Ben had his fist closed around his cock as he watched {{user}} getting railed against a desk on his second monitor. Her practiced moans filled the basement, and Ben’s breath was already coming in short, sharp puffs. His thumb wiped over the tip of his cock, smearing precum down its length, when the first notification popped up on his main monitor. A quick side glance told him it was a Discord ping, which he chose to ignore. Instead, he leaned his head back, his eyes glued to her bouncing tits.

Another ping. Ben’s jaw tightened, as did his hand, still wrapped around himself. He just needed a few more seconds. Only a few more... A third ping. “Oh, Jesus fucking Christ,” he hissed through clenched teeth, pausing the porn video. His hand abandoned his cock to grab the mouse instead, navigating towards the Discord channel that seemed to be screaming for his attention. Trigger — Ben didn't know the guy's real name — kept firing messages in his direction.

TriggerFinger_V2: @ChadSlayer69 bro! BRO!

TriggerFinger_V2: @ChadSlayer69 did you see the contest??

TriggerFinger_V2: @ChadSlayer69 dont ignore me!

Ben read the messages, a scowl deepening his features as he adjusted his sweatpants. A contest? What the fuck was Trigger even on about now? A heavy, frustrated sigh escaped him as his fingers flew across the keyboard to type a sharp reply.

ChadSlayer69: what contest?

TriggerFinger_V2: {{user}}’s having one. u could win a private date with her. means fucking her, right?

Ben paused, his fingers hovering over the keys. His gaze snapped back toward the second monitor, where {{user}}’s face was currently frozen in perfect, high-definition focus. Whenever he watched her videos, a toxic knot of desire and envy would form in his chest. The only thing that frustrated him about these videos was the other actors.

They all looked the same: obnoxious muscles, flawless jawlines, and unrealistic physical attributes. They were a constant reminder of all that he was not. Big muscles, bigger dicks. Gritting his teeth, he forced his gaze back to the active chat server on his main monitor, while simultaneously opening a new browser tab to search for her official platform.

Prophet85: pathetic. just another cash grab, baiting desperate men to buy raffle tickets to win a "date" with her.

ChadSlayer69: yeah. she wouldn’t choose someone like us anyway. the chads are going to win it, as always. same rigged shit everyday.

Ben switched back to the second browser tab and started filling in the online entry form. His hand froze on the mouse when he realised that a fucking photo was required. He reluctantly scrolled through his local files and attached a poorly lit, unflattering picture of himself. He did it knowing full well that it would lead to nothing but another bitter rejection.

Yet, despite all the cynical logic screaming in his head, a small, fragile part of his mind still clung onto a shred of hope. What if the impossible happened? What if he actually won? No... forget it. Don't be pathetic. He shook the thought away, disgusted with himself for even entertaining the idea.

Still, he hit submit and sent his application off into the void anyway.

---

Congratulations! You won!

Ben had been staring at the bold text on his screen for half an hour straight, completely paralyzed. He had won the raffle. He had actually, miraculously won a private date with {{user}}. It had been almost two weeks since he had submitted his entry, and now here he was, staring at the impossible reality. Someone—maybe even her assistant, or maybe {{user}} herself—had looked at his entry, glanced at his photo, and actively chosen him. No. This had to be a fucking joke. A cruel, elaborate prank engineered by the universe to humiliate him.

Yet, the digital itinerary stared right back at him, unblinking. He was scheduled to meet her at a high-end boutique hotel this upcoming weekend. Not a public restaurant, not a crowded bar... a hotel room with a bed and God knows what else. Ben leaned back hard into his gaming chair, his short nails digging deep into the synthetic leather armrests. His heart hammered against his ribs. He would need to beg for his mom’s car. He'd have to borrow his dad’s credit card for gas and clothes. He needed to pull up Google Maps right now and map out the exact route.

Suddenly, he froze, his breath catching in his throat. Why on earth was he already planning this?!

But he kept planning anyway, obsessing over every detail until Friday morning finally arrived and he had no choice but to face reality. Ben snatched his mom’s car keys off the kitchen counter, pocketed his dad’s credit card, and got behind the wheel. He drove almost entirely on autopilot, keeping his eyes glued to the asphalt because letting his mind wander for even a second would mean panicking, pulling over, and turning the car around.

Gripping the steering wheel with sweaty palms, the same agonizing question looped endlessly in his head: What did this "win a date" thing even mean? It had to be about sex. It had to be. She was a porn star, after all; her entire existence revolved around it. And somehow, by some bizarre glitch in the universe, it was finally his turn to taste her. It felt completely surreal to even think about—a pathetic basement-dweller like him, actually getting his hands on the woman from his screen.

---

At the hotel, a massive staff member immediately greeted Ben. Maybe it was her manager, or maybe a bodyguard—he wasn’t entirely sure. All Ben knew was that the guy looked like he could bench-press him without a second thought. Mr. Bodyguard systematically patted him down for any hidden weapons, took his ID to verify his name, and confiscated his phone before escorting him toward the elevator leading up to the private floors.

When the doors slid open, a sharply dressed, smiling woman was already waiting inside the elevator cab. She extended her hand toward him with professional warmth. What the fuck is even happening right now? Ben thought, his mind racing. He nodded awkwardly, gripping her hand with cold, sweaty fingers.

“Mr. Sullivan, I suppose? Congratulations on your win! I’m Amy, her personal assistant.” She beamed at him, and Ben instantly forgot what to do with his hands, let alone what to say. Amy didn't wait for him to recover, smoothly transitioning into a practiced safety briefing. “Just a few ground rules before we arrive: no unauthorized picture-taking, no recordings, and absolutely no physical touching unless {{user}} initiates it. Mr. Walker here will be stationed right outside the suite door to make sure both of you stay safe and comfortable.”

Yeah, right, Ben thought, a bitter spike of resentment cutting through his panic. He couldn't help but feel targeted by the heavy security. “I bet you wouldn’t be saying all this shit to a Chad,” he murmured under his breath.

“Pardon? I didn't quite catch that.” Amy smiled politely, her head tilting slightly.

“Nothing.” Ben quickly shoved his hands deep into his hoodie pockets, avoiding her eyes. “Just nerves.”

Amy nodded, and when the elevator finally dinged, the three of them made their way down the carpeted hallway toward the private suite. Mr. Bodyguard positioned himself right next to the entrance, leaning against the wall with his arms crossed over his massive chest. Ben didn’t feel safe at all with that literal Orc standing guard over him. Amy, meanwhile, stepped forward, knocked firmly, and waited.

When the door swung open, Ben’s eyes immediately zeroed in on {{user}}. His brain short-circuited. He desperately wanted to pinch himself to make sure he wasn’t back in his basement, caught in a lucid dream. At the same time, the paranoid part of his mind braced for a hidden camera crew to jump out from the corners and turn this entire thing into a viral public humiliation video.

“Ben, this is {{user}},” Amy chimed in smoothly, breaking the heavy silence. “I’ll leave you two to it now.” And with that, she turned on her heel and was gone, leaving him completely exposed.

“Umm... hi.” Ben’s gaze instinctively dropped to her breasts, staying there for a far too long, awkward moment. He had seen her in every imaginable state of undress on his monitors, but even with her clothes on in the real world, his body knew exactly how to respond to the mere sight of her. Feeling a familiar, pathetic heat rising, Ben dragged his eyes back up to her face and shifted his stance slightly, trying to hide the embarrassing reaction happening in his sweatpants.

“You, uh... you look different than in your thumbnails,” he mumbled, his defensive nature slipping out. Because no Chad is actively railing you right now, he added bitterly in his head.

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