M is for Masturbate


Caution: This Sex Story contains strong sexual content, including Masturbation, Petting, Squirting, .

Desc: Sex Story: Jack and Kay embark on the wildest contest ever concieved together

"Hey buddy, how'd you like to have a chance to win a million dollars, and have fun doing it?"

Jack attempted to give the guy a wide birth. He wasn't that he looked creepy or anything, but he was sure it was some kind of a scam. "Ah no thanks," he said nearly stepping down into the gutter.

"You enjoy masturbating?"

"Ok, now it's gotten creepy," Jack thought as the guy handed him a flyer.

He made it around the guy not daring to even look back, half tempted to just wad up the paper he'd been given and throw it away, but with his luck, some cop would site him for littering.

"Read it, don't just toss it," he heard from behind as though the guy was somehow able to read his mind.

Jack made it to the corner without incident. He'd been on his way to pick up his early morning coffee from a nearby Starbucks. Spotting a trash container just outside the door before entering he made his way towards it. At the last second he glanced at the wrinkled flyer and stopped dead in his tracks.

"Enjoy masturbating? Win a million dollars for doing it!"

The problem was, Jack did. Especially as he was currently between girlfriends at the moment so had been doing so frequently. A young attractive looking woman came up to him at that moment however and spoke. Embarrassed, Jack crunched the paper he was holding before she could see what it said, still about to throw it away. Which is when he realized, she was holding one too!

"Thinking about it?" she asked.

Flustered, Jack felt his face grow crimson. "No, not really. This guy just handed it to me, didn't even know what it said," Jack responded lamely.

"Oh, too bad," she smiled reaching behind him, forcing Jack to step out of the way so she could enter through the door he was still blocking.

"Sorry," Jack apologized once again allowing her to enter, which she did. He stood there for a moment longer, staring back at the crumpled paper, then towards the door where he could see her placing her order inside. Jack entered.

He'd stood in line waiting for his "Mocha Latte' Grande, skinny" spotting the girl he'd briefly spoken with sitting over in a secluded corner of the shop. Jack approached, uncertainty written in his face.

"Excuse me, but would you mind it if I joined you?"

She smiled, "Not at all, feel free."

She was attractive, but not overly so. Not the kind of woman that would turn heads more than once. But having a disarming smile and way about her that just made her average ordinary features suddenly appealing. She wore her hair long, pulled back into a ponytail, medium sized breasts that neither jumped out at you, nor caused you not to notice them either.

"Thanks," Jack said sitting down.

"So. You thinking about it?" she asked pointedly.

"About what?" Jack answered evasively, answering a question with a question. She laughed.

"Maybe you wouldn't make it through the auditions," she said flatly. "You're too shy for one thing, and certainly inhibited."

Jack was truly at a loss for words.

"Did you even look at it? The flyer," she reminded him not accepting his 'act'. Maybe you should."

Jack took the crumpled paper from his pocket where he'd stashed it, spreading it out on the small round table between them.

"Enjoy masturbating? Win a million dollars for doing it!" Jack read again, then continued.

The flyer went on to say that there would be ten teams made up of men and women, all carefully selected through auditions, which would continue throughout the rest of the week. Various times were included as well as the location which happened to be an old movie theatre now turned into a 'Comedy Club' that he was very familiar with. It mentioned only briefly that there would be challenges, and as those were either met or failed, teams would be eliminated until there was only one final pairing. At that time the final pairing would be given the final challenge against one another for the million dollars.

"This is for real?" Jack said finally looking up. She was grinning.

"Yep, it is! I've already called the number to verify it. By the way, my name's Kate, though my friends call me Kay," she said extending her hand. Jack took it.

"Ok... Kay... Kate," he amended quickly feeling awkward, then silly at the double sound of her name.

"Call me Kay," she said easily. "And yours?"

Jack felt like a fool, like some teen-age pimply kid about to feel his first tit. Though why he felt that way sitting here as he was, he had no idea.

"Ah Jack," he said simply.

"Ok... Ah Jack," she responded with that same disarming look, and then burst out laughing.

