Supreme Casanova: Ultimate Harem System

The next game was something the YouTuber called "The Roast and Boast Challenge", and it was absolute chaos.

The concept was simple.

Each person had to either roast someone in the room with a brutal (but funny) joke or boast about something completely ridiculous as if they were the greatest person alive.

If the joke flopped or the boast wasn't crazy enough, they had to take a punishment which was usually something humiliating, like getting water poured on them or doing a cringe-worthy dance.

Of course, Hugo was thriving.

"Alright, Hugo, your turn!" the YouTuber called, pointing straight at him.

Hugo leaned back in his chair, smirking like a man who had never known fear. "Oh, this is too easy."

He was a demon otaku! Roasts were his forte!

He gestured toward one of the buff guys in the room, a towering 6'5 dude who looked like he bench-pressed small cars for fun.

"My man over here looking like he was built in a lab specifically to block the sun. If we ever have an eclipse, I know who's responsible."

The whole room exploded in laughter as the big guy just shook his head, grinning.

"You got lucky, Hugo," the YouTuber said, wiping tears from his eyes. "That was solid."

One after another, people either roasted or boasted, with some hilarious results.

One guy tried to boast that he was the greatest rapper alive, only to butcher his freestyle so badly that even autotune couldn't have saved him.

Another girl roasted Sanchez, saying, "Bro thinks he's a dark and mysterious billionaire, but he's just a dude who refuses to turn on the lights in his own house."

Even Sanchez had to laugh at that one.

The punishments? Brutal. One guy had to run around the house barking like a dog.

Another had to sing a cringe 2000s love song while dramatically staring at the camera. By the time the game ended, everyone was crying from laughter.

But Hugo? Hugo had bigger things on his mind.

—

For the next hour, Hugo kept trying to get a moment alone with Rin and Rai. But fate, or maybe just some sick cosmic joke was not on his side.

Every time he thought he had a chance, something would interrupt.

First, it was a group of girls who had pulled them into a conversation about skincare routines, leaving Hugo standing there like an extra in his own movie.

Then, it was some YouTubers who wanted to take pictures.

Then, it was another girl who very aggressively wanted Rai to teach her how to pose for Instagram photos.

Hugo was dying inside.

'Is this what suffering feels like?' he thought, dramatically leaning against the wall.

'Am I cursed? Is there some kind of divine force watching me struggle and laughing? How is it that when I don't want interruptions, I get free time, but the moment I need five minutes, suddenly the whole universe is plotting against me?'

At one point, he was this close to just grabbing both girls and dragging them into a corner like, "PLEASE, JUST ONE MINUTE."

But that probably would've looked insane, so he restrained himself.

And then, finally—FINALLY—he got his moment.

The girls were sitting on the couch, laughing about something, and there was nobody around.

Hugo took a deep breath, hyped himself up, and walked over, casually sliding into the seat next to them.

"Sooo," he started smoothly, looking between them. "I was thinking… since we all get along so well… how about we all stay in the same room tonight?"

Rin and Rai blinked at him for half a second.

Then, at the exact same time, they both answered his question.

"Sure."

Just like that. No hesitation. No dramatic pause. No thinking it over. Just a simple, instant agreement.

Hugo's brain malfunctioned.

'Wait, what?' he thought. 'THAT WAS WAY TOO EASY. WHERE WAS THE CHALLENGE? WHERE WAS THE DRAMATIC BUILD-UP? THIS FEELS ILLEGAL—'

But on the outside, he just nodded smoothly, keeping his composure. "Cool, cool. Yeah, I mean, makes sense. We all vibe really well, right?"

Rai grinned. "Exactly."

Rin nodded. "Besides, it'll be fun."

Hugo casually stretched, but inside he was celebrating like he had just won the lottery.

That had been to easy!

Of course, he had to go find Sanchez after that.

Hugo practically floated into the room where Sanchez was chilling, dramatically plopping onto the couch next to him with the smuggest look on his face.

Sanchez glanced at him, unimpressed. "Why do you look like you just found out you're getting a million-dollar inheritance?"

Hugo sighed happily, staring up at the ceiling. "Because, my dear cousin, I have ascended. I have reached a level so high, it cannot be taught—it must be earned."

Sanchez rolled his eyes. "What happened?"

Hugo sat up, grinning. "Rin and Rai? Sharing a room with me tonight."

Sanchez choked on his drink. "WHAT?"

Hugo patted his shoulder. "I told you, man. You gotta play the game right."

Sanchez stared at him, then sighed deeply, rubbing his temple. "I hate you."

Hugo laughed. "Nah, bro, you love me."

Sanchez groaned. "This is why I don't believe in happiness."

Again, he felt the surge to discard his useless Mysterious owner act and just pounce after the girls!

But still, he managed to calm down once again at the last minute and continued sipping his drink.

Patience was a virtue. His prize would come from the universe…

Later that night, Hugo led Rin and Rai toward his room, trying to act as chill as possible while internally calculating all possible future moves.

The three of them walked together, making casual conversation.

The girls were talking about some funny moments from earlier, and Hugo nodded along, but his mind was already working overtime.

