September 25th 2016

"Jesus, Dean. You look…terrible. What happened?" Sam asked as his older brother took a seat across from him at the large, circular table.

Dean's left eye was completely swollen shut and he had long purple and blue bruises scattered down both of his arms, the ugly marks clashing violently with the orange jumpsuit he was wearing.

He looked as though he hadn't slept in days and his good eye was bloodshot.

"Good to see you too, Sammy," Dean retorted sarcastically before throwing an agitated look over his shoulder at the guard standing directly behind him. "Seriously, dude? Can I at least talk to my brother without you breathing down my fucking neck?" he asked, surprised but relieved when the man actually took a couple steps back.

"…Well?" Sam huffed impatiently once Dean's attention was solely on him. "What happened? Did that Alastair guy do this to you?" the younger boy inquired, his fists clenching as a feeling of rage began to bubble up in his chest.

"It's not a big deal, Samantha. I'm in prison, not daycare. Fights happen," Dean jeered as he leaned forward, resting his battered forearms on the cool metal surface of the table.

However, even though Dean was trying to play it off as nothing, his feud with Alastair went far beyond just two men with a disdain for each other.

Alastair wanted Dean.

He wanted him for a number of reasons. He wanted to own Dean, to break him. To make the younger man his bitch.

But Dean would be damned if he'd EVER let that happen. He'd rather die.

Not that he would admit any of that to Sam. Besides, telling Sam about Alastair's intentions would only make him worry, and that was the last thing Dean wanted. It was his job to worry about Sam, not the other way around. Dean was Sam's big brother and he would protect him at all costs. Even if it was detrimental to his own situation.

"…Dean…Just be careful, please?" Sam begged, tears brimming around the corners of his eyes.

And the sight nearly broke Dean's heart into a million pieces. This was the first time in three weeks that he'd see his baby brother and not five minutes into their visit, Sam was already crying over him.

Son of a bitch.

"Sammy, careful is my middle name," Dean teased in an attempt to lighten the mood, flashing his younger brother an award winning smile.

"You're a fucking idiot," Sam shot back, earning a scowl from Dean.

"Hey, watch your mouth. I can't imagine aunt Ellen lets you talk like that," the older man grumbled.

"….I'm sixteen, asshole. I can curse whether aunt Ellen let's me or not. And don't act like you didn't do your fair share of cursing when you were my age," Sam said defensively. "…Besides, I don't use that kind of language in front of her…"

"Ha! That's what I thought, you little bitch. She'd tan your hide if she heard you talking like that," Dean taunted, smiling genuinely for the first time in what seemed like forever. "How you doing there, by the way? Living with two chicks driving you crazy?" he asked suddenly.

Ellen Harvelle, although she wasn't Dean and Sam's actual aunt, had been a good friend of Mary Winchester's and was the closest thing they had to a mother since their own had passed away.

And when Dean was arrested in July for armed robbery and assault, with an illegal possession of narcotics charge to boot, Ellen had not hesitated to take Sam in and raise him as her own.

"Actually, it's not that bad," Sam confessed with a little chuckle. "Jo's a bathroom hog but besides that, it's nice living with them. Jo's kinda like the big sister I never wanted."

"Hey, don't get too comfortable, dude. I wouldn't wanna have to fight Ellen's only daughter for the title of best sibling," Dean joked, the smile fading from his face when Sam scoffed.

"Don't be ridiculous, Dean. I'm moving back in with you as soon as you get out. I love Ellen and Jo, but you're my family and you're the best brother anyone could have," Sam told him earnestly, the younger boy's declaration causing Dean to blush.

"Jesus, Sammy. Enough with the chick flick crap. Seriously, if I were you, I wouldn't be so excited to go back to living with the dude that can't even afford to buy a house where you can have your own room. I bet you're sleeping in a warm, comfortable bed and eating home cooked meals every night at Ellen's. That's a huge set up from crashing on my ratty-ass couch and trying not to cry every time you see Ramen or a peanut butter sandwich. Why would you wanna come back to live with me?" Dean asked, cringing when his younger brother's eyes saddened, a hurt look appearing on his face.

"Because you're my brother and it's us against the world, remember? I don't care if we live in a cardboard box and eat cat food. At least we'll be together," Sam said with conviction.

Beaming with pride, Dean nodded his agreement as he silently thanked any deity that was listening for having such a great brother like Sam. It was extremely comforting to know that even if everyone else in his life abandoned him, Sam never would. No matter what happened.

"So, you excited for junior year?" Dean asked, desperate to get away from all the touchy, feely shit Sam had brought up.

He was so not in the mood for feelings.

At one point in time, Castiel might have been able to force that sentimental garbage out of Dean…but not anymore.

Castiel had broken up with him five months prior and since then, Dean had bottled up every little emotion he felt out of self-defense.

He knew it was wrong, and he knew it wasn't healthy, but Dean couldn't help it. He had lost the love of his life because of his self-destructive nature and that feeling of emptiness had almost killed him.

That was why, after a short stretch of drinking at all hours of the day and fucking anything that moved, Dean decided to put his heart on lockdown. Making a promise to himself that he'd never love anyone the way he loved Castiel again. That he would never allow himself to be that open and vulnerable with another person.

"As excited as a person can be about school, I guess," Sam replied, snapping Dean back to reality.

"Oh shut up, ya nerd. Don't pretend you aren't thrilled," the older man teased.

