Sara's Will to Win

Sara and Will disagreed. It wasn't terminal, but both of them were stubborn types that liked to get their own way.

"We'd use it everyday in summer! I don't see why you can't sign up for this!" Sara pleaded her case with Will as he played with his cereal, deep in thought.

"It's the upkeep, and not just the initial expense, but every year more money getting poured into it. We have heaps of friends who have a pool, can't we just visit whenever we want... like we did last year?"

"But.." Sara was exasperated. This was a conversation 6 months old. "But... I just WANT one. So I can swim whenever I want!"

"It's just too much. 50K? That puts us 3 years behind our mortgage repayments. That's 3 years earlier we can quit work, or go part time..."

"I know that," Sara interrupted, "But what about now. What about enjoying your life. It's just money."

"I can't agree, my dear. It's too much." And no more was said until they hit the road.

It was their anniversary weekend away, driving north to the mountainous hinterland that descended onto a sandy cove, a half hour from their home. Hidden in the forest were cabins littered at private intervals up the gentle slope. It was their third trip to this same cabin, and they'd always had a great time. Hopefully a great time awaited them to alleviate the cloud that hung over them during the trip in the car.

Clearly, it was still on Sara's mind.

"Is there nothing that would change your mind?"

"No."

"Literally nothing? There must be something. I want this pool."

"Not that I can think of? Win the lottery perhaps?"

There was a cold silence.

"I want the pool."

And then more silence.

They pulled in to the cabins carport, and began unloading their cases and food. Will put together a light lunch of cold meat and salad. Looking out over the crystal clear water rolling into the white sand, Will spoke.

"Ok. How far would you go for a pool."

"Pretty far I think."

"You up for a challenge?"

"I'm ready, Will. What have you got."

"You have to beat me in 3 out of the 5 challenges I set this weekend. And we can have the pool."

"Okay. I'm in, obviously."

"Challenge 1: The Longest Nude. Total time over the weekend."

"Yep." Sara started to look slightly apprehensive. She had guessed there might be an element of sex to the challenges... but how far would she actually go when it came to winning?

"Challenge 2: The Consecutive Nude. Longest streak of nude. Challenge 3: This one is a gimme for you. The Most Orgasms. How do you feel about this so far?"

Sara pulled out her phone, sat it on the table and swiped up for a timer. Standing up, she lifted the hem of her dresser her head in one easy movement, unclasped her bra, and shimmied down her underwear. Upon sitting down, she theatrically pressed the timer with an extended pointer finger.

"I'm winning two of those so far, and the other one is currently a tie."

"Ok. Challenge 4: The Least Clothes. We can do that one at dinner tomorrow."

"Ha! Easy. Do you secretly want this pool? I've got you cooked."

"We'll see. And Challenge 5: The Most Exposed. That's how many people see you naked."

They sat in silence while the various permutations of how the weekend would roll out played in their imaginations.

"Do you think you can win any of these?"

Will seemed calm and too quietly confident for Sara'a liking. "I don't know,' he said "but I'm willing to put 50K up to see you try. I'll try and keep you honest."

And with that, Will mirrored Sara's undressing, starting his timer three minutes behind hers. They sat, naked, enjoying the warm spring air, chatting about their work, their future plans, their friends, their not-friends-anymore-due-to-salacious-rumour-mongering.

"So, we have dinner booked tomorrow?"

"Yep"

"But otherwise I could just sit here and win two challenges straight away?"

"I guess so? But I could go and sit on the beach and win at least one of the challenges. Maybe two if I'm feeling frisky. Might all come down to dinner eh?"

"Which, clearly, I'll win. You've not thought this through my love."

"Maybe not. But maybe I have."

Sara narrowed her eyes at Will. His was not an especially expressive face at the best of times. Was there something else going on? Anyway, she thought she would have it covered. Sara headed inside, and emerged with a magazine and a gin and tonic.

Lying on the sun bed, she looked radiant. Tallish, long-legged, painfully white skin and shoulder length blonde hair gathered messily up in a bun, Will enjoyed the view of his wife of 5 years. Her pert breasts still sat high and firm, her areola so light shaded they nearly disappeared into her skin. She was absolutely the one for him. Despite their stubborn streak, they enjoyed the easy comfort of wanting the best for each other. Will had spent 6 months re-training for a different role at work while Sara supported them. Sara had not abandoned her ambitions as a journalist, which meant frequent travel, and they worked it out together. There would be kids, no doubt, and moving houses, and disappointments. They were both sure these were tasks to be tackled together.

