After Dean dies, Castiel continues to watch over his offspring, and they always tell stories about the Winchester family’s guardian angel, a man with dark hair and a trenchcoat, that he’s responsible for their lost objects suddenly turning up in the place they swore they checked four times, or for the small things like their car holding out until a gas station when the needle was on E for the past five miles. Three generations down, the stories are still strong, and Castiel will often appear just to watch them, occasionally going up to speak to them.
"How are you?" he’d say, and a boy, fourteen years old, freckled and green eyed, would turn around looking confused or even irritated, about to ask who the hell he was and somehow something clicked.
"You’re him aren’t you?" the boy would say, "Castiel? The angel of our family?"
Castiel would give a small smile and nod once. The boy’s eyes would light up, mouth agape and mind running with questions but then Castiel would look off and disappear, content with how things were going. The boy would run and tell everyone else he saw Castiel, The Castiel.
Though generations pass and pass, and by the time Dean’s line has gone on seven generations, the stories become less and less and some people of the family don’t believe. They will blame small acts of kindness or luck on coincidence. Smile withering, Castiel will visit and be unrecognized, feeling like a shadow, feeling like dust or a rock under their feet and Castiel wondered once if there was ever a point of time he was that to Dean Winchester. He would dispel the thought. Castiel would watch a little girl run around and play with a growing, fond smile, and then parents or police would appear and accuse him of being a pedophile. They blinked and the man was no longer there.
The last time Castiel would try to watch over them, he walked up to a man that looked just like Dean. Like he could be the Dean Winchester Castiel once grew too fond of. (He wouldn’t dare say “love” if he had never said it in Dean’s living years.)
"Hello," he would say, his voice timid and unsure if he should even try this.
The man would turn around, and when Castiel did nothing but gaze at him, he would demand, “What? What do you want?”
"You look just like him," Castiel would blurt on mistake.
"Who?" the man’s bemusement would only heighten when he wouldn’t allow Castiel time to answer and instead rush in, "Who are you?"
Castiel would sigh tiredly. “I’m far too old for this. I suppose I should have given this up long ago,” he would say, mostly to himself, and answer the man, “Dean. You look like him. And my name is Castiel.”
The man would not recognize Dean’s name, or Castiel’s.
"You do not know me, I know," Castiel would say softly. "I never knew loneliness until two ages ago. My purpose is over now, and I will be going."
The man had Dean’s heart, his heightened senses, he would grab Castiel’s arm before he could turn around and demand, “What do you mean? You’re not going to do anything stupid are you?”
Castiel would look at De- the man. “I will not kill myself,” Castiel would tell him, knowing well what he was thinking. “What is your name?”
"Anthony," Anthony would shake his head in incomprehension.
"Dean Winchester," Castiel said and offered a picture from no where. "He was your grandfather- too many greats to try to say and expect you to understand," Castiel would pause. "He was a hero. And my friend."
Before Anthony could say another word the man that called himself Castiel disappeared into thin air. Left with nothing but a picture, Anothony would think to himself, he did indeed look just like Dean.
(Castiel was later found as stone by the grave marked Dean Winchester, head bowed and wings spread like an angel, one to guard him for all eternity.)