M is for Masturbate

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Many Feathers
Many Feathers
10,479 Followers

"No shit?" Jack exclaimed excitedly, though stunned, as he'd honestly not expected it. "I am?"

He listened while given instructions, told where and when the actual contest would begin, and reminded that he'd need to schedule the time if he was still planning on participating.

"Oh trust me! I've already got things arranged just in case I was selected!" he assured the woman who he remembered in the three-piece suit. He'd no sooner hung up when his phone rang once again.

"Hello?"

"Jack?"

"Kay!"

"Guess what? I'm in!"

"Me too!" he responded happily. He heard Kay sigh a breath of relief.

"That's so fucking cool!" she told him. "By the way, did they tell you who you've been partnered with?"

"Yeah, someone named Stacy?" he said still trying to remember anyone by that name.

"Oh, I think I know who she is. Wasn't she that tall blonde with the big tits? You should be happy about that, might help," she paused. "I got stuck with the fucking model!"

For some strange reason, Jack felt a twinge of jealousy. "Damn...sorry," he told her not really feeling so.

"You excited? I sure as hell am. Fuck Jack! A chance at a million bucks! And all we have to do is masturbate!"

"Maybe so Kay, but it's the where and what we have to do while doing it that worries me!"

Kay laughed. "Don't be so worried. It'll be both fun AND exciting. You just need to keep things in focus, keep alert, and enjoy yourself. Even with Mr. Model, I'm planning on doing just that. And more importantly, I'm going to win this fucking contest!"

"You know Kay...if anyone can. I think you probably will too!"

#

They'd been given a set of instructions, told to "dress appropriately" suggesting clothing that wouldn't hamper activities. No belts, underwear, or things that would prove difficult should the situation arise. As agreed, he met Kay at the Starbucks for coffee, something that had become personal now for them, looking at it as a good-luck omen, and a good way to start things off.

"Nervous?"

"Hell yes! Aren't you?"

Kay giggled. "A little, but damn fucking excited too!"

They soon made their way over to the Comedy Club and joined all the finalists anxiously waiting for last minute instructions along with their first set of 'challenges'.

"Good luck!" Kay said honestly. "Remember Jack...stay focused!"

"Before we begin," their host said gathering everyone's attention. "Unfortunately there have been a couple of last minute changes. Kay Dalton? Are you here?" he asked.

Kay nervously, apprehensively raised her hand. "Here!"

"I'm sorry to inform you Kay," he began. Jack suddenly seizing her hand in his expecting some horrible turn of events. "But your partner, Jerry Williams has backed out of the competition. Apparently his manager felt this would ruin rather than help his career."

A smattering of boo's quickly followed. Their host laughed, settling the crowd. "But, we do have some alternates who are thrilled they will now be joining us. Jack Keaton?" he now asked.

Jack felt his stomach roll. "Yes?" he almost squeaked.

"Stacy Burkhoff has also been disqualified. Seems that her husband had no idea she had entered the competition. Apparently she forged her husband's signature stating that he was aware of his wife's participation in the contest. So as such, you'll now be pared with Ms. Dalton."

Jack turned towards Kay with a grin a mile wide, that was, until he saw her face. She was actually frowning.

"What's wrong?" he asked suddenly.

"Competing against you...at the end," she stated. "That's what!"

Jack laughed. "Kay? We've got a long way to go before we ever make it to that point. Why don't we first just play the game, work together, and then deal with that if and when we actually make it that far ok?"

She smiled. "Deal. But Jack? You need to realize something. Regardless of how I'm beginning to feel about you, and yes...excited we're now paired up together. I AM going to win this million dollars!"

"Guess we'll see won't we?" Jack said, and then surprised her as he slipped his hand down between her legs, giving her an affectionate caress.

#

Interestingly, they soon learned that of the ten teams selected, two teams were made up of two guys together, as well as another two teams with two women together. For some reason, Jack hadn't considered that possibility. The remaining six teams were male and female. They were then introduced to their "glued to their sides" cameramen as they were told, for as long as they were actively pursuing their challenges. Handed out the first of their "challenge" envelopes, that would send all ten groups out in differing directions to differing areas. Though everyone would eventually perform or do the same assigned tasks, provided they were of course not eliminated.

