Third Time's the Charm?

"Gnnngh!" You groan as you get your rocks off a second time, your second load coating the sticky skin where your first had barely begun to dry.

"Oh no!" Elsie could not help but laugh, you really couldn't blame her. Thank God it wasn't Fiona you were doing this with. The laughter would be cruel and the comments malicious. At least with El the laughter was light and full of good humor.

As you come out the other side of your climax you let out a great gasp. "Ohhhh god damn! Sorry."

"You don't need to apologize." Elsie titters. "But you do need to stroke. No stopping, remember?"

"But..."

"You agreed. Double or nothing."

"But..."

"Come on now, don't you stop. Game's not over yet."

"But..."

"You didn't lie to me...did you Jesse?" Elsie looks deep into your eyes. "You wouldn't lie to me, would you?"

"Fuck." You grunt.

You start to stroke once more. If you thought the first refractory period was hell it was nothing compared to now. Your dick is screaming at you to leave it alone but you were a man of your word, especially as it related to El.

A double beat section starts and goes on...and on...and on. Your penis is shrinking even as you tug to the quick pace. After what seemed like forever the two money shots happen and that wonderful bell telling you the round had ended.

"God damn." You look down and try to shake your rapidly softening manhood to life.

"He he he."

"How are you...doing this?" You say. "You didn't last this long the first time?"

She shrugs. "I was pretty horny that day, plus it was pretty exciting that you were joining us." She points to the screen. "You must like these women."

"Yeah, they're hot."

"You like women like them?"

"Yeah. sure."

"Jesse...do you like women like...us? Like me and Fiona and the others?" She lets out a forlorn sigh. "It wasn't our choice you know. We didn't ask to be like this."

You reach over and rest your hand on her arm, accidentally getting some cum on her in the process though she doesn't seem to notice. "El, you're beautiful. You are all beautiful."

"You too Jesse." She says softly. You share a moment of connection before she chuckles and motions toward the screen. "Okay Mr Floppy." She then says to your dick. "Wakey wakey little guy, we're about to start again." There is a brief pause before her eyes go wide. "I mean...not little guy...I didn't mean to say that...I meant normal guy...I mean...ohhh, I'm sorry."

You roll your eyes and laugh it off. For this family yours was a little guy.

The fourth and final round is brutal. The pornographic sights, the lewd sounds, the relentless stretches of stroking. There are no breaks and few pauses of that knock, knock, knock, knock of the stroking beat. Now Elsie is feeling it. Her eyes are intense, a subtle sheen of sweat visible across her skin, her cheeks flushed with blood, and her massive schlong flexing to its maximum rock hard arousal. You couldn't wait to see her cum.

Miraculously, after a agonizing period of shrinkage and softening where jerking your shrunken flaccid dick was like tugging on a deflated balloon, your own dick rises once more to your constant attentions. You are chafed and sore, your balls aching like you'd never felt, but like a phoenix rising from the ashes you were up again.

Elsie glances over. "You're hard again!? Wow."

You pretend as if you'd been expecting it. "What, you guys can't recover so quickly?"

She lets out a breathy laugh. "Chloe can, Chloe can always get hard. But she's small like y...um...she's smaller than us."

Your cousin Chloe, the previous runt of the Bailey litter, had at least an inch on you from what you'd gathered from Fiona's teasing.

"I don't think it's a size thing." You reply as both of you continue to jerk in perfect unison. If synchronized fapping were an Olympic event you and Elsie would make a great pair. "Hey, triple or nothing? Third time's the charm."

"You're joking." She huffs. "That's not fair. You've nut twice already."

"Come on." You plead.

"But..."

"Afraid?"

"But..."

"Gimme another chance El."

"But..."

"Please?" You give her a bit of her own medicine with a sweet voice and batting eyes. She lets out a sigh and you knew you had her. "And let's raise the stakes. Not only do we have to dress up like the other wants for two days, the loser also has to do whatever the winner says."

This interests her. "Like a human doll?" She asks.

"A doll?" You hadn't thought about it that way, but it was pretty accurate. "Uh, yeah. Sure."

She lets out a giggle. "Yes! You're on!" Blinking her eyes and clenching her jaw she focuses on the video and strokes with extra urgency. You follow her lead. "Three days, dress up and do what the winner says."

Having Elsie as your own personal plaything for three glorious days!? Even if you decide in the end to not cross the line into ultimate taboo the fun you could have was endless. How could you say no?

"Deal!"

You couldn't believe that worked! It was like Elsie was trying to lose. Going triple or nothing this late in the game was sheer overconfidence on her part. With how flustered she was looking and the fact you were drained this would be like taking candy from a baby.

Although...even through the ache and discomfort...this was starting to feel good again. And man those big asses and bouncing tits looked hot. And the moans of the women were just wonderful. And holy hell the beat was absolutely unrelenting.

You are on a long stretch of double fast beats when you feel the surge once again. It is the strangest combination of anguish and delight. Your aching nuts beg for mercy even as they ready themselves to unload whatever you had left in the tank. There wasn't much longer to go though. Despite it all, if nothing changed, you knew you could do this.

Except something did change.

As the pair of you enter the final few minutes Elsie begins to make cute little mewling moans of bliss. "Ohhh...ohhhh...ohhh god Jesse."

You try to block her out. You could not lose three times in one go, you just couldn't. This was your little sister for fuck sake! She looked up to you.

"Ohhhh Jesse. I'm gonna cum so hard. Ohhh my god. Mmmmm...ahhhhhh...ohhhhhh!" Her voice is a loud breathy whisper. Arching her back she thrusts her ample bosom up and out. She brings of her soft shapely legs up onto the counter and you see her pointed toes curl from the joy she was feeling. "Ohhh god brother...ohhhh god it feels so good!" All the while the pair of you stroke and stroke and stroke to the merciless beat. Both of you writhing to the building lust. "Ohhh Jesse! Ohhh Jesse! Ohhhhhhhhh Jesse!!! I'm gonna cummmm!"

It was too much. Just as the video says "get ready to cum!" you are already doing just that.

"Guhhhhhhh!" You growl in agony and rapture as you shoot your meager dregs onto the two loads that had come before. With each small explosion of pleasure comes a deep throbbing ache from your balls. "Fuuuck...fuuuck...ahhhhh!"

You realize you'd been had as El's erotic mewls and moans cease the moment you cum and she continues stroking strong and fast. She is clearly on the edge but not nearly as close as she had pretended. Elsie is far too wrapped up in seeing out the video to pay you much mind as you groan and grimace through the most painful nut of your life.

Cum shots galore fill the screen. Pussy, ass, a facial. And the beat just keeps going.

And then, even as the video wraps up and at last tells the viewer to cum, El clenches her teeth and flexes her muscles and holds out to the bitter end.

The beat ends, the video ends, the race ends. Your little sister lets out a great gasp and lets go of her towering twitching triumphant cock to let it stand proud in victory even as yours shrivels at record speed in your hand.

"I win!" She says out of breath. "I win, I finally win! Three times no less! He he he he he!"