Chapter Text
You laughed hysterically and tried not to choke on your beer as Sam walked over to the male bar tender. It had been a rough couple of days for you and the Winchesters. You had just salted and burned a ghost that had been terrorizing an old theater and now the three of you were relaxing at a bar located a few minutes away from the bunker. You all agreed that the three of you needed some stress free time together, so picking up dates for the evening was not allowed. You were surprised that Dean had agreed to this rule so easily, but you weren’t going to question it. Instead, you relished the extra time you got to spend with the man who you secretly loved, and your best friend who was about to make a total fool of himself.
It was Sam’s idea to play truth or dare, something you knew he was about to regret. Dean had dared Sam to go up to the (hot) male bar tender, order a pink cosmopolitan, and then sing “My Milkshake Brings All The Boys to the Yard”. It was a good thing that the three of you were pretty buzzed, or else there was no way in hell this game would even happen.
“Twenty bucks says Sammy’s gonna wuss out,” Dean said, holding a hand out to you.
You flashed him your best smirk and said, “You’re on, Winchester. I have faith in my best friend. He won’t let me down.”
The two of you shook hands and went back to watching as the younger Winchester made his way to the bar.
That’s how it had been between you and Dean since he got back from hell a few years ago – normal. You two were still good friends, and if anything, your friendship had only gotten stronger. Neither of you had ever acknowledged the night you spent together right before Dean got dragged to hell. You thought about it from time to time, and still considered it to be one of the best experiences of your life. Not that Dean needed to know that. You figured that the intense connection he seemed to feel towards you that night was only because of his impending death. You still loved him with all your heart, but you ignored it for the sake of your sanity.
Unfortunately, Dean wasn’t making it easy for you to ignore your feelings for him. When he wasn’t chatting up a random girl or busy working on a case, he was paying close attention to you. Sometimes he got flirty, sometimes it seemed purely platonic, but you just brushed the mixed signals off as Dean being Dean. At that moment, he was sitting across from you, gazing at you in awe while you laughed at Sam. Though, you had no idea.
“He’s gonna do it! He’s gonna…oh shoot he may not do it. Wait, false alarm! Come on Sammy, don’t fail me now!” you exclaimed while bouncing in your seat.
Now it was Dean’s turn to laugh hysterically. Damn, you thought. If smiles could kill…
Since the bar was so noisy, Sam had to keep his phone on so you and Dean could listen to him though your own phone. The two of you leaned in to hear, and you were suddenly very much aware of how close Dean was to you. While he was pressed up against you, you couldn’t help the flashbacks of that rainy night that came flowing into your brain. You were zoned out for a few moments before Dean jerked away and doubled over with laughter. Apparently Sam had fulfilled his dare – and you missed it. Sam returned to your table shortly after, handing you the pink drink and downing three glasses of whiskey.
“We are never, ever, playing this game again,” he huffed.
Dean continued to laugh as he slid a twenty dollar bill your way.
“Nice to see you made a couple bucks off my embarrassment, Y/N!” Sam exclaimed.
“Well Sammy, someone’s gotta pay for the drinks!” you replied. “No worries though, I bet on you, not against you.”
“And I clearly underestimated my little brother!” Dean said, raising a shot of tequila to Sam before swallowing it in one gulp.
“Alright, alright,” continued Sam. “It’s my turn to embarrass someone. Y/N - truth or dare?”
You thought for a moment, and decided that there was no way you were going to allow Sam to get his revenge on you.
“Truth,” you decided, your voice ringing with confidence. You and the boys knew everything about each other, so there was no way that this could backfire. Or, so you thought.
“Hmmmm…” Sam thought out loud. “Okay, I got one. Tell us the story of your first time.”
“What?” you asked, eyes going wide.
“Your first time. No need for details. Be as vague as you want. Just tell us the when and where. And who, of course,” Sam said with a smirk.
