Not proud entirely of this chapter, apologies in advance if it sucks.

Disclaimer: I do not own The Vampire Diaries or Supernatural.

Stefan was outside of a shack in the woods, talking on the phone with Damon.

"He's going to recover?" Stefan asked.

"Well, from being an Enhanced Original turned into a human? It's Ric, he'll walk it off, until he dies for good without his ring." Damon said before he noticed the pause on the phone. "Is there something you wanna tell me?"

Stefan considered. "I think it might be better if you see in person. It's not exactly something you'd listen to on the phone."

Stefan hung up and then he entered the shack, where were Dean, Matt and Enzo with bloodied and restrained Tripp Cooke sitting on the chair.

"So, why don't you tell us how deep your anti-vampire operation goes?" Dean asked, cracking his fingers.

"And what they've been up to, while you're here with us?" Enzo asked.

Tripp was silent as Stefan sighed and picked a hammer, hitting Tripp in the hand as Tripp screamed.

"They're doing the same thing they were doing when they were with me!" Tripp revealed as he turned to Stefan. "They're tracking vampires like your friend, Caroline Forbes!"

"Where are they now and how much do they know?" Dean asked.

"I'm not sure where but they know enough." Tripp said as Stefan considered.

"Take two hours, get the names of his men, what they know. After that, he's a liability. Get rid of him." Stefan said before he left.

Later, Whitmore College

Caroline was in her dorm room. at her desk, when she heard knocking and turned to see Stefan at the door. "That's weird." She muttered.

"What's weird?" Stefan wondered.

"None of your business." Caroline said as she approached the door. "We're not friends anymore, which means you can't just show up unannounced at my door. Goodbye." She was about to close the door, when Stefan entered.

"Hey, Caroline. Look, you're not safe. Tripp's men still have your name." Stefan explained.

"So, what, you're here to protect me?" Caroline asked, amused. "News flash, I don't need your protection. And more importantly, I don't want it."

Stefan sighed, when Caroline's phone rang and she answered the call.

"Hey, Mom, can I call you back? I'm trying to get a piece of gum off of my shoe." Caroline said.

"Actually, honey, this can't wait." Liz said. "Do you have any idea where Tripp Cooke might be?"

"Tripp? No, I have no idea. Why?" Caroline asked.

Mystic Falls

"Because one of his men just ran me off the road. And they're gonna kill me if they don't get him back." Liz explained with blood on her face and a man holding her at gunpoint.

Virginia

Dean glared down at Tripp, fuming in rage, remembering Gordon Walker, a bigoted vampire hunter who was killing vampires indiscriminately, even though some of them were harmless and innocent before Dean and Sam stopped and killed Gordon.

"You remind me of this asshat vampire hunter I used to know." Dean said as he neared Tripp. "He was good. I respected his skills. But he was a nasty son of a bitch, he killed his own sister who'd been turned and tortured and innocent harmless vampire who was feeding off cattle blood because she didn't want to drink from humans and he even killed a special kid with powers despite that he hadn't harmed anyone. And you're not that much different from him. Now, I hate vampires, sure. But I know not all of them are bad. You don't seem to care. So tell me, where are your friends?"

"You're on the wrong side." Tripp said.

"And how do you know your side is the good one, when some of the vampires hadn't hurt anyone?" Dean asked.

Suddenly, the door opened as Enzo and Matt entered.

"Update. Tripp's henchmen kidnapped the sheriff in Mystic Falls." Enzo said.

"What have you done?" Matt snapped.

"A contingency plan in case anything happened to me." Tripp explained.

"You still think you're on the right side?" Dean asked.

"You can set the meet by the edge of town off Old Miller Road. You can do the trade there, they know they'll be safe behind the border. And send Matt. They trust him." Tripp said.

McKinley

"How much are you looking forward to seeing your friends again?" Sam asked as he drove down the town with Bonnie next to him.

"I'm more hoping they're not in trouble." Bonnie said as they pulled over outside Scull Bar and Bonnie took a deep breath.

"Ready?" Sam asked and Bonnie nodded before they exited the car and entered the bar to see people dancing before Bonnie spotted a familiar couple dancing together.

Elena Gilbert stopped dancing with her partner as she stared in disbelief. "Oh, my God… Bonnie?"

Her partner, who turned around, revealing Damon Salvatore, widened his eyes. "Bonnie?"

"The one and only." Bonnie said with a smile before they ran to each other in a tight hug and laughed.

"Oh, my God, I can't believe it!" Elena said, barely able to hold back tears.

