Disclaimer: I own nothing, John Snow. I don't own that reference either.

Warning: mentions of homosexuality and sex tapes. Not beta-ed. And I don't really know how the whole jail thing actually works, so there might be some inaccuracies.

Pairing: Pre-Sabriel, Pre-Destiel.

Summary: Sam gets arrested and finds himself spending the night with a cellmate.

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Sam Winchester sighed as he was led to his cell. His brother Dean was gonna be so pissed when Jody calls him. On the bright side, he'd managed to erase that awful sex tape that Ruby was using to blackmail him. Too bad her nosy neighbours had thought he was a thief and called the police. According to Jody, he was to spend the night in a cell, waiting to know if Ruby would get him out. She would deal with her the next morning, but she couldn't let him go at the moment, not when he had been caught in the act. Sam didn't keep his hopes up, though. Soon, she would find out that her blackmailing tool was gone and she would press charges out of spite. If she had the slightest chance to hurt him, you could bet she would take it.

"You're getting company after all, Mr Novak!" said the deputy.

That's when Sam noticed there was a man in the cell. He was short, with light brown hair and golden eyes. A smirk appeared on his face when he noticed them.

"So nice of you. Here I was, thinking I was to spend the night alone and you bring me a little friend!"

Sam snorted at being called "little", being 6'4" and definitely taller than him, but said nothing. The man seemed sober and in a good mood. Sam thought he could have landed with a way worse cellmate. The deputy opened the cell, gestured for him to get in, closed it and left, leaving Sam alone with "Mr Novak".

The man stared at him a moment before getting up, offering his hand. "It seems that we're to spend the night together… In a way. So we might as well try and enjoy ourselves. Let's start with introductions. I'm Gabriel Novak and I'm here because the deputy can't take a joke. What about you, kiddo?"

Sam smiled and shook the man's hand. "Sam Winchester. Nice to meet you. And I'm here because my ex girlfriend is a bitch."

Gabriel chuckled. "Ex girlfriends always are. What did yours do?"

Sam sighed and ran his hand through his hair. "That's kind of a long story."

Gabriel shrugged. "We've got all night."

Sam hesitated. He was reluctant to tell this to a stranger but somehow, Gabriel seemed trustworthy. The man was almost radiating kindness and warmth. Besides, Sam was probably already screwed anyway and the odds were they'd never meet again. He nodded and went to sit on the only bed in the cell. "True. OK. I was dating this girl, Ruby. It was fine until I found out I was gay and broke up with her. She got really mad at me and threatened to post a sex tape we had done a few months ago on the Internet. I tried to talk her out of it, saying it could ruin my career, but she wouldn't listen. I didn't know what to do, so I… I kind of broke into her house to delete it. I figured that if the sex tape was gone, she might leave me alone. But her neighbour heard me getting in and called the police. They caught me on my way out. Now I'm waiting to know if she's gonna press charges."

Gabriel's eyebrows rose but he didn't laugh at him. "Sounds like quite a bitch indeed."

Sam felt relieved that Gabriel was not making fun of him or making lewd innuendos about him making a sex tape. He allowed himself a small smile. "Tell me about it."

Gabriel went to sit next to him. "I know what it's like to deal with an angry ex-girlfriend. My last one, Kali, actually tried to stab me."

Sam smirked. "Let me guess, she couldn't take a joke."

Sam wondered a second if it wasn't too rude of him, but Gabriel laughed. "You're funny, kid. I like you. But no. She too went nuts when I broke up with her. She said my brothers were turning me against her. To be fair, they were not overly fond of her, but that might have something to do with her sleeping with my best friend."

"Sorry to hear that."

"Don't be. One of my brothers, Lucifer, really hated her guts so he was more than happy to help me kick her out. Plus, it really is her loss. Speaking from experience, Baldur is terrible in bed."

Sam blushed a little when Gabriel winked at him and tried to subtly change the topic. "Lucifer? Is that your brother's real name?"

A knowing smile from Gabriel taught Sam it wasn't that subtle but he went with it. "Yep. All named after angels. Family tradition. First there are the false twins, Lucifer and Michael. Then Raphael, me and my little brother Castiel. You'll probably meet him, he's the one who usually gets me out of trouble."