Shit. Usually, you’d be okay with telling the boys anything. You’d gladly tell them about the last time you had sex: it was with a cop named Matt over in Connecticut when the three of you worked that vetala case a few months ago. Sure, you didn’t get as much romantic action as the guys did, but at least you remembered the names of the people you’d slept with. And you definitely remembered the name of the first man you’d slept with. You remembered every single detail of that night.
“Tick tock, Y/N,” Dean said, taking a swig of his beer.
You let out a long sigh before speaking. “Fine. It was a while ago,” you began, trying to be as vague as possible. “I was with this guy, and he was about to go away for a while. We were driving back from a restaurant when his car suddenly broke down.”
You glanced over at Dean just in time to see his head snap up, his eyes staring straight into yours. You turned back to Sam and continued.
“Then it started to pour outside; lightening, thunder, the whole shebang.”
Dean’s mouth was hanging open a little bit, and you noticed that he hadn’t touched his drink since you started telling the story.
“We got to talking about some deep stuff. And then one thing led to another and we ended up doing it right there and then. That’s it. The end. Who’s up for another round of tequila?” you finished at a rapid pace.
Sam’s eyebrows shot up, and you were sure he had figured it out. Thankfully, he was too drunk to put the pieces together.
“Car sex?!” the younger Winchester exclaimed a little too loudly. “That was your first time? Don’t get me wrong, Y/N, but I always thought you would have gone for a more romantic setting.”
“It wasn’t bad, actually,” you stated. “In fact, it may have been one of the best nights of my life.” At this point you were staring intently at your beer bottle, picking the label off, in order to avoid Dean’s eyes.
“Wow. It sounds like this guy left quite an impression on you, Y/N,” Dean said, trying too hard to sound casual.
Then, after a hiccup, Sam asked, “What happened to him after?”
You hesitated before deciding that you’d better just say it all at once and get it over with. “Like I said,” you continued, “he left. He came back a few months after that, and we’ve stayed friends since. But neither of us has ever mentioned that night. Sometimes I think it would be best to just forget the whole thing.”
At this point you had mustered enough courage to look Dean in the eye. His mouth was closed now, and the muscle in his jaw jumped.
“Well I think it sounds like you and this guy would be good together!” Sam announced a little too happily. “You should call him, Y/N. Or gimme your phone and I’ll call him for you!”
You hadn’t seen him this drunk in a long time. Dean seemed to had read your mind, and decided that it was time for the three of you to head home. Back at the bunker, you and Dean had the task of getting a very drunk Sam into bed. Once that was done, you made a beeline to your room as fast as you possibly could.
I fucked up, you thought to yourself. I told Dean, and now I’ve ruined our friendship. Tears began to blur your vision as you entered your room. You started to close your door when a hand stopped it. Dean.
“Can we talk?” he asked.
“Uh, yeah, sure. Come on in,” you said, shutting the door behind him and quickly wiping the tears from your eyes.
You waited for him to sit down but he didn’t. So you didn’t either. After 8 agonizing seconds of silence (yes, you counted), Dean spoke.
“Why didn’t you tell me?”
You hesitated for a bit longer. “I didn’t think it mattered, Dean. I didn’t even think you remembered it to be honest,” you said, muttering the last part.
Dean stared at you with a look of shock on his face. “Of course it mattered, Y/N! If I had known it was your first time, I would have done everything differently.”
“Yeah, well I wouldn’t change a second of it,” you snapped. “I’m sorry if you regret it, Dean. I truly am. But can we please, please, go back to how we were a few hours ago? Pretend it never happened?”
Dean shook his head in disbelief. “No we can’t Y/N. I can’t pretend anymore. And I sure as hell ain’t gonna let you believe that I regret that night. Because I don’t. It was the best night of my life, Y/N.”
Now it was your turn to stare at him in shock.