Will was reading a book, and noticed Sara getting restless after an hour of relaxing on the deck. She checked her phone, did a crossword, wandered around the house aimlessly.

"I'm not letting your stupid challenge get in the way of a good time. I'm hitting the beach. I'm going to win anyway."

"Cool. I'll come too."

Sara disappeared into the bedroom and re-emerged with her annual new anniversary bikini strung loosely at her sides and breasts.

"Floral patterns are in this year, it's all you can buy at the moment. Timer is paused! Oh!" Sara stopped in her tracks as she saw Will still naked, trunks and towel over his shoulder, waiting at the back door that led down to the path to the beach.

"I have three mins to catch up, thought I'd risk it on the way down."

Sara playfully slapped Will behind as she sauntered past. "I'll walk in front to give you a heads up the eh?"

"Won't need it."

As they made their way down the path, Sara in front wiggling her round ass side to side for Will's amusement, it was just as Will had checked his timer at 2 minutes that they heard the distinctive sounds of footsteps coming toward them.

"Incoming!" Sara whispered, looking over shoulder, continuing on slowly to let Will get his bathers on.

"I've still got a minute to make up!" Will replied.

The footsteps were perhaps 20 metres down and around the bend, and Will made a hasty decision. Emerging around the corner was a 40-something-ish lady in an athletic one piece suit, a swimming cap and goggles pulled tightly over her head. She didn't look up until she greeted Sara as she passed, and then unconsciously waved to the still naked Will. A muffled "oh my" was all that escaped from her shock, which is when Sara looked around to see Will just pulling up his trunks.

"Will!! What are you doing?!"

"Taking an early lead. I believe our naked times are now even, and I'm up 1-0 on challenge 5."

"Damn you... How could you do that?"

"Just throwing down the gauntlet. Do you want this pool or not?"

Sara growled like a possessive dog as she walked. They emerged onto the beach as the sun was setting behind the hills to the west, and they swam in the cool water until the breeze pimpled their skin.

Over dinner, naked since arriving home from the swim, Sara outlined her plans for the next day.

"Can we agree that it only counts if we're together? I really want to go shopping tomorrow at the markets, and you can't just stay home and rack up the nude time."

"That's fine by me. And fair."

"Cool. I want to leave early, say 8?"

"Sure."

"So let's not have a late night." Sara stood up and cleared the dishes. She reached around Will from behind, and ran her hands down his bare chest to his lap, and turned her head for a deep kiss.

After they both feel asleep, the score for Challenge 3: The Most Orgasms, was even at 1-all.

*****

8am, and Sara was getting in the car to head to the markets. Will emerged sans clothes, albeit bundled up in his hands.

"Just racking up a few extra minutes..." Will hopped in to the passenger seat, and piled his clothes on his lap.

"Doesn't count. Clothes have to be on the floor." Will rolled his eyes and complied.

Will lost his nerve ten minutes into the trip as they got on to a highway, and the risk of exposure from trucks was high.

"Don't want no truckers perving on me..." Will said as he shuffled his pants back on. "Okay, I'm at 14:10mins for The Consecutive Nude. Make sure you do your maths before the weekend is over."

"Ah man, I forgot about that one! Isn't it basically the same challenge as the nude time one?"

"It sounds the same, but it's now more complicated for you. You have to be nude for 14 hours straight to beat me. I think you might find that difficult before we leave."

"Hmm. So. Where are we at?"

"I'm winning challenge 1, 2 and 5. 3 is a tie, and 4 is on tonight. You're in a spot of bother. You mustn't want a pool that much."

Sara bristled at Will's tone. But she knew she was in a bit of trouble. She was willing to concede the Consecutive Nude, and she was confident she could get some extra orgasms in. Will could get off twice per day at most. Sara thought she'd win The Least Clothes challenge, but didn't know if she could expose herself to anyone, let alone the two people needed to take the lead for The Most Exposed. So that meant she needed to win The Longest Nude, and that obviously had to happen outside the cabin, when Will couldn't match her. She had some thinking to do.

At the market, they strolled hand in hand through various trinket and clothes vendors. They bought coffee, and brownies, and sat and people watched for a leisurely hour.

"I'm going back to that clothes shop I liked. Adele's I think? What's my budget?"

