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The Playboy Challenge

The Playboy Challenge

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Title: THE PLAYBOY CHALLENGE Genre: romance Trope: billionaire, play boy. Blurb: Lenora's life was going downhill quickly. From being fired at her work to being about to be evicted from her apartment, she is exhausted with her life of utter misery. The icing on the cake is when a dangerous man sends his two goon sniffing after her and her sister. They can either find a way to get five thousand dollars in three days or become shark food. A miracle comes in the form of a billionaire's daughter with a bruised ego. The plan is simple, if Lenora can keep billionaire playboy Ian O'Malley's attention for sixty days followed by a humiliating, public break up, she gets enough money to turn her life around. It's supposed to be a simple plan, and she's never meant to start feeling things for the charming billionaire. She can't mix business with emotions, but she's never felt this way before. What happens when a money making scheme with a looming end date begins to feel too real?

Chapter 1 Lenora

I was mad as hell.

Mad at myself.

Mad at my shitty parents.

Mad at my shitty ex Brandon.

Mad at the whole fucking world.

Currently, I was broke, hungry, exhausted from working two jobs and feeling really disappointed in myself. Where was the girl who had had great hope for the future? The girl who had promised to protect her younger sister? The girl who had told said younger sister to pursue her dreams cause she was always going to support her? That girl was buried under a boat load of reality and life's shittiness. It was like a fifty pound cloak weighing me down.

I pinched the extra space in my slacks. Space that hadn't been there last week. I held out my arms for the mirror and released a mournful breath. I was loosing weight I couldn't afford to lose. My arms looked like sticks poking out a snow man's sides. With another sigh, I pulled my hair up into a tight and efficient ponytail. I needed a haircut. Maybe after work if I could still stand straight, I'd give it a few snips with my scissors. Nothing like poverty to turn you into an all rounder, DIY queen and budgeting boss bitch.

I gave myself one last cursory glance, tearing my eyes away from all the itty-bitty imperfections, like the large, dark circles around my eyes that even concealer couldn't cover, the pallor of my skin, the scratches on my arm from wrangling Mrs Doreen's hellish cats. With a cheerful nod that I didn't feel, I grabbed my purse and left for work. Another shitty Monday trying to be nice to a bunch of over entitled girls with too much money and too much make up, grabby men and teenagers with stupid ass fake IDs trying to play men. The glamorous job of a bar waitress.

The train was just pulling in when I arrived. It was exactly twenty two minutes to my stop and then a four minute walk to the club. I knew better than to be walking that short distance to the club, but so far, nothing had ever happened to me. I'd even become passing friends with the two buff women who were sat on the tail of a red truck smoking everyday I walked by. Sometimes I suspected that it wasn't just a habit. Maybe they sat there for me. Wishful thinking, but who was going to disabuse me of the notion? If I didn't have these little comforting thoughts to fall back to, I'd have worried myself into an early grave.

"Hello doll," the greeting was right on cue. The women were sitting on the tailgate as usual. One of them had super long bottle red hair, the other had shorn, dark hair. They looked alike or maybe just had similar builds. I could never see much of them in the dark street.

I tipped my head up "hey"

"Have a nice night love"

"you too"

And that was it, the same greeting every night. It should have been weird, but instead, it was somewhat of a comfort.

I slipped in through the rear door of the club building, nodding at Sam who was throwing out the trash. I wasn't really friends with my co-workers. I had always been a loner, not much room for friendships and Friday night hang outs when you worked the amount of hours I worked and was dead to the world the rest of the time. I didn't think I even knew how to take a break or let loose anymore. What would I even contribute to a conversation on a girls' night out? 'oh em gee! You should have seen me on Thursday as I cleaned out this room. There were fifteen used condoms in the waste basket! Ain't that something' that'd definitely be a riveting conversation.

I dumped my bag in the locker at the back, changed out of my slacks and worn converse shoes into the mini-skirt and fuck me pumps we had to wear. My buttons were undone to nearly my stomach and my hair was let loose. I had a great rack that kept the tips coming even though sometimes I'd rather slice my wrist than let those creeps look down my top. Trying for a look that wasn't a combination of miserable and destitute, I sauntered out to the bar.

