Dean had noticed the attractive woman at the end of the bar when he'd come in, and he definitely noticed how she kept looking at him. She'd turn away as soon as he looked at her, but he was sure she was watching him. Dean wasn't sure if he should be aroused or suspicious.

Purely on looks, Dean was leaning towards aroused. Good figure, dressed to show it off in tight-fitting denim and leather, with dark green hair and a few piercings in each ear. He briefly wondered if the carpet might match the drapes.

Dean sincerely hoped he didn't need to be suspicious. They'd managed to get rid of the vengeful spirit they'd been hunting (a boring, uneventful hunt, really), and Dean just wanted to relax, maybe let off a little steam, before he and Sam headed back tomorrow.

As Dean got up to play pool or go to the bathroom throughout the evening, he could feel the woman's eyes on him, but she never made any move to approach and kept feigning disinterest whenever he looked directly at her.

Dean eventually decided direct was best. He figured he'd either get lucky or get the coming fight over with on his terms. He approached the woman. She looked startled, like a deer in headlights, as he walked towards her. As Dean got closer, he could see the woman was quickly trying to rearrange her face into something resembling an amused smile. "Can I buy you a drink?" he asked her with a confident grin.

The woman actually blushed a bit. "Oh, I, ah... sure!" she stammered. "Grasshopper, please." The way she wouldn't look Dean in the eye and instead flicked her gaze around other parts of Dean's face and body was suspicious, but maybe that was down to some shyness.

Dean chuckled at the girly drink she wanted and smiled. "Sure," he said and turned to get the bartender's attention. When he'd made the order, he turned back. "So, what's your name?" he asked. Dean took a swig of his beer.

The woman looked chagrined. "Caught me looking, didn't you?" she asked, instead of answering.

"You weren't exactly subtle about it," Dean replied, amusement coloring his tone.

The woman sighed and muttered, "I thought I was," as her drink arrived. She gulped it down quickly, seeming a bit nervous. She took a deep breath, seeming to psych herself up before speaking. When she did speak, she looked off to the side and at the floor. "I don't normally do this kind of thing, but you're..." her eyes flicked back to Dean's face briefly and then down to his chest before flicking back sideways to the floor. She swallowed. "Very attractive. I'm staying at that motel nearby. You wanna come back to my room with me?" Her cheeks flooded with more color. After a pause, she added, "I have more booze."

Dean wanted to burst out laughing. This chick was really cute in her shyness. And she was pretty obviously telling the truth about not usually doing this sort of thing. "You move fast," he commented instead of replying. The woman smiled painfully and turned away, reaching for her purse as she got up. Her hand paused on the strap as Dean continued, "I didn't say I wasn't interested." She looked back up at him in surprise, them quickly looked back down, smiling. He drank down the rest of his beer and, beginning to hope this was on the up and up (against his better judgement), told her to lead the way.

She left the bar, turning right once out the door. She turned the corner of the building, and Dean followed just a few steps after her. Instead of continuing to follow the sidewalk to the motel, the woman suddenly disappeared around the corner to the back of the building. Son of a bitch, I knew I shouldn't've gotten my hopes up, Dean thought as he trotted to catch up with her. When he turned the corner, she was leaning against the brick wall, waiting for him. She stared at him, still not quite meeting his gaze and looking instead at somewhere in the vicinity of his chest, with her arms crossed under her chest. She spoke suddenly. "I know who you are, Dean."

Dean's adrenaline spiked, and he reacted instinctively. He pushed her up against the wall with one forearm across her chest and shoulders, leaning his full weight on the arm. He leaned down so his face would be right in her face, his intention to intimidate. He put a hand on his Angel Blade, just in case. "Who are you?" he growled at her. For her part, the woman made no move to defend herself, her hands tensely splayed against the wall behind her. She finally met Dean's gaze with tense eyes as, in reply to his question, the woman's eyes, irises and whites alike, turned opaque black.

Dean flicked out the Angel Blade in an instant and held the point against the woman's side where he could easily stab up behind her ribs and into her heart. She actually gasped a little as she felt the tip of the Blade. She closed her eyes and her face tensed up, clearly expecting what usually came next with Dean and demons.

But it was that expectation that made Dean pause. After a beat or two of holding her breath, the woman briefly opened one eye to look at him, then closed it again. "Just do it," she whispered.

Dean's hand involuntarily pulled the Blade away from her side in confusion. "Come again?" he asked as he let a little weight off of her.

