Alice was digging into the particulars of Dean's contract. Since all contracts had to be run by Lucifer first, he allowed her to read through it to find any sort of loophole.
After far too many hours, an ungodly amount of coffee, and no end of frustration, she had to admit whoever wrote this had made damn sure her brother didn't escape hell.
It was after her umpteenth attempt that a thought occurred to her. She double checked, before she went to run it by Lilith.
Lilith...looked entirely too amused at her thought process.
"While there is no way for Dean to escape hell, there is no stipulation on where he ends up once he's here."
"So if I were to put my brother's souls into escrow on the condition they made a demon deal and would go down rather than up..." she asked.
"Then when Dean dies, he avoids Alistair's section entirely," said Lilith. "Hell, you could insure he lands near my daughter's little hotel if you were so inclined. I know Alastor has taken up residence there."
Alice was practically vibrating, as she was already coming up with all sorts of ways to screw over heaven and certain factions of hell.
"Can you help me get it in writing? Once I explain things I'm sure they won't think twice about signing it."
"Of course, this is too entertaining not to be part of," said Lilith with dark glee. The fact it would piss off her fake, more so.
When Alice returned to her brothers, they were going to investigate something odd.
"So good news and bad news," said Alice.
"What's the bad?" asked Sam.
"There's no way Dean's getting out of his contract or going to hell," said Alice flatly.
"What's the good then?"
"There's nothing stipulating where you land once you're there," said Alice. "I've checked and rechecked that thing so many damn times that I almost missed it."
Both of them stared at her.
"The guy I call 'boss' let me look at Dean's contract, since all contracts have to go by him at some point."
Dean looked at his sister. Unlike his father, he knew the lengths Alice would go to to keep them safe, even if it put her at odds with hunters. She was also ridiculously protective of Bobby.
"Do we want to know?"
"It would make things rather awkward if you did, at least at this stage," she admitted. "Let's just say it has something to do with my birth dad and leave it at that."
"Fair enough," said Dean. "So what's the loophole exactly?"
Alice whipped out a pair of contracts, handing the first one to Sam.
Sam took it and skimmed at first, before his eyes widened and he started reading it properly.
"Sammy?"
"You want to take our souls in escrow?" he said incredulous.
Alice winced at the tone.
"Long story short, if Dean dies today and ends up in Hell, he's likely to end up in the nonexistent mercies of Hell's top torture specialist Alistair. And he's had plenty of centuries to become very creative at breaking people."
Dean winced at that.
"And if I signed this?"
"You'll end up someplace on the Pride ring, and will likely slip past Alistair's radar long enough to reach a safe area. Or relatively safe for hell anyway."
Both brothers looked at her incredulous.
"What? Lucifer's daughter has it in her head that she can 'redeem' souls so she started this hotel on the Pride ring! Sinners can go there and hopefully receive enough therapy that they can be 'redeemed' enough to go to heaven. Not that any of have successfully completed a treatment plan yet..." said Alice defensively.
"You have to be shitting me," said Dean.
Alice pulled out her hellphone and a video of Charlie's advert on that rather unfortunate attempt to attract new applicants. Sam and Dean watched the video with increased disbelief.
"So I sign this, and I just have to find this hotel and stay put?" asked Dean.
"You get free overdue therapy and a place to stay," said Alice. "So long as you at least try to redeem yourself back into heaven's graces, they won't kick you out and it's protected by a powerful backer from what I was told."
The fact she apparently looked like a smaller, female version of Alastor was sure to surprise Dean.
Dean looked at the contract, then at his sister.
"You got a pen I can use?" he asked seriously.
He'd rather trust his eternal soul to someone he knew wouldn't screw him over than anyone in hell. Alice handed him her special pen, and Dean signed the contract without hesitation.
Sam looked at his own.
"Do you mind if I read this first?" he asked.
"Sure," said Alice. "I had someone help me do a bit of fine tuning to make sure it stuck. Also, if anything happens and either of you end up in heaven properly to the point you're not coming back, I'll rip up the contracts myself."
It had been a week, and Alice was twitching when she saw Dean.
"Dean, I love you and all, but I swear to god if you don't stop playing Heat of the Moment at full blast I will switch every cassette tape in the car to something from the boy band era."
Dean had an odd look on his face. Sam, more so.
"Oh thank god. You noticed it too?" said Sam with open relief.
"Noticed what?" said Dean.
"We're being put through our own rendition of Groundhog Day, only it resets every time you end up dead...usually in ridiculous ways," said Sam. "I've been trying to find if it's the Mystery Spot or what..."
"It's not. That's just a cheap gimmick for bored tourists," said Alice.
Sam looked relieved, as he was starting to go a little crazy over this. Finding out Alice knew something was up made him feel considerably better.
"Tell you what, how about I go with you to the diner this time? I'll take a different table and see if I can spot anything amiss."
