The Bet

He heard the door first, slowly creaking open. The tentative footfalls making their way softly down the hall. Finally, she stepped into the den's warm, yellow light.

Jared let out a quiet chuckle... "Perfect."

Matt, on the other hand, could only think of one word as he looked his beautiful wife over from head to toe: SLUT...

A couple months earlier...

Matt and Jared had worked together for three years. Matt wouldn't call them great friends. Jared was actually kind of an ass: loud, brash, a frat boy still at 30. And Matt suspected Jared had a thing for Jenna. But beggars couldn't be choosers and ever since taking this job in Orlando, Jared was the only decent acquaintance Matt had made. And Jenna thought he was alright most of the time.

Matt and Jenna had relocated to Orlando three years earlier. Matt's job at the law firm was an opportunity they couldn't refuse. A radiologist, the job opportunities for Jenna were usually good and she had graciously insisted Matt take the job. Jenna had made a few friends at work, but nothing amazing. Matt's work hours had been long as he established himself in the area and at the firm. Consequently, Matt and Jenna hadn't had much time for one another, let alone for building a strong friend community. So, when Jared invited himself over, Matt often conceded and Jenna was usually game.

Jenna loved March Madness. She followed the stats, cheered on her teams, and was always vocal - she argued every call. Jared was the same and most often came over to watch a game. Jenna and Jared were both competitive and hated to lose. What's more, both liked a friendly bet here and there and, lately, they'd made more than a few. At best, Matt was a fair weather fan; he'd watch the game but was just as likely to read a book.

Frankly, Matt found it all a bit annoying, especially the bets. Usually it was over something benign like who'd have to chug their beer, but sometimes it was a few bucks on the line instead. For some reason, though, this season had taken a different turn. They'd upped the ante. Like when Jenna had taken $500 off of Jared on the Sweet Sixteen game the previous weekend.

But lately it wasn't just cash. Jared had turned up the dial in a different way. After losing the weekend prior, Jenna had spent a good hour washing Jared's car; but part of the forfeit was she had to do it in a bikini...while Jared watched from his lawn chair. That one had really ripped Matt, so he'd insisted that he watch as well. To be honest, he'd enjoyed the show, just not sharing it.

To say Jenna was easy on the eyes was putting it mildly. She was smoking hot: 28 years old, first generation Brazilian, 5'6" tall, a toned 130lbs with perfect, caramel skin and raven hair past her shoulders. She had round, full C cups up top and a pert, curvy ass below. But that day, carwash day... Matt remembered it vividly.

He and Jared had posted up in lawn chairs, in front of the garage. Jared's Porsche 911 waiting to be served. Jenna had sauntered out of Jared's house grinning ear to ear. A vision of sex. Platform sandals - the high wedge kind with a single strap around her ankles; they accentuated her toned calves and sleek legs. She'd chosen the micro string bikini from their trip to Bermuda. It was white, with a navy, sailor stripe. The tiny triangles of fabric stretched tight over her full breasts and barely concealed her milk chocolate areolas. She wore the low rise thong just as Matt liked - it just covered her mound, a tuft of her groomed landing strip peeked out the top. It had a seam right down the middle that defined her plump camel toe. The string ran back between her legs to reappear taught between her ass cheeks. She filled the suit out well and she knew it.

Jenna liked to tease and both Matt and Jared had enjoyed the display. As the car got wet and soapy, Jenna did too; as she played with the hose and rinsed her sponge, the bikini's fabric got more and more transparent. At one point, she bent over at the waist to fill her bucket and reached back with both hands to spread her cheeks, that tiny thong hiding her crinkled hole in no meaningful way. By the time the car was squeaky clean, pretty much everything was visible and the men's thoughts were absolutely filthy. It had been like a live-action wet dream.

Just now Matt was staring at Jenna's French-tipped toes. Her sexy feet bounced last circles in the air as she dangled her legs over the arm of the lounger. She smiled and wiggled her toes for him. He adjusted himself in his shorts. Today she was wearing her tight Lululemons in black, the high waisted ones. She always pulled them tight up the crack of her ass. Up top a gray, crop-top, hooded sweatshirt that ended somewhere just below her breasts. Matt hadn't noted when exactly but the way Jenna's nipples seemed to be poking, he was pretty sure she'd joined the no-bra club some time ago. Matt was also pretty sure Jared had taken his share of looks already.

They'd all been hanging out for a few hours, snacking, drinking, and watching the day's Final Four game. Jared and Matt were each 4-5 beers in, Jenna more like two. She was a light weight though and she looked pretty relaxed.

