Chapter Text
Three days. In three days the hell hounds would come to take Dean away. Time was quickly running out, and no matter how hard everyone tried, it seemed like there was no way of getting Dean out of the crossroads deal. Not that he seemed to be overly concerned by his impending doom. He was more concerned about eating what he swore was the “best apple pie in the world” for the last time.
When Dean brought it up, Sam insisted on staying at the motel to sleep, which you knew was code for “research and stress out all night about Dean going to hell”. You would have stayed back to help Sam, but there was no way you could have said no to Dean after he practically begged you to go with him by using those damn puppy-dog eyes. You were a sucker for those eyes, and he knew it. The diner that sold the famous pie was located two hours away from where you and the boys were staying, and the weather forecast called for a rainstorm sometime that night, but that didn’t stop the two of you.
The car ride to the diner and the eating of the “best pie in the world” went by quickly, probably because of all the talking and singing you and Dean did. The two of you had always had a strange relationship. You knew the Winchesters ever since you were all were kids, and you and Sam had become best friends almost instantly. Dean on the other hand was always a bit distant, even as a child. But eventually, the two of you grew close, especially after you became a full-fledged hunter. The biggest change in your friendship with Dean was your own feelings for him. You were in love with Dean Winchester. You had been for a while now and you knew that those feelings weren’t going away anytime soon. But Dean was. So you buried them away and put on your best poker face for him during his last days.
“Was that not the best pie you’ve ever had or what?” Dean asked with a grin as the two of you drove back to the motel.
“You know, I had my doubts at first, but that was pie was pretty damn impressive Winchester,” you replied with a chuckle. It really was, but you knew that at that point, it could have tasted like total crap and you still would have said the same thing to keep that smile on his face for as long as possible.
“Son of a--!” Dean suddenly exclaimed as the Impala started to slow down. “Don’t do this to me baby, not now.”
You then realized that the car was making some odd noises. You weren’t a mechanic, but you knew for sure that those weren’t good signs. Dean did the best he could to pull the car over to the side of the road, right before it broke down completely. Usually something like this wouldn’t be a problem; but it was dark out, the road had been empty the whole time you’ve been on it, and the thunder had started.
“Alright Y/N, you call Sammy and let him know what’s going on while I try to call for a tow,” Dean instructed with a huff.
“A tow? Since when does Dean Winchester trust a tow truck with his precious baby?” you asked him, your voice laced with fake shock.
“Since Dean Winchester forgot all of his tools back at Bobby’s house,” he grumbled.
By that point it was raining heavily, accompanied by thunder and lightning. You dialed Sam’s number, but the call wouldn’t go through. Dean seemed to be having the same problem with his phone.
“No cell service?” you asked him, already knowing the answer.
“Nope. Nothing. And I haven’t seen any other cars on this road since we left the diner, so I’m guessing that our chances of being rescued are slim,” Dean told you.
“Well at least it happened after we got our pie and not before, that’s something, right?” you offered with a shrug.
“Yeah, yeah. You’re right,” Dean nodded, a hint of a smile in his voice.
The two of you sat without talking for a few minutes, just gazing out the window and listening to the sounds of the storm.
“Y/N?” Dean asked, breaking the silence.
“Mmmm?” you replied while watching the flashes of lightening outside.
“I don’t wanna go to hell.”
You turned to face him, but he was staring down at his hands. “Of course you don’t Dean. But we’re gonna find a way to save you, okay? Sammy’s researching as we speak. He’s gonna find something…anything…”
“It’s too late Y/N,” Dean muttered, raising his head so that his green eyes could stare straight into your Y/E/C eyes. “If there were a way, we would have found it already. I’m going down there, it’s a done deal. I know I’ve been acting like it’s all good, but it’s not. I’m scared, Y/N. I’ve never been so damn terrified in my entire life.”
After a brief pause, “I’m sorry, Dean,” was the only thing you could say.
