A/N: This is the last chapter of Part 1 of this story. I have to take this opportunity to thank all of you who have made this so much fun for me. That's all of you who read, alerted, favorited, and especially reviewed. You reviewers have been the kindest one could hope for and I really appreciated the ongoing encouragement you gave me and your interest in my story.

I will start part 2 fairly soon – I'll be taking a small break to do some fic-reading as fic-writing takes up a lot of time and I miss reading. Hopefully you will all tune back in for that part as it starts up a couple of months after this one leaves off. It will be shorter than this one but Sam and Tash will be trying to find a way to get Dean out of Hell. Part 3 takes place when Dean returns.

CHAPTER 14

"What do you mean go our separate ways?" Tasha's jaw dropped and a stunned expression came over her face.

"What I mean is we've had fun but we both knew this wasn't forever," Dean explained, the calm of his voice not betraying even a hint of the gut wrenching turmoil that was going on inside him.

"What?" Now it was confusion and disbelief.

He swallowed and continued. "It's just that Sam and I are used to being by ourselves," he stammered, not sure what else to say, what other excuse to give, what other lie to tell.

Tasha gave him a long, hard stare, her expression making it clear his words hadn't fully registered yet and she was still trying to figure out what was going on.

"Tell me this isn't because of what happened in the car," she said finally. "Because I just gave you a look, you told me to go ahead. You said you wanted me to." There was a definite defensive tone to her voice.

"No," Dean replied quickly. "No, it's not that at all." A thought suddenly occurred to him that maybe he should use that as an excuse but he decided that would likely make her feel cheap and that was something he couldn't bear.

Not that the fear and unmistakable hurt that was now creeping into her face was even remotely bearable.

"It's coz you're scared, isn't it?" she accused. "Listen, this is all new to me too but you don't see me bailing."

"I'm not scared." Dean was almost convincing.

"Bullshit. You're scared because you feel the same way I do and you don't know what to do about it. And you're scared because I could have been killed tonight and you didn't like how worried you got. You think it's easier to not care about someone than to have to worry about losing them."

The hunter was at a loss for words. She wasn't making this easy on him. He couldn't deny she was right about him being scared by what had blossomed between them, how deep and powerful it had quickly become, but he hadn't allowed that fear to come between them before. The want and need to be around her had been overwhelming, far more so than the fear of opening his heart to her. Of course, that was also the reason he was having this conversation thee weeks before he was going to die instead of two months ago when he should have had it.

Tasha took his silence as an invitation to continue her argument, which was clearly growing more desperate as Dean wasn't backing down and she was realizing he was deadly serious about breaking it off.

"Dean, I've lost everybody. Everybody." She took a step towards him from where she was standing at the foot of the bed they had slept on last night but he maintained his distance by taking an involuntary step backwards. Her breath hitched when she noticed his move and she stopped. "But I'm willing to take that chance and live with the risk of going through it again," she finished from where she stood.

Dean bit his lip. With him, it wasn't a chance, it was a certainty.

"Your life isn't exactly safe," she continued. "But being with you is worth the risk of losing you," she tapped two fingers on her heart to indicate what she was risking.

That action, however, just further convinced Dean that he was making the right move. He was going to die. There wasn't just a risk of him dying; there was practically no chance of him surviving.

"Tash, I'm sorry," he managed. "Sam and I just need to deal with some things and we can't do that with you tagging along." It was a lame excuse, he knew, but it was all he could come up with.

"Don't blame Sam!" she retorted heatedly. "This is all you. And whatever your big secret is, you can tell me. You don't have to worry about me repeating it because shit Dean, I don't have anyone to tell."

A renewed wave of guilt spread through him, weaving its way between the devastation and the sense of loss. Again his throat constricted with unexpressed emotion and he couldn't respond right away. She took advantage of his inability to speak and kept arguing her case.

"And if you think I'll judge you or get scared off, I already told you that won't happen," she continued. "No matter what it is."

Dean realized she wasn't going to just accept his decision and let him go. Not that he could blame her; he didn't want to let what they had go either but he had the advantage of knowing it was going to end one way or another no matter what he did.

"Look," he said, steeling his heart against what was to come. "I had fun but I'm just ready to move on. I like you but…I don't love you. It's just not gonna work."

He would have had to have been blind to have missed the hurt that washed over her face at the cold words. She was agonizingly quiet for a long moment, tears welling in her lower lids. She never took her eyes off his face and he could see the barely perceptible flutter of oncoming sobs quivering in her cheeks. She finally swallowed hard and spoke, but her voice cracked as the words came out in little more than a whisper.

