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Calligraphy Club
Keiki Kiryū
Voiced by: Hiro Shimono (Japanese), Clifford Chapin (English)
A second-year student who, despite envying couples, is surrounded by perverted love interests.
- Accidental Pervert: Well, it's not actually his fault since the girls provoked him to do sexual stuff against his will.
- To Sayuki - He had to get the key stuck between her breasts in order to uncuff her. And later on, he had to "massage" her butt so that Sayuki would stop licking and pinning him on the ground like a dog.
- To Yuika - They almost had a lips-to-lips when she tied him to a chair for the sake of punishing him. Although this was interrupted by Sayuki, Mao clearly saw that Keiki was a bit aroused by this.
- To Ayano - He saved her from falling down the stairs and she fell right on top of him. Due to her scent fetish, she wished for the both of them to stay that way on the floor for a little longer.
- Alliterative Name: Keiki Kiryu
- But for Me, It Was Tuesday: He completely forgot about the first time he met Mizuha when they were younger. And even when he does remember it well, he still tells her this. She fell in love with him because of his promise that they'd be together forever, which to her was essentially a Love Confession. However, to him, it was just another day and he didn't want to see her as anything other than a younger sister.
- Butt-Monkey:
- Even outside of attracting perverted girls and being called a The Casanova, Keiki has a Running Gag of being blackmailed.
- Not to mention that he's the model for the submissive protagonist of a yaoi doujin.
- Buxom Beauty Standard: He admits to preferring big breasts, though he appreciates smaller ones too.
- Clueless Chick-Magnet: Keiki initially has no idea that Sayuki, Yuika, Mao, and Mizuha are romantically interested in him until he finds an anonymous love letter that one of them could have wrote. Then this trope gets defied as Keiki himself had been investigating the girls for his quest of finding "Cinderella". He had to constantly theorize and look for various clues or objects that would prove their secret romantic affections for him, for the sake of finding out who wrote the letter.
- Chronic Hero Syndrome: The reason why he joined the Calligraphy Club? Keiki was concerned that nobody else is accepting Sayuki's club pamphlets. It was also thanks to him that the club later had more members (since the other girls liked him for specific reasons and joined to keep watch on him for their needs).
- Failed a Spot Check: He somehow failed to notice that he and Mizuha are not blood-related, despite knowing that he's only five months older and that pregnancy lasts longer than that. He actually did notice when he was younger, but his parents came up with an outlandish lie to explain the contradiction, since they believed he would be better off seeing Mizuha as a sister while they're still children.
- First Kiss: At the end of episode 11 and Volume 3's epilogue, he's kissed by Mizuha.
- The Generic Guy: He considers himself plain-looking and average, which is one of the reasons why he didn't expect his female friends to be romantically interested in him. Mao acknowledges that he's plain-looking, though she states she needs him as a model because plain faces are harder to draw than handsome ones.
- Good Angel, Bad Angel: Subverted. When Sayuki tries to sell him on adopting her as a pet, Keiki has an emergency brain meeting with his shoulder angel and devil. The angel argues for refusing the master-pet role at first, but the devil successfully tempts the angel by appealing to his lust. Keiki ends up refusing both his angel and devil's suggestions.
- Grass is Greener: Keiki starts the series single and jealous of couples. Even when he discovers that his female friends may be interested in him and when he receives an unambiguous love confession from Mizuha, he's still jealous of other couples for having relationships devoid of bizarre perversions while his love interests are perverts.
- Horrible Judge of Character: After discovering that Mizuha is the sender of the love letter, he doesn't suspect that she has a kink of some kind, despite how she left her panties behind with the letter.
- Hypocritical Humor:
- Despite criticizing others' pervertedness, he has slight siscon tendencies and apparently collects porn mags, though he considers this normal behavior for boys.
- He's surprisingly good at playing the role of Sayuki's sadist master and turning her on with embarrassing requests, as shown when he has her lick his finger among other actions during their date in Volume 2. He starts to wonder if he awakened to his inner sadist.
