Supreme Casanova: Ultimate Harem System

As Hugo sat between Rin and Rai, legs crossed, arms casually stretched along the back of the bed like he was the undisputed king of the universe, he couldn't help but feel like he was on the verge of something legendary.

'This is it. This is my moment. My masterpiece. My magnum opus. If I can pull this off tonight, even the SYSTEM is going to look at me and say, 'Damn, this guy is built different!''

It wasn't everyday you managed to see an average 18 year old charming the pants of two amazingly beautiful baddies!

Especially the getting the pants of part! That was definitely not easy!

Which was why this game was going to be crucial for bus grand success. Everything had to be done strategically.

He had to orchestrate this game perfectly. No boring dares. No weak truths.

Every choice had to push the boundaries just enough to make things more exciting, to ensure that shyness was completely erased, and most importantly, to set the tone for something… greater.

It was definitely going to be fun!

He cleared his throat dramatically. "Alright, ladies. Let's lay down the ground rules so there's no escape—I mean, no confusion," he said, flashing his most charming grin.

He had almost slipped up right then! Luckily he recovered in time. Still, they had heard him…

Rai gave him a suspicious look. "Escape? What kinda game are you planning here, Hugo?"

Hugo chuckled. "Oh, nothing too crazy. Just a game where if you pick dare, you have to actually do it—no backing out, no 'Omg I'm shy' nonsense, and absolutely no complaining!"

Rin smirked, crossing her arms. "And what about truth?"

Hugo tapped his chin. "If you pick truth, you have to answer honestly—none of that 'I don't know' or 'skip' business. And trust me, the questions won't be weak. We go deep."

The girls exchanged amused looks before nodding. "Alright, sounds fair," Rai said.

Hugo grinned. Everything was going according to plan!

"Then let's get this started."

He grabbed an empty bottle from the nightstand and placed it in the center of the bed, giving it a strong, confident spin.

The bottle whirled around furiously, making small tapping sounds as it turned, before slowing down, inching its way past Hugo, past Rai… and landing directly on Rin.

Perfect!

Hugo turned his head dramatically, grinning like a villain. "Alright, Rin… Truth or Dare?"

Without hesitation, Rin flicked her hair back and leaned forward slightly. "Dare."

Hugo's eyes widened slightly.

'A divine woman. An absolute queen. No hesitation. Straight to the point. This is what I live for.'

As the person starting the games, she had instantly started it off on a very good start. This way things would progress quite fast!

A devilish smirk spread across his face. He already knew what he was going to say. There was no hesitation in his mind!

"Alright, then. I dare you… to kiss Rai."

The girls blinked. Then, as if they had already seen this coming from a mile away, they exchanged looks before giggling.

"We knew you were gonna say that," Rai teased, shaking her head.

Rin smirked. "Yeah, we literally could have bet money on it."

Hugo placed a hand on his chest, feigning innocence. "What? Me? Predictable? No way."

Rai gave him a knowing look. "Mhm, sure. You totally didn't just set that up so you could watch us kiss."

Hugo chuckled, but internally, he was screaming in victory.

'They see through my plan. They know my intentions. And yet, they're still going through with it. Do you understand what that means?! This is next-level rizz. This is advanced game strategy. This is 4D chess.'

Without further hesitation, Rin and Rai leaned toward each other, closing the small gap between them until their lips met in a soft, sensual kiss.

They were literally directly in front of Hugo, with both of them leaning over his thighs and placing a hand in his lap.

Hugo's eyes widened slightly as he took in the sight, watching as the kiss lingered for a second before they slowly pulled away.

He felt a strong sense of satisfaction surge throughout his body. He almost ascended on the spot!

'Beautiful. Stunning. A cinematic masterpiece. I have truly outdone myself tonight.'

But then, because he was Hugo, he leaned forward, frowning slightly. "Wait, hold on. I don't think I saw that properly."

The girls turned to him in amusement. "Excuse me?"

"Yeah, yeah," Hugo nodded, waving his hand. "See, from my angle, I only got like, 65% of the full experience. I think y'all should do it again. Just to be fair."

Rin and Rai exchanged a look. Then, without hesitation, they did it again.

But this time?

It lasted longer. They even used their tongue a little bit!

Hugo internally exploded.

'I'm a genius. I am a literal architect of greatness. Someone needs to give me a trophy. No—a statue.'

The second time they pulled away, they turned back to him with smirks.

"Did you see it properly this time?" Rin teased.

Hugo nodded seriously, stroking his chin. "Yeah, that was much better. Good technique, 10/10."

Rai shook her head, laughing. "Alright, let's see who's next."

She grabbed the bottle and gave it a hard spin. It whirled around quickly before slowing down… inching closer… closer…

And landed on Hugo.

Oh.

The girls immediately turned to him with wicked grins.

"Alright, Mr. Smooth," Rin said, leaning forward. "Truth or dare?"

Hugo's heart raced slightly, but he kept his cool. This was the perfect moment. He wasn't going to chicken out now and suddenly say truth. He had nothing to fear from them, after all.

He smirked. "Dare."

Internally, he was manifesting his fate.

'Please be something freaky. Please be something freaky. Please be something freaky.'

