DISCLAIMER: I do not own the Supernatural characters or the show.

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After leaving the brothel, Dean decided he'd take a more subtle approach to giving Cas a great last night. He'd more or less given up on de-verginizing the angel, but still held hope that Cas' puppy dog looks might help him pick up a girl the old-fashioned way. He found a dive bar not far from the brothel. Once inside, Dean told Cas to sit in one of the booths while he got them some beers. Secretly, Dean thought maybe if he left the angel alone for a moment, one of the many smoking hot girls might approach him herself.

No such luck though. When Dean returned to the table, Cas was sitting quietly with his hands folded on his lap. Dean noted that he at least seemed more comfortable here than he had been in the brothel. He set the beer in front of Cas and sat down himself, taking a look around the bar. It didn't take long for his eyes to find one of the hottest girls Dean had ever seen entering the bar. She was wearing tight dark jeans, with knee-high boots and a tight black tank top. Her wavy hair was dark and long. And she was headed straight for them.

Dean shifted his eyes, not wanting to come off as a drooling freak. When she stopped at their table, he willed his eyes to meet hers, but found he couldn't since she wasn't looking at him. She was looking at Cas.

And Cas was looking up at her. He wasn't sure, but Dean thought that this might be the only time he's ever seen Cas look a woman in the eyes. Ruby and Anna, sure, but that was different. They were enemies. This woman didn't seem to be an enemy.

"You two know each other?" Dean asked, trying to break the tension. There seemed to be an unspoken conversation going on between the two. He almost felt like he was intruding just by being there. And if Dean wasn't mistaken, Cas looked a little…guilty.

One moment the two are having a staring contest, the next the woman is pulling a chair from one of the nearby tables, not bothering to turn it around, instead straddling the back of it. She leaned forward, crossing her arms over the top of the chair.

And now she was looking at Dean. He felt uncomfortable, especially seeing as she didn't seem too happy with him.

"You took him to a brothel?"

For once, Dean was speechless. He couldn't figure out who this girl was, much less why she was so angry about him taking Cas to the strip club. He glanced at Cas, hoping for some answers, maybe some back-up, but there was apparently something very interesting about his hands in that moment.

So Dean pulled out his best weapon from his arsenal. His charm.

"It was harmless fun. Just trying to get Cas here to loosen up, you know, seeing as it might be his last night on Earth."

The woman flinched, but otherwise held her composure.

"You tried to help him lose his virginity," she said in an accusatory voice.

"Yeah, well, maybe I was a little misguided."

"Misguided? Try foolish. Try dangerous." She kept her voice low, and her face didn't show much anger, but Dean could tell that beneath the surface she was fuming. She shook her head with disdain and Dean, and scoffing, she turned back to Cas.

"Castiel?" The angel's eyes raised from his hands to hers in an instant. It almost caught Dean off guard. "Can you get me a drink? Whatever you guys are having?"

Silently, Castiel nodded, seemingly back to his old self, pensive and brooding. The puppy dog look seemed to ironically disappear, even though in a way it probably should have been elevated by the strange woman's behavior.

Once Castiel was out of ear shot, the woman turned back to Dean immediately. She seemed to have her anger in check, even more so than before. "You have to be careful. Castiel has rebelled against the angels, but he hasn't rebelled against God. And for that reason, you cannot lead him into temptation."

And for Dean, that cemented what he had already vaguely been thinking. This strange woman was an angel. What kind of angel, he wasn't sure. Or maybe she was like Anna. Maybe she had fallen. Maybe she'd fallen into temptation.

"Look, lady…"

"Kaylee," she corrected him.

"Kaylee…I admit in retrospect it probably wasn't a great idea, but how was I supposed to know?"

"He's an angel!" she exclaimed, careful not to be too loud.

Dean tried to retort, but she shushed him. Dean soon found out why when Cas set a beer in front of Kaylee.

"Thank you Castiel."

"So what are you doing here anyway? And who are you?" Dean was going to get some answers, no matter what.

"I'm here because…"

Castiel cut her off. "She's here because I asked her to come. She has graciously offered to aid us, me specifically, in carrying out God's will. Especially in the defeat of Lucifer."

"So what? She's fallen or rebelled or what?"

"Rebelled," Kaylee answered. "But I've been rebelling for quite a long time. I guess my time here on Earth could equate to something of a gradual fall. I toe the line, but never cross it. Which is why, I'm sure, you can understand why I was so upset that you were willing to just push Castiel over the line."

"Look, I told you I was sorry…"

"Actually, you didn't."

"Well, I am. Anyway, if you've been rebelling for such a long time, how come you're only now offering to help?"

"Because no one wanted my help until now. And there's no way that I could have taken on all of the angels without at least a little help, or at least some leads to go on. When I heard the angels talking about you Dean, I prepared myself. I waited for my chance to jump in. I've been secretly fighting, sometimes trying to stop seals from breaking, but I have yet to have the opportunity to actually be a part of the fight. So about two weeks ago, I approached Castiel about helping. He's been hesitant, but recently he asked me to begin tracking Lucifer."

"Oh, and how has that been going?"

"It's proven to be…difficult, but that was to be expected."

"So I'm still not clear on why you're here and not out finding Lucifer."

"Castiel called me. After getting a handle on the situation, I thought it necessary to join you."

Dean squinted his eyes at Kaylee. "Well, he's fine now. So if you don't mind, mommy dearest, you can just fly your little angel ass out of here."

In response, Kaylee stood up, but before Dean could get too excited, she grabbed Castiel's arm and pulled him away to a corner of the room.

Once Kaylee felt they were far enough away, she let go of Castiel's arm. "Are you okay here?"

"Yes. I apologize for calling you. I overreacted. But I felt as if I should confess my sins to someone, and lately I'm not sure if God is still listening."

She laid her arm on his shoulder. "Castiel, you can always call me. However, it seems you have the situation under control now and Dean has now realized the error of his ways. If you trust him, I'll trust him."

"I trust him."

"Okay. Follow your instincts. If you're uncomfortable, say so. Walk away. Fly away. Do something to get out of the situation." She started to turn away, but his voice brought her focus back to him.

"I was much better at being an angel. I'm no good at living in this world."

She gave him a sympathetic smile. "You just have to get used to it. I promise it'll get easier."

"Will you help me?" At her hesitance, he eagerly went on, "I feel as if you have a unique perspective, one Dean doesn't possess. I understand that you have work to do, and so do I, but will you help me whenever possible?"

"Of course. I told you, call me anytime." She jerked her head towards Dean. "Now go have fun." As Castiel began walking back to the table, she called after him, only loud enough so he could hear, "Just don't go losing your virginity. Or sinning in any way."

He gave her a devilish, but at the same time sheepish, grin if such a thing is possible, before continuing on to rejoin Dean.