Title: The Dilemma of Human Investment
Chapter: One
Summary: Disgusted with Dean's inability to pay attention, Castiel takes an unorthodox action that has unforeseen consequences for him and Dean both. Sam then overhears a conversation between Castiel and Dean and gets the wrong idea about what transpired.
Rating: M - because I don't feel comfy with it at a 'T'.
Disclaimer: 'Supernatural' was created by Eric Kripke. No disrespect is intended.
Notes: This started out as a comedy and morphed halfway into something entirely different.


"Dean."

Dean wasn't listening. Castiel tried again, this time with more insistence.

"Dean."

Suppressing a sigh, he turned his own attention to where Dean's had strayed. Predictably, it was a woman who'd caught his attention. She was physically pretty, he supposed, with dark hair and an exotic air about her.

Since leaving Lisa, Dean had been throwing himself at any willing female of consenting age. It was a willful return to how he'd once been, as though behaving in such a manner negated the emotional changes inside him. He wanted to forget all desire he had for what he'd called the 'normal' life.

Sam looked up from the pages he was studying. "She's not your type," he pronounced in an amused tone.

"Are you kidding, Sam? Of course she's my type. I could get into the whole naughty librarian thing."

"Naughty librarian," Castiel asked, brows raising.

"Yeah." Dean's voice was wistful. "Innocent and prim looking on the outside, yet with a hint of red hot babe. See, you can tell by looking at her."

He frowned, returning his attention to her. "How?"

"You see how her blouse is unbuttoned right to her cleavage? The really prim miss would have that thing closed to the neck. And her skirt? Mid-thigh isn't innocent. I bet she saunters when she walks, really works those hips, taking deliberately slow strides in those three inch heels she's got on."

"He's been watching too much porn again," Sam explained. "Which one was it this time, Dean? 'Hot, Sexy Librarian Babes Ten' or 'Schoolteachers Get Wild'? I noticed both were on yesterday."

He shook a finger at them. "You laugh, but watch when she leaves. Blouse, skirt, heels, walk. She may tell herself she dresses for herself, but deep down, she knows that every guy in this place is watching her," he jerked a thumb at Castiel, "even Cas. Even the gay guys, because they're thinking, that girl knows how to dress."

She gathered her belongings, which appeared to be mostly stacks of paper, and left her table. Dean was right, Cas saw. She sauntered slowly past them, her heels clacking on the floor. Dean turned to ogle her from behind.

Castiel tilted his head back as she passed, doing a tour of her mind, and then a blithe tour of Dean's that would freak Dean out fairly completely if he'd known. What he found in Dean's mind made him smile a little in sudden understanding. "You know her?"

Dean let out a sigh and shook his head. "Not in this life."

Her name was Risa Hope and Dean, until now, had thought Zachariah had made her up. That was interesting to Castiel, as the lovely Risa was an angelic vessel who'd never been filled. He wondered why and flicked his gaze back to the door. She paused at it, glancing behind her with the hint of a knowing smile. She'd known they were looking at her and didn't mind in the least. She was used to that sort of attention. The door closed behind her. Castiel could see her through the glass, getting into a car in the lot. Of course Zachariah would have had access to the names and locations of unfilled vessels. It made sense that he'd show Dean one that Dean would be attracted to.

He blinked.

Dean was attracted to Risa.

Perhaps Dean needed an object lesson on appearances.

A vague plan forming to teach Dean that lesson, Castiel followed her.


Even now, Dean couldn't believe how wrong he'd been about Lisa.

He should have realized something was up with her. What sane woman lets a guy she barely knows into her house to live with her and her kid like that? She'd taken him into her house, her life, her bed immediately, and all without anything save a hug and some murmured gentle words on how she'd take care of him.

Prophetic words if ever he'd heard any. Take care of him. Those four words now gave him the willies.

It should have been obvious something wasn't quite right from the moment she'd admitted she thought no man compared to him.

While nice to hear, her dreamy, adoring tone at the time had set off warning bells in his head. Careful questioning as the days had slid into weeks had revealed that she wasn't just slightly nuts, she was 'number one fan, Misery' type nuts, but in a weird way.

