“Insecurities” Dean x Reader
Dean x Reader
Summary: Dean and reader run into her ex at a party.
Warnings: Mention of cheating, swearing, implied smut
“Zip me up?” I say as I walk into Dean’s room. He looks at me, mouth slightly agape, and nods.
“You look beautiful.” He whispers slightly, taking a hold of my zipper and pulling it up. I smiled at him, blushing.
“You don’t look too bad yourself, Winchester.” I respond, admiring him in his suit. We were on a case tonight- one that required us to go undercover to a party. I wasn’t complaining; I never got to be dressed up, and this was my one excuse to feel like a girl.
I grew up with the Winchester boys. My mom passed away giving birth to me, and my dad Bobby took me in afterwards. He tried to give me the most normal life possible, sending me to regular high school and keeping me away from hunting. Unfortunately, I was a rebel, and anytime my “older brothers” Sam and Dean would come to visit, I’d make them teach me how to hunt. By the time my dad had died, I had just graduated high school and I had nowhere to go. Sam and Dean took me in. They figured that they had taught me enough about hunting in the past that I could join them on the road.
A few years have gone by, and all those years of secret training definitely payed off. I’m a great hunter, maybe even better than the boys. Not that I would ever tell them that.
“Dean, are you ready? We have to go now if we want to make it on time.” Sam came into his room. He slightly smirked when he saw I was in Dean’s room, but it disappeared once he saw that I noticed. Sam has been suspecting something going on between Dean and I since the moment I started living with them, despite it not being true. Dean is my best friend, that’s all. My hot as hell best friend, but that doesn’t change anything.
“Are you ready, (Y/N)?” Dean asks me.
“Let’s go.” I say, nodding. I grab my purse and we make our way out of the bunker. I feel eyes on me as I walk in front of them, and I smile a little bit, knowing that I looked good.
We get to the event fashionably late, and try to make ourselves fit in. Everyone here looked very rich, and they were all beautiful. I held my head a little higher, trying to fit in with the crowd.
“What exactly are we looking for again?” I ask Sam, grabbing a glass of champagne. I down it quickly.
“Cursed object. Necklace. It’s supposed to be upstairs in one of the bedrooms. We need to find a way to get up there.”
“I can go get it. Say I was looking for the bathroom.” I shrugged.
“You’re right. No one’s going to suspect a beautiful girl of anything.” Dean said. I couldn’t tell if he was being serious or not, but at the chance that he was, I felt butterflies in my stomach.
In case my plan of looking for the bathroom failed, I grabbed another glass of champagne to take with me, so I could just act like a drunk lost girl if needed. I walk up the stairs, making an effort to blend in with the crowd so no one thought anything of it.
I find the necklace with ease (It was the ugliest thing I have ever seen- I don’t know why anyone would wear such a thing), and tuck it into my purse. As I walk out of the room, I hear a girl giggling down the hallway. I turn my head and see a beautiful blonde girl stumbling out of another bedroom, with a man following behind her. I take a closer look, and see… Josh?
Josh was my boyfriend all throughout high school. My first love, and also my first heartbreak. He cheated on me. I haven’t seen him since I graduated, and that was ten years ago. Desperate to avoid an awkward “How have you been?” talk, I turn around and try to walk away.
“(Y/N)”? Josh exclaims.
Shit. I turn around slowly and try to look excited to see him.
“Wow, Josh, hi!” I say. He leans over for a hug, but I don’t hug him back. “So, who’s this?” I ask, not really caring but trying to be polite.
“This is…” He trails off. “What’s your name again, sweetie?” He asks the blonde chick. My mouth drops open. She looks very offended, and slaps him. He rubs his jaw as she stomps downstairs.
“Well, I guess it doesn’t matter now, does it?” He laughs.
As he keeps rambling on about shit I couldn’t care less about, I pull out my phone and text Dean.
SOS. Need you up here now.
I put my phone away and pretend like I just heard anything that he just told me. I hear someone running up the stairs and I pray that it’s Dean.
Prayer answered. Dean appears in sight, looking around for me, ready to pull out his gun.
“Dean, baby.” I walk up to him, kissing his cheek. He looks intensely confused, but goes along with it.
“Josh, I’d like you to meet my boyfriend, Dean.” I smile, wrapping my hand in his and standing as close as possible.
“Uh, hi.” Dean says, reaching to shake his hand. He looks down on me, a look of “what the fuck is going on”, but I don’t say anything.
“Say, (Y/N)… Isn’t he a little… Old for you?” Josh says, with a disgusted look on his face.
“Excuse me?” Dean scoffs, offended. “I’m only 38.”
“You’re a whole ten years younger than him. He rich or something?” Josh laughs, judgement echoing through his voice.
“No, I’m actually with him because he’s amazing in bed. Oh, man, that dick is-“ I start, but Dean cuts me off.
“Okay,” Dean says, letting out a breath that sounds like he’s been holding in for a long time. “(Y/N), let me talk to this guy for a moment.”
You listen to him, and walk to the other side of the hallway. You see Sam at the bottom of the stairs, and he gives you a look of confusion. I tell him to give you a minute. I try and hear what Dean is telling Josh, but I can only make out a few words. Judging by the look on Josh’s face- I don’t guess it’s good.
“We’re done here.” Dean growls, walking over to you. Josh stares at you guys, eyes wide and terrified. As if to prove a point, Dean grabs my ass as we walk away, making sure he sees it.
The car ride back to the bunker is silent. Sam tried to talk a few times, but Dean would him to shut up before he could even get a second word out.
Sam and Dean went straight to their individual rooms once we got there. Sam was annoyed at Dean for him being an asshole the whole way home, but I couldn’t figure out why Dean was still so pissed. I can talk to him about it in the morning.
I changed into my pajamas and laid down in bed, turning on the TV. Right as I got into my show, I hear a knock on my door.
“Come in,” I say. Dean walks in, wearing only pajama shorts and no shirt. I can’t help but admire how attractive his body is.
“Can we talk?”
“Sure.” I turn off the tv, giving him my full attention.
“Am I old?” He frowns, sitting on my bed. I look at him, in shock he would even ask that.
“Not at all. Look if this is about what Josh said, he’s just an asshole, don’t take it to heart.”
“It’s not just that. I’ve been thinking about it a lot lately. I can’t get away with saying I’m in my twenties anymore to chicks.” He laughs, running his fingers through his hair.
“You don’t need to lie about your age, Dean. You’re fuckable regardless. Look at you, you’re like-“ I stopped myself. I go quiet. I have no idea why I even just said that. Must be the champagne.
I avoid looking at him. I basically just told him I want to have sex with him.
“(Y/N), look at me.” He says softly. I look up at him, and he leans in. I can’t even begin to process what was happening until he was on top of me and we were making out.
“Fuck, (Y/N), you have no idea how long I have been wanting to do that.” Dean says, pausing.
“I never said I wanted you to stop.”.
Well, let’s just say, I was right- he is amazing in bed.