The Quarterly Competition

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A woman sets out to discover the secrets of a mystery man.
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ShyChiWriter
ShyChiWriter
1,993 Followers

Hello, All Lit Readers!

It has been so long since I have posted anything new up here on Literotica. Life, career, kids, and grad school tend to tie up time, let me tell you!

Here is my entry into this year's April Fools Day contest. It was an idea that came to me a while ago, and I thought it would be fun to try and write it down. A bit different from my other efforts, but I had a good time writing it.

Thanks in advance for reading and (hopefully) voting. Any comments, constructive criticism or otherwise are greatly appreciated.

***

THE QUARTERLY COMPETITION

July 1, 2018.

Cabo San Lucas, Mexico

Lynn marched out of the ladies room, carrying her trophy, to a round of applause. She'd just won Cabo Wabo's Wednesday Wet T-Shirt Contest. Along with a prize of a hundred dollars, she'd won the cheap plastic trophy and the much-wanted attentions of most of the guys and some of the girls in the bar. Not wanting to be too overt, she had gone back and changed into her short floral dress (no bra, thong) before greeting her adoring public.

Something had told her she was going to win. Twelve years of modern dance didn't hurt her chances. Neither did her disproportionately large breasts that, even at age 24, still rode high and proud and stood out in contrast to her slender frame. Above all, she knew it was her attitude that made her the champion. It had just taken a couple of shots of liquid courage, and she'd slid into the zone of sexy confidence that she knew was critical to this sort of thing. She'd radiated sex up on the stage, and she could have sworn that the heat of her body had turned the water on her T-shirt to steam.

She willingly accepted the drinks offered to her, though she did pace herself. She liked to keep the same nice buzz that had given her the courage to hop up on the stage, but she didn't want to get sloppy.

As she flirted and danced her way through the bar, she saw several possible candidates. A gorgeous boy from Spain was her top choice. He had limited English, but if they ended up hooking up, there wouldn't be much talking. Then there was a big old farm boy from Texas who looked ripped from work on the ranch, and football. She was fairly certain that he wouldn't necessarily excel in technique, but he would have stamina.

For some reason, however, the tall man in at the corner of the bar with dark hair kept catching her eye. Maybe 6'3" or 6'4", he was wasn't dancing, but just had a smoldering glaze that swept over the room, occasionally coming to rest on her.

'Playing the cool and aloof approach, huh?' thought Lynn to herself. Well, two could play at that game. She kept her distance and continued grinding on hot guys and girls as the music kept up. Still, she kept an eye on him, and it felt like every time she looked his way, their eyes met.

After about half an hour, she finally gave in and made her way over to him. The closer she got, the more she appreciated him. He was tone and fit, not ripped, but more of a swimmer's body. This translated to broad shoulders and strong chest. Below she could see that he was definitely packing some serious equipment.

"Hi, I'm Lynn," she said above the music.

"Fred," said the tall drink of water. "Nice to meet you."

"You, too," replied Lynn.

He looked her body up and down with admiration. "That was some performance up there. I bet you're a wild thing in bed."

"You have no idea," she half-shouted to be heard above the music. "No guy has ever been able to keep up with me. Ever."

His eyebrows raised in surprise, but not in a bad way. He bent down and kissed her with no warning. It was a kiss that would have curled her toes up to her thighs if possible.

"That wasn't a challenge," she half gasped into his ear.

"Wasn't it?" he said, confidently.

"Okay, maybe it was."

Fred pulled out his phone and started texting.

"What are you doing?" she asked.

"Letting my friend know he needs to find somewhere else to sleep tonight," he said.

He pushed send, slipped his phone back into his pocket, and took her hand.

***

Her thong didn't even make it back to the hotel. Somewhere between the bar and the hotel, she found herself tossed up on a rock wall and Fred's tongue buried deep into her wet folds. Within minutes, she had a mind-blowing orgasm that had her squirting over his face.

A couple of blocks later, Fred pulled her behind a building, slipped on a condom (good boy), and lifted her easily to slide her down onto his cock. For the next ten minutes, he proceeded to toss her around like a willing fucktoy (which she was), holding her suspended on his cock. The only time he paused was to readjust his grip due to the sweat, or to shift her around for a new position. When he finally came, she had already experienced two additional orgasms. Leaving the discarded condom behind the building, they walked hand in hand to his hotel. Lynn, on wobbly legs. Fred, seemingly unphased by the athletic, sexual display he had just put on.

