A/N: This was written after a conversation with my friend about how Alastair may have ended up in hell since all Demons started out as humans. Anyway I got bored and wrote this.
I have no ownership of the boys, or Supernatural that pleasure goes to Eric Kripke, lucky bastard!
Alastair hadn't always been a demon; he'd once been human, like all the other demons had, even if they had forgotten that fact. Some made deals for fame and fortune, others for talent, some for family and love, my point is that humans made deals for a multitude of reasons. Very few remember what Alastair was like as a human, I doubt he remembers either, but I do, of course I remember that whelp. All my other crossroad demons were busy when the summoning ritual called upon one of us, since I was the only one left who wasn't busy, it was up to me to go topside and make yet another deal. I was the king of the crossroads and yet I actually had to work, I remember there was a time when all I had to do was send the hell hounds to collect the miserable souls of those deal makers, but I had to go make this bloody deal. I possessed the nearest guy in a suit (or the equivalent in them days, I suppose it was a suit of sorts) and transported myself to the crossroads. Back in those days it was commonplace to see a carriage or two, there certainly were no cars, and they were about a hundred years away from invention. So I turned up at the crossroads and what do I see before me? A snivelling wretch of a man, it was hard to believe he worked in torture chambers during the day, but perhaps I was biased in my opinion since the only humans I'd personally met were those damned hunters who kept sending my employees back to hell, what I'd have given to have them put on the rack, to make them squeal and squirm and scream while their flesh was flayed from their bodies, while their muscles melted from their bones, while they were carved into until nothing was left. Then they'd have their just deserts wouldn't they. Anyway back to Alastair, he was tall for the time and had a rather impressive beard, it even managed to beat mine from when I was human and making my deal for a few extra inches below the belt.
"Who might you be?" Alastair had asked his voice nasally, rather like his usual meat suit, I sometimes wondered if that voice is purely Alastair or the meat suit or perhaps even a mixture of the two.
"The name's Crowley, good sir and you called a crossroads demon, instead you got me. The organ grinder rather than the monkey." I had almost rolled my eyes at him as I spoke, but that may have just pissed him off and where would I have been without his deal so I could take soul? That's right nowhere.
"I always thought crossroad demons were women." Alastair had floundered, a part of me wondered if he was stalling, trying to back me into a devil's trap, but he didn't have the resolve of a hunter so I was safe.
"Mostly yes, but the king of the crossroads can't exactly go around cavorting as a woman, now can he? Just imagine what that would do for his reputation. Besides I hold the power when it comes to deals my friend, I can change the time allowed before tax day comes due, well I can extend from the usual ten years, but all of us crossroad demons can reduce right down to instantaneous death, actually that's all demons too." Sure I had waffled, but I had always been proud and perhaps a tad vain when it came to my prowess as a crossroads demon.
"You can make a deal for my soul?" He asked and I swear I could have slapped him; this guy was far too slow to survive. How did the human race ever progress with bumbling idiots like the human Alastair in charge of crime and punishment?
"Yes. Just name your terms and I shall name mine." I was patient with the man; the first rule of deal making was to be patient.
"I want to please women in bed. I want to take any woman I want and make her scream." Of all the things I'd heard people make deals for this had to be the strangest I'd taken over as king of the crossroads, you see back then there was apothecaries with drugs that could have helped his little problem, but I suppose he was embarrassed to he had erectile problems to the local apothecarist, so anyway I suppose a deal was the next option. Of course I took pity on the man, I understood, had I not after all made a deal to be bigger below the belt?
"I can improve your performance; in return I shall send my pets to collect your soul in ten years. If you try to wriggle out of your deal, your problems will return and you shall be mocked by women for all your days." I replied setting out my terms.
"Deal. How do we seal this deal?" this bit was always interesting, seeing grown men quiver when they had to kiss another man, it was my own version of torture, the only I truly enjoyed. You see I always used people's prejudices against them myself and it always worked a treat.
"we kiss my friend no-one will hear about this, you won't see me for about ten years, you see if you die before those years are up and I hold the contract for your soul, you'll be coming down quicker than you first thought." I answered, feeling my meat suit's lips morph into a smirk. As expected Alastair cringed, but as desperate as he was, he placated me with a kiss and the deal was done. I kept watch over him after that, he was by far my favourite customer and the women he slept with, they were all beautiful, some were simple whores, others belong to other men as wives. In the ten years he lived after the deal was made, I do believe he had around four thousand women, one every night, sometimes even two. Then his bill came due and how ironic it would be that the hell hounds would drag him to hell while he was making his last woman scream. He lasted long enough on the rack to become hardened and less like the weak sap I'd met topside, but like all souls he broke and jumped from the rack in favour of picking up a blade. I used to watch him torture and often wonder if the look of pure concentration and bliss that I often say on his face was the same look he'd worn when he'd tortured on the surface. Before hell he'd made women scream in bed, but in hell? He made men and women scream on the rack, he had such creativity when it came to blade work. Patterns I'd never seen before were carved into the flesh of the souls. After that I'd realised humans are twisted folk who live for lust and the other sins, but will punish others for those sins just as readily. Personally I never liked hell, but Alastair loved it, I never quite figured out why.
"So you're telling me Picasso with a knife made a deal because he couldn't get it up?" Dean Winchester roared with laughter, okay I admit I had soft spot for the Winchesters and telling them about Alastair showed that, but let's keep this between our selves shall we? Not all hunters were dicks, actually surviving hell, leaving and still hunting could mellow a person out, besides what was an unlikely friendship without a mutual goal? To kill Dick Roman. Dean and Sam Winchester hate Dick as do I. Leviathans can kiss my sulphuric arse. And that is where I leave you now with Leather Jacket rolling on the floor laughing and giraffe just shaking his head and me? Well I have deals to make, stupid crossroad demons to punish and hell hounds to unleash. Promise me something human? Tis alliance between me and the Winchesters will be our secret yes?