A Spin of the Wheel
Nicoya is given a chance, a random chance, to perhaps get out of chastity and even receive some extra rewards. As with all games of chance however, there's always a catch. :D
This story was written for Nicoya as part of my themed patreon request day for March. The theme was "Getting Lucky". It contains M/F sex between consenting adults and chastity play. :3
A Spin of the Wheel
Nicoya trembled as he prepared to spin the wheel. He knew the rules, and they terrified him. The idea of leaving this to luck had sounded so fun when Cayes first suggested it, but now that he was actually here once again, he felt like ever having agreed to this was ridiculous.
The rules were simple. One spin of the wheel, and the outcome was binding. There were many different variations, but they all boiled down to three options. First and most numerous were a number of different lengths of time, from a single day to a number of weeks. Second, less numerous but still common enough to provide Nicoya with a glimmer of hope, were another set of numbers that offered orgasms as a prize. As few as one of course, but as many as a dozen. And finally of course, on two single segments of this vast wheel, was the holy grail. Freedom.
That was what Nicoya sought. Freedom from the chastity device in which he had been bound for almost a month now, with three different spins of the wheel only having added to that time thus. Hence the winged feline's terror. He didn't know what would happen if now, at the end of that month which had started out as only a week, he ended up adding another fortnight or even longer to his imprisonment.
"Come on, Nico. Spin, or shall we just assume you want to add another week, and come back to it then?"
Close by Cayes sat and watched Nico trembling before the wheel, both their bodies bare except for the silver cage wrapped around the male's member, his balls hanging swollen and firm beneath. He whimpered loudly at her suggestion, shook his head, and urgently stepped closer still to the wheel. He placed one shaking hand upon its side, then another, and without even a moment more of hesitation gave it an almighty spin.
The cat stepped back, and Cayes beckoned him over to sit upon her laps as they watched the wheel spin, listening to the metal arrow at its peak rattling as each spoked segment passed by in a blur at first, then slower... slower....
It passed by Freedom. Nicoya groaned in dismay.
It passed by another Fortnight of imprisonment, Cayes giggled as she felt Nico tense, then relax with a whimper of relief.
It passed by a day.
A week.
Seven orgasms.
Another two days imprisonment.
And then...
It stopped.
Nicoya gave a whimper of stunned wonder, and Cayes giggled as she cuddled the winged feline against her own bare body.
"One orgasm. Lucky you, Nico."
The cat looked at his mistress in joyous gratitude, flinging his arms around her neck and beginning to lavishly apply a series of tender kisses all over her face, whimpering under his breath all the while.
"O-oh gosh... oh god, I... I get to cum. Oh, Mistress. Thank you. Thank you."
After a short while of indulging Nicoya's kisses and even returning a couple of them however, Cayes gently scooted Nico up and off her lap. She rose to her own feet before him in fact, and looked him up and down, eyes settling on his chastity cage before too long. He followed her gaze with a longing whimper, and boldly thrust out his hips, eyes wide and expectant.
"A-are you going to let me loose right now, Mistress?"
Cayes' eyes sparkled. A smile curled at the edges of the turtle's beak-like muzzle, and she raised a playful eyebrow.
"Let you loose?"
Nicoya nodded, still full of enthusiasm.
"Yeah. Y'know. Take off the belt so I can cum."
Cayes' grin grew wider, and little by little as Nicoya saw the way she was beaming at him, his smile faltered. He whimpered, then groaned as his own eyes widened in realisation.
"Oh. O-oh... god..."
The turtle smirked, and even as she took the cat by the hand and began to lead him towards their bedroom, she spoke the truth that he had just come to realise.
"At no point did the rules say you get to take the belt off, have an orgasm, then put it back on, Nico. The only way to get the belt off is to hit a 'Freedom' spot on the wheel."
Following obediently along behind his mistress, Nicoya moaned in dismay.
"B-but... then, how am I supposed to cum? Like, really, properly cum?"
Not turning, not looking her beloved pet in the face, Cayes' beaming smile lit up the entirety of her face with absolute glee.
"Oh... don't worry about that, kitten. I have some ideas."
**********
"_Ah. Ahhh _! C-Cayes... yes..."
