Dean Winchester Imagines

What Hurts the Most

WARNING: Mention of Suicide

I can take getting tortured, stabbed, and being dead for God's sake. But Y/n being gone, I can't handle it. I'm not afraid of many things, not ghosts, demons, windigos, werewolves, or poltergeists. But Y/n dyi... being gone, my worst nightmare come true. I've tried everything to protect her, but I failed. I failed Sam; she was like his little sister that he never had. I failed Cas, she was his mentor for everything humans do. I failed Y/n most of all.

One night she and I were laying in bed talking about getting out of the life. Buying a big white house. Having a dog to greet us when we get home from a normal job. Having kids. Y/n always wanted kids. She said she can't stand having an off amount of kids. She likes even numbers. She said she wants two kids. Wanted to kids. 

But because of that damn demon, Y/n will never experience having kids, or being married, or growing old with someone.

I was going to propose to her. I got the ring and everything. I was going to take her out stargazing. She always had a fascination with the stars. It was great timing too. Y/n and I had one of our nights and from then on she had been acting distant. But then I found it; the pregnancy test that read positive in the trash can. At that moment I was the proudest man in the world. I go to find her but I couldn't. I found her phone and she never leaves the bunker without her phone.

But we found a note. A demon had somehow gotten into the bunker and kidnapped her. She was using her as bait to get to Sam and I. We showed up to the address that the demon had left for us. But when we got there Y/n was already bloody and bruised. It made me furious. He just hit the only thing I saw in my future along with my child. But when he plunged the knife into Y/n heart I couldn't control my actions. The demon smoked out before I could kill the bastards. 

I held Y/n in my arms as her life left her body. A life wasted. But not only had he killed the love of my life but also my unborn child. 

When Crowley found out Y/n was killed by a demon, he was livid. He had a soft spot for her. She could charm her way out of everything. Crowley saw her as a daughter. He called us into his thrown room one night and summoned the demon who took the woman I cared about from me. You could guess what happened next. I killed it and enjoyed it. 

Sam, Cas, and I gave her a hunter's funeral. She deserved better. Cremation was the only way to go. I didn't want her to come back as a vengeful spirit. I also made a small coffin and burned it, for my son or daughter I would have had. 

Cas, Sam. I am sorry. I can't take it. I need Y/n in my life. She was my everything. I am going mad without her. You have to understand where I am coming from. See ya when you get to Heaven.

Sincerely,
Dean

Sam read the note out loud so Cas could hear it. Sam wiped away a tear that had escaped his eye. They stood next to Dean's lifeless body with his .45 in his hand. 

"Don' bring him back Cas," Sam said with a tear-soaked voice. "He's with Y/n now." Sam set the note down on the table where he found it. 

"Sam, I don;t understand what I'm feeling," Cas said to Sam as tears were coming down his cheeks.

"You're sad Cas. People feel that way when they lose someone they care about." Sam explained. He wiped his cheek again trying to seem manly but was failing. "I'm going to my room and am going to get drunk," Sam said leaving Cas next to Dean's corpse. 

~In Heaven~

Dean walked into the bunker and was greeted with Y/n sitting at the library tables.

"Dean?" She said with shock in her eyes. 

Dean ran down the stairs and scooped Y/n up in his arms. "Y/n" he whispered. "I must be dreaming."

"Why are you here? How did you get here?" Y/n said confused.

"I couldn't live without you. Like I promised, you die, I die too." Dean looked into her eyes as tears started filling them.

"No, don't cry. I'm here now." He hugged her and she buried her face in his neck and he started to cry tears of joy.

They were interrupted by footsteps walking into the library. Dean looked up and saw a teenage girl standing there looking at him. She had Y/n's eyes, beautiful big and Y/e/c, with long brown blonde hair.

"Who's this?" He says releasing from Y/n.

"This is Cassandra. She would have been our daughter." She said quietly. 

"Hi, dad." Her voice soft yet strong. 

"Hi, Cassandra." I pulled her into a hug along with Y/n. 

Hey everyone. Sorry that I haven't uploaded a chapter in like what seems forever. I promise that I will be ontop of this better since it's 2017! Happy new year everyone! This one made me cry even writing it. Made my sister cry even harder. Anyway, thank you so much for 10.7k reads!!!!! I started crying when I saw that. You are all so amazing and I love the feedback I am getting. Love you all!! Get those typos, probably won't have any since I started using Grammarly. It is a writers best friend! Love you all!!!!!!!