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It was weird sometimes. As Anael, Castiel had been so in awe of his commander that he would never have dared to consider the idea of making their relationship anything but that of a commander and her lieutenant. But she had chosen to fall, and when she did, Castiel had believed her lost forever. Meeting Anna Milton had startled him greatly, and he couldn’t help but be pleased when she remembered how to protect herself from him and Uriel.
Orders may be orders, but now, he had conflicting ones. Zachariah told him to kill Anna. Dean told him to let her live. And Michael’s orders were to obey Dean’s commands until such time as his mission was complete. He didn’t take long to make his decision, and he turned on Uriel to save Anna. “I’m sorry, Uriel. We’ve fought together often, you and I. But orders are orders, and I must follow them. Anna is under my protection now.”
“We’ll see about that.” Uriel lowered his blade and flew off, probably to report directly to Zachariah. But clarification had never come, punishment had never come, and Castiel and Anna became fixtures in the Winchesters’ lives.
It didn’t take long for Dean and Anna to become intimate. And for the first time, Castiel understood jealousy. Sort of. He had known Anna so much longer, loved her since before he even knew the word. And Dean was placed in Castiel’s charge, to protect and care for. He didn’t understand how he could be jealous of both.
Anna took his hand as they stood outside Dean’s hospital room. “Sam’s starting to scare me.”
“Only starting? I don’t know what Ruby’s doing to him, but his eyes when he killed Alastair… a lesser man would have had black in them. The hatred, the pride… I hope that it’s just because of what Alastair did to Dean, but I don’t know. The demon blood within him…”
“Ruby’s trying to help. She’s misguided, she thinks Sam can defeat Lilith when it’s got to be Dean, but she means well.” Castiel shook his head, but Anna reached up and touched his face. “I know, you can’t interfere unless Dean gives you orders to. But isn’t there a grey area where you could tell him what’s happening to Sam?”
“I’m already on very thin ice with Zachariah for protecting you. He believes that I’ve become compromised, that I’m developing emotions and doubt.”
Anna scoffed. “You’ve had emotions and doubt as long as I’ve known you, Cas. It’s why I made you my lieutenant. It’s why I was so glad to see you when you and Uriel came after me. If any angel could learn to question, to start thinking for himself… and here you are, the fulfilment of those old hopes and dreams. I’m proud of you, Cas.”
“It’s not always good. You wouldn’t be proud if you knew…”
“That you love me? That you love Dean? I know, Cas. Dean and I have just been waiting for you to figure it out yourself. Dean’s not too sure about it, but I say that if an angel can learn to love, he should be encouraged, and I’ve waited so long for you to get here.”
Dean confirmed that he was okay with sharing Anna, and after that, it didn’t take him long to get on board himself. And now, Castiel was faced with the prospect of losing one or both of them. They and Sam and Ruby were going to take on Lilith tomorrow, and it made him face the prospect of the briefness of a human life. Dean was bound for Heaven. That had been guaranteed since he was raised from perdition. But Castiel would be busy with other work, and couldn’t visit often. Anna’s fate was much less clear. Anael had no soul, but had she been given one when she became human? Would it be welcomed to Heaven where Anael’s grace could no longer return? Even if she did, she and Dean would be separated, in separate Heavens. The three of them would never truly be together again.
Prayer didn’t come naturally to angels, but tonight, Castiel prayed that defeating Lilith wouldn't mean that he was left alone.