"What's so funny?"

"Was just thinking."


"Well, if somehow we do both manage to make it through the auditions, and dependant upon what kind of challenges we're given..."

"Yeah?" he interrupted briefly.

She laughed again, and then continued. "Well, it will be the first time I've ever jacked a Jack off!" she said giggling.

"Oh yeah... guess it would," and then he laughed, though his head was now filled with the image of her doing just that.

The reason Kay was even there having coffee was because it was her intention to be amongst the first to audition, figuring it would give her a better than average chance. The first time was less than an hour from now, just a short walk further on down the street.

"I'll be right back," he told her. "Don't go anywhere... I need to make a phone call!"

Jack called into work informing his boss who he got along with very well that something important had come up, but not only that, he might also have to re-schedule his upcoming vacation a little earlier than he'd originally intended.

"Well?" she asked upon his return. "Everything 'cum' out all right?" she asked emphasizing the word. Once again Jack felt his face flush.

"No really, I really did need to make a call. So now... I can go with you," he finally smiled excitedly. "I just hope this isn't some kind of race to see who comes first or something, or last for that matter. I wouldn't win either."

"That's nice to know," Kay responded with a flirtatious look. Which then caused Jack to wonder about something else.

"You know, if that is the case, if this is some sort of a kinky race or some kind of endurance test, wouldn't a woman have a distinct advantage over a man?"

Kay spun the paper back towards him. "You didn't finish reading it, check out the footnotes at the bottom of the page." He did, his eyes suddenly growing wide.

"Only women with the ability to ejaculate need apply."

"Oh!" Jack exclaimed suddenly, looking up into Kay's grinning face. "OH!"

Although Jack knew about it, having downloaded a few movies off the Internet, he'd never actually known, or seen a woman who could. As he and Kay made their way towards the old theatre, visions of Kay doing that filled his mind now too. In fact, he had all kinds of wonderful thoughts racing around inside his head, and an erection to match.

"Nice!" Kay said looking down towards him. "Glad to see you getting excited about this!"

Jack nearly stumbled, taking a quick glance down at himself as he'd tripped over the curb.

"It's ok Jack," she leaned in whispering. "I'm horny too!"

As they turned the corner, they both stopped short. A line with at least thirty or forty people standing in it stood waiting to get in. "Ah oh, maybe we should have come earlier!" Kay said in surprise. "Come on!" she said grabbing his hand, forcing him to keep up as she all but ran towards the end of the line. Which for Jack wasn't an easy thing to do with a full-blown erection.

Interestingly as he and Kay stood there, Jack noticed that for the most part these were all everyday average looking people. Sure, there were one or two that stood out in the crowd as appearing a little "creepy" as he was fond of saying. But beyond a small handful, these were people you would pass along the street, even see in an office similar to one he worked in himself, "Or..." he considered. "Meet going in to order a coffee."

Ten minutes before the scheduled time, several people came out with clipboards and pencils with questionnaires. They began handing them out to everyone.

A very professional looking woman in a three-piece business suit spoke, "Please fill out these forms prior to leaving today after the auditions, provided you're still interested in participating afterwards."

After that, they were invited in taking various seats within the cozy audience area while another professional looking guy, also in a business suit stood on stage with a microphone in hand waiting for everyone to be seated. After several minutes the back doors were closed and the lights came down with a soft spotlight now on stage.

"Ok, everyone... listen up! I know most of you are wondering if this is for real. I can assure you that it is!"

Jack along with everyone else listened as they were told of a somewhat eccentric, to remain anonymous, billionaire who had come up with the idea while at a party. The more he'd thought about it, the more he liked the idea, finally approaching some contacts he had in the entertainment business who were willing to go out on a limb, all underground of course, and create their own little reality show around the theme of 'masturbation.' He'd gone on to say that the money was already in an account on deposit with the access codes even then held in the envelope, which he held up for everyone to see. It was of course sealed and only to be opened upon awarding the eventual winner.

.... There is more of this story ...

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Story tagged with:
Masturbation / Petting / Squirting /