Dean swore as he slammed the door to the taxi closed. That man had been his only hope of retrieving Sam and Bobby from Purgatory. What the hell was he going to do now?

Dean leaned up against the side of the cab, putting his hands over his face before running them both backwards through his hair and bringing them to rest at the back of his head as he stared up at the sky in desperation. Cas was out of the question; if he'd been able to get in and out of Purgatory, he would have done so on his own ages ago and spared them the year in Monster's Paradise. There was only one other person who had ever gotten out…

Dean shook his head, forcing away the thought of Benny. He already owed the vampire so much, he couldn't ask him to do what he needed to get Sam. If that would even work... Dean shoved his hands in his pockets, finger finding his cellphone and wrapping around it instinctively as he sighed, rubbing at his face with one hand again before flipping the phone open and pushing the speed dial. Maybe Benny would have another idea.

He had to try.

Sam grunted as he forced the large stone back over the entrance to Hell, careful not to get sucked back down through the portal. The stone fell into place with a clunk and an ominous sort of hiss against the vacuum of the portal, then there was silence. Sam started to turn, but stopped, remembering who was behind him.

"Jess? You still there?"

"I'm here, Sam." A wave of relief washed over Sam at the sound of Jess voice coming from the riverside. She sounded stronger now. The pain in Sam's chest doubled.

"We have to follow the river back up about three miles, that way." Sam pointed out ahead of him and down the river, where the taxi driver would be waiting. "We have about an hour until the guy is supposed to meet us to get us out. Can you make it?"

There was a moment of silence, then a small laugh. "Yes. Sorry, I just realized I was nodding my head. I guess you couldn't see that, could you?"

A squeeze of pain that had nothing to do with Crowley's curse ran through Sam's chest as he smiled sadly.

"Soon, Jess. I promise." He heard Jess approach him, and felt something sharp poke at his hand. Glancing down, he realized the end of a long stick had been prodded into his hand.

"Here, it's almost like holding hands." Sam laughed, giving his end of the stick a small shake in response and hearing Jess laugh in return. "Let's go."

The woods of Purgatory were quiet as they made their way along the river. Every so often they would exchange small talk – how had Sam been, did he ever graduate from Stanford, was his brother still driving that old car of their dad's? Jess' voice grew stronger as they walked; by the time they had gotten halfway to the meeting point, she sounded almost back to normal. Sam was starting to have trouble disguising the pain around his chest now.

"Sam?" Sam snapped back to reality as Jess' voice invaded his attempts to mentally quash down the building pressure in his chest. He realized Jess had asked him a question.

"Sorry, what was that?" Sam kicked himself as he realized just how short of breath he sounded, and was sure Jess had caught the hitch in his voice as well. There was quiet for a moment.

"I'm sorry about this." Jess whispered. Sam stopped, confused.

"What? What do you have to be sorry for?" Sam asked, inclining his head backwards as if he might look at her. He could hear Jess fidget.

"If I'd never let Brady in that night… Sam, this is all my fault." For a moment Sam thought his heart had burst as he spun around to face Jess, eyes squeezed shut at the last moment.

"Don't you ever say that, Jessica." Sam snapped. His head was spinning. "None of this was your fault. Ever."

"Sam…" Jess' voice was low, sad. Sam had to turn back around to keep himself from looking at her. He waved his end of the stick in his hand to remind Jess to grab back onto it; she had released it when he turned around. "I love you."

Sam felt tears sting his eyes as he gripped the stick between them so hard he feared it might snap. "I love you too, Jess."

"Benny." Dean embraced the vampire with a grin as Benny smirked, swinging an arm around to clap Dean on the back.

"Hey there, friend." They pulled apart, Dean's eyes on Benny as he looked over the alleyway. "So, this is it, huh? Gates to Purgatory?"

"I guess so. This is where the guy disappeared with Sam, anyway." Benny leaned around Dean to look into the cab; the front seat was empty.

"I took care of it." Dean added. Benny nodded. "Any ideas how to spring Sammy back out again?"

"What about that angel friend of yours?" Benny asked, shooting a backward glance at Dean as he examined the walls of the alley. "How'd he get out?"

"Some feathers on a power trip up in Heaven, from what I've heard. Name's Naomi. You ever heard of her?" Benny shook his head, knocking his knuckles against the alley wall in defeat before turning back to face Dean.

"Well, it looks to me like we've got only one option." Benny offered, leaning against the taxi. "I don't suppose you've got any weapons I could sneak over there with me, huh?"

Benny's smirk slid off his face as he caught sight of the pain in Dean's face. He straightened up, clapping one hand on Dean's shoulder as he looked him straight in the eyes.

"He's family, Dean. I get it. I'd do the same thing in your position." Sam didn't look convinced. There was a tense silence as Dean just stared at him, usual snark and carefree remarks abandoning him for the moment. Benny patted Dean's shoulder, moving to stand in the middle of the alley.

"You ready?" Dean nodded, retrieving a machete he had stashed in the back of the cab. Slowly he unsheathed it, moving it from hand to hand with growing reluctance as he looked up at Benny once again.

"Thank you." Dean whispered. Benny smiled as best he could.

"Don't worry about it, Dean. I don't much belong around here anyway. I could use a vacation." Dean almost laughed.

"Like Hell you do. The moment you find Sam, you hitch a ride straight back here, fare's on him. You got it?" Benny grinned.

"I got it, friend. Now…" Benny gave himself a light shake, arms held slightly out from his side as he smiled at Dean. "I'm not getting any younger here." Dean nodded, eyes watering as he raised the machete.

"Thank you."

Dean swung.

Sam stopped as they reached the appointed meeting spot. Glancing at his watch, he sighed, rubbing at the pressure now causing black spots to dance before his eyes. Behind him, Jess lightly shook her end of the stick to get his attention.

