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In Love with the Playboy

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mtçh
50
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202
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Summary

All her life, she has kept away from the opposite sex. But they want is to fulfill the ultimate goal while she still wants to remain chaste and holy. Its not awesome to have five hot following you around because of a bet and they want your virginity. I tell you, its not. Its scary. Meet Bailey Hadid, nerdy Bailey with the glasses. Last year at high school and she expects it to be normal just like every other kid but this is different all because of a bet. Wait, What bet? The bet ongoing between five friends. The first among the players that takes Bailey's virginity will win the bet and of course, there had to be pictures to prove it. And its not gonna be easy for Bailey when the players are the hottest guys in school and they want to fulfill their last goal, to get into Bailey's pants. V-destroyers on patrol. With these five friends determined to win the title of The Ultimate Virginator, will our Bailey make it out alive with her virginity? What's gonna happen when they all cross paths in order to win her V-card because of a bet? What if one of the players falls in love? Will someone's heart get broken?

EmotionRomanceTrue LoveYoung AdultPlayboyStudent

Chapter 1

Bailey's POV

"Good morning bestie". Katie's voice rang out as I walked out my room to the door.

"Will you try to keep your voice down little bit, it is the first day of school, ya know".

She rolled her eyes. "Whats so special about the first day of school?".

"Nothing. Just wanted you to keep shut".

She gasped lightly and ran after me trying to chase me, i held my backpack tight and ran past her heading to the kitchen.

"So whats for breakfast?".

I look at her. "Why do you always ask me that? Didn't you eat at home?".

"Ugh, Granny is the one cooking again".

"I love your grandma's food". I open the refrigerator taking out a jug of milk. "Even her pudding".

"Don't get me wrong, i do love what granny do but i like eating my cookies with sugar".

I laugh a little as I dropped my backpack on the counter. "She forgot the sugar?".

"She forgot the sugar".

I placed the jug of milk on the counter and drop the box of oats along with it too.

I pour the oats in the bowl along with the milk, She quickly grabbed the bowl not giving me a chance to dip my spoon in it.

"You gotta stop doing that". I tell her.

"Think of it this way". She nibbled on the oats. "I'm giving you time to go dress up".

"I am dressed up".

"Not like that, you are".

"Whats wrong with what I'm wearing?". I ask her looking at myself.

She shakes her head. "Oh my sweet bestie, Bailey, Bailey".

"Stop doing that".

"Girl, you ain't dressed like that". She lets out a scoff. "Now I see why you get bullied all the time".

I huffed angrily pushing up the rims of my glasses. "I do not get bullied, at least not anymore, but still".

"How can you wear sweat shirts and sweat pants on your first day of school?". She looks at me. "And damn, its the first day of Senior year".

I shrug unaffected. "So?".

"How you the fuck you gonna attract those hotties?". She stands up. "Come with me, there's no way I'm letting you get bullied again".

"Katie, no". I whined like a child. "I'm fine with this outfit I'm wearing".

"Wear the clothes I choose for you and I'll get you a box of those chocolates you always stare at whenever we walk past that door by the street shop".

"Promise?".

"Only if you wear the clothes I set out for you".

"Umm .. ". I rub my chin pretending to think for a moment. "Fine, its a Deal".

She squealed excitedly. "Make over time".

"No!!". I protested. "Only just the clothes, no makeup, got it?".

She rolled her eyes. "Whatever, lets get you changed, bestie".

I grabbed my backpack and slanged it over my shoulder walking towards the kitchen entrance but stopped realizing Katie isn't with me.

I turn back to see her munching on the oats. "Really?".

"I gotta eat, girl". She replied with her mouth full, dripping with milk.

"Just be quick with it, would ya?".

"Someone is eager for a change over". She teases me.

"News flash, I'm eager for the first day of school".

"Bailey". She gets up and drops the empty bowl in the kitchen sink. "Can you be less you for once?".

"Whats wrong with me loving school?".

"You are a nerd, i get that but try to make it less obvious. It will help you, trust me".

I held my heart dramatically. "Ouch, Katie that hurts".

"Lizzo said it alright, truth hurts". She takes her backpack wearing it. "Come on, lets go get you all changed up".

I shake my head at her as she leads me out of the kitchen. We walk past the living room heading to my own room.

"So is Owen home?". She asks as we walk past his room.

"No. He's not. Still at college". I lied. I don't really want talks of my brother, especially from Katie.

"Damn, i wanted to see his fine face".

Oh brother!! Now I have to listen.

I open my room door and we walk in with Katie still talking about my brother.

"Katie, can you please stop talking about my brother that way?". I ask her plopping on my bed.

"I can't help it, he got a__".

I cut her off. "Don't say it".

