"Mysterious Smoak"

Disclaimer: I don't own the characters; those belong to their original creators. The way it's all stringed together is of my making. No profit is being made out of this (*sigh* unfortunately).

While the chapters in this story can be seen as separate entries, they all have the same backstory in common. Think of it as each chapter being a "what if" moment for the characters yet with all chapters sharing the same backstory.

Backstory:
- Felicity meets the Winchesters in 2012 (reality; 2011-2012 / verse; 2012-2013) = S9 (verse; 2015-2016)
- Timeline of "Arrow" is pushed forward by 2 years so the ages are the same (therefore Oliver was shipwrecked in 2009 and saved in 2014) = S2 (2015-2016)

Ages:
- Dean Winchester (b. 1979) = 36 years old (in 2015)
- Sam Winchester (b. 1983) = 32 years old (in 2015)
- Oliver Queen (b. 1987, not 1985) = 28 years old (in 2015)
- Felicity Smoak (b. 1990, not 1988) = 25 years old (in 2015)
- John Diggle (b. 1979, not 1977) = 36 years old (in 2015)
- Sara Lance (b. 1989, not 1987) = 26 years old (in 2015)
- Roy Harper (b. 1993, not 1991) = 22 years old (in 2015)
***Ages of the "Arrow" characters are the same here as they are on the show (it's just the changes in dates that are different)

REASON why this is listed under "Arrow" only: because of Felicity.

Chapter Summary: Dean just met Cain and he needs more information yet with him and Sam not speaking, who does Dean turn to for information?
Inspiration: I just couldn't help myself!

Spoiler(s): everything up to ep. 9x11 ("First Born") for Supernatural and everything up to ep. 2x11 ("Blind Spot") for Arrow.
Time Frame: At the end of the episode for both shows.

A/N: At the end to avoid additional spoilers. Not beta-ed and this is the first time I'm writing for Arrow.

NOTE: This 'chapter' was originally posted on Jan. 24, 2014 under my "A Moment In Time" (Ch. 38).
It's interesting how the first posting was done on Dean Winchester's fictitious birthday and now I'm reposting it on Jensen Ackles' birthday (the man we plays Dean).

*SPN*Arrow*SPN*Arrow*SPN*

"Personal Researcher"

"After I kill Abaddon, you're next!" Dean Winchester ruthlessly declared at the King of Hell after punching him. The hunter was outraged.

"You don't mean that. We're having too much fun." Crowley quipped.

Dean scoffed as he backed away, putting some distance between himself and the demon.

"Listen up! Even with the Blade, we're gonna need all the help we can get against Abaddon." Crowley called out before the hunter could truly shut him out. He knew his deception wouldn't bode well with the seasoned hunter and yet it needed to be done. He also needed the hunter to patch things up with his brother so that the team could take on Abaddon.

"Go find the Blade."

Crowley sighed, "It's always something with you boys, isn't it?" He sniped mostly to himself before he disappeared to the deepest parts of the ocean to find the First Blade.

Dean exhaled once he felt the tension in the air leave with Crowley's presence. He knew that he should never trust the demon king and yet doing so had led him to the only weapon that could kill Abaddon, the very demon that had killed his paternal grandfather shortly after he had time-traveled into Sam and Dean's lives.

Just the thought of killing Abaddon had brought Dean's attention down to his arm. He rolled the right sleeve up to reveal the mark that Cain had passed to him. He didn't know much about the mark before meeting Cain but Dean didn't hesitate in accepting the mark if it meant that he could kill Abaddon once and for all. As he looked down at the burned mark, Dean couldn't help but wonder what it is he had signed himself up for.

"I can give you the mark Dean, if it's what you truly want." Cain proclaimed as the demons swarmed the house.

Dean's jaw dropped. "What? What are you talking about?"

"The mark can be transferred to someone who's worthy." Cain explained.

Dean blinked. "You mean a killer like you?"

"Yes."

"Can I use it to kill that bitch?" Dean asked, not even wanting to dwell on the real meaning of what 'being worthy' meant.

Cain nodded. "Yes but you have to know, with the mark comes a great burden. Some would call it a great cost."

Dean tucked away Ruby's knife, "Yeah, well, spare me the warning label. You had me at 'kill the bitch'." In that moment, there was no question what Dean needed and it was that mark…no matter the cost. He needed Cain's Mark in order for him to use the First Blade, the only weapon that could kill Abaddon.

"Good luck Dean." The hunter and the knight shook hands, "You're gonna need it."

"Yeah, I get that a lot. Let's dance." Dean proclaimed while squeezing Cain's hand.

Cain quickly changed the position so that they were gripping each other's forearms before he started transferring the mark to Dean. Dark red veins emerged from Cain's mark before they spread to cross over onto Dean's arm until it stopped on the same spot where Cain's mark had been placed.

