hang right in Kenny's face, "I love these ones,"

With a flick of her wrist, Bella tossed the silk underwear and they landed right on Kenny's face. The teen slightly trembled, the scent of Bella's sweet cunt was filling his nose, but he did his best to look unaffected. "Those are real silk," Bella hummed, letting Kenny get multiple full inhales, "Feel how soft they are?" Kenny softly grunted and Bella reached out, giving them a light tug. The red garments fell down and landed around Kenny's stiff cock, "Oh just look at you, so disappointing," Kenny kept his eyes narrowed as Bella looked him over, "You just got caught cheating with my brother's girlfriend, and look at you, still as hard as ever. No shame. No guilt. A single whiff of a woman and you've only got one thing on the mind,"

Bella knelt down in front of Kenny, "No self-control whatsoever," The redhead continued as she reached out and gave Kenny's cock a sharp flick with her finger. Kenny let out a sharp wince and Bella murmured out a laugh, "There is nothing more pathetic than a guy who can't control his urges. They're no better than a dog," Bella let out another giggle and abruptly grabbed Kenny's cock, "Maybe that's what you really are. Just a dog looking for a treat," Kenny failed to fight off a moan as he felt the silk panties fully wrap around his shaft and start to slide up and down under Bella's grip. "Oh please, don't tell me this is already getting to you, Ken. I've barely done anything!" Bella sighed and gave Kenny's cock another tight squeeze, this time pressing her thumb against his tip and swiveling it around, "So disappointing,"

Kenny gritted his teeth and gripped the arms of his office chair. Holy shit...she knows exactly what she's doing! Hold so tight, pressing right where it feels best, the silk panties...the talk...Christ, this isn't good. Bella pursed her lips, "Maybe I should increase the intensity a little?" Her hand began to pump Kenny's cock from base to tip in rapid, hard pumps. His mouth was agape and he let out a breathy exhale that only turned into a long groan as Bella's second hand gently started to cradle his balls, "That was easy. You're feeling so tense already. Is that really all it takes with you? And part of me thought five minutes was taking it easy on you,"

Kenny cocked his head, "Ellie, how long has it been?!"

"Um...one minute, ten seconds?" Ellie softly replied causing Kenny to let out a groaning cry of anguish.

No, no, no! I'm too close! I can't hold off for four more minutes like this, Bella is going to make me burst any second! I have to do something! I have to make her stop! I can't lose! Kenny screamed out as he locked his jaw and bit down hard. Bella froze and Ellie's eyes widened as they saw a sudden trickle of blood roll down Kenny's chin. The redhead stopped pumping and Kenny's body relaxed into huffing relief, "W-What? T-That all you got?" Kenny panted out, weakly looking up at Bella, refusing to back down.

Yet the redhead's surprise only lasted a few moments before her sly smile returned, "Bit your lip just to survive a little longer. That's impressive, very dumb, but I like it," Her tone sounded surprisingly genuine, "You'll be a fun a toy to have around the hotel, Ken," Bella moved behind Kenny and rolled him towards the bedside, "Okay, I'm sick of kneeling, I think I want to finish this sitting down," Bella slid down onto the bed, sitting only a few feet in front of Kenny now.

Kenny's eyes flicked down between the woman's legs, drinking in the sight of her perfect trim slit that had a neat landing strip of red hair just above it. Bella however, quickly caught onto his ogling and crossed one leg over the other, "Let's give this a try," Bella's leg began to slowly extend, "I'll give you a real chance, I won't use my hands anymore," A devilish smile grew across her lips, "Though I should admit, I think my feet are far more flexible and talented than my hands," Kenny gulped as he watched Bella's foot gracefully reach his cock, pinch hold her underwear and toss them away.

Without another word Bella's foot began to slide alongside the side of Kenny's cock, her toes wrapping around the side and pressing into him. Kenny shut his eyes and his body tensed again. The new sensation was something he was entirely unprepared for. Bella's soles were extremely soft, her toes were pressing in all the right places and when he felt her other foot complete the connection to properly jerk his length, he was already flying towards his edge again. "F-Fuck...oh Christ...Bella..."

"Hmm, what was that?" Bella cockily asked as she squeezed Kenny's cock between her feet and jerked him faster, "Surely my feet aren't feeling better than my hands are they? Are you that kind of sick little pervert?"

"N-No, I just...God..." Kenny growled feeling a familiar pressure churning in his balls and starting to build up his shaft,

"Aw, look at you, fighting so hard. You like them that much, huh? You just want to cum so bad," Bella pressed her toes around Kenny's tip, slathering his precum all-around before returning to her footjob, "It's okay, Ken, you can cum on my feet. I'll let you. Go on...cum,"

"Just stop, for two seconds!" Kenny finally exclaimed in a plead,

Bella leaned forward and looked Kenny dead in the eye, "No," Kenny let out shuddering gasps, and then finally a geyser of spunk exploded out of his tip. Bella stopped moving at once and merely sat back, enjoying the sight of victory as Kenny's cum painted her feet. "That's quite a lot, you must feel very relieved," The redhead reached down and scooped up a creamy rope on her finger and rubbed it between her thumb, "Very thick...about the only impressive thing you've done today," Kenny gasped for air and laid limp on his chair, "Ellie, the time?"

Ellie's whole body sunk down, "T-Three minutes... thirty-eight seconds..."

"And that's that," Bella hummed in a chipper tone, looking back to Kenny, "You lost,"