Requested By: yami1269

Imagine: You and Dean spent a lot of time before the two of you fell in love. one day you make a deal with Crowley and don't tell Dean until it's too late.

Seventeen years. That's how long you had known the Winchesters. You were going to a small high school in Nebraska when they joined the school. There was something different about them, but you didn't know what it was. One thing was for sure, the Winchesters had you hooked from the moment they came into your life.

Dean made multiple attempts to flirt with you in school, but you shut him down every time, which both annoyed and intrigued him. One day, you caught Sam studying in the library and decided to approach him. When you did, Sam immediately tried to hide his book but you were able to clearly identify the title of it.

"You're reading lore," you stated and Sam shrugged his shoulders. "It's for a class," Sam lied. You smirked as everything began to make sense. They were hunters, just like you. "Oh, really? I thought maybe you were trying to gather some information on how to kill the werewolf in this town," you replied, nonchalantly sitting down in the chair next to Sam.

Sam swallowed thickly, his eyes never looking away from you. "What?" he asked. "You know, the five different murders, all with their hearts ripped out. The logical guess is there is a werewolf in this town," you stated.

"You're a hunter?" Sam questioned. "So are you, and I'm guessing Dean," you responded, making Sam smile. "We should tell Dean," Sam suggested and a slight blush dusted your cheeks at the mention of his name. Sam smiled as he pressed, "He likes you, you know?" You let out a laugh before saying, "Yeah, me and about half the other girls in the school."

Sam laughed at that and let it go, promising to keep your secret of being a hunter from Dean until you were ready. But that secret wasn't kept for long. You were hanging out with Sam and Dean in their motel room when the werewolf decided to target the three of you.

Dean insisted that you stayed in the bedroom because you didn't know what was out there. However, when the werewolf moved to attack Dean, you quickly shot and killed it. When Sam wasn't shocked about how you killed the werewolf, Dean demanded an explanation. An hour conversation later, you and the Winchesters were making promises to text each other if any of you needed help.

John came home later that night and you explained what happened. He was distant and didn't say anything to you and the next morning the Winchesters were gone. But, Sam and Dean both texted on a regular basis and when John went missing, they immediately came to you.

You spent the next year with the Winchesters, and it was like nothing had changed. You were best friends with the Winchesters. But, after John died, you and Dean grew closer. You did everything you could to make him feel better. Despite your inner protests, you fell in love with the elder Winchester. The two of you spent every waking moment together and after a drunken night together, Dean admitted that he was in love with you too.

The two of you were together in a completely loving and committed relationship and everything was really great. That was until things started coming up with Sam and Azazel. It was a whirlwind of emotions that all climaxed when Sam was taken by the yellow-eyed demon which led to his death.

When Sam died and Dean sold his soul you were heartbroken, completely shattered. You were confused and afraid to lose either of them. But there was one thing you were sure of, and it was that you couldn't let either of them die.

So, you summoned every crossroad demon you could until finally one of them told you who the big boss of the crossroads was. Someone by the name of Crowley. You hunted down Crowley and when you finally met with him, you were the definition of a mess. "Y/N, it's so good to finally meet you," Crowley told you.

"I want to make a deal," you stated. "So I've heard, your soul to save Dean's, right?" he asked and you nodded your head. "I'm afraid I can't help you," he replied. "Why not?" you questioned. "The Winchesters are getting what's coming to them," Crowley replied with a small smile.

"Death is an easy way out if what you're doing is trying to punish them," you told Crowley, trying to get him to take the bait. "Is that so?" Crowley asked. "Dean and I are in love and Sam is my best friend. If you want them to suffer, then take away something they both love," you responded, hoping that he would take your suggestion.

Crowley thought about the offer for a few seconds before finally agreeing. "One more thing," you told Crowley and he raised his eyebrow in response. "Dean doesn't find out. You make him think he's going to go the Hell. That way when it's time for me to go, it's too late for him to do something stupid," you stated and Crowley nodded his head in agreeance. A small smile formed on your lips at the thought of Dean and Sam both being alive and okay and you pressed your lips to Crowley's, sealing the deal.

You then left and went back to where the Winchesters were. The next year was spent with you and Dean growing so much closer. Every day your heart broke at the thought of not having him with you. But, you would rather have it this way than watch him be torn apart by hellhounds.

"We have a hit on Lilith," Dean told you, wrapping his arms around your waist from behind as you stood at the stove cooking breakfast. You immediately leaned into his touch, turning the stove off so the food wouldn't burn. You turned to face Dean with a smile.

"Where?" you asked. "New Harmony, Indiana," Dean replied. Your smile grew at the thought of finally stopping Lilith but it quickly fell when you realized that you're time was almost up.

Dean noticed and placed a quick kiss on your lips. "Y/N, I know this isn't fair to you, to watch my time run out, I'm sorry," he told you. You smiled softly at him as tears began to form in your eyes. You wanted nothing more than to tell him that you were the one who was going to die. But you couldn't. You couldn't risk him trying to take your place. So instead you pulled him into a long, passionate kiss. "I love you, Dean Winchester," you told him.

Dean smiled before replying, "I love you too." He then led you to the dining room where Sam and Bobby were. You all discussed a plan and then you were on your way to New Harmony. Your nerves were shot with anxiety as you approached the town, hoping everything would turn out okay.

It didn't take long for you all to locate the little girl Lilith had been possessing, but the problem was that Lilith was no longer in the little girl. Instead, Lilith was possessing Ruby's body.

Your hand was held firmly in Dean's as you all faced Lilith who had a sickening smile on her face. "Tell me, Dean. How have the hallucinations been?" Lilith asked, but Dean didn't respond. "How about you, Y/N? Care to share?" she asked, making your heart slam against your rib cage. This was it.

"What do you mean?" Dean asked, looking at you. "The hallucinations you've been seeing, Dean. They're fake. Y/N's, however, are very real," Lilith stated and Dean's eyebrows furrowed in confusion, his eyes never leaving you. "What the hell is she talking about?" Dean questioned. "Dean, don't be mad at me, please," you began and he stopped you by saying, "Don't give me a reason to be mad at you."

"You and Sammy, you're all I have, I couldn't stand the thought of losing either one of you," you explained and Dean inched dangerously close to you. "What did you do, Y/N?" he asked, his voice low. You looked over at Sam as a tear fell from your eye. Sam looked scared, as if what you were going to say was his worst nightmare.

"She sold her soul to save you two," Lilith stated, smiling before she continued, "And now the two of you are going to watch her get torn apart by hellhounds." Dean looked heartbroken and angry and Sam just looked shattered.

"Why?" Sam asked, his voice cracking slightly. "You two need each other. And I love you both too much to watch you die," you replied and Dean let out a sigh as he rested his forehead against yours. "Please, don't leave me," he whispered, making more tears escape. You captured Dean's lips in a kiss that expressed all of the love you felt for him and he responded with just as much emotion.

The kiss was soon interrupted by Lilith saying, "Well I've had enough of this." She then opened the door to the room you were in and two hellhounds stood in the doorway. Taking a step away from Dean, you swallowed thickly as the hellhounds began running towards you.

Before you knew it pain erupted throughout your entire body and all you could hear were the cries of Sam and Dean begging you not to leave before everything faded to black.

Hello my little monsters,

Thank you all so much for reading and for all of your votes and comments. I love you all and all of you are amazing!

Always Keep Fighting!

~Caela~