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The Playboy Challenge

The Playboy Challenge

Author: : Amaka Chi
Genre: Romance
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.

Chapter 2 Lenora chapter two

I was going through job listings on my phone when it rang, my sister's name made me curse. The last thing I wanted to do was talk to her. She'd probably seen the money I'd sent. With a sigh I accepted the call "Hey Ken"

"Thank you thank you thank you Len," she sounded so happy, I couldn't help but small "did you get a raise or something? You told me it'd take much longer to get the money"

And now she sounded suspicious. I chuckled, "chill out girl, I worked VIP on Monday. The tips were really sweet. I swear I can afford this"

"wish it didn't have to be a one time thing. How are you?"

Oh me? Just peachy. I swallowed, "I'm great"

Her pause was so long I thought she'd hung up,"you don't sound great. You sound the opposite of great. Lenora Adaline Gason, what the fuck are you hiding from me?"

I suppressed my groan,"it's nothing Ken. Leave it"

"I'm gonna call it"

"Don't you dare call it"

"Silas' circle circus," her voice was hard, angry, determined as she spat out the words that as kids had meant that we had to say the truth. As children, we had always known our parents didn't want us. They looked past us like we weren't there and avoided us as much as possible. We in turn, stayed out of their way as much as we could. Heather our birth giver would always remind us that if we made her mad she'd drop us off at the orphanage and we barely ever saw Simon Gason. Taking care of Kendall had fallen to me since she was born. We had always been all each other had. After weeks surviving on only sandwich, I'd had to learn and learn fast how to cook other things because even baby Kendall would scrunch up her face whenever she saw another sandwich. I'd learned to do our laundry, go the stores and keep us in good appearance so nobody ever suspected nobody was looking after us. And as soon as I was eighteen, we never saw any of our birth givers again. Ken had been just twelve. I'd sworn to do better by her than they had. We were both determined and hard headed. She could be determined to find out what was wrong but I was just as determined for her to achieve everything she wanted in life.

Fuck my life,"Don't interrupt me" and so I told her how Monday had gone down. At the end she was swearing up a storm.

"Look Len, I'm gonna come home. I'm gonna get a good job and we are gonna figure this out together"

"Like hell we are," this was exactly what I'd been afraid of "no, what we are gonna do is I'm gonna figure this out and you're gonna stay there and do whatever the hell it is they do there in med school"

"No-,"

"Don't fucking argue with me right now cause I'm telling you how it's gonna be regardless of what you think. I'm your older sister and I'm not gonna fail you. I never have and I won't start now"

"You can't do this alone"

"Well, so much for faith in me"

She growled,"don't talk to me about faith! I have faith in you. I've always had and I always will. I respect you Len and I'm in awe of how you've always worked it out and helped us pull through every shit. But I'm not watching you go down in ashes because you just don't know when to give up"

"I'm never giving up, hear that Len. I've gone too far to give up now dammit. We've both made sacrifices for this and-"

"No, we haven't. You've been the one putting your ass out there for me. Continuously. I live with a lot of guilt already. I'm not adding more to it"

"I- I didn't know that. And it doesn't matter. This is my choice. I'm choosing this"

"And this is my choice too. Or is it only your decisions that should be respected here?"

"Of course not Ken-"

"Then that's final. I'm packing my stuff and I'll see you tomorrow. We'll figure this out together okay? And when we are both in a better place I can come back to school. It's never too late, but I cannot in good conscience go on knowing that you're out there breaking your back for me over and over again. I can't do that baby. And you wouldn't want me to do that if you were in my shoes. I love you and you deserve a life too. You deserve more than working endless hours for me. I appreciate everything you've done for me. But no more. No more Len. Please," she sniffed.

I didn't even realise tears were falling from my ears till I made a little hiccuping sound, "God I love you so much but you're the most hard headed bitch in the whole world"

We both laughed watery laughs.

"I can't wait to see you," I confessed "I've felt so lonely and lost and empty of recent"

"You could have told me," she chided

"Well, you're not the only stubborn person in this duo," I teased

She snorted,"I'm sure I can out stubborn you I'm sure. Hey babe, I'll see you tomorrow. I've got to run okay..

"Okay"

After the line went dead I stayed curled up in bed for hours, numb. Somehow it felt like everything was falling apart and somehow it felt like everything was becoming fine too.

Kendall and I's reunion the next day was teary and soul soothing. I'd really missed my sister. It had been five months. Her hair had grown out and was a platinum pink now. Sometime when she was sixteen, she had outgrown me. At five feet ten my sister was a bombshell. She looked like a runway model and men often assumed she was just another pretty face, but she was whip smart and very opinionated. Her eyes were just like mine, big and bright hazel orbs, and the same milky complexion. But that was were the physical similarities ended. Even with all the weight I'd lost, my chest was still too full, my hips too wide.

"Let's go splurge for lunch. Eat out at some cheap, shitty restaurant. Stuff our faces with not quite healthy and too oily food. I don't want to think about our situation just for today," Ken bit her lips worriedly. My sister wasn't usually a worrier. I was the worrier of us two, so the fact that she was worrying made something in my heart clench. I was failing her.