"You made it." Damon said.

Sam observed the scene, smiling. While he had not heard the most pleasant things about Damon, he could already tell that Bonnie was a good person even for someone like him and he could see now why Dean was protective of her.

Virginia

Enzo opened the door to reveal Stefan and Caroline. "Hello, gorgeous."

Dean turned and widened his eyes in shock at seeing Caroline. "Amanda?"

"Caroline." Caroline corrected. "Who's Amanda?"

Dean shook his head for a moment before recovering himself. "Just… someone I used to know. You look the same."

Caroline looked a bit thoughtful. "Huh. So I got a doppelganger too. Interesting."

"Caroline, this is Dean. Bonnie's new friend. A hunter, like Alaric. Dean, this is Caroline, Sheriff's daughter." Stefan said.

"Yeah, Bonnie mentioned you." Dean said.

Caroline nodded and was looking forward to seeing Bonnie again before entering the shack and seeing the bloodied Tripp. "What did you do to him?" She demanded.

"Oh he's fine, just a little blood loss, I think he may have an iron deficiency problem." Enzo said as he smacked Tripp on the face.

"Knock it off, her mother's life is on the line." Stefan said as Caroline came to undo the restraints on Tripp.

"Wait, just so I'm clear, all Caroline had to do to get you to treat her with a modicum of respect is for you to stop paying attention to her, right?" Enzo drawled.

"Shut up, Enzo." Caroline snapped. "And did he really need three chains? Who is this guy, the Hulk?"

"Don't look at me, he was already like that, when I got here." Dean shrugged.

"I didn't restrain him." Stefan added.

"No, but you let your sidekick Enzo do it. Because what could go wrong, when you team up with your sworn enemy?" Caroline asked.

"Look, can we skip all this Twilight drama or whatever this is here and focus on saving the sheriff?" Dean asked and Stefan and Caroline sighed, realizing he was right, there were more important things going on here.

"You're right. Liz's life is still on the line. Let's get him on the road." Stefan said.

"Tell your mum I send my best." Enzo said as he walked out.

McKinley

"So… King of Hell?" Elena asked after Bonnie had filled her and Damon in.

"It's difficult to digest, but it's true." Sam nodded.

"And while our kind comes from the Originals, your vampires come from Eve, the Mother of monsters and they can walk in daylight." Damon said, fascinated.

"Well, they don't burst in flames, they're just sensitive to it, it's just sunburn and vampire lore, the one we know, doesn't apply to them, stakes can't hurt them and like with you, holy items don't affect them. But I'm guessing decapitation applies to your kind too." Sam said and Damon and Elena tensed.

"Well, I may have heard some rumors about these vampires but I never encountered them." Damon admitted.

"It's only a matter of time before Crowley tries something again and we don't want to bring more trouble to your doorstep." Sam said.

"Come on, how bad can he be? He's not the first idiot with delusions of grandeur I've faced." Damon shrugged.

"Damon, if you saw how dangerous he is, you'd take him seriously. He could be just as bad as Kai, if not worse." Bonnie said and that made Damon take her seriously.

"Is that so?" Damon asked and Bonnie nodded.

"Well, if something happens, we'll be ready." Sam promised.

"If this Purgatory is as bad as you have described, I'm glad we didn't end up there. U sure as hell have no intention of dying again, not without a fight." Damon said.

Sam looked at Damon warily. While he had heard mostly unpleasant things about Damon, from what Bonnie had said, he had some redeeming qualities, though it was probably for the best to keep an eye out on him.

Mystic Falls

Stefan, Dean and Caroline were at the borders of Mystic Falls, when they saw a car drive towards them.

"They're here." Stefan said.

Matt and Tripp's henchman Greg exited the car with Liz in restraints and at gunpoint.

"Mom?" Caroline was about to approach, when Matt gestured for her to stop.

"Caroline, stop. The border." Matt reminded as Caroline stopped as she saw the blood on Liz's head.

"You're bleeding? What did you do to her?" Caroline demanded.

"I'm fine." Liz assured.

"OK, let's do this, let her go and you can have him." Matt said.

"Tripp first." Greg said.

"Let her go or I'll kill you." Caroline sneered.

"Sweetheart, it's OK. Stefan, let Tripp go." Liz ordered.

Dean and Stefan looked at each other before they shoved Tripp forward.

"OK, now he's across, now let her go." Caroline said as Greg let Liz walk towards them and Caroline and Liz hugged each other.

As Tripp approached, suddenly he turned pale.

"Are you OK?" Matt asked.

