CHAPTER THIRTY: Poughkeepsie

As Dean slowly regained consciousness, he felt the rough texture of rope securing his chest to a chair and the cool metal of cuffs wrapped tightly around his wrists. Slowly prying his eyes open, the first thing he was greeted with was Meg's smug face.

"Oh you gotta be fucking kidding me." He grumbled, rolling his eyes in aggravation as a smirk tugged at the brunette's lips.

"Don't act like you don't enjoy being tied up." She quipped, stepping back a few inches and stuffing her hands in her back pockets.

"Can't you guys leave me alone? I still got nine months left and then we can spend plenty of quality time together. Just like we use to." He promised, giving her a suggestive wink with an arrogant smile plastered to his face.

She scoffed, sauntering towards the demon, climbing onto his lap and straddling him. "We could always start early." Her voice got seductively low as she leaned forward to where her hot breath was tickling his ear. "What should we do?"

"How 'bout I rip you to shreds?" Dean suggested, though his tone was teasing. Even though he hated to admit it, he had a soft spot for the vindictive demon sitting on top of him.

Meg leaned back, her mouth agape in fake astonishment. "Dean come on, let's be honest with ourselves. You and I made one helluva team before you had to go off and do your own thing with that stick-shoved-up-my-ass brother of yours." She pointed out, meeting his amused green gaze.

"Yeah well, all great things right?" He paused, remembering how they really had been great together, although the clueless hunters upstairs wouldn't have approved.

"Maybe a little to the left." Meg suggested, resting her arm on Dean's shoulder. He glanced at her with a wicked smile and pitch black eyes before he returned his attention back to the irritating hunter at his knees. With one quick motion, he wrenched the jagged knife he had shoved into the man's abdomen a hard left. A broken cry escaped from the hunter's throat as he fought desperately against the invisible force keeping his seated on the ground. The man struggled to form a coherent sentence around the piece of cloth wrapped around his head, but nothing but muffled complaints surfaced.

"You use to hate hunters." Meg observed, drawing Dean back to reality. "Now look at you, protecting them as if they were your own blood."

As if just now noticing where he was, the eldest demon looked at Meg suspisciously. "Why are we in Bobby's basement?"He demanded, a bad feeling forming in his gut.

She stood up, her eyes never leaving the middle Winchester's trapped form as she walked over to one of Bobby's work benches.

Dean, trying not to focus on Meg who was ripping an old rag in half, was debating whether or not he should call for Sam. But, he didn't want to give Meg the satisfaction of making him scream.

She started towards him, a thick piece of fabric gripped in her right hand. "Meg listen, you don't have to do this. We can-" His proposal was cut short by the brunette gagging him, making sure it was nice and tight.

A sly grin crept across Meg's face as she took a step towards the stairs. "Can't have you yelling to warn those hunter friends of yours. Thank God for hex bags or Sam would've already been down here."

Dean tried to respond, now knowing how infuriating it was to have your speech cut off. "But, since you and I have so much history, I'm going to make you a deal. It's what we're good at right?"

The middle Winchester answered her with a glare as she pulled out the demon killing knife that had been tucked in Dean's waistband. "Now, I can't drag your ass downstairs early because Crowley technically made you a deal. But, I can make you a counter offer." She purred, trying to sound persuasive as she continued. "I won't go up and kill poor little Sammy and that family of yours if," She paused, taking the demon's now black eyes as a good sign. "And only if, you agree to come with me. Right. Now." She finished, stressing the last two words.

Dean muffled through the gag, annoying Meg enough that she rushed over and tugged it out of his mouth. "What?" She snapped, losing patience.

"I said." He started, lifting his gaze to meet hers. "That you can kiss my ass." The brunette looked like she was about to smack him so Dean did what he did best, he kept talking. "Come on, Meg. This isn't you. Do you really want Crowley's hand shoved up your ass for the rest of however long you manage to stay kickin'? You used to talk about overthrowing Crowley."

Meg stopped and considered him, looking on the verge of letting him go right as the basement door opened.

….

"Have any of you seen Dean?" Sam asked as he made his way down the steps after checking for his brother on the upper floor.

Bobby looked up from the paper he was reading and looked thoughtful. "Last I saw he was out workin' on that car." He said distractedly, returning his attention to an article.

Sam looked slightly concerned as he approached the back door, poking his head out of it in search for the middle Winchester.

After calling his name multiple times, the youngest demon started to become extremely worried as he shut the door. "Bobby, he's not out there."

The baseball capped hunter shrugged, glancing up at Sam. "Not my day to watch him. Maybe he went with John to get some food."

The tall demon pursed his lips, almost positive Dean would've said something. Figuring it was worth a shot, he walked over to the basement door and opened it.

….

Luckily for Meg, they were far enough in the basement that whoever was at the top of the stairs couldn't see them.

"Send him away before I slice that pretty skin of yours wide open." She whispered harshly, putting the engraved knife up to the eldest demon's throat.

"Dean?" Sam called, panic slowly seeping into his tone.

Dean swallowed, meeting Meg's fierce glare. "Yeah, down here Sammy. Just looking for a rag. I'll be up before you can say Poughkeepsie."

Sam hesitated, confused why his brother was using their 'drop everything and run' word. "Uh, need some help?" He answered back, hoping he sounded casual.

