The Bet

This story is written by Vic and runnergirl

Dave slowly walked to the back of the court to pick up the tennis ball. The hot sun beat down on him as he felt the sweat dripping from his forehead into his eyes. His shirt was soaked and he swore he could smell the booze from last night as it came out of his pores with the sweat.

As he bent to pick up the ball he wondered why he had agreed to play at all today. Then with a smirk thought, damn bitch, she knew what she was doing when she offered to be the designated driver last night. He turned back towards the court and slowly walked to the service line. Blinking through his sweat covered eyes; he looked across at Diane getting ready to return his serve.

He and Diane had been dating for four months, and a large part of the attraction was her competitiveness and athletic ability.

Dave needed this serve to tie the game one set each. There was no way he wanted it going to a tie breaker, no way he wanted to lose, never mind two straight sets.

Taking a deep breath and putting every bit of his focus he could muster, he tossed the ball into the air and hit the serve with all he had. Before he could react, it was sent screaming back towards him. His eyes followed it as it raced just outside his reach to land just outside the back line.

Dave walked to the side of the court to get a drink and change ends. As he picked up his water bottle and let its cooling contents run down his throat and over his face, Diane joined him.

“You lucky shit, I thought that was in for sure, I’m not going to let you beat me today,” Diane said as she looked at Dave.

A smile came across her face as she thought about how much he must be suffering. They had partied hard last night and he had done the drinking for both of them.

“Smile all you want now sweetheart, there is no way you will beat me, this next set is mine,” Dave answered between gulps of water. “You haven’t beaten me yet and even hung over you won’t today.”

Dave looked at Diane and could see the wheels turning in her mind. His eyes slowly lowered from her big blue eyes and blond hair bordered face across her B cup firm tits with perky swollen nipples. His eyes continued their wonderful sightseeing trip down her firm stomach, along over the gently shaped hips, to finally rest on her gorgeous athletic legs he could never get enough of.

Diane leaned into him and gave him a kiss then whispered,” Today you’re mine baby, what to bet…next Friday night the loser goes over to the winner’s place and does whatever the winner wishes… you game?”

A large grin came across Dave’s face as he quickly told Diane, “I’ll leave the door open for you, let’s get on with this last set.”

The remainder of their game was a total blowout. Diane forced Dave’s weary body all over the court, purposefully causing him to run madly to each side, with the ball just out of reach every time. At her last serve, Diane bent wayyyy over with a mischievous look on her face, twirling her racket casually in her palms as Dave became mesmerized with the lovely tops of her breasts that were peeking out of her v neck shirt. Then, when she knew that he was distracted; she sent a rocket of a serve his direction, and all he could do was stare dumbfounded as it sailed right by him.

“FUCK!” Dave yelled in defeat and frustration, knowing that it would be her time to gloat and rub the loss in his face. And gloat she did; Diane bounced like a little girl all over the court and all Dave could do was stare as her tits jiggled in her sweat soaked shirt, the nipples hard and at attention, her lovely ass as her tennis skirt flew up with each jump, and her curvy calves as she twirled around with happiness.

“I’m sorry babe but you know what that means,” Diane reminded him as she walked over to his side of the court. “You are all mine next Friday night and there is absolutely NOTHING you can do about it!” With a gleam in her eyes she demanded, “I want you at my condo at 6, no questions asked, ok?”

Dave was still panting and sweating profusely as he nodded silently in agreement, wiping the streams of sweat from his forehead and the sides of his pounding temples. She was right, he HAD lost fair and square; now he had to suck it up and give her what she wanted. But, as Dave walked with his gleeful girlfriend to the changing rooms, what might she have in store for him? He wasn’t sure if this bet would work out in his favor or not, but either way he could hardly wait to find out!

That Monday morning Dave had to fly to Denver for a sales meeting and would be gone until Thursday evening. He sat on the plane relaxed, knowing he had all his projections and sales targets for next year ready to present. Dave had been with the company for six years and by the end of the fourth year was top salesman on the west coast and now was going to get an award for top in the country.