She'd ask him to throw a ball around with Ben, but when he tried to give Ben pointers, she exploded, telling him he wasn't Ben's coach and had no business saying anything. She'd asked him to help with homework while she made dinner, yet when he corrected something he knew was wrong, she'd again exploded. There'd been little things like that peppering day-to-day activities, things he hadn't paid much attention to at first. She had this thing about being a mom and being the only authority in Ben's life and he didn't really argue with it. She was Ben's mom, after all. She'd raised him by herself, so of course she was used to being the only one in charge.

It seemed normal. Nice and normal.

His grief for Sam had hit him harder than hard and it hadn't occurred to him something was wrong with the life he was living with Lisa for an embarrassingly long awhile.

At first, her mothering had seemed a normal thing, a natural way to comfort him. She'd let him watch tv with his head in her lap, her fingers touching his forehead, temples and hair in soft, soothing sweeps. She'd rub his shoulders and back and insist he let her 'take care of him'. She made pies on the weekends, carefully doling out portions so one pie lasted the whole week - which he thought was insane to begin with. Who could resist a fresh apple pie? Or cherry, peach, mixed berry…. Especially with ice cream? He could eat an entire one by himself. He was a grown man and she insisted he follow her rule about desserts and sweets: a single portion a day only.

Yet she served frozen pizza regularly and various other foods he knew very well weren't really good for a person. He'd easily gotten around her rule, until she'd found a half-eaten candy bar in his jacket pocket. What she'd been doing going through his pockets was one issue. She'd busted him on the other, insisting he was setting a bad example for Ben. By that point, he hadn't bothered pointing out she wasn't letting him be any example at all anyway, so what did it matter?

He'd come to realize that she liked mothering a little too much. She was possessive in it, possessive of Ben and, at the same time, possessive of him. She'd told him over and over that he'd been the best night of her life, but then she'd dropped the bomb: she told him she'd waited for him to come back to her because they were fated to be together. She'd known that eventually, he'd be back to stay.

Now, Dean knew a little bit about fate and free will, and since he'd beaten the angels at what they considered fate, he knew damn well he had a choice in the matter.

What kind of woman sits back and waits for a man she had a wild night with to find her again? And again. And…again. Not only waits, but doesn't even date? For a whole decade? Ben had told him that, telling him that, "Mom's never had a boyfriend. She only goes out to work and school things. Sometimes things with her friends."

Never had a boyfriend. What kind of woman obsesses on a guy like she'd apparently done with him?

That thought had occupied him pretty much 24-7 after that little revelation. Dean didn't mind the wild, freaky women, but this? Had she always been like that? He'd thought she was normal. She'd certainly seemed normal until he'd started living with her.

He didn't mind how she paraded him around to her friends, yet heaven help the woman he smiled at. Or the one he was nice to. Or the one he even talked to. He'd heard her accuse one woman of trying to steal him from her.

Sure, she'd apologized to him when he'd talked to her about it, done the old 'I'm just so glad you're here and you stayed' bit, claiming that she couldn't bear the thought of him leaving again. Maybe she was a little bit insecure, she'd admitted.

Talk about emotional blackmail.

Lisa, it turned out, was a master at it and at manipulation, which floored him because…well, she'd seemed so normal.

How could he have been so wrong about her? Usually, he was right on the money with women. Okay, occasionally, he'd read a woman wrong, but Lisa? She just hadn't seemed the nutso type. She'd seemed…normal. He kept going back to that word, but it was true. It's what he'd thought she was.

She hadn't taken kindly to Sam showing up, either. Never mind his own issues with that, her reaction had convinced Dean it was time to leave Dodge - even more than Sam's insistence he go. While he'd hated to leave Ben there, what could he do? Lisa was his mom, not some shape shifter or demon - he'd checked for those and for any other creature he could think of.

He and Sam had driven off with her throwing things at the car with a surprisingly good aim. They'd parked awhile later and sat staring at the windshield.

Sam had cleared his throat, shaking his head. "Dude…I'm sorry. I really thought she was normal."

"You and me both," he'd replied and for some reason they'd both started laughing, sitting there side by side in the Impala, laughing until they cried and had had one of those reunions that belonged on Oprah.

Dean looked at Sam now, then at where Castiel had been a few seconds earlier. Try as he might, he had yet to be able to actually teach Cas to say 'goodbye' before he left.