"Ok everyone," their host readied them. "You will have exactly eight hours from now to complete your challenges and clock back in here. As you do, you will be informed as to what position you arrived in so that you may return to your homes for some rest prior to returning here tomorrow at this exact same time for your next set of challenges. Ok everyone...get ready? Get set! GO!"

Like bee's, all ten teams tore into their envelopes, then in a near perfect swarm, headed out of the theatre on a dead run.

#

"Where are we going to?" Jack asked, as it had been Kay who had opened, and then read their first challenge.

"The amusement park!" she said laughing. "Oh and Jack? This one say's it's 'YOUR' challenge, and unfortunately for me, the easy one."

He felt slightly relieved as they ran down the street heading towards his car. "So what do I have to do?" he asked her as they headed to their own sides jumping in.

"You get to jerk off while riding the rollercoaster...you know, the one they call Monster?"

"FUCK!" Jack groaned as they headed out onto the highway.

"What?" she asked.

"Well for one...I fucking HATE rollercoaster's. And two...if that's the easy one, can you even begin to imagine what yours is going to be like. And then mine? Tomorrow?"

Kay laughed. "We have to make it through today first Jack," she reminded him. "And don't worry...a rollercoaster's not that bad. They heard the snicker of the cameraman who just like they'd been told would be literally glued to their side. He'd gotten in the back seat and was still filming.

"What are you laughing about?" Jack asked. "I really do hate rollercoaster's. I'm apt to throw up if anything!"

"I hope you do," he told them. "It will make for some interesting entertainment for our closed-circuit audience."

"Fuck me!" Jack groaned once again while Kay laughed.

#

The amusement park was a half hours drive. Kay read carefully through this particular challenges rules and requirements several times. She wanted to make sure they didn't do anything that might cause them to be eliminated.

"It says here, that if you climax before the rides over, then we get an extra hour bonus time knocked off whatever time we check back in!" Kay said excitedly.

"Little good that will do us for this one," Jack responded. "It's a long ride...but not that long for one thing. And for another...I already told you how much I hate rollercoaster's! It'll be tough enough just trying to jack-off while I'm riding the damn thing!"

Kay giggled. "It doesn't say anything anywhere in the rules that we can't get you ready to 'pop' before hand!" she said wickedly. "Nor does it say you have to be the one doing it. So the way I see it, we'll get you nearly there to begin with, then see if we can keep you excited until we get on. With luck, maybe it won't take too much effort, and I'll be the one playing with you the whole time. How's that sound?"

Suddenly, it didn't sound half-bad. "OK," he grinned. "That just might work!"

They hurriedly made their way to the 'Monster', David, their cameraman following closely behind them. As there was a restroom facility close by, Kay had Jack check it. There was only one other guy using the urinal. "Haven't got time to wait," she told him. "Lets go!"

They ran in, ducking into one of the stalls before the lone guy inside was even aware that a woman had entered. As quietly as she could, Kay drew Jack's prick out, surprisingly hard already...and began sucking it.

"Holy shit!" Jack moaned a bit too loudly. "You never said anything about..."

"Shhh!" Kay warned still sucking him. "There's no rules about this either, except for on the rollercoaster."

It didn't take long, Kay apparently was good at nearly everything she did. "OK...I'm pretty fucking close!" he warned gritting his teeth.

"Then lets get to the ride!"

Once again they dashed out of the restroom just as a group of teenage kids entered. "Hot damn!" one of them spoke as Jack and Kay came flying out. Jack didn't dare look down at himself, he knew the front of his pants were tightly stretched over his bulging cock.

"Just stay behind me as close as you can while we stand in line, don't worry...I'll take care of everything!" Kay said excitedly.

And she did. Luckily it wasn't busy, so the line wasn't very long at all. They stood waiting to get into the next car, Jack standing pressed closely behind Kay who nonchalantly stood in front of him, hand down and behind her as she continued petting and stroking his dick keeping it hard and excited beneath his short pants.

When at last it came their turn to board, David climbed into the seat in front of them grinning evilly as he continued filming their adventure. Even before the car began moving, once the attendant had walked by checking that their harnesses were secure, Kay released Jack's prick, immediately stroking it. "You getting all this?" she asked directly into the camera.

All David did was nod his head and smile.

They began the long upward climb towards the first hair-raising drop that would send them racing downwards in a sidewards dive before spinning in the opposite direction through two quick loops, and then what was affectionately known as the 'cork-screw'.