She wondered if, perhaps, this was the guy who could keep up with her.

For the next several hours, Fred rocked her world in ways she never could have imagined. Every rhythm, every position, every speed, he was unstoppable. What was more, it wasn't like he was holding back and counting on stamina. She lost count of condoms after seven. Hell, she pretty much lost track of her name after the sixth condom.

In terms of orgasms, even if she'd tried to count, it would have been pointless. Her state-of-being had turned into more of a solid wave of pleasure as opposed to individual climaxes. It was now just peaks and valleys, but even the valleys were higher than most peaks she'd had with other guys.

Night turned into dawn, and dawn turned into morning. The only time they stopped was for bathroom breaks, and through it all, Fred stayed hard and reliable. Once the sun rose, he wasn't the ramrod state of the night before, but he still maintained a stiff suppleness that perhaps made it even more interesting. With his wonderful length, having a little flexibility in his shaft allowed for some interesting and wonderful positions, many of which slid across her G-spot in paralyzing ways.

At last, nearing five the following afternoon, Lynn knew she had met her match. She was lying face down on the mattress when Fred returned from the bathroom, donned a new condom, and pressed it hungrily against her ass.

"Please, no," she murmured as the sensation awoke her. "I...I can't."

"You can't, eh?" Fred whispered into her ear.

"No, you win. I'm tapping out."

"That's a shame," he said, though there was a triumphant tone in his voice. "Are you sure?"

"I'm afraid so," she whispered through exhausted lips. "Just give me a few hours sleep and I'll be good for round...forty-seven, or whatever it is. But you are the champion."

"Again," he said so softly she barely heard as she fell into exhausted unconsciousness.

***

Lynn awoke to the sounds of music drifting through the windows. It was dark outside. Checking her phone, she saw that it was almost 11:00 pm. There were quite a few texts from friends, but not of the panicked variety. Around five in the morning, she had gotten a small break and been able to let them know that all was good with her. The messages since then were mostly along the lines of 'you go girl' and variations of thumbs-up or applause emojis.

But, where the hell was Fred. She called for him no luck. She got up and put on the terry cloth bathrobe and started exploring the lovely suite that she only remembered through a sex-filled haze. She checked the bathroom, the balcony. No luck. Then she noticed that was no luggage. What was going on?

After about ten minutes, there was a knock on the door and she jumped up excitedly. She pulled the door open slowly and peaked around the corner with a kittenish grin on her face.

"Hello, there lover."

The man with the room service cart looked a bit shocked but pushed in past her.

"I uh...thank you," she said.

"De nada," said the man, eyeing her slightly open robe uncomfortably.

Lynn glanced about and realized that all she had was her credit card attached to the back of her phone, but no cash.

"I'm sorry," she said. "But I... I can't tip you."

"All paid, all good," said the man in broken English. "Enjoy."

She showed him to the door and then returned to the car. On the tray was a cheeseburger, french fries, ice cream, cheesecake, as well as an ice bucket with a couple of Coronas and a bottle of rose'.

Propped up in the middle of it all was an envelope bearing her name written in neat handwriting.

"Lynn, thanks for an amazing night, and day. You are truly a wonder, but alas, as you said, I'm the champion. The room is paid through tomorrow, if everything isn't to your liking, there's an extra hundred dollars on the room service tab for whatever you want. Wishing you all the best in life and love, Fred."

"Mother! Fucker!" cried Lynn. "It really was a challenge, that bastard!"

She fumed for several minutes before texting her friends and telling them the name of the hotel and the room number. If that fucker was going to ghost on her, she was sure as hell going to squeeze out his room service credit. She looked over the room service menu and figured out what would be the most economical way to spend $100 on alcohol.

***

October 12, 2018

Chicago, IL USA

Bree sat at in her cubicle bashing through the security code for the bank's website. Bree was unusual looking, but the kind of unusual that translates as attractive. A mix of Scandinavian and Asian heritage, she was average height with angular features, long brunette hair hanging to her shoulders without much attention, and almond-shaped eyes with sparkling blue irises. Her body was... well, it was hard to discern. It might have been average or might have been tight, but she tended to favor baggy cargo pants and hoodies of the hacker-variety that made it hard to gauge what was under there, exactly.

