In her flowing blonde hair, crystal blue eyes, and soft lips, Sith found himself lost in admiration.

"Stop staring," a voice interrupted.

He turned to see Troy staring like Sith was an idiot (ಠ_ಠ), making him awkwardly look away.

Between them lay a chessboard, their match halted when Sith got a bit carried away. He analyzed the situation as he carefully moved his rook forward.

"You could just ask her out, you know," Troy said, pushing his own piece forward.

"Are you crazy?!" Sith almost shouted. "You'll lose both if you try to turn a friendship into a relationship."

Troy put on that expression again (ಠ_ಠ).

"You're not even friends in the first place. How often does she glance at you in a semester?" His words made Sith feel stupid.

"I know she's your sister but you should support me here," Sith sulked.

"Not when you can't even talk to her. Say, if I win, you'll tell her how you feel," Troy suggested.

"Then you'll strip in the hallway if I win?"

Sith expected Troy's face to darken, but he kept a calm look and nodded. "Deal!" Sith announced, placing his bishop to check Troy's king.

Troy's smile didn't waver, giving Sith an unsettling feeling. "Prepare your speech." He leaned in, making his move. "Checkmate."

It sounded impossible. How could a check become a checkmate in a single move? But the chessboard confirmed Troy's words.

"H-How…?" Sith stuttered.

"Like I said, prepare your speech," Troy replied with a calm smile.

That idiot. Does he want to see me rejected that badly? Sith wondered, dejected.

"Sigh. How do I even do it?"

"Stop being so gutless." Troy looked at him with disdain.

"Aren't you the playboy here? I should be learning from you," Sith said, but regretted it after.

Troy's proud expression made Sith want to slap him. "Ah, I wouldn't dare call myself that. But I wouldn't mind teaching junior brother some skills."

Sith glanced at the indifferent beauty surrounded by followers who wouldn't dare get too close. Troy coughed lightly. "Playboy 101: make it unforgettable. As long as it gets you on her mind, do it. You can work out the details later. She needs to have a considerable impression of you."

"How though? She doesn't even look at me," Sith complained.

"Best way is to save her life, but..." Troy's expression turned strange. "Let's try something romantic for starters."

"Would that work?" Sith was doubtful.

"Definitely." Troy seemed oddly confident. Sith had to trust him; Troy was the playboy, and she was his sister. Sith's eyes lit up.

"Isn't there an eclipse later today?"

Troy's expression became unnatural. "Is an eclipse romantic?"

"Well, the sun and moon align, so that's fortunate, right?"

"Alright, nerd. Just do it before the eclipse happens..." Troy's warning was serious. "And don't be late."

Sith wasted no more time. He hurried off to get ready.

____________

"Crap, I'm late."

He stood at the rooftop entrance, staring at the elegant silver bracelet in his hand. Remembering its price almost brought him to tears, but he slipped it in his pocket and proceeded hurriedly.

Then, he saw her—Hailey Constantine. She seemed like a celestial princess in that moment.

She turned as if sensing him. Their eyes locked, freezing him in place.

Don't simp. Act cool. He repeated the mantra as he pretended to be passing by.

"O-Oh? Hailey. I didn't expect you to be up here," he said with what he thought was his calmest smile.

Hailey's eyes flickered with confusion, alarm, and sudden realization. "So Troy sent me here because of you?" Her voice was unbothered.

"Uhh, y-yeah," Sith admitted, walking over. He touched the item in his pocket nervously, then he glanced at the now-crescent sun. Time was running out. He exhaled lightly.

Suddenly, Hailey jumped several meters away in instant. Just as he was about to speak, his body tensed. A feeling of dread shot through his soul. But before he could even move, something struck him in the chest with ruthless force.

Sith's senses went blank, his body flying back several meters. When he regained his bearings, he was heaving. His insides felt like they were burning.

"The princess is quite perceptive even without magic," a dry, raspy voice spoke.

A tall hooded figure with a red cloak stood a distance away, the whip in his hand retracting. Beneath the hood, a mask with a sinister design covered his face. As the shadows encroached, the figure looked menacing.

Hailey's eyes narrowed.

"So the strange energy movements was you," she vigilantly commented. "Who—"

"Don't bother with all that nonsense. It doesn't matter who I am. Right now, you should be more bothered with how you'll live," The cloaked man interrupted, his rusty voice impatient.

Hailey didn't move, her serious gaze stayed on the figure. She raised her opened palm to the darkening sky.

"Ensis."

Suddenly, a column of ink black flames erupted from her palms. It stretched into a thin pillar. She twisted her wrist, the flames twisting and condensing. Then with a clench of her fist, the fire immediately solidified then vanished.

A cold glint shone as she brandishes the sword now in her hand.

Magic! Sith was in shock.

"Confident?" The man sneered, shaking the whip in his hand.

It suddenly began to writhe and move in his grasp as if it was alive. In tandem, the man's arm began to twist and bend in unnatural angles.

Now Sith was completely shaken. He had just wanted to confess romantically, but everything had taken a complete deviation.

