Picking Up Girls With My Pickup System-Chapter 9: The Wolf Circles.

Kent trudged into his history classroom, his bag slung low on his shoulder. Normally, this room felt dull—chalk-dusted air, faded maps curling at the edges, and a teacher who lectured in monotone like he was allergic to enthusiasm. But today? The walls felt tighter. The floor heavier.

The whispers had arrived before he did.

"That’s him—yeah, Gilbert."

"Did you see what happened with the barista?"

"No way that was real. She was probably just being nice."

"Derek was watching, though..."

Kent clenched his jaw and slid into a seat halfway back. His plan was simple: keep his head down, scribble fake notes, and maybe the universe would forget he existed.

But then—the air shifted.

Heavy footsteps echoed against the tile. Each one louder than it should’ve been.

Kent didn’t have to look. His skin already crawled.

Derek.

The guy carried presence like a storm front. He didn’t yell or shove—he didn’t need to. Just walking into a room bent the mood around him. His friends trailed behind, smirking like hyenas, but Kent only felt the weight of one set of eyes.

Sure enough, when Derek strolled past the desks, he didn’t take his usual spot near the windows. He stopped right behind Kent.

The chair creaked as Derek sat down.

Kent’s heart thudded. His pen scratched against the notebook in meaningless lines. Don’t look back. Don’t turn around. Maybe—

A low voice slid through the space between them.

"Well, well. Gilbert."

Kent’s spine stiffened.

"You’ve been busy," Derek murmured, just loud enough for Kent to hear over the rustling of papers. "Real busy."

The back of Kent’s neck prickled as if a predator’s breath lingered there.

He forced his pen to move, but the ink blotched. His hand trembled.

He saw everything.

And he wasn’t going to ignore it.

Kent’s pen slipped in his grip, smearing ink across the page. Derek leaned forward, elbows planted on his desk, his voice a low growl just above a whisper.

"You know..." Derek drawled, "a guy could get hurt running his mouth like that."

Kent swallowed. "I—I wasn’t—"

"Shh." Derek tapped the back of Kent’s chair with one finger, rhythmic, like a ticking clock. "Don’t explain. Just listen."

The classroom wasn’t loud enough to drown them out. A couple students in the nearest rows shifted uncomfortably, pretending to focus on their books but clearly eavesdropping. Kent felt their eyes flicker to him and back.

Derek’s tone dripped with casual malice. "I don’t like it when people play games with what’s mine."

Kent froze.

Lena. He was talking about Lena.

"But hey," Derek continued, a mock-friendly chuckle rumbling from his chest, "maybe you didn’t know better. Maybe you’re just... stupid."

Kent’s knuckles whitened around his pen. His mouth went dry.

"Here’s what’s gonna happen," Derek said, his voice like gravel dragging across Kent’s nerves. "You keep your head down. You keep your mouth shut. And maybe—maybe—you walk out of this year with all your teeth."

The finger tapping on Kent’s chair stopped. The silence hit harder than the noise.

Kent’s pulse pounded so loud it drowned out the teacher’s lecture. He wanted to vanish. To crawl under the desk and disappear.

But then—

Ding!

A familiar screen flared in his vision.

[New Mission Unlocked!]

[Verbal Duel: Outwit Derek without backing down.]

[Reward: +2 Confidence, Reputation +3.]

[Failure: -2 Confidence, Reputation -5.]

Kent almost groaned. Outwit Derek? In front of half the class? His stomach lurched.

But the words "without backing down" blinked insistently, like a dare.

His shaky reflection stared back from the glossy desk surface.

If I choke now... I’ll never recover.

The mission text pulsed like a countdown timer in Kent’s vision.

[Outwit Derek without backing down.]

Kent’s throat tightened. His instincts screamed: stay quiet, survive. But the System wasn’t giving him a choice.

[Penalty countdown initiated: 3... 2... 1...]

Kent panicked. "W-well, I’d keep my mouth shut..." he blurted out, voice cracking.

Derek smirked. "Good boy."

"...but then how would people hear me laugh at your haircut?"

The words slipped out before Kent even realized what he’d said. His stomach dropped—oh no, oh no, oh no—

The class went silent.

Then, a few muffled snickers broke the air.

Kent blinked. He hadn’t meant to say it, but the System screen lit up:

[Skill ’Quick Wit’ Activated.]

[+5% Charm Bonus Applied.]

[Success: 1st Insult Landed.]

Derek’s smile froze. His fingers drummed once on Kent’s chair. "What was that?"