He laid his head back against the seat and had a smile come across his face as he thought about how happy Diane was when she beat him. I still can’t believe she won even if I was hung over, but damn that girl is not only hot but really competitive.

Dave also thought back to the early text he received from her that morning just saying, save some energy this week loser, you will need it xoxo. His mind wondered further about the bet, hell what did he have to worry about? She might make him cook, who knows maybe clean a bit, and then what…lick her pussy till she cums? That he does without losing a bet. Dave looked out the window and took a deep relaxing breath, thinking in his mind this gorgeous women he was falling for so deeply for couldn’t get him worried about a simple little bet.

However, nothing could be further from the truth! If Dave only knew what Diane was up to, he might be concerned, it not downright worried. This bet of theirs was actually planned by Diane for many weeks; she had schemed and fantasized about putting Dave in such a predicament so that he would become the powerless one, whereas she would hold all the cards. Dave, being much respected in his career, rarely had anyone ever challenge his authority. He was used to telling his subordinates how things needed to be successfully run and things ran smoothly that way. But, Dave also behaved like this when he was with Diane, usually calling the shots on where they would eat, how often they would see each other, etc. Also, he often dictated when, where and how they would make love.

Diane actually preferred the man in her life to take charge and thus respected Dave for his loving direction, but also yearned to shake things up a bit. She wanted to tease him a little and also show him that she could be boss for once. And she felt comfortable enough to use this opportunity to fulfill one of her intimate fantasies, one of which she had never uttered a word about. So, while Dave was away on his trip, Diane had plenty of time to work on all of the details as well as acquire anything needed to make her dream a reality.

Friday night could not come quick enough for either one of them. Dave was beyond curious as to what Diane had thought up, whereas Diane was nervously thrilled that the day had finally arrived. Diane took her time getting ready; she put on Dave’s favorite sundress (a short, light blue one which was slightly sheer) and cooked some delicious pasta Alfredo. Dave was still slightly tired from the trip but they had a nice, relaxing dinner and got caught up on everything that had happened while they were apart.

Dave thought, so far, so good, there’s nothing out of the ordinary here, and relaxed somewhat as they shared a slice of scrumptious chocolate cake. Yet, Diane’s moment to reveal her surprise had come and she excitedly brought the dirty dishes into the kitchen.

As she went to get changed, she said, “I’ll be right back hon. Why don’t you get a little more comfortable while I’m gone?”

Dave fell back onto the oversized sofa and placed his hands behind his head, took a deep breath and looked up at the ceiling. With a smug look on his face he thought, I think I will lose more bets, a beautiful dinner and now told to relax while I am sure Diane will come out dressed is a sexy outfit and then I’ll probably have to please her.

His mind wandered, thinking about Diane’s beautiful body and how he loved every inch of it; the image of her strong shapely legs leading up to that firm ass and sweet completely shaved pussy. How her inner lips just peeked out between her tight outer lips, begging to be gently opened and have its inner treasures licked and sucked. His thoughts proceeded up across her tight stomach to those beautiful small tits with the perkiest nipples he had ever seen. All this beauty topped off with that gorgeous face he never got tired of looking at.

Yes he thought, bring it on baby girl.

It seemed like a lifetime before Diane finally came out of her bedroom. But she was worth the wait; she was positively stunning in a light peach corset, matching satin bikini panties, and thigh high creamy stockings. The color was incredibly lovely against her light skin so that she was practically radiating with a rosy glow. Dave scanned up and down her tight body with appreciation. He was just about to tell her to come to him, but then he noticed that her hands were hidden behind her glorious ass.

With hesitation he asked, “Sooooo, what do you have there?”

Diane became downright giddy in her response as she brought her hands forwards to reveal her surprise.

“Here are the two items that will help me in showing you who is boss for the night.

And, for once, it ISN’T you!”

Dave almost fell off of the couch when he saw what she was holding! In one palm she cradled a double pronged, hot pink dildo, while the other held some sort of lube.