'Alright. First, keep the conversation light. Make them laugh. Then slowly transition into something deeper. Ease into the vibes. Don't rush. Play it smart. Set the mood. No awkward moments. This is a delicate operation—'

Rai playfully nudged him. "You're awfully quiet. Something on your mind?"

Hugo snapped back to reality.

He flashed his signature smirk. "Oh, nothing. Just… strategizing."

Rin raised an eyebrow. "Strategizing?"

Hugo chuckled. "You'll see."

And with that, he opened the door to his room, leading them inside—ready to orchestrate the greatest vibe shift of all time.

Hugo's room was clean, simple, and effortlessly sleek, the kind of space that gave off a modern but lowkey vibe.

Everything was neat and uncluttered, almost as if the room itself had been prepared for a perfect night.

And Hugo?

He wasted no time.

The second he stepped inside, he dramatically flopped onto the bed, stretching out like he had just completed the most exhausting mission of his life.

He sighed deeply, sinking into the plush comfort of the mattress, before casually turning his head toward the girls and smirking.

"I really hope this room has soundproof walls," he said, voice dripping with mischief.

Rin and Rai both paused mid-step, looking at him with amused expressions.

Rai raised an eyebrow. "Oh? And why is that?"

Hugo placed a hand behind his head, grinning. "You know… just in case we get too competitive playing games or… I don't know… start discussing deep philosophical questions at 2 AM," he said, his tone making it painfully obvious what he was really hinting at.

Rin smirked, shaking her head. "Mmmhmm. Sure, Hugo. Philosophical discussions. That's exactly what you're thinking about right now."

Hugo simply shrugged, his Pro Rizz Execution already in motion.

He had dropped the clue perfectly, subtle enough to not be too forward, but obvious enough that there was zero chance these two smart, beautiful women wouldn't pick up on it.

And judging by their small smiles and exchanged glances?

Yeah, they caught it.

—

Not long after, the girls stood up and stretched.

"We're gonna shower real quick," Rai announced casually, running a hand through her hair.

Hugo, who was comfortably lounging on the bed, blinked and tilted his head. "Wait, we?"

Rin nodded like it was the most obvious thing in the world. "Yeah. Together."

Hugo's brain short-circuited for a second. He sat up instantly, eyes slightly widened. "Ohhh. Sooo… I assume that means I can join too, right?"

The response?

A giggle.

A very playful, teasing giggle from both of them.

And then they just walked away, completely ignoring his question as if he hadn't even spoken.

Hugo dramatically collapsed back onto the bed, placing a hand over his chest as if he had just suffered the greatest tragedy of his life.

"Why does life do this to me?" he thought, staring at the ceiling. "This could've been the greatest moment in human history… But no. Instead, I'm here. Alone. Suffering. Just another victim of bad luck."

Then, just to make matters worse, he started hearing giggles from the bathroom.

And then… slapping sounds!

Light, playful slaps.

As if—

Hugo sat up, eyes wide.

"OH. MY. GOD."

His imagination immediately took off like a runaway train.

'ARE THEY—ARE THEY PLAYING AROUND WITH EACH OTHER IN THERE?!?'

He gripped his hair, rocking back and forth slightly.

'No. No, this isn't fair. This is pure evil. Why wasn't I born with the ability to teleport? Why am I out here while they're in there, having the time of their lives? Is this a test? Is the universe testing me??'

He groaned, flopping onto the bed again, suffering in silence as the occasional giggle and splash of water kept his imagination running wild.

When the girls finally stepped out of the bathroom, Hugo had to take a second to process what he was seeing.

They were wearing matching pajamas—silky, short, and dangerously sultry.

Rin's set was black, giving her a sleek, elegant vibe, while Rai's was a deep crimson, a perfect contrast to her playful energy.

Their voluptuous figures were fully on display, their damp hair adding an extra touch of effortless allure as they casually walked over like they didn't just throw Hugo's mind into absolute chaos.

Hugo just stared for a second, his brain buffering.

'How… How is this even legal?'

Then, in his head, he instantly praised whatever divine entity had blessed this moment.

'I always knew I was one of the chosen ones.'

But on the outside, he simply smirked and nodded approvingly. "Damn. Y'all really coordinated just to flex on me, huh?"

Rai grinned. "Maybe."

Rin smirked. "You like?"

Hugo leaned back, crossing his arms. "Let's just say if I had a camera, y'all would be Vogue cover models right now."

The girls chuckled at that, clearly pleased.

A few minutes later, Hugo took his turn in the shower, keeping it quick but making sure to come back shirtless, only wearing a pair of loose shorts.

Why?

Strategic chest flexing.

He sat down between them on the bed, casually letting his toned chest do the talking, knowing full well that the best way to win a game was to stack all the advantages early.

And then, out of nowhere, he clapped his hands together.

"Alright," he announced, a devious smirk spreading across his face. "I just had an idea."

Rai raised an eyebrow. "Oh?"

Hugo leaned in slightly. "Let's play Truth or Dare."

Rin gave him a knowing look. "Ohhh, I see what you're doing."

Hugo chuckled. "What? It's just a friendly game."

Rai smirked. "Yeah, right."

Hugo just grinned, feeling ridiculously confident.

Let the games begin!