Meg applied light pressure to the blade, a small spark of orange flying from the cut. "No, I'm good. I'll talk to you in a few." Dean sent out a silent prayer, hoping his brother wasn't stupid enough to come downstairs.

Meg barely had time to blink before she felt a gust of wind behind her. Moving fast, she positioned herself to where she was standing behind Dean, blade still pressed to the demon's neck.

"Meg, let him go." Sam demanded, eyes switching to black.

The brunette chuckled, looking unimpressed by the demon standing before her. "Look who's trying to be the hero. How cute." She quipped, sarcasm lacing her words.

"Sammy, go." Dean growled, stiffening as the demon behind him carved another small slice.

The youngest Winchester's eyes flicked to his brother before returning to Meg, looking like he could rip her head off. "You guys told him he had a year. Quit trying to go back on your deal!" He yelled frustrated his brother kept getting put in danger.

"Hey!" A voice yelled, coming from the cellar entrance on the other side of the basement.

Meg turned her eyes, orbs becoming enveloped in darkness as she rounded on John Winchester, looking utterly pissed. She eyed the colt warily, wishing to Hell the old hunter hadn't found it. Gripping Dean's hair and pulling his head back to reveal his neck, she held onto the blade tighter.

"Really want to play chicken?" John dared, smug as he watched Meg's grip loosen.

It only took her .027 seconds to realize she was completely fucked, disappearing quickly before the bearded hunter had time to bury a round into her chest.

Dean's whole body relaxed, slumping in the chair slightly as Sam rushed over to him to undo the ropes. Seconds later John was right there, unlocking the demon warded cuffs.

"Fucking bitch." The eldest demon grumbled, standing up and shoving his brother away who was hovering over him. "I'm fine Sam."

"Did she hurt you?" The aged hunter questioned abruptly, looking genuinely concerned.

"Of course not. She's not that stupid." He answered back gruffly, walking away from the pair. "I gotta go take a shower. Or five."

….

"How was the hunt?" Dean asked as he sat down on his bed, towel drying his hair as Jo pulled up a chair with a fresh purple bruise forming on her left cheek.

She raised her brows and gave a cocky grin. "You should see the other guy." She joked, noticing how the demon wasn't his normal arrogant self.

He shook his head, setting the towel down next to him. "She was going to let me go."

"What?" Jo questioned, confused by the sudden topic change.

"Meg." He clarified, continuing when he saw the blonde nod in understanding. "Before Sam came down she was gonna let me go. I saw it in her eyes." He seemed sad, rubbing a calloused hand down his face.

"Then why didn't she?" The young hunter seemed doubtful, not believing in Meg's ability to be caring.

He lifted one shoulder half-heartedly. "She got scared. Plus, returning to Crowley without good news was never a walk in the park." Dean cringed as if he knew what that was like, but Jo decided not to push it.

She looked at the demon sitting infront of her and it suddenly dawned on her. Dean didn't want to go to Hell and it was showing more and more each day. "You're scared aren't you?" The blonde asked quietly, her tone serious as she met Dean's grief-stricken gaze.

"I'm scared about what Sam might do once I'm gone." Dean scooted forward on the bed to where his body was facing Jo. "You got to promise me you won't let Sam try to bring me back. Once I'm gone, let me stay gone." He pleaded, his eyes shining with fear.

As the young hunter looked into those brilliant green eyes, she couldn't help but think about how truly human the Winchester brother's were. With that in mind, she knew she was only going to be able to give one answer.

"I promise."

….

"I want to kill Azazel." Dean proclaimed, slamming his hands down on the wooden table in the kitchen. John, Ellen, Bobby, and Jo all looked at him from their seats as if he had lost it.

"Don't we all?" Sam said, his tone light from his position leaning against the counter.

Dean rolled his eyes and stifled the groan that threatened to escape his throat. "I have nine months left. And I'm not about to roll over and die. So, I figured, since I'm going to Hell anyways, I might as well go out with a bang." He finished, smiling broadly.

Sam felt his heart ache. He hated hearing his brother talk about his damned soul as if there was no way of getting out of it.

John looked amused as he took a sip from his beer. "That's pretty ambitious."

"That bastard has done more things to my family than I can count. Hell, he's got mom out there somewhere. We've got a way of killing him." He reminded, referring to the colt. He quickly glanced at each person around him, continuing with determination in his tone. "Now, I'm going after that yellow-eyed dick. Who's with me?" The eldest Winchester asked, looking around at the group with a hopeful gaze.

"Hell, you know I'm in." Bobby agreed as he leaned back in his chair with a smirk.

Jo looked at her mother for confirmation with puppy dog eyes Sam could be proud of.

Sighing heavily and with disapproval in her tone, Ellen reluctantly nodded. "We're in."

"Why not? If it'll get me my wife back." John finally consented. All eyes landed on the youngest demon with expectant eyes.

"Fine!" Sam relented, throwing up his hands. He didn't like it, but there was no way in Hell he was letting his brother do it without him.

A small gust of wind alerted the group of a new arrival. All head's turned to the living room, Sam instantly scowling as the newcomer spoke. "Got room for one more?"

….

TBC

1.) Yes, I imply that Dean and Meg have had a sexual history. No, it won't be happening in this story.

2.) Any guesses who wants to join the group?

3.) Thanks for all the reviews, you guys are da bomb.

4.) Please continue to read and review. I can't tell you guys how much I appreciate it.