I tried for a smile. "Sure." I knew she could see through the face I was trying to put up, but thankfully, she ignored it. I wanted to scream and rage. Life was so fucking unfair. Was there ever going to be a day when I didn't worry about bills? I needed a miracle and I needed it fast.

Chapter 3 Lenora 3rd chapter

I didn't believe in miracles, and at some point I'd lost faith in God. Why would I keep believing? Our parents hadn't been religious but I'd always believed that there was something more than us. Something out there that could protect us and love us like our parents had never done. As a child I'd gotten on my knees before my bed daily and talked to God. I'd seen a kid in a movie do it and things had worked out for her. After my parents left, I still tried to speak to God as often as possible.

After the first year of working as many odd jobs as possible and all the tears and loneliness that had come with becoming a mother to my young sibling, I'd sworn to never speak to a God who didn't care and I hadn't since then.

So when Kendall came home six days after she'd returned from school, with an envelope full of money, my heart had burst in pure joy. Had the God I'd abandoned finally proven himself?

"K-Ken? Where did you get that from?," I hadn't realized I was shaking till she clutched my hands.

She looked at me hard. Her expression was a mix of shame, defiance and determination. "I did something bad-"

"Oh my God Kendall! Did you steal the money? Who did you steal it from?."

She stood up sharply, "I didn't steal the money. Just listen"

I stood up too. "You have to return it"

"Will you just listen to me? I didn't steal it. At least not directly"

My head was racing with possibilities, "what does that even mean?"

"I got a job okay? I deliver drugs for this guy, Regan. The pay isn't much. Just enough to buy groceries and pay the phone bill and ride the bus. During one of my deliveries, I saw the code to a safe box. So I told Holly Kay. I swear that was all I did. I just said it in passing you know"

I had a good idea where this story was going, "no Ken. As a matter of fact I don't know"

"Holly Kay is the one who robbed the place okay. I didn't even know he was going to till he sent me my cut. It's twenty-five thousand dollars. I didn't even want to touch the money. I was going to return it to him but he's not picking my calls and nobody knows where he is"

"Probably dead!," I spat

"I haven't used a dime of it. I was going to return it Len! I fucking swear."

I sigh, collapsing back into my chair, "you obviously weren't going to tell me about this. What changed? Why did you withdraw it? Why now?"

I watch as her lips begin to tremble. That cannot be good. "Holly Kay just left a message. Apparently, the guys that we stole from were some sort of gang. And they caught one of Holly Kay's boys goofing around on camera, he sold us all out and they're coming for him. And me. He says I should disappear"

I could feel my heart pounding, my head throbbing. I tried to be calm and reasonable, "okay. No biggie. They won't cross state lines to look for you. Money like that is nothing to them. They'd probably find this Holly Kay and the rest of his crew, collect back their money and rough them up a bit. Worst case scenario, they find you, you return the twenty-five. Everything goes back to normal. Okay? Nothing's going to happen to you." Even as I said those words, I had a sick feeling in my guts that we were not in fact going to be okay.

So two days later just after I had put my head down to sleep after the long, tiresome day of endless shifts I'd had, our front door which wasn't all that sturdy to start with flew open with a crash. I didn't know what it was, hopelessness, acceptance, fear, numbness, exhaustion, madness, but I was calm as I threw on my hoodie and ratty sweat pants and stepped out into the kitchen/living room. Kendall flew out her door and into my back, clutching my shoulder and shaking with terror, I put my chin up and faced the two men who had stepped into our home. One was monstrously huge with a shaved head and a gleeful expression. Like the thought of ripping us limb from limb was the best thing ever. The other man was smaller, an inch or two taller than me and in a cheap suit. His blank expression gave me the creeps.

"You know why we are here." It wasn't a question.

I nodded slowly, "we have your money. All of it. Just take it and leave"

The smaller man's eyes narrowed. Then he nodded.

"Go bring their money," I said to Ken. When it was apparent she was too terrified to move. I unlatched her hands from their death grip on my person. I dragged her jaw down so she was eye to eye with me, "Ken. Go bring their money" she finally seemed to register what I was saying. She jumped into a flurry of movement, bolting into the miniscule hallway she had curtained off and called her room. Seconds later she was back, handing me the was of cash. I handed it to the smaller guy. He smiled,I recoiled, it made him smile wider.

"You see. We aren't bad guys," he said as he began to count the money "nobody likes being stolen from. We-" he stilled then looked up at me. Eyes going dark, "where's the rest of it?"

"The rest of it? That's it. Twenty-five thousand," I said shortly.

"Sweetheart. Don't you fuck with me. Holly Kay said he gave you thirty."

"No. He didn't. He's a lying piece of shit." Kendall barked

The smaller man shrugged as the bigger guy stepped forward. The room seemed to become even smaller.

