After the car accident in the last book, Dean wakes up in the hospital but later finds out that he is on the verge of death. He realizes that he is wandering around the hospital as a spirit, but later finds out that Akuma, the new found half-demon, is also 'stuck' in this veil. Dean unleashes his very angry thoughts about Akuma and tells her that she needs to leave or else she will get everyone killed. Akuma takes off at the first chance possible, however Dean is unaware of the danger that he is already in. A reaper has been wandering around the hospital killing people and Dean is next on her list. Dean's new friend Tessa is then revealed as the very thing that his hunting him and he is about ready to give up his life and move on. Though at the same time John Winchester has just done the unthinkable, selling his soul to the very demon that he has been hunting for the last fifteen years, all in order to save his son from the too close for comfort death. Once Dean is awake and very much alive, he finds out that Akuma has snuck away and left them all behind, though he can't remember anything from when he was in the veil, other than a pretty girl named Tessa. Alice at the time discovered the now past John and then her missing sister. Sam and Dean are deeply upset that their recently reunited father is now dead and they think that he did the worst thing possible and dealt with the devil to save his son. Alice, however still sad for the brothers, is pissed to the max at her sister's departure. And this sends her into a downwards spiral of drinking and rage.
While the boys and Alice stayed together as hunters to take down monsters with more ease and also to ensure that Alice doesn't become too destructive, Akuma spends time with her (still unnamed) demonic uncle, healing from her wounds before she began training to take down her father. During this time Alice is getting more and more pissed off and the boys are trying their best to help, especially Sam who had secretly gotten Ash start tracking down possible places that Akuma could be. One night Alice has a terrible nightmare and Sam is there to help, bringing emotions bubbling to the surface for both of them. Sam gets word about a hunt up in Canada that leads to them staying in a gorgeous old farm house that Alice's father handed down to her before he was killed. Dean and Sam are shocked and pleasantly surprised at the place and Dean nearly deems it his dream house. The three are finally reunited with Akuma when they go to take down a nest of vampires and werewolves. To say the least they are surprised, especially at finding Akuma pinned beneath a wolf who is working hard at trying to tear her apart. One of the boys shot the wolf in the shoulder and Akuma finished it off by stabbing it through the skull with a silver knife. When Alice finally realizes who it is she launched herself at her sister. After a short fight the boys separate them and Akuma admits that she left because Dean told her to, a fact that shocks all three of them, including Dean.
The team takes some time up in Canada to deal with a case and camp out at the girl's farm house, later revealing that the house is seen as the most perfect dream house that the boys could ever imagine. Realizing that it's Akuma's birthday Alice and Sam wake up early to make her a breakfast cake, knowing that Akuma would be pissed, Alice was more than happy to fuel the fire, though it also happens to be Halloween, which means costumes. By this point Sam and Alice had somewhat secretly been dating and that means that Alice wanted to have matching costumes. As a joke, and for the whole idea of being a couple, Alice dressed up as an angel and Sam as the devil. Dean had put on a makeshift renaissance king's guard outfit, and to everyone's surprise Akuma had dressed up as the most slutty cowgirl that she could. If Alice was going to celebrate Akuma's birthday, which she hated because of her father, then Akuma was going to at least get drunk and laid. After a small rival at the bar between Alice and Akuma, Alice drags Sam out to dance and then later back to the farmhouse to share the night with each other, though nothing happened as they were way too tired and drunk. On the other hand, Akuma was plastered and Dean had dragged her off the table and out to the car. He was so done with babysitting Akuma's drunken, slutty, dancing ass. That and he was slightly jealous of all the guys that she was giving her attention to. Once in the car a very drunk and very horny Akuma makes a last minute to decision to give Dean a blowjob, and to his surprise he enjoyed it, and was probably the best he's ever had. This was not going to be the last of their sexual encounters.
