Elena Gilbert, Damon Salvatore, and Matt Honeycutt are on their way to find the gate to the Dark Dimension, where Stefan Salvatore is being held prisoner. Elena and Damon share a kiss, causing their auras to merge, and Elena meets a little boy who is chained to a boulder inside Damon's mind, a symbol of his childhood. An out-of-body experience during a nap allows Elena to visit Stefan in his prison cell. He believes she is a kitsune illusion, but soon realizes it's really Elena. Her teardrops fall on him, restoring some of his strength. On a late July morning, Bonnie McCullough and Meredith Sulez visit Caroline Forbes' house in Fell's Church. Bonnie is disoriented by the interior of the house, which smells of sulfer, and going up the stairs feels like stepping down. Bonnie notes that Caroline is becoming wolf-like. Bonnie and Meredith argue with her when Caroline says she's going to name her twins after "their father," Matt. Caroline suggests the real father, Tyler Smallwood, might be dead. Matt gets the wrong idea about Elena and Damon, and Elena demands that Damon never Influence her or Matt. Matt splits up from Damon and Elena and agrees to meet up with them in Sedona, Arizona. Damon teaches Elena how to circulate Power through her body so that she can regulate her aura and appear as a normal human girl to any supernatural creatures. Damon believes Elena is pushing him away, and obsesses over the "dozens of boys and men" he thinks she has slept with in the past. In their motel room that night, Elena falls asleep and dreams that unseen voices are arguing about a memory that will remain inside of her until "the time is right". She wakes up and confronts Damon. He grabs her and kisses her. Their auras merge and she meets the little boy again. He refers to himself as the "Warden of Secrets." Elena is torn away from him as Damon breaks their kiss, and discovers that she is crying. Elena realizes he's been so distant because her aura is overwhelmingly tempting to him. Damon tastes Elena's tears and realizes the truth: Elena is a virgin. They share an intense moment before Elena allows Damon to drink her blood. The next day, Elena and Damon realize that he doesn't remember the night before because Shinichi is still able to take his memories. When they arrive in Arizona, Damon reveals that Matt went back to Fell's Church immediately after they split up. Bonnie and Meredith arrive, insisting on accompanying Damon and Elena to the Dark Dimension. Meredith wants to find either one of the kitsune twins' star balls, or "hoshi no tama," which will allow them to control the kitsune. Meredith believes Misao may be possessing the girls of Fell's Church. They discuss Elena's feelings for Damon.
Damon drives the girls to a cave in the desert and reveals that unless they pretend to be his slaves, they'll never be allowed into the Dark Dimension. After initially protesting, they follow Damon through the cave, eventually boarding a ferry boat and taking a frightening river journey which causes Bonnie to faint. They dock on the outskirts of an enormous city. Damon explains that sometime during the ferry ride, they made a "twist in space" and are no longer in Earth's Dimension. There is a dim red light over the city, caused by a sun that is perpetually setting, making day and night meaningless. Bonnie goes into a trance and says the city is full of "Shadow Souls." They ride on litters through the city bazaar, where Elena is distraught by the endless poverty and despair surrounding them. In exchange for her lapis ring, Elena is given a starball by a man named John, and experiences a romantic memory from his youth as though she is John. When she comes back to herself, Damon unties the "slave" ropes from Elena's wrists and they kiss. Elena enjoys this until she suddenly pulls away from him, calls him a bastard, and accuses him of Influencing her. Damon denies doing this and explains that star balls record memories, which fade with use, and are entirely lost to the original person. Elena's attention is caught by an angry vampire viciously beating a pregnant woman on a side street. Elena throws herself between the vampire and the woman, using her body as a shield. Elena receives whip lashes across her face and body. Damon kills the woman's vampire master, Old Drohzne. A street urchin named Lakshmi takes them to a nearby doctor named Dr. Kephar Meggar. Elena vows to protect the beaten woman, Ulma, for the rest of her life. Damon and Elena argue about the incident with Old Drohzne and share some Black Magic wine at the doctor's. Damon heals the gash on Elena's cheek with his tongue and kisses her. She offers him her throat, which he refuses. He says that her blood is full of Power which vampires can absorb, and that she should be careful who she lets sample it. They are interrupted by Meredith, who informs them that there is angry mob with torches waiting outside for Damon. Now known as Lady Ulma, the slave woman is extremely grateful to Elena for saving her.