"Oh fuck!" Jack said as they climbed.

"Just relax! Concentrate on what I'm doing, how it feels," Kay said stroking Jack's prick smoothly up and down, up and down. "Just close your eyes...don't even think about the ride, just think about this...think about how good it feels, how nice it feels to have me stroking you, hand-fucking this gorgeous hard cock!"

Jack was barely even aware they'd already toppled over the crest rapidly gaining speed as they tilted sideways into the first of several torturous dives. Keeping his eyes closed just as she'd told him, it was easier. And...the sensation of the cool air rushing past, the feel of it on his exposed cock had an interestingly erotic affect as Kay continued stroking him, pumping his cock furiously now up and down.

"Come for me baby...let this fucker squirt for me. Shoot all that marvelous juice right into my fucking face!" she was literally screaming.

Even David groaned pleasurably hearing that one.

They had made it through nearly three quarters of the ride without Jack's sicking up. And to his surprise, he felt the first bubbly tingle of his orgasm's approach. "Oh fuck! Yeah baby! Now! Now!" he cried out in complete surprise.

Kay was laughing hysterically as the cream from Jack's prick exploded, disappearing almost immediately as they went into a series of vicious twists followed by a complete roll going into the last dive. "You are getting all this yes?" she asked once again.

"Yes!" came the simple reply. "I am!"

Their section of cars came screaming into the station. Jack hurriedly fumbled with his prick putting it away just in the nick of time as the operator's began unlocking the doors allowing their exit. Jack laughed, almost speaking, then closed his mouth as one of the attendants stood, opened their door and froze while looking at Kay as she stood up.

"Enjoy the ride?" he asked suddenly grinning.

"Yes, very much...thank you!" Kay answered, then all but pulled Jack in a hard run down the exit ramp.

"Ah...you'd better take five to go into the women's restroom he told her."

"Why?"

Jack burst out laughing, as did David. "Cause honey...you got a natural cum-part sitting on top of your hair!"

Kay turned towards the cameraman. "I suppose you got that too yes?" And again, he nodded.

#

"Ok, open the second envelope!" Jack pressed, now feeling giddy as well as excited. "What do we do next?"

"Bumper cars!"

"Bumper cars? Fuck Kay...how the hell does this one work?"

"Easy...you drive, I play. Just try not to hit anyone if you can, and stay away from everyone as much as possible!"

The camera guy had already scouted out a location where he could stand and follow their antics inside the ride. "Just make sure you come by me several times so I can film you," he warned. "I need at minimum ten seconds of pussy touching, or you fail this particular challenge."

"Shit...ten seconds in a ride like this is an eternity!" Jack stated.

"Like I said Jack...you got the easy one today!" Kay reminded. "Ok, let's do it!"

She had worn a simple short skirt zippered along one side. Just before climbing into the bumper car they'd been given, she twisted it, bringing the zipper around to in front, unzipping as she did. She looked carefully over towards the ride attendant who at the moment was busily helping someone else climb inside their own car. Close enough, without too much risk, Kay bared her pussy facing towards were David stood filming them. She gave herself several quick strokes through the passage of her quim until Jack spoke forcing her to close her skirt, sitting down.

"He's coming!"

"I should have gotten at least two or three seconds for that bit of pussy play," she said hopefully. "Now...just make sure you drive this fucker as often and as quickly as you can towards David, I'll make sure he gets what he needs as you do!"

When the ride actually began, it was a lot tougher than Jack thought it actually might be. With so many bumper cars slamming into one another, chasing one another around, Jack was forced into taking a series of time-consuming detours before freeing himself from the pack, making a mad long dash along the side.

"We're gonna have to risk it some!" Kay realized, needing to accumulate some time. She'd already prepared herself, flipping her skirt completely open as they ran down along side one stretch of the arena, right past the rides operator. Luckily for them, the girl manning the station took no notice of them as they passed, content to be looking ahead of them where most of the action was taking place. Jack even slowed their car, trying to squeeze as much time in as he could as Kay played, spreading her pussy, fingers furiously working her slit as David stood at the far end in the corner filming, with a welcomed relief 'thumbs up' as they passed.