"Ha! You can get whatever you want! Up to the value of $100..."

Sara slapped will on the arm as she headed off to the curtained Adele's Dresses, Will trailing, hands in pockets, behind her.

Will was surprised at the voracious intent Sara showed selecting clothes to try on. She was usually very picky, but in no time there was a pile of five flowing dresses that Sara was taking into the dressing room.

Will waited outside the shop, and his phone pinged a short time later. A nude Sara, holding up a dress to her side, captioned "catching up one minute at a time."

Will smiled to himself, and sent a cheeky kiss emoji back. In his mind, he'd win The Consecutive Nude, The Most Exposed, and The Least Clothes at dinner was a lock. He wouldn't win The Most Orgasms, and he was happy to concede The Longest Nude, and still win overall. Unless Sara could do something outrageous, which he thought was unlikely. She was playful, and sexual, but not dangerously daring.

His phone pinged again with a dressed Sara in one of the dresses, and he gave a thumbs up. This routine continued; a nude Sara posing with a dress, followed by a clothed version, for all five dresses. Sara emerged after twenty minutes.

"Two to take home, and came in under budget."

"And how much nude time have you banked?"

"12 minutes. 2 minutes ahead of you I believe?"

"Correct."

"What kind of pool would you like? Saltwater?"

"That's a little premature."

"It's a done deal. I don't see how you can win this thing?"

"Funny. I was just thinking the same thing." Will turned and ambled off down the market row leaving Sara's look of consternation to hang on her face. She shook it off and followed.

******

Back at the cabin, a stalemate had been reached. There wasn't enough time to get the 14 hours Sara needed to win the consecutive nude challenge before dinner, and Will know that if he stripped off, so would Sara. There was one challenge that Sara needed to get the upper hand on, however.

While snoozing on the deck after lunch (an anniversary routine they had developed organically over the years), dressed in her bikini, Sara feigned absorption in her magazines with Will reading sports on his phone. She began by lightly touching the edges her bikini bottoms, feeling the material against her skin, stroking her hand up and down along the seam lines. Sara progressed to using two fingers to stroke over her mound, continuing for a minute before she slipped her and underneath to access her slightly moist lips.

She worked up and down, steady paced, still pretending to read the magazine. Will hadn't noticed anything so far from his seat on the opposite recliner. But he would in a minute of two. Her rhythm picked up, her hand now reaching far below her sensitive clit to her inside thighs, and brushing up across her tummy. Surely her exaggerated movements would attract attention, but so far Will had remained unperturbed.

Will's eyes lifted momentarily as Sara rolled on her side to retrieve something next to her recliner, but quickly were back to his phone. As Sara grabbed the vibrator that was hidden away, she also slipped the knotted ties off one side of her bikini so that is fell away from her legs. Leaning back on the recliner again, she pushed the button.

The sound finally extracted Will's eyes from his phone, and he slowly took in the scene before him, put down his phone and leaned back on his own recliner.

"Time to get your points up?"

"Yes. This could be all over in a few hours. We can talk pool designs tomorrow."

Will just smiled. Sara lowered her buzzing toy to her prepared lips, and immediately recoiled her head back from the sensation. Eyes closed, she circled to find her spot, and once found, her awareness for all else but her feeling disappeared. Sara reached up behind her head to steady herself on the head rest, while manoeuvring the vibrator slowly in and out of her widening sex. Small moans now escaped from her mouth as she gave in to her building pleasure, her legs also beginning to force themselves unconsciously against the machine. Faster, faster, faster, and louder and louder the repeating action of toy on lips with moans and legs pressing and chest heaving, skin blushing, sweat beads forming on a distantly aware face.

Will watched with fascination a scene he'd only observed on two other occasions, and both of those those were post-coital. Watching with his clothes on, in broad daylight, before anything sexual had transpired was uniquely voyeuristic, and overwhelmingly erotic. His hard on was at it's maximum, and he could have finished off before Sara had even met her climax. But he knew this was her attempt to take a challenge on, and her didn't want to ruin her triumph. Will gently stroked over his shorts.

Sara was close, grasping at imaginary air with her free hand, and knees rocking her bottom on and off the seat of the recliner. Her moans were now one indistinct low hum, and finally she let out a scream from deep in her belly. Sara's hands, both simultaneously, pushed at her vibrator deep inside her. All of her body's muscles contracted, and it looked like she floated momentarily above her seat, before resting gently down like a feather. The wave had come, and was now receding back to the ocean, the markers of pleasure still flushing Sara's face and chest.