Mostly vampire mob accuses Damon of taking a slave that belongs to Old Drohzne's relatives, then beats him. Thinking he's about to die, he sends out a message to Stefan with a blast of Power, saying that Elena is coming for him. The beating stops when an imposing vampire appears, a huge black dog by his side and a large falcon on his bare shoulder. His name is Sage, and he and Damon have met before. There is some mystery as to Sage's "real" identity.
Damon tells Elena that the slums are ready to revolt unless she is punished for her disobedience. Realizing she can't win a war against the slum lords, she agrees to publicly apologize to the Drohzne family and receive her punishment. Damon promises Elena won't feel a thing during her punishment. Elena is led in front of a crowd of slumlords, street people, and vampires drunk on Black Magic wine. Young Drohzne formally accuses her of stealing his brother's slave, Lady Ulma. Elena pleads guilty and is sentenced to ten lashes. Elena gives a speech, written by Meredith, begging forgiveness from her Master. Damon begins to whip her, keeping his promise that Elena won't feel anything, and she spends the episode thinking about Stefan. The crowd thinks this is a "hypnotist's act." It is now early August in Fell's Church, and Matt and Mrs. Flowers are discussing the actions of the kitsune and the town's children. Matt thinks the meetings are in the Old Wood, which is a very dangerous place. He sneaks out to spy on that evening's meeting. Matt hides in a thicket near the Old Wood, where Sheriff Mossberg is waiting to arrest him for assaulting Caroline. They argue, but are interrupted by the arrival of Shinichi and the town children entering the Old Wood. Sheriff Mossberg's niece, Rebecca, is among them. Matt begs the sheriff to not follow them, but he doesn't listen. An hour later, Shinichi and the children come out of the Old Wood. The sheriff isn't with them. Lady Ulma reveals that there is a secret room full of gems at her family's abandoned estate. Elena, Bonnie, and Meredith decide they should return to the estate to uncover the jewels and restore the property to its proper state. Lady Ulma asks Damon to buy the father of her child, her jeweler father's apprentice, Lucen. Lady Ulma is freed, but Damon is the official lord of the estate. The girls will now masquerade as Damon's courtesans, which requires beautiful dresses and jewelry, provided by the talent Lady Ulma inherited from her clothing designer mother, and their own in-house jewelry designer, Lucen. Lady Ulma and Sage recognize the people mentioned in the clues Misao gave to the twin fox keys' locations as people who happen to be giving parties soon.
The night before the first gala, Elena begins to sob, longing for Stefan, and has an out of body experience. She visits Stefan in prison, where he again thinks she is a kitsune illusion. She lets her tears fall on Stefan, who begs her to stop crying. Stefan asks God for a moment to touch Elena, and she becomes corporeal long enough for a kiss. They discuss how to get Stefan out of prison and Damon's ability to keep his promises. Stefan wonders if Elena keeps her promises. Elena and the others believe the key may be hidden in one of the harps belonging to Lady Fazina Darley, the Silver Nightingale. The gowns Lady Ulma has designed for the girls have been blessed by a priestess to protect the girls from vampires—not including Damon. Lucen presents each girl with matching jewels and a fan. Elena feels that Damon is holding something back from her, and allows him to feed from her. Damon, Elena, Bonnie, and Meredith arrive at Lady Fazina's intimidatingly beautiful mansion. Elena and Damon sit down to await Lady Fazina's concert and are surprised to see Sage appear. Lady Fazina makes her entrance, takes the stage and begins to play her harp and sing so beautifully, Elena and the other guests begin to weep. Meredith suggests looking for the key while everyone is mesmerized by the performance. They enter the Hall of Harpery, which is guarded by a steward at the door. Bonnie, Meredith, and Sage begin to search the harps, Influencing the steward for more information. Damon and Elena search the rest of the palace. The steward has reveals that the harps are tuned every day, so the key can't be in one of them. Elena finally finds one half of the fox key inside a fountain pen. It is a small crescent in the shape of a fox, with alexandrite eyes. Elena explains that after they realized the key wasn't in a musical instrument, she thought of looking for writing instruments. Damon and Elena are so excited to have found the key, they embrace and Damon begins to feed. Elena encounters the little boy in his mind. Damon is taking too much blood, and they yell at him to stop. When he does, Elena sees that his back is covered in bloody cuts—the lashes he channeled away from her when she was Disciplined. She screams and faints. The others attempt to revive her, but Elena refuses to come to until Damon frees the little boy. He denies owning a little boy, and Elena says his name is Damon. Meredith remarks that Elena "was willing to die for a metaphor." On the way to Dr. Meggar's, Elena stops breathing twice. Bonnie donates blood to Elena, and Meredith and some servants donate blood to Damon. Elena isn't allowed to see Damon during her recovery out of fear that she will end up a vampire. Elena protests that there is nothing untoward going on with Damon, but accidentally switches Damon and Stefan's names.