It was still early so the place was quite empty. A few people lingered at the bar, a couple or two swaying to the music on the floor.

"Head on up to VIP, Molly isn't here yet," Jared said as I approached the bar. He was the manager and a generally nice guy and fair boss. I nodded and made to walk away when he suddenly grabbed my arm and leaned forward "we are under a new ownership"

"What? Mr Cash would never sell. This place is his baby," my head swam with this info. Were we all going to be laid off? I couldn't afford to lose this job.

"No no no. Nothing so dire. Trust me. And he didn't sell. He lost it in a bet. Just be careful up there. The new owner might be up there, checking out his investment or something"

I nodded, even though I highly doubted it. It was way too early in the night for anyone of substance to be here. If the new owner wanted to check out his investment, the best time would be closer to midnight when the place would be packed or even better, on Friday night. That was the busiest night of probably every club or night establishment. Work was calm that night. The VIPs were more respectful and Molly didn't show up so I was raking in a lot of tips. Enough money to send my baby sister, Kendall for her upcoming rent money. I was feeling so fucking elated that when someone cupped my breast in their hands and squeezed, it took me a second to blink and then flinch away.

The creep looked like he was fresh out of college. Early twenties with a too slick look. Trust fund baby in a too expensive suit, too much hair product and cloying cologne. He had been watching me all night and I'd ignored it. More fool I.

"Come on baby. Sit on daddy's lap" he smirked

I felt like I'd just thrown up in my own mouth. "uhm, no thanks"

His face went hard "don't be a prude. Sit the fuck in my lap"

What did this punk think this was? Some shitty mafia movie or something?"I'll pass"

I turned to walk away, suddenly my hair was snatched and I was being yanked backwards. I didn't even think, one second I was falling backwards, probably unto obnoxious asshole's lap, the next there was a smashing sound, a bowl of pain and I was released, staggering till I caught my footing. I whirled around. The VIP area had gone quiet. The asshole was yelling and yowling like I'd stabbed him in the brain. I wanted to roll my eyes.

"You fucking bitch. You're fired"

Aaaaand that was how I learned that he was the new owner. His father actually was, but he had put the bar in his son's hands, probably to teach him some responsibility. I was given an envelope of fifty dollars by Jared and a pitiful smile. The only reason charges weren't being pressed was because the asshole didn't want to bring his father's attention to the club this soon. I was fucked and not in a good way. I was shivering in my miniskirt as I walked home because I hadn't even been given the chance to change back into my pants.

"A little bit too early to be going home," the other woman wasn't there, just the redhead one.

I shrugged, "goodnight"

She sounded hesitant when she said goodnight.

I still had my job as a hotel cleaner, but it could barely afford groceries and my boss was a grade A asshole who was out for my blood. I didn't know how much longer I could work there. He was constantly looking for an excuse to get rid of me. Finding a new job would be close to impossible and I couldn't let my sister realize how bad it was or she'd insist on leaving school. I knew her, and as much as she wanted to be a doctor, she also had a bleeding heart and would never tolerate me working to the bone so she could live her dream. I could probably become a sex worker or something, I don't know, find some rich older guy to hitch myself unto, but I had only had sex with one guy in my life which was my shitty ex and I had just tolerated it. It wasn't something I particularly liked. I only put up with it cause I'd loved or at least thought that I'd loved Bran.

Holding back my tears only lasted till I got into my building, then I broke down on the staircase cause the elevator was always having problems and I cried my goddamn eyes out.

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Latest Release: Chapter 43 43 Chapter   Yesterday 15:10
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1 Chapter 1 Lenora
22/03/2024
6 Chapter 6 Ian
22/03/2024
7 Chapter 7 Lenora
22/03/2024
9 Chapter 9 Lenora
22/03/2024
10 Chapter 10 Lenora
22/03/2024
11 Chapter 11 Ian
22/03/2024
13 Chapter 13 13 chapter
03/05/2024
14 Chapter 14 14 chapter
03/05/2024
16 Chapter 16 16 chapter
07/05/2024
17 Chapter 17 17 Chapter
07/05/2024
18 Chapter 18 18 chapter
07/05/2024
20 Chapter 20 20 chapter
07/05/2024
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