Boss 》WinWin

One

It was late October of 2018 in Chicago, Illinois, the weather was cold as the sun hung low in the clouds while the night began to fall upon the big city that was bustling with cars and busses...and gun shots.

That's all Courtney would hear everynight from her second story window of her home within her little suburban neighborhood on the outskirts of Chicago. It was always loud, the city was always alive in some way to the point that it would almost be terrifying to hear complete silence.

Courtney's POV:

I looked out my window at the dim street lights that lined up the sidewalks as the night air came in through my windows, blowing my hair back slightly as I became lost into my own thoughts. I wish I could be like all the other people I see around town, the had someone they loved with them, I had always wanted a boyfriend but my dad was so strict that he wouldn't let me date. He barely even let me leave the house especially with him unless he had his boys to protect us. He wanted to keep me away from his business which means no one could know about me besides his main guys.

"Daydreaming about boys again?" I heard my best friend, my only friend Samantha's voice come from behind me. I jumped and turned to face her, seeing her now sitting on my bed. "How did you get in here?" I asked as I looked at her surprised. "I snuck into the kitchen window" she said as she laughed. I shook my head as I realized she had asked me a question. "Daydreaming about boys? Pftttt" I lied as I turned away from her. "Okay..I was going to see if you wanted to go out and maybe find you a boy to talk to." She said, making me snap my head in her direction.

"Wait, so you don't have to rush off to somewhere in the middle of the night for no reason?" I asked, knowing that she always seemed to run off somewhere randomly especially when my dad came home. I decided not to question the reason she always ran off because it seemed pretty serious so I kept my mouth shut. "No, I want to get you out of this house today and besides, I got the day off." She said before smiling her mischievous smile.

"Wait, you mean we're gonna sneak out? My dad's home, what if he comes to check on me." I asked, worried about getting caught but I definitely did want to get out of this house. "We can set up something to make it look like you are asleep if he comes by." She reassured me as she stood up. "Okay I guess" I said, still doubtful of the whole thing. "But..you're gonna have to change into something a bit nicer." She said pointing out my pajamas as she walked over to the window while I got up. "I'll wait outside while you change." She said as she dropped out of the window to the ground, not even bothering to use the lattice to climb down.

I went to my closet and found a cute outfit, a grey loose fit shirt and black skinny jeans with the rips in the knees and a leather jacket with some black combat boots. I wanted to blend in and not be noticed if any of my dad's guys were out. I brushed my black hair and pushed my bangs out of my eyes before adjusting my glasses. I made sure I looked good before propping something up on my bed to make it look like O was sleeping. I checked myself one more time, I was worried about looking bad since I barely went out anywhere.

I sighed and walked over to my window, crawling down onto the lattice and to the ground quietly so my dad wouldn't hear. "Don't even ask me where we're going, it's a surprise." She said, cutting me off before I could even say anything. But I actually was going to ask that same question. I followed behind her as we walked down the sidewalk quickly, trying to get away from my house.

We eventually made it to town as I decided not to speak up, knowing she wouldn't answer any of my questions. We walked onto the streets as a few people seemed to stare at us for some reason but mostly Samantha like they knew her or something. But as soon as they saw me looking at them, they quickly turned their heads, further raising my suspicions. Before I knew it Samantha finally spoke up for the first time the entire walk here.

"And there it is" she said, making me look across the street to where she was pointing to see a bar with loud music playing and scary looking bikers and people that were similar to the people who had been staring at us a few minutes ago. "Uh, Samantha, you know I don't drink.." I said, wondering why in the world she would take me to a bar of all places, especially since neither of us were twenty one. "I come here all the time, it's fun, a good chance to actually talk to people." She said, pointing out that I was always kind of antisocial.

"How can we even get in?" I asked. Without a word, she pulled something out of her pocket and handed it to me. I took it and looked at it to see that it was a fake idea. "Where did you-" I started to ask before she cut me off. "Don't ask now come on!" She said, pulling my arm and taking me across the street to wait in line. We waited for only a few minutes before the bouncer looked at us as we scooted up to the front of the line. He looked suspicious as if he knew we were too young but as soon as he really looked at Samantha, his face lit up. "Hey! Sam!!!" He said excitedly as gestured for her to go through but started to hesitate with me.

"She's with me big guy" she said, making him smile and let me go through with her. "Anything for our number one customer." He said as we walked away. I laughed before speaking up. "Number one customer huh?" I joked. "Shut up" she said as she kept walking, making me follow her to the bar while she got a drink. "Go get a seat somewhere, I will be over there in a minute." She said before she started talking to this tall asian boy with brown hair.

I sighed and looked around, seeing an empty booth in the far corner so I walked over to it quickly to make sure no one would take it. I sat down and got on my phone, attempting to look busy but failing as I realized I had already seen just about everything on instagram so I sat my phone down on the table and sighed, running my hand through my hair. But suddenly, I felt like someone was staring at me and I fought with myself, trying to decide what to do. Should I look over? Should I stay looking at nothing and be awkward?

After a bit of thinking, I decided to look over quickly as the feeling increased. I mean one little look couldn't hurt right? I breathed in slowly before turning to see the hottest boy I had ever seen in my life looking at me from across the bar. He was asian but had dyed blonde hair with his bangs parted to the side and his eyes were piercing but so beautiful. All of his features were like that of a prince in a fairy tail, despite his mostly black clothes and his ear piercings. I felt my face, realizing that it was on fire as I must have been blushing really hard. He laughed slightly before going back to talking to his friends. Shit, the hot guy caught me looking at him..damn it Courtney, this is why you aren't allowed to go places...

Hey guys, thanks for reading! Hope you enjoyed this chapter. Sorry if it is kinda boring, I promise it will get into it the more you read on once I get more chapters published.

~-winney-