The Gambler: Chapter 5 (Patreon)

Heyyo! Thank you to everyone from the Interactive Story Club for helping to put together another amazing chapter. Make sure to vote in this week's poll and don’t forget to comment if you have any additional ideas for chapter three and beyond! I hope you enjoy!

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With greedy eyes, Clara scanned over the large variety of sex toys she had at her disposal. It took every ounce of restraint not to go nuts and choose several. As much as she wanted to melt Blake’s brain, she didn’t want to have him fizzle out in the first hour. She needed to slowly ramp up her total domination of him before shoving him in at the deep end.

Looking back at Blake, Clara savored the meek and terrified expression on his face. For years, this man had possessed a poker face unrivaled by any other player in the circuit. Not a trace of that stone wall countenance could be seen now as his anxiety was on full display.

That alone nearly pushed Clara to expand her selection to two options as she was caught between granting him humiliation pleasuring on his front side and invading his most private hole on his backside. After some simple breathing exercises, she calmed herself down enough to settle back on only choosing one. With her head-clearing, she could see her choice solidifying in her mind. Guaranteeing an orgasm with a vibrator or cock ring nestled into his cock may have had its perks, but the idea of watching him lose control from having his prostate stimulated was too good to pass up. Waving her hand over the wide selection of butt plugs and anal vibrators, one of them seemed to catch her eye more than any other. She walked over to Darla and whispered something into her ear, which caused the Auction House employee to giggle uncontrollably.

Still prone atop the changing table with his giblets exposed, Blake did not like the sound of Darla’s laugh, nor did he think Clara’s telling smirk meant anything good was on the horizon. Sadly, only looking at the crowd around him told him that any hope of running away was out of the question. He’d have to endure whatever cards Clara had up her sleeve.

Returning to the sex toy table, Clara eagerly grabbed a long, black rod with a silicone tube attached to another small bulb at the end. Blake didn’t know what the tube or second bulb were supposed to do, but what he did know was that the device Clara was holding was most definitely a butt plug. If he wasn’t sweating before, he certainly was now. “W-What is that thing?” he asked, causing uproarious laughter to fill the massive changing room. He couldn’t help but blush, feeling incredibly small to be the center of attention for such an embarrassing ordeal.

“This, my sweet, subby boy, is an inflatable butt plug,” said Clara, giving the smaller bulb a big squeeze and allowing for the rod to grow slightly bigger in its center. Snickering, she gave it a few more presses, turning the shaft-like sex toy into a bulbous ball.

All the while, Blake’s eyes grew wider to accommodate the inflatable toys increasing girth. “You c-can’t be serious!” he shouted, attempting to hop off of the changing table. He didn’t care if his odds of escape were slim, he’d never had so much as a pinky shoved up his ass before and he didn’t intend to change that now.

Unfortunately, Darla had already anticipated such a reaction. She’d positioned herself behind the table so that the moment he tried to scramble, she was right there to grab him by the arms and flatten him on his back. “Clara, I’m afraid you’re going to want to place those ankle restraints on him,” she said, gesturing to the two cuffs hanging off the far side of the changing table, “There is zero chance an anal virgin like him is going to let this happen willingly.”

Anal virgin. The term echoed across the standing audience, causing several gasps and chuckles to sound off. The already excited onlookers began to salivate at the prospect of watching not only Blake’s first diaper change through to its completion but also witnessing the moment that his rectal cherry was popped.

Placing her fingers on the release valve, Clara returned the inflatable plug to its smallest size before sitting it down near the changing table. She then took the first leg cuff and wrapped it around Blake’s ankle, allowing the velcro strips to conjoin. Repeating the same process with his other ankle, she had him fully in her clutches.

Blake’s legs bounced back and forth as he wiggled to free his feet from the shackles that bound him. Alas, no amount of kicking or quick movements were able to apply enough force to get the velcro to budge in the slightest. With no options left, he swallowed his pride. “C-Clara,” he said, his eyes starting to water, “You w-win. P-Please, call the bet off.”

“You’re right, I do win,” said Clara, slapping her hand on his knee and prying his left leg open. She left no room for misinterpretation when it came to her intentions. She was going to introduce him to a whole new world of pleasure, whether he liked it or not.

Blake attempted to shutter his legs, but he wasn’t flexible enough to bend that far. With escape and persuasion no longer options, all he could do now was close his eyes and wait for the inevitable. In a last-ditch effort, he puckered his butthole as tightly as he could, hoping that his uninitiated anus would be too small and tough for her to push the toy in.