“I’d do it again though,” he continued. “If I could sell my soul again to save Sammy, or even you Y/N, I would do it. So it’s worth it, right?”
“I don’t know if it’s worth it, Dean, but I know it isn’t fair,” you said as the tears started to fall from your eyes. Dean then reached over to you, and took you in his arms. “I don’t know how we could face a world where Dean Winchester doesn’t exist,” you confessed through your sobs.
“I’m sorry, Y/N,” Dean said, echoing your words while gently wiping your tears away.
You and Dean sat like that for a few minutes, comforting each other. You lifted your head to look at Dean and saw that he was looking back at you. You stared at him for a few moments more as you felt a sense of courage wash over you, causing you to reach up and gently press your lips against his. Dean’s arms tensed around you for the entire second the chaste kiss lasted, but he relaxed right when your lips pulled away from his. Your heart was racing in your chest, and since you were pressed up against Dean, you could feel that his was beating just as fast. Before you even realized what was happening, Dean captured your lips in a passionate kiss, exploring your mouth with his tongue and sliding his hands along your waist.
You kissed back with just as much urgency, nipping at his lips and running your fingers through his soft hair. After a while, Dean’s mouth moved to sucking at patches on your neck and you removed his flannel shirt from his shoulders. He stopped suddenly when he realized what was about to happen and pulled away to meet your eyes.
“Are you sure, Y/N?” he asked, breathing heavily.
“I want this, Dean,” you answered looking down at your hands. “I want you.”
“I want you too, Y/N; so much,” Dean replied, tilting your face up to his once again. “But I don’t want you to do something you’ll regret once I’m gone.”
You wanted to tell him right there and then about how you’ve dreamed of this moment for so long, and how you never wanted him to leave the safety of your arms. You wanted to tell him that you cherished every moment you’ve spent with him, and that your only regret was not telling him all of this years ago. But you didn’t. Instead, you placed your palms on either side of his head and kissed him harder than you had two minutes ago, pouring all of your love and desire into the kiss.
You and Dean made love to each other that night. You had always known that Dean was experienced when it came to sex, but you were pleasantly surprised by his tenderness. He paid close attention to you and your body, and figured out your needs before you did. He touched you in all the right places, getting whimpers and moans out of you while telling you how beautiful you were and how thankful he was to have known you. You tried your best to be just at attentive to him. You held him close the whole time, whispering words of adoration into his ear and kissing him everywhere your mouth could reach. You treasured every time he cried out your name in pleasure, and every moan that had escaped his lips. When the both of you reached the climax, you were overcome with bliss. It was a feeling you had never known before, and something you knew you would never feel again with anyone else.
When it was over, Dean gave you his large shirt to wear while he slipped back into his jeans. He then settled on his back and pulled you down to him to that you were laying on his chest with his arms wrapped securely around you. Then he began to sing. You had heard him sing before, many times, but this time was different. This time, he wasn’t being silly or loud. He was singing Angeles, a song that you had loved for a long time. Never in your wildest dreams would you have thought that he knew it too. When he got to your favorite part of the song, you joined in; singing softly.
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
Dean stroked your back and planted small kisses on the top of your head while you tightened your grip around his waist as the song ended. No more words were said as the two of you lay there, your breath and heartbeats mingling together just as your voices had. You fell asleep wrapped up in each other not long after.
Two days later, Dean was dragged to hell. Seeing him like that, with his body ripped to shreds and his usually vibrant green eyes flat and empty, almost destroyed you. You didn’t know if you would ever see Dean again. Hell, you didn’t even know how he felt about you after that night. Neither you had mentioned it once Sam and the tow truck rescued you. But what you did know was that you had to stay strong for Sam and for Bobby and for yourself. And for Dean. You knew that he would want you to be as brave as you could be.
You also knew that as long as you lived, you would always cherish the night you spent wrapped up in a doomed man’s poison arms; in an old car, on the side of a deserted road, during a rainstorm.