The Price of Losing

The Bet

"Hey, hey, Oliver, look! I found one just your size!" Jess popped out from behind the boxes of new stock we were unloading.

I looked down at her hands. She was holding an extra-small chastity device. I rolled my eyes.

"Haha!" She burst out laughing.

Her name is Jess. She's a 21-year-old cashier at the local sex toy shop in town. She's extremely forward and loves her job selling sex toys to all the creeps and perverts in the neighborhood. I, on the other hand, started working here just a few months ago, and I don't exactly fit in as it makes me feel nervous. To help me out, she made it her personal mission to teach me about the kinky world and make me blush and sweat as much as possible. Despite all the fun stuff we sold there, I had quickly become her favorite toy. I knew it, but never could had guessed how far things went.

"Jess, please, stop! You know that's not true," I protested, shaking my head. "There's no way I could fit in that. That cage is way too small!"

"Oh really? Too small for Oliver's little pecker, huh?" Jess giggled, holding up the device and examining it closely. "Well, let's put it to the test then, shall we? If you're so sure, why don't you prove it?" She stepped closer, invading my personal space.

"We can lock this baby up and see if you're telling the truth." She waggled the keys enticingly. "If it does fit, I get to keep these, and you have to wear it all day while we work. Deal?"

She leaned in, her voice dropping to a sultry whisper. "Plus, just think how turned on our customers will be if they catch a glimpse of Mr. Oliver sporting his very own chastity cage..." She bit her lip suggestively, waiting for my response.

"And if it doesn't fit what do I get?" I asked her confidently.

She smirked, tapping her chin thoughtfully. "Hmm, well, since you're so convinced it won't fit... maybe you've earned a little reward from yours truly."

She sauntered even closer, her hips swaying seductively as she reached out to trail a finger down my chest. "How about I let you pick out a toy from our collection to play with during your shift? Something to help you handle all that pent-up energy building up inside you..."

She winked, pressing herself against my arm, giving me a tantalizing view of her cleavage. "Of course, if you lose the bet, I still get the pleasure of watching you squirm in that tiny cage all day long," she chuckled wickedly. "So, what do you say, ready to give it a try?"

"I don't think it's fair, you're not involved in either outcome!" I protested, shaking my head. "If I don't fit, then you get locked in a chastity belt and a chastity bra. Deal?"

She threw her head back, laughing heartily. "Aww, is poor little Oliver worried about losing? Don't trust yourself to win?" She taunted, grinning.

"Alright, you're on! If your cock doesn't fit in this cage, I'll wear a chastity belt and bra all day long!" She agreed gleefully, clearly relishing the thought of our little wager.

"But you better be prepared to follow through if you lose! No backing out once we start!" She warned playfully, breaking into another fit of giggles.

She clapped her hands impatiently, eyes sparkling with excitement. "Now hurry up and whip it out so we can get this show on the road! Let's see what you're hiding under those baggy pants!"

"This is such an easy win," I replied confidently, starting to unzip my pants.

With a wicked grin, Jess watched as I fumbled nervously with the zipper, her giggles making me even more flustered. "Oh, Oliver, always so shy!" She teased.

As I finally pulled myself together, she leaned in close, inspecting with a mischievous sparkle in her eyes. "Mmm, looks like someone's getting excited already..." She murmured, smirking.