A/N Sometimes you just get tired of fluff and happy endings, you know?
Castiel Novak had lived next to Dean Winchester for as long as he could remember. The Novaks and the Winchesters went way back, the always-there-for-you best friends. Their generational friendship was the thing of town legend. The whole town, small as it may have been, knew that if you messed with a Winchester you messed with a Novak, and vice versa. Nothing would ever break the families apart.
Castiel and Dean were best friends- their younger brothers, Gabriel and Sam, were too. All through their childhood, Cas and Dean were pushed together until it became natural for them to seek one another out at every opportunity. All the way through elementary, middle, and up through high school the boys were thicker than thieves, even if Dean became the womanizer of the school- he made sure every girl knew his best buddy came first. Neither boy ever went somewhere the other could not follow sooner rather than later. When Castiel came out to Dean, the boy just laughed and said,
"Cas, I've known you literally since I was born-" Cas had been born a mere 4 days before Dean, "I've known for years. You honestly think you could keep anything from me at this point?" Cas, of course, was stunned. Dean had been parading naked around Castiel's bedroom just a few days earlier (he had wanted to borrow a pair of Cas's jeans after a shower). Further more, if he knew everything to know about Cas, then that meant he knew about the secret crush Cas had been harboring for him since puberty struck.
Time passed and the boys went to college together- in a new, large city. They shared a dorm room and things started to change. Dean met a girl who didn't know of his family tradition to keep Cas by his side through thick and thin. That gave her the power to tear him from Cas's side and make him "grow up", as she so kindly put it. Slowly, Dean fell in love with her-Lisa- and began spending more and more of his time on her. When she got pregnant in their junior year, Dean was ecstatic and proposed immediately. Cas, still deeply in love with his best friend, didn't begrudge him his happiness, and decided that Dean would never know the extent of his misery, would never know how much he suffered. As long as Dean was happy, Castiel could deal with being slightly less. When Dean asked he helped pick out the engagement ring, and was the smiling best man at the wedding.
More time passed, and things continued to change- Dean became the father of three little girls- the first born to the Winchester clan for six generations. It marked the end of an era, as his best friend had no children to befriend his own kids. Dean named Castiel Godfather of his second born daughter- Lisa's brother being Godfather for the first-born. Castiel found his few relationships lasting shorter and shorter amounts of time, despite Dean's teasing that he was "doing it backwards". Castiel, still with his goal of keeping Dean happy in mind, bought the house directly next to the one Dean put his family in, in keeping with the Novak/Winchester family tradition. Dean visited when he could, often bringing the kids to visit their 'Uncle Cas' so Lisa could have some 'down time'.
More time passed and Dean began to lose his perfectly maintained physique. Despite his best efforts he gained the slightest of beer bellies, while Cas effortlessly stayed slim as ever. Dean became a grandfather and the baby was named after Castiel, being his goddaughter's child. Every night Cas prayed that the child not grow up to be live his namesake- miserable, trapped, and alone. Then the time came when Cas got sick. He hid it as long as he could- which turned out to be the rst of his life. For sixteen months, Dean was blissfully unaware that his best friend was fighting a losing battle against leukemia- until it was too late. Cas fed him lies of boyfriends and business that kept him out of town to hide the truth. It was a lie swallowed too easily by a man busy with his own life.
Time passed. Gabriel, Castiel's youngest brother, showed up of the Winchester doorstep, tears flowing freely down his face.
"Tell me he told you. Tell me he didn't go through all of that alone. Please Dean, he didn't tell me, tell me he told you." When Dean- now 65 years old- finally managed to pry the story from the grieving man, he cried. For three days, Dean felt as though he were in the very pits od Hell, having his heart torn out again and again. He spoke at the funeral in place of a significant other, eyes sore but still spewing tears. He spoke to the Novaks and the Winchesters of his brother, Castiel, angel even in name. He laughed through his tears as he told childhood stories and eventually could speak no more. He left the cemetery and went on with his life. No one told him what they all knew- not even Lisa- Castiel loved him until his dying breath.
Time passed. When Dean finally died, he was 102, and it was Castiel's birthday. As Dean was admitted through the Pearly Gates, he looked for his childhood friend- but he was nowhere to be found. As the gates clicked softly behind him he was told the truth- Castiel had never entered Heaven. He had chosen to remain on Earth, watching out for Dean throughout the remained of his life. When Dean had almost been hit by that drunk driver, Castiel had shoved his out of the way, saving his life. When that car had fallen on Dean Cas had pushed him out of the way of the pointy bits and summoned help. Castiel had taken on the roll of Guardian Angel and was now stuck on Earth-forever. He knew when he made his choice that he would never be admitted into Heaven or Hell, and would be doomed to roam the world an unseen observer forever. Once more Dean sobbed for his faithful brother, only stopping when he was joined by his wife, and eventually his children and grandchildren, his brother, and the entire Winchester clan. Castiel spent his eternity alone.
Time passed slowly after that.