M is for Masturbate

Jack thought. "Doesn't say anything else huh?"

"Nope...just that."

"I have an idea," Jack said suddenly standing up. "Here, grab your end and come with me." They stood as she and Jack walked the table around to the side of the building. "Nothing in the rules say we can't do this," he told her.

David stood filming the entire time.

"Ok, now hurry!" Jack exclaimed as Kay removed her skirt, lying crossways along the table as Jack hurriedly turned her pussy into a banana split. "Go baby go!" he almost yelled as Kay began rubbing, smearing, and using the banana to masturbate with.

"Time!" David called out informing them of their success.

Kay jumped off the table just seconds before anyone came outside. Sitting down, still unable to dress, she sat as though waiting as Jack stood in front of her, blocking the view of the driver who then slipped behind the wheel of his car, finally driving away.

"Whew! That was close!"

"No shit!" Kay said throwing her skirt back on without even bothering to clean up until she had.

"Now what?" They opened the second envelope. Kay laughed.

"Fuck!" Jack said before hearing it.

"We go horseback riding, bare back!" Kay stated. "This should be interesting!"

They quickly drove to the stables where they had a standing reservation waiting for them.

"You an experienced rider Jack?" Kay asked.

"Ridden some...but never...naked," he said re-reading the rules. "You sure this is what they meant by bare-back huh?"

"Yep...says right here, you have to ride naked...and masturbate as you do for a minimum of ten minutes, or until you cum at least."

"What about you?" he asked.

"Doesn't say anything about me," she said reading once again. "You think they'd let us ride the same horse together?" he asked hopefully.

"Hmmm, I don't know...maybe. Why?"

"It might help," Jack grinned. "You sitting behind me?"

"Naked too? You know it doesn't say anything about me having to do that."

"I know."

"Ok," she grinned. "Least we can do is ask!"

It took some convincing, but eventually the owner agreed to let the two of them go out together on the same horse, especially as they wouldn't be going for very long, or for very far. In addition, Jack had paid the guy an extra hundred, the one he'd gotten for just taking his clothes off during additions for allowing them to even do that.

David followed along on his own horse, camera in hand filming everything.

As soon as they'd ridden out of sight of the ranch, he and Kay quickly stripped off the few clothes they were wearing, handing them to David for safekeeping. Remounting their horse, Jack sat in front holding the reins with Kay sitting behind, holding onto him.

She began stroking his hard thick cock slowly up and down in perfect tempo with the slow easy gate of their horse.

"Damn...this ain't half bad," he stated as Kay continued stroking, playing and working his penis. "Not bad at all!" he said smiling.

"Ah Jack? Before you get too lost in this, we're on a time clock, remember?"

"Oh...yeah," he said sheepishly. "Ok baby, giddy up!"

They went about a mile further before turning their horses around heading back, Jack was beginning to feel the "tingly" as he called it, Kay's hands expertly milking him as they rode, though the press of her nice firm tits against his back was certainly helping.

"Shit...you know what?" Kay said.

"What?" Jack just managed teetering on the edge now.

"I think I'm gonna cum too!" she said in surprise. "Think you can make this horse bounce just a little more for me?"

Jack put the horse onto an even brisker gallop, just as he felt the semen fly from the head of his prick as David rode along side, smiling filming giving each of them a congratulatory thumbs up.

#

"Jack and Kay? You're team number six!" They were informed.

"Shit!" Jack exclaimed. "The damn ice cream really hurt us!"

"Yeah, but we're still in it honey, and tomorrows another day. We'll do better, now come on, lets go back to my place. There's another horse I'd like to ride."

#

It was now down to just three teams. Jack and Kay had made up considerable time with yesterdays challenge, one that was easier for both of them. They'd had to drive thirty miles in a rented pickup. Jack drove on the way down, with Kay sitting in the open back of the truck itself masturbating. Disallowed from going over the speed limit, a number of cars passed, many of which had no clue as to what she was doing, though curious perhaps as to why she was sitting back there instead of up front with Jack. It was the eighteen-wheelers that passed that provided her the most difficulty, though she continued masturbating as David sat in the back with her filming the entire thing. On this one, she not only had to climax, but she had to show she was able, and could squirt when doing it. To Jack's delight, she managed to do just that.

