This was a pretty good night, Dean thought as he downed another shot. He couldn't remember the last time he'd been this good; hell, he was even bordering on content. Coming down off a freaking awesome hunt, decent bar, good alcohol, and – Dean let his eyes trail appreciatively over the woman nearly in his lap – excellent company.

Yeah, his life was pretty fucking good.

In the two months since the devil's gate had opened, they'd managed to send almost thirty demons back to hell. Sam was alive, researching heavily but also willing to indulge Dean when he wanted to do something other than hunt together. When they did hunt, they clicked, working together as a seamless team that made anything they did seem downright easy. Dean admitted to himself that he'd feltt a bit of a rush when their precise and fluid teamwork had actually scared a couple of newbie hunters two states ago. If he was going to die in ten months, he'd like to go out a legend.

But right now, hunting was the last thing on his mind. Sam was back at the motel, ostensibly resting, but Dean knew better; he just liked to remain ignorant about it. Safer for all concerned, especially Sam. So there was nothing to stop him from hooking up with the woman – Cheryl? Sherry? Sharon? Something like that – and just enjoying himself tonight.

Dean had a To-Do list, all the things he'd like to accomplish before the hellhounds came barking. On that list, at #7, was a natural redhead. He'd been around a few times, had fucked women of all hair colors, but never a real redhead. Several bottle reds, strawberry blondes, auburn beauties, even a carrot top or two. But true natural fire-engine red hair occurred in less than 2 of the population, and so far Dean had only ever seen one, a beanpole teenage guy who went by the unfortunate nickname of Rooster.

Until tonight, that is. Because Cherri here was a knockout, tall and shapely with arresting Roman features, and her waist-length deep red hair was as natural as they come. Dean had gotten pretty good at spotting dye jobs over the years – good skill to have as a hunter, identifying when your target was trying to disguise as something else – and this was a shade no bottle could imitate.

It helped that she was a tequila fiend too. They'd been flirting since the moment they laid eyes on each other, and managed to kill a bottle between them, Cheryl matching him shot for shot. Dean was feeling the buzz, the way his body felt looser, his mind blanking out the bad parts of life to focus on the stunning woman now draped across him, one hand delicately playing with the hairs at the back of his neck.

He cupped her cheek and brought her lips to his, sealing them in a fiery kiss, tongue darting out to lick the flavor of tequila and lime from her mouth. She moaned into his mouth, turning and pressing her breasts into his chest as one leg slung over his thighs. He let his hand trail up her thigh, sneaking under her short skirt to trace the edge of panties as his other hand tangled in that gorgeous hair.

She broke the kiss with a gasp, leaning her head back as her chest heaved. Dean let his lips trail down her throat, nipping at the pale skin. "Bathroom," she gasped, squirming slightly as his teeth scraped her pulse point. Dean wholeheartedly agreed with that plan, sliding out the booth and helping her up. Wrapping an arm around her to keep her close, they stumbled slightly, giggling as they made their way through the crowd to the bathrooms.

Bursting their way through the men's door, Dean had just enough presence of mind to lock the door behind him before pinning Sherry to the wall. She opened her mouth to his kiss and took control, tangling tongues together as hands wandered, pushing aside clothing and sneaking underneath to clutch at fevered bare skin.

Within minutes his shirt was on the floor along with her panties – oh yeah, she was a natural redhead; Dean was made of awesome – and he paused in tonguing her breasts long enough to yank out his wallet to fetch a condom before letting his jeans slide down his legs to puddle around his ankles. She mewled as his fingers delved deeply into her, thumb rubbing her clit, but her hands were mostly steady as she ripped the foil open and rolled the latex down over him.

He slid into her in one hard thrust, her long legs wrapped around his waist as his hands supported her ass. She groaned throatily, fingers scrabbling at his shoulders as he fucked her hard against the wall, mouth sucking dark bruises into his neck. Dean lost himself in the sensation of warmsofttight, smooth skin under his hands and mouth, and the consuming pleasure throbbing through him.

Sharon screamed out her orgasm, barely muffled by the mouthful of shoulder muscle she'd latched on to, and Dean bared his teeth, grunting as he thrust the last couple times before moaning out his own release. He rode the high before letting it fizzle down into a warm loose glow that turned his muscles to liquid, aided by the tequila thrumming with the blood in his veins. They remained there for long moments, clinging and calming down, and Dean felt fucking fabulous.

Until she chuckled, a dark heady sound. "Was that good for you, sugar?"

A chill rushed up his spine, immediately canceling out the endorphin buzz he'd been relishing. Yanking his head up, he stared at the woman still in his arms, right into blood red eyes.

He'd never gone that soft so fast in his life. Which actually was a good thing, as he slipped out of her with little fuss, and would have dropped her, except for the vice grip her legs had around his hips. She grinned, eyes going mostly back to normal but he could still sense the darkness behind them.

"What are you doing here?" he demanded hoarsely, wishing his legs had enough strength in them to step back, step away from the demon.

"Don't be like that. Didn't you have fun?" she murmured with a wicked smile. "I thought you might like to celebrate."

