Cheating My Way Through Marvel and Beyond

Jack barely had time to process his insane roulette win before he heard a familiar voice.

"Oh, come on, number 2 is such a lonely number. If it were me, I'd go with number 3."

Jack turned his head and was greeted by a sight that could make even the most disciplined monk rethink his vows.

Natasha Romanoff.

The Black Widow herself.

This time, she wasn't wearing her usual tight, deadly leather. Instead, she had on a two-piece dress—white on top, light blue below. The slanted hem of her skirt had a sheer veil trailing just below her knees, teasing glimpses of her long, sculpted legs with every movement.

Compared to the sultry allure she radiated at the bar, tonight she looked almost innocent—almost. But here, in a casino flooded with women flaunting skin-tight dresses and barely-there outfits, her understated elegance made her stand out even more.

And judging by the way Tony Stark's eyes practically popped out of their sockets, Jack wasn't the only one who noticed.

"Hello," Tony said, flashing his most charming smile. "I'm sure you already know who I am, but let's make it official. Tony Stark."

Natasha turned toward him, giving a polite nod. "Of course. Who in this country doesn't know Tony Stark? Natasha. Natasha Romanoff."

Jack raised an eyebrow. No alias? Either she was getting cocky, or her cover was so deep that even if Tony tried digging, he'd come up empty.

After exchanging pleasantries, Natasha turned to Jack, smiling playfully.

"I'm sorry I left so suddenly last time at the bar. Tonight, I figured I'd make it up to you. How about we gamble together?"

Jack smirked. "Oh? So, you're buying me dinner first before stabbing me in the back this time? That's progress."

Natasha chuckled. "If I wanted to stab you, you wouldn't see it coming."

Jack laughed. "Fair point. Alright, let's play."

Without hesitation, Natasha slipped her arm through Jack's, pulling him along like an eager girlfriend dragging her boyfriend through a shopping mall.

The roulette wheel spun, the tiny iron ball bouncing around before settling.

Number 2.

Tony let out a loud "YES!" before realizing what just happened.

"Wait a minute," he muttered, turning toward Happy. "How many chips did I give him?"

"Uh… about $180,000, sir."

Tony smirked at Jack. "So you won about $6 million."

Jack grinned. "Huh. Beginner's luck."

"Yeah, right," Tony scoffed. "Hey, you should thank this beautiful lady. That was her bet, too."

Jack smirked. "I put up the capital, so we split it. Or, you know, you could just let her keep my share as a tip."

Natasha shook her head. "No need. I just came here for fun."

"Suit yourself." Jack casually deposited the winnings into his account.

Before leaving, Tony leaned in and whispered into Jack's ear.

"Tell me the name of that bar you always go to. I'll find you when I get back from Afghanistan."

Jack's playful smirk faded slightly. "Tony… be careful out there."

Tony gave him a cocky grin. "Always am."

Jack didn't press further. The events in Afghanistan were inevitable. Stark's journey to becoming Iron Man had to happen.

And now, Jack just had to see how his own role in this would unfold.

Caught in the Widow's Web

As Tony disappeared with a female reporter in tow, Jack turned to Natasha.

"Alright, let's cut the crap. You didn't just happen to run into me tonight, did you, Miss Romanoff?"

Natasha smiled but didn't deny it. "Okay, fine. I came here for you. But we can talk later. For now, let's play a little more."

She dragged him around the casino, placing casual bets at every table.

To Jack's surprise, they kept winning. Not huge amounts, but enough to rake in another $4 million.

When it was time to cash out, Natasha waved her hand dismissively. "I don't need the money. Keep it."

Jack pocketed the winnings without argument.

The two of them walked out of the casino and onto the brightly lit streets. The cool night air carried the faint scent of the ocean.

"It seems like you and Tony are close," Natasha noted.

Jack shrugged. "We get along. But I'd say it's even harder being friends with an elite spy who pretends to be a bubbly socialite."

"How did you know?"

Jack shot her a look. "Seriously? You show up at the back alley of a bar in the middle of the night and take down three grown men like you're on a warm-up jog. They were either assassins or agents. And since you didn't kill them… well, that narrowed it down."

Natasha smirked. "Not bad. But I have a question for you now."

"Go for it."

"How did you get the super serum? Was it because of Isaiah?"

Jack's smirk faltered. Damn. That was fast.

SHIELD's efficiency was terrifying. He'd barely been in a real fight, and they had already dug up the connection between him and Isaiah.

Jack didn't bother lying.

He explained what happened—the shooting, his survival, and how the serum seemingly fused with him.

Natasha listened intently. When he was done, she simply asked, "You think you're just lucky?"

Jack shrugged. "Wouldn't be the first time."

"Relax," she said. "We're not interested in replicating the serum. It's too unstable. And Isaiah? He's off-limits. In fact, we'll be keeping an eye out for anyone trying to mess with him."

Jack narrowed his eyes. "So what do you want?"

Natasha sat down on a bench, crossing her legs. "You."

Jack blinked. "Well, damn. That was fast."

She rolled her eyes. "Not like that, idiot. I mean, SHIELD is interested in you. Your skills, your potential… and your mindset."

Jack sat beside her, rubbing his chin. "So, what? You're here to evaluate me? Give me a personality quiz? What if I fail?"

"We don't arrest people for being strong," Natasha said. "But if you suddenly develop a god complex and decide to wipe out half the city, then yeah, we'd step in."

Jack leaned back, staring up at the night sky. "So, in other words, I just have to make sure I don't do anything too stupid?"

"Pretty much."

Jack smirked. "Damn. That's gonna be tough."

Natasha chuckled. "I'll be keeping an eye on you, Jack. Let's see if you're as interesting as you seem."

The two of them sat there, talking and bantering until late into the night.

But the next day, everything changed.

Jack received a call from Happy.

Tony Stark was missing.

Attacked by terrorists.

Jack let out a slow breath. So it begins.

He glanced at the system screen, half-expecting a notification.

Sure enough, a new mission popped up.

Mission Update: Assist Tony Stark in becoming Iron Man.

Bonus Objective: Fight Iron Monger (Obadiah Stane) alongside him.

Jack sighed, cracking his knuckles. "Fine. Let's get this party started."