Grand Champion

May's eyes lit up when she heard the proposal. Her memories transported her back to her glory years, when she was named the Grand Champion of the high school ping-pong tournament. Typical school days: a nameless bitter rival who was far more important at the time than she should've been, and May working her ass off to get to the final. Stress and hormones combined to make a toxic mix, but the elation seeping out of each victory kept her going. At the end, she faced her teenage rival and beat her in a tense match for the the girls, and them alone, even though before now they'd barely known what the other was made of. May basked in the glory of her eventual victory, trite as such a thing may seem. The teachers half-watching were impressed, and she had notions of recommendations and trainers that would ultimately not come to fruition. But she'd held onto those dear memories all this time.

So when this man proposed that they play a friendly match of ping-pong in the basement of her friend's house, years removed from that exciting time, she was floored by the possibilities. As she followed him down the stairs into the dimly-lit basement, clouds of smoke still billowing from those who'd gone back upstairs already, she could feel the thrill of competition, and was ready to vanquish her opponent yet once more. They were alone, face to face, in a battle to the end.

Her eyes gleamed as she gripped her paddle, shooting a confident smile at the man across from her. She took in his casual demeanor and returned his smile with an unnecessary arrogance. She knew she would easily beat him, even if the stakes didn't matter.

"Winner takes all?" proposed the man as he held the ball upright between his agile fingers, idly spinning the paddle in his other hand.

May nodded, her grin glued to her face as the surge of battle flowed into her.

The ball came, spinning off her opponent's paddle before hitting the corner of the table, where it sliced away from her.

It was a hit and a miss.

"My point," declared the man.

The ball was returned and he served again. May stood at the ready, bending her knees in preparation for the reaction and return serve. Again the ball hit the edge of the table and sliced out of her reach.

"2-0," he declared. "It's your serve now."

May knew the rules and wanted to sneer, but she kept the now-plastic smile glued to her face, not wanting to show her nerves. She let her muscles do all the work, tossing the ball into the air and swiping at the ball.

Missing it entirely.

"Do-over?" asked the man, grinning genuinely. Perhaps it was not as mocking as it seemed to May but she doubled down anyways.

"Your point."

The man shrugged.

May served again, this time thwacking the hollow plastic ball, immediately sending it to surface on her side before flew right into the net, stopping its momentum completely.

"4-0," he reminded her.

She tossed him the ball, not looking annoyed but letting out just a sniff of recognition.

He served the next two points, which she held for a few volleys before she eventually succumbed, hitting both returns off the table.

"6-0," came the man's factual delivery.

May had a little dignity left inside, and was prepared for the eventually if he wanted to implement the 'skunk rule' that limited the game to seven points, to ease the suffering of her abysmal performance.

She eyed up the man before taking her serve, almost forgetting the stakes before he reminded her, putting on the pressure.

"Winner takes all," he repeated.

May served without hesitation, clipping the net and allowing her another try.

This time it made it over the net, and they volleyed back and forth until she finally caved, smashing the ball into his clothing rather than the table as he instinctually protected himself.

"7-0. That's game."

"Best of three," May shot back immediately, as if he'd sent her another ball.

"Winner takes all," he reminded her but set down his paddle instead of trying to ready himself for the next serve.

May supposed it was the famed rock-paper-scissors approach to deciding the next server, so she rounded a fist and slapped it into her palm a few times, waiting for the man to do the same.

But he just stood there, his hands at his sides.

She eyed his loose clothing, trying to puzzle out what was happening, when she suddenly realized the mantra he kept repeating that she'd been ignoring each time he spoke.

"Wait, the winner of each match?" she gulped as she finally replied to him.

"Winner takes all," he smiled.

Her heart began to beat fast, and her eyes zipped around his clothing, which traced his shape and tried to puzzle out his conditions for that indisputable victory he'd somehow pulled off. May was a stickler for honor and duty, but she had no idea what the man wanted. He'd never even asked her, and she never pictured herself on the losing end in the first place, anyways.