"Ok baby...my turn to drive," she informed him. "And your turn to jerk off for the camera."

Though Jack had found it difficult, having to cover up repeatedly as one car after another passed them, eventually he managed to climax before reaching the turn-off as well as the deadline for successfully achieving their challenge.

#

"Just one more day," Kay told him that night as they snuggled up in bed together.

"And just two other teams to worry about now too!" he added.

Though both of the gay teams had been eliminated, they were still up against one of the women's teams, and another young couple who'd pretty well dominated the last couple of days, arriving in first both times.

"We're going to have to find a way to beat them!" Kay said. "No matter what challenges we face tomorrow Jack, it has to be balls out! Literally!" she added. "I've no intention of losing this thing, not now. Not when we're this close!"

"All we can do is give it every thing we've got baby. And I promise you...for you, I will!"

#

"Sky diving?" Jack stammered. "You've got to be kidding me! Skydiving? And these guys who'll be taking us tandem with them are in on it? Seriously?"

"Money goes along way Jack," Kay told him. "And the fact that all three teams are doing this one together as the final challenge makes it all the more difficult. Bottom line is this, we jump out naked from an airplane for one. Two, we masturbate during a free-fall for another...third, anyone climaxing before hitting the ground receives bonus time. And right now, we need all the extra time we can get jack!" Kay said worriedly. "We're still behind almost an hour! So...unless one, or both of us manages to cum before landing, chances are, we'll lose. Like I said yesterday sweetie, this one really is balls out this time!"

"Fuck...you can say that again," he told her.

#

Wearing their own head-cameras this time, it was up to each of them to record their activities, especially if able to reach and achieve orgasm before landing. Jack was at least grateful for the fact that his 'buddy' was a female, who'd be in charge of the free-fall, opening the chute, and the emergency chute if necessary, which Jack didn't even want to think about. But the thought of being able to so openly masturbate while doing so truly had him bothered. Rollercoaster's had been bad enough. But now this!

All three teams took off in the same plane together. All naked, all seemingly anxious as they waited their respective turns to jump. Thankfully, Jack discovered this was everyone's first time jumping, so no one had an edge there. But whether they would somehow pull off this final stunt and emerge victorious was a whole different matter altogether!

"Jack?" Kay said gathering his attention towards her and off his very limp flaccid looking cock.

"Yeah?"

"Do what you did on the rollercoaster, just don't think about it, don't even look if you don't want to. But make sure...whatever you do, that camera has to film you jerking off...and more importantly, cumming too if you can manage it. It's important Jack, you need to climax, it might be our only chance!"

"You actually think you'll be able to do it in that amount of time?" he asked seriously.

Kay smiled. "Honey...that may be the only advantage on this one that we do have. I'm so fucking wet now just thinking about jumping like this!"

Jack actually laughed. "Only you could get turned on thinking about jumping out of an airplane, and squirting your pussy juice all over the ground somewhere below you while doing it," he told her.

"That and for a million dollars! Remember?"

He was surprised when the thought of that actually started to make his dick hard.

Jack stood in the door of the airplane with dick in hand already stroking it. According to the rules, as soon as they were allowed to stand there just prior to jumping, they could begin. As odd as it felt to be attached to a fully clothed woman while he himself was naked, sporting an erection, it was nothing in comparison to the overwhelming fear he had as he stood looking at the ground below that seemed to be absurdly far away for one. And for another, that he was going to somehow have to find a way to actually climax before landing if they were to have any chance of winning this thing at all. All he wanted to do at the moment was throw up, and that was a long ways from cumming.

Kay and her instructor stood behind, she too already fingering her pussy, though unlike Jack, seemingly enjoying it as she furiously worked her clit much to the delight of the onboard camera crew.

Jack heard the warning buzzer. "Five seconds!" his diving companion warned. "Four...Three...Two...GO!"

Jack leapt into nothingness, and for a moment thought he was going to throw up, that or black out. Fear seized him momentarily, panic taking over. Then he heard Kay's words inside his head. "Focus Jack...focus. Remember, you're jerking off for a million bucks!"

And so he did.