Thirty minutes later Nicoya lay face down upon his mistress' bed, a thick body pillow emblazoned with a naked photograph of his own body pinned beneath him as he humped mindlessly against it. Above him meanwhile, pinning him between pillow and her own smooth body, Cayes grunted while she plunged the length of her favourite double ended strap-on deep into the winged cat's rump. Her own crotch was already soaking wet and dripping visibly even now, three orgasms in with no sign or intention of letting up yet. Each thrust drew yet another savage, pleasure stricken grunt from her beak as the turtle pounded at her pet's prostate, but not nearly as loud or lewd in their exclamations as those to escape Nicoya himself.
The cat wailed over and over again as his prostate was given the most intense workout he had experienced in months, Cayes' thrusts so pinpoint accurate that not a single stroke of the dildo buried inside his ass went by without that sweet spot being not just teased, but stimulated to the absolute extreme. Already Nicoya could feel cum gushing from his cock, pouring out through the metal cage locking it down and keeping it from growing or indeed being stimulated by the outside world, but the prostate stimulation draining his balls wasn't enough. He hadn't been promised a milking. He hadn't been promised being drained without the pleasure or the release he craved. He had been promised an orgasm, and he wouldn't let his body give out until he had gotten it.
Thus he humped at the pillow beneath him, clutched and clawed at it in a frenzy as he made rough and wild love to it regardless of the device locking his cock down. He had to try. He had to make his body believe that he really was fucking this pillow, and thus hoping that in combination with the prostate stimulation surging through him with each passing second he would be able to trick himself into toppling over the edge. And, much to the cat's wonder and surprise, it felt like it was working. He might not have been hard. He might not have been free, but he could feel the pleasure building. Slowly but surely he could feel the arousal surging through him building towards that deliciously familiar critical mass.
"I... o-ohh... ohhhh C-Cayes... I'm... mmh-hhhaaaahh..."
Another echoing cry escaped the turtle mere seconds after Nicoya moaned to her, and once again he felt her own juices splashing out against his backside as his denial granted her a fourth orgasm of this one session. For a short while her thrusts grew unpredictable and more wild in their motion, and even when she recovered even a portion of her sanity, they remained even more fierce and frantic than before as she moaned to him.
"You're gonna do it. For me, Nico. You're gonna get so hot, so horny... even being locked away in chastity won't keep you from cumming for me."
And thought it took another five minutes, another five minutes of passionate thrusting, of wild humping, another shrieking orgasm from the turtle riding her male lover's ass so hard and so deep, Cayes proved herself right in that commanding proclamation.
Nicoya's eyes bulged even as they glazed over. His wings flared and flapped where they lay trapped between his and Cayes' bodies, and a frantic, mewling wail that rang out in a single breath for the entirety of his orgasm's duration poured from the cat's muzzle as he climaxed. He felt hot ribbons of cum lashing out from his trapped, flaccid cock, he felt his member's flesh throbbing against the inside of its dome-line cage, the squeezing of the metal around him almost more pleasurable in its own right than it was any form of discomfort in those moments. He felt his prostate still being hammered even as his ass clenched tight around the invading dildo, and he felt Cayes' ragged breath in one ear, his mistress whispering to him in a giddy frenzy of her own.
"O-oh god... Nico. You're... you're doing it. My kitten. I love you. I... o-ohh... god..."
And then it was over.
Nicoya sank down against the sticky, sweaty pillow bearing his own likeness, groaning in the kind of relief and satisfaction that he hadn't felt for more than a month. He purred as Cayes' weight remained lying over him, and the turtle's dildo remained buried but now almost motionless in his ass.
Less than a minute later though the winged cat's peace and calm was shattered once more though, by one final whisper from Cayes before she slipped into her own multi-orgasmic, utterly exhausted slumber right there atop him.
"I... mmh... I hope, w-when you spin the wheel again tomorrow... you get even luckier."
Nicoya's eyes widened anew.
"W-wait. Tomorrow? You mean... a-and, if I roll more orgasms... I... we might have to do all this more than once?"
From where she lay astride the cat's fatigued and yet still trembling body however, Cayes simply began to snore. For if indeed Nicoya did spin luckily once again, and if this time around more than one orgasm was required, she would need all her strength and stamina to ensure that she could make it happen for her beloved pet.
By Jeeves
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