Chapter 6
by Pooperman
“Alice, I need an answer from you.”
“Um,” she began.
Bzzzt!
“I’m sorry,” Laura announced, “the correct answer is ‘chutzpah’.”
Alice groaned. The answer had been on the tip of her tongue--or so she lied to herself, anyway. Her heart raced as Laura started speaking again.
“For failing this, you will have to wear some special underwear.”
One of the stagehands produced a rectangular, black box that Laura then opened. Alice squinted to get a better look at what was inside. The crowd clapped before she was able to see what it was--a vibrant purple panty. Only, there was more to it than that.
“This is no ordinary underwear,” Laura continued, showing it to Alice and the crowd. “Inside of this there are two small plugs. I’m sure you can figure out where those go!”
The crowd erupted in loud applause. She continued once the audience settled down enough to speak.
“Alice, you will put these on instead of your current underwear. If you need lube, ask one of the helpers.”
Heat erupted on her face once she held the infernal underwear in her hands. The ‘small’ plugs Laura had mentioned didn’t look so small up close. They were bright purple, just like the fabric that contained them. The central one was definitely larger than the second one that she assumed was for her ass.
Alice took a deep breath and exhaled. She’d do this quickly, she decided. She got the lube from the man who’d given Laura the box and spread a liberal amount over each of the protrusions. As quickly as she could, she dropped her underwear and slid both her legs through the new pair until the first plug--the large, vaginal one--was resting against her lips.
The thin tip slid in comfortably, but her hole was stretched slightly as it widened before tapering down again once fully inside her. It wasn’t unpleasant at all, but it was a somewhat unwelcome intrusion nonetheless. The anal plug was another matter entirely. Despite the excessive amount of lube she’d put on it, her asshole was tight. Alice did enjoy anal on occasion but it had been a long time since her last encounter and her nervousness didn’t help. Slowly she pushed against the plug and it slid upwards, opening her up more and more. She gasped when plug pulled itself the rest of the way in on its own, her ass clenching tightly at the base.
By the time she had finished, Laura was standing next to the wheel to decide the next round. She gave an embarrassed look around the audience before walking her half-naked, plugged self to her place next to the wheel.
“Alice,” Laura said, “how are you feeling?”
“Full,” she answered with a half-hearted smile. A few people in the crowd chuckled at her response.
“Are you ready to continue?”
“Definitely,” Alice said with as much confidence as she could muster.
She pulled hard on the wheel and sent it clattering ‘round. It finally came to rest on a yellow wedge that Laura plucked out to read.
“Alice, for you next challenge--and forty-five thousand dollars--you will be playing our resident model, Ryan, in a game of Jenga.”
Ryan was wearing only a speedo--his bulge quite visible, though it was his muscles that her eyes were drawn to. She couldn’t discern if it was his appearance or the new underwear that was making her moist at that point. Breaking her gaze from his hard body, Alice saw a large tower of huge Jenga blocks that the staff had brought out while her attention had been elsewhere.
“Are you ready, Alice?” Laura asked.
“Let’s do this!”
Ryan didn’t move so she took the first move by removing the center block in one of the rows. The block was a couple of pounds--not as heavy as she’d feared but definitely substantial. Her opponent mirrored her move on another row and placed his block on the top.
A few rounds went by before the tower was almost beyond her reach and most of the blocks in the lower parts had been removed to the point that it was slightly unstable. Alice faced a choice. She could play it safe and hope her opponent would make a mistake, or she could take a gamble that would almost certainly **** an error--if she didn’t mess up first.
She decided to…
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