"Fine piece of ass". She completed her sentence.

"And you said it".

She smiles. "Bailey, try not to be jealous of Owen for once".

"I'm not jealous".

"Hmm". She hummed looking through my closet.

"For real, I'm not".

"If you are not then try to be like him". She urges me.

"I don't wanna be like him, Owen can never be my role model. Do you know how many girls he brings in each weekend?".

"I'm pretty sure their pussy must be having a fine time".

I gasp. "Katie".

"What? Is not like you haven't heard that word before".

"Well .. I don't like hearing unholy words".

"Cut some slacks, Bailey, would ya? This is the last year of senior high and sometimes, i still can't believe you are a virgin and not just that, you haven't kissed anyone".

"La, la, la". I cover my ears with my palms trying to block out her words.

"You never listen to me anyways".

"Exactly, so why try?". I shot back.

"Just shut the fuck up and try this out".

She drops clothes that I never knew I had until now on my laps. Black skater skirt and a red cropped tee.

"How is this any better?".

"It gives you the advantage of not getting bullied, stupid. Now take those glasses off and get changed".

She attempts to take my glasses off but I slap her hands away.

"Ouch, what was that for?".

"I can't see without my glasses". I remind her.

"Oh right I forgot". She muttered. "But that doesn't mean you always have to wear this big frame glasses, i can get you contacts".

"I'm just gonna go get changed". I tell her changing the subject as I stand up taking the clothes along me walking to the bathroom.

I removed my glasses and pinched the bridge of my nose rubbing it slightly.

I try to look around but everywhere is just blurry, nothing in sight seems clear to me.

This is why I usually keep my glasses on all the time, i really don't wanna get hurt as I can't see clearly without them.

Minutes later, i came out of the bathroom and Katie looked up at that instant.

"How do I look?". I say twirling around on my feet.

She gaped. "Oh bestie, you look good to eat".

I dropped the clothes I had worn earlier in the laundry basket.

"Try this out".

I take the black chiffon boots she gives me and I put them on.

"You see what happen when you listen to me". She drags me to face the mirror. "You look good, bestie".

I had give Katie one point for that, i looked good like she said, really good if I have to admit.

"And now for the hair".

"No!!". I protested. "My hair remains in a ponytail".

"I tried my best".

"Now lets get to school". I say grabbing my backpack on the bed as She too wears her own backpack and we set out the room.

She paused. "Do you smell that?".

"If its the smell of being late to school, then the heck yes".

"Not that, Bailey, it seems like__".

"Hey sis". Owen comes into the living room interrupting Katie, not that she even cares about that anyway.

"Hi Owen". Katie literally purrs drooling in front of him.

I tugged on Katie's arm. "Bye Owen".

"Hey". He stops me. "Don't you want a ride to school?".

"We sure do". Katie replies tucking her hair behind her ear acting all flirtatious.

"We'll take the bus". I drag Katie along with me to the door.

"Bye Owen, see__".

I push her through the open door not allowing her to finish her sentence as I walk out then closed the door behind me.

Seven Marshall

I roll sideways on the bed groaning having the hangover of yesterday. I sat up on the bed and noticed she wasn't there.

Fuck!! Where the hell is she now? I glanced at the hidden camera on the other side, its still active but I'll have to edit some parts.

"Hey baby".

I turn to see Trina come out of the shower room in just a short towel exposing all her curves.

"You still here? How delightful". I gave her a faux smile.

She walked towards me seductively. "You really were bent on destroying me last night".

I chuckled lightly knowing she was talking about the sex we had last night. And the fun part is, i got the whole thing on camera.

"You want more of that?".

She drops the towel to the floor. "I sure do want your beast".

Oh, this is getting good. Little does she knows, this is going to go viral on camera, she being naked right now only adds to it better.

"Maybe we have more time before school starts".

She walked towards me and kissed me, I had to reciprocate as part of the bet. She sat on my leg making her big butt touch my torso.

Fuck!! She's such, damn!! This is definitely going viral.

She started butt whining on my laps as she kissed me hungrily moving her butt to and fro riding me.

I stood up with her legs wrapped tightly around my waist and made her fall on the bed with me on top.

I brushed my hand on her thighs and place my head on her chest giving her nipple tiny bites.

I lifted my other hand to the other b**b and fondled with it while sucking from the other.

She gasp in ecstasy moaning as she wrap her hands around my shoulders.

"Seven!!". She moaned my name sending her fingers into my hair. "Don't stop".

Time for the big bomb, I disentangled from her hold and she looked at me quietly.

"And done". I say taking the hidden camera from where it was placed. "This was damn so easier than I thought".

"Seven .. ?".

"Make use of the door, Trina".