Hi guys,
So this is a filler chapter to dive a little deeper. I thought it might be interesting to see what would happen if Dean told Sam who Callie was and this was the result. I have skipped a few episodes which I will do quite often as I don't want this story to be over 100 chapters long (it may still be that long) let me know what you think

Wicked.

It had been five months. Five months since he had seen or spoken to her. They had battled Demons and myths and skin walkers which made him fear from Callie's life and of course the bugs. Oh man the bugs. He shuddered. That was not a fun case. He looked bac down at the number again. He didn't need the paper he knew it off by heart. Had it really been five months of continuous wondering of what if? What if he had stayed there? What if he had admitted to her who he was? What if she remembered him? What if? He was staring at his phone and the piece of paper he had kept in his pocket for the last five months. He had called her once, twice but had lost his nerve every time. Sammy was getting suspicious about the whole thing. He'd try to open up a conversation about it but Dean was having none of it and slowly Sam had dropped it. He felt bad lying to his little brother but he just really didn't want to open that can of worms. Sam would demand Dean to do something brave and righteous and wouldn't understand why.

"So now do you wanna explain?" Speak of the devil. Dean sighed and put the paper away.
"Explain what Sammy?"
"Your strange fascination with Callie?"
"I don't have a fascination with her!" Dean weakly protested.

"Dean seriously, ever since you've seen her you've been like obsessing over her. I mean I get it she gorgeous but..."

"Don't say that." Dean gritted.
"What? She is!" Sam smirked knowing this might answer his questions. Dean never got defensive when Sam complimented his other conquests. "You've seen her in those shorts. She has a fantastic body that makes you just wanna..." Dean stood up from the table and stepped towards the bed where Sam sat, drawing on a pad of paper.

"Don't you dare say that Sam!" he barked.
"Why not? She is just a chick!" Sam baited.
"She isn't just a chick! She's intelligent and funny and sweet!"
"Dean you knew this chick like what a few days? Suddenly you care about her? What is it about Callie is making you so twisted and wired!"

"She was my Jessica ok?" Dean finally snapped. Silence fell over the brothers. To say Sam was shocked was an understatement.
"What?" Sam felt his jaw drop.
"She was what Jessica was to you to me" Dean sat back at the table and sighed.
"But you only knew her for like four days? And you won't even call her now? How can she…?"
"I knew her years ago. Meet her before you went to college. Got a house together. We were together for years." Dean said softly.
"What happened?" Sam asked the most obvious question.
" I left her." Dean sighed again.
"Why?"
"Doesn't matter. Fact is I left her."

"You loved her?" Sam asked softly, never seeing Dean like this.

"Yeah. So freaking much" He chuckled and rubbed his face.

"What happened?" Sam asked after a few minutes. He couldn't understand. Dean had the girl. He met Callie, she seemed nice and friendly and really cool and…she didn't even acknowledge him? Something was missing.

Dean sighed.

"Dad did"

"What?"

"There was rouge werewolf few years back and it attacked her because it followed me and I led it right to her." The way he said it sounded like he was far away. "I thought I was going to lose her that day. But no, I should have known. She's a tough chick and pulled through. Dad put the thought in my head that I should leave her. That she would be better off. So I paced up after she was completely healed and left." Sam felt so bad for his brother.
"How come she didn't recognise you then?" That was the big question. It sounded like she was involved with Dean for a long time and that she may have known the life they lived so why did they act like strangers?

"I left and 9 months later found out she was attacked. She has no memory of who I am or what we had." Dean looked at Sam and smiled weakly. "She has no idea that we had a home together or anything about this life…nothing." Sam felt his heart break a little for his older brother. How did he do it? It would cripple Sam.

"Dean, man I'm so sorry. I feel like an idiot." He said. Dean raised an eyebrow.
"What? Why?"
""I just invited her along not even asking you man! I was just impressed by how calm she took everything and she seemed really understanding and cool and…and i felt bad about her almost drowning and…"
"Don't stress Sammy. You didn't know." Dean cleared his throat and turned away from his brother.
"Why didn't you tell her?" Sam asked. "She was right there! You could have told her…"
"Told her what Sam? Hey you don't know or remember me but were actually together or at least we were until my father told me to break your heart and leave you which I did. I'm sorry about your memory loss and that its pretty much my fault. I am also sorry that you've been alone the last two years dealing with everything you've gone through with no fucking idea what the hell happened to you and I am sure you're incredibly confused but I am back now so how about it? Let's get back together!" he held out his arms in a sweeping motion. "Oh yeah Sammy that would have gone down so fucking well." Dean rolled his eyes. Sam was stunned. It was the most that he could remember his brother ever talking about how he felt or his anger at himself. He felt deeply saddened and if he knew it wasn't going to end in him getting his arse kicked, he would have hugged Dean. He couldn't understand why Dean didn't jump at the chance to get her back! He would kill for a second chance with Jess.

"It's a second chance Dean! Why don't you take it?" Sam asked.
"It's enough for me to know she is alive and happy. She has a life and she is safe. That's all that matters to me."
"Is that why you still look at her number? You want to call her!"
"Of course I do Sam! I would love nothing more than to call her up and admit that I miss her so much sometimes I feel like I can't breathe! But it won't happen cause she is safe and happy and that is why I will stay away." Dean stood again, clearly agitated.
"But…" Sam tried.
"No Sam! Just drop it okay? No more chick flick moments. What we had was great freaking amazing and yeah I miss her but she doesn't remember. She has another life now and I am happy for her. I got to see again and that's good enough. Just leave it." He marched over to the front door, grabbing his coat on the way.

"How long were you two together for?" Sam asked one last question.
"It would have been six years tomorrow." And with that Dean left. Sam sighed and run his hands over his face. He knew something big had happened between Callie and his brother. Dean never fawned over a chick this long before. Not to mention he had caught him pulling out a peach coloured scarf when Dean thought Sam wasn't looking. It must have been Callie's. Dean must have really loved her. He felt saddened for Dean. He had a chance to get out. To be happy. And instead he ended up with a girlfriend who had no idea who he was. It sucked.

Sam knew he should leave it alone but now he was curious. Maybe he could ask Dean a few more questions…It wouldn't hurt…right?

So what did you think?

Wicked