This was Bree's third week on the assignment. The job was for a smaller regional bank whose code was woefully out-of-date. When she'd taken the gig, she'd known she could charge top dollar. The bank had suffered two breaches — one to the tune of three million dollars, the other near half a million. Luckily for the bank, they had been able to keep the news from the public, and there had been no leakage of customer data. Also, luckily for the bank, Bree had been available. Her first step had been to bolster the firewalls. Now, she was working with her team to rebuild the bank's website and back-end from the ground up to be more secure than almost any other company's infrastructure.

She could do this sort of work in her sleep. She was looking forward to her lunch date with her new friend, Lynn, the UX designer in the next cubicle. Eventually, the lunch hour arrived and she found herself listening to Lynn regale her about her one, greatest night of fucking while on vacation in Cabo.

"I'm telling you, the best lover ever. I've been with a couple of guys since and it's been nice, but still disappointing."

"He was that good, huh?" said Bree.

"He was so fucking good," said Lynn. "He knew where to touch me, where to squeeze me, where to...spank me. Plus, we did everything. Handcuffs, blindfolds, rough stuff, tender. But beyond all that, he was inexhaustible."

"Oh, one of those machines, huh?" said Bree. "Can go all night without coming?"

"No," said Lynn. "That's the thing, he could last forty, minutes, an hour, even, but he came. A lot. He came, then he was ready to go again almost immediately. Sometimes after a quick trip to the bathroom, sometimes he'd just swap a condom and be back on top of me within seconds."

"So, to be clear," said Bree. "Is what you're describing out of Penthouse Letters, or some Shades of Grey novel?"

Lynn chuckled, but shook her head bemusedly.

"No, not fiction," she said wryly. "This guy rocked my world like nobody possibly could."

"Are you still seeing him?" asked Bree.

"That's the punchline," said Lynn. "We spent one night in Cabo, then the guy disappeared, entirely. Ghosted. I was just some competition to him. He was obviously looking for someone he could outfuck, and he won. I tried to track him down. Pathetic, right? He told me his name was Fred, but that wasn't true. I bribed the hotel clerk, and it turned out he paid with cash and registered under the name... hang on, let me check my phone. Yeah, he said his name was Jon S. Auberon. I've googled that name, searched Facebook, and haven't found anyone who looks remotely like him?"

"Can I see how it's spelled?" asked Bree.

Lynn held up her phone, and Bree looked at it, cocking her head.

"Oh, you won't find him that way," said Bree. "It's an anagram. Let's see... yep, it's Jason Bourne; all scrambled up."

"That's what it was!" cried Lynn. "Well, I can't say if he was an international spy, but I do know he ruined me for life, or at least a little while. I've had sex marathons before, but nothing even close to what I had with this guy."

"Nothing like it, huh?" said Bree, a bemused look on her face.

"Nothing," agreed Lynn.

"Inexhaustible?" said Bree.

"A fucking machine," Lynn said, a distant, dazed expression on her face. "Like, almost inhuman, or something."

***

Over the next couple of weeks, they started going out for lunches regularly, sometimes even a happy hour after work.

Lynn really liked Bree. She was fun and quirky. Like a lot of geeks, Bree was a bit absent-minded at times, sometimes forgetting parts of the conversation from the day before. But still, she was a good listener and often picked up the tab. Not hard to do, since Bree's rate was $425 an hour.

'The Marathon Man' often worked his way into their conversations. Not overtly so and Lynn was happy to share. It was a one-of-a-kind encounter and was easy to obsess over.

When Bree's contract wound down mid-November, they promised to stay in touch.

***

December 31, 2019

Puerto Vallarta

The woman with almond-shaped, blue eyes sat at the bar surveying the crowd. In particular, she was watching the tall blonde man with a swimmer's body surveil the crowd. It seemed he had spotted three or four women whom he found attractive and he was evaluating them by some criteria.

She knew a few things about him. She knew his real name, but she knew he was introducing himself as Michael tonight. She also knew his hotel room, checked in under the name Buck Jarea, which she was fairly certain was an anagram of Jack Bauer. She had hacked into his 'Michael's' regular phone, but unfortunately, he was using a burner this evening that he'd purchased at a kiosk on the Malecon. He referenced his phone frequently, but she had been unable to see whether he was texting or entering some sort of score on the women he was scrutinizing.

At last, she saw him order a round of drinks for a table of girls who had been having a lot of fun on the dance floor.