- Jerkass Realization: When Yuika and Sayuki try to give up on their fetishes so they can be his ideal girl, Keiki feels uncomfortable about this sudden change. After talking to Mao, he realizes that his plan to make the girls normal will hurt them in the long run by making them deny their interests.
- Love Epiphany: Yūhi states that he's in love with someone, but he has yet to realize his feelings. At the end of Volume 11, he seems to have figured out who he's really in love with, but doesn't state who. Volume 12 reveals that he's in love with Mizuha.
- Moment of Weakness: At the end of Volume 6, in a fit of anger, he tells Sayuki that he prefers working for the student council than being in the Calligraphy Club, causing her to cry. He immediately regrets this and spends much of the next volume trying to make up with her and save the club from disbandment.
- My Sister Is Off-Limits: He becomes worried when Rin starts flirting with Mizuha.
- Only Sane Man: Like The Generic Guy above, he doesn't have any noticeable quirks compared to the rest of the cast. And as a result, he has to be the one to stop antics from happening.
- Playboy Bunny: A rare male variant. Yuika forced him to wear a skintight bunny suit when she was visiting his room.
- Punny Name: His first name sounds like "cake," which Sayuki often pokes fun at. Mao uses this pun for the title of her "Shortcake" series, which Keiki sees as a violation of his privacy.
- Shipper with an Agenda: Subverted. At first, he plays matchmaker between Koharu and Shōma because Koharu blackmailed him with a photo of him reaching into Sayuki's cleavage. She eventually reveals she deleted the photo, but Keiki is still invested in helping her and tries to get her and Shōma back together after her age is revealed.
- Tsundere: Despite being disturbed by the perversions of his friends and snarking at them, he still cares about them and goes out of his way to help them with their problems.
- Unwanted Harem: While he wants a girlfriend, he wants a girlfriend who fits his definition of normal by having no bizarre kinks. This causes him to reject the Calligraphy Club members, though they haven't given up on him.
- Wild Take: In the manga, Keiki tends to have exaggerated and comical facial expressions. One of his expressions when he's scheming resembles Light Yagami's "just as planned" grin.
Sayuki Tokihara
Voiced by: Ayana Taketatsu (Japanese), Mallorie Rodak (English)
A third-year who is the president of the Calligraphy Club.
- Big-Breast Pride: She brags about her chest, knowing that Keiki prefers large chests and that Yuika is jealous.
- Broken Pedestal: Keiki looks up to Sayuki as a hardworking and graceful upperclasswoman, and is shocked to learn of her closet masochism.
- Buxom Beauty Standard: She has a very large bust, which Kekki lusts after and Yuika is envious of.
- Chekhov's Skill: Her calligraphy skills can be applied to ketchup writing on omurice. When she displays this skill in a culture festival contest, she's able to make the club's maid cafe really popular and make enough profit to cover the club's misused budget.
- Clingy Jealous Girl: Doesn't like it when Koga keeps playing The Tease around Keiki, and in some cases deliberately does things to provoke her, such as sitting on his lap while she's nearby.
- Covert Pervert: She's secretly a masochist who wants Keiki to treat her like a pet and literally own her.
- Education Mama: Or in her case, Education Papa. Her father wanted her to focus on refining her calligraphy skills at the cost of her social life.
- Exact Words: When she and Keiki helped the lost dog find its owner in the park, Sayuki expressed her jealousy from the owner's affection towards a pet, and thinks that she wants to be like that dog. This is actually her secret kink, she wants Keiki to treat her like a dog, even going as far as roleplaying a female dog when he's around!
- First Kiss: She's the first female lead who kissed Keiki, but on the cheeks.
- First Love: Keiki admits Sayuki is the first girl he fell in love with, but ultimately chooses Mizuha over her.
- Foil: Sayuki is masochistic (she sees Keiki as her master and wants to be punished by him) while Yuika is sadistic (she sees Keiki as her slave and wants to punish him for her enjoyment). Keiki even wonders why they have the opposing kinks. The girls' mocking nicknames towards each other also apply, since the former gets called "Masochist" while the latter "Sadist".