"Don't be afraid," Castiel said, though this wasn't the first time Risa had seen an angel. He gleaned the details of that meeting within seconds of appearing, his disgust for Zachariah growing.

It had been Zachariah who'd come to see Risa. He'd wanted to recruit her to his cause, use her to get at Dean. He'd wanted her to seduce Dean Winchester and lie to him - tell him she'd been the vessel of an archangel when all she really was was a regular grade vessel. He'd given her a name, tried to tell her there were more than four archangels. He'd lied to her.

Zachariah had told her to convince Dean he wouldn't be left a drooling mess. She was to get in close, make a connection with him and make herself important to him, following Zachariah's every instruction.

Despite her fear of him, Risa had refused, citing scriptures that said lying was wrong. She knew her Bible well. Proverbs 6:16-19 had particularly incensed Zachariah and he'd hurt her and healed her over and over in an attempt to change her mind, using torture when he couldn't coerce the action he wanted from her. Risa had a strong will. She'd held firm, the only thing saving her being the joyous cry of another angel that said Dean Winchester had been found in Kansas City, Missouri. Otherwise, Castiel was sure Zachariah would have killed her for her refusal.

He'd removed the memory of what he'd done to her, but left her with the knowledge that she'd met an angel and it was both awesome and terrifying. Then, he'd taken her image and used it in an attempt to sway Dean to accept Michael.

"You're an angel," she asked, staring at him with fearful eyes.

"I'm Castiel. I've not come to harm you, Risa."

"What do you want with me?"

He studied her, trying to gauge what her reaction might be to his request before he said it. "You're special, Risa. You're one of few in this world whose bloodline enables them to be vessels for angels, conduits to allow us to communicate with humanity."

"I know. The other angel…he told me."

"I've come to ask you to be my temporary vessel. It would be a week only, perhaps two."

"You have a vessel," she pointed out. "Why do you need another?" She ducked her head. "I shouldn't question -"

"Of course you should," he said a little sharper than he'd intended. "You have a choice in it. I won't coerce you. You either agree or you don't. If you don't, I'll leave you alone once more. If you do, I'll take you as a temporary vessel." He wasn't even really sure it'd work. After all, she wasn't related to Jimmy in any way and they'd always been told that each angel had only one bloodline to use as vessels. It had never made sense to him for it to be that way. It made much more sense that any angel could use any vessel available.

"I don't know." She shrugged. It was an honest answer. She was torn. While Zachariah had removed her memories, he'd left a fear of angels in their place. She wanted to be of use, but it scared her.

"I don't require you for anything dangerous, merely for a brief lesson to a man on appearances. You'll be returned here in the same state you leave it. You won't be harmed, Risa. I promise."

She thought for two days, then gave her consent.

He stepped forward, hand raising to touch her face. He transferred himself into her and in seconds, was steadying Jimmy as he staggered.

"Castiel? What's going on?"

"I've made arrangements for you to spend a week or two with Amelia and Claire."

Suspicion flickered in Jimmy's eyes. "Why?"

"You don't want this gift?"

"Not what I said." Jimmy's gaze slipped down her and back up. "You're going to be her for awhile?"

"You say that like it's unfathomable."

His brows rose. "Can you even walk in those shoes?"

Castiel looked down at herself. Risa was wearing the shoes she'd had on in the restaurant, the ones Dean had said were three inch heels. "Why wouldn't I be able to?"

Jimmy laughed and stepped back. "You might want to try it."

In three steps, Castiel found herself on the floor, listening to Jimmy's snickering. Walking in high heels wasn't as easy as she'd thought it would be. "I'm guessing there's some trick to this?"

"Not just to that. There's a trick to fastening bras, too."

Standing back up, Castiel frowned at him, then unbuttoned Risa's blouse and removed it. She touched the lace cups of the bra. "It appears to be a standard undergarment." After a moment of struggling with the clasp behind her, she took it off and held it up, studying it, endeavoring to see what 'trick' there was to it. "I see nothing strange about it."

Jimmy made a strangled noise. "Not exactly what I had in mind, Castiel." He looked away, muttering, "I'm a married man," over and over.

"I should put it back on?"

"It'd be a good idea."

That, she discovered, was where the trick was. "I can't fasten it."

"Turn it around, fasten it in front, and slide it in place."