Kent’s pulse hammered. His tongue felt possessed, words spilling without hesitation. "Sorry, did I say haircut? I meant helmet. Didn’t realize the football team issued those for class too."

This time, the laughter was louder. A couple of kids at the back even clapped their hands over their mouths.

Kent’s eyes widened. I... I just said that?

Derek leaned back, jaw tightening. His friends glanced at each other, unsure whether to laugh or glare.

The teacher finally glanced up from his notes, brow furrowed. "Something funny back there?"

"No, sir," Derek muttered, still glaring at Kent.

Kent sat frozen, heart in his throat. But the System chimed:

[Verbal Duel in Progress. Score: Kent 2 – Derek 0.]

For the first time in his life, Kent wasn’t just surviving Derek’s attention. He was winning. 𝙛𝒓𝓮𝒆𝔀𝒆𝙗𝓷𝒐𝙫𝒆𝙡.𝒄𝓸𝓶

Derek leaned forward again, his voice low, dangerous. "You’ve got jokes, huh? Cute. You think making people laugh is gonna save you?"

Kent’s insides twisted. His survival instinct screamed shut up!—but the System’s text pulsed again:

[Respond: Don’t retreat.]

Kent swallowed hard. "Save me? Nah. But it might save everyone else from having to look at your face too long."

Gasps. A ripple of laughter shot through the room.

Derek’s jaw ticked. His eyes narrowed into slits.

"Careful, Gilbert," Derek said, louder now so more could hear. "You’re still just a nobody. Everyone knows it."

The words stung—because they weren’t wrong. Kent was a nobody. A background blur in other people’s lives. But the System chimed in his ear:

[Quick Wit Suggestion: Turn the label on him.]

Kent’s lips moved before his brain caught up. "And yet, here you are, Derek—Mr. Popular—spending all your time talking to a nobody. Guess that makes you what, exactly?"

The class burst out this time. A couple kids actually slapped their desks. The teacher barked for silence, but the smothered giggles wouldn’t die.

Derek’s face flushed a dangerous red. He gripped the edge of his desk so hard Kent thought the wood might crack.

The System pinged gleefully:

[Verbal Duel Score: Kent 4 – Derek 1.]

Kent sat there, still shaking, but... alive. Stronger, even. Each laugh felt like fuel in his chest.

Derek leaned closer, close enough that Kent could feel the heat of his breath. "Enjoy it, Gilbert. When class ends, you’re dead."

The laughter drained from Kent’s veins. His stomach dropped again.

The System stayed silent this time. No suggestion. No comfort. Just that lingering mission text:

[Outwit Derek without backing down.]

******

The bell shrieked, cutting the tension like a blade. Chairs screeched as students bolted for the door, buzzing with barely contained laughter and whispers.

"Dude, did you hear that?"

"Gilbert roasted him!"

"No way Derek lets that slide..."

Kent sat frozen in his chair, his notebook a mess of ink smudges and half-formed doodles. His hand still trembled, the adrenaline refusing to leave.

Derek rose slowly, every motion deliberate, his fists curling at his sides. His friends watched him carefully, waiting for a signal. But Derek didn’t swing. He didn’t shout.

Instead, he leaned down, his lips almost brushing Kent’s ear. "Enjoy your little moment, Gilbert. It’s the last one you’re getting."

The words slithered under Kent’s skin, colder than a fist ever could.

Derek straightened, his chair scraping loudly as he shoved it back into the desk. He strode out of the classroom, his posse trailing behind, their eyes promising retribution.

Kent exhaled for the first time in minutes, his body sagging. He wanted to collapse into the floor. But then—

Ding!

A glowing screen lit up before his eyes.

[Mission Complete: Verbal Duel]

[Reward: +2 Confidence]

[Reward: Reputation +3]

[Bonus: Skill Upgrade — Quick Wit (Lv.2)]

Kent blinked. "Level two...?"

[Quick Wit (Lv.2): 15% increased chance of successful comebacks. Enhanced timing.]

He stared at the notification, a swirl of disbelief and giddy panic battling inside him. He had just—what? Outsmarted Derek? In front of everyone?

A girl brushing past him muttered, half to her friend, "Didn’t think he had it in him..."

Kent froze. People had noticed.

For once, not as a background nobody.

But as he shoved his things into his bag, Derek’s words echoed, chilling him to the bone:

It’s the last one you’re getting.

Kent tightened his grip on his strap.

The System gave him confidence, sure. But could it stop fists?

He wasn’t sure he wanted to find out.