- The Gadfly: She likes to pull pranks on others, as shown when she draws on Keiki's face and makes Yuika wear a bunny costume before allowing her to join the club. This actually works with her masochism rather than conflict with it, since she can demand punishment for her pranks.
- Going Commando: In Episode 9, she goes on a date with Keiki without wearing panties, though this doesn't seem to be a habit like with Mizuha.
- Heroic BSoD: When Keiki tells her that he prefers working for the student council than being in the Calligraphy Club, Sayuki cries and avoids Keiki for a while, though she eventually makes up with him.
- Hidden Depths:
- For a self-described masochist, she can come up with some surprisingly aggressive plans when she thinks Keiki isn't giving her enough attention. When Keiki gets closer to Ayano, Sayuki gets herself and Keiki alone so she can lick him. At the end of Volume 5, she uses the club budget to buy bunnygirl suits and then has herself and the club members swarm Keiki.
- During the school festival, she turns out to be very business savvy and figures out how to get good publicity for the club's maid café.
- Lecherous Licking: When Keiki spends time with Ayano, Sayuki gets jealous and licks his face in order to "mark" him.
- Love Confession: In Volume 11 Chapter 2, she confesses to Keiki while she thinks he's sleeping. Since he was actually awake for the confession, he gets too embarrassed to interact with her, resulting in Sayuki pulling a Wall Pin of Love to get him to talk to her. Keiki then admits he heard her confessing.
- Malicious Misnaming: Calls Yuika "Sadist" because she just hates her as a rival to Keiki.
- Marshmallow Hell: She pulls Keiki's face to her breasts in retaliation for tickling her belly while inside his room.
- Ms. Fanservice: She skirts between Shameless Fanservice Girl whenever she's alone with Keiki, and into a Reluctant Fanservice Girl when she's out with him in public. She has no qualms acting like a dog when they're alone, but gets incredibly self-conscious when he orders her to do those same things in public. She does state that she only wants to act like this in private.
- Nice Job Breaking It, Hero: She spends club funds on bunnygirl costumes so that she and the club members can seduce Keiki into spending more time with the club. This causes the student council to consider disbanding them unless they can repay the misused funds.
- Property of Love: The other characters think that Sayuki is romantically involved with Keiki or is already his girlfriend. But all she can think of about their relationship is that Keiki is her master while she is the pet.
- Strange Minds Think Alike: She and Yuika each stole a pair of boxers from Keiki's room. Though unlike Yuika, she decided to wear it to school.
- Too Kinky to Torture: Sayuki is a masochist and wants Keiki to treat her as a pet and even punish her if she does something unfavorable. Naturally, Keiki is weirded out by this and he doesn't actually do anything to harm her.
- Trash of the Titans: She isn't good at keeping the clubroom clean. The very first scene in the series is her and the main characters disposing of the papers strewn about the clubroom and cleaning ink spills.
- Victoria's Secret Compartment: Done accidentally once she handcuffed herself. Sayuki was supposed to have the key in her lips (to seduce Keiki), but it fell in between her breasts and Keiki had to reach for it with his hands.
Yuika Koga
Voiced by: Rina Hidaka (Japanese), Madeleine Morris (English)
A first-year who serves as a library committee member.
- A-Cup Angst: She's not happy that Keiki prefers big breasts and calls Sayuki "Witch-senpai" for having them.
- Aggressive Submissive: Yuika tends to talk a big game, declaring that she wants Keiki to be her slave and being very forceful at times. However, the moment Keiki starts to become more assertive she becomes very nervous and excited. She also tends to dream about him as an aggressor groping or dominating her.
- Almost Kiss: She was almost close to kissing Keiki on the lips as his "punishment", until Sayuki barged into the room after hearing their voices.
- Blackmail: She takes a picture of Keiki holding her underwear (he was looking to see if she took the "Cinderella" panties from his room) to make him into her slave. He turns the tables when he finds out she stole his underwear too and makes her delete the photo.
