"There's nothing I can do now. That was our last chance." John sighed as he spoke to Dean through the prison phone. He looked into his son's eyes through the bullet proof glass that separated them.

Prison guards watched the exchange carefully. They were understandably suspicious of the two men whispering into the phones.

"What now?"

"You're gonna need a lawyer and a bloody good one at that."

"Do you know anyone like that?" Desperately, he questioned his father.

"Well, I have heard about this one kid..."

Dean blanched, "A kid?"

"Yeah, he's young but Bobby was talking about him the other day as though he'd walked on water. Apparently he got some hunters outta trouble a few weeks back. Did a real good job about it too..."

Dean frowned causing a thin crease to form in his tanned brow, "So he's a Hunter?"

John shook his head and tried to remember the details from the conversation he had with his old friend about two weeks ago. The memory was foggy but he grappled with facts for his only son.

"Nah, he's a lawyer but knows all about the life and helps Hunters out when he can. A kinda thanks for the work we do sorta thing, I think."

Dean nodded but couldn't help feel sorry for this young man who had gotten himself sucked into a life where he knew about what lurked in the dark. He didn't want to pull him any further in but he knew he needed someone good to get him out of the prison.

"How good?"

"Standford University. Top of his class. Really good." John said quickly like he was trying to seal a risky deal.

"Sure. I'll take him." Dean grinned mischievously.

"That's of he'll take you, boy!" The elder hunter chuckled lightly but Dean could see the concern that was poorly masked in his father's eyes.

Dean fiddled nervously where he sat. This was the deciding meeting; the kid got to choose whether he wanted Dean as a client. From the emails John had been getting from the lawyer, it seemed almost certain that Sam Wesson was going to take his case but he still didn't want to risk it.

The room he had been placed in was dull and grey. The walls, table, chair, ceiling and floor were a boring cement grey. It lacked any personality and made Dean bored as he leant back on the plastic chair while he waited.

His eyes stuck to the hands of a plain white clock that sat high on the wall as his possible lawyer's arrival time came and went. After a little while, Dean was beginning to feel like he'd been stood up when suddenly, a tall man stumbled into the room in a sharp suit.

Top lawyer? Dean mumbled to himself as his eyes scanned the seemingly chaotic man, Doesn't look that way to me...

The lawyer had long brown hair which framed the strong features on his face. His hazel eyes sparkled with mischief and the guy was way taller than Dean himself. The Hunter had to admit that his guy was definitely his type. If they hadn't been meeting like this then maybe he would have asked him out for a few drinks and maybe would try to spend a night with the man. Unfortunately for him, he was in prison so that wasn't exactly what he should be thinking. After all, the man might even be straight.

The man straightened his tie and flattened out his wind swept hair to make himself presentable even though first impressions had already been formed.

The tall man strode over to the Hunter with the confidence of a lion on the prowl. It made Dean slightly uncomfortable. Usually he was the one with the confidence not whoever he was meeting.

"Mr Winchester?"

"I was last time I checked." The lawyer raised an eyebrow at the sassy confidence of the man in front of him.

"Very confident for a man in cuffs, Mr Winchester." He smirked and slightly hoped that his client didn't recognise the mild flirtatious tone. That would be undeniably unprofessional of the young lawyer.

Dean smiled slightly as he craned his head back to look at his lawyer. His eyes drank in the strong jaw line and sharp suit with a light smirk, "Yes, but do you think you can help me?"

Sam placed a cocky smile onto his lips, "I believe I can, Mr Winchester."

"How the f-"

"Dean." His father scolded as the young men went to swear while a couple of kids rushed by. A dirty look was shot at Dean from the protective mother.

"No, I'm serious. How the hell did he manage that?" The younger Winchester stood dumbstruck outside the courthouse in his poshest dark navy suit.

"I don't know. After hearing the prosecution's argument I was certain you were a gonna." John answered honestly.

The wind blew against the men as the stood awkwardly at the bottom of the large steps that lead up to the court. The sun was out but there was still a sharp chill in the breeze making Dean shiver. This really wasn't what he had planned for his first few hours of freedom but he supposed he would make do, especially if it allowed him to see his lawyer again. He hoped not for the last time.

"Where is he?" Dean mumbled under his breath effectively breaking the silence.

His father shrugged slightly, "Getting some papers or something. I wasn't really payin' attention when he told me. I just said we'd meet him here."

It was only a few moments later that the heavy doors burst open to reveal Sam practically running down towards them with a smile. His briefcase was in one hand while the other arm was full of lose sheets, creating quite a weight in the man's arms.

He opened his mouth to speak when Dean cut over the top, "How the hell did you manage that? Even the judge seemed shocked at his fast you turned it around."

A deep blush grew on his cheeks and he peered down at his shiny dress shoes, embarrassed, "I... don't know. I just did the research, I suppose."

"You did good, son." John gave him a firm pat on the shoulder making Sam jolt.

After congratulating him, John strode off toward the Impala leaving Sam and Dean alone. They stood awkwardly for a moment before Dean steeled himself and turned to face the lawyer. Sam seemed hesitant to meet his eyes as though he didn't want this to be the last time he saw him.

"Hey... If you wanted, you could give me your number... And we could meet up for drinks some time?" Dean rubbed the back of his neck, "I mean, you got me off a life sentence so I owe you something."

They both knew that the invitation to drinks wasn't just thanks; Dean really liked Sam and there was no hiding that fact. Sam had also grown to like his client so now they were no longer working together, they technically could meet up whenever.

"Yeah, I'd love that." Sam said with a shy smile making Dean's stomach flip.

Unsurprisingly, they did meet up and Dean even found himself taking hunts within a few hours drive of Sam so he could visit the man. Neither of them wanted to give up their jobs so they made a compromise, they'd take it in turns to meet every few weeks to spend a few days together. A long distance relationship was hard but they made it work for them.

Needless to say, Sam kind of became the Winchester's personal lawyer and got them out of several tricky spots in the next few years.