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Dean attempted to keep a straight face whilst looking at Castiel, which was no mean feat. The poor guy was terrified: sweating, breathing erratic and he stared at Dean constantly, purposely avoiding looking at the scantily clad women walking past.
"Hey," he said to Cas. "Relax."
Castiel leaned forward. "This is a Den of Iniquity. I should not be here." Dean nearly choked on his drink.
"Dude, you full on rebelled against heaven. Iniquity is one of the perks." A woman (barely dressed) approached them, and Dean put down his drink. "Showtime."
"Hey," she said, smiling at them both, and Cas's eyes nearly bugged out of his head. "What's your name?"
Castiel did his best to avoid her gaze, and Dean speculated as to whether angels could self-combust. He looked like he was going to explode, cry or faint. Dean suspected the latter could happen, so he pressed on.
Ignoring Cas's silence, he said, "Cas." Castiel jumped, and turned, if possible, even paler. "His name is Cas. What's yours?"
"Chastity," the woman replied, smiling sweetly. Dean yet again fought the urge to laugh.
"Chastity," he repeated. She nodded. Cas picked up his drink and started gulping it, draining half the glass in a couple of seconds.
"Wow," said Dean, sniggering internally. Damn, he should've gone to drama school. "Is that the kismet or what? Well, he likes you, you like him, so dayenu."
Chastity (oh God, that name) tugged Castiel up by the sleeve of his trenchcoat.
"Come on, baby." Cas gave Dean a look reminiscent of a lamb to the slaughter, and Dean caught him on the way past.
"Here," he said, holding out a wad of money. "Take this. If she asks you for a credit card - no, ok? And just stick to the basics. Do not order off the menu. Go get her, tiger."
Castiel did not move, and Dean could tell he was simultaneously fighting the urge to run and the need to ask what "ordering off the menu" was. And Dean was just not ready to answer that question.
"Don't make me push you..."
Castiel took the money and turned to his fate, and followed Chastity through the door at the back. She took him past several doors until she found the one she wanted, before pushing him inside and shutting them both in.
Cas's breathing picked up and he began looking for ways to escape. He could just fly away...but that would mean abandoning both Dean and the mission.
"So...Cas..." Chastity purred, pushing him backwards onto the bed. "I've never met a Cas before." Castiel didn't answer, and unconsciously backed away from her into the headboard. Chastity followed, gripping onto his tie and pulling almost loose.
Cas decided there was only one thing for it.
"It was not your fault your father, Gene, left you," he said, turning and looking her straight in the eyes. He could see the raging turmoil there, the guilt and the depression. He merely wished to comfort her. "He just hated his job at the post office."
Instantly Chastity's whole demeanour changed. "Get out!" she screamed in a shrill voice. "Shut up, get out you jerk! Don't you dare say...oh my God!" She wrenched Cas upright and shoved him out the door. He was too stunned at her reaction to warn her about blaspheming against God.
"Get out of my face, leave me alone! Bastard! Screw you, jerk!"
Cas noticed Dean standing in the doorway to the club, nearly killing himself laughing. Castiel pretended not to notice.
He decided not to blame Dean, if the experience had made him laugh.