- Bookworm: She spent most of her time reading books alone in the library, until Keiki started interacting with her and has grown infatuated with his kindness. She also has a talent for drawing story books.
- But Not Too Foreign: She's one-quarter British on her grandmother's side. This unfortunately led to her being discriminated by the other Japanese kids.
- Clingy Jealous Girl: Gets mad whenever she thinks Sayuki is getting ahead of her in wooing Keiki.
- Covert Pervert: She secretly wants to make Keiki her slave and engage in S&M activity with him. She also had a dream about Keiki groping her breasts, suggesting that she's more receptive to the "M" role than she likes to admit.
- Everyone Has Standards: Played for Laughs. Despite wanting to be Keiki's master, she's scared when a drunk Keiki fulfills his promise to Sayuki by spanking her. When Keiki forgets about the event after his hangover, he asks Yuika what happened and she exclaims that butts aren't made for that activity.
- Foil: Sayuki is masochistic (she sees Keiki as her master and wants to be punished by him) while Yuika is sadistic (she sees Keiki as her slave and wants to punish him for her enjoyment). Keiki even wonders why they have the opposing kinks. The girls' mocking nicknames towards each other also apply, since the former gets called "Masochist" while the latter "Sadist".
- Friendless Background: She was ostracized for her foreign ancestry and was still grieving over her grandmother's death, and didn't open up to others as a result. It took Keiki several attempts to talk to her to get her to befriend him. This leads to Yuika believing that Keiki was a masochist for trying to befriend her despite her coldness, and that he wanted to be her slave.
- I Kiss Your Foot: Demands that Keiki should kiss her foot as his punishment for interacting with Sayuki again. Subverted as he rejects while the latter arrives just in time.
- Love Confession: She confesses to Keiki at the end of Volume 10, stating that she's willing to become a normal girl to be with him.
- Malicious Misnaming:
- Calls Sayuki "Masochist" or "Witch" because she just hates her as a rival to Keiki.
- Heck, she even goes as far as calling the Calligraphy Club as the "Witch's Den".
- Sadist: An effect of her kink from wanting Keiki to be her slave is to engage with sadistic activities on him. When she first revealed her secret to Keiki inside a locked room, she pinned him to the floor and tried to suffocate him by forcing her freshly-removed panty into his mouth. Even Sayuki knows this trait of hers and calls her "Sadist".
- Strange Minds Think Alike: She and Sayuki each stole a pair of boxers from Keiki's room.
- Unishment: By her own definition of "punishing" Keiki for meeting up with Sayuki, Yuika ties him to a chair, making him choose either to kiss Yuika's foot or be kissed by her in the lips. He gets aroused at first, but eventually thinks back as both options are wrong when no actual love is present. Sayuki then arrives, interrupting the scene.
- What Do You Mean, It's for Kids?: In-Universe, Keiki finds her picture books disturbing for having the princess enslave a foreign prince that she has a crush on. Despite that, the art style is similar to actual picture books.
Mao Nanjō
Voiced by: Iori Nomizu (Japanese), Kristen McGuire (English)
A second-year who often hangs out with Keiki and Shōma.
- Big Damn Heroes: Sayuki and Yuika were fighting a tug-of-war over Keiki who was tied in a chair. But Mao arrived in to interrupt the scene, drag Keiki out of the room and untie him so that she could have a chance to talk to him alone.
- Cannot Spit It Out: Even after revealing her BL tendecies to Keiki, making him believe that it is the only secret that she has, Mao actually has hidden romantic feelings towards him, if her private thoughts and personal monologues are indications.
- Clark Kenting: She wears glasses and her hair up when she's in her manga artist mode. Keiki initially doesn't realize it's her until she takes them off.
- Clingy Jealous Girl: Played with. She doesn't want Keiki to get close to girls but is fine with him hooking up with guys, since the former scenario would kill her inspiration for her boy's love doujin. She joins the Calligraphy Club to keep an eye on his relationship with the other girls.
- Crippling Overspecialization: She's good at making boy's love works but struggles more with shōjo, since she doesn't have much experience in relationships between girls and guys. She eventually makes a series based on Keiki's situation, but with the genders swapped so that it's about a girl surrounded by perverted guys.