"Dean don't do this," she pleaded, the first single tear that slid down her cheek opening the floodgate for the stream that followed.

"Tash, I'm sorry," he rasped, taking an instinctive step towards her but stopping himself short. He struggled to rein himself in and balled his hand into a fist at his side to keep it from reaching back out towards her.

He could see her shoulders and posture stiffening as she drew on her inner reserves of strength. She wiped the wet streak on her cheeks roughly with the back of her hand. "Fine," she said tensely.

Dean's heart twisted in a sickening knot at her acceptance. Even though it was what he had been aiming for, it was a bittersweet victory. "You can have the room," he offered. "Sam and I'll leave right away."

"No," Tasha contested. "I'll leave. Just give me a few minutes to get my stuff."

Her voice was painfully close to breaking again so Dean decided to get out while he was ahead. He nodded and headed for the door. Halfway out he paused, turning around as he stood on the threshold. "Don't worry," he assured her, "We'll still keep searching for Diego."

"At this point Dean, I really don't care if Diego finds me or not."

Dean sighed, wishing the pain in his chest would go away. "Tasha I…"

"Just go."

He bit back the rest of his sentence and gave her one last look, studying her every feature in an attempt to burn the image into his memory forever. Then he turned away and closed the door behind him with a soft click.

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Sam was perched on the hood of the Impala just outside the motel room door when Dean emerged. He heard his brother's promise to find Diego but couldn't make out the muffled reply from the girl inside. Dean closed the door and caught Sam's eye when he turned around. Sam's heart skipped a beat at the sight, the depths of anguish and loss on his brother's face matching those from the days after their father had died.

Dean looked down quickly, taking a few steps forward to stand in front of Sam. "It's done," he said quietly, his jaw set tight and his voice raspy with restrained emotion. "I'm gonna go get her a car," he told the taller hunter before turning swiftly away.

He only got a few steps along the motel porch when he stopped and turned back to Sam. "Make sure she's okay?" he said, phrasing it in the form of a question. Sam nodded in silent assurance and watched his brother walk stiffly towards the swanky subdivision up the street.

Sam didn't know what to expect when he opened the door. Part of him thought he would find her throwing things and fuming in a tirade of scorned rage but the majority of him expected exactly what he did find. Tasha, sitting on the floor with her back to the wall, her arms curled around her bent knees and her head down, heaving sobs wracking her body.

He was fairly certain she didn't even noticed him come in for she never looked up or stopped crying. He only hesitated for the briefest of instants before moving over to her side in large strides and sliding his back down the wall until he was sitting in the floor next to her.

She looked up briefly, her eyes bleary and her face streaked with free-running tears. Sam's stomach turned with grief and pity at what both she and his brother were going through and a wave of anger hit him at the injustice of it all. They loved each other, they deserved each other, and yet here he was, watching them tear themselves and each other to pieces because fate had other plans for them both. Plans that apparently didn't include happiness or peace.

Sam could see the disappointment reflected in her eyes when she realized it was him sitting next to her and not Dean returning to say he'd made a mistake. She didn't say anything, however, and simply put her head back down on her knees and continued crying. He swallowed hard, trying to keep tears from welling up in his own eyelids and fought the urge to put his arm around her.

Not yet, he thought. Let her get it out first. She knew he was there if she needed him.

After what seemed like an interminably long time, the heavy sobbing lessened and the shuddering in her shoulders quelled. Although she still never looked up, she leaned slightly towards him, her arm and her knee resting against his much larger frame. He took that as his cue and lifted an arm up and around her shoulders, pulling her in towards him.

She leaned into his chest, almost collapsing wearily against him. A fresh bout of sobs escaped her throat but this time her tears were shed directly into the folds of Sam's shirt, her hand twisting into the soft fabric. Sam draped his other arm around her too and held her gently, murmuring soothing sounds to the top of her head.

Finally she seemed to gain some semblance of control over her emotions as her breath evened out and the sniffling stopped. She relaxed her fisted grip and he felt her sink more heavily into his hold, where she stayed silently for a few more minutes.

"I'm sorry," she mumbled eventually, pulling away and leaning back against the wall next to him.

"So am I," he replied, his one arm still around her shoulders.

"I really didn't see this coming," she admitted with a pathetic attempt at a laugh.