The woman let out an explosive sigh and opened her eyes again. She looked somewhat downward as she said with thick exasperation, "You so don't live up to your reputation, Dean. I really thought you'd kill me immediately once you knew what I am."

Dean struggled to catch up. "You wanted me to kill you?" The woman nodded. "Why?"

She rolled her eyes. "Honestly, I'm surprised you don't get more of this." She raised an eyebrow and her eyes turned inward for a moment. "Or maybe that's why fatalities are so high among the henchmen," she muttered. She shook her head and looked up again, still not quite meeting Dean's eyes. "Anyway, I'd think it was pretty obvious. Being a demon sucks, so I want you to send me to The Nothing. Please."

"What the hell? No!"

"Please, Dean. You've killed so many other demons, so what if it's one who wants to die? What's one more?"

Dean sheathed his Blade and turned away, letting his arm fall to his side. "No." He began to stalk off.

"I'll follow you until you do it!" she yelled.

Dean sighed and turned back around. "Why me?"

"You have the right weapon for one, and for two you were just easier to get to. Do you think I should've asked Sam?"

Dean's eyebrows came together in consternation. "Lots of people have Angel Blades now."

The woman blinked rapidly several times. Eventually, she replied, "Oh, really? I've been out of the loop for a while now. Well, that makes things easier. Who's the worst hothead among the hunters with Angel Blades?"

It was Dean's turn to be rendered momentarily speechless. He shook his head. "Okay, just, first off, no. I'm not telling you where hunters are or who they are. Second, this feels all kinds of wrong." The woman sighed, hanging her head to the side in seeming exhaustion. "Okay, look, all I can think is you should come with me."

The woman looked back up with a wry smile. "Fine. Whatever, I guess."

A rune carved into her flesh to keep her locked into her vessel and some handcuffs later, Dean lead the demon woman back to the crappy motel he'd walked to the bar from. He put his jacket over her shoulders to hide the cuffed hands behind her back. He kept one arm around her shoulders, squeezing his hand into her shoulder to lead her. She remained silent through the walk.

Dean opened the motel room door and pushed the demon through first, calling out to Sam as he did so. When Dean entered the room, Sam was standing by his computer and began walking toward him. "What the hell, Dean?" Sam asked, throwing his arms wide in exasperation.

Dean let go of the demon's shoulder. "Got a suicidal demon here, Sammy."

Sam's eyebrows flew up to his hairline. "She attacked you? Are you okay?"

Dean shot the demon a look. "Nah, she flashed her eyes black at me and expected me to kill her."

Sam paused a beat before responding with a confused, "What?"

"Dean's such a hothead, supposedly, that I really thought he'd kill me on sight. I guess I should've tried to be more menacing," the woman supplied.

Sam was obviously struggling with the idea as much as Dean had. "You… wanted Dean to kill you?"

"Yes!" she cried in exasperation. "What's so hard to understand about this for you two? Jesus! You guys have killed, like, a thousand demons, so kill me already!"

Dean rolled his eyes. "See what I mean? Nuts!"

"Oh, it's quite logical," she said as she turned back to Dean.

"How, exactly?"

"Look, you might not believe this, but I wasn't really that bad of a person. I just didn't believe it was real when I took the deal, okay? I hate what I am, and after the last several years on the run, I just want this to end." After her speech, she suddenly sat down on the floor, hard. She hung her head and spoke to the floor. "Please," she said in a small, broken voice.

Dean and Sam looked at each other, unsure of what to do.

Dean was still suspicious of her. "If you're 'not that bad,' then whose meat suit you wearin'?"

The woman continued to speak to the floor. "Real sad. She OD'd on heroin. I jumped in after her soul was out. Just another vagrant gone missing from her corner."

Dean snorted a bit. "Bull. Shit."

She shrugged. "Believe what you want. I didn't get her memories, so I don't know much about her, other than her name was Christie and her pimp was a weak schmuck who went by T-Bone. That's how I got my startup cash; I beat him up, took his cash, and dropped him off at the hospital. Honestly, I don't feel bad about that one."

Sam and Dean shared another look. It was becoming increasingly difficult for either of them to believe this was an act.

Dean ran his hand through his hair. "Look, I dunno what to do, so…." He threw another look at Sam, who nodded. "We're gonna have you sit tight for a bit."

Dean undid the cuffs and ushered the woman to a chair. Sam tossed him some rope, and Dean tied the woman to the chair. Afterward, he pulled out a phone and tapped it a few times. He put it to his ear and began talking as he left the room. "Cas? Where are you?" Any other words were lost as Dean closed the door behind him.

Sam, meanwhile, sat back down at his laptop.