- Foreshadowing: There are already hints to her Yaoi Fangirl tendencies even before she explicitly reveals it:
- For a short while, there is a scene of Mao drawing what appears to be a manga. Upon closer inspection, it looks like a male-on-male image.
- She glees and smiles Out of Character when Shoma saves Keiki from tripping in the arcade club, with the former holding the latter by the waist. The scene also is subtly played with a Bishie Sparkle. Mao then takes her phones and quickly captures the scene as if it was a once-in-a-lifetime event.
- Gamer Chick: She's shown to be skilled in shooting and fighting games, as shown when she solos an arcade game that Keiki and Shōma only lasted ten minutes in.
- Guy on Guy Is Hot: She's a boy's love artist who uses Keiki and Shōma as inspiration for her series, and can reimagine mundane interactions between them as R-18 scenarios. After learning of Rintarou's cross-dressing and seeing him and Keiki in a compromising position, she makes a character based on Rintarou and adds him to "Shortcake" as a romantic rival.
- Netorare: Invoked. She considers Keiki starting relationship with girls to be cheating on Shōma, and believes that this NTR situation would turn off her readers. Though she's fine with NTR as long as Keiki hooks up with another guy.
- Not So Stoic: Once the cat's out of the bag regarding her BL tendencies, she becomes more open towards Keiki, at the cost of requesting him to spend more time with Shoma for her own materials. When she slips into her "fujoshi mode", she can be just as talkative as she wants to, even sporting some visors out of nowhere.
- She Cleans Up Nicely: Keiki is surprised how elegant she looks when she dresses up for their date and almost doesn't recognize her.
- The Stoic: She spends most of her early screentime just shyly glancing at Keiki, and scoffing at him or running away when he wants to interact with her. However, she has a 180-degree turn when she finally revealed her secrets to him.
- Tsundere: Of the club members, Mao is less obvious about her feelings for Keiki and insists that she's mainly interested in him as a model for her boy's love works. However, her private thoughts reveal that she does have romantic feelings for him but Cannot Spit It Out.
- Yaoi Fangirl: While all the girls in the club show interest in boy's love media, Mao is notable in that she's the author of a boy's love series based on Keiki and Shōma, called the "Shortcake" series. She's always on the lookout for more "inspiration".
Mizuha Kiryū
Voiced by: Kaede Hondo (Japanese), Emily Neves (English)
A second-year and Keiki's younger sister.
- Beneath Suspicion: Keiki and Shōma decide to cross her off the list of "Cinderella" candidates, since she's Keiki's sister. She turns out to be the sender of the love letter and isn't blood-related to Keiki.
- Broke the Rating Scale: Her confession during the contest in Volume 3 scored 120 points, which broke the limits of the rating machine.
- Dull Eyes of Unhappiness: In the manga, her pupils turn almost completely black when she sees Keiki in perverted situations with Sayuki and Yuika.
- First Kiss: At the end of episode 11 and Volume 3's epilogue, she takes Keiki's first kiss on the lips.
- Going Commando: In fifth grade, she forgot to bring panties to change into after swim class and she had to spend the entire day that way, which she found liberating. Afterwards, she often goes to school without panties and secretly takes strip tease selfies in order to experience this feeling of liberation. This habit is also the reason why her panties were left behind with her love letter.
- Hidden Buxom: She has the second largest chest in the club, but her clothes and uniform tend not to emphasize this.
- Neat Freak: She becomes excited at the prospect of cleaning the club room, which accumulated a lot of discarded paper and ink stains. In episode 11, Keiki uses this trait against her by surprising her with an invitation to a pool amusement park and giving her a swimsuit to change into. When she has to change out of the swimsuit, she can't bring herself to reuse the unwashed panties she wore before, so she has no choice but to wear the Cinderella panties. At the end of the episode, Keiki flips her skirt to confirm that she's Cinderella.
- Nice Girl: She always consoles Keiki when he's feeling troubled and is kind to the other club members despite seeing them as rivals.
