#cockyDean

[impala1967dwinchester]

Dean Winchester: Queen

*Credit to gif owner* 

Paring: Dean x reader 

Pov: Readers

Warnings: Dean dressing in drag, swearing, Dean, loss of a bet, Dean being cocky, mention of Sam, Jealous!Reader Angst/Fluff, lots of talks with Sam, lots of talking with Dean towards the end. reader self-doubt, Dean being reassuring. 

Summary: When Dean and the reader place a bet, it goes very much not in Dean favor. Dean has a tendency to get bored quickly though, which leads down a harsh road for the reader. Coming back to the bunker she tries to pretend everything is fine, but Dean wants answers. 

Word Count: 3k 

A/N- I know lots of pov switches I’m sorry... but I hope this is good and y’all like it. 

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Taglist: @akshi8278​ @deanswaywardgirl​ @hit-meup69​

“Bets are down!” Sam said.

Y/n had bet that if she won that game of pool that Dean would have to dress in drag. Dean bet that if he won pool which he was cocky about winning that Y/n would have to do the research for the next four hunts.  

What neither one of them knew was the bet the other one placed.  

Sam was the only one. So, the game began. I racked up the fifteen Dean grabbed his pool stick, and grabbed me a pool stick as well. He was being sort of gentleman. He chalked the end of both the pool sticks.  

“Are you ready to get your ass beat!?” Dean said handing me my pool stick. “I can’t wait for you to have to do my bet.” Dean said excitement dripping into his words.  

I rolled my eyes and rocked on the back of my heels. “Are you done being cocky Dean, so we can play this game?” I asked looking over at Sam.  

He just shrugged and watch Dean and I. “Come on Dean just play. Stop trying to be an asshole. I bet Y/n doesn’t really care how much you show off.” Sam said.  

Dean huffed and started to play. His board shoulders leaning over the pool table, lining the pool stick up with the white cue ball. I lifted the rack and stepped away from the pool table.  

He struck the cue ball and game began. None of the colored balls or striped balls ended up ports at the corners of the pool table. Dean stepped back and let me have a go, figuring out what ball I wanted to take a hit at I lined my pool stick up with the white cue ball and strikes it.  

The cue ball ended up hitting at least four balls two of which were colored balls landing into the corner spots. Sam sat and watched as Dean looked over at me and huffed once again in a sort of defeat. “Don’t get your panties in a twist, Ya hear Dean.” Sam said.  

Dean only shooed him off with a wave of his hand, and continued to play. This cycle went on for a bit. I’d play and get at least one ball in every time. I’d back up and let Dean take over the pool table, I’d go sit with Sam drink whatever beer I had left. And wait.

Wait for the grunt of disappoint when Dean didn’t any of his striped balls into the pockets, or a “Hell Yeah!” from Dean when he got a ball pocketed. Dean’s macho stance whenever he did hit a ball was ridiculous. “You know you honestly make him work for things.” Sam said commenting on how much Dean was really putting effort into the game.

“Come on now Sam. That’ I say waving my hand over the figure of Dean farther away ‘That right there is all Dean. I have nothing to do with any of that.” I said not really wanting to believe that I may have that great of effect on Dean like Sam says.

Dean is great at pool. Dean doesn’t lose bets either. Sam has watched his entire life Dean play pool and win every game. So maybe Sam sees something that I can’t see, or something neither Dean or I can see. Yeah, maybe Sam's right, maybe I have just the great of an effect on Dean Winchester.  

We continued to play, each other us going back and forth from the pool table. Finally, the last-colored ball was sitting on the pool table, black eight ball was staring at me from across the table. taunting me to win the game, I lined my stick up with the cue ball and went through with a solid hit. It hit and within seconds the eight ball was in the pocket and I had won the game.

Meaning that Dean, oh poor Dean had lost the bet. Not a normal thing either for him to lose, but I keep thinking about what Sam said. I really hope that Sam was right for my own sake.  

Sam looked over at me grinning at me. Dean was too preoccupied with a rather younger woman sitting not too far from the bar. He said before he left that he was getting more drinks and that there was no way I was going to be able to hit that last ball in.  

All the happiness and excitement went out the window when I saw Dean flirting with her at the bar. His swagger and smirking face turned on to the max. It would have anyone weak to the knees.  

Sam's eyes followed mine. Even Sam didn’t know that I wanted to be with Dean. Nobody knows, and I’d like to think I don’t want anyone to know. Because if I’m the only person then I don’t have to listen to Sam try and force to tell him, or Dean push me away.... I don’t want any of that.  

Sam's eyes landed on his brother flirting his way into the woman’s pants. He looked over at me. I played a good game of pool, but I didn’t have a good poker face.  

Sam got up from his bar stool at the table. He stood next to me and bumped my shoulder with his own, biting the inside of cheek I took a deep breath in and looked over at Sam. “Dean tends to be blind to the good things in front of him.” Sam said.  