Without all the craziness with the demons, Dean couldn't help but rethink Cain's warning. He needed answers. While Crowley seemed to know about the mark (based off his reaction to it earlier), Dean didn't know whether he could truly trust any story that the demon spun on him. Sam and Castiel would have been his next options but he and Sam weren't talking at the moment and Castiel was sticking with Sam to make sure that he healed up properly. With him being on the outs with Sam at the moment, that meant that Dean didn't have access to the Bunker and its archives. It was like when Sam was at Stanford all those years ago when Dean had to hunt alone.

Seeing no other option, Dean took out his phone and clicked speed dial #7.

The phone rang twice before it was picked up. "Hey Dean," a perky voice greeted him instantly.

Dean snickered a bit for her perkiness, "Hey Fee. I need you to look something up for me."

There was a small pause between them when he didn't say anything further. He truly didn't know how to break it to her.

"Alright but did you get him?" She broke the silence instead with the simple acceptance.

Dean sighed. "I got a little side-tracked."

"Hence the research," She filled in before he could elaborate. He didn't bother though, he knew that she'd have something to say and she didn't disappoint. "Quick question but how does one get side-tracked from hunting down the man that killed Kevin and who had threatened to kill Sam? I mean the moment I was able to track down Gadreel's first vessel, you took off to catch him and now you're telling me that you got side-tracked." Once she got started, there was no stopping her. It was a quirk of hers that was both amusing and annoying.

Dean sighed, "Fee."

"I mean that isn't like you Dean," She continued, as if she hadn't heard him, "If you have a trail, you stick to it until you have exhausted every possibility there is to achieve your end goal and even aft-"

"Felicity," Dean cut in firmly. He knew that she meant well yet it wasn't the time.

Felicity sighed, "Sorry. I'll stop. What'd you need?"

"I need you to dig up everything you can find on Cain." He ran a tired hand through his hair, just waiting for the questions to start up again (which was reasonable for what he was asking).

"Cain?"

He hummed. Wait for it.

"As in Cain and Abel?"

He hummed again yet he could hear that her breathing had picked up.

"As in the Cain you are supposedly descended from?" Her voice squeaked a bit.

The hunter groaned at that bit of information; he had forgotten that fact since Michael had told him that a long time ago. "Supposedly, yes."

Her breathing picked up again, "As in the very man who committed the first human murder by killing his own brother?" She squeaked some more yet he could tell that she was on the verge of hysteria.

"Felicity, listing every known association with Cain isn't going to change the fact that I need more information on the guy!" He blurted out before she thought of another statement to throw at him.

Felicity sighed as she concentrated on calming down; he did have a point. "I know that but why Cain? For all we know he could be another myth."

"He's not." He mumbled yet he didn't say anything else. He took the time to get into Impala as his exhaustion was starting to hit him now.

"That's it," Her disbelief was evident to him, "You're not gonna tell me anything else?"

"Not over the phone."

"Right," He could hear a few fast clicks of a keyboard from her end, "When should I be expecting you then?" She was all professional again, which he respected. They could get informal with one another later.

Dean looked at the dashboard before he did a mental calculation in his head, "Is two hours good enough?" He wasn't that far away from Starling City thanks to Crowley. The demon had transported them and the impala to an isolated dock along the California coast so that Dean wasn't far when Crowley had to go searching for the First Blade.

"For me to find anything?" Felicity scoffed, "Get real but you can tell me all about it while we wait."

Dean chuckled, "Sounds fair."

The goodbyes were brief before the hunter hung up and started the engine. He had a rendezvous to make with the blonde IT girl and he didn't want to disappoint.

*SPN*Arrow*SPN*Arrow*SPN*

Felicity sighed as she placed her cell on her desk. It truly was going to be a long night for her. Thankfully, they just finished with a case so Oliver was just going to patrol the streets of Starling City.

She had only planned on verifying the Mirakuru cases with inconsistencies with Officer Daley's activity while Oliver was on patrol yet Dean had given her a challenge she didn't think she'd ever receive.

She never thought that she'd be doing research on the man that was nicknamed the Father of Murder.

It was a really good thing that Felicity was alone when she answered Dean's call. There was just no way she could have lied to Oliver if he had overheard that call…her rambles would have exposed her before she knew it was happening.

Felicity exhaled deeply as she got comfortable at her workstation.

She had a deadline to meet.

*SPN*Arrow*SPN*Arrow*SPN*

A/N #1: And there you have it! What'd you think? I know its rough but this was just stuck in my head after 9x11/2x11 aired. In my head, Felicity has worked with the Winchesters before (think of her as another Charlie Bradbury, a female hacker that they befriended after a case). I could turn this into a multi-chapter later on...it's a possibility I'm not against but what do you think? Please leave a review!

FYI: Next THREE chapters aren't as Supernatural-centric as this one. They will be Felicity-centric.

Originally Published (in "A Moment In Time"): January 24, 2014 (Happy 35th Birthday Dean Winchester!)
Originally Published (in "Mysterious Smoak"): March 1, 2014 (Happy 36th Birthday Jensen Ackles!)