- Not Blood Siblings: At the end of Volume 3, she reveals that she was adopted into the family. Unfortunately, despite Keiki eventually reciprocating her feelings in Volume 12, they are still seen as siblings on a social level, which means their relationship would be shunned by their peers. This causes her to reject Keiki's confession in Volume 12's epilogue, since she doesn't want to ruin Keiki's reputation.
Student Council
Ayano Fujimoto
Voiced by: Anzu Haruno (Japanese); Emi Lo (English)
A second-year who is the student council vice-president.
- The Ace: She's described as the ideal honor student, with good grades and popularity among both students and teachers.
- The Comically Serious: Compared to other characters in the series, she doesn't emote much, which makes it funnier when she stoically tries to sniff Keiki's underwear.
- Cuddle Bug: When Keiki saves her, she immediately hugs him and often does so again in their later encounters. This is because she wants to bask in his scent.
- The Nose Knows: She has a sensitive sense of smell, to the point of being overwhelmed by the smell of sweat from a fair distance away. She has to pinch her nose when questioning the drunk Yūhi Akiyama, since the latter reeks of alcohol.
- Perverted Sniffing: She has a scent fetish and enjoys sniffing Keiki.
- Red Herring: Her interest in the Calligraphy Club's lockers makes Keiki suspect that she may hid in them as "Cinderella." Then it turns out she's mainly interested in lockers because they might contain sweaty jerseys and similarly smelly items.
- Rescue Romance: While she is attracted to Keiki due to his scent, another reason is because he saved her from falling down a flight of stairs.
Airi Nagase
A first-year and the student council treasurer.
- Defrosting Ice Queen: Zigzagged and played for laughs. Every time she starts warming up to Keiki, she'll see him in an intimate situation with one or more girls shortly afterwards, reinforcing her image of Keiki as a shameless Harem Seeker.
- Does Not Like Men: She tends to assume most guys are perverts, though she does want to overcome this mindset.
- Freudian Excuse: In elementary school, she saw a perverted boy lick her flute, causing her to distrust boys.
- Yuri Fan: She secretly writes fanfics about the Calligraphy Club members in yuri relationships and considers Keiki an obstacle to her fantasies, since the club members are forming a harem around him.
Rin Mitani
A first-year and the secretary of the student council.
- Buxom Beauty Standard: Unlike Keiki, who prefers big breasts but appreciates all sizes, Rin is only interested in girls who are above a certain size.
- Crotch-Grab Sex Check: Invoked. He lets Keiki know he's a boy by pulling Keiki's hand to his skirt and letting him have a feel.
- The Social Expert: Keiki notes that Rin is able to easily find a topic or common ground to discuss with another person.
- Unwitting Instigator of Doom: During the culture festival, Naoya Inui confesses to Rin only to be rejected. Naoya falls into despair, causing Megumi to run for president in order to ban all couples.
- Wholesome Crossdresser: He dresses as a girl when working with the student council, and he's convincing enough that Keiki almost fell for him.
Shiho Takasaki
A third-year and the student council president.
- Freudian Excuse: In middle school, a boy she had a crush on hooked up with someone else, but this caused her to be both simultaneously sad and aroused. Since then, she hasn't shown interest in any boy unless they had additional love interests.
- Gamer Chick: At the end of Volume 7, she's seen playing a portable console.
- Netorare: She gets turned on by stealing away a boy that others have a crush on as well as having her love interest taken by someone else. In Volume 8, she manipulates Sayuki and Yuika into thinking she and Keiki are about to have sex, just to motivate them into trying to seduce him while she secretly watches. Later, she advises the club members to woo him by pretending to give up on their kinks, just so she can imagine Keiki being NTRed from her.
- Reasonable Authority Figure: When the Calligraphy Club is caught misuing their budget, Shiho gives them a deadline to pay back the funds rather than disband them immediately.
- Stalker with a Crush: She claims to have a stalker and wants to go out with Keiki in order to shoo them off. This is actually a lie to make Keiki a part of her NTR scheme.