Shortly after the team experiences an encounter with a djinn, only to find the both Akuma and Dean had been tricked and succumbed to his power. In the dream world Akuma and Dean are happily married with a child on the way, the dream life that perhaps both of them so desperately want. Still the question arises, does Dean have feelings for Akuma, and does she feel the same? It seems that way in the dream world, where Akuma is accepting this new life as reality where Dean knows it all to be some massive hallucination and they need to get out as soon as possible. Dean, not knowing what else to do and at his lowest point, stabs himself and dies. Only to wake up in the real world, his world, tied to a chair. Alice and Sam come to save the day, but a very heartbroken Akuma kills the djinn and enters a state of silence.
After the fiasco with the Djinn, Sam and Alice finally get a chance to themselves and actually confess their feelings for each other and that their relationship is more than just a connection. Sam, afraid that he might not get the chance to tell, or rather show Alice just how he feels - after seeing how the djinn's fantasy world had affect both Dean and Akuma - he takes a chance and Alice is just as willing to reciprocate her feelings, and with that they make love for the first time, not sex, but love.
When the team gets a new hunt, and a very terrifying vision of Dean from Sam's dreams, they all run down to investigate, leading them to an almost empty town, with a few crazed townspeople who desperately want to spread a violent disease. Looking back into John's journal Sam figures that it has something to do with Croatoan, in which he's not wrong. They end up locked in a hospital with a possible victim, the one that Sam had seen in his vision. Though he was not infected, the nurse was and attacked Sam, bleeding on his wound, also getting Alice and Akuma, though Dean stayed clean. After a long wait and blood tests it determined that Sam and Akuma were virus free, although Alice on the other hand was experiencing a major turn of events. Though she did not have the virus, her body had sent her into a fit of shock as it attempted to heal itself at a very fast speed, something that no one has seen before. As the team leaves, a single demon stayed behind to catalogue the events, noting that Akuma and Sam were immune, as expected, though a new discovery was found when Alice also fought off the infection. Leading yellow eyes, the man behind the virus, to wonder what, or who Alice really was. This whole fiasco leads Akuma to a very disturbing dream with her father, one in which suggests that her and Sam are to be destined together to rule Hell. Her father also suggests that Sam is not exactly normal, he is supernatural just like Akuma. Which leads her to think that her father had done something to Sam to change him, to make him different. It's only then that she puts some of the pieces together. She confronts Dean with what she suspects and he reveals to her that John had told him something before he died. Something that has been bothering Dean for months, she convinces him to talk to Sam about what's been going on and finally reveals the secret that Sam is not exactly normal, that if he can't save Sam, then he will have to kill him. This pushes everyone's relationships to the limit as new feelings and information are being brought up and tossed around.
The intense feelings that have shared between Akuma and Dean are now being stressed to the max after a very drunk Akuma gives Dean the best blow job he's ever recieved, but that's not where it ends. Dean has been having second thoughts about the ways he's been feeling about Akuma and with the tricksters crazy sex dreams and the life never had with the djinn, Dean and Akuma find themselves having a drinking contest. Which ends in his favour as they again, drunkenly make out on New Year's Eve and eventually leading to a night of hot sex and a plethora of hickeys and bruises. While Dean, very interested in taking their relationship to the next level, finally realizing that he has feelings for Akuma, she doesn't feel the same way (that she wants him to think, as she doesn't want to get even more attached) turns him down. Leading to a very grumpy and slightly heartbroken Dean to drive Alice and Sam to the store to get some groceries and a very much needed pie. Which leads us to the most recent event, Sam and Alice have been kidnapped by the yellow eyed demon, Akuma's father, and has let all his other psychic children on the loose to kill or be killed in the mess that Alice and Sam are smack dab in the middle of. Consequently, Jake fatally stabs Sam in the back after knocking Alice to the ground hard enough to give her a severe concussion, which actually caused the voices that were once cluttering her mind to come back, all screaming her name and for her to get up. Akuma catches the falling Sam and cradles him in her arms until Dean takes her place. Akuma sees her father fleeing from the scene and ends up cracking the earth beneath her, realizing that now... Sam is dead, her sister is severely injured, and Dean is brotherless and heartbroken.
What will they do now?