"So what are you gonna take?" she asked innocently, meekly cutting off as she realized how that sounded.

But the implication was exactly what the man wanted.

"More like, what are you gonna give?" he winked mischieviously.

He was an attractive man, to be sure, with a clean smile, a trimmed beard, and May thought that perhaps even strategically she could get an edge and ultimately play it to her advantage. She thought she noticed a slight bulge in his garments and did her best to saunter over to him, hoping to distract him before the next match. He smiled receptively and confirmed his idea. She reached out a hand and grabbed the bulge, stiff underneath his clothes, searching a way to free it from underneath.

She sifted it out from underneath the layers as he leaned back lightly against the table. His warm meat throbbing in the light now, she lowered her mouth to him. He twitched as the softness of her lips met his exposed skin, and the moist sensation washed over it completely. She bobbed up and down on him as she slid her hand up and grasped the base of his shaft. She stroked lightly until she was in the correct rhythm, moving her neck in time with her hand, until the man groaned at the pleasure. She bobbed, totally in control of the situation now, and gaining the upper hand, she hoped.

Once she tasted the saltiness on her tongue, she came up for air. He grabbed at her breast, and she knew now she held the advantage, which she chose to play rather than continue. She smiled up at him as the spittle glistened off her wagging chin.

"Not yet, champ. Best of three. Remember?" Her smile was so big one corner of her eyes almost winked at him.

He quickly packed his erection back under the folds of cloth and grabbed for a paddle again.

She lifted herself fully erect and sauntered back to her side of the table where she stopped right before picking up the paddle. She instead formed a fist and held it above her other hand which was flattened.

"Rock-paper-scissors for serve," she demanded.

"Winner takes all?" came a less-confident version of the repeated mantra.

"Not for this," she shook him off with her head as she repeatedly slapped her fist into her hand.

"Fine." He set down the paddle and took up the same gestures. He second-guessed himself the first few tries, and his hesitation saw her win the toss.

She was flying now. Her first serves couldn't be returned.

1-0, 2-0.

But he came back the same.

2-1. 2-2.

And she went at him again.

3-2. 4-2.

It stayed close like this, going back and forth until the near the end.

10-7. 10-8.

Until his nerves faltered.

10-9. And a whiff.

Game point. Final serves.

She steadied her position, firing off an nonreturnable volley. Game. Set. Match.

11-9.

A fist pump and a smile. "My turn. Winner takes all."

His momentary shock wore off and he closed his gaping mouth, likely realizing that there really were no losers in this contest. "And what will you ask for?"

Her eyes were changed now, going wide. She was basking in the glory and did not even remember the stakes. He stepped toward her, and her eyes flickered to the bulge in the fabric before she remembered where they had left off from. She subconsciously squeezed her own breast before uncupping the bra and lifting her shirt just above a perky tit and its hard nipple. "Suck it," she said, but didn't need to demand much before he moved toward her, obliged.

He lowered his head and only flicked the tongue to the hard nipple at first, but the teasing didn't last long, just a couple more flicks before he sucked it into his mouth completely.

She threw her head back at the sensation, reaching a hand behind his head in subconscious reaction, and resting the other hand on the table so didn't fall back too far and lose the sensation. Pleasure surged through her as he gripped her back in support.

But when she felt his hand creeping along her thigh and slipping between her legs, she regained focused, shook herself out of it, her hair flapping to either side, and gently pushed at his shoulder, increasing the pressure until he finally backed away.

As her small breast puckered out of his mouth with a plop and he brought his head back up to her, nearly a handspan over her compared to the view she'd had over his head she looked into his intense eyes and for a split second she thought about letting him slide his fingers into her pants, before recollecting herself and remembering the match. She pulled her shirt back over her spit-covered breast and recupped the wireless bra underneath.

It was nearly settled. But not quite yet.

