Matt (Sarah's sadistic scheme)

Sarah's search for a scrap of paper was brief and aggressive, her temper having been shortened by the perverted eyes all over her, that watched every slight jiggle of her breasts with bated breath. Even the snatching of a slip from the hat made her impressive breasts bounce hypnotically enough that Matt's fingers gripped the arm of his chair, like he was engrossed in an intense thriller.

It was reading his name on the paper and seeing him staring at her that made up Sarah's mind about what she would dare him to do. "Matt," she barked his name aggressively, intentionally shocking him out of his wistful gazing and making him jump in embarrassment in the process.

"S-s-sorry," he began to stutter, only for Sarah to bulldoze right past his jumbled attempt at an apology.

"I drew you," she continued. Between two fingers she waved his little slip like a flag, clutching it by the very edge as if she was worried that the cooties from just his name would rub off on her. Like throwing away trash, she dropped it back into the hat before saying her dare. "I think you're very lucky that you get to see all this," she gestured to her chest as she spoke, straightening up in her seat to better show off her 100% natural, jiggly, tits.

"To make things even between us, I want you to strip down to your boxers," she completed her dare with a smirk, one that only grew when she saw Matt blush preemptively. If Nicole had to guess, she would have thought that Matt was the type of guy who waited until everyone else had left to get changed for gym in high school, and she doubted he would have grown out of that attitude now that he was at university. With no one to **** him, he had probably never even set foot in any of the campus sporting facilities.

Sarah had probably spent more time in the guy's locker room than he had, crawling around on her knees and 'motivating' the entire football team to 6 back-to-back wins. If only he had seen her then, pleasuring five hot, sweaty, guys at the same time, rewarding them for their dominant success by giving them her tight, young, holes, then he definitely wouldn't have developed the crush on her that he had now.

A smile played on her lips as she remembered those happy, horny, hours, before she shook her head and regained her train of thought. The point of her dare was that she was sure Matt would be uncomfortable stripping down to his underwear, and that whatever he showed off in the process would be embarrassing anyway.

Her theory was already being proven right as he awkwardly got to his feet, his narrow shoulders already hunched defensively. It looked as if he wanted to say something to her in response, but whatever attempt at flattery or request for a reprieve he was trying to muster died in his throat. The way his hands trembled as they reached for the buttons on his shirt almost made Sarah feel bad, and she even considered giving him a mercy rule so he could just leave (and never come back) instead.

Before she could, however, Tom chimed in. "I hope he is wearing underwear," he laughed, "I don't want to see Matt wearing a tiny strip of 'cock tape.’” That comment made Miranda and Sarah laugh, even while Matt flinched at the words as if a fist had been thrown his way.

"I highly doubt such a product would exist," Nicole snootily replied, doing her best to defend her friend.

She wasn't alone. Almost heartwarmingly, John joined in, saying, "yeah, and if they did, Matt would need like a mile of it." His words raised a few eyebrows, but his point was clear, even if Sarah doubted it was true. The three of them began to bicker back and forth, mocking jokes clashing against sincere defenses. Using the noise as distraction, Matt began to unbutton his formal shirt, and Sarah's mind wandered again.

She found herself wondering if she wanted him to be wearing underwear, or not. On the one hand, she didn't really want to be exposed to whatever wrinkled and pathetic thing he called his dick, but on the other hand, having to expose his shame in front of everyone would almost certainly drive him away for good. And if just whipping out his Shrinky-dink dick didn't make him leave, Sarah would laugh as loud and as hard as she needed to get him to go.

By the time she had finished thinking about Matt's cock (hopefully for the last time in her life), he had finished undoing his shirt. The sight of his bare chest was as unimpressive as she'd expected. The rest of his frame was as wiry as his twiggy forearms, with ribs nearly visible through the very pale skin of his chest. Only a small handful of body hairs decorated his chest, singular dark curls that stood out starkly against the white canvas of his skin, making him look almost like a cartoon character.

The room quieted down again as Matt's focus shifted to his lower half, to his obvious discomfort. From the way his jeans were cinched in so tightly at the waist, it seemed apparent that they didn't really fit him, and were instead lashed tight to his slender form by his belt. He was somehow even skinnier than Sarah had thought. Tenting her fingers, she leaned forward to watch just like everybody else, giving the clumsy nerd no reprieve form what must have been similar to his worst nightmares.

