Mostly non-cannon. The middle segment is a 90% reflection of seasons 4-8.
- Twenty five years earlier -
11 year old Jimmy heard voices. The voice tells him to not tell anyone because no one would believe him. Jimmy knew that to be true and asks what the voice wants. The voice says he's an angel and he wants to use Jimmy's body for a little while. Jimmy was unsure, he didn't want to be possessed. Jimmy would constantly ask the angel why he wanted to use his body and no one else's? The angel would always give the same reply, "Because you're special, Jimmy. No one else would do." Eventually, Jimmy gave the angel the okay to use his body. A moment later, his insides felt like they were on fire, his consciousness shut down, he was no longer Jimmy.
Near by, John left his two sons alone at a low end motel room. 8 year old Dean was used to staying alone and keeping his five year year old brother, Sam, safe. Sam slept in the bed near the bathroom. His small body barely took any space and when John left to 'hunt', Dean made sure to lock up tight and lied down next to Sam. Dean thought Sam was sleeping, only to hear little whimpers, Dean peeked over the dark blond child, "Sam, are you crying again?" Sam didn't answer, just kept crying. Dean sighed as he lied on his side at the edge of the bed, "I don't like Dad leaving either, but this is what he does. Just get some sleep, maybe we'll go to the park tomorrow. Sam bit on his lip, "Really?" Dean sighed, "Yes, Sammy, now go to sleep."
The next day, after making lunch for the two of them very carefully and cleaning up, Sam reminded Dean of the park. Dean didn't think that Sam would really want to go, but his eyes were so full of promise, how could Dean say no? Dean locked up after them, making sure that things were hidden and he had an extra key card, which he kept zipped in a pocket. He took Sam's hand and walked him to a park he remembered seeing when they pulled into town. Dean made sure to watch Sam very close and had to remember to have fun. He took his eyes off Sam long enough for Sam not to be where he saw him last.
"Sammy!?"
Sam smiled as he walked up to Dean with an older boy, "I'm right here, Dean. I met a new friend!" Dean looked at Sam and the stranger. The boy held out his hand, "My name is Castiel." "That's a weird name." Dean said flatly as he took Castiel's hand. "I suppose it is..." Castiel said, looking away, he explained to Dean that Sam wanted a drink of water but didn't know where the drinking fountains were, so he helped him, and brought him back safely. Dean thanked him and invited him to play with him and Sam. It was nearly dark when John pulled up to the park in the black impala, Dean assumed he got his note. He rolled down the window, "Sam! Dean! Come now boys, we're due in Minnesota."
Dean knew what that meant and sighed, "Time to go, Sam. It was nice playing with you, Castiel." Castiel nodded, "Like wise." Sam went a head of Dean. Dean looked at Castiel and impulsively kissed him quickly. Dean sluggishly went to the impala and sat down beside Sam. Dean looked out the window at the boy with the most dazzling blue eyes. When they were too far away, Dean slumped in the seat. "What's the matter?" Sam whispered. Dean didn't answer, Sam knew Dean liked Castiel and wanted to play more with him. It was rare to see his big brother upset over a friend, then again, it was rare that they'd even have friends with all the traveling they do. Dean pushed his tears back and figured he'd never see Castiel again.
- Five years earlier to angelic damnation -
Castiel was more than thrilled when he was told that he'd be the Winchesters' guardian angel. It had been 20 years since he last saw them. He left Jimmy's body the night the boys left and was able to obtain his body again. The day after he reunited with Dean, he was saddened that Dean had forgotten him, even feared him. He wanted to be their friend again so badly but didn't know how to go around it. He also had a job to do, and after so many years, he wasn't the same Castiel, he was emotionless. More and more he spent with the brothers, he started to have emotions, he felt confused, guilty, and eventually he felt joy.
It wasn't easy to build on the bond he had with Dean several years ago. Dean was untrusting, drained, and cynical. While it was easier to make a friendship with Sam again, Castiel really wanted to be close to Dean. He didn't understand why, but it meant everything to him if he could. More work and time, and Castiel was maybe closer to Dean then he's ever been. They trusted each other with everything, Dean was able to smile and joke around again. He loved Dean like a brother, but started to question his feelings each time he'd see Dean with a woman. How he urged to be the one in Dean's arm, kissing Dean's lips, touching Dean's beautiful body, and run his fingers through Dean's dark hair.
