Dean Winchester Imagines

Womanizer

This one was requested by mariposa101194! Thank you for the request. I hope you enjoy!

*Y/n's POV*

Today was my first day at Sandover Bridge & Iron Inc. I was the new secretary. It has always been a dream to work there, it was the wealthiest business in all of Ohio. Ever since my dad worked there years ago, it was just a dream come true and I can't believe they hired me!

I took a long look in the mirror to make sure everything was in check. Once I was satisfied with all, I smoothed my dress, slipped my cardigan on, grabbed my essentials, and headed out the door. On the road, I put on an old CD my friend and I  used to listen to in high school. It seemed to calm my nerves when I listen to it.

******
I pulled into the parking garage and rolled up to the security booth. "Identification please." The scruffy, white bearded man said. I handed him my license. He looked at me. " I meant your identification card for entrance." "Oh, I'm sorry sir. I haven't received one yet. This is my first day here. I'm the new secretary for the boss, Dean Smith." He scoffed and chuckled a little bit. " Well isn't that surprise. This is his 15th secretary in 10 years. The man has some serious anger issues or just a perv, I have no idea. But he sounds like a handful. I wish you all the luck ma'am." I shyly smiled and thanked him.

I finally found a parking spot and sat there for a minute. "You're going to do fine, y/n. Nothing is going to stop you from working at the place, you've always wanted to work since you were a little girl." I whispered to myself. After 5 minutes of calming myself down, I switched the ignition off and stepped out of the car, onto the hard concrete. I looked around the crowded, but empty garage and searched for an elevator or stairs. To the left of me, a couple feet down, I found an elevator. I sighed in relief and pressed the button and entered, hitting the lobby floor.

A few seconds of music and a little jolting, the doors swung open, revealing a massive chandelier on the ceiling, two grand, curved stair cases leading up to another floor. My jaw gaped open in awe. I shook away the thoughts and walked slowly to the front desk. A lady, with long curly brown hair just like mine, and glasses was there typing away on her computer. I cleared my throat and she looked up at me and smiled. "Hi, sorry for bothering you. This is my first day and I'm the new secretary for Dean Smith and I'm not for sure where to find his office..." I told her. She simply smiled and nodded. "Okay, well you take these stairs up to the second floor and there are two sets of elevators, take whichever one and then he's on the top floor. I hope you're not afraid of heights!" We both chuckled. She pulled her hand out for me to shake it. "My name is Cindy, and if you have any more questions feel free to ask, even if you are on the top floor far away!" I nodded "thank you so much, and my name is y/n by the way." "Nice to meet you, y/n."

I made my way up the curved stairs, hearing my heart beating louder and faster with each step I took. At the top of the stairs, I stop and look around. The walls were a dark brown with artwork complementing them. I arrived at the elevators and stepped in. The doors were about to close when a tall longish brown haired man in a yellow shirt and khakis pants stopped them and rushed inside. He was about to press a floor number, but he pulled back, realizing that I was going the same place he was. I took a small step away, trying to keep distance and kept my head down to avoid conversation. Even though my head was down, I could feel his eyes burning through me, so I looked up and he was smiling. He stuck his hand out, gesturing me to shake it. "Hi, my name is Sam, Sam Wesson." I took his hand and returned it. "Y/N Y/L/N." He nodded, still smiling. "I'm guessing you're new here?" "Is it that obvious?" I smiled shyly. He chuckled. "Just a tad, what is your position?" "I'm the new assistant for Dean Smith." With that, Sam's smile faded into a frown and the elevator doors slid open. "Well good luck, and if you EVER need anything, let me know," He said with a serious/scared tone. I slowly nodded and stepped out the elevator.

The room was surrounded with desks and employees dressed in yellow shorts and khakis with headsets attaches to their heads. Phones were ringing off the wall. I started to get a headache. I scanned the room, trying to find Sam. I saw him walking to his desk. "Sam!" I yelled. He turned around and looked at me. "I don't know where his office is?" I mouth to him. All he did was point the direction behind me and turned back around and sat down at his desk. I slowly turned myself around and came face to face with the one and only, Dean Smith. "Oh, hi!" I chuckled nervously. He nodded his head and smirked. Wow, he was hot. He pulled his hand out and I shook it. "You must be y/n." I nodded my head, feeling my face become warm. "Follow me."

I followed him into a gigantic office with an enormous window view. I stared in awe. "Wow, this is beautiful." He chuckled "Thank you, Y/n. That is very kind of you. Have a seat!"

A.N.

I'm going to end this part. And make a part 2. I hope everyone enjoyed it! Please feel free to leave comments and tell me how you feel about everything so far! I would greatly appreciate it!

-Aransas