She sighed and let out three large controlled breaths. "And I've got plenty more of that. So don't even try to keep up."

"I won't," said Will. "And I can't", he followed, knowing it was true.

*********

"Can we not include shoes? I'd like to keep my shoes on!"

"As long as they're heels!!!"

"Fine!"

Sara emerged in one of her new dresses; a light green maxi, with a tightly fit bodice, a V neck extending between her breasts, flaring from her hips down to her mid calf. The pattern had small cartoony people all over it, done by some local artist no doubt.

"What do you think?" She asked as she gave twirl and flourish of her hem.

"It's nice. I love the shoes too."

Sara lifted her dress to show off her black heels. "I don't think they match the dress... but, meh? As long as I can claim my victory. Which shouldn't be hard, as I'm only wearing one item of clothing." Sara raised her eyebrows in a questioning way, daring Will to respond. "So, to win, if my maths is correct, you'll be eating dinner in the nude?"

"Not quite. You need to win three challenges, so if we tie one of them, and win two each, I win."

"But... what? You still have to get yourself into one piece of clothing for dinner? Did you bring a onesie? Will they let you in in that?"

"I doubt it. I'll be appropriately dressed."

And he was. Just simple beige chinos and a button up shirt. Sara was again doing the calculations. She'd win this one, the Longest Nude and The Most Orgasms. Maybe Will was conceding defeat because he loved her? That was a possibility, but not likely. Not because he didn't love her, Will just loved a challenge. Sara assumed he had some kind of plan to sneak some extra nude time in. She was determined to match him, and stay with him for the rest of the weekend, which had only 24 hours left in it. Will drove to dinner with Sara feeling supremely confident.

Sara and Will were standing at the front of the service area when a very young waitress bounded over and greeted them.

"Hi guys, do you have a reservation?"

"Yes," said Will," I called earlier and spoke to Ashley about a table?"

"Ah yeah, Ashley told me to look out for you, I'll grab her."

Sara was looking at Will through the side of her eyes. "Ashley?"

"Yes. I talked to Ashley about a table."

"What's going on here, Will?"

"Hi Will!!!!" A voice behind them shouted. Sara spun and saw a small pixie looking woman with jet black hair plastered to her scalp approaching Will with her arms out. Will embraced her warmly.

"Hi Ashley, great to see you again! This is my wife Sara."

"Nice to meet you, Sara. Welcome to Georgio's. I'm sure you'll have a great night."

Sara was a little taken back. "Hi. Umm, do you guys already know each other?"

Will and Ashley looked at each other while suppressing a giggle. Ashley spoke for them.

"Yes! Will and I roomed together at College... what.... 10 years ago? When he called, I answered the phone and he recognised my voice. We had a right little catch up didn't we?"

There was a conspiratorial giggle from Ashley, and Will, expressionless as always, gave nothing away.

"Yes we did. It's really great seeing you again. Did you get us a good table?"

Ashley winked. "The best. Follow me."

Ashley led them through the main dining hall, and around a corner toward where the kitchen was. Tucked away, nearly out of sight, was a booth up against the wall. She led them over and motioned them to their seats. Chefs and waitstaff hustled past them at regular intervals.

"This is where I can give you special attention. I'll be your personal waitress tonight, if you need anything, it's me you'll want to talk to. I'll be back in five to take drinks, orders, or anything else you like. Ta ta!"

"I've never heard you talk about Ashley."

"No. We roomed together for 6 months. Right at the start of college."

"Did you... you know?"

"Oh no, of course not! We got on well. She's gay. But we hung out a bit, she swapped to an arts college, and we lost touch. I haven't seen her since then."

"Okay. This is quite a private little booth isn't it?"

"Yep. I asked for something special. She promised to look after us."

"So. I'm wondering. How are you planning to win this competition? It's like you are rolling over and conceding. Did you actually want a pool this whole time? What's the go?"

"You are counting your chickens a little early. There's still 24 hours to go."

"But. I'm winning Challenge 4, with my one piece of clothes. I'm ahead by 2 minutes on Challenge 1. I'll definitely win Challenge 3, because you don't have my stamina. And you can win challenge 2 and 5. So I win 3 to 2 right?"