Sam didn't reply, knowing there was nothing he could say that would help ease her pain right now. He hoped his presence would provide some small measure of comfort, even if it just meant she wasn't alone right now. He knew being alone was an issue for her and she had basically just been told she would have to face it again as of right now.

As if reading his mind, she spoke again, this time on that very subject.

"Remember what I told you about feeling so alone when nobody believed me about foster-dad number six?" she asked, her voice a raspy whisper.

"Yeah," Sam acknowledged.

"Well, I haven't felt that way once since I met Dean. Not once since I started traveling with him." She wiped at her face with her sleeve. "With you both," she added, though Sam realized with a sharp pang that she really meant Dean. "It was weird, because the very day I lost the last member of my family, it was like I found a new one."

They had met her right after Diego had killed her aunt. "It was like God was looking out for me for once," she continued, surprising Sam because she hadn't mentioned God before and he had been under the impression she wasn't a believer.

Sam remained silent, not knowing of any words to comfort her.

"I love him, you know," she said softly, clearly talking about Dean. "I almost told him that a few times but I've never said those words to anyone and I chickened out." She gave a little snort and a huff of humorless laughter escaped. "Glad I didn't," she declared. "Boy, would I have looked like an idiot."

Sam badly wanted to tell her that his brother loved her too but couldn't go against Dean's wishes. This was definitely bad but not as bad as when Sheldon had killed Dean in front of her in the dream. As unbelievable as it seemed, this was the kinder thing to do to her.

"Did I do something wrong?" she asked suddenly, sparing a quick, apprehensive look up at the hunter sitting next to her.

"No," Sam said quickly. "No, Tasha, it's just the way he is. It's not that he doesn't care it's just…"

"It's just that he does," she finished.

Sam nodded, realizing she knew Dean too well to completely believe the 'it was just a fling' thing.

"I feel so pathetic," she chuckled, the sound almost sounding like real mirth this time. "Here I am getting dumped by a guy and I acted like one of those clingy girlfriends that refuses to accept it."

Sam smiled down at her, relieved at the more familiar tone in her voice. "You gonna go all Glen Close on my brother?"

She grinned. "Don't tempt me."

Sam sighed. "If it's any consolation, he knows it's his loss."

She leaned her head against his shoulder. "Thanks," she said with genuine-sounding gratitude. "You know, I kinda love you Sam Winchester."

Sam knew how she meant the phrase, casual and friendly with a hint of a tease aimed at embarrassing him, but his heart still fluttered and the words still managed to send a pleasant shiver down his spine.

"I'm gonna miss you," she said more seriously.

Sam leaned down and kissed the top of her head. "Me too," he said softly.

They sat like that, together against the wall on the motel room floor for what seemed like a long, long time but was probably no more than half an hour before Tasha spoke again.

"So where'd he go?" There was no need to elaborate on who she was referring to.

"I think he went to steal you a car."

Clearly trying to sound lighthearted but failing miserably, Tasha replied. "Well, I hope he gets a red one; he knows I like red and sporty."

As if on cue, heavy footsteps approached the motel door but stopped just outside. The person stood still for a good minute and a half, the air heavy with his booted stillness, before moving away. Sam let out a deep exhale and realized when he heard Tasha doing the same that they had both been holding their breath in anticipation.

Sam lifted his arm out from behind the brunette and pushed himself up off the floor. "I'll just see what's going on," he said solemnly as he headed towards the door. Tasha made no move to get up or follow.

Outside, on the motel porch, Dean was standing about ten feet away from the door, fidgeting uncomfortably. Sam couldn't help but notice the shiny red Mazda Miata parked right next to the Impala.

Red and sporty.

His heart almost cried at the implications of Dean's choice of stolen vehicle. Dean had always only ever been able to express affection through actions rather than words. Sam knew he had been too blind to pick up on that fact and appreciate all Dean had done for him in their younger years but Tasha would surely note the specific selection of Dean's thievery and the obvious sentiment behind it. Though his brother's intentions had been good, the little gesture would make things that much worse and that much more confusing for Tasha.

Dean handed him a set of keys. "Tell her the tank's full and the owner's in Bermuda for two more weeks so it won't be reported stolen for a while," he said.

"How'd you manage…never mind." His brother's resourcefulness shouldn't surprise him any more. He took the keys. Obviously Dean had no intention of giving them to Tasha himself. "Dean, are you sure about this?" he asked, knowing this was his brother's last chance to change his mind.