The next game flew by in a haze. May returned the serves that she could yet knew ultimately the winner didn't matter. She was starting to accept it, even though her competitive edge still drove her to make a concerted effort. But underneath the guise of apt competitor, her pussy was soaking wet, waiting for at least a finger or something more. She didn't anticipate the results, just played on until the final score was announced.

"11-5. I thought you had me there for a minute," her competitor announced graciously with a soft smile. He was conceding, but May didn't really care.

She was just waiting for his request. They stared at each other for a while not saying anything, hearts pounding with desire, before her opponent did manage to recall the final score and victory conditions.

"So it's really winner takes all, now isn't it?" His grin turned mischievous, but in a slightly menacing way. A completely unexpected change of demeanor.

May was dripping and secretly hoped for some form of penetration or clitoral stimulation, but she knew men could be selfish as well. And fair enough, the win was indisputable his. Best of three, even.

"Yes, that's what was agreed upon. So what'll it be?" May replied robotically.

She stiffened and turned as still as a scarecrow in a farmer's field when his response was to walk over toward her, not even naming the request aloud.

He ran the back of his fingers along her stomach where the fabric of her shirt separated from her pants.

She shuddered.

His hand then moved to her back, and she wracked her brain to figure out what he was going to ask her for.

She began to tremble as he ran his hand down her backside, patting her on the behind gently.

"I think this is mine now."

She tried to comprehend, but it didn't take long before the hint was received.

He made his way behind her and pulled her pants down along with her panty exposing her rear cheeks.

Bare-backed, feeling the chill of the air on her behind, she relaxed a little still unsure of the request. But she was resolute, and would perform her duty as it was posed to her. No matter what. She was bound to her word and would not break her honor. Not even for this silly thing.

She squeezed her pelvic muscles as his hands massaged her bare ass. He pushed up on them, and she almost tried to look back as he surely enjoyed the magnificent view. She may have lost, but she knew what she had there. She felt the heat of his member poke into her leg at an awkward angle just beneath one of her cheeks, and still wasn't sure where he was going.

But she would stick to her word.

As she felt his cock probing randomly into her soft flesh she steeled herself, relaxed her muscles. She was hoping for delectable vaginal penetration, but his probing didn't reach it. Instead she felt it push into her anal cavity, once, twice, then knew that he was probing for the smaller, lesser used orifice.

She closed her eyes and they rolled back into her head. She was duty-bound, and told herself she could endure.

Luckily for her, even in her dedicated silence of concentration, he readjusted, pushing the head down toward *her* preffered opening, picking up her juices along the way, slickening his head and her butt crack alike, alleviating friction as he continued to poke away, entering slightly now.

May braced herself further, and his strong hand gripped her wrist.

But he was cautious. Quite the gentlemen considering the circumstances.

He explored her orifice a little more, poking the head just inside, but not going all the way in for some reason. But she was ready now. At least she thought.

Finally she placed a reassuring hand on his hip. This man was really too kind. *But it was time for him to take what was rightfully his*, she thought as she pulled him gently toward her. He leaned down and kissed her shoulder.

That was it. The soft hand on his hip awoke his desire. He pressed into her and reached for a breast as the other hand still gripped her other wrist. He slipped completely inside her ass, and May winced more in anticipation than in pain.

As he thrust into her behind, clawing at her exposed breast and never letting her escape too far, his hand pulling her wrist back against her body in rhythm to his incessant pounding, slapping against him harder and loudly. So much, in fact that despite the lack of moaning their slapping bodies caused commotion that required an investigation of the basement.

In fact, when May opened her eyes her competitor still pounding away behind, she was confronted with an onlooker.

"Who's got next?" asked the other man, nonchalantly.

Extraordinarily, May's competitive spirit kicked in. She was still bouncing back against her first challenger, yet managed to pick up the paddle in her hand.

The new man picked up his paddle as if this was normal. He even volleyed a serve in her direction as May continued to have her ass rocked with the cock of her vanquisher, the first.

She struggled mightily, though, missing both first serves, then failing to do any better with her own. She missed the table or the ball completely. It was a complete disaster.

