As cliche as it sounded, Dean saw his life flash before his eyes. He saw the shitty motel rooms that their father would drop them off at when they were kids whenever he got a lead on a hunt. He saw Sam's shocked face when Dean showed up at Stanford after years of not speaking, and the pranks they pulled on each other after they officially started hunting together again. Next, he saw Castiel in the barn in his trench coat with his shadowy wings spread high.
The memories seemed like they were from another life, one that was simplier.
Suddenly, Ellen and Jo were playing drinking games with Cas, the scene blended into Ellen holding Jo's lifeless body as she saved them all. Bobby playing catch with him and Sam when they were young and innocent. Cas looking deep into Dean's eyes as he growled, "You should show me some respect."
The memories, even the raw painful ones, were a nice distraction as Dean tried to ignore the cold, tingling sensation that seeped up his legs to the stomach wound. Cas was desperately trying to slow the bleeding, but Dean still felt his heavy eyes shut despite Cas' urgent cries to keep them open.
This isnt such a bad way to go. Dean decided. Cas' face burned in his mind. He was glad that Sam wasn't here to see this. Dean tried to imagine Sam's reaction when Cas told him.
He would probably try to find a way to bring me back. A part of Dean wished he wouldn't come back. Everyone's got a time. Maybe this is mine. He mused.
By now, Dean's fingertips felt frost-nipped and raw, and he had lost feeling below his waist. Slowly, the memories that danced in his mind faded and crumbled, and he had a hard time retrieving them.
I guess it doesn't even matter anyways. Dean slowly felt himself float away from his body, from Cas' hysterical cries.
And for one in his life-
Dean Winchester was content.
And he greeted Death as an old friend.