"You need three more seconds!" he shouted out at them as they screamed by. It wasn't a lot, but they soon found themselves being battered by a group of driver's intent on hitting anyone and everyone.

"Ok, hang on Kay," Jack told her. "I'm putting this fucker into a spin if I can, and when we come out of it...we should be right in front of him, so be ready!"

Jack braked, then yanked hard on the steering wheel just missing another of the cars intent on ramming into them. Sure enough, as they came out of the move they were in front of David's camera once again. Kay had anticipated the move, her skirt once again fully open, pussy clearly displayed as she inserted not one, but two fingers inside herself as they swung by. The feel of power suddenly leaving the vehicles left them coasting a short distance away. Kay quickly re-zipped her skirt, stepping out moments later.

"God...did we do it?" she asked.

Hurriedly they made their way out of the ride over to where David was standing.

"Well?"

He grinned. "Congratulations, you two met both of your challenges. Time to head back!"

#

"Jack and Kay? You're team number three!" Their host said in greeting upon their return. "I'm assuming you'd like to bank the hour you earned for getting Jack to climax during the ride yes?"

"Yes!" they said in unison. "Ok, you two will go out third tomorrow exactly at this time. Congratulations to you both...now go home and get some rest because tomorrow I am sure will prove to be another very interesting day!"

#

They of course arrived well ahead of their appointed time to leave. Watching as the first group, Kit and Preston two of the gay guys headed out first with a little over an hours lead over the second group, and just a bit more times lead over Jack and Kay. They had come in only minutes behind the second group, so they'd be leaving shortly after them.

"Whew...wonder what's in store for us today?" Jack asked nervously. Now down to eight teams with one team failing to accomplish their challenges, and the last one to arrive still being eliminated.

They were soon given their envelope, though unable to open it until their time actually began. The second group quickly headed out, Kay and Jack anxiously counting down the seconds until they could.

"Ok, open it!" Jack yelled. "What's it say?"

"Oh God!" Kay moaned.

"What? What?"

"Baskin Robins!"

"Ice cream?"

"Yeah...ice cream. But wait until you hear what it is we have to do!"

#

With David once again riding along in the backseat, they drove towards the closest Baskin Robins they could find. Kay had read, and then re-read the challenge carefully, making sure she understood exactly what was required of them.

"Shit...and this is the easy one?" he whistled. "God...can you imagine what mines gonna be like then?" he added worriedly.

"Yeah...and this one could really kill us on time too. A lot depends on how busy they are, how much privacy we may or may not have in order to pull this one off. And besides...it's gonna be cold too!" she said already feeling a shiver just thinking about it.

"So...it really does say we have to make you into a banana split huh?"

"Yep! Complete with a cherry on top!" she added. "And then...and then...I have to play with myself using all the ice-cream, whipped cream and toppings for five full seconds!"

"Not to mention the banana," David spoke from the back seat.

"You would have to mention the banana!" Kay said shooting him a look.

Jack laughed..."Focus Kay, focus. Remember? We'll just need to time it, hope for a little luck, and turn you into a deliciously sweet desert as quickly as we can, and move on to mine."

"Focus Jack, focus," Kay said as Jack's thoughts suddenly turned to horror.

#

They had placed their order noticing the puzzled look on the clerk's face who stood there serving them.

"We like to make it ourselves," Jack lamely told her. "And we're happy to pay extra for it that way," he added. "A scoop of vanilla, a scoop of chocolate, a cup of whipped cream, and a cherry."

"Don't forget the banana," Kay giggled actually blushing, which in turn made the clerk behind the counter stare even harder at the two of them.

"Yes, one firm hard banana," he added as Kay reached over to pinch him.

Minutes later they walked outside taking one of the available tables. And though it wasn't all that busy, it was just busy enough that there was no way possible they could turn Kay's pussy into a banana split without being seen.

"Fuck! The ice creams beginning to melt too!" Jack said nervously. "If and when..."

"Not IF Jack...but when yes," Kay interjected.

"Ok, when we finally manage to do this, you're gonna be a mess!"

They sat for the better part of an hour, several times just about to attempt their decadent little desert when someone would either come, or leave, keeping them from doing it. "You sure it says that?"

"I'm sure. I read the rules a number of times already," Kay informed him. "It specifically says we have to make me into a banana split at one of the establishments table areas."

Many Feathers
Many Feathers
10,479 Followers