"Villanova's got this in the bag, chica." Jared said, glancing at Jenna as he sank back into the cushions.

"No way Kansas goes down, loser," Jenna replied, giving Jason the bird and kicking her feet playfully.

Jared fixed his eyes on hers with a smile. "Maybe we should bet on it." Matt groaned and shook his head.

Jenna, of course, laughed and shot back, "You're on! Though, after I took your $500 last time, you sure you want to go again?"

"Oh, I don't know. I don't care about money. But that carwash, that I enjoyed. I'd love to kick that up a notch... But I don't think you could handle much more yourself," Jared crooned.

"Please, I've got so much more! But...you'll never get to see it, jerk." Jenna prodded. "Besides...I'm not gonna lose. What's the forfeit?"

"Alright...well you said it already. How 'bout this: Kansas wins, you bag $1000; but if Kansas goes down, you do too."

A silence fell on the room. Jared sat, watching the action, casually munching some chips, as though he'd made the most normal suggestion.

"Excuse me?" Matt and Jenna said in unison.

Jared looked Jenna up and down boldly and smiled. "Oh come on...just a little fun. Your team goes down, you do too: you suck my cock."

He grabbed the rather large lump in his shorts. Jenna's eyebrows rose almost to her hairline. Matt began to wave his hand as though he could wave this all away like smoke.

"Don't worry, hubby can watch," he laughed. Jared extended his hand, waiting for agreement.

"Forget it. Your pencil dick couldn't handle it anyway, minute-man," Jenna spat.

Her breasts bounced as she swung her feet down to the floor and sat forward in her chair to grab her beer. She leaned back and swigged the end of the can down, tilting her head back and stretching her torso. Her sweatshirt rose scandalously high...

"Afraid of losing?...Or is it...maybe you're afraid you'll like it... Or hubby will..." Jared was still holding his hand out to Jenna, wager pending.

"Okay, guys, that's enough..." Matt said with a sigh.

But Jenna cut him off. Matt could see the fire in her eyes. "I'm not afraid...you're on!" She leaned forward and slipped her small hand into his. They shook.

"Jenna!" Matt shouted.

"Oh it's fine, baby... Kansas is not going down and I'm not either," she said with a smug smile.

She sank back into the chair and slid her ass forward. She pulled her knees up to rest her feet just on the edge of the cushion, heels to ass cheeks. A perfect view: the inverted heart of her ass cheeks, the seam of her leggings tight down the middle of her plump pussy lips, all on display. Matt was sure she knew it too, and he'd begun to think she wasn't wearing any panties...

Jared hungrily eyed that sweet spot between Jenna's legs, the shadow of her intimate curves. He imagined her soft hair and warm mouth down around his cock. He started to get hard in his board shorts. Jenna noticed the shifting bulge and tried to play it casual. But she was nervous and...wet. She glanced over at Matt. He adjusted his shorts too, but it wasn't excitement Jenna saw on his face.

Finally, in the fourth quarter, Kansas took it away and it wasn't really close. Jenna did her best to rub it in. When the buzzer sounded, she jumped up into a victory dance on the lounger, arms over her head, hips swaying side to side. Definitely no bra - Matt thought. Jenna looked down toward Jared and extended her hand, laughing.

"Pay up, loser...Kansas didn't go down and it looks like I won't be either."

"No, you're right, you're right... but you stay right up there, the view's great from where I'm sitting," Jared said, beginning to pull out his wallet.

Jenna dropped her arms and dismounted the chair, frowning but still holding out her hand. Jared laughed and smugly counted out 10 Benjamins onto the coffee table.

"Like I said, I don't care about money. And I'll live to fight another day." Jared smiled and packed up to leave.

"Yeah, okay buddy. That's more than enough," said Matt.

As Jared walked out to his car, he called back to Jenna, "Let's go bigger next time!"

"In your dreams, pencil dick!" Jenna shouted after him.

But in her head she was already thinking big things for the grand she had in hand. Even bigger? And the bulge she'd seen in Jared's shorts meant "pencil dick" wasn't quite right. She was staring out the door after Jared when Matt broke in...

"I hope you enjoy your winnings. I'm sure Jared would have..." Matt shut the door, turned and walked quietly into the kitchen.

He set to the dishes without another word. Jenna sank back into the lounger, counting and recounting the Benjamins in silence.