"What's happening to me?" Tripp wondered, when suddenly his throat was torn open and he gagged from the blood pouring out of his wound and he fell down.

"What the hell?" Dean demanded as Greg turned and ran off.

Matt knelt and looked at his mentor dying sadly before he turned to Stefan with a glare. "What the hell did you do?"

"It wasn't me. Enzo must have turned him into a vampire before we got here." Stefan realized.

While Dean was disturbed at the scene, he felt no sympathies for Tripp.

Later, Mystic Falls Hospital

"This is totally unnecessary." Liz said, while sitting down in the exam room.

"You hit your head, you could have a concussion and I know better than to trust that you're going to take yourself for a checkup back home." Caroline said before turning to Dean. "Thank you for helping her."

"It's not a problem." Dean said before turning to Stefan. "Stefan, was it?"

Stefan nodded.

"Would you mind if we talked in private for a moment?" Dean asked and Stefan frowned before Dean chuckled. "Relax, if I wanted to kill you, you'd never see it coming."

Stefan relaxed as he and Dean went outside and into the corridor.

"So, you're Stefan Salvatore. I read up about you. My name's Dean Winchester." Dean said and Stefan's eyes narrowed before realizing where he had heard 'Winchester' before.

"You're John's son." Stefan said and Dean nodded.

"I know my Dad was in Mystic Falls investigating a case involving you and your brother but he then let it go and walked away. I read his journal. That didn't sound like him. When I met Bonnie and she mentioned that some vampires can compel and then your name popped up, it didn't take much for me to put it together." Dean said and Stefan looked a bit ashamed. "You compelled him to leave and let that case go, didn't you?"

Stefan sighed, knowing there was no point denying it. "I was trying to protect your father. If you knew what Damon is capable of—"

"I get it." Dean said, much to Stefan's surprise. "And while I'm not happy about the whole situation, you were trying to make the best out of a bad situation. That's all anyone can do. Who knows what could've happened back then but I appreciate that you were trying to look out for him."

Stefan nodded before he began to ask. "Why did you come here?"

"Because Bonnie helped me. We've been looking out for each other. And I owed her that much to bring her home safely." Dean said.

Stefan nodded in appreciation.

"And I know about you and your brother and what you've been through and I can tell that you're trying, but Damon…" Dean trailed off.

"I'm not gonna justify or defend him but… when he tries, he can be good. I'm just not gonna cut him loose, when there's a chance he can come through, when it matters." Stefan said and while Dean saw some similarities between himself and Sam and Stefan and Damon with what they would do to protect each other despite how far they might be gone, Dean still was unconvinced that Damon was worth it, despite that Stefan and Bonnie would care about him.

"I guess I can understand. A wise man once told me, 'Family don't end in blood, but it doesn't start there either. Family cares about you, not what you can do for them. Family's there, through the good, bad, all of it. They got your back even when it hurts. That's family.'" Dean quoted as Stefan smiled.

"When it comes down to it, Damon is there, when it matters. But… I guess it's easier for him to do his worst, when he has the chance to do his best. I'm just worried that the day may come when it's either him or everyone else." Stefan said.

"Well…" Dean sighed. "Let's just hope it doesn't come down to it."

Apologies if this chapter felt a bit rushed but this was mainly to deal with Tripp and Bonnie reuniting with her friends, not sure if it was OK.

Dean's reaction to Caroline is because of Candice Accola playing Dean's high school sweetheart in Supernatural who Dean dated briefly in 4x13 as shown in flashbacks in that episode, LOL!

I skipped the Damon/Elena things and tried to make them more about them catching up with Bonnie, but been a while since I've done the small friendly talk scenes, so not sure if the scenes were OK, but do not get me started on Damon/Elena or Elena in particular.

What's the large difference between Stefan/Damon and Dean/Sam as their brotherly bonds is while they pull nasty stuff at each other sometimes, with Dean and Sam it's mainly out of a misguided attempt to save their brother which has unintended catastrophic consequences for everyone, while Stefan's nasty stuff is mainly with his humanity off and Damon does most of his shit with his humanity both on and off whenever he is unhappy and he lashes out to make everyone around him as miserable as possible, really, even soulless Spike would be disgusted by Damon, so I felt like this was a good opportunity for Dean and Stefan to talk since I'm sure their interactions would be interesting.

While Damon's interactions so far with Dean and Sam have been decent, Damon is Damon, so you can expect a confrontation soon and I don't want to be Damon, when it goes to a head.

So, what do you guys think?

Please review and let me know if you have been enjoying this and want for me to continue.