Or was it?

As her opponent racked up his points, 2-0, 5-0, 11-0, May didn't lament what seemed to defy her competitive spirit. Years ago she would've broken down in tears at such relentless humiliation. But she was allowing this to happen, and her opponent didn't even know why.

Until she spoke, in interrupted breaths. "Winner... takes... all."

"Oh fuck," warned her first opponent.

She could feel him throbbing inside her ass, ready to blow.

"Not... yet!" she labored breathily.

He paused, a little too obediently for May's taste. "Sit down," she commanded since he was going to be like this. She gestured to a chair near the table.

He moved over to it, not pulling out, but pulling her along. As he sat down and pulled her on top of him, still inside. May did her best to straddle him, placing her feet on his legs one at a time, stumbling a little but held upright when she attempted to pull down her pants the rest of the way and then kick them away.

"Um, do you need help?" asked the second opponent bemusedly.

May ignored him for a second, instead grinding against the first man with his cock still inside her. She never anticipated liking this so much, and was ready for more.

But their new angle stretched her a little uncomfortably. Painfully pleasurable for lack of a better term. She winced but tried to wipe it from her face as she gestured to the other man.

"Come over here. I said winner takes all. Did you hear me?"

The man walked over to her smiling, but still utterly confused as he didn't know what she wanted him for.

To May it was quite obvious. Her pussy was there for the taking.

Couldn't he see that?

Then she had an epiphany.

Ah maybe he didn't get warmed up!

He was a little bit older than her she saw now, with handsome gray streaks running through his full head of hair.

She lifted her shirt over her head, taking bra with it, hoping that her exposed body would do the trick.

He was slow, but he wasn't that slow. He finally noticed that the other man's shaft was buried in a different hole. "Oh, wow, he's deep in your ass."

"You have no idea," May winced. "Still one more to fill. Can you lend a hand?"

As he reached a literal hand toward her and came closer, she grabbed for his trousers and tugged, setting free a bouncing man-sized cock. She was glad he wasn't her first opponent, that was for sure.

"I didn't mean an actual hand. Fill me with this monstrosity."

He nodded. The man took off his shirt first, though, unexpected lean muscle rippling under his flesh. His body could've belonged to a 20 year old instead. May was impressed, but still patiently awaiting her formal request. She had to smile, remembering that it was supposed to be the winner asking for the next favor. She'd twisted the game in her favor.

And as he lowered himself and worked his way inside her, May knew she had really won, despite the actual scoring. The older gentlemen kissed her cheek as the first man kissed her neck on the other side, and she felt stretched to the limit of her insides, but delightfully fulfilled. The older man grabbed her by the hips to steady himself as he plunged inside her.

The seesaw she rode moved her back and forth dragging pleasure out of her nerve endings from multiple angles. Her heart was racing and her pulse kept on quickening, warning her of the impending orgasm.

"Oh shit," the first man warned her again.

May knew she had to be quick. She closed her eyes and focused on every pressure point, could feel her chest swelling with pleasure as she clenched both her ass and pussy. They twitched, spasmed with mini-orgasms as she rode the final wave home.

She bounced on the seated man and felt him filling her ass, then pulled the older man toward her by his hips. She could feel him deep inside. They both pushed toward the same point inside her, where she focused her mind and finally burst into orgasm. As she quivered she felt the wetness coming inside her from the distinguished older gentleman. She let both of them pump her full as she rode her orgasm back down.

She stroked the older man gently across the hip with the back of her hand, then turned to nuzzle her forehead into the first man. "Game. Set. Match. And gentlemen, it looks like I'm the winner."

They both laughed, the older gentleman pulling at her nipples as the first man caressed her rear end.

"I think we've all won tonight," said challenger number one.

"I'm definitely ready for a rematch," claimed the second, much to May's delight and surprise. He pulled out and stood up. May took his semi-erect member and pulled it to her, tasting the tart mixture of both their juices.

"So am I..."