“Ummm,” was all Dave could mutter, staring transfixed as Diane sauntered over to him.

“Here, come with me,” she ordered, taking her treasures in her left hand and offering up her right hand to lead him into her bedroom. It was a glowing and comforting sight. Diane must have had a hundred tiny candles scattered around its perimeter and on her bed she had placed an oversized fleece blanket. The room smelled of lavender and was just the right temperature for love making.

“Please lay down on your back darling,” she told Dave, indicating with her wide eyes that he needed to sample the new blanket. So he did what he was told, reclining stiff as a corpse on Diane’s bed, his mind not quite comprehending what this all meant. Yet he knew full well that he couldn’t deny her.

She said encouragingly, “Relax babe, I’m not going to hurt you! Well..... maybe just a little.”

Diane came up next to him on the bed, allowing the dildo to drop next to his agitated hips. Dave let out a nervous snort whilst Diane removed his t shirt, shorts, and briefs, leaving only his socks and tennis shoes. Now it was her turn to admire her lover’s body: his athletic build, strong legs, and thick pole which was already reaching up for her touch.

Diane poured vast amounts of lube into her palms and then rubbed them together before starting an invigorating rubdown of her man. Starting at Dave’s ankles, Diane worked the warming liquid into his skin, listening to his body to find any tenseness. With one hand on the outside and one on the inside of his muscular legs, she rubbed the kinks out with her thumbs, exerting gentle pressure where needed. Next, she massaged his chest and stomach, loving Dave’s manly ridges and his raised pecs, intertwining her fingers within his strawberry blond chest hair.

Dave drowsily closed his eyes, sighing in bliss and practically melting into the soft bed. Diane’s long, gentle fingers were kneading, rubbing, and stroking his goose bumped skin as she leaned over her lover. As she was pleasuring, her tits began to spill out of the tight corset.

Dave was almost asleep when his crystal blue eyes shot open with surprise. His girl had found her way down to his ass, gliding her slick fingers with slow, circular movements around his shut hole.

“Ohhh crap, there she goes,” he thought, knowing that this was the point of no return.

Diane’s probing hands were now gliding within his ass crack and up to his balls, with round circles around each one before she traveled south again. Next, with two fingers she tickled his hole until it grew hot and tingly. When it finally gave way, she pressed them inside and Dave groaned with a mixture of excitement and dread.

Yet Diane didn’t give him much of a chance to decide whether he might enjoy this new act or not. Pulling off her panties she swiftly snatched the strap on, covered it with more glossy oil, shoved the larger dildo up her moist pussy, pulled the g string within her tush, and clicked the belt into place. Now all that was left between Dave and his girlfriend was 5 inches of slippery plastic.

In one decisive move, Diane had Dave’s legs raised up next to his heaving chest, with her pretend dick tapping like a door knocker at his little anal opening. Dave’s freckled face flushed instantly because she immediately began pushing her toy inside his body. To distract Dave from the agony, Diane clasped her fingers together as if she was praying, and made a soothing seal around his growing pole. She revelled in every inch of his manhood: Dave’s bulging veins, sloped curves, graceful ridge, and reddening rim. Meanwhile, Diane forced her way with Dave, venturing further and higher into his forbidden cavity.

Dave laid there, his legs pulled up to his chest with his girlfriend slowing pushing a 5” dildo up his ass. He could only stare into her eyes watching the lust on her face. He could feel himself tighten his ass as she was pushing forward. But then seeing the lustful look in her eyes and thinking how he had seen her push the larger plastic cock inside her tight pussy so quick, he knew she must be dripping wet. He felt his muscles relax. His tight hole slowly accepted the hard cock Diane fed it until he felt her hips against the cheeks of his ass. A deep breath escaped his lips and he pushed his ass forward slightly against her.

A smile came across Diane’s face as she bit her bottom lip. She had watched the full 5” of her extension disappear inside Dave’s tight butt hole. She felt a power come within her as she at the same time felt the 7” cock inside her push into her depths.