"Sweetheart, you owe me five thousand. My boss expects me back by Monday with thirty. I'm not gonna hand him a cent less. So what are we gonna do about that? Cause it don't look like you're gonna be able to pay the rest before I leave on Monday. I can of course find a way to sell your other services to complete it," his suggestion was so obviously sexual even if I couldn't see the disgusting leer on his face. I'd rather die than sleep with this STI riddled piece of shit. And he wasn't going anywhere near my sister.

"I swear to God, twenty-five is all he gave me," Kendall's voice was full of panic now.

"God means nothing to me sweetheart. Make it fast Owen."

The big, bald monster stepped forward.

"No. Wait. Stop,"I cried out.

The smaller guy rolled his eyes, "we are here for your sister. It's got nothing to do with you"

"We'll get you the money Monday," Kendall suddenly declared

Everybody turned to face her. I was waiting for the smaller guy to snort or laugh but he just nodded "We'll be here Sunday evening. If you make me search for you. Owen will make it painful. I'd tell you to ask Holly Kay, but he's squashed brain on the side of a road right now. Have a goodnight sweetheart. See you Sunday." And just as suddenly as they'd come, they had gone. All the bravado that was holding me up dissipated and I fell to my knees.

What felt like hours later but was probably five minutes later,I stumbled in search of Ken. I found her kneeling before the toilet bowl, dry heaving. I held her head up and stroked her back. "It's alright,"I crooned "they are gone now."

Even though I knew that nothing was alright and we had merely postponed our demise. I had a hundred and four dollars to my name and that was from scrimping and saving. Ken probably had about the same or best case scenario, a tad more. But even combined, it was nothing close to five thousand.

"I know how we can make ten thousand," Ken said slowly.

I sighed ,"will you just let me worry about this please." I dragged her up to her feet and to the sink, turning it on. She obediently rinsed out her mouth.

"I put us in this mess. Allow me to get us out."

"Ken-,"

"This might sound really hare brained but it's something. And right now we have nothing. Isn't something, no matter how crazy it is, better than nothing. We have nothing to lose by doing this. And not like there are people out there clamouring to give us 5k by Sunday."

I scrubbed a hand down my face. My image in the mirror was so far from the girl I'd been a week ago that it was horrifying. My skin was entirely too sallow. My eyes sunken and ringed with blue circles. My lips were cracked and broken where I'd chewed them in anxiety. Even my hair that was normally too full and curly and hard to wrangle looked flat and colourless. "What is it?"

"Have you heard about Sheila Macallan?."

I wrinkled my brows, "No. Should I have?"

Kendall gave me a disgusted look "Her father is Gregory Macallan. Billionaire extraordinaire. The one that owns that resort in California we always fantasize about."

"Oh. That Macallan." You couldn't mention vacation without a Macallan service. Either their resorts, hotel chains, luxury cruise lines, car services or something equally as fancy.

"Yes. That Macallan. Sheila's his only daughter so she's extremely spoiled. Picture it, fancy cars, men throwing themselves at her, designer clothes, fancy sports cars, all of the trappings. Six months ago, Ian O'Malley, millionaire play boy broke up with her after a fifty-five day relationship. Nobody has ever broken up with Sheila Macallan before. She's always the one doing the breaking. So, well, she wasn't happy about the break up, but Ian won't take her back and all the men she's been hanging with have failed to grab his attention."

That sounded really stupid. "Can't she just forget about him?"

"Girls like that hate to lose. And she feels like she's lost. So she wants to get back at Ian. My roommate Tia told me all about it. It's this really exclusive thing. Anybody who can date Ian O'Malley for longer than fifty-five days and dump him publicly gets twenty thousand dollars. That's five thousand to pay off our debt and an extra fifteen. We can open our own cafe Len!"

I stare at her incredulously, "And you want us to what? Get into this competition esque rubbish? Ken baby, if Sheila with her billionaire dad and two hundred dollar hair cut couldn't keep this Ian guy for up to two months, who are we with our DIY hair cuts to do it?"

Her expression goes mutinous, "Uhm, two very attractive girls who are also desperate as fuck."

I shake my head "Who don't have up to fifty-five days to wile away trying to keep a man who doesn't want to be kept. We have less than forty eight hours to cough up five thousand. Or did you forget that part!" My voice is rising now.

"Well, I don't see you bringing up any other brilliant ideas. We won't know till we try. We'll meet up with Sheila Macallan, strike a deal or something. And if worse comes to worst, we'll record the meeting with her and sell it to some desperate tabloids looking for gossip."

I gasp in horror "Ken! We cannot put a billionaire's daughter in trouble"

"All press is good press to this people. And she can kill the story with her pocket change. Or we can threaten to sell it for five thousand. We are out of options. We cannot afford to have conscience or have deep thoughts about this right now. Life has been dealing us a shitty hand at every turn. It's high time we fight our horrible fate with some fire. I'm not going to lie around, crying and making myself sick with anticipation of how baldie is going to squash my head like a damn watermelon come Sunday night or how dude two is going to fuck me in the ass and slobber all over me. I'm doing this. So you're either with me or you're not, but I'm not changing my mind about this."

Fuckity, fucking hell.

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