Summary: *spoilers up to 5x3*... What happened in that back room when Dean took Castiel to the brothel? Yeah, I pretty much think this is how it went. (That and I love how utterly petrified Cas looked in that scene!)
"Go get 'em, Tiger," Dean said, quirking eyebrows and handing Castiel a wad of bills. "Don't make me push you."
Well, this was new and scary. Why had Dean put him in this situation again? Ah, yes, the world was ending so he thought it was his job to give Castiel something he hadn't had before. Part of some insane ritual of humanity that felt the need to experience certain situations before death.
Did that mean Castiel was becoming more human each day? He shuddered at the thought.
The woman, he guessed, was probably late twenties. She was pleasing to the eye, as he understood that. But her dressed so little was making him about as nervous as a skittish colt made the entire moment oddly funny.
If you were Dean Winchester that is. He was not. He was an angel of the Lord. A warrior, part of the grand Host of Heaven. He had been there to greet the shepherds, announcing the birth of the Christ child. He was there when Paul went on his journeys across the Mediterranean. He was there during all the human wars, plagues and famines.
And yet, here he was, with a voluptuous woman standing in front of him, trying desperately to get him to agree to sleep with her. It was completely unhinging and ridiculous.
"So, what would you like, Mister?" she said, swaying her hips in what was a suggestive manner. Castiel just gulped and stared wide-eyed.
"Wouldn't you like to see something worthwhile?" she said, coming closer to stand next to him. She began loosening his tie and he nearly jumped into the air.
"Please, really, you don't have to do this!" he said, backing away across the satin bed that he'd been sitting on.
"Oh, but I can do anything you want," her sultry voice exclaimed. Chastity – that wasn't her real name, Castiel knew because he pulled it out of her head that her real name was Mary Duncan – was tugging on his trench coat, inching the fabric off. "I can do anything," she said, crawling over to him. "You," she curled up next to his shoulder, hands on his chest. "Want," a final note, said against his ear, lips nearly touching.
He turned to stare at her and saw something from before he hadn't seen: her life. Her disruptive childhood, her mother drinking herself to death, her father – who did love her – leaving her alone with her grandmother because he hated his job at the post office. He recognized how much she both hated him for it and herself.
She was just a lonely, unloved woman. She needed to be reassured, and Castiel decided to take it upon himself to let her know this.
"Your father does love you," he said, in a voice that was calmer than he had expected. "He left only because he hated his job at the post office."
Castiel watched as the woman beside him went from sultry to scared, then angry within seconds. She slapped him and punched his chest. He hoped her hands were not hurt.
"Stupid bastard! Don't you dare talk about my father!" She screamed once more and jumped off the bed, out into the hallway.