Matt visits the Saitou house. Obaasan tells Matt that taking out a kitsune's tail will enrage it, but also make it weaker. She also tells him a legend about a beautiful kitsune from whom the Saitou family is said to be descended. Obaasan blesses some bullets, writes some amulets for Matt, and on his way out of the house, her daughter, Orime, gives him Post-it note amulets, to be stuck on demons if necessary. Elena begins to plot Stefan's jailbreak. Lakshmi informs her that if she has the key to his cell, she can just go let him out. She wonders why Elena has never gone to visit Stefan, an idea that had not occurred to Elena. Damon immediately makes an appointment to visit Stefan. Matt, Tyrone Alpert, and Mrs. Flowers go to the thicket on the edge of the Old Wood to discover what's become of Sheriff Mossberg. Roping themselves together and covering their arms with enchanted Post-it notes, they get down on the ground and reach blindly into the Old Wood, trying to grab whatever they can without getting pulled in themselves. Tyrone is almost pulled in. A large tree branch falls on Matt's arm, but he is protected by the Post-its. Tyrone retrieves a human femur with teeth marks on it. Matt faints. Damon and Sage discuss the meaning of "Shi no Shi", the name of the prison. Damon thinks it means the "Death of Death," but Sage says it can mean "the new death," "the true death," or "The Gods of Death." Wearing a new outfit of gold tulle and strategically placed jewels designed by Lady Ulma, Elena joins Damon, Sage, and Dr. Meggar, wearing new outfits made of sacking, and they take a carriage to the prison, where Elena notices a dimensional door in the lobby. On the way to Stefan's cell, Elena fears he is dead and almost faints. She is horrified by Stefan's condition when she reaches his dungeon cell, and throws herself against its razor sharp bars. Stefan doesn't recognize them, but he smells Elena's blood. Damon is overwhelmed and runs away, pursued by guards. Dr. Meggar injects Stefan with something that may help him survive for a few days. Dr. Meggar is unable to draw Elena's blood, which she wants to squirt through the bars, feeding Stefan via syringe. A white kitsune in the cell across from Stefan's pantomimes using the same method with Black Magic wine instead, which Elena does. Sage and the guards return, and Elena is dragged away from Stefan. Elena must be supported as they leave the prison. Dr. Meggar says that the injection, Black Magic wine, and willpower should be enough to keep Stefan alive until they can get the fox key and rescue him. In the carriage, Damon asks if Stefan is dead and is shocked to learn all that Elena did for Stefan inside the prison, feeling he has failed his brother.
Before Blouddeuwedd's party, Lucen and Lady Ulma give the girls an overwhelming amount of jewelry, which doubles as currency in case they need to buy their way out of the Dark Dimension. The girls thank Lady Ulma, who thanks Elena again for having saved her and Lucen. They say goodbye to the household. On the way to the party, Meredith and Bonnie discuss Elena's feelings for the Salvatore brothers. They are unsure of exactly who or what Elena wants. Elena and Damon, riding in a separate litter, overhear this conversation and are shaken. Damon says that there is a detail in the story of the brothers killing each other over a girl which everyone has missed. They arrive at the party before Damon can reveal this detail. Elena and company believe the second half of the fox key is hidden in Blouddeuwedd's main ballroom, the Great Ballroom, which is outdoors and larger than a football field. The ground has been rolled smooth so that no one will trip while dancing. Meredith and Bonnie search the upstairs floors while Elena and Damon search the Waltz Room. Lady Bloddeuwedd enters the party, a beautiful girl made of flowers who has been cursed to spend every night from midnight to dawn as an owl. Damon and Elena run into a vampire who witnessed Elena's Discipline—he is the reason they were invited to the party. Damon agrees to perform their "hypnotist's act" after the crowd finds his "amulet"--the other half of the fox key. The guests begin digging up the grounds. Damon carries Elena up a set of clear crystal stairs inside Blouddeuwedd's clear glass house to look for the fox key. They are confronted by Blouddewedd, who informs them that they are in her private library, and refuses to answer their questions. She doesn't like humans or vampires. Damon is offended and asks if she has seen Shinichi or Misao. She calls the kitsune thieves and says she encountered them running out of her house the night the Great Ballroom was rolled over. Elena thinks they dropped the fox key into the Great