Rai's eyes sparkled mischievously. "Alright, Hugo… I dare you to—"

…..

The room was warm, the dim lights casting a golden hue over the three of them as the bottle of fate continued to dictate their destinies.

Hugo had been playing it cool all night, maneuvering every twist and turn of this game like a master strategist; but now, he was sweating.

And not in the way he'd expected.

Because at that moment, his arms were shaking, his breath was ragged, and his body was strained in ways he had not prepared for.

'I thought tonight was gonna be legendary in a completely different way!'

His muscles flexed, his jaw clenched, and a deep grunt escaped his lips as he pushed up one last time.

"Ughhh…"

Rai sat back, watching with mild amusement and absolute evil in their eyes.

Hugo gritted his teeth, his body trembling slightly.

'Is this what they call suffering? Am I being punished for flying too close to the sun? Is this the universe telling me that being TOO good at rizz comes with consequences??'

The scene sounded wrong. Very, very wrong. The way his body moved, the way he was grunting with effort, the way his face twisted into something halfway between pain and determination—it was all misleading.

And then, to make things even worse, Rai let out a dramatic moan.

"Ahh~ Hugo, you're so strong~"

Hugo's arms almost gave out right then and there.

Rin burst into laughter, clutching her stomach, while Rai, who was literally laying on Hugo's back, kicked her feet mischievously.

"You guys are insane," Hugo wheezed between reps. His entire body was on fire.

Rai leaned down and whispered into his ear, her voice teasing. "Don't slow down now, Hugo~ You have twenty more to go."

Hugo screamed internally.

'WHEN I SAID 'NO BACKING OUT OF DARES,' THIS WAS NOT WHAT I HAD IN MIND!!'

He had been so confident, so smooth, setting up this game like a master of the art.

But now, he was here, doing push-ups with a whole human on his back, grunting like a man possessed, while the other girl watched and laughed.

'I planned for a wild night. I did NOT plan for an intense workout session.'

His arms shook violently, his breath was labored, and the mere sound of the smirk of absolute smug satisfaction on Rai's face was almost too much to bear.

With a final, desperate burst of strength, Hugo completed the last rep and collapsed onto the floor, face-down, arms sprawled out like a dead man.

The room was silent for half a second. Then Hugo groaned, turning his head slightly. "You two are demons."

Rin giggled. "Oh, come on, you handled it well."

Rai, still sitting triumphantly on his back, swung her legs playfully. "Yeah, Hugo~ You're so strong. I bet you could have done ten more if you really tried."

Hugo's soul left his body.

'She's pushing it. She's really pushing it. I need to put her in her place.'

So, in one smooth motion, Hugo lifted his hand and smacked Rai's butt.

A sharp slap echoed through the room.

Then—

"Ahhh~!"

The entire room went silent.

Hugo's brain froze.

Rai immediately slapped a hand over her mouth, her face turning red, and Rin… Rin just stared at her, then at Hugo, then back at Rai.

Then, like fireworks going off in the sky, Rin exploded into laughter, falling back onto the bed, kicking her legs like a madwoman.

Hugo, still face-down, felt his soul leaving his body for the second time that night.

'WHAT IN THE NAME OF ALL THAT IS HOLY JUST HAPPENED?!'

His mind was a hurricane of thoughts.

'Did she—did she just—??'

'Was that a moan?!'

'I WAS JUST TRYING TO GET REVENGE FOR THE PUSH-UPS, WHY IS SHE SO EAGER!'

Rai, realizing the situation, immediately buried her face in her hands. "OH MY GOD, IGNORE THAT."

Rin was crying from laughter. "Oh nooo, Rai, you just EXPOSED yourself!"

"I SAID IGNORE IT!" Rai yelled, grabbing a pillow and smacking Rin with it.

Hugo, still trying to recover, sat up slowly. He turned to Rai, smirking. "Sooo… what was that reaction?"

Rai threw the pillow directly at his face. "SHUT UP."

Hugo snorted, catching it easily. "Noted."

Rin, wiping tears from her eyes, finally sat back up. "Okay, okay, I think we need to get back on track. It's Rai's turn now, right?"

Rai, still red in the face, nodded quickly. "Yes. YES. Let's move on."

She reached out, spun the bottle a little too aggressively, and crossed her arms, trying to compose herself.

The bottle twirled, slowing down until…

It landed on her.

Hugo's smirk widened. "Ohhh, perfect."

Rin grinned. "Alright, Rai… truth or dare?"

Rai, still clearly recovering from the incident, exhaled and sat up straight. "Dare."

Rin and Hugo exchanged looks.

Then, Rin leaned forward, eyes glinting with mischief. "Alright. I dare you to…"

She paused for dramatic effect, letting the tension build.

"Demonstrate your favorite position."

Hugo's eyes widened. The room fell silent for a split second. Then, before Hugo could even process the absolute genius of this dare, Rai smirked.

'Wait a minute. That look in her eyes… That's not the look of someone who's gonna back out.'

Then, before he could even react, Rai grabbed Hugo's arm and pushed him down onto the bed.

Hugo barely had time to register what was happening before she pounced on him.

The first thought he had when her thick thighs straddled him was this…

'Ladies and gentlemen… I have won.'