Players take control of an unnamed main character who is suffering from a bout of amnesia and finds himself managing a group of seven delinquent girls at the behest of his superior, Toko. He is tasked with motivating these girls, by various means, in order to overcome the trials of the Hell Spire, confront their sins, and reform so that they can return to the real world.
However, things go awry when Convicts, sinners who have been denied reformation, stage a revolt on the Hell Spire, abducting much of the personnel, including Toko (the main character's superior), and causing Hell Spire activities to cease. To make matters worse, there is a Convict hiding amongst the seven girls. Hoping to keep the Hell Spire from being sabotaged any further, Maya, another Program Instructor, sends the main character and his group straight to Hell. With nothing but occasional advice from Toko, the main character and the delinquents are forced to find their way back into the Hell Spire while constantly watching their backs for the Convict that got them sent to Hell in the first place.
Aside from improved graphics, the sequel adds the S/M system, which allows the player to customize each of the girls move set to their liking and the Coaching ability, which allows the main character to buff or debuff the girls based on the skills they chose.
This game contains examples of:
- Adults Are Useless: When learning about each of the girls' pasts, many of them had parents and/or teachers who simply didn't care about helping them or didn't take their problems seriously, leading the girls to fall further in despair. Averted with Lily's parents and Mizuki's grandma, who do try to be as supportive as possible but are pushed away.
- Bowdlerize: While the voices are once again absent from the punishment segments, which is again localised as "Motivation" like in the first game, the artwork has been redrawn instead of being covered by pink mist. The Fanservice is kept intact, but the bondage elements and some expressions have been changed to imply consent from the girls instead of being forced against their will.
- Continuity Nod: When discussing Knighthood, Toko mentions that the process was different in the past, requiring a special item, but has changed due to abuse. This is likely referring to how the girls from the first game had to drink a potion in addition to possessing a pure soul to become a Knight. The current cast only requires a pure soul.
- Contrasting Sequel Main Character: The main character of the first Criminal Girls became a Program Instructor by accident when he failed to properly read the details of his job. The main character in this game starts out as an Amnesiac Hero. It's eventually revealed that he specifically became a Program Instructor to look out for girls after he failed to do the same for his sister. He also takes the job much more seriously early on, trying to defuse fights between the girls and takes hits for them more often. Because of this, his girls warm up to him a little more quickly than the previous main's girls.
- Gameplay and Story Segregation: As with the first game, the Motivation mini-games where the Instructor performs various actions on the girls in a titillating manner has no bearing on the game's characters and story at all.
- The Grim Reaper: The Dreaded of Hell whose job is to deal with Convicts if it gets too overpopulated and grants its victims a truly permanent death. Throughout the game, the party is forced to flee or find ways to trap it. Even when the girls receive their Knight forms and are able to overpower it, it has the power to immediately recover all the damage they dealt to it. Luckily, Enri is able to teleport it away before it could attack again.
- Heroic BSoD: Like the first game, each of the girls experience one when they come face-to-face with their sinful past or the direction their current behavior may lead them. Bringing them an item from their past is what allows them to break it.
- Instant-Win Condition: In terms of the Reformation Program, managing to become a Knight is the very best indicator of truly finishing the Program; it guarantees any Delinquents who gain it resurrection, even if they've already failed the Program before, as Enri reveals after all seven girls attain it.
- Marry Them All: Upon defeating the True Final Boss, if you choose to stay with Enri to help fix the Hell Spire, the girls take turns spending time with the main character. The ending is even called the Harem Ending.
- Multiple Endings: Upon defeating the final boss, the player is given a choice between which of the seven girls to send home first, as they can only be sent one at a time. Each one gives an ending specific to each of the girls, showing each of them taking what they've learned from their time in Hell to heart, but sadly having no memory of the Instructor or the friends they've made there. Upon achieving all seven endings, a new option pops up, granting the player access to The Very Definitely Final Dungeon and the True Final Boss. Defeating the True Final Boss gives the player a choice of seven new endings for each of the girls, this time having retained their memories and are now going out with the Instructor. Finally, completing all of the girls' wishes gives the player access to an extra choice. Choosing this choice grants them an all-new eighth ending. The main character and the seven girls decide to stay with Enri to help rebuild and reform the Hell Spire, becoming the new administration.
- My Greatest Second Chance: Just like the first game, the Reformation Program is designed to give the girls, who have died in real life, a second chance by allowing them to change for the better before returning to the real world. This goes double for Sui, who had failed her program the first time and got sent to Hell as a Convict.
- Status Buff: Aside from the various stat-increasing spells, the Instructor is able to induce a temporary buff to the party members via Coaching. By choosing one of four options (Scold, Praise, Sympathize, and Worry), the party gets a buff or debuff based on the character and whether their skill set is S-skill (offensive buff/debuff) or M-skill based (defensive buff/debuff). A skill set possessing all S-skills or M-skills will result in a Full Throttle boost, granting the maximum buff a character can receive.
- Stripperific: Yurine, Tsukasa, and Mizuki have tops that barely conceal their chest. It gets especially ridiculous once all the girls become Knights with each girl showing varying levels of skin and gets even worse as some of them strip down even further for Motivation.
- Wham Episode: The Girl's Garden chapter. Sui accuses Maya of being a Convict and being the true voice behind Toko. Sui knows this because she had briefly seen Maya herself in Hell, as she is the Convict that wormed her way in with the Delinquents. Maya reveals she had been manipulating the party into destroying the defenses of the System Manager so that she can take over the Hell Spire and the Reformation Program. Finally, Enri is the newly-born System Manager.
- Wham Line: In the Girl's Garden chapter, just as Maya is about to enter the Manager's Floor:Sui: Everyone, don't be fooled! She's not a Program Instructor... She's a Convict!