The Undercover Heiress

The fluorescent lights of the Sterling & Co. flagship store hummed with a low, headache-inducing buzz. My father, Richard Sterling, CEO of the Sterling Retail Empire, had “banished” me here for the summer.

“Character building, Chloe,” he had said, sipping his scotch in our Manhattan penthouse. “You can’t run the kingdom if you don’t know how the peasants sell shoes.”

So, here I was. Chloe Sterling, heiress to a billion-dollar fortune, wearing a polyester uniform and kneeling on the carpet to fit a size 7 pump onto a customer’s foot.

The bell above the door chimed. I looked up and froze.

Walking in, hand-in-hand, were Tom and Jessica.

Tom was my ex-boyfriend. We had dated for a year in college. He was a finance bro with big dreams and a small wallet, always complaining about the cost of everything. I had broken up with him three months ago because I was tired of playing the “struggling student” role to protect his fragile ego.

Jessica was the girl he cheated on me with. She was petite, blonde, and wore her insecurity like a designer handbag.

Tom spotted me instantly. His eyes widened, then narrowed into a sneer.

“Chloe?” he laughed, a sharp, barking sound. “You work here? Selling shoes? I knew you were struggling after graduation, but I didn’t think it was this bad.”

Before I could respond, Jessica chimed in, her voice dripping with artificial sweetness. “Oh, hi Chloe! It’s so… quaint to see you. Actually, I need help. Can you fetch these in a size 7?”

She pointed to a pair of Italian leather stilettos. The price tag read $2,800.

I stood up, smoothing my uniform. “Those run small,” I said calmly. “And they’re $2,800. Are you sure?”

Jessica turned to Tom, pouting. “Babe, they’re so cute. And you just got that promotion at the firm…”

Tom puffed out his chest. He looked like a peacock trying to intimidate a lawnmower. “Of course, babe. Get them. Whatever you want.”

My coworker, Sarah, who knew about the breakup but not my identity, stepped forward. “I can help you with those.”

“No,” Jessica said, her eyes locked on mine. “I want Chloe to do it. Think of the commission! It’s probably more than Tom spent on you in a whole year, right Chloe?”

I laughed. I couldn’t help it.

“You’re not wrong,” I said. “Tom was always… frugal.”

I remembered the Valentine’s Day he asked my roommate to use her employee discount to buy me a gift. I remembered how my father had offered to give Tom a high-paying internship, and I had declined, wanting Tom to make it on his own. I had saved his ego, and he had repaid me with betrayal.

“Just get the shoes, Chloe,” Tom snapped, his face reddening.

“Actually,” I said, leaning against the display case. “We don’t have a 7. Only a 5. But these over here…” I pointed to a pair of sensible, beige pumps on the clearance rack. “…are on sale for $60. Much more in your budget, Tom.”

The air left the room. Jessica gasped. Tom looked like he wanted to punch me.

“You’re just jealous,” Jessica hissed. “Tom loves me. That’s why he spends money on me. Money follows love, Chloe.”

“Is that so?” I smiled. “Then I guess he didn’t love you enough to buy the right size engagement ring. I heard you had to pay for the resizing yourself.”

It was a low blow, but satisfying.

Tom grabbed Jessica’s arm. “We’re leaving. I’m calling corporate. I know the regional manager, Mr. Henderson. I’m going to have you fired, Chloe.”

“Please do,” I said. “Tell Mr. Henderson I said hello.”


Later that evening, I was walking out of the employee entrance. My vintage Vespa—a gift from my mother—was parked by the curb.

Or it had been.

Now, it was sitting on its rims. Both tires were slashed. Deep, jagged cuts in the rubber.

I sighed, pulling out my phone.

A sleek black Mercedes pulled up. Tom rolled down the window.

“Car trouble?” he asked, smirking. “Shame. That scooter looked… old anyway. Need a ride? My new C-Class has heated seats.”

Jessica leaned over from the passenger seat. “Oh, Chloe, that’s terrible. But maybe it’s a sign you should get a real car. If you can afford one.”

“I’m fine,” I said, typing a text to our family driver, Alfred. Flat tires. Bring the SUV.

“Suit yourself,” Tom revved the engine. “Enjoy the walk.”

They sped off.

A moment later, a gray sedan pulled up. It was Mr. Henderson, the regional manager.

“Miss Sterling?” he asked, looking panicked. “I saw you on the security feed. Is everything alright?”

“My tires were slashed,” I said. “Mr. Henderson, I need you to pull the footage from the parking lot cameras from the last hour. Send it to my personal email.”

“Of course,” he said. “Hop in. I’ll drive you home.”


The next morning, I arrived at the store to find a chilly atmosphere. My coworkers were whispering. When I walked into the breakroom, silence fell.

“What?” I asked.

“Everyone knows,” Sarah said quietly. “There’s a rumor going around on the company Slack. Someone filed an anonymous HR complaint against you. They said you were soliciting… favors… from management. Specifically Mr. Henderson.”

I blinked. “Excuse me?”

“They said you were seen getting into his car last night.”