Ballroom floor. Blouddeuwedd then states that she is going to kill Damon and Elena. Damon and Elena run back outside and meet Meredith, Bonnie, and Sage in the Great Ballroom. Sage's dog, Saber, gets the kitsune's scent from the fox key and begins searching for their trail. Saber indicates that the kitsune were in the hydrangeas under the library window. Sage takes a carriage and follows the trail leading away from the hydrangeas, in case the kitsune can be caught and the key half recovered. Damon and Elena prepare to put on their "hypnotist's act." Elena begs Damon to let her share the pain, so that he doesn't take it all on himself. She then begs Bonnie and Meredith to share the pain of the whipping to further lessen it. During the whipping, Elena overhears spectators whispering about forbidden starball orbs kept in Blouddeuwedd's library. She realizes that the key isn't in the ballroom, but in the starball room, and charges into the house after the whipping is over. Blouddeuwedd is in her library, now in owl form. Elena thinks the fox key is in the owl's nest in the center of the room. Blouddeuwedd threatens to kill Elena. Elena attempts to explain what she's doing, but Blouddeuwedd continues to threaten her. Sage's falcon Talon arrives just as the owl begins to attack. Talon distract Blouddeuwedd by dropping and shattering orbs while Elena searches for the key. Elena finds a metal object in the nest. The giant owl pursues her down the stairs. She falls at the bottom, causing the owl to crash into the glass where she was standing moments before.
Saber leads Sage and some party guests along the carriage route taken by the kitsune. They come to a crossroads, where Saber loses the scent, due to a local perfumery blinding his nose. Sage picks a random direction, and Saber picks up the scent again. Saber leads the party up to a run down building, and Sage breaks down the door. Back at the party, Elena gets out of the house and puts the two halves of the key together. They become a ring. Damon finds Elena, Bonnie, and Meredith just in time to save them from another attack from the giant owl. Elena tells Damon they have to leave immediately and that she never wants to come back. Damon attempts to fight Blouddeuwedd with a huge shard of glass, putting out one of her eyes. He thwarts her attempt to carry off a random guest. Elena tells him telepathically that she has the key and that he can come with her or not, but she is leaving now. Sage returns, and Elena, Meredith, Bonnie, and Damon all take his carriage to the prison. Sage has pillowcases full of star balls in the carriage, which he looted from the run down building. They abandon the carriage to the giant owl's attacks. Elena and Bonnie make their way to the prison, desperately fending off Blouddeuwedd's attacks with pieces of glass and wood held over their heads. Damon catches up to them and protects Elena from another attack. At the prison, Stefan is in very bad shape, and thinks Elena is a kitsune illusion. She uses the fox key to open his cell and allows Stefan to feed from her as he is carried out on a makeshift litter. Elena realizes that Blouddeuwedd will kill everyone, and is able to produce her Wings of Protection. They wrap around herself and her friends, and Blouddeuwedd crashes into them, killing herself. Just before they leave through the Dimensional Door, the white kitsune appears, giving Stefan a bouquet of flowers sealed with amulets.
Matt and Mrs. Flowers are awakened by a loud noise and rays of light outside the "bunker" room they've taken refuge in at the boardinghouse. They discover Elena and her companions. Suddenly, Shinichi's face rises from the ground, a huge, frightening illusion. He taunts them, saying they are keeping secrets from each other. Meredith is examining what she thinks is Misao's starball, when she is suddenly attacked by grass that constricts and traps her. Elena demands Shinichi let Meredith go in exchange for the starball, but then Stefan is engulfed by deadly grass, too. Damon tells Shinichi to take the starball.Mrs. Flowers and Matt charge out with the enchanted Post-it notes, covering Meredith and Stefan with them. The grass dies away and they are freed. Shinichi continues to taunt them, but disappears when Damon shoots the illusion-face with blessed bullets. The next morning, Damon is up early, wondering what's in Stefan's bouquet. Elena is awakened by shouting. In the living room, Sage is helping Damon breathe, and says he shouldn't have opened something not addressed to him. Stefan enters and realizes that Damon has opened his bouquet. Damon has become human by magic intended for Stefan. The brothers fight. Everyone laughs. Elena vows to win against the kitsune.