“When I was in hell,” Dean explained, “when I was being tortured and doing the torturing, there were a few memories that I was able to hang on to in order to get through it all. Some were of Sammy, some were of my parents, but the most vivid memory was always of you.”
Your jaw was practically on the floor at this point, not that either of you noticed. Dean grabbed your hands and sat you down on your bed. Then he kneeled on the floor in front of you so that he was looking up at you. You stayed silent, waiting for him to continue.
“When I said I would have done everything differently if I knew it was your first time, I meant that I would have made sure to make it perfect for you. I wouldn’t have been with you in a broken down car at the side of the road. I would have planned something special. I would have gone slower. I would have asked before touching you. Shit, I would have taken you out to a nice dinner first!”
“But I wanted you to touch me,” you insisted. “And it was perfect Dean. It was! That car, you know I love the impala almost as much as you do. And you were so gentle with me, almost as if I were made of glass. Plus, the pie we had right before really was the best pie I’ve ever had.” He smiled at that part, and you smiled too before continuing. “I always assumed you didn’t remember or you didn’t care because you never mentioned it in all these years.”
“You never mentioned it either, Y/N,” Dean pointed out. “I never said anything because I didn’t want you to feel uncomfortable. The truth is, that night is so important to me. You know you were the last woman I was with before I went to hell? But that’s not why it was so important. Y/N, besides Sam, you are the most important person in my life. You always have been. You’re brave and smart and kind and funny and so damn beautiful. You mean so much to me and I wouldn’t give up the night we spent together for anything in the world.”
You stared at him with wide eyes before saying “So I wasn’t just a one night stand to you?”
Dean let out a low chuckle before placing his palms on either side of your face.
“No, you weren’t. Don’t you get it yet, Y/N? I love you. I have for a long, long time. It’s okay if you don’t feel the same way. I’m not asking for anything. I just need you to know.”
You felt a tear slip down your face. You put your own hands on Dean’s face, mirroring his earlier actions, and kissed him deeply. He kissed you back, his hands tangling in your hair and his teeth grazing your bottom lip.
After the two of you had stopped to catch your breath, you rested your forehead against his and said “I love you too, Dean. So, so much.”
Dean smiled one of his most rare smiles; the kind that reached his eyes, crinkling the skin around them. You kissed the freckles that dusted his face as he ran a hand through your hair. Then he planted a kiss on your forehead, then your temple, then worked his lips along your jawline until he finally recaptured your lips with his own.
After a few more minutes of kissing, Dean pulled away and said “We gotta slow down a bit, okay? We have the rest of our lives for this, and as cheesy as it sounds, I wanna savor every second I spend with you.”
You bit your lip and nodded. Dean kissed you one more time before standing up, pulling you up with him.
“Dance with me, Y/N?” he asked.
“But there’s no music,” you replied, unable to hide your growing smile.
“Then we’ll make some,” Dean simply stated.
He took your hand in his, and then placed his other hand on your waist before the two of you started swaying to the silence. Then Dean began to sing.
Someone’s always coming around here trailing some new kill
You recognized the song instantly. Angeles. The song he sang to you that night. He smiled down at you while continuing the song. You shifted positions so that both of your arms were around his waist and both of his arms were securely around you. You laid you head against his chest, and you could feel that his heartbeat was racing as fast as yours was. When he got to your favorite part of the song, you couldn’t help but join in, just as you did before.
I could make you satisfied in everything you do
All your secret wishes could right now be coming true
And spend forever with my poison arms around you
No one’s gonna fool around us
No one’s gonna fool around us
So glad to meet you
Angeles
“I love you, Dean Winchester,” you whispered, loving the way it sounded now that you could finally say those words out loud.
He kissed the top of your head and murmured “I love you too, Y/F/N Y/L/N. And I’m never letting you go again.”
You knew from his voice and the way he looked at you that he would make good on his promise. The two of you were about to spend the rest of your lives in each other’s arms, and to you and Dean, that was perfect.