
When A Stripper Falls In Love
Omotola Izobo · Ongoing · 65.2k Words
Introduction
Until she met Damon, a soulless billionaire CEO who doesn't believe in love. They had an unforgettable love-at-first-night experience.
It leaves Damon trapped in a one-year contract with a woman he doesn't love, and a pregnant stripper he can't ignore.
Could there be a deeper trauma behind Damon's aversion to love?
As their passion ignores, will they break free from their dark pasts and find a way to be together, or will they allow their current circumstances steal their only chance at happiness?
Chapter 1
Lisa
Staring at the reflection behind the large mirror in my room, the image of the woman before was unrecognisable.
She looked nothing like the woman I saw in this same mirror in this very room, exactly ten years ago.
Darker eyes. Slimer frame. Blurrier future.
My annoying ringtone broke me out of my daze. Annie was already screaming before my phone reached my ear.
“Girl! It's your birthday today!”
I didn't forget. The old me would have celebrated by locking myself up in her father's drawing room, sketching wedding gowns, and sundresses and fantasising about a trip to Paris.
But, the old me was long gone. I'd aged into a 26 year old woman with a sick father, a pile of bills, and zero time for dreams.
“Yeah I guess it is.” I muttered flatly.
“You guess? Oh no, there's no way I'll let you mourn your birthday like last year Lis. I'll be at your house in five. We are going out!”
She didn't wait for a response before she hung up. Classic Annie .Thankfully, I'd already washed up so I only needed to get dressed. Not that it mattered because Annie stormed into my room leaving me no chance to get dressed.
Her flaming ocean blue eyes locked into mine.
“Hi” I managed.
“Why aren't you dressed, I told you I was-”
“It's barely even five minutes.” I interrupted. “You literally just hung up!”
“I didn't think you'd be naked at 10am. Normal people are in front of their office desks as we speak.”
“First off, nothing about my life is normal. Second, I work at night.”
She rolled her eyes at me as she marched to my wardrobe. Big mistake. Annie's face was masked in horror as she stared down my rare collection of work clothes and casual pieces.
“What the hell, Lis. There's nothing decent in here!” she shouted.
I didn't bother replying. But you dear reader, and I know that I never told her it was decent.
“Fine.” She huffed, throwing her hands in the air in frustration. “Put these on. We're going shopping. And save the speech about being economical, it's my treat.”
My shoulders sagged lower. This really has to be the best day of my life. I pulled the dress on and tailed after her.
•••
After scampering around the mall like teenage girls, we picked a dress for the evening and a few others to add to my wardrobe.
“Kay, bitch! Let's paint the world red!”
When we got into the car, I finally asked,
“Annie, where are we going?”
“It's supposed to be a surprise.”
“I need to know. You know I still need to get to work this evening.”
“You don't. I'll pay you double for tonight. Consider it your birthday bonus. Live a little, Lis.”
“Fine.”
Her family owned the club I work at anyway so if she says it's a holiday, then it is. Guess it's one of the perks of working for your best friend.
When Annie finally pulled up in front of a luxury-looking restaurant, I realised she meant business. And when we got in, I was starry eyed. The aesthetics, layout, everything screamed luxur-ey!. It was the kind of place I avoided unless I got hired as a waitress or got dragged in by Annie, of course.
Honestly, this was the best birthday present ever because the only thing I love more than clothes is food.
Annie walked confidently and effortlessly commanding the attention of everyone in the room and I tailed closely behind her. We finally reached our table and took our seats. Unlike the waitress at the diner on my house street, this waitress seemed really happy to see us. I wondered why.
We had barely placed our order when we were interrupted by an angry guest.
“This is my reservation.” He barked angrily. “This is the table I was promised.” He shouted as his fist hit the table, spilling our complimentary drinks all over causing Annie and I to jump out of our seats.
The waitress from before ran across the room and made a polite attempt to calm him down,
“Sir, please, this must be a misunderstanding. If you could just calm-”
“I. Will. Not. Be. Calm! He said emphatically. “I was supposed to have a business meeting with a top client right on this spot. I will not be calm. This should be a negotiation table for a multimillion dollar contract not from some random girls to play dress up looking for a bed to warm at the end of the night.”
Without thinking my hand connected with his face.
“What the-”
I slapped him again, this time even harder.
“You do not speak to women that way. Don't you dare-”
I didn't get to finish before the doorman and a man I assumed to be the restaurant manager stepped in.
“Please Mr. Collins, our sincere apologies. Can you please come with me to my office to discuss this sir.”
He conceded but not without giving me a death glare on his way out.
“Lis, girl you were on fire!” Annie teased but my attention was focused on a man at the far end of the room who has a proud smirk on his lips. Had he been watching? I wondered.
“Yeah. I think I've lost my appetite. Can we just go home now?”
“No way. No worries. I have just the recipe to bring that appetite back.”
