Dean eyes a luscious girl at the bar intent on scoring. Sam huffs and reminds Dean they are on a case. Dean doesn’t listen to Sam and goes over to talk to the girl. Within minutes she’s on his arm and they’re heading for the door; Sam shakes his head in contempt, another notch on Dean’s belt.

 

Back at the motel room Dean and the girl get straight down to it. They kiss and head straight for the bed, hands all over each other. Dean opens his eyes to find himself chained to the wall, the room sinks away into darkness and he cries out into silence. Demon Alastair appears by Dean’s side and offers him a proposition “Join me and you just might actually survive down here”. Dean is about to tell the demon where he can stick it but he is cut off by the sound of his own screaming. An unseen force rips through his body like a knife, he can feel his insides burning as he struggles to get free. There is no end to his agony. Alastair asks him again. This time Dean has no choice but to say yes, and with that the chains fall from the wall and he is free. He looks the sinister demon square in the eye and says “What did you have in mind?”

 

“Hey, are you okay?” the girl asks. Dean is on the floor, he’d been crying out in pain.

“Y… Yeah, fine. Just a stomach ache, but I’m fine”. They get back down to it once Dean reassures her he’s fit to carry on and before they make it to the bed he finds himself in Hell again, this time he is the one doing the torturing. A faceless victim is on their knees in front of him begging for mercy and Alastair cheers Dean on as he hits the poor soul again and again; not showing any sign of relenting.

 

He hits his victim again and is brought back to reality when the girl falls to the floor clutching the cheek Dean just struck. Tears form in her eyes and she tries to scramble across the floor away from him, fearing he will strike her again. Dean, having realized what he has done goes over to her but she cries out in fear. She manages to get away from him and runs out of the door, but not before calling Dean a monster.

 

When Sam gets back to the motel room he finds his brother sitting alone in the darkness his head in his hands. “What, another one bites the dust?” he jokes. Sam sees Dean shaking on the bed and goes over to console him. “Dean. Dean? Hey, are you okay?” but Dean doesn't answer, just looks at his hands; a smear of the girl’s blood has painted his hand a scarlet red. He washes and washes but the stain won’t come off, almost like a permanent reminder of the pain he’s caused. Dean stares at his own reflection in the bathroom mirror. He used to see the dry shell of the man he was before his time in Hell and now, all he sees looking back are the eyes of a killer.

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.”

Dean tries to fight his memories of down under but they wash over him like a rapid wave. He remembers the carnage he saw, tortured souls drowning in an ocean of pain. All those times he’s sent demons back to Hell seem insignificant as they are all here now joining

the precession of demons lining up to get a piece of the legendary Dean Winchester.

 

Sam takes charge of the situation and instructs Ruby to protect Anna while he distracts Alastair. Dean and Ruby watch in both amazement and horror as little Sammy Winchester exerts such enormous power, extracting each of Alastair’s minions from their hosts’ bodies. The battle between powerful demon and powerful human erupts into an explosion of blinding white light. The Winchesters, Ruby and Anna all flee the scene in the Impala while an angry Alastair watches through the window, as they drive off into the distance. He smiles a conniving smile knowing full well the battle raging on in Dean’s head will aid him in retrieving Anna once more.

 

Strapped in a web of chains Dean wakes to see he is in Hell. Moments ago hellhounds were ripping him apart limb from limb and now he is helpless suspended in the air, crying out for Sam. He eyes an unknown soul in the distance being prodded with an iron poker and is deafened by his screams. Welcome to Hell. Dean closes his eyes and pictures Sam’s face, this was the moment he realized he was really doomed.

Screams echo in the abysmal chasm; souls burning in torment. The older Winchester doesn’t scream, he can’t; his voice is hoarse from the weeks of anguish he has suffered since he arrived. Would you want to be sent to a prison where half the inmates were put there by you? By now Dean has felt the answer to this question a thousand times over and they show no signs of stopping. Another jolt of electrifying heat cascades through his body, ripping at his soul. Alastair is feeling particularly peppy this morning, must have been the hundred souls that he beleaguered last night. Dean feels his body about to give up when out of the darkness a light shines. The screams fade, the fire blows out and the cool breeze of hope brushes against his face. It’s Sam. That oversized puppy eyed younger brother has marched into Hell itself to free his battered and beaten older brother. Dean can’t even muster a thank you but Sam can see the gratitude in his eyes. He cuts his brother down and helps him walk. Just as Dean manages a smile of hope it diminishes in a flash, as the pain of a thousand screaming souls strikes white hot through his heart. Sam pulls the knife out of his brother’s bleeding chest and laughs hysterically.

“Gotcha” announces Alastair as he pulls Dean’s limp body away into the darkness for some more fun. Dean’s one hope, his last glimpse of Sam saving him is gone. He accepts this as his destiny and breaks into silent tears. 

 

Anna thanks the brothers and Ruby profusely for saving her life, but the battle is far from won. Sam asks the timid girl how she came to possess such a wondrous gift. She explains how she merely awoke one morning to the sound of an angel commuting with another in her ear. Like most people those around her thought she was crazy and she was sent to Riverview. The doctors tried everything to help her, from psychology to electroshock therapy. Eventually she stopped talking about it and they let her be; but once the new doctor arrived claiming he could make her better that’s when the voices became unbearable. This new doctor claimed he could cure her of these voices but all that he brought her was more pain and grief. One night while she was asleep in her bed the alarms blared and the emergency lights flashed. All the patients and doctors now harboured pitch black eyes and then the torturing began.