Requested by: kileenhood

Imagine: Dean flirting with a girl even though you and him are dating.

You and Dean have been happily dating for the past three months. You have known each other for several years, but have only  been hunting with the Winchesters for a couple of years. It took a long time for the eldest Winchester to finally admit his feelings towards you, but eventually he did, and he did it in most perfect way.

Every time you thought about the moment Dean had confessed his love for you, a smile appears on your face. You had loved Dean since the first moment you had seen him, but after hearing rumors about him, you couldn't give him the satisfaction of knowing that he had made yet another girl fall for him. 

So you played hard to get. Really hard to get. And one day Dean just couldn't take it anymore. He didn't care if you would never love him, he had to tell you that he loved you. So, he took you to a bar you knew all too well. It was the bar you were working at when you first met Dean. 

He led you to the table where he and Sam were sitting at when you waited on him. "Dean, what is this?" you remembered asking him. He just gave you a cheeky smile in response as he walked over to the jukebox that was there and played Keep on Loving You by REO Speedwagon, the song that you had chosen to play and dance to when you were cleaning up the bar, knowing Dean would be watching you.

Lastly, Dean grabbed two beers from the bar and then returned to your table handing you one of the beers.  You gave him a quizzical look and he took in a shaky breath. "Four years ago this was the bar I met you at. You were just a hot waitress but I knew there was so much more to you than that. I asked you for two beers, one for me, one for Sam. Those were the first I ever spoke to you. Later in the night, you played this song and danced to it. That was the moment I realized you weren't just hot, you were gorgeous, the most gorgeous thing I had ever seen. In that moment I fell in love with you, and soon Sam and I found out you were a hunter. That's when I knew you were my soulmate. Every moment I have spent with you since then has wrecked me. I am nervous for no reason, I go crazy every time you flirt with another guy, and I can't focus on hunts because I'm too concerned with making sure that you're okay. Four years ago, Y/N, I fell in love with you, and I never fell out of it," Dean told you, his eyes never leaving yours. 

A smile slowly started to form on your face as you told Dean, "It took you long enough. I love you too." Dean's reaction to those simple words was priceless, and you can never forget the smile on his face as he leaned over the table, same as you, and kissed you passionately.

You think about that night every day, wondering how you ended up with such an amazing man as Dean, and you couldn't be any happier than you were right now.

"Hey baby," Dean said entering your shared room where you were sitting on the bed reading a book. "Hey you," you replied with a smile, placing the book on the nightstand as Dean sat next to you. "I want to take you out," Dean told you, smiling. "Okay, where?" you asked. 

"It's a surprise," he responded with a smirk. You chuckled as you leaned forward and kissed him. "Fine, just let me get changed," you said. But he shook his head no, replying, "You look perfect right now."

"Dean, I'm in a T-shirt and sweats. I'm not even wearing any makeup," you protested. "Exactly, pure Y/N, just the way I like it," Dean replied, giving you another kiss, and then grabbing your hand and pulling you off the bed. 

You quickly slipped on your shoes and then followed your boyfriend out the door to the 1967 black Impala you had fallen in love with as much as Dean had. He opened the door for you, and you got in, before he shut it again.

He got into the driver's seat and turned on the ignition. The engine purred to life and Dean took off. You had been driving for a while and you were in the a secluded countryside. The suspension was killing you, so you decided to entertain yourself.

You scooted closer to Dean and kissed his cheek, before trailing the kisses down his jawline to his neck. "Y/N," he unintentionally moaned out. You smirked and looked him in the eyes. "What are you doing?" he asked with a smile.

You gave him your most innocent look as you replied, "Well, the way I see it, you are keeping me in suspension for way too long, Winchester, so what better way to pay you back than teasing you a little bit?" Dean gave you a fake glare as you continued your assault of kisses, making him roll his head to the side a little bit so you had more access to his neck.

After a couple of minutes, you decided to advance it a little and placed your hand on the side of the waistband of his pants. Slowly, you slid it towards the front of him, your lips never leaving his neck. After another moment, he turned to look at you and pulled you into a passionate kiss. The kiss only got more heated, but then it all went downhill.

As Dean paid more attention to you and less to the road, he swerved off of it. He quickly noticed and looked back at the road, and out of nowhere, a girl appeared. Dean quickly jerked the car out of the way. Luckily, he didn't run her over, but he did graze her with the car. 

Dean stopped the car, and you both looked at each other before quickly getting out and running over to the girl. She was unconscious and because she was only wearing a crop top and shorts, she had scrapes all over her arms and legs. "Come on, let's take her back to the Bunker," Dean said, picking her up and placing her in the back of the car.