“It doesn’t matter. The happy moment is gone. He’s bored. So, I take the rest of my pride and leave with it. Because I’m sorry Sam, but Dean isn’t worth the heartbreak.” I said putting the pool stick down on the table and grabbing my jacket from the bar stool seat that I was sitting at.  

Sam shrugged his shoulders and apologized for Dean. “I’m sorry for him. Drive back to the bunker, and I’ll get him home without extra company.” He said, before kissing my temple.  

I smiled for a quick second at Sam before walking past Dean at the bar with the women straight out the door and to my car. I slammed my car door and rested my head against the steering wheel. Letting my body finally go through the emotions. Crying until my steering wheel was soaked.

Dean Pov:  

When I finally looked back over at the pool table the first thing, I noticed was no Y/n. Where’d she go? I got up from the bar and walked back with the drink that I had ordered.  

“Sam, where’s Y/n?” I asked, noticing the pool stick sitting on the table. Sam didn’t turn around at all, his eye very much focused on the sports game on the TV screen above. Setting the drinks on the table I asked again.  

“Sam, where’s Y/N?” He turned and just shook his head. “Dude seriously, her jacket isn’t here and her pool stick is sitting on the table.” I said still very confused as to what was truly going on.  

“Dude she left.” Sam said jugging the rest of his beer. “But we weren’t even done with the pool game.” I said a little huff falling out with my words. “Yeah, you were, Dean. Don’t play innocent like you weren’t feeling that girl up at the bar.... Oh, and by the way she won.” Sam said shortly.  

I walked over to the pool table noticing all the colored balls were gone pocketed in the corners of the pool table. ‘Damn that girl beat me’ I thought. Wait I don’t understand why’d she leave just like that. I didn’t say anything to her.  

“Oh my god Dean, I can hear you thinking. Let me guess you can’t figure out what you did wrong can you?” Sam said getting up and tucking his bar stool under the table. “Let’s go. I’m ready to go home.” Sam said. I really didn’t have any choice, so I chugging the rest of my beer, and throw some cash on the table before jogging to catch up to Sam.  

Y/n Pov  

I sat in the kitchen with a glass of whiskey. Sipping it ever so often, but hearing the bunker door open and then shut I decided to just chug the whiskey. It burnt at tad as it fell past my lips and down my throat.  

In walked Sam and then shortly Dean walked in. Sam was silent grabbing a water bottle from the fridge and giving me a kiss on the cheek before walking out of the kitchen.  

Again, it was silent. “So... Sam gave me your bet. I’ll do it. I just have a question’ Dean asked, I turned in the seat and faced him. Dean was leaning up against the kitchen island arms crossed his chest and his ankles crossed. ‘Why’d you leave the bar early.” He said finishing his sentence.  

Bewildered by how Dean thought he had done nothing wrong I sighed heavily and went to say something it couldn’t. The words not wanting to fall out of my mouth. If they fell out then that would mean that they were real.  

“If I dress you in that drag... I tell you afterwards. Deal?” I asked. Hoping Dean would let it go for tonight. I could have the last fun with Dean tomorrow and then I’ll tell him. “Okay fine. Tomorrow after you’re done.” He said pushing off the kitchen island and kissing me on my temple.  

Leaving me alone once again in the vast space of the kitchen.  

I won’t say that I didn’t have fun grabbing all the shit I needed for dressing Dean up in drag. Grabbing laced up combat heels, a black dress, and a shit ton of makeup. I wanted this to be fun. And how can I forget I grabbed a bleach blonde long wig to complete whatever look I was going for.  

Shooting Dean, a message to come to library he was there quicker than you could say apple pie. It was awkward at first since everything that had happened last night, but he had gotten over that pretty quickly. Dean sat down in front of me.

“Are you ready?” I questioned him. “I lost a bet. I really can’t pull myself outta this one can I.” He spoke. “So, I’m going to take that as yes.” I spoke. After almost three hours of me trying to do Deans drag makeup. Constantly having to tell him to close his eyes, or whatever other instruction I gave him. I was done with that part.  

He got up, “My face all the sudden feels every heavy.” He said gently patting his cheeks with his palm. “Don’t touch!” I said swatting his hand away. Dean raised his hands in defense.  

“Here!" I said shoving the bag with everything except the wig to him. Go change, just don’t look at the make-up, yeah.” I spoke. sitting back down in the chair with a plop.  

Dean getting dressed took another hour. He walked out the dress wasn’t tight around his figure and the lace stockings I had also bought he was wearing; the boots look good. He was little wobbly but otherwise he looked alright.  

He walked over to me. Reminding me just how much taller he was then me now that he had a pair of heels on. “Put your head down.” I said quietly but he followed my instructions. When Dean flipped his head back over, he had a wig on. The extra weight throwing his head off for a long second.  

As Dean tried to regain his head balance, I shot Sam a message asking him to come out the library and to have his camera ready. In a split-second Sam was there with his phone.