"Dude, whatever. How are you?" Sam asked all of a sudden, catching his big brother off guard. "How you talked to Ellen? Or…dad? …Castiel…said he sent you a letter about a month back…"

"I got it," Dean mumbled, looking down at the table. "…I just…I can't open it, okay Sam?"

"Dean, just…talk to him…He misses you…" Sam sighed, giving Dean his best set of puppy dog eyes.

"…Really? Well, isn't that funny. Cause he didn't seem too interested in talking to me when I was breathing fresh air," Dean gritted out.

"Don't even go there, Dean. Don't you dare act like Castiel wasn't justified for avoiding you after you guys broke up…You were out of fucking control, dude. And he stuck around and put up with so much of your shit for a ridiculously long time…He even accepted the fact that you hunt without trying to have you committed," Sam seethed, his voice low enough so the guard behind Dean couldn't hear him.

Narrowing his eyes at Sam, Dean let out a frustrated huff but didn't argue. Honestly, he couldn't. Sam was right, as much as Dean hated to admit it. He had pushed Castiel too far, given him no other choice but to break up with him.

After Dean had dropped out of high school, he had felt utterly lost. All of his friends had abandoned him and Dean's father had cut all ties with him. Not to mention, he and John had fought a long, brutal custody battle for Sam and when Dean finally won, he fucked that up too.

As it turned out, raising Sam on his lowly salary from the garage was near impossible and after months of putting his brother to bed hungry, Dean decided to do something drastic.

Cue him getting mixed up with the wrong crowd and eventually starting to knock over fancy houses when the owners weren't home.

Hey, it had been good, easy money and Dean honestly couldn't say he felt bad robbing those rich assholes.

But that wasn't the only stupid thing he had gotten into.

Along with convincing him to burglarize private property, Dean's new friends also introduced him to the wonders of popping prescription drugs. And in no time, thanks largely in part to his addictive personality, Dean became hooked on Vicodin and Oxycodone.

Which was why, after months of arguing, and a couple pretty nasty physical altercations, Castiel finally called their relationship quits. And Dean hadn't blamed him one fucking bit. Despite the fact that it hurt like hell to know that he'd driven the only person he'd ever loved to the edge like that.

And just five months later, when he had reached rock fucking bottom, Dean had been arrested for breaking into a house just outside of Anderson. The assault charge he was facing had been thrown into the mix because he was forced to defend himself against the owner, who had stumbled in on him trying to steal his big screen TV.

Dean had ended up breaking the guy's nose, but because he was an idiot and decided to get high before he went out that night, he was unable to make a clean getaway and voila, here he was. Serving an eight month prison sentence and forced to do some fucked up shit to feed his addiction.

Honestly, Dean gave a whole new meaning to the phrase, "how the mighty have fallen." He'd gone from Anderson's golden boy to it's biggest disgrace in less than a blink of an eye. And he'd lost everything. His father, his brother, his friends...and his fiancé.

"…You're right, Sammy…I just…I can't talk to him, man. And I want you to tell him to stop writing me," Dean blurted out, causing Sam's jaw to fall open in shock.

"Dean," Sam began but stopped short when Dean raised his hands dismissively.

"I want him to move on, Sammy. I don't want him to spend one fucking second thinking about me…let alone setting aside time to write me a letter while I'm locked up for something he told me was going to come back to bite me in the ass. He deserves to find someone who will treat him right, who isn't so consumed by his pride to love him the way he deserves to be loved. I want him to have a great life in California with a respectable boyfriend, to spend time with his friends and party…to just be a normal college kid….Please…just tell him to forget about me…" Dean begged, hating that his voice had cracked more than once during his speech.

"…Jesus Christ, Dean…Why can't you just accept that you were good enough for him? He didn't want some storybook romance…Castiel just wanted to be with you. For almost two years I watched the way you two depended on each other, the way you loved each other. I just don't understand why you're so willing to let something so special go," Sam confessed, sounding far wiser than any sixteen year old Dean had ever met.

"…Because…I'm a fuck up, Sam. I don't deserve someone as good as Castiel Novak. I never did," Dean sighed, receiving a murderous look from his younger brother.

However, before Sam could rip him a new one, the guard behind Dean announced that his visiting hours were over.

"…I'll…tell him to stop writing to you, Dean…but know that I think you're the biggest idiot God ever put on this earth," Sam groused as his brother and he stood up in tandem.

"Well, you can take comfort in the fact that you aren't the only one," Dean snorted before giving Sam a warm smile. "…It was good to see you, man…I'm glad you came by..."

"Yeah, you too…I miss you," Sam replied, his voice almost a whisper.

Clearing his throat, Dean avoided eye contact with his brother, feeling the guard's a hand wrap around his left bicep, trying to usher him away.

"Tell Ellen and Jo I said hi, okay? I'll see ya soon, Sammy," Dean called out to Sam as he made his way back to the massive steel door that led into the prison.

"…See ya…Jerk," Sam shouted, his eyes filling with tears again at the sight of Dean being herded back to the hellhole from whence he came.

"Bitch!" Dean chuckled, giving his brother one last playful grin over his shoulder before he was pushed through the doorway and out of sight.

Taking a deep breath, the happy expression on Dean's face disappeared, replaced with a scowl as he mentally prepared himself to be thrown back into the mix with robbers, murderers, and thugs. All of them wanting nothing more than to break his will.