"And I guess you'll meet Dean, my big brother. He's gonna be so pissed when Jody calls him. And when he hears it's because of a sex tape, he's gonna laugh his ass off. I'll never live this down!"

"Well he's the older brother, it's his job to be a pain in the ass. If something like that happened to Cassie, I'd tease him about it for years."

"Yet he keeps getting you out of trouble?"

"He's used to it. Actually he might even think that this is just an elaborate ruse not to go and meet this "awesome guy, really you'll love him" that Lucifer found God-knows-where. Like I can't find my own dates."

"Why don't you tell him you're not interested, then?"

"He's an awesome big brother, but he kinda lives up to his name. And there's this stupid ten year reunion I have to go to next week and I just can't face Kali without a gorgeous boy toy on my arm. So Luci's offer doesn't seem like such a bad deal after all."

Sam smiled. "Maybe he can arrange another date?"

After a few seconds of silence, Sam turned to Gabriel, only to find him staring at him with a thoughtful face. Sam frowned. "What is it?"

Gabriel seemed to hesitate a moment but eventually asked: "Do you have plans for next Saturday?"

"No, why? Wait, you want me to go with you?"

"I said I needed a gorgeous boy toy and you, my friend, look like a damn underwear model."

Sam blushed. "You've known me for less than ten minutes."

"What can I say, I have a thing for dimples."

Sam rolled his eyes. "And when people will ask where we met, you're just gonna tell them we were cellmates the previous week?"

"Why not? It's kinda badass. It might even keep Kali from trying to stab me again. Bonus."

Sam chuckled. "This is a moot point anyway since I'll be in jail."

Gabriel smirked. "Not if your ex-girlfriend says it was a mistake or something."

"Why would she do that?"

Gabriel looked thoughtful for a moment. "Ruby, right? Not a very common name. Luci mentioned a Ruby once. They used to steal cars together. She works for Michael's company now. I wonder if it's the same girl."

Sam shrugged. "That's possible. She works for an insurance company."

Gabriel grinned. "Novak Insurance?"

"Yeah." Realization dawned on Sam's face. "Oh. Of course. Your big brother Michael is Michael Novak."

"Yep. You know, I don't think she wrote car stealing on her resume and Michael might not be happy if the criminal past of one of his employees was to get public. He might even have to fire her."

"Are you suggesting I blackmail her?"

"No, I'm suggesting you give her a piece of her own medicine."

"It's felony."

"I call it justice. You know, what goes around comes around. Listen, I'm not telling you to ruin her life or anything, just let her think that you're ready to do so."

Sam smiled sadly. "She'll never buy it. She knows I'd never be able to do that."

Gabriel smirked. "Of course she does. You look like a puppy. No one would believe you'd hurt anyone."

Sam faked an offended look. "A puppy? What happened to the underwear model thing?"

Gabriel grinned. "I don't know, take your shirt off so I can be sure."

Sam laughed and threw him the pillow.

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They spent the rest of the night talking about their brothers, their job and everything they could think of. Sam told Gabriel he graduated from Stanford to become a lawyer and his brother Dean was a mechanic. Gabriel told Sam about Lucifer's bar, the Devil's Trap, and how Lucifer and Michael would bicker endlessly about everything but still team up and be terrifying when it came to their brothers' well-being. Gabriel would flirt shamelessly, of course, and keep trying to get Sam to come with him to his ten year reunion by promising candy, booze and not to much PDA ("Though if you wanna put out, it's fine by me, gorgeous!"). Sam would laugh it off, saying he wasn't that eager to meet his homicidal ex-girlfriend and there was no way he would put out without a proper date first anyway. They talked and laughed for hours, until they heard someone call "Sammy?"

Sam frowned. "Dean? Is that you?"

Dean appeared in the corridor with Jody. "What the hell did you do, man? Jody called, telling me you broke into Ruby's home?"

Gabriel chuckled. "Well this is gonna get awkward…"

Dean glared at the other man. "Mind your own business, short stack!"