Lubing up the sex toy with a big dollop of baby lotion, Clara positioned the butt plug so that it was touching Blake’s rear entrance. His wincing only made her want to tease him more, sliding the tip in and out of his slot and rubbing it around his outer lips. “Let’s count down together, okay?” said Clara, her voice dripping with sexual liberation, “Three, Two-” In one fluid motion, she pushed the plug as hard as she could, jumping the gun on the countdown to catch Blake off guard.

Blake’s eyes shot open and practically bulged out of his skull as about a third of the black butt plug entered his anal canal. It couldn’t have been more than a couple inches, but it felt as though someone had taken a flag pole and mounted him with the whole thing. As the plug slithered in and out to lube up his tailpipe, his voice cracked, emitting something that was somewhere between a painful cry and a frenzied moan.

Clara couldn’t get enough of the noises that came out of Blake’s mouth. She continued sliding the butt plug in and out, watching as the base sunk deeper and deeper with each attempt until it passed the halfway mark. Every time she thrust it into him, she stirred the toy around a bit, further stretching out his colon.
Finally, it was time to finish the job. Having neared the two-thirds mark, Clara knew she had enough leverage and had loosened Blake up sufficiently to plunge the whole thing into him. Winding up for one last big push, she launched the plug into his booty until only the base of the toy was visible. At last, Blake’s cherry had well and truly popped.

“Ooooooooh!” shouted Blake, his eyes crossed as his brain refused to come down on one side or the other of whether or not this produced pain or pleasure. He’d always heard that the male prostate was a gateway to more powerful orgasms, but his straight male persona refused so much as to entertain the concept. Having now experienced it for himself, he couldn’t say he agreed.

Regardless of Blake’s willingness to accept reality, it was clear that his penis certainly had. He’d been so focused on what was happening with his butt that he didn’t realize that he was rocking a massive hard-on. “N-No! I swear I don’t like this!” he yelled as if trying to convince himself along with everyone else.

Needless to say, there wasn’t a single person in a thirty-foot radius that even remotely took Blake at his word. Rapturious applause and scores of cheers surrounded him, further driving home his new status as a bonafide Baby Slave.

Clara, on the other hand, could feel their passion for punishment fueling her desire to further experiment. She took hold of his dick and clinically pressed it upward so that it was flat enough to fold the diaper over him. As she pulled her hand away, she couldn’t help but notice how much he had dribbled onto her hand. “There we go, now you can make all the squirties you want,” she teased, wiping her hand off on a nearby towel before securing his tapes.

Blake felt as though he might pass out, yet his adrenaline kept him wide awake. He wanted to scream, cry, and cum all at the same time and he couldn’t stand it. Screw Clara and screw this bet. He had to get out of here asap! In an act of desperation, he rolled himself off of the changing table away from both Clara and Darla. It wasn’t exactly a full-proof plan, but he didn’t have much of a choice. Running was his only option.

Unfortunately, Blake failed to calculate where the hand pump for his inflatable butt plug was. As he crashed to the floor, his hip slammed against the smaller bulb, instantly increasing the width of the toy. “AHHHHHHHH!” he screamed as his body worked against him. With his penis pointed upward, everyone watched with glee as he splattered semen all over his upper body, covering his arms and stomach in his own ejaculate. Uproarious laughter filled the space.

“Ahahahaha! I guess I should’ve tucked your princess parts in better,” said Clara as she rounded the changing table. She reached down to take Blake by the arm, “There’s no use trying to escape, Blakey-poo. You’re not going anywhere.”
Rage quickly filled Blake’s body, unable to stand the teasing and laughter any longer. He pushed away Clara’s hand and scrambled to his feet. Wearing nothing but a diaper, he barreled forward into the crowd, shoving past several other baby slaves and caregivers along the way. A few bystanders tried to grab him, but the jizz he was covered in acted as a lubricant, making it impossible for any one person to hold onto him. Eventually, he broke through the onlookers and sprinted down a nearby hallway.

Smirking, Clara stepped up onto the changing table and watched Blake disappear down one of the corridors. “You can run, but we will find you, Blake!” she yelled as she stood proudly atop the table.

Looking from side to side, Blake had absolutely no idea where he was. The Auction House’s lower floors were practically a maze and with only one exit, he’d need to find some way to get back to the main floor. Turning back, he knew it was only a matter of time before someone came searching for him. He needed to find somewhere to hide, at least until the heat died down. With no time to be picky, he dashed forward toward a set of three doors.

TO BE CONTINUED…

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