You got in the back with her, and held her head in your lap, as Dean started driving again. You checked her pupils to make sure she didn't have a concussion and then started to tend to her wounds with the first aid kit you always kept in the car.

You all soon arrived at the Bunker, and Dean carried the girl out of the car and into the Bunker. He gently laid her on the couch, and you hand Dean the first aid kit as you left the room to get some wet washcloths to wash the blood off of her. 

When you came back, the girl was starting to wake up, and you were gentle as you explained what had happened. She was scared and confused at first, but soon she was at ease. Dean started washing the blood off of her as you went into the kitchen to make dinner. 

You were almost done and went to go tell Dean that it was ready when you heard him talking to the woman, and couldn't help but eavesdrop a little. "So, is that other girl your girlfriend?" the woman asked. Dean gave her a polite smile before replying, "Yep, we've been dating for a couple of months." 

"That's a shame," she replied with a smirk to which Dean raised an eyebrow. "Oh really, and why is that?" Dean asked, flashing her a smirk of her own. "Well, it would have been nice to show my savior some appreciation," she responded, giving a lustful look. Dean didn't respond for a moment, but then he said, "Well, if it was under any other circumstances I would definitely take you up on your offer, I would have killed to spend a night with a woman as beautiful as you."

You felt your heart crack but continued to listen. "Well in that case, why don't I get your number and we can meet up sometime and spend that night together. Your girlfriend would never have to know," she coaxed. But, Dean shook his head no. "I'm sorry, I can't do that to her," he replied.

"Well then how about sometime in the future? I mean do you honestly see yourself with her a year from now?" she questioned, a hopeful glint in her eyes. Dean waited for a moment before replying, "No." 

That was when your heart shattered and you couldn't take hearing anymore. You snuck away to yours and Dean's bedroom and shut the door. Sliding down it, you let the tears fall freely, and after a couple of minutes, you collected yourself and grabbed the duffel bag out from underneath your bed. 

You began packing all of your things into it, losing track of time. Soon, there was a knock on your door, before Dean opened it. "Hey, I dropped the girl off at the gas station, she called someone to pick her up," you nodded your head in response but you didn't look up at him.

"Dinner started burning so I took it off the burner," Dean said, attempting to get you to talk to him again, but you didn't say anything. That's when he noticed that you were packing your things into the bag. He took a step inside of the room and asked, "What are you doing?"

You zipped up the bag as you looked at him. "I'm leaving," you told him. "What? Why?" he asked, his voice slightly cracking as he felt his heart breaking inside. "Why does is matter Dean? You don't see me in your future anyway, right? Besides, I'm sure you'll find another girl to sleep with in a matter of days," you replied, slinging the bag over your shoulder.

Your words stung Dean, but you were hurt. You began making your way to the door, but Dean blocked you from leaving. "Dean," you started, but he cut you off. "You heard us talking," he muttered. "Yeah I did," you replied, before attempting to leave again, but with no success. 

"You didn't hear what I finished telling her did you?" Dean asked and you shook your head no. "I didn't think it was necessary to continue to let you shatter my heart with every word you spoke," you snapped back. 

"She asked me if I saw you in my future a year from now, and I said no," he reiterated. "Yeah, Dean, I know, I was there," you answered. 

"I said no because I don't look into the future. Every time I do, something bad happens. In this life, you can't have plans. I could spend days planning our future, planning what our wedding would look like, planning the names of ours kids, but it wouldn't change the fact, that a demon could come out of nowhere and end that in split seconds. I don't know what will happen in the future, but I do know that I want to love you forever," Dean explained. 

All you wanted to do was feel Dean's lips on yours in that moment, but something was holding you back. "Dean it doesn't change the fact that you were flirting with her," you said, refusing to make eye contact with him.

He let out a sigh before nodding his head. "I don't know what I was doing. Hell, I don't know what I am doing. I have never been this in love, and I'm so afraid I will screw it up. That flirting didn't mean anything to me. I used to flirt with every woman I saw. But, I swear Y/N, I never even thought about touching her in any way," he replied. 

You breathed a sigh of relief as your eyes finally met his. "Promise?" you asked. He gave you a loving smile before replying, "Promise." He then leaned down and gently placed his lips on yours. You wrapped your hands behind his neck and pulled him closer, deepening the kiss. 

When you both pulled away, Dean said, "I love you Y/N Y/L/N." You smiled at him as you replied, "I love you too, Dean Winchester," before connecting your lips to his once more. 

Hello my little monsters,

How did you guys like this one? Hopefully it was okay :) Thank you all for reading! I love you all and all of you are amazing!

Always Keep Fighting!

~Caela~