Disclaimer: I don't own the rights to Supernatural
Note: This is before Dean goes to Hell. He gets to say goodbye to Sam, but it's not the right Sam. Meet eight year old Sam Winchester asleep in his bed as a very older brother Dean says goodbye one last time.
Dean opened his eyes. This wasn't Hell. . . .not yet. Instead, he found himself standing inside a small, tacky living room. She held up her end of the deal, which was surprising. Demons always lie and cheat and scam.
In return for his soul burning in hell, Sam would live, Dean gets a year, and he gets to say goodbye before he leaves. It was such a sweet deal, Dean couldn't refuse. His soul meant nothing if Sam was dead. So, Dean kissed the demon like no other. His mind reeled of knowing he just sealed away his faith, it made his bones rattle and skin crawl at the thought of making a deal. But, it was for Sammy. . . .
Dean recognized where he was, it was his old house, where Dean, Sam and their father lived. It was the closest thing to a home for a broken family. "What the hell?" Dean said as he took in his surroundings. "Why am I here?" Dean cursed. He was supposed to say goodbye to Sam, not his old home. Dean glared as a little boy came out of a room talking on a phone. It was younger Dean.
"Yes, he's sleeping." His younger self said. Dean kept himself hidden in dark room. "I'll take care of him, don't worry." Small Dean said with a smile and it made future Dean blanch and hang his head. Suddenly, he felt so small. . . ."Don't you wanna say goodbye?" younger Dean asked into the phone. Everything clicked in Dean's mind. This is where he says goodbye. Dean felt a little cheated, he didn't want to say goodbye to his eight year old Sammy. But, he didn't complain as his heart dropped immensely. It was his only chance. Dean waited a little while longer until his younger self walked into another room and closed the door. He heard the TV come to life. This was Dean's chance. He quietly slipped into Sam's room and closed the door soundlessly.
Dean almost cried at the sight. Sam lay curled up tight under his blankets, snug in his bed. He looked so safe, so innocent. Dean breathed heavily as just stood there looking at his younger brother. Then he remembered that he didn't have much time. . . .
He pulled up a nearby chair and set it next to Sam's sleeping form. He smoothed out the blankets. "Hiya, Sammy. . . ." Dean whispered. "This may be last time I ever get to talk with you and I'm at a loss for words. . . .Can you imagine that? Me having nothing to say." Dean chuckled to himself. Sam put up Dean's rambling and snappy remarks the whole time. "When you wake up tomorrow, I'll be there. And I'm gonna be there for you always. . . .I tried to come back to you, Sammy, to say goodbye. But, uh, things got a little messed up. Silly me, silly Dean always getting into trouble. But, don't worry; I'll be gone soon so you can rest." Dean tried to joke a little, but it hurt. "I want you to remember that everything we did, everything we went through. . . .it was worth it. All those lives we saved, all those demons we pissed off, all that trouble we got into. . . .I don't regret it. Not one bit. And, you better not either, when I'm gone." Dean said sternly. "You hear me, Sammy? Don't you dare blame or regret our life for when I die. Because it was the best. The best life I could've lived with you. . . .Sam and Dean the best hunters ever. And all those wonderful things we did, you're gonna do. . . .even when I'm not there." Dean felt tired. Eight year old Sam slightly whimpered and shifted closer to Dean but was still fast asleep. Dean gently put his hand on Sam's head. "Don't be sad. It's what I'm here for. I'm always gonna be there to save you. Always. Because that's what big brothers do." Dean smiled down at Sam. Dean felt so tired and broken. His time was almost up. "I gotta go now, Sammy. But, I want you to remember something. Get it through that thick head of yours, because this is important. I want you to remember that it's going to be okay." Dean whispered. "It's okay that I died, it is, it really is. Everything's going to be okay." Dean lifted his tired body as he kissed Sammy on his forehead. "I'll be here when you wake up. Remember what I told you. . . .Goodbye, Sammy." Dean looked at his brother one last time before he closed the door.
. . . . . .
"DEAN!" Sam cried as he held Dean's limp body. His big brother was all bloody and broken beyond repair, and he couldn't imagine a life without him. Sam cried into Dean's shoulder. "I'm sorry, Dean. I'm so sorry. . . ." Sam said. But, deep down and in the back of his mind, somehow he knew it was going to be okay. Because Dean told him it would be a long, long time ago.