"Madly Ever After"

The plot starts with Gertrude falling into Fairyland as a six-year-old. She spends 27 years looking for a key to escape with her assigned insect guide Larrigton Weighston III, or Larry for short, but never ages, resulting in her becoming a violent sociopath. After terrorizing Fairyland, Queen Cloudia, the secretly evil ruler of Fairyland, sends after Gertrude many 'villains', such as a witch named Horribella. With each attempt ending in failure, Queen Cloudia then decides to kill her personally. She consults the Fairyland Council and they devise a plan to rid of Gertrude. As the Queen cannot directly harm any guests, Cloudia invites another child, Happy, into Fairyland, to make Gertude a citizen of Fairyland. Gertude confronts Happy and shortly tries to kill her, but is easily defeated by Happy. After Gertrude recovers, she visits Queen Cloudia and asks her what is going on. Cloudia tells her she's too late, and admits she helped Happy on her quest to find the key. Sometime after, Happy does find the key. Annoyed by this, Gertrude finds Darketh Deaddeath, who she asks to help her defeat Happy. He agrees to help her, only if she proves herself. She survives his dungeon, and insults him. He then decides to help her and gives her his dark magic powers. Happy almost uses the key to exit Fairyland, but then a super-powered Gertrude stops her in her tracks. After a brief battle, Gertrude defeats Happy and then kills Cloudia. Before Gertrude can return home, Larry informs her that killing the Queen makes her the Queen herself, resulting in her unhappily taking the throne.

"Fluff My Life"

After a disastrous year as Fairyland's "evil queen", Gertrude is impeached and resumes looking for a way home. While meeting with Pervis Peddlesteal, an anthropomorphic rat who collects artefacts from Earth, she encounters Duncan, a human boy dressed in a dragon Halloween costume recently arrived in Fairyland. Duncan joins Gertrude on her travels, however, she willingly abandons him in the Tower of Battle, a gigantic arcade machine populated by powerful fighters. One hundred years later, Duncan has become an actual giant dragon and lays waste to Fairyland, killing all but a small handful of survivors, including Gertrude and Larry. Using the last remaining magic in Fairyland, Larry transports Gertrude back in time to the present of the series to warn her younger self away from the decisions that lead to the destruction of Fairyland. The older Gertrude gives her younger self step-by-step instructions to avert the apocalypse, but wearily notes that she has not listened to any of them, fading from existence as her younger self rushes into the first of many disasters.

"I Hate Image"

After beating up Kamau Kogo on Bitch Planet and learning how to traverse the Image Universe to return home, Gertrude kills versions of Rick Grimes and Coach Euless Boss before following the Paper Girls into Image City. After being led to the god-run nightclub Wic + Div by Tony Chu, Gertrude sets off a battle royale between the various superheroes and villains within, stealing their weaponry in the process, before seeking out the aid of Spawn to give her access to the Image Central building. After killing everyone in the building and confronting the founders of Image Comics, Gertrude demands to be allowed to go home, killing them all as a show of force before realising she needed one of them alive to return home. Dejected, Gertrude returns to Fairyland with Larry.

"Good Girl"

Gertrude meets Maddie, a denizen of Fairyland and her self-proclaimed "biggest fan", who idolises Gertude for the violence and death she has spread. Although initially happy to take Maddie on as a protege, Gertrude quickly becomes sick of her, and realizes that she does not like the person she has become. She murders Maddie and resolves to become a better person. Despite her best intentions, Gertrude repeatedly fails to do good, leaving just as much death and destruction in her wake. However, Larry tells her of a mysterious labyrinth which could hold the secret to helping her become good, and concedes that, as miserable as his life with Gertrude has been, it probably would have been even worse had they never met. When they reach the labyrinth, its master, Loveth Lovelord, makes Gertrude a deal; if she can reach the center of the labyrinth before the next "Lover's Moon" and find the "Balls of Redemption", all the evil will be purged from her being, if she fails, she must become his wife. Gertrude manages to find the centre of the labyrinth, and Loveth unleashes the beast that guards the Balls, which turns out to be Duncan. Despite Duncan demonstrating the newly acquired draconic powers of flight and fire breathing, Gertrude easily defeats him and touches the Balls of Redemption, becoming a perfectly good and sweet child similar to Happy. The newly good Gertrude makes quick progress in her quest, prompting Horribella to hire the deadliest assassins in Fairyland to stop her on behalf of an unseen "Ruler of All That is Dark". Gertrude finds her key and heads back to the centre of Fairyland to finally leave. Horribella's assassins attack her, but all inexplicably miss her when they throw their weapons. Gertude picks up a lollipop and skips towards the door, but trips and falls at the last moment, causing the lollipop to penetrate her brain, killing her instantly. As Larry quietly mourns her death, Gertude descends into Hell, with the effects of the Balls reversed. Upon arriving in Hell, she is met by the "Ruler of All That Is Dark" – Happy.