Amazingly, after the reasonably short free-fall, as soon as he felt the chute finally open, and their horrifyingly quick descent finally slow, he found himself actually enjoying the sensation. And with it, his erection suddenly growing stiffer, harder in his hands as he began masturbating with renewed determination. He was also very careful to ensure his head-camera was indeed filming himself as he did, which he could see through the tiny monitor that half-wrapped around the side of his helmet so he could see what the camera was seeing.

He took a quick brief look around, spotting Kay just above and off to the right. It was a deliciously amazing sight when he did. There she was, suspended mid-air, legs spread, hands busily working between her legs.

"Focus Jack, Focus," he told himself as he looked towards her, smiling. And felt the first delicious tingle of orgasms approach.

#

Stepping up to their host after landing, they stood waiting patiently to hear if they'd succeeded or not.

"Kay and Jack?" I regret to inform you, you've finished second," he announced.

Jack felt himself go limp, knew without even turning to look at her what Kay must be feeling.

"However..." their host added, now suddenly smiling. "Both you as well as Kay managed to climax before landing. Neither of the other two teams were able to accomplish that. And because of that...with the added bonus time allowed, that places the two of you into first place! Congratulations! You will now go against one another for the million dollar prize!"

#

He and Kay stood hugging one another joyously. "When?" Jack finally asked after a few moments of congratulating one another.

"Two hours from now," their host informed them. "Back on stage where this all began. Just the two of you in front of a jam-packed audience! How's that sound?"

"Fuck!" Jack moaned as he heard Kay burst out giggling.

#

Two hours later they were sitting on stage though upon a very large, very comfortable couch...nude.

The theatre was packed. They'd both been given a set of instructions with very specific details regarding their final challenge. They were to sit side by side, masturbating one another. The first one to climax would be of course...the loser. At no time could either one remove a hand from the other. As long as a hand was on the other persons body at all times, it didn't matter where it was. As long as at least one hand was on at all times. A tricky condition to be sure, but even more problematic for Jack, though certainly not a premature ejaculator, he seriously doubted he had the same kind of willpower and determination that Kay had. Especially when what it all boiled down to was a million dollars!

"Ok...regardless how long it takes, the two of you will remain here until one of you reaches orgasm? Understood?"

"Yes!" Both Jack and Kay answered.

"Good luck to you both then. And so...for a million dollars Jack and Kay...start masturbating!"

At least they weren't total strangers, or Jack would have been at an even bigger disadvantage than he felt he already was. He at least knew a few of Kay's 'sweet-spots' things she liked, how she liked being touched. And so he began to use those. But likewise, Kay also knew him pretty well too. Unlike as many might expect, she didn't just simply start jerking his cock up and down rapidly. That...he could take. For some reason, too much of that and he could be come numb, losing sensation. No...Kay knew him well enough to know that he liked it, preferred it actually when she stroked him softly...slowly at first.

And so she did.

But just as she knew his weaknesses, wants...he too knew a few of hers as well. He knew Kay loved having her nipples toyed with, especially as he merely petted, stroked her fur-lined pussy rather than assaulting it, or even making any attempt to directly touch her clit. No...like he, she found the pathway to orgasms approach far sweeter, far more intense, and actually quicker when Jack aroused her beyond the point of being able to withstand it any more.

"You fucker," she moaned half seriously. "You know how much I like that," she hissed as Jack twiddled her hard extended nipple, his fingers spreading into a 'V' as he continued strumming her passage without quite entering, enclosing his fingers briefly though frequently around her blood engorged clit.

But though Jack felt some encouragement at her audible sigh of pleasure, she too was driving his arousal constantly upwards. Capturing the head of his prick between her index and middle finger, she used her thumb to gently circle the tip, all the while holding him, this way, softly squeezing, until finally coaxing the first pearly drop of arousal from the head of his penis.

From overhead, camera's panned in for close-ups, providing the audience with an even greater view than what they were seeing. Audible gasps, groans and even whispered murmurings could be heard as the excitement began to build throughout the entire theatre, and not just on stage.

"You like the way I stroke your cock don't you baby?" she suddenly spoke. "You like the way I play with it...making it feel good, making it all slippery, wanting to cum for me, to spurt all that hot delicious juice all over me, all over my face, my tits and especially my pussy!"