Megumi Onizuka
A second-year and a candidate for the next student council presidential election. After losing the election, she becomes vice president instead.
- Childhood Friend Romance: With Naoya Inui, who stood up for her when their classmates made fun of her last name. Unfortunately, they're Twice Shy about their feelings.
- Defeat Means Friendship: After losing the election and getting back together with Naoya, Megumi drops her anti-romance agenda and Ayano recruits her as vice president.
- Fetish: She probably has the tamest example of this trope in the series, since she's turned on by boys wearing glasses.
- Foil: Combined with Evil Counterpart during the election arc. Like Keiki, she resents "normie" couples and has her own romantic relationship issues. However, Keiki never tries to ban relationships between other people and even acts as a matchmaker for his friends while Megumi attempts to ban relationships from the school.
- Friendly Enemy: As a student council presidential candidate, she's friendly to her rival, Ayano, and only uses honest campaigning methods. When her club member attempts to use scandalous photos against Ayano, Megumi chastises him.
- Love Makes You Evil: After Naoya becomes depressed over being rejected by Rin, Megumi decides to ban all romance from school so that Naoya doesn't have to be reminded of that traumatizing event.
- Significant Haircut: After she mistakenly believes Inui rejected her, she cuts her hair, which she originally grew out because Naoya once called her a princess.
- Twice Shy: When she discovered Naoya's porn magazines, the latter started to avoid her out of shame, causing Megumi to wonder if he dislikes her. Surprisingly, her fetish for glasses only made them more distant, since she was afraid of him finding out about it.
Other Students
Shōma Akiyama
Voiced by: Keisuke Koumoto (Japanese), Jordan Dash Cruz (English)
Keiki's classmate and best friend, who is a proud lolicon.
- Butt-Monkey: Not to the same extent as Keiki, but he's been through similar traumatic events due to having perverted love interests.
- His older sisters are brocons who dote on him too much and he's being stalked by Koharu.
- In Episode 7, he's scared shitless when he discovers that Koharu placed photos of him all over the Astronomy clubroom's walls and ceiling..
- Comedic Lolicon: His preference for younger, flat-chested girls is treated as weird, but harmless. Though there is some drama and Black Comedy due to how he initially rejects Koharu because she's older than him and how he turned into a lolicon because of his sisters' advances.
- The Confidant: He's the first person who Keiki tells about Cinderella, though he's initially not informed about the Cinderella candidates' kinks until Volume 2 Chapter 4.
- Crazy Jealous Guy: After Koharu offers to let Keiki stay at her house for a while when he was suffering from a Heroic BSoD when he found out Mizuha was the Cinderella suspect, Shoma begins to develop an aura of jealousy. Keiki wisely realizes this, and declines her offer, not wanting to risk angering his friend.
- Freudian Excuse: His older sisters have a serious brother complex, as shown by how they waited for him in the shower while naked and covered in chocolate. This caused him to want to avoid older girls and eventually become a lolicon.
- Hair of Gold, Heart of Gold: He's blond and is very encouraging towards Keiki in his quest to find "Cinderella."
- Has a Type: His attraction towards lolis don't include older girls with underdeveloped bodies or younger girls with developed bodies.
- Jerkass to One: Downplayed. He's normally nice to everyone, but he's a lot colder to his older sisters because he's traumatized by their advances. However, he still cares about them enough to help them with a play or carry them home when they're drunk.
- My God, What Have I Done?: When he rejects Koharu, he feels a lot worse about it than with previous rejections, since he realizes he had fun dating her.
- Pretty Boy: He considered very handsome, which makes it all the more shocking for his admirers when he turns out to be a lolicon.
- You Are Better Than You Think You Are: When Keiki doubts that anyone could fall in love with him, Shōma tells him that his helpful personality makes him lovable.
Koharu Ōtori
Voiced by: Ayaka Ohashi (Japanese), Kate Bristol (English)
A third-year Astronomy Club member who blackmails Keiki into playing cupid for her and Shōma.
- A-Cup Angst: During the love confession contest in Volume 3, she secretly laments that most audience members prefer larger breasts.