Dean swallowed against the nausea crawling up his throat. "Celebrate what?"

She leaned in close and whispered, "Your freedom." He jerked back, but that left her entire weight supported only on him, throwing him off balance. He stumbled forward and slammed her back against the wall roughly, barely catching himself with hands braced on either side of her head. She grunted on impact, tightening her grip on him as she chuckled. "Oh honey, I should've known you'd like it rough."

"What do you mean, my freedom?" he spat, skin crawling at her every touch.

"I mean that in ten months, you don't have to worry about my pets coming for you. You get to keep your gutter soul, live however long you can manage."

"What?" Dean didn't understand. Did Sam succeed? She looked far too smug for someone who'd just been cheated out of a prize. "I thought we had a deal."

"We did. Deal's off."

"You're breaking it?"

"No. You did."

That coldly satisfied pronouncement froze him, horror flooding his veins to drown out the last lingering alcohol and lust. No. No. This couldn't be happening. "No," he managed through a constricted throat. "No, I didn't. I swear. I've never tried to get out of it. I've kept my end."

"Are you sure?" she smiled, a predator's grimace. "I told you, you try and welsh or weasel your way out, the deal's off." She leaned in, ruby lips brushing his ear as she whispered, "Maybe you should have let Sam stay in law school a bit longer. Because then he might've known that means you and anyone working on your behalf."

She released him then, skirt sliding back down as her legs found the floor to support her weight before she pushed him back. Dean stumbled, jeans still twisted around his ankles, and fought not to throw up. "Sammy found something tonight, tried to break our deal." She laughed as she straightened her shirt and smoothed her hair. "Well, he succeeded. Just not in the way he thought."

She unlocked the door as he scrambled to pull up his jeans, numb legs barely keeping him upright. He wanted to cry, to vomit, to deny everything she said. He wanted to rush her, wrap his hands around that skinny little throat and make her beg for mercy. He wanted to force her to take it back, to keep the deal, to keep him. Not Sam. Not Sam, oh please God. He wanted . . .

She paused in the doorway, raking those red eyes over him contemptuously. "Oh, and Dean? Don't bother calling. I won't answer." With that, she swished out the door.

Oh God. Sam . . .

Dean ripped his shirt as he yanked it back on and bolted out the door, nearly knocking people over as he ran for the back entrance. The girl was nowhere in sight, but she didn't matter anymore. He had to get to Sam. Had to find him before it was too late.

The urgent need to GET TO SAM overrode everything. He didn't remember getting in the Impala or driving back to the motel. All he could think of was the demon's harsh words, that bitter kiss two months ago, the sight of Sam so still and gray on the bed, the knowledge that he couldn't let anything happen to him, not again, oh please not again . . .

The next thing Dean knew was trying to force his key into the motel room door, calling out for his brother. No response. Maybe he went to get coffee, or food, or to find Dean. Oh please, just let him have stepped out. His hands shook, jangling the keys until he dropped them on the ground. He banged against the door, yelling out, "Sam! Answer me, damn it!"

Still no response. Lights on inside, the bluish glow on the curtains recognizable as light from the laptop screen. Dean cursed and kicked the door. The second kick broke the doorjamb and the door slammed open. He rushed inside, calling out, "SAM!"

Then the whole world came to a jarring stop.

Sam lay sprawled out on the floor, eyes open and staring at the ceiling. There were chalk lines, bowls of liquid, the smell of burned incense in the air, and an old book crumpled under Sam's outstretched arm. The whole scene burned into Dean's eyes, details sharp and indelible: the cloudiness in Sam's eyes, the gray pallor of his skin, the utter stillness despite the uncomfortable angle of his legs.

Then Dean was on his knees, vomiting so hard it was coming out his nose, stomach aching nearly as much as his chest as he sobbed around the heaves. This couldn't be happening. Dean was supposed to die, not Sam. He'd made that deal so Sam would live, could go and find that elusive normal he craved. He wasn't supposed to die trying to save Dean. Dean didn't want to be saved. The price was too high.

But that price had been paid. Twice.

Somehow he crawled over to Sam, tears still blurring his vision. One shaking hand touched his face, feeling the cool rubbery skin. He'd failed. He'd died hours ago, alone, while Dean was off drinking and screwing the demon. Dean had to turn his head as he retched again, only bile and stringy saliva coming up to burn his throat almost as much as the self-loathing did.

Time passed; minutes, hours, or days, Dean didn't know, as he stayed there on the floor beside Sam's body, paralyzed by despair and failure. This was his fault. Sam died because of him, because he was a good brother and tried to save Dean's sorry stupid self. Dean had failed his family, again. But this time there was no hope. He couldn't fix this. Not this time. He was out of chances.

Was the human body meant to feel this much pain? Was his heart supposed to survive having the world shatter and rip it to shreds twice? How could it last in the face of such overwhelming pain, when each breath felt like dying? When every movement was hopeless unendurable agony?