Groans and moans could be heard all over the audience. Obviously the words now being spoken were just as easily heard as the decadent close-ups now revealed as they continued torturing one another with their hands.

"Yeah I do," Jack said catching her off guard momentarily. "But you also like the way I'm petting your pussy, that precious little clit just begging for me to suck it, to lick it...to hold it between my lips while my fingers stroke inside you, fingering you just like this!"

A deep groan escaped Kay's lips, her head momentarily tossed back as Jack's fingers finally entered her for the first time, his middle finger now crooked inside her, the pleasure spot now directly stroked, the palm of his hand riding up high enough to gently graze her clitoris simultaneously as his fingers worked their magic on her aroused flesh.

He felt her thumb suddenly increase tempo, the ridge of his prick just beneath the head suddenly being strummed like the strings of a guitar.

"Oh fuck," he allowed without thinking. Somehow gathering the willpower as she continued to tease the supersensitive head of his prick. "Oh you beautiful cunt you, yeah that feels good...your hand on my cock feels damn good, but so does my finger inside you pussy...and now, inside your ass!"

Kay was as liquid as it was possible for her to be. Rivulets of her female cum-cream ran in tiny streams from her pussy lips, soaking his fingers which he now began using to encircle the tiny bud of her ass, coating it, lubricating it before easing just the tip of one finger inside.

Jack felt her free hand suddenly cup his tight balls, kneading them like bread, stroking them gently, now urging the desire that began to tingle deep within the depths of his soul.

"Cum for me baby," she purred, cum hard for me. Splash all that hot sticky cum all over my face!"

Jack spotted more than one couple in the audience who where now openly masturbating themselves, or in many cases one another. Even that vision hurt rather than helped as he quickly averted his eyes partially closing them. He could feel his climax approach, knew the warning signs that would soon have him arriving at the point of no return. He had one last card to play, or all was lost, and he knew it. It might surprise some...probably most, but it was something he'd inadvertently discovered during one of their nights together.

Still keeping one hand upon her breast, her nipple gingerly caressed as he continued to lightly thumb it, encircling it, he removed his finger from her pussy, lifting it upwards and then placing it upon her own lips. There he began smearing the fragrance of her femininity, her own want, need and desire. She sucked his finger in as though attempting to keep it there, disallowing him from doing that again. But he did. Again, his hand down between her legs, now directly stroking her clit in deliciously slow circles, a quick slip of his finger inside her, then up again once more to spread the coating of her lubrications around and upon her lips. He felt her body shake uncontrollably, felt it tense, felt as well as heard her as she reached nearer and nearer the edge of ecstasy and bliss that she fought so hard now to keep from reaching.

Just as he was.

Too little too late perhaps, as the first sign of his surrender began to manifest itself. Trying to stave off the explosion, no longer possible. Grimacing in near pain as he felt his cock suddenly strain, suddenly expand...the first jettison of his spunk already building to explode from the tip of his cock.

Kay, removed her hand and then came. Jack spun towards her in shocked surprise, even as his prick lurched, the first hard-felt jettison of his cream skyrocketing into the air. Kay's hand once again upon him, now jacking him softly, slowly...purposefully just as he liked, just as he loved and enjoyed. Kay, her hand now holding his against her, gyrating obscenely as her pussy exploded, the fine misty spray of her joy covering his hand, coating it as she cried out deliriously, her eyes now locked with his as she came, came looking at him, came as he continued looking at her.

Nothing else mattered, nothing else existed. For a moment, all that was, was them.

"Congratulations Jack, you're the winner of one million dollars!" he heard moments later after both of them were given time to recover their senses, slowly gradually as had many within the audience also needed to do.

"Why Kay why?" he asked. "You had me! You KNOW you had me!" he questioned her.

"Because I realized...I wanted, needed you more than I needed a million dollars," she told him. "I wanted you to know, just how much you mean to me."

#

"Kay? Jack?" A voice suddenly came from somewhere over a nearby loud speaker. "This is Robert K. Preston speaking. I want to thank you both for your erotically powerful efforts. You have certainly fulfilled my wildest expectations and enjoyment during this competition. And just to prove how much I do appreciate it, I am happy to inform you, that you are 'both' winners of the grand prize of One Million Dollars!"