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When it was all over, Dean greeted Death like an old friend.
The first time Dean met Death he was three years old. He had been playing with the neighbours kids. The girl was even younger, still wobbling and regaining her balance every few steps. She had been following a butterfly for a while now, nearly running into her brother and Dean playing on the swings. Their mothers were on a bench nearby, chatting about this and that. They didn't hear the car coming. The girl had only eyes for the butterfly - she didn't see. Dean heard. Dean saw. Dean acted.
Death looked old and tall but Dean wasn't scared much. His dad was taller, he'd always protect him. Dean just had to protect the girl, who was smaller and didn't run when the car pressed on it's breaks with a loud screeching. Death watched as Dean ran and pulled the girl off the road. They fell back, Dean's head collided painfully with the asphalt. The car came to a stop three paces later. Three paces too late.
Death looked at Dean. Dean looked back. With the cries of the neighbour and his mother's face infront of his Death vanished.
Dean was seven and he felt miserable. He had been copped up inside the same motel room for close to a month now. What started out as a light sniffle had turned into a fever overnight.
That was two weeks ago. Dad was too busy hunting to notice Dean barely getting up to eat anymore. Sam noticed but dad wouldn't listen. This night was the worst. Dean was cold, he was so cold and sweating and his head hurt and he felt gross. Dad was out, Sam was sleeping, Dean was miserable. Dean was dying.
Death sat next to him for quite some time. At first they spent the time in silence, just wasting away the hours Dean had left. Death started humming as Dean started crying. He was just so tired. So exhausted.
She reminded him of his mother. What little he could remember of her at least. Blonde hair, a generous smile, kind eyes and a soothing voice. Maybe Dean could rest here. Just of a little, of course.
He woke to bright lights, beeping machines and a clinical smell. Sam had called dad when he didn't wake up to make breakfast. The doctors said infection. He'd be back on his feet in no time if he takes the antibiotics they gave his dad. Death was gone. For now.
Dean was 13 and he was scared. The monsters were dead. And Dean... Dean was dying.
There was a deep wound in his stomach. He didn't know where it came from, he didn't know who or what did it and he didn't care because regardless of how he got it - it hurt like a bitch. Dean was thirteen and he had hunted Monsters as long as he could remember and none of them ever scared him as much as the blood rushing out between his fingers and the cold numbness settling over his body.
When his dad finally found him Dean starred off into space, mumbling about some boy John couldn't see nor care about as he heaved Dean into the car and back to the motel to fix him up.
Dean never remember his meetings with the reapers and death until well into his adulthood. And even some of those were lost to the greater plans or the limits of the human mind.
Dean Winchester died many, many times throughout his existence. Cursed with life, punished with resurrection and surrounded by death wherever he went.
And when it was all over, Dean greeted Death like an old friend. At last he could rest.