Apparently it couldn't. Eventually Dean only felt numb, disconnected. He let his fingers drift over Sam's face and tenderly closed his eyes, not able to take that blank accusing stare any more. Sam had to be uncomfortable on the floor. He shouldn't stay there; the carpet was filthy. Carefully Dean gathered Sam up in his arms and lifted him up onto the bed, arranging him on his side like he knew Sam liked to sleep. He looked young, at peace, and Dean brushed the hair away from his forehead, remembering all the fights about haircuts.

Stepping away from Sam hurt, but it was a dull, distant ache that barely penetrated the haze he was in. Moving slowly, as if he'd break if he moved too fast, he crossed the room to close the door and put a chair behind it to make sure it stayed closed despite the broken doorjamb. He shrugged out of his ripped and stained shirt, tugging on another as he picked up his phone.

After two rings, the phone on the other end picked up. "Hello?"

"Hey Bobby," Dean said wearily. Talking took an extraordinary amount of effort, but he had to let Bobby know. Had to give their old friend that.

"Dean? What's wrong?" Bobby was sharp all right, picking up on Dean's tone. As if he knew already that the world had come crashing down.

"Sam," Dean choked, tried to breathe around the huge lump in his throat. Bobby started to say something, but Dean cut him off. "Met the demon. Deal's off. Breach of contract."

Silence. Bobby understood. Sam had obviously told him about the conditions of the deal, probably recruited his help too. Dean had to fight down a sudden surge of anger. They shouldn't have. He wasn't worth this.

He licked dry lips and forced himself to continue. "We're in Ten Sleep, Wyoming. Trail Dust Inn, off exit 93. Room 11."

"Dean . . ." Oh God, Dean couldn't stand to hear that sound from Bobby. Once had been enough, more than enough, for an entire lifetime. He couldn't listen to whatever Bobby wanted to say. He had other things to take care of.

"Just thought you oughta know," he mumbled, and barely heard the "Dean! Don't you do anything stupid, boy," before he ended the call and shut his phone off. He tossed it on his bed, then rummaged in his duffel to pull out his favorite Colt 1911. It was freshly cleaned and oiled, and he knew it wouldn't let him down as he carefully loaded the clip and snapped it into place.

He climbed up on the other bed and settled back where he belonged, at Sam's side. He wrapped himself protectively around his little brother, ignoring the chill of his flesh, holding him like he used to when they were kids, tucking that mop of shaggy hair beneath his chin. He breathed deeply, closing his eyes as the familiar scent of shampoo, cheap motel soap, dust, sweat and Sam rose into his nostrils.

He had let him down again. Dean could only hope that Sam was with Jess now, at peace. Maybe being embraced by his mother for the first time in memory, maybe receiving a long-overdue proud backslap from his father. Somewhere better than here, at least, somewhere he could be happy.

As for himself, Dean had no illusions. He wouldn't be seeing anyone, not where he was going. He'd screwed up too bad on this one, and forgiveness just wasn't possible. Not when he'd let down his family so badly. They don't let faithless failures into heaven.

When Dad had started hunting, charging Dean with the task of being Sam's guardian, he had promised to protect Sam, not just bodily, but to shield him from the worst parts of the life they led. He'd done just that all throughout their childhood. Just because Dean knew what lurked out there in the dark didn't mean that Sam couldn't be a kid as long as possible, couldn't hold on to the fragile innocence which was often the first casualty in war.

But in that protection, in shielding, Dean had seen things, done things, that Sam could never know about. There was a reason why Bloody Mary had made his eyes bleed. Shit, there were many reasons, many secrets, all of which tainted him, made him into a worthless "gutter soul". When Dean had embraced the life, the hunt, he also forever embraced the knowledge that the light at the end of the tunnel was always going to be hellfire. The deal had changed nothing except to let him know the when and how, eliminating the surprise. The destination was never in question, be it from a demon's kiss, a second-too-slow dodge of eviscerating claws, or a throw into a tree acting as the last straw for a skull weakened by too many impacts and concussions.

But Sam, despite all his angsting about his so-called dark destiny or whatever shit his emo mind latched on to, was intrinsically a good person. Much better than Dean. He had faith, prayed, believed in a good Dean had given up on years ago. He was Dean's conscience, the one that kept him from spiraling off into the darkness like the things they hunted. If not for Sam, Dean might have been the monster the FBI believed him to be.

Dean might burn, but Sammy wouldn't.

Dean held Sam's body tight, curled around him reminiscent of long ago when Sammy would crawl into his bed, teary-eyed and scared from nightmares that could only be chased away by his big brother. Dean could protect him then, and did it gladly. But not now. Not anymore, despite doing his absolute best. Because his best simply wasn't good enough. He had failed.

Dean's hand shook as he picked up the gun off the pillow, trying to prepare himself for being separated from Sam one last time. This was his price to pay, for not being good enough, for letting Sam die because of him. Maybe Bobby would bury them together; they could at least have that.

Taking a deep breath, Dean cocked the gun and placed the barrel in his mouth, tasting cold metal and gun oil and the faint sharp tang of gunpowder. She had tasted like bitter ash and sulfur. Kiss of death either way, one-way ticket on the expressway to hell.

Dean closed his eyes and pulled the trigger.