Dean nodded. "It's for the best, Sam," he said. "She doesn't need to know what's coming my way."

The elder Winchester took one last long look at the closed door.

"You gonna say goodbye?" Sam asked, fidgeting with the keys in his hand and feeling tremendously sorry for his brother.

Dean shook his head. "I'll be in the bar," was all he said as he turned and walked stiffly across the gravel parking lot to the motel bar.

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Dean didn't return from the bar until almost ten o'clock that night. Considering he had started drinking before noon, Sam wasn't surprised at the drunken state his brother was in when he finally returned. The younger Winchester had gone looking for Dean around supper time but had been told curtly that Dean was fine and he was in the middle of hustling some local yokels so lay off and leave him alone. Sam hadn't taken offense and had returned to the empty room with a heavy heart.

He had been pounding away at the keys on his laptop when he heard the unmistakable sound of a repeated attempt to force a key into the motel room lock. The rattling of the handle and the clatter of the keys being dropped twice gave him a warning that Dean was drunk but he hadn't realized just how shitfaced until he swung the door open and saw his brother standing on the stoop, swaying.

"Hey S'my," Dean slurred, practically falling forward into his brother's massive chest. Sam gripped him firmly by the shoulders and half-guided, half-dragged him into the room and over to his bed. He didn't need to give Dean a shove onto the bed, he simply let go and let gravity do the work for him.

"Dean, man, you okay?" he asked, his voice full of concern.

"Course," Dean mumbled, trying in vain to sit back up. "Fffor a dead man wvalking."

Sam interpreted the drunk-speak with ease. It wasn't the first time he'd seen his brother drunk. It was, however, the drunkest he'd seen him. Ever. He sighed and attempted to take off the inebriated man's boots.

"S'my," Dean continued, growing passive and allowing Sam to hold his foot in the air as he untied his shoes for him.

"Yeah, Dean?" Sam's voice was gentle and held none of the usual judgement or scorn for his brother's current state.

"When I'm dead…" Dean gave up the struggle to sit up and lay back, his arms splayed out on either side of him in defeat. "You have to promishe me you'll find Diego and k-kill him."

"Dean, you're not going to die," Sam said, his voice taking on a distinct tone of begging. "Please don't talk like that." He got the first boot off and moved to the second.

"You hafffta kill him before he getzz Tash," Dean slurred, ignoring Sam's plea.

"Dean…"

"Promise me, S'm!"

"Okay," Sam relented. "Of course. You know I will." He dropped the second foot back down onto the bed. "But Dean, we're gonna find you a way out of this deal. I'm gonna save you and then we'll both go get Diego, okay?"

But Dean's eyes were closed and his breath had evened out to the slow, steady pace of a drunken stupor. He lay sprawled on the bed and Sam stood over him for a long time, staring down at what remained of his family and growing more determined than ever to find a way to save the stubborn bastard. Dean had been dealt one blow after another his whole life and never complained. He'd thrown his life away, no his soul away, to save Sam and now he had lost something else he loved for that same reason. Sam couldn't let it happen.

Sam grabbed Dean's coat from the back of the chair and draped it over his brother, his heart swelling with the realization of how much he loved him, how much he needed him. He sat himself back down in front of his laptop and continued the research he had been doing before the whirlwind that was hurt-scared-drunk Dean had interrupted him.

He grabbed his father's journal and opened it to a page near the beginning. There it was. The solution.

Doc Benton. Born in 1816 but still alive in the 1990's for John Winchester to take a crack at. If Sam could keep Dean alive, he could keep him out of Hell.

This could work. It was crazy and it was far-fetched and Dean would never go for it, but if the clues were accurate, then this could be Dean's only chance.

He let his gaze drift back to the gently snoring Winchester sleeping off his pain-induced bender and made up his mind. He needed to keep Dean alive.

He would let Dean sleep it off then in the morning, he would drag his brother's hungover ass out of bed and get to work on saving his life and getting him out of this insanely unfair deal once and for all.

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…(this leads into the episode Time is on My Side)…

A/N: Well, that's it for part1! Like I said before, Part 2 is coming soon so don't let the sad ending get you down. I will continue part 2 on this same story, so if you're interested, you can just put this one on alert. I also can't thank DanniMitchell85 enough for all the wonderful help – this is my first real fic and it was a bit nerve-wracking so a big thanks to you!

Thanks again for reading - I hope you all enjoyed the ride and please don't forget to leave a review on your way out! :-)