The woman sat in silence until Sam finally broke it. "What's your name?" he asked.

"Iris."

"Okay, Iris, where did you beat up the pimp?"

"Detroit."

Sam continued working at the computer, occasionally asking Iris a question, until Dean came back inside. "Cas will be here in a few hours."

Sam grunted in response. He continued working at the computer while Dean lied down on one of the beds. At first he tapped at his phone for a bit, but he eventually returned the phone to his pocket and closed his eyes. When there was a knock at the door a few hours later, Dean got up immediately and was the one to open the door. "Hey, Cas," he greeted as the angel entered the motel room.

"Hello, Dean," he replied.

"Hold up, you've got a goddamn Angel on speed dial?" Iris exclaimed. Her face was draining of color.

Dean gestured to Iris. "Well?"

Castiel crossed the room and crouched in front of the chair. He closed his eyes and touched two fingers to the demon woman's forehead. Iris's eyes rolled up into her head and began to glow white. Tears streamed down her face. Her fingers gripped the arms of the chair and her feet strained against the restraint of the rope. She began to pant, and she soon screamed, "Stop! Stop! It hurts!" Castiel opened his eyes and took his fingers away from the woman's forehead just as she began to let out a painful wail. She immediately slumped forward, hanging her head and panting.

"Jesus, Cas, what did you do to her?" Dean asked.

"I was looking into her vessel, as you asked. Any contact with my essence is incredibly painful for a demon. As far as I can tell from my search, she is telling the truth about possessing a vessel whose soul had already left." Castiel turned to talk directly to the demon. "How is it that I could only see your true face and how damaged your soul was by looking inside?" he asked.

Sam and Dean turned quickly to look questioningly between the angel and the demon at that. Iris just panted for several seconds before answering. "A spell," she eventually managed. "I'd be caught and sent back to Hell pretty quickly without it, don't you think?" Her voice was still pretty breathy.

"Seriously? That's… that's possible?" Sam asked incredulously.

Castiel turned to Sam. "Evidently. When I first walked in, I could have almost mistaken her for a human. But delve into her mind, and it becomes clear very quickly what she is. I must say, though, she is surprisingly sane and her soul surprisingly intact for demon, even after seeing what truly lies beneath the spell."

"Sane? She wants us to kill her!" Dean exclaimed.

"Given her other options, maybe that is the most sane choice, Dean," the angel replied in his usual intense gravel.

Sam suddenly turned and sat back down at his computer. "Check this out, guys," he said, ushering them over. "Everything she told me checks out. I found a woman named Christie Madsen in Detroit who had a string of drug arrests until several years ago. Also found a police report of a Timothy 'T-Bone' Miller being dropped off in front of the emergency room in critical condition, and his car turning up abandoned just outside of town. I even found the obituary and the report of the 'animal attack' of one Iris Leahy. I think she's telling the truth."

At the end of Sam's report, there was a brief silence as the three men shared a look. It was broken by Iris's voice. She had sat back up, but now her head was flopped onto the back of the chair and she had her eyes closed. "Hey, that's great and all, but what does it matter? Couldn't you just kill me either way?"

"There's… there might be another option," Sam said slowly, turning from the computer and looking at the woman. Dean threw Sam a look that clearly asked if Sam knew what he was doing.

Iris didn't move or open her eyes. "What?" she asked in a flat tone.

Sam got up and stood in front of the chair, looking down on the demon tied to it. "We could redeem your soul," Sam said slowly.

Iris let out a bitter laugh and opened her eyes but didn't lift her head. "Good one. Very funny."

"It's true," Dean said. Iris's eyes darted over to him. "I was a demon for a little while, and that's what brought me back."

The woman narrowed her eyes in suspicion. "What does that even mean?"

Iris's head came back up when Castiel spoke. "It is a long story, but it means that you could be human again. More, it means that your soul could go to Heaven next time you die."

"Impossible," Iris said flatly.

Sam tapped her hand to get her to look at him. He crouched down to look her in the eyes. "We're telling you it's not only possible but that we've done it before," he said in an earnest, even eager, voice. "What have you got to lose by letting us try?"

Iris sighed. "Not much, and I guess I don't have a choice now, as your captive," Iris paused briefly as Dean snorted, "but, I mean… People are dicks, you know? How do you know I'll be a human that was worth the trouble of redeeming?"

"Either way, humans are easier to kill," Dean rumbled. Sam frowned and shot Dean a look. "What? It's true!"

Note: What do you guys think of this premise? Interesting enough to continue?