"The House of Constantine is pretty stupid, sending their heirs alone to another world all for what?" The man groaned, his voice becoming even scarier.

Hailey's gaze now had a hint of alarm.

She gravely turned to Sith. "I'll get an opening. You run and find Troy."

Sith, who was still panicking, suddenly heard Hailey's voice in his ear. He turned to look at her but she abruptly dashed forward. The man, who was still in the midst of his transformation seemed to have anticipated her movement.

With ease, he sidestepped Hailey's attempt to slice off his arm. Hailey didn't stop, however, swinging her blade backwards. He bent his knee, allowing the blade to miss his head by a few hairs.

With her lower body left open, the man ruthlessly swung his whip horizontally. After a burst of flames, the sword in her hand vanished, before appearing in front of the incoming whip in time.

The whip hit the sword, causing it to fly away in a random direction. In a flash, Hailey distanced herself, shouting, "Now!"

Sith was still stunned. One second, Hailey was there and in the next, she was yards away, telling him to run. Still, his survival instinct took over and he bolted for the exit.

But then, the whip in the man's hand suddenly elongated.

"Careless."

Hailey was caught off guard, allowing the whip to land on her leg, leaving a shallow bruise.

Upon seeing this, Sith stopped in alarm. Unexpectedly, Hailey stumbled, her body numb. Momentary pain and dullness shot through her entire body from that bruise.

A spirit weapon?! She thought in surprise.

The man didn't waste this chance as he brandished his whip. Just when was about to strike, an object bolted towards him. He immediately went on guard, shifting his attention to this immediate threat.

He lashed out his whip, slicing the object in two. However, when he looked at the "threat", he only saw a shoe in two clean pieces.

"Hailey!"

Rage flashed in his eyes. But just when he was about to mutilate that side character, a flash of black appeared in his periphery view. Followed by the cry of a enchanting voice.

"Wraithfire!"

His eyes widened in dread when he heard that. Before he could even muster the strength to move, it had arrived before him. He was struck cleanly with no suspense.

At first, nothing seemed to happen, only a faint mark could be seen on his clothes. But in the next instant, the faint mark began to glow rapidly...

BOOM*

The detonation ripped through the air like the boom of an artillery shell, the echo shooting through half the city.

Debris and dust flew in all directions, rendering that scene a complete mess. Even the air smelled of burnt metal and acrid smoke.

When Sith's mind finally came through, he couldn't help but stare at the area of the explosion in sheer astonishment.

His trifling action of tossing a shoe to a foe, then a sword to a friend had somehow resulted in this.

Just as he was stunned, a figure came flying out of the dust and smoke. Sith was alarmed at first, thinking the man came for revenge.

However, the figure landed in not-so-smooth way near him. He was relieved but worried to see it was Hailey.

Luckily, when he crawled up next to her, her eyes were open and she was still breathing.

"Thank you..." She said, weakly among coughs.

"It's nothing. Are you alright?" He asked, his eyes filled with concern.

"Y-Yeah," she nodded.

Seeing her enchanting side profile, Sith's breathing quickened.

Wait. Isn't this the special moment Troy was talking about?

He began to reach his hands into his pocket for the item.

"Hailey. I..." He began.

"Fuck! It's the Wraithfire curse." A sudden voice exclaimed, dropping the hearts of the two.

Hailey instantly tensed up. Without hesitation, she silently whispered and there was a burst of black flames followed by a sword. She firmly held the sword in her hands.

The man, whose mask had been shattered, glared at them with his sinister eyes before raising his head to the moon in the sky. A furious bestial roar escaped his throat.

Suddenly, a wave of crimson energy erupted from his body. Everything in a distance of a hundred meters fell still. Hailey was frightened to realize she couldn't move a muscle.

As the crimson energy surged around him, the whip in his hand began to writhe crazily like a hungry serpent. He raised the whip with a malicious look, then he lashed it out the next second.

A bloody crescent beam streaked through the air towards her. In that instant, she felt helplessness against this attack. Suddenly, a figure blocked her view in the last second. Then mobility returned, allowing her to fully raise her sword.

"Black star!"

From afar, one could see a black and crimson light flash towards each other. There was silence, and then a glaring light shone in all directions.

All color was lost temporarily, followed by a loud sound like a clap of thunder. In that moment, all perception was completely disrupted.

After that, the world finally returned to calm. With a clang, a sword fell to the ground. Hailey weakly dropped to her knees, a sigh of relief escaping her lips. The man was nowhere.

She gratefully looked to her side but then there was silence. She stared at the figure in stunned confusion, her mind blank.

"Hailey..." Sith muttered, his hands outstretched.

However, those hands crumbled into soot in the next second, allowing a silver jewelry to fall out. The sound of the bracelet hitting the ground was like a thud in her heart.

"Your magic. It was... beautiful."

She barely reacted to those words before his entire being crumbled and vanished in the wind.

***

[Hidden Mission Completed: A Romantic Sacrifice]

[Welcome to the Simping System]

[Objective: Become the Playboy Supreme.]