Dave felt the cock slowly pulled back until just the head was still inside him then slowly again sunk into the depths of his tight opening. His breathing became heavy as Diane slowly increased the pace of her entries into him.

The thought of Diane filled with that large cock as she fucked him combined with the new feelings of his ass filled by her had his chest heaving with excitement. Dave grabbed his knees and pulled then harder to his chest and wider apart, opening himself to Diane as far as he could. She had wanted to take him and now he wanted nothing more than to give into her every whim.

Just as Dave was becoming slightly comfortable with this scene, Diane switched the game up on him completely. "O.k. lover, it's time to get up!" she rashly ordered him. Diane pulled her cock out temporarily and positioned Dave submissively on his hands and knees. "Now you will be my bitch and I am going to fuck you like you need it!" she announced.

In one swift plunge she was inside Dave's ass again, bucking and splicing him open anew with one hand on his belly to pull him onto her pole. Her other hand reached around to stroke his wang with deliciously warm and silky fingers. Diane slapped her torso against his quavering butt cheeks, sending jolts of pleasure up her pussy and into Dave's hole simultaneously. The more she thrust, the more powerful she felt and the feeling was both addictive and freeing all at once.

"Fuck yes that is it!!!" she yelled at the top of her lungs. "Take what you deserve now!"

All Dave could do was try to hold himself up against her onslaught; Diane was surprisingly powerful as she shoved and it took all his might to keep his legs from buckling. She was stroking his dick so perfectly, with her palm rubbing along his sweet spot and with just the right amount of speed and pressure. He was completely under her control, his body was hers to do with as she desired. Dave and Diane were moaning loudly as one now, having their holes and private parts stroked and filled over and again until they both grew feverish and nearing the end.

Diane eyes were glued to Dave’s ass with her cock; yes it now was her cock sliding in and out of him. She loved the look of this extension of her body taking him while the other cock filled her soaking wet pussy. The combination totally took over her body as she felt her orgasm building inside her.

Dave felt her hand stop stroking him and tighten on his shaft. Her grip got tighter as she pulled his hips back and shoved herself as deep into his ass as she could. Diane started to shake as the waves of ecstasy came over her. Her juices squirted out of her filled slit flooding against Dave’s butt cheeks as his legs could not hold her back any longer and he was pushed to his stomach with the cock still buried inside him.

Diane lay on Dave’s back, her breathing heavy, her breasts pulsing against him. Dave took a deep breath as her grasp on his manhood was relaxed thinking Diane was finished.

He quickly learned she wasn’t. Diane rolled off him telling Dave to roll on his back as he felt the dildo pull from him. She quickly pulled the dildo from its harness and replaced it with the pussy cum soaked one from inside her. Diane straddled Dave’s head looking down his body at his still unfinished swollen cock. Holding the base of her attached weapon she lowered it to his mouth.

“Show me how you like your cock sucked, suck me like you have always wanted it done to you” she told him

Dave reached his hands around to sink them both into her hard butt cheeks. With her cock touching his lips he looked deep into her eyes as with broken breath told her, “You have taken me at your will, so don’t stop now”

Diane smiled as she fed the cock into his mouth. Dave tasted her juices as he moved his mouth up to take it deeper until it hit his throat. Diane pulled back slowly starting to fuck his mouth. She then lowered herself down to take Dave’s cock into her mouth as they sucked each other.

It wasn’t long before Diane felt Dave‘s cum build in the base of his cock. She felt him pull her down to take her into his throat as his body went rigid and his pulsing weapon was pushed deep into her throat. The first gush of cum completely filled her mouth and swallowing as fast as she could the second wave forced her mouth off him, covering her brow and shutting into her hair.

Diane had never felt Dave cum so hard or so much. Taking his cock back into her mouth she tasted his last drops and then licked him completely clean until she felt Dave pull her around to him kissing her and holding her tight. They never spoke, just held one another gently kissing until sleep took over them both.