"Sammy?" Jess whispered, fear evident in her voice. Sam straightened as best he could.

"This is the spot." Sam mumbled, looking around the clearing for any sign of the cab driver. Nothing.

"Maybe he's just… running late?" Jess sounded so hopeful Sam wanted to cry.

"I don't think so." Sammy let out a cry as his knees suddenly buckled, one hand scraping against the forest debris as his other grabbed desperately at the pain in his chest. His head collided with the forest floor and left him seeing stars.

"Sam!" He could feel Jess drop to her knees beside him, practically feel her struggle not to touch him. He rolled away slightly to try and keep her from doing so.

"It's okay. He'll be here soon…" Sam gasped, eyes clenched shut against the pain. Everything hurt…

A sudden snap resounded from somewhere to Sam's left and he froze. Beside his he could sense Jess had done the same. "Jess?"

"Someone's coming." Jess whispered. Sam grunted, attempting to sit up. "Don't, Sam!"

"I have to see who it is," Sam gasped, struggling to his feet. "Move back so I don't touch you."

Sam heard Jess stumble away behind him, and he opened his eyes as a familiar figure appeared through the dead trees. Sam blinked, not believing what he was seeing.

"Benny?" Sam mumbled, blinking once more as he stared in confusion at the approaching vampire. Benny grinned in response.

"Hey there, Sam. Your brother sent me to get you." Sam stared at him, realization dawning on his face as the gravity of Benny's situation sunk in. Benny's grin faltered slightly for a moment as he made eye contact with Sam, but it was quickly replaced with surprise as he turned and caught sight of Jess.

"Who might this be?" Benny asked, inclining a head towards her. Sam heard Jess shift slightly behind him.

"This is Jessica. My girlfriend." Sam caught the brief look of horror that flashed across Benny's face as the full force of Sam's statement apparently hit home. Benny moved forward, past Sam, one hand extended.

"It's a pleasure to meet you, ma'am." Sam caught a glimpse of Benny bending over in a light bow, apparently to kiss Jess' hand judging from the light laugh that followed.

"I like this guy, Sam. Where've you been hiding him?" Jess teased. Sam grunted an attempt at a laugh in reply.

"Oh, you know. Purgatory."

"Alright you, let's get going before your brother takes my head off." Sam groaned in equal parts pain and unamusement as Benny took the lead. He suddenly stopped, catching sight of Sam's hand still clutched at the fabric over his heart. "What's wrong?"

"Crowley." Sam managed, stumbling slightly as he began to sway. Benny darted forward in time to catch Sam as his legs buckled once more, a soft gasp eliciting from Jess behind him. Benny wrapped Sam's arm over his shoulder and gripped Sam around the waist.

"Little lady, if you wouldn't mind taking his other side-"

"NO!" Sam yelled, nearly winding himself. Benny looked at him in alarm. "Can't touch her." Sam gasped, coughing. "Part of the deal. Can't see her, either." Benny's mouth set in a grim line.

"Well, then. The sooner we get you two out of here, the better. Come on." Sam grunted as Benny forced them forward, Jess' footfalls sounding quietly on the underbrush behind them.

"Where are you taking us?" Jess asked after a few mins. Benny glanced back at her from his vigil of the surrounding forest, readjusting his grip on the barely-conscious Sam at his side.

"There's a portal a little ways ahead." Benny gestured to the woods in front of them. "We should be nearly there."

A snap and the sound of voices laughing made Benny freeze in his tracks. Benny turned, his face grim.

"Jessica, was it?" Sam tried to force his eyes to focus on whatever it was Benny was looking at, but he could barely turn his head. "I'm going to have to ask you to run."

"Sam." Sam moaned as Benny grabbed Sam by both shoulders and forced him to look at him. "you're going to have to make it to the portal on your own. I'll hold them off as long as possible." Sam attempted to mumble a protest in response, but Benny shushed him. He reached over to one of the trees nearest them, tearing off a sizeable lower branch as if it were no more than paper. He thrust it into Sam's hands like a walking stick.

"Go." Sam stumbled as his full weight dropped onto the branch in his hands, Benny releasing an animal-like snarl as he took off behind him. Sam took a shaky step forward as he heard Jess come up behind him.

"Come on, Sam." Jess whispered. Sam grunted, pain shooting through his chest as he took another step forward.

"Go, Jess. Hurry." Sam heaved himself forward again, air ripping from his lungs as pain like fire seared through his heart.

"I'm not leaving you." Jess snapped. Sam forced himself forward again. The sound of snarls and screams could be heard behind them now. They were running out of time.

"I see it, Sam!" Why did Jess sound so far away? Sam's head spun as his grip on the branch loosened. "Sam!"

Sam vaguely registered that something horrible had happened as a hand gripped his arm tight and hauled him forward. An arm wrapped itself around his waist as he was heaved forward, a dazzling blue glow now shining too brightly into his eyes. Sam moaned, his head swimming as his heart began to pound faster and faster within his chest.

"Almost there, Sam." Whose voice was that? Jess – why did she sound so close-

"No," Sam gasped, glancing to his side and catching sight of Jessica, arm wrapped around his side as her other hand held his over her own shoulders, supporting him as best she could. "Jess, you can't-"

"Too late, Sam." The smell of burning flesh filled Sam's nostrils as Jess heaved him up towards the portal. Sam could see the flesh on her face already beginning to peel.

"Jess." Tears flowed freely down Sam's cheeks as their eyes met. Jess was dissolving before his eyes.

"I love you, Sam." Jess whispered. She pressed her cracking lips to his, then shoved him into the portal. The last thing Sam registered was a pair of bright blue eyes disappearing into a cloud of smoke.

"JESSICA!"