Matt smoldered away all night, until they got into the bedroom... When Jenna went to put her winnings away, Matt quietly followed her in. He found her bending over her nightstand. Looking at the smooth curves of her ass and that camel toe bulge, something took over in him. Jenna suddenly felt a hand on her back, another grabbed her wrist and pinned her arm behind her back. Matt forced her face down into the mattress and, with two hands, tore the seam of her 'Lemons wide open. No panties...

"Of course...you absolute slut," he muttered.

Jenna gasped as her leggings ripped. "What the fuck are you doing!"

Matt just grunted and spread her ass cheeks. Jenna felt the cool air on her wet folds. She felt Matt slide two fingers up and down her sopping wet gash and then deep into her pussy, forceful and rough. She heard him working at his belt, shoving his pants one-handed below his waist. She felt his hard dick bounce against her thigh. Jenna huffed and moaned into the mattress at his probing fingers. She gasped in a ragged breath as he withdrew them suddenly. Then felt the sting as he smacked his wet hand onto her ass... Not just once, but over and over, loud, full hand smacks. She cried out, but he didn't stop until her cheeks were hot and red and there were tears in her eyes.

And then...Matt dragged the leggings off in one pull and tossed her over onto her back like a rag doll. Sliding between her legs, he plunged into her in deep and close missionary thrusting, her legs instinctively wrapping over his clenching glutes. Her eyes rolled back in her head from the relentless thrusting. After a few minutes, Matt hooked his elbows under her knees and shoved her head first over the far edge of the bed. Jenna's head and shoulders rested onto the floor, her ass in the air against the side of the mattress. Matt straddled her ass, grabbed the back of each thigh and began to piston his cock down into her wet cunt - in and out, a rough pile-driver. She was folded in half like a pretzel, her legs thrown back, cute feet bouncing around her panting O-face. After a few minutes he pulled out and she flopped over to crawl back up the bed, face down ass up. She expected his thick cock, but moaned into the sheets as his warm tongue rolled up and down her wet folds and then began to swirl around her asshole. She groaned when he buried his thumb deep inside. It was too much.

Jenna moaned out, "Please...oh fuck...plea...stick it in my ass. Put your dick in my ass!"

Matt grabbed the lube from the nightstand, squirted a bunch all over his cock and, while shucking away with his right hand, he worked a gob of lube into her hole with his thumb. Jenna's hand snaked back, making small circles with her fingertips over her clit. Matt grabbed a fistful of her raven hair, pulled her up onto all fours and slowly squeezed his cock into her ass. Jenna huffed out a long wheeze, pushing her ass back into his dick until her glutes pressed into his pelvis. She rubbed her clit faster. Her pussy was leaking everywhere. Then Matt began a vicious, doggy-style pounding, his thick cock punching deep inside, his balls slapping her swollen lips and clit so that Jenna couldn't even catch her breath. Finally, she reached another hoarse, screaming orgasm. Matt spurted his cum deep in her ass.

When it was over and they were both panting and covered in sweat, Jenna rolled over and began to trace up and down Matt's flaccid dick and warm balls with her soft fingertips.

"Well, tiger...that was phenomenal. You haven't fucked me like that in a while. Where did that come from?" She paused... "Maybe I already know..." He said nothing, breathing heavy. "It turned you on, didn't it? It made you hot." Jenna whispered softly in his ear.

"What did?" said Matt.

"The thought of me on my knees. His hand in my hair. Me going down on his thick dick while you watched...admit it." she whispered in his ear.

"Okay, I was a little excited. You're hot..." He paused for two or three breaths and didn't speak the pornographic images in his head. "But it's not a good idea," Matt said instead. "Jared's a dick."

"I know... You're right. I know." Jenna kissed his shoulder softly. "I figured the chance they'd lose was real low. I just went for it. You know how competitive I can be. I'm sorry, baby," Jenna said.

In the darkness Matt whispered, "Would you have done it?" Jenna breathed out softly. "You would have, wouldn't you?" he grumbled. "Admit it yourself...it got you wet thinking of his dick - this whole night."

Jenna didn't answer right away. "Well, he paid up didn't he? I suppose I would have had to do it. I didn't really think it through, babe. I just get excited over those games. I'm sorry." Jenna pouted, running her soft hand over his chest and kissing his ear.

He was quiet for a few moments, then, "Let's just forget about it," said Matt.

But, in truth, Jenna couldn't forget. Matt fell quickly asleep, but he was right: it did make her wet, even now. She thought about it all night long.

Jared didn't forget either...