It took all of five seconds for Alice to find the source and come up with a plan of attack. Sam was bewildered at first, seeing his sister confront what he thought was a random stranger...until he saw the sheer amount of sugar the guy had for his breakfast.
He put two and two together and became very pissed off.
Outside the diner...
Loki was giving Alice some very weird looks, especially since it was clear that she knew the Winchesters.
"So...when did you two morons start hanging out with demons?"
Dean and Sam looked at each other, then at Loki.
"What are you talking about?" said Dean confused.
Loki gave a pointed look to Alice.
"So, which one of these two morons are you shacking up with? My money's on the moose."
Alice, Dean and Sam immediately developed near identical expressions of disgust and wanting to hurl at the thought.
"You honestly think I'm sleeping with them?" she said, looking openly nauseous at the idea.
"She's our sister, you asshole," said Dean.
Loki looked at them all incredulous.
"Sister?"
"Why are you repeatedly killing Dean and then forcing Sam to remember?" she demanding, changing the subject.
"Just trying to hammer it in to the two idiots there's no saving Dean from his contract," said Loki cheerfully.
"We know that already," said Sam annoyed. "Alice went and asked her boss to read a copy of the contract and said there's no way to keep Dean from going to hell or asking for an extension. That's why she made a second contract that put Dean's soul into escrow, so he doesn't go near the racks."
Loki's amusement died instantly.
"What?" he said shocked. "Wait, hold up. You made a crossroads deal, and then thought it was a brilliant idea to sell your soul twice?"
"Can you think of a better way to screw over heaven and hell by basically holding the souls of Righteous man and Lucifer's supposed vessel?" deadpanned Alice. "My boss and his wife were rather annoyed once they found out who my brother's were and were more than happy to tell me that particular piece of nonsense."
Loki stared at her in open disbelief. Alice never let her smile waiver, as she knew they had caught this jerk completely flatfooted.
"I have a question...why didn't you notice her sooner?" asked Sam. "She's been here this entire time."
Loki blinked.
"Wait. She's been here the entire week I've had you two trapped?" he said.
"Sam only figured out I remembered everything when I threatened to hide all of Dean's music if he didn't stop playing that damn song on the radio at full blast every morning," confirmed Alice.
All three wake up in their cheap motel rooms. Only this time the song was different. Closer inspection revealed it's the next day.
Alice walked over to her brother's room.
"Sam, I'll get the car ready. You make sure Dean doesn't end up dead again, and we'll get the hell out of here before that trickster does anything else," said Alice. Sam nodded.
They managed to make it to the next town without anything happening. Sam and Alice watched Dean like a hawk for a week though.
"So...demon?" said Dean. Now that they were sure Loki wasn't going to try and off him again, they decided to have this overdue discussion. Bobby immediately gave Alice an odd look.
"Cambion, actually," said Alice. "Found out by accident when I discovered that hellphone and summoned up a portal to hell. Apparently it's really, really rare for one to actually make it to adulthood."
"What's a cambion?" asked Sam.
"Half demon, half human," said Bobby. "Not much about them besides that."
"For good reason. From what Lilith...the real one, not the fake Ruby works with...told me, cambions are much, much more powerful than demons. To the point angels openly fear them," said Alice. "From what little she was able to find out, someone with a work visa they never used got summoned by mistake and made a deal that resulted in me being born. Then some hunter mistook my mother for a witch and killed her a year later, which is when mom found and adopted me."
"Work visa?" said Dean incredulous.
"Sinners aren't supposed to be able to go topside, and the angels undergo an annual purge once a year of hell to downsize the number of souls Lucifer has access to. So for those who have the ability to make deals, they can apply for a 'work visa' of sorts that allows them to be summoned in specific areas, mostly crossroads," explained Alice with a shrug.
"...In a weird way, that makes perfect sense," said Sam. "Especially considering what we learned about Ruby."
"So what, exactly, do you do in hell anyway?" asked Dean. Because that had been bugging him.
Alice's face twitched.
"Remember that portal to hell that opened a couple years ago, thanks to Azazel?" she asked.
"Hard to forget, considering that's why I made a deal," said Dean slowly.
"Well, my boss was pretty damn pissed so many lesser demons and the seven sins got loose without permission. Attention means hunters, hunters means heaven has to take note of what's going on and that means that Lucifer gets bitched at by his ex-family members over not keeping them in hell. Lilith tells me where to find the ones that got out and I do my part in sending them back exactly where they belong," said Alice.
"...So basically you're a demon hunter hired by the actual Lilith," said Sam slowly.
Alice nodded.
"So what does that mean for us?" said Dean.
"Not much really. We'd go after demons regardless, just means we have a bit more to work with in regards to hunts," shrugged Alice.
That and Lilith had laughed for an hour straight once she got the full story of how Alastor sired a cambion in the first place. Apparently a voodoo priestess summoned him by accident, and he left a portion of his power in her to get her pregnant rather than actually sleeping with her. He forgot all about the matter until Lilith came around asking questions.
He still hadn't met Alice, but he was aware the child had survived.