"Oh." Dressed once more, Castiel looked at Jimmy closely. He was perspiring and flushed. "Are you ill?"

"A beautiful woman took her top off in front of me. I'm not ill. I'm a perfectly normal man with a perfectly normal reaction who'd really like to see his wife now, if that's actually going to happen."

"I made you uncomfortable. I apologize." Castiel took Risa's shoes off, then made sure Jimmy was safely with Amelia and Claire before going back to Risa's house. She took another day in an attempt to become used to Risa's body before heading out to see Dean.


Luck was on Dean's side. He was glad something was finally working out for him. Risa had turned up in a bar four days after he, Sam, and Cas had seen her in that restaurant. He let his glance drift down her and back up. She was looking as fine as she had that day. Even finer actually. Her skirt was shorter, displaying her legs to terrific advantage, and whatever bra she had on was pushing her breasts up in a way that made him want to sink his face into her cleavage and stay there until he suffocated.

He took a deep breath. Her perfume was a sensual mix of musk, spice, and flowers and all he really wanted was to take her back to his room and see how fast he could make her scream his name in ecstasy. He opened his mouth to ask her if she'd like to leave with him.

She looked at him out of the corner of her eye. "Yes."

"Excuse me?"

"You were about to ask if I'd like to return to your room with you. The answer is yes, I would."

He studied her a moment. For someone who'd seemed initially clueless to the fact that he'd been hitting on her, she'd sure caught on fast. Had to be an act, he decided as she slipped from the barstool to stand and face him, completely ignoring the rules of personal space to a degree that was excitingly seductive.

"Am I standing too close," she asked, in an innocent tone that caused that ripple of need inside him to deepen, looking up at him with an expectant gaze.

"Not at all. The closer the better, sweetheart, if you catch my meaning." He winked at her.

"I believe I do 'catch your meaning'." She pressed closer with a small, satisfied smile. "I've no further wish for alcohol at present. We can leave when you desire to."

He did desire, taking one last swallow of his beer before motioning towards the door. "Ladies first."

"Thank you."

Risa carried her coat and purse in one arm, hips swaying. She walked slowly and Dean had the odd thought that she didn't look nearly as graceful in those high heels as she had a couple days earlier when she'd left that restaurant. Probably the beers, he decided. She was a little unsteady from the alcohol and those were three inch heels she had on.

Once in the room, she set her coat and purse down on the table, turning to face him. There was an odd look in her eyes, longing mixed with fear and something else he couldn't quite identify. The way she looked at him…. It was almost like she already knew him somehow.

He put the chain on the door and walked over to her.


Dean was behaving in an entirely predictable manner. Castiel decided it was probably a good thing she'd taken a male vessel initially to interact with Dean. A female one would have distracted him.

Cas let Dean buy her drinks, making sure to let her skirt remain high on her thighs instead of tugging it back in place. Dean remained close, using conversation to put her at ease and making teasing remarks designed to entice her back to his room. Pick-up lines, Sam had called them. Cas drank beer after beer and observed Dean's behavior, trying to imitate the flirtatious manner of the various women she'd seen over the past months.

It was harder than it had looked, though a sidelong amused glance seemed to go far with Dean, encouraging him bend his head to hers so their conversation was a bit more private. She caught a whiff of his aftershave. Had it always smelled so good? His arm brushed hers and she shivered.

"You cold," he asked, arm against hers again, producing the same response.

Castiel thought about it. Was she cold? No. The shiver was a sort of odd reaction to that brush of their bare arms. She licked her lips and shook her head. "Not really."

As the evening went on, Castiel began to realize that Dean's rules were quite different for women. Take the personal space one, for example. When Cas had stood close in Jimmy's body, Dean pitched a fit and gave him a lecture. While in Risa, Dean seemed to wish her to move even closer. It was confusing and contradictory.

Dean's body was warm. It even felt natural to move a bit closer, so she did, her breasts pressing to his chest. The pleased gleam in Dean's eyes deepened and her mouth seemed suddenly quite dry.

It occurred to Castiel that Dean might be upset when she revealed herself, but that thought disappeared as she concentrated on not toppling over while walking. High heels were a trial and she still wasn't walking very well in them despite practicing.

