Dean jumps through the portal. Not shorty afterwards Castiel does too. Dean recognizes the place he is in. He arrived in a small food market.
As Castiel is falling from the sky, he realized that he is in a forest. He wasn't to happy about that.
Dean checks his pockets for some money. He finds twenty dollars, and a credit card. Thinking that it should be enough just for one night. He goes to a diner and orders a double bacon cheese burger with a side of fries.
Once he is done eating he leaves the waitress the twenty with a 13 dollar tip.
Castiel finds a path that leads to a road. He decides to walk along that road for quite some time. As he is walking he sees a car driving by. He saw Dean in the car, but he thinks not. "It's just an allusion."
Dean arrives to a motel and rents a room for the night. Dean walks into his room, as he is walking in he see's a bed. He rushes to the bed. As he is lying down he pulls out his phone, and calls Sam. "Sam I'm back, not sure if Cas is, we just have to see if he turns up." Dean said. "Alright, cool. I'll see you tomorrow I guess." Sam said quite surprised.
Not shortly afterwards he passed out. It's 12:30 am, and Castiel walks into Dean's motel room ; to see him passed out. Castiel sits down in a chair next to the bed. Sure enough Castiel passes out.
Time is now 9:30 am, Dean opens his eyes to see Castiel sitting next to him. "Hello Dean", Castiel said in a deep voice. "It's nice to see that you made it out. I Have something that I need to tell you. I love you Cas. I thought that once I left Purgatory that I would never see you again." As a single man tear runs down his face, he leans into Castiel and gently presses his lips against Castiel. Dean slowly released
"I know Dean. I love you too. I just didn't know how to tell you. I wanted to tell you in Purgatory, but I just didn't know how to word it." Castiel grabs Dean by the neck and starts to kiss him. Thinking how soft and smooth Dean's lips are, that he doesn't deserve a man that has protected the world his whole life. The fact that I'm kissing Dean Winchester is just amazing. Being of the fact Dean was made for Michael.
Not shortly afterwards Dean dies in Castiel arms. Castiel just thinking that Dean is asleep, but He try's to wake him up. Castiel realized what he did.
"It should of been me. I tried keeping it from you for so long, but now you gone. I'm gonna fix this no matter what it takes. You deserve to live in this world. We need a chance together. Dean Winchester I love you."

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Dean in the empty never
FanficCastiel has just confirmed his feelings to Dean, and later Dean is taken by the empty. So Castiel and Sam search through all the lore to bring him back.