Bobby should have expected it, he couldn't even die without it becoming more complicated than it needed to be. Or without some jerk coming in to steal his thunder. Rest in peace. Yeah right.
It was Crowley who appeared to make his last moments as uncomfortable as possible.
"Alright salesman of the month," the demon said to the reaper. "On your bike. Bobby Singer is a hunter and they require a little more finesse than your pay grade allows apparently."
"Step aside, demon," the reaper hissed. "It's not your job to reap souls."
"Maybe technically not, but I am the client. Consider this cutting out the middle man. Now scram."
Crowley clicked his fingers and the reaper vanished.
"Hey!" Bobby protested.
Crowley turned to the hunter.
"I'd be offended if I were you. Fancy sending a nitwit like that to reap the great Bobby Singer."
"Damn you, Crowley. I hadn't made up my mind yet!"
"Oh please," Crowley scoffed. "We both know you weren't going to leave those two overgrown basket cases to fend for themselves."
"I prefer the term 'idgits'..." Bobby grumbled.
"Now Bobby," Crowley proceeded, getting back to business. "You find yourself in a rather unique position here. Yes, you're a murderer, daddy, wifey, tut, tut, tut. But you've also done enough to earn yourself a ticket upstairs."
"I thought the whole point of this choice was the uncertainty of the outcome. Heaven or hell. Something or nothing. You know, faith?"
"Well aren't you fortunate that you have friends in high, or rather low, places," Crowley grinned. "Your choice, Bobby. Up, down, or crazy town?"
"Seems like kind of a no brainer," Bobby pointed out. Who would willingly choose hell?
"Lucky for you then," Crowley said, tapping his own forehead in the corresponding spot to Bobby's bullet hole.
Bobby rolled his eyes at the cheap shot. He still had a brain, so what if it was a little scrambled?
"Why on Earth would I not choose heaven?"
"Well here's the thing, Bobby. The fine print that no one bothers to read. Heaven might be nice and all, you know, reliving your happiest memories, hanging out in your favourite places, blah, blah, blah. But what they don't tell you is that it's a prison. Go there and you'll never see those boys again."
"Ever?"
"Nope."
"Right. So what's your counter offer?"
"Very good, Bobby. You're getting the hang of this. What I propose is that you don't stay here and become some mindless spook, you don't go upstairs and confine yourself to that nauseating illusion. You come with me instead."
"To Hell? How dumb do you think I am, Crowley?"
"On the contrary Bobby, I find you to be very intelligent. So here's what I can offer you. Come with me. Put your considerable skills to work as one of my interrogators and in fifty years or so, when your soul is as black as mine, you'll be free to return and possess whoever you like. See your boys again. Hell, even jump back in the fight if you're so inclined."
"Fifty years? I know them boys is idgits and all, but if it takes them fifty years to sort this Big Mouth thing out, I ain't gonna be much help. Besides, they'll be old men by then."
"Bobby, Bobby, Bobby," Crowley said, wrapping an arm around Bobby's shoulders. "My, my, that bullet has scrambled your brain. Hell time, remember? To Sam and Dean, you'll be topside again in less than six months."
"And all I gotta do for you is torture a bunch of souls? That's not nothing, Crowley." Could he do this? He'd spent so long fighting the monsters...
"Evil souls, Bobby. Pedophiles. Rapists. Drunks that terrorise their wives and children. For Sam and Dean. And if you get a kick out of it, well maybe your soul will blacken all the sooner. So what do you say?"
It was a tough choice, but there was only one thing in this whole messed up situation that he was sure of. Sam and Dean needed him.
"Sounds fair," Bobby agreed, holding up a hand when the demon leaned in. "Just as long as I don't have to kiss you again."
AN: I'm thinking this could be the start of a Demon!Bobby series. Maybe check back in a week or so if you're interested in that. Thanks for reading :)