Two days later, when Jared showed up for the championship game, he brought along a few six packs and a burning desire to win. Jenna brought her game too. She'd decided to play the tease: her college cheer uniform - sleeveless red and black top that covered her up pretty well, though left her belly bare; the skirt, pleated red, black, and white that just barely came below her ass; white cheer sneakers on her feet. Matt had quietly watched her dress just before Jared arrived. He knew there weren't bloomers under that skirt, just a fishnet micro thong in white. It rode low and tight and hid almost nothing. Matt grew more and more wary of where this day would go.

As they sat through the first half, Matt and Jared took the couch, Jenna the lounger again. Jared was rather obviously tracing his eyes up those perfect legs - her caramel calves and toned thighs - to where the skirt lay dangerously high. Jenna watched his eyes out the corner of hers, slowly uncrossing and recrossing her legs, giving little glimpses of where those thighs stretched. She tried to catch a glimpse of Jared's shorts too.

Finally, Jared cut the tension. "Well, you wanna rematch?"

"Eager to give me more of your hard earned cash, huh?" Jenna laughed. "What are you offering up this time?"

Matt raised his hands in a big WTF motion.

"For fuck's sake, you two!"

"No, no...let me finish. I'm serious. Let's not fuck around. This is the championship. I say we go big..." Jared replied.

"Okay...soooooooo?" Jenna raised her eyebrows.

Jared took a slow breath. He glanced at Matt then looked Jenna in the eye. "Your team wins, I lay out $10,000."

"Holy shit, bro, no." Matt said.

Jenna looked excited. "Well, fuck! And for you, lemme guess, a week of bj's?" she laughed, fixing him with a disbelieving stare.

"Oh no, girl," Jared smiled. "For $10K? I said 'big'. No, if you lose, you're mine for a weekend - Friday night thru Sunday morning."

"And what does that mean exactly?" Matt interjected.

Jared's gaze didn't waver, locked eye to eye with Jenna. "Whatever I like. All. Weekend. Long. No holes barred." Jared said, extending his hand.

Matt glared from Jared to Jenna. He could see the fire in her eyes, that competitive burn...maybe something more. "Jenna, no. Don't you fucking dare..." he warned.

Jenna was quiet. She looked equal parts sick and excited. "$10 grand, baby..." she whispered. "I won't lose, baby. We're a shoe-in to win and we're already ahead..."

She said nothing for a full minute. She looked back at Jared. Then to Matt. She was sure she could see the outline of Matt's dick growing in his shorts. Matt, for his part, thought she was probably right, but he knew it wasn't worth it.

Suddenly Jenna stood up and slipped her hand into Jared's. "Game on," she said.

And it was on. And what a game it was. The tension was thick. Jenna and Jared shouting for the win, each arguing the calls, prodding the other. In the moments between plays, Jenna turned up the tease. In the kitchen, she stretched on her tip-toes for something high up till her skirt rose, just exposing her firm, bare cheeks. She sat cross legged in the lounger, the hem of her skirt just revealing her fishnet covered mound as she pretended to update her Insta feed. And, for the grand finale, she dropped her napkin on her way into the kitchen and bent over at the waist to pick it up... She looked back with a wink as the hem of her skirt rose to give Matt and Jared a view of the fishnet tight over her pussy and the string running between her cheeks. But it was the circular indent and the twinkle in her plump ass that caused both men to sharply inhale: her pink, gem, princess butt plug she'd bought six months ago. She'd snuck away and pressed it into her ass sometime in the afternoon, Matt was sure of it.

Jared just grinned and focused on the game. "That's a nice preview of things to come," he said.

"A peek at what you'll never have," Jenna replied.

Matt sat quietly. The slut had fucking plugged her ass! She liked anal occasionally, Matt knew...but for fuck's sake... He was pretty sure he'd seen a wet spot on the leather lounger and maybe even a glisten in that fishnet when she'd bent over too. And Jared had been adjusting his shorts quite a bit. Of course, Matt had had to do the same. He was hard as a rock.

Near the end of the fourth, Jared's team pulled ahead. And as the final seconds ticked away, Jenna was shouting, "What the fuck! Fuck! No...damnit! Fuck!"

Matt's head fell into his hands with a groan. Jenna had been on the edge of her seat, and fell to her knees in disbelief.

Jared just smiled and laughed. "Fuck is right...that's what we're gonna do. Free-use weekend cum slut. But not yet, honey. Though that is good practice, you'll be on your knees soon enough."

The room got quiet. Jenna looked over to Matt but he was staring intently out the window. Jared stood up, adjusted the significant lump in his shorts, and said, "I think I know exactly where to take things. I'll send you some detailed instructions... I'm out of country for a bit on business, but I'll see you in a few weeks, baby. I'm looking forward to it." And then he left.