"Sadly Never After"

The ruler of Hell is revealed not to be Happy, but a shapeshifting demon named Bill assuming her form. After failing to torment Gertrude with a twisted version of her home, he condemns her to an eternity of repeating her quest. Meanwhile, Horribella calls Bill and demands Queen Cloudia's bones, her payment for engineering Gertrude's death. Bill has the bones delivered to her by Duncan, who has become a postal courier. Horribella, planning to bring about the end of Fairyland, resurrects Cloudia as a powerful undead being who kills her and goes on a destructive rampage. Realising that Gertrude is the only one who can defeat "Dark Cloudia", Duncan and Larry confront the Fairyland Council and tell them that they must resurrect Gertrude to save Fairyland. The Council initially refuse, citing the rules of Fairyland, but Duncan retorts that the rules, and the council, are directly responsible for the crisis, and that by kidnapping children like him and Gertrude, they have abdicated any moral authority. One of the Council member concedes that Duncan is correct, and orders Bill to deliver the pocket dimension containing Gertrude's Hell to the council chamber. Duncan and Larry enter Hell and inform Gertrude about Dark Cloudia; subsequently, Gertrude agrees to kill Cloudia again. When returned to Fairyland she attempts to renege on the deal and demands to return to Hell when she realizes that her actions would serve the council's purpose. The Council nevertheless promises to return Gertrude home if she succeeds, and forcibly empowers her with their combined magic. Meanwhile, Dark Cloudia destroys the army of King Cone, the new Fairyland king, who tries to stop her wave of destruction in vain. Before Dark Cloudia can slay the king, however, Gertrude appears and attacks her with her new magical powers, depowering Cloudia and beating her up. Although Gertrude almost kills Cloudia again, Larry reminds her that the Council never specified that Cloudia has to die in their request, and Gertrude decides to follow his advice for once and gives the defeated villain to King Cone so she will be imprisoned for her crimes. The Council then appears, angry because Gertrude didn't kill Cloudia (despite the fact that she technically fulfilled their request) and threatening to exile her to a remote place in Fairyland, until Gertrude reminds them that she still has their combined magic inside her and would use it to kill them unless they honor their part of the deal, and the fearful Council quickly sends her back home, much to Larry's sorrow. Back on Earth, Gertrude, now an adult woman in her thirties, finds herself employed as a clerk in a television station, ironically frustrated by her mundane job and looking for a way to return. However, she abandons her search and ruefully curses Fairyland one last time before getting back to work, determined to face her lot in life.

"Gert's Inferno"

The now adult Gertrude is unable to keep a job, as she lacks any education or skills applicable to the real world, and misses Fairyland where she was notorious and feared. After she is beaten up in a bar and dumped in an alley, a tech billionaire named William Wiggins hires her to find his missing son, who he believes has been taken to Fairyland. Gertrude agrees, in exchange for half the profits from the planet-wide theme park that Wiggins intends to build on Fairyland once the expedition is complete. He sends Gertrude and Rotwald Rat, a talking rat from Fairyland who his scientists accidentally brought to Earth; through a portal to Fairyland. They emerge at the gates of the Inferno, a hell-like dimension created to prevent previous visitors to Fairyland re-entering. They meet a demon named Virgil, who agrees to guide them through the Inferno and into Fairyland, promising the journey will last a few days. However, Gertrude eats Virgil's map and they are lost in the Inferno for years. Along the way they inadvertently create additional dangers for themselves, including a ravenous "gertling" known as "Cutey Pukey", and a golem created from a monster's stomach contents which lusts after Gertrude.

Gertrude, Rotwald and Virgil are finally able to complete a series of fetch quests to reach the end of the Inferno and obtain a ticket into Fairyland. Gertrude tearfully bids farewell to Virgil and re-enters Fairyland. As soon as they cross through the portal, Rotwald receives a call from Wiggins, who tells Gertrude that his son has shown up on Earth and that he has no intention of extracting Gertrude due to legal issues, leaving her once again trapped in Fairyland permanently. Gertrude kicks Rotwald in a rage, declaring "I hate Fairyland!". Rotwald lands some distance away in front of the latest "guest" of Fairyland, and Larry who is shocked at hearing Gertrude had returned.

"Last Gert Standing"

As Gertrude reunites with Larry, Larry explains that he got a successful career as guide since she left and that he guided Wiggins' son. Meanwhile, Fairyland's new ruler and Cloudia's brother, King Cloudius, gets enraged to learn about Gertrude's return. After rejecting suggestions from the new cousil, Cloudius decides to bring the original Gertrude and several different counterparts to his timeline to kill current Gertrude. As Gertrude goes with Larry and the kid to the door upon finding the key, Cloudius sees throught Gertrude's cheap ghost costume, starting a bloody battle between Gertrude and her counterparts until only the original Gerturde survives. However, to Cloudius' anger, Gertrude lets the kid to use the door unaware of it was the way home Cloudius promissed her to if she killed adult Gertrude.

Gertrude decides that she would search for Duncan and ask him for help when Larry assumes that he would have a map and a key. They see that Duncan is now an adult man with anger issues and working for Horribella's cousin. Although upset with Gertrude for the way she treated him back when he was a child, Duncan accepts to help Gertrude.