She let Dean take her back to that room he was sharing with Sam, not missing Dean's thumbs-up gesture to Sam or Sam's weary sigh that indicated he thought he was going to have to spend the night in the Impala - again. Castiel wondered if she should reassure Sam that wasn't going to happen. Dean steadied her with a gentle hand on her arm and then he put an arm around her, guiding her to the motel.

Inside the room, Cas set down the coat and purse.

Now is the moment to reveal myself, Castiel thought. She'd proved her point about appearances and with a word, she could open Dean's eyes to that.

She let the moment slip by, however.

It was a choice that even a few months ago she wouldn't have made. Being in Risa's body and looking at Dean was like seeing him for the first time.

Castiel hadn't anticipated that.

She'd recognized previously that he was a beautiful human, yet now that beauty seemed pronounced, so much more than the spiritual beauty of a good man. This beauty was also physical, sensual, his features having a pleasing symmetry, his body also pleasing.

No, more than pleasing. Castiel searched for the right word and could only find one to describe him: desirable. She wanted to stretch out her hands, run her fingertips along his skin, feel the play of muscles beneath that skin, then press her mouth where her fingers had been and taste him with her tongue.

The urge to do that was nearly overpowering. She couldn't control it and wasn't entirely sure she wanted to.

Risa's body was subject to both emotional surges and odd physical responses. Cas couldn't recall ever having some of these troubles in Jimmy's body.

Like her heartbeat quickening while looking at Dean. Or that urge to lean over and sniff Dean because he just smelled so good. Or run her hand along his chest, which looked wider than it had before. She wanted to experience more with him and experience those things he'd once taken her (in Jimmy's body) to a brothel to try. She wanted that with him.

The urges were…distracting. Perhaps this was why they mostly used male vessels?

She opened her mouth to speak and had no idea what to say.


She was watching him in a way that reminded him, of all things, like the way Castiel looked at him. A concentrated stare, like she was trying to figure something out. It was forward and sexy as hell, especially when her head tilted, her hair slipping down half across her eyes and her lips parting.

Dean stepped close and kissed her. He expected her to pull away, but she didn't. Instead, she was still against him, as though he'd managed to surprise her and she didn't know what to do. When he drew back a fraction and opened his eyes, he found her eyes open, still staring, still watching. He brushed her bangs aside with his fingers, traced the contour of her cheekbones, and cupped her jaw with both hands. "Close your eyes."

"But then I can't see you," she breathed in that low throaty voice that had been giving him shivers since he'd first heard it in person. Zachariah's version of her had had a higher voice. In fact, ole Zach's version of Risa seemed to be mostly fabrication, not at all the sort of woman Dean had discovered her to be.

He couldn't decide if she really was inexperienced or just very good at the whole innocent, nervous virgin act. He couldn't wait to learn which it was. "Trust me."

"I do trust you, Dean," she said with a certainty that surprised him. Risa closed her eyes.

Leaning forward, he pressed his lips to hers, caressing as lightly as possible before deepening the kiss. Her hesitation was exciting. Far from dampening his ardor, it made him want to pursue her all the more and he pulled her to him. She was tense against him at first, slowly responding.

When he released her, Risa stepped back, one hand touching her mouth before she unbuttoned her blouse. Not one to let a lady be uncomfortable in the bedroom, he removed his own shirt and tossed it aside. He caught her to him again before she'd let the fabric of her blouse fall, holding her so that her wrists were still covered, held at her sides. She made a noise of protest, then relaxed, her kisses becoming bolder.

Dean tugged the blouse the rest of the way from her, exploring her with first a soft touch, then a firmer one. Her hands slid up his sides and around to his back, a shudder working through her. He nibbled a line along her neck, easing his own hands to the fastening of her skirt. He'd just undone the zipper when she pulled back again, holding the skirt in place.

"There's something you should know, Dean."

"What's that?"

"I've never done this before," she told him in a calm tone, letting her skirt drop to the floor and stepping from the puddle of fabric. Her panties, what little there were of them, matched the bra she had on.

"Never?" It didn't seem possible to him. Were all the men she'd ever met stupid? Blind? Both?

"Never," she confirmed.

"I see." Turning, Dean mouthed 'thank you' towards the ceiling before he reached to pull back the covers on the bed. "Well, Risa, you can back out any time. You know that, right?" Covers turned down out of the way, he turned back around.