Before Gabriel could snap back, Jody piped in. "Gabriel Novak. What bird name did you call the deputy this time?"

Gabriel faked an offended look. "I did no such thing!"

"Sure. Listen, I just got here with Dean but Deputy Kripke told me your brother should be here to get you out any minute now. In the meantime, Sam, I can't let you out yet. I'll talk to Ruby and see if I can make her say it was some kind of joke between you two so we can pretend nothing ever happened. If she doesn't want to, I'll try to get you released on bail as soon as possible. But you'll have to stay here until I can talk to her."

"Yeah I was expecting it. Sorry again to have bothered you on your day off. And thanks for calling Dean."

"Don't worry about it, I'm glad you called me. You only interrupted a Back from the Future marathon anyway. I'll leave you guys for now and come back when Castiel arrives."

Dean snorted. "Castiel? What kind of name is that?"

Gabriel smirked. "You'll know soon enough."

"Yeah, whatever. God, Sammy, what am I supposed to tell your boss? Hell, what am I supposed to tell Bobby?"

Sam snorted. "Maybe you should let Jody handle Bobby. As for my boss, if I'm still in here on Monday morning, we'll think of something."

Dean looked like he was about to rant again, but the noise of the door opening cut him. Jody was back with a black-haired man wearing a trench coat.

Gabriel got up. "That's my ride, boys. Hello, Cassie."

"Cassie" rolled his eyes. "Hello Gabriel. Stop calling me "Cassie"." He said in a deep voice while Jody was letting Gabriel out.

"You boys take your time, I'll be in the next room if you need anything."

They thanked Jody and she left. Sam smiled at Castiel and offered his hand through the bars. "Hi, I'm Sam and this is my brother Dean. It's nice to meet you, your brother talks a lot about you."

Castiel shook his hand and turned to Dean. That's when Sam noticed Dean was wide-eyed and blushing lightly. That was unusual.

"Hi, I'm Dean. Castiel, right? That's an interesting name."

Gabriel and Sam exchanged a knowing look, remembering Dean's earlier comment on the name. Castiel just stared at Dean with impossibly blue eyes.

"It's an angel name."

"Oh. Suits you well…"

Castiel frowned slightly and tilted his head on the side. Dean cleared his throat. "I mean, since you're rescuing your brother from jail."

"I guess you're doing so yourself."

Dean smiled. "Well that's what big brothers are for."

Sam shook his head, smiling. Dean had gone into flirting mode. Gabriel seemed to have noticed too. He backed away slowly, getting closer to Sam and whispered. "Looks like Dean-o here is quite smitten. And he seems to be Cassie's type. Is he gay and single?"

Sam whispered back. "We never really talked about it, but he's brought men home before and he's tired of one-night stands. I don't think he has a type, but your brother really looks good so…"

Gabriel punched him in the arm. "Hey! No hitting on my baby brother, you're my date not his!"

Sam only chuckled. Gabriel looked thoughtful for a moment, which Sam thought meant nothing good for his brother. "You mentioned he was a mechanic, right?"

"Yes?" Sam answered, wondering where he was going with this.

Gabriel handed his cell to Sam. "I'm gonna need the address. Cassie's car is about to need fixing."

It took Sam a few seconds and seeing Gabriel's smirk to understand what the man had in mind. He took the cell, raising an eyebrow. "You're gonna sabotage his car?"

"It's for a good cause! Cassie will be happy, your brother will be happy and I'll get to spend more time with you, which will make me happy too!"

"You heard what Jody said. Looks like if you want to spend more time with me, you'll have to visit me in jail."

Gabriel smiled. "Oh yeah, Ruby. You let me handle her. I won't let you rot in here, we have plans for next Saturday, remember?"

"I didn't say "yes", you know."

"You will eventually. You like me."

Sam rolled his eyes but didn't answer. He did like Gabriel. He was sweet and funny and cute and… Yeah, he liked him. He wasn't exactly enthusiastic about meeting his potentially homicidal ex girlfriend but he did want to see him again.

"Besides, you didn't say "no" either. Means I still have my chances, right?"

"I'll think about it. Here's the garage's address."

"And don't forget your digits."

Sam chuckled and typed his name and phone number.