If Sarah had thought Matt taking his shirt off had looked awkward, then she had seen nothing yet. First he nearly tripped over his own feet as he kicked his shoes off, and then it took him an uncomfortably long time to unbuckle his belt. When that strip of leather was finally pulled loose, his jeans sagged so much so quickly that he was almost stripped to his underwear in a heartbeat. Instead, he caught his waistband with one hand, before looking pitiably towards Sarah.

An "encouraging" smile from her was all it took for him to take a deep breath, gulp, and then shove his jeans down. Fortunately for the eyes of all the partygoers present, Matt was wearing underwear. Unfortunately for Sarah, it was less embarrassing than she had hoped. Instead of a ratty pair of overworked briefs or the classic white boxers with red love hearts all over them, Matt wore a pair of boxers that were as boring and sensible as his jeans. They fit him a little better at least, holding to his hips instead of nearly falling down without support.

Tom wolf whistled again, driving Matt's knees together while Miranda laughed at him once more. In jerky movements, like a broken automaton, Matt covered his crotch and glanced down to check nothing was showing, before slowly removing his hands and standing a tiny bit straighter. As if he was asking for her opinion, he slowly turned his head toward Sarah again.

Intentionally keeping him waiting for a moment, Sarah picked up her wine glass and took a long, slow, sip, enjoying watching him squirm in the corner of her eye. Finally, she put her glass down and turned to face him, purposefully staring at his underwear with a quizzical expression to make him even more uncomfortable. "Nice undies Matt," she eventually said, "did your mom buy them for you?"

Tom and Miranda laughed again at that, while John and Nicole smiled good naturedly. "Ha, g-good one," Matt laughed, his shoulders relaxing slightly. Still blushing, he began to reach for the hat, only for Sarah to stop him.

"Answer the question," she cut him off, his hand halfway to the hat. "Did your mommy buy them for you?" She repeated herself, making it clear that it wasn't a rhetorical this time. She hadn't planned on putting him on the spot like this, but something about the pathetic way he held his shoulders compelled her to do so.

Like a cornered animal, Matt's eyes rose slowly from the hat. He met her gaze with a mixture of confusion and fear, but he found no pity in Sarah's face. She simply waited impassively, pouty crimson lips pursed expectantly. The room fell completely silent as they too awaited his answer, looks of confusion or bemusement on everyone's faces. In desperation, his eyes darted around the room, but there was no escape. Sarah had put him in a spotlight, right where she knew he didn't want to be, and left him with ****.

"Y-yes," he admitted, staring down at the floor.

"Yes, what?" Sarah probed.

"Yes, my m-mommy bought them for me," Matt clarified, his eyes wearing a tunnel into the carpet. Sarah had been fishing for him to say “yes ma’am” but that would do too. The tension in the room was broken as Tom burst out laughing at his response, and John and Miranda looked around in unease and amused confusion, respectively. Only Nicole looked at Sarah, pinning the sexy red haired girl with a deep frown that Sarah met with a smug smile before turning her attention elsewhere.

"Here's the hat, Matt," Sarah handed it to him, rewarding him with a smile for his honesty. Shamefully hunched double, he took it with only a glance up into her eyes, before shuffling back to his seat. As he sat down, still hunched forward, Sarah noticed an undeniable tent in his boxers. That filthy nerdy pervert had gotten hard as she’d made fun of him. Sarah couldn’t believe it. It must have just been that he was so unused to talking to women that he popped a boner whenever one spoke to him, no way he’d enjoyed that humiliation. Either that, or Sarah was just even hotter than she thought.

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Thank you for reading, I hope you enjoyed seeing Matt's humiliation truly begin. If you did, then the next two chapters are available to members on my Patreon. This week, we got to see someone who was much more comfortable in the limelight perform for the enjoyment of the other guests. The vote to decide how Miranda will act in an upcoming chapter is also still available, and as of right now it is a three way tie! If you want to decide what attitude she should have, then feel free to become a member and vote!

https://www.patreon.com/Cheesers123