Dean stood-up his hands on his hips. “Yeah, laugh it up. I’m just going to say that I look like a bad ass bitch.” He said trying to balance on the heel on the combat boots I had grabbed.  

“Can we take pictures? We promise we won't share them.” I asked, getting for a harsh ‘no’, but instead the answer was yes. Sam took a few and so did I. then Sam waved to us saying he had reading he had to catch up on.  

“So... Now that I've done this, can you tell me why you left the bar early yesterday night.” Dean said reaching up to take off the wig. “Yeah, but first get out of the clothes because I bet, you’re uncomfortable and you come back here, and I’ll take all this shit off your face, agreed.” I spoke.  

He gave me a sideways glance, “Okay, don’t go running off okay.” He said as he got up wobbling and holding onto objects as he walked away. Only a few minutes he came back wearing only a pair of sweats and a pair of Christmas slippers I had gotten both of the boys.  

“Please take this stuff off my face, because to be honest with you I can feel it seeping into my skin.” Dean said. I laughed a little thinking about how realistic that explanation was to what it really felt like.  

I got to work. Wiping Deans eye gently with the cotton pad. “Can you please tell me now?” Dean said eye closed. The feeling of his eye not being on me as these words passed my lips was actually more helpful.  

“U mm... you left... and everything was going great, but... You... and then” I said skipping over words and frustrating myself. Dean reached out placing his hand on my wrist. “Y/n just slow down. One step at a time.” He spoke.  

Taking a deep breath in, I started again. “So, everything was going well, you were being your cocky self which doesn’t bother me. And then all the sudden it seemed like you got bored of us... actually, more like you got bored of me and the game. Like whenever it just you and me. Some younger chick takes your attention.” I said, grabbing a new cotton pad and starting to clean Deans other eye.

You’ve got to get the rest of your thought-out Y/n.  

“Dean I would do anything for you. I hope you know that. Literally anything I’d die for you to be able to save the world. But I don't much in return. I ask for you spend some of your precious time with you. I just want your attention. I’ll do anything for you to just want me.” I spoke  

I gasped and covered my mouth. Oops that part wasn’t supposed to come out. I finished in eyes. He opened them and grabbed my wrist before I could grab another cotton pad.  

“Do you really mean everything you just said.” He asked, I kept my eyes the floor suddenly finding that much more interesting than Dean’s emerald green eyes. Or his amazing freckles. I felt a touch of Deans hand on my chin, forcing me to look at him.  

“Did you mean it Y/n?” Dean asked again a sterner tone falling into the words. “Yes, Dean.” I said a frown falling onto my features. So many thoughts running through my head but none of them were the next things that Dean said to me.  

“Glad, because I want you too.” He spoke. Thank god Dean finger was still under my chin because if not my jaw would have landed on the floor between our legs. “So, the flirting?” I asked in a hushed voice. Not trusting my own words at current moment.  

Dean face contorted and he took a moment to think. “Those girls... they were the only way I thought I could get over you, but I realize now that I’m a complete and utter asshole. A blind asshole. I’m sorry Y/n.” Dean said

His hand migrating to my cheek and his thumb rubbing right under my eye in a comforting way. I leaned into the touch. “You are an asshole. Just neither of us knew what the other was thinking.” I said touching out forehead together.  

“Can you get the rest of this makeup off, please, Y/n?” Dean asked. I rolled my eyes and pulled away from his forehead.” Way to ruin the moment Winchester.” I said before I started cleaning up the rest of Deans face.

‘Yeah, I know, but I really wanted to kiss you properly without any makeup on.” He said smashing his lips into mine, and holding down tight onto my waist and forearm. When he pulled away needing air he asked “We’re both idiots, but can we be idiots together?”  I smiled and shrugged my shoulder before lunging in for another Dean Winchester kiss.

“Wait, you don’t care that I don’t look like the other girls the you flirt with?” I asked shyness overcoming me. My grasp on the idea that Dean would even want me was eating away at my brain. Giving me a very perplexed look, and scrunching his eyebrows.  

“Look I know that it looks like I have a type.” Dean said grabbing into one of my thighs. “But, that’s a different Dean, that’s hopefully in the past. I know that I have a track record for only bring home blonde skinny women, but I... I want you and your body. I want all your thick parts’ he said squeezing my thigh. ‘I want your crazy bed head in the morning. I want you to continue trying to beat me at pool, I want you to be with me. I want so many things, but all of them are because of you.” Dean said pausing to let me take in his words. “I want whatever you want to give me. I don’t care what your body looks like because that’s not what made me attracted to you doll. Your heart, mind, and soul are what made me want you. I hope that’s okay” He said.  

I smiling and sniffed my nose trying to stop the cascade of tears that was about to break. “Yeah, that’s okay Dean.” I said grasping Deans strong body for a hug.  

Completed on: 04/11/2021