Cherreads

The Casanova Tycoon

Vikram_0477
14
chs / week
The average realized release rate over the past 30 days is 14 chs / week.
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Synopsis
Adrian Cole died at thirty-eight with everything and nothing. A legendary playboy who burned through millions on parties, supercars, and beautiful women—only to crash and burn with three models in his backseat. His final thought was a bitter joke: "I had all the fun but built nothing that lasted." Then he wakes up at twenty-two. Hungover. Broke. Back in his college dorm in 2019 with $2,300 to his name and a second chance he never asked for. But this time, he's not alone. A mysterious system appears with one absurd mission: seduce powerful women, build a business empire, and have maximum fun doing it. The Casanova Empire System doesn't just reward charm—it weaponizes it. Every romance unlocks business opportunities. Every relationship brings family drama, hilarious chaos, and empire-building potential. From heiresses to CEOs, actresses to tech geniuses, each woman Adrian wins over becomes a pillar of his growing fortune. But juggling multiple relationships while building a corporate dynasty? That's where the real comedy begins. Can a playboy who lost everything become the tycoon who wins it all—one heart at a time?
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Chapter 1 - The Billion-Dollar Hangover

Pain.

It felt like a sledgehammer was remodeling his skull.

Adrian Cole gasped, his lungs burning as if he had just inhaled smoke. His hands clawed at the bedsheets, expecting the cold, twisted metal of a wrecked Ferrari. He waited for the explosion. He waited for the heat. He waited for hell.

But instead of fire, he smelled… pepperoni?

"Bro, turn off the alarm. You're gonna make me fail my raid."

The voice was muffled, coming from under a pile of dirty laundry across the room.

Adrian opened his eyes. The light was blinding. He wasn't in a burning supercar on the highway to Monaco. He was staring at a cracked ceiling fan that wobbled dangerously with every rotation.

Where the hell am I?

He sat up, his head spinning. This room. The peeling beige paint. The poster of a bikini model that was peeling off the wall. The pyramid of empty beer cans on the desk.

"Dorm 304," Adrian whispered, his voice raspy.

He looked down at his hands. They were shaking, but they were… unscarred. No Rolex Daytona on his wrist. Just a cheap rubber band. He touched his face. No beard. Smooth skin.

He scrambled out of bed, tripping over a discarded pizza box, and stumbled toward the small, dirty mirror attached to the wardrobe.

The face staring back wasn't the tired, 38-year-old billionaire who had just driven his car off a cliff. It was a kid. A handsome, wasted, 22-year-old kid with messy dark hair and eyes that looked like they hadn't slept in three days.

He grabbed the phone lying on the desk. It was an old iPhone X.

Date: September 14, 2019.

"No way," Adrian muttered, a manic grin starting to form on his lips. "No. Fucking. Way."

The memories hit him like a freight train. The crash. The screaming models in the backseat who didn't even know his last name. The sudden, crushing realization as the car flipped—that he had conquered the world but died with nothing real.

I had the money. I had the women. But I was a joke.

He looked at the calendar again. 2019.

Before the pandemic. Before the Tech Crash of '24. Before he made his first billion. Before he lost his soul.

"Adrian, seriously, are you high?"

The pile of laundry moved. A head popped out—round glasses, messy hair, and a hoodie that hadn't been washed in weeks.

Tubby Tom.

Adrian stared at his old roommate. In his past life, Tom had dropped out, moved back to his parents' basement, and Adrian never saw him again. He had ignored Tom's calls for years.

"Tom," Adrian said, his voice surprisingly steady. The panic was gone. Replaced by the cold, sharp calculation of a CEO. "What's my bank balance?"

Tom blinked, adjusting his glasses nervously. "Uh? How should I know? You spent the last of it on that bottle of Grey Goose last night. You said, and I quote, 'Rent is for peasants'."

Adrian grabbed his wallet. He counted the cash. Three wrinkled notes. He checked his banking app.

Balance: $2,314.50

He laughed. A short, sharp bark of laughter.

In 2030, this wouldn't even cover his lunch tip. But right now? It was seed capital.

He walked to the window and threw it open. The campus air rushed in—fresh, full of potential, and smelling of freshly cut grass. Students were walking below, oblivious to the fact that a shark had just swum into their goldfish pond.

He leaned against the frame, crossing his arms. His posture shifted. The slouch of the 22-year-old party boy vanished. He stood with his shoulders back, chin up, radiating an aura that felt too big for this cheap room.

I'm back. And this time, I'm not just going to play the game.

I'm going to own the casino.

[DING!]

The sound wasn't from his phone. It came from inside his head.

A translucent blue panel, crisp and high-definition like a hologram, unfolded in the air directly in front of his eyes.

[SYSTEM INITIALIZATION COMPLETE]

Host Detected: Adrian Cole Mental Age: 38 Physical Age: 22 Core Regret: "I had all the fun but built nothing that lasted."

Adrian didn't flinch. He had seen VR tech in 2030 more advanced than this. He simply raised an eyebrow. "A System? Really? Did I get Isekai'd into a bad novel?"

The text on the screen shifted, scrolling rapidly.

[Calculating Karma...][Converting 'Regret' into 'System Credits'...]

CONGRATULATIONS! You have unlocked the Casanova Empire System.

Life is a transaction. Love is the currency. Power is the product.

A second window popped up, flashing with gold borders.

[MAIN QUEST: THE REBOOT]

Objective: Establish your dominance on the new map. Target: Seduce the "Ice Queen" of the Business Department. Time Limit: 7 Days. Reward: Stock Market Prediction Tool (Level 1). Failure Penalty: Permanent Erectile Dysfunction.

Adrian stared at the penalty. He blinked twice.

Then, he threw his head back and laughed. It wasn't a happy laugh. It was the laugh of a man who had just realized the universe had a twisted sense of humor.

"Impotence?" Adrian wiped a tear from his eye. "You want to play hardball? Fine."

He looked at his reflection in the window. The faint golden ring glowed in his pupils for a split second—the System Glint.

"Tom," Adrian said, turning around. "Get up. We're going out."

Tom groaned, pulling the blanket over his head. "Bro, it's Saturday morning. Where are we going?"

Adrian smirked. It was that signature look—the "Know-It-All" Smirk that had made competitors weep in boardrooms.

"To class," Adrian said, grabbing his jacket. "I have a date with an Ice Queen."