I marched out of the breakroom and straight to the elevator. I pressed the button for the penthouse floor—the executive suites.

The doors opened, and there was Tom.

He was wearing his best suit, holding a leather portfolio. He looked surprised to see me.

“Chloe? You can’t be up here. This is for executives. And… special guests.”

“I’m going to a meeting,” I said, stepping into the elevator with him.

“You’re going to get fired,” Tom laughed. “Actually, I’m here to make sure of it. I have a meeting with Mr. Henderson. I’m the new junior consultant for the tech upgrade. I’m going to tell him about your… attitude.”

“Good luck with that,” I said.

“You know,” Tom continued, leaning in close. “Jessica told me about the HR complaint. Sleeping with the boss? Really, Chloe? I thought you had more self-respect. But I guess desperation makes people do crazy things.”

The elevator dinged. The doors opened.

“Mr. Sterling is waiting in the boardroom,” the receptionist said.

Tom straightened his tie. “Showtime.”

He strutted toward the boardroom. I followed.

“Chloe, stop following me,” he hissed. “You’re going to get security called on us.”

He pushed open the heavy oak doors.

Inside, the long mahogany table was filled with the company’s top brass. Mr. Henderson was there. So was the CFO. And at the head of the table sat my father, Richard Sterling.

Tom froze. He had expected a small meeting with a manager, not the entire board.

“Ah, you must be the consultant,” my father said, not looking up from his papers. “Sit down.”

Tom scrambled for a chair at the far end of the table.

Then, my father looked up. He saw me standing in the doorway.

“Chloe,” he said, his face breaking into a warm smile. “You’re late. Sit here.”

He patted the empty leather chair to his right. The seat of honor.

Tom’s jaw dropped. “Sir… I think there’s a mistake. She’s… she’s a sales associate. From downstairs.”

My father looked at Tom, then at me. “Sales associate? Chloe, did you forget to tell him?”

I walked over and sat down, spinning the chair slightly. “I thought it would be more fun if he figured it out.”

“Figured what out?” Tom asked, his voice trembling.

“Tom,” I said, “meet my father, Richard Sterling. Dad, this is Tom. My ex.”

The silence in the room was absolute. You could hear the hum of the air conditioning.

Tom turned pale. He looked like he was going to vomit.

“Sterling?” he whispered. “Chloe… Sterling?”

“Surprise,” I said.

Mr. Henderson cleared his throat. “Miss Sterling is here representing the family interest in the new retail expansion. She is effectively… your boss.”

Tom slumped in his chair.

“Now,” I said, opening a folder on the table. “Before we discuss the tech upgrade, we have an internal matter. Mr. Henderson, did you get the file?”

“Yes, Miss Sterling.”

“Put it on the screen.”

The projector hummed to life. On the massive screen, a grainy black-and-white video played. It showed the employee parking lot. A figure in a hoodie walked up to a vintage Vespa. The figure looked around, pulled out a knife, and stabbed the tires. Then, the figure pulled down their hood to wipe sweat from their forehead.

It was Jessica.

“That,” I said, pointing at the screen, “is Jessica Miller. Tom’s girlfriend. Vandalizing my property.”

The board members gasped. My father’s eyes went cold.

“And,” I continued, “I traced the IP address of the anonymous HR complaint filed against me this morning. It came from a residential address in Queens. Tom, isn’t that your apartment?”

Tom was shaking. “I… I didn’t…”

“You filed a false report accusing me of sleeping with Mr. Henderson to cover up the fact that your girlfriend slashed my tires because she was jealous,” I said. “That is defamation. It is harassment. And it is a fireable offense.”

“Get out,” my father said. His voice was quiet, but it carried the weight of a guillotine.

“Sir, please,” Tom begged. “I didn’t know! Jessica… she’s crazy! She made me do it!”

“You tried to ruin my daughter’s reputation,” my father said, standing up. “You are banned from all Sterling properties. If I see you near Chloe again, I will bury you in so many lawsuits your grandchildren will be paying legal fees. Get. Out.”

Security guards appeared and dragged a sobbing Tom out of the room.


That night, the company gala was held at the Pierre Hotel. I wore a custom gown—$12,000, not that I was counting.

I stood on the balcony, holding a glass of champagne.

Below, on the street, I saw a commotion.

Tom and Jessica were there. They were arguing. Jessica was crying, her mascara running down her face. Tom was screaming at her, waving his arms.

“You ruined everything!” I heard him yell. “I lost the contract! I’m blacklisted!”

“You didn’t stand up for me!” Jessica screamed back. “You coward!”

Tom raised his hand, as if to strike her.

I didn’t flinch. I pulled out my phone and texted security. Problem on the sidewalk. Handle it.

Two massive bouncers moved in, separating them. Tom was shoved into a cab. Jessica was left standing alone on the curb, sobbing into her hands.

My father stepped out onto the balcony. “Everything okay, sweetheart?”

“Everything is perfect, Dad,” I said.

I took a sip of champagne.

The summer was over. The lesson was learned.

Never underestimate the girl selling shoes. She might just own the pavement you’re walking on.

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