She nodded, pressed her hands to the lacy cups of her bra. "Do I…remove this? Or do you?"

Dean sat on the side of the bed and reached out his hands, grasping her hips and pulling her close. "I'll do that for you, sweetheart." He pressed a series of lingering kisses upward from her bellybutton. "You just let me do the work."

She placed her hands on his bare shoulders. "Okay."

There was nothing about her to indicate she was a virgin save her frank declaration and overall manner. Dean found it difficult to believe that a knock-out like her hadn't had any action ever, but as physical matters progressed to a wholly satisfying conclusion on his part, he had to admit he could be wrong. Her movements were awkward from beginning to end.

Dean pressed his cheek to Risa's, drawing in a deep breath and relaxing against her. He felt wrung out, with barely the strength to move from her.

Even now, her hands were tentative along his back, almost as though she was afraid to touch him. Strange. He rolled from her, took care of the condom and laid back down beside her, drawing her against him. Dean ran his hand along her back, caressing that silky skin and already imaging what he was going to do with her the next time. She looked at him, hand raising to touch his face. He started to raise his own to capture it and hold it, but sleep was suddenly upon him and Dean lost consciousness.


While she'd seen Dean in varying states of undress before, seeing him naked while being naked herself sparked more nervous trembling inside of her. She was hot, cold, sweating, shivering and a mass of confusing desires. Dean's mouth and hands trailing across her skin produced more sensations than she knew how to deal with.

I should stop this, Castiel thought as Dean reached for the package on the nightstand and opened one colorfully wrapped square of plastic. He knelt between her spread legs. I should stop this. I know I should.

But what Castiel should do and did do were sometimes very different things.

She took a long, shaking breath.

There was a deep craving in her to finish this and she raised up onto her forearms, then pushed further to sit, bringing her face very close to his. Dean turned his head a fraction, mouth on hers, tongue darting hot and quick against hers. Cas responded, letting Dean slowly lay her back, his body covering hers.

She felt self-conscious, uncertain, hands lightly resting on Dean's sides, against those ribs on which she'd placed protective symbols while in Jimmy Novak's body.

Dean's mouth left hers, the heat in his eyes mesmerizing. Castiel didn't want to look away and didn't, staring right back at him. Dean rested on his left forearm, his right hand sweeping down to her left thigh and urging her to raise it. She did. His head lowered then, cheek pressing to hers, breath hot on her neck. He shifted against her and Cas gasped.

Being joined together this way wasn't what she'd thought it'd be. It was…beautiful.

Strange. She'd never thought of sex as beautiful before. It had never looked particularly such on the screen of the television. She closed her eyes, turning her face into the curve between Dean's neck and shoulder, smelling that pleasant scent of his aftershave. He moved inside of her with long, slow, rhythmic thrusts that seemed to make those confusing physical sensations she was having increase ten-fold.

She slid her hands to his back, uncertain if continuing to touch him was allowed. He didn't protest it. His skin was hot, damp with sweat, his breaths almost panting.

Dean cried out, a sound halfway like an agonized groan, his voice a harsh rasping in her ear, as he shuddered against her and was still.

Castiel had a sense of disappointment when he moved from her and his weight no longer pressed her into the mattress. She'd wanted that intimacy to last and felt…unfulfilled, like maybe she'd somehow missed something in this experience. What could that something be? Was it supposed to be like those movies Dean enjoyed? Or were those movies pure fiction?

Dean gathered her against him, her head on his chest. Castiel raised her hand and touched two fingers to his forehead, rendering him instantly unconscious. She loosed herself and rolled away so that their bodies didn't touch.

What have I done? Cas stared up at the dark ceiling, her thoughts tangled circles, a web of contradictions. Every time Dean stirred, she pushed him back down into sleep. He'd wake well-rested at least.

Even lying naked with him, Castiel couldn't believe she'd allowed it to happen. She'd been intimate with Dean, a thing never considered before stepping into a female body. She'd allowed it, encouraged it even. Was it the body that caused the action? Had to be. She'd never wanted this in Jimmy's body, only while in Risa's, so therefore, it had to be the body.

Over and over, she continued her ruminations, going over the same ground until, at dawn, she dressed and fled the room.