Castiel knew he had to lock those desires up. As time went on, he had to be Dean's friend as well as betrayer. Seeing Dean hurt was the last thing he wanted to see in Dean's hazel eyes. He thought he was doing what was best for the brothers, even working for Crowley, and breaking Sam's soul wall. His hasty behavior had gotten him in so much trouble and he thought his time in purgatory would serve him as punishment for hurting his beloved human and turning his back to heaven. When he reunited with Dean and met Benny, Castiel's heart broke a little. Dean befriended and trusted a vampire and as warm as he was to him, Dean still had a cold air towards Castiel. Castiel believed that he deserved to stay in that terrible place, his punishment was far from over.
Being rescued and reunited with the brothers left Castiel depressed and suicidal. He was ashamed for what he had done to heaven and to Dean. As much as he tried to be happy, he felt like he had a hole Jimmy's heart; a heart that felt like it belonged to him to use. He never forgotten the sacrifice Jimmy did for him, and after all the times he's been brought back, Castiel no longer felt Jimmy within him. He was unaware of the brainwashing Naomi had done to him by the device in his eye. One day she summoned him to her and she made him kill hundreds of Dean clones. He was so controlled, he felt nothing by doing so. When it came to time that he was to kill the real Dean, beating him with the angel tablet, the control changed.
Dean pleading for his life awoke Castiel's compassion and love for Dean. He didn't want to hurt him but Naomi's forcefulness was too much, until he realized that even she was going too far and disappeared with the tablet. He traveled all over, avoiding angels and the brothers. He thought that as long as he was away, that kept Dean safe. He tried to redeem himself, unaware of what was really at stake. When his grace was stolen and thrown from heaven, Castiel awoke in time to watch his brothers and sisters being casted from heaven like shooting stars.
- present -
Dean and Castiel were at a bar. Being human was difficult for Castiel. This wasn't his first time being mortal, but the first time without his grace, he no longer felt like an angel; which had felt alien for him. He nursed a beer, feeling pity for himself. Dean also drank a beer, eyeing the depressed blue eyed man. Dean sighed, "Hey Cas, have I ever told you about a kid Sammy and I played with when we were kids?" Castiel shook his head slowly, momentary unaware. Dean took a swig and swallowed, "Dad drove us through Illinois for a night n' day, took Sam to the park. He wandered off and met this kid." Castiel looked at Dean, "Kid?" He played stupid, but he knew what Dean was talking about. Dean nodded, "Forgot his name, I know it was weird though. He had the most bluest eyes I've ever seen in my life. Blue like the sky, never saw a pair like those since... at least until..."
"Tell me more." Castiel said, hoping to hear more of what Dean remembered. Dean had to think, "He was nice. He was an older kid, but you wouldn't have noticed. There was a thing about him that I was attracted to, though I didn't consider it then. Spent the day with him. He kept Sam safe and we bonded quickly, only for Dad to come and take us away. Never thought I'd see him again. I remember crying to myself to the next place." Then Dean chuckled, "Almost can say he was my first crush. Spent so many years fucking so many women, he was always on my mind. Then when I met you, it was like I was with him again and felt the same way about you as I did him."
Castiel opened his mouth to speak but no words came out. Dean looked into Castiel's eyes. He has looked into his eyes several times before but this time, he really looked. Dean gasped, "How didn't I see this before?! You're... you're... him." Castiel looked down, "I was hoping you'd remember sooner... like... 5 years ago sooner." "You could have told me!" Dean raised his voice. Castiel knew he was right, but yet again, that would have been awkward regardless.
Dean calmed down, "I'm sorry. I just never thought. I was sure I'd never see you again. So that was Jimmy as a kid, uh?" Castiel nodded, "Yes. I borrowed him, even way back then. I just really wanted to meet you and didn't want to wait until I was actually supposed to with Uriel."Dean went silent, turning away. Castiel wasn't sure what was going to happen next. Dean turned to him, placed his hands on Castiel's face and kissed him quickly and hard. When it was over, Castiel was stunned and Dean smiled, "I never forgotten." He lowered his lips onto Castiel's lips again, kissing him lovingly.