I watched her back as she whispered something to a hostess. Some more whispering before she signalled me to come along.
We were led through a door and inside? Inside was just too good to be true. From the sleek decor, to the breathtaking view of the bustling city of New York, to the cool hum of classical music, it was pure bliss.
Annie really went all out, a private room, just for us. Or so it was until we got company much later.
Annie didn't seem to be bothered or surprised by it. So we spent the rest of the evening eating and catching up. She had a pretty good sense of humour and was quite the entertainer so there was no dull moment. Yet, my eyes kept travelling across the room, landing on the silhouette of the man sitting by the window across the room. He was the same man from earlier
It had become a habit. I wanted to stop but it was almost addictive. I just couldn't. My wine glass was below my nose when his eyes finally met mine for the second time tongoht. My face turned red involuntary from being caught red-handed and Annie's voice faded out.
I didn't realise that she had stopped talking and left our table until she returned with the stranger by her side. His eyes were still on me. This time his gaze was dark, sharp, and almost predatory crawling over my skin.
I tried to distract myself by focusing on the soft glow of the city lights behind him but it wasn't enough to stop my stomach from tightening.
Annie broke the spell with a knowing smirk on her face,
“Damon, meet my best friend Lisa. Lis, he's Damon Astor, he's a close family friend, business associate, whatever.” She muttered breezily.
He raised a questioning brow to Annie in response and a smile threatened to break his stoned expression when he said, “Nice to meet you.” He took a pause before adding in a smooth voice that made my insides melt, “Lisa.”
“Yeah. Same.” I rushed. My voice sounded huskier than I would have liked.
I became hyper-aware of how much I didn't fit into this room. Into Annie's world. Into Damon's world. Damn. What was I even doing in this restaurant?
Oblivious of my queasiness, Annie went on, "Damon's joining us for dinner tonight.”
Damon sent another questioning look with a raised brow at Annie, “Am I now. What's the catch?”
“Oh.” She said, clapping her hands and sitting him into the next vacant chair. “ It's your treat.”
“I just knew it. You don't want my company, you only want my pocket.”
"You're a billionaire, get used to it. One dinner night won't cause any harm. You'll survive.” she said with a coy smile.
I settled into my chair although instinctively I felt the urge to run. Sensing Damon's eyes hovering around me was enough distraction. His presence just seemed to always command my attention. It was whispering into my ears, urging me to tilt my head and take another look but I didn't. Yet, I couldn't even hear a thing Annie was saying as she babbled on. The cooling unit was working perfectly fine but I was burning up internally.
I had hardly looked at the menu when the waiter waltzed to our table. And it took me another moment to notice that he was a chef not a waiter. Thankfully, Annie placed an order for us both and I emptied my wine glass in one go to help me unwind.
Just when I thought I had my act together, he spoke, again, "So, Lisa." He started. "I heard from Annie that you're an artist."
I instinctively sent her a look before smiling and saying, “Not anymore. I used to be but I have other responsibilities, and I don't even have the time like before."
He reclined in his chair and studied me intently like he was trying to figure me out. He seemed curious for more information but thankfully, he didn't press further.
"Now what do you do?" He asked.
"I uh…” I paused for a moment. Do I tell him I'm a stripper? Alright, show’s over Cinderelly. Guess it’s time for me to stop dreaming. Regardless of how I feel, CEO’s don't date strippers. Looking at Annie, who appeared to be quite intrigued by her glass of water, I replied,“I work at one of her family's clubs.”
Annie threw me a shocked look. Was she expecting me to lie about it? Damon's jaw tightened but he didn't say anything. Was he judging me? All the butterflies from before immediately disappeared. I was pissed and Annie knew it so she stepped in and changed the subject
For the rest of the evening, I couldn't shake off the nagging feeling that Damon had already sized me up—and found me unworthy.
However, after we parted ways at the end of the night I realised that a part of me wanted to be worthy.
It felt like a dangerous move, like belly dancing on the edge of a cliff.
Yet, I didn't want to step back—I wanted to dance and keep dancing forever.
Last Chapters
#55 55
Last Updated: 1/19/2026#54 Brand New Chap
Last Updated: 1/19/2026#53 No more hiding in metaphors. The poems had done their job.
Last Updated: 1/19/2026#52 New Chapter
Last Updated: 1/19/2026#51 Chapter xcx
Last Updated: 1/19/2026#50 Chapter 49 - It was supposed to be a silly afternoon in a Shakespearean library. But love has a way of rewriting the script.
Last Updated: 1/19/2026#49 Chapter
Last Updated: 1/19/2026#48 Chapter 48 - The Feelings She Never Wanted
Last Updated: 1/19/2026#47 Chapter 47 - From chaos to celebration—Lisa’s well-earned moment
Last Updated: 1/19/2026#46 Chapter 46 - Everything sparkled, except for the dull ache in my chest
Last Updated: 1/19/2026
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