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Sam gets a call from Bobby; he’s found where they are keeping Anna Milton, in a hospital guarded by an army of demons. When the brothers arrive they find themselves surrounded. With Ruby by their side they fight their way in and barricade the door with salt. Tied to a chair in the middle of the room is a scared young woman with blood red hair hanging over her face, soaking wet from being dumped repeatedly in water. She doesn’t even dare lift her head when the boys enter, she is too terrified. Standing over her is the ring leader. Dean stops dead in his tracks- it’s Alastair. Frozen on the spot Dean looks intently into Alastair’s dark black eyes. From here he can see the dark pit, a never-ending portal to agony and bloodshed and hear the screaming of the hundreds of souls he and Alastair tortured in Hell, all begging for mercy.    

 

Alastair smiles playfully and circles Anna menacingly brandishing a knife, slicing her arm demanding to know what the angels are planning. The petrified Anna musters what little courage she has and tells the black eyed man “No!” Alastair retaliates with “Not the answer I was looking for cherry pie” and cuts the knife deep into her chest, making her cry out in pain.

 

“That’s enough!” Dean yells. Alastair smiles at his Hell buddy and welcomes him to his fun house. “Dean Winchester. Good to see you again. Come and join in the fun. This one’s bound to spill her guts after a few minutes alone with you”.

“Dean, what’s he talking about?” Sam asks his brother confused but Dean can’t look Sam in the face; he turns away trying to stop the memories from flooding back.

“It’s inevitable Dean. Remember all the fun we had down there? We were a regular Depp and Burton. Weren't we Dean?”

 

Dean turns back and demands “Let her go Alastair. She doesn’t know anything!”

“Oh but she does, don’t you cherry pie…” he assures. He licks Anna’s blood from the blade. “Mmm, tastes like cherries”, Alastair laughs.  “I can taste it in her blood. She knows what the angels are planning; she can provide us with the intel we need to win this war. Just needs a little incentive to make her talk”.

 

Anna looks up into Dean’s eyes and whispers “Help me! Please.”