"Great. Guess I'll see you in a week, then. Come on, Cassie, stop flirting start moving!"

Castiel blushed profusely and quickly said goodbye to Dean before almost running out of the sheriff station with his brother.

Dean turned to Sam, a big smile on his face. "Do you think we'll see them again? I mean, I'm not sure I like this Gabriel dude but he seems to have been a decent cellmate. And Cas looks… interesting."

Sam chuckled. Cas, really? "I'm sure you'll see him again very soon."

Dean's grin grew even wider. "Awesome. Hum, yeah, so, wanna tell me why you broke into Ruby's home?"

"Not really, no."

Dean ran his hand through his hair in frustration. "I mean, come on, man, I thought you wanted to stay away from her!"

"I did, I just had no other choice."

"Go ahead, spill."

Sam sighed, knowing his brother wouldn't let it go. "She had a sex tape, okay? And she threatened to post it online. I could have been fired because of that, so I went to her place to delete it."

Dean burst out laughing. "Really, Sammy? You? A sex tape?"

Sam shot his brother his biggest bitch face ever. "It's not funny, Dean."

"I'm sorry, it's just… Well I didn't expect something so kinky from you. I guess I can throw away that purity ring I got you for your birthday…"

"Jerk."

"Bitch."

Sam raised an eyebrow. Dean understood the double meaning of his favourite comeback and sobered up at the speed of light. "Yeah, sorry. So what now?"

"You heard Jody. There's nothing we can do but wait for Ruby to make up her mind."

"Maybe I should talk to her."

"No. I mean it, Dean. I don't want you near her. It's only gonna make things worse anyway."

Dean had never looked so frustrated in his life. "Come on, Sammy, what do you want me to do? You're my brother, I can't leave you here and do nothing about it!"

"You have to. Trust me, everything's gonna be fine. Jody will do everything she can but in the meantime, we have to wait."

"Fine. I have to go to work, but I'll bring you dinner tonight if you're not out yet. Call me if anything happens, okay?"

"Sure. Oh, by the way, Castiel is single, so if you see him again, feel free to ask him out."

Dean turned crimson. "I don't know what you're talking about, dude."

Sam laughed as Dean all but ran out.

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Later that day, Jody called with the news that Ruby had told the police it was just a big misunderstanding and all charges against him had been dropped. Sam kept wondering all day if Gabriel had something to do with it. Ruby was tough and Gabriel looked sweet but Sam had a feeling that his cheeky grin and eyes full of mischief were only the tip of the iceberg. And Ruby wouldn't lie to the police to save him out of her good heart when she was the one who tried to ruin his life in the beginning. Something or someone had made her change her mind and he doubted Jody had this kind of influence on people. He went home and took a shower, smiling to himself while thinking about the short man. When he got out of the bathroom, drying his hair with a towel, he noticed his cell indicated a new text.

"Luci and I had a little chat with this Ruby girl. She won't bother you again. Ever. G."

Sam smiled. He hadn't spent more than a few hours with the guy, yet he felt he really liked him. And Gabriel obviously liked him back. Sure he needed someone for his ten year reunion, but he went to blackmail a woman to get a total stranger out of jail. No one could be that desperate for a date, there had to be something more. He thought about it a few seconds. It was probably crazy but…

"What time do we have to be at your high school reunion?"

"Knew you wouldn't let me down, Samsquatch! 9. Pick you up at 8?"

"Make it 7, I'm buying you dinner first."

"It's a date ;)"

Sam grinned. He then texted Dean to let him know everything was fine, thinking that maybe, given the consequences, making that sex tape was actually worth the trouble.

His phone beeped again: "Awesome. What does my porn star of a brother wants for dinner? ;)"

Okay, maybe not.

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The end! So, this is my first Supernatural fic. I wanted to try an AU and, well, coffee shop AU is already taken by another pairing I'm working on, so... Seriously, I just liked the idea of them meeting in jail for stupid reasons. So don't hesitate to tell me what you thought about it, and point out any mistake I might have missed. And by the way, this is an OS but I'm working on a sequel. It will be about the date and feature Kali, Baldur and Lucifer.