'Which one,' she mused. 'Which one does he have his eye on?'

She made a secret wager that it was the curvy brunette. Five-foot-nothing, there was something about the woman that just drew your eye to her. She had wide hips, great boobs, and clearly took pride in having a voluptuous body.

Bree watched the guy work the group and, sure enough, he was soon dancing with the curvy, gregarious girl. After about two songs, Bree watched them leave the dance floor and head back to his room.

Bree actually beat them back to her own room. Her team had helped her hack into the hotel's system, duplicate Michael's room key, and install fifteen remote cams throughout the suite, giving her a view of pretty much every possible location as well as several angles of the bed.

With three laptops up, the recording was started.

The door burst open, and the fireworks began.

Deirda, which was the curvy brunette's name, proceeded to get the fucking of her life.

Michael definitely had some serious skills in the sack and a couple of secret techniques that brought a smile to Bree's face.

Deirdra also had some impressive skills of her own. She was an amazingly gifted fellatrix, and Bree found herself both entranced as aroused as she watched him work cock and balls with phenomenal technique and enthusiasm. Bree made a mental note to review those sections of the tape. It was like watching a blowjob masterclass.

Much like Lynn had described, this guy did like his toys. He had blindfolds, handcuffs, and ankle restraints at the ready and he used them incredibly inventively.

By 1:00 in the morning or so, however, Lynn spotted a problem. Deirdra was extremely orgasmic, sometimes climaxing for five, even ten minutes at a time. The enthusiastic young woman had leg-shaking, squirting, full-body orgasms that were certainly enviable, but Bree knew something right away.

"She's going to wear out," she said aloud. "One of those orgasms is like five minutes on a stair-climber, she can't sustain that."

By about four-thirty in the morning, Bree's prediction came true. Counting condoms, they got through seven, but on the last one, Deirdra's moans were almost as if from a sleepwalker. As her body shook with one final, climax, her eyes drooped shut, and she fell into a catatonic state.

Bree saw a triumphant, gladiatorial grin cross the man's face as he stood over the sleeping, buxom beauty.

She watched as clothes were packed, devices were put away, and a note was written.

She kept the tape running, but she already knew the outcome. Deirdra would awaken alone.

***

March 29, 2019

Chicago, IL

Bree and Lynn were out for Friday happy hour. They'd made it a tradition to at least meet on the last Friday of the month, though they had managed to get together a couple of times in between as well.

"So, what are you up to now?" asked Lynn.

"Oh, some stuff for United Airlines," said Bree with a shrug.

"Security?"

"No," said Bree. "Logistics. They've got some old code in some of their baggage-handling system that needs to be updated. It isn't hard work, but the original stuff was written in this old variation of Ruby that hardly anybody understands, so I got the gig for my top rate."

"What do you do with all of your money?" asked Lynn, shaking her head in disbelief.

"Oh, I invest, travel a bit, you know," said Bree, shrugging.

"Travel when?" asked Lynn. Ever since I've known you, you've been working six or seven days a week."

"I make it happen sometimes, no worries," said Bree.

Just then, Bree's phone lit up. Cayman Islands was all it said.

"Sorry about this," she said. "I'll silence it..."

Bree trailed off as her eyes opened her message.

"Shit," she said.

"What is it?" asked Lynn.

"An emergency," said Bree. "A client looks like they've had... a breach."

"Do you have to go?" asked Lynn.

"Afraid so," said Bree.

"Well, at least we got to see each other. See you next month?""

"You bet," said Bree.

With a quick hug, Bree was out the door.

***

March 31, 2019

O Bar Nightclub, Georgetown, Cayman Islands

Bree, with almond-shaped, blue eyes and freshly dyed red hair in a pixie cut flirted shamelessly with the boys (and girls) on the dance floor. She wore a tight-fitting little black dress that put her trim, nubile body on display. She was clearly the belle of the ball and did not lack for propositions. However, it was clear she didn't want this evening to end too soon, and she was also waiting for just the right guy to come along.

That right guy, it appeared, was a tall guy with bleached white hair and a swimmer's body who introduced himself as Adam. Unbeknownst to him, the young woman knew his real name, as well as the condo he was staying in, and that he'd checked in under the name Spiros Wentau (Austin Powers, appropriate for the season.)

ShyChiWriter
ShyChiWriter
1,993 Followers
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