- Actor Allusion: This isn't the first time Ayaka Ohashi voices a character called Koharu.
- Bait-and-Switch: At first, Keiki mistakes her for yet another secret admirer of his, which is understandable given her Ambiguous Syntax. But she quickly sets him straight that no, she has eyes only for his friend, flattering as his sudden marriage proposal might be.
- Because You Were Nice to Me: She falls for Shōma after he retrieves her hat when it got stuck in a tree.
- Clingy Jealous Girl: She gets upset when Shōma ogles a younger girl.
- The Confidant: She's the second person who Keiki shares his Cinderella search with, including the candidates' kinks.
- In the Hood: By Keiki's suggestion, she had to wear an orange hooded jacket to hide her third-years uniform from Shoma, even while indoors or outdoors! Of course, Shoma is very suspicious of this and she had to reveal her actual age to him later on.
- Love Confession: She gives Shoma one after they start getting along rather well, as she wants to make sure he's aware of her being slightly older than him. He rejects her initially, but Keiki talks some sense into him, and asks that they start out as friends first. She accepts that, and as time goes on, it seems they start to get along very well.
- Ojou: Her family owns a large construction company.
- Older Than They Look: She looks like a first-year highschooler or younger, but is actually a third-year.
- Stalker Shrine: She turned the entire Astronomy clubroom into a photo gallery of Shōma, where walls and ceiling are covered in photos. Shōma finds out in episode 7, nearly causing their relationship to end again until they come to a compromise where the ceiling photos are removed.
- Stalker with a Crush: She stalks Shōma using the Astronomy Club's equipment to observe him from afar and take photos. Even when going on a date with him, she secretly records a video of them bowling.
- Weak, but Skilled: Despite her size, she's a skilled bowler, and scores several strikes in a row using a lightweight ball.
Naoya Inui
A third-year who served as president of the culture festival committee.
- Face of a Thug: He has a scary face, but never does anything antagonistic.
- Geek Physiques: He describes himself as an indoor type of person and he struggles to carry Megumi during the bridal carry contest.
- Heroic BSoD: He becomes depressed after being rejected by Rin and drowned himself in his studies as a result.
- Twice Shy: At one point, Megumi found a porn magazine in his room. While she forgave him, he felt too ashamed of the incident to talk to her afterwards, leading to the two growing distant. Fortunately, the two get back together after the election due to Naoya learning that Megumi ran her campaign for his sake.
Other
Yūhi and Asahi Akiyama
Shōma's older sisters.
- A Day in the Limelight: Chapter 5 of Volume 8 of the light novels is about Yūhi dealing with her growing feelings for Keiki.
- Adapted Out: There is no mention of them in the anime, despite Shōma mentioning them both in the light novel and manga. There is however a possibility that they actually did appear in Episode 1, as a pair of girls that seems to resemble them can be seen in background while Keiki pats Sayuki's head, but it's too blurry to confirm if it's actually them or not.
- Affectionate Nickname: Yūhi refers to Keiki and Shōma as Kei-chan and Shō-chan respectively while Asahi calls them Kei-kun and Shō-kun respectively.
- Characterization Marches On: Before they were properly introduced in novels, it stated that both of them were brocons to Shōma, which is what led him to become a lolicon. When they were properly introduced, Yūhi had been dating other guys for quite sometime, while Asahi hasn't gotten over Shōma just yet.
- Graceful Loser: They challenge Koharu to a quiz and a fashion contest to test if she's worthy of their little brother. When Koharu wins, they accept the result with dignity.
- Hollywood Tone-Deaf: Asahi admits this about herself when in front of a karaoke bar.
- I Just Want My Beloved to Be Happy: Yūhi realizes Keiki is in unknowingly in love with someone else and decides to give up on confessing to him.
- Irony: Yūhi is the only girl Keiki manages to "rehabilitate" and is on her way to becoming the normal girl that Keiki is looking for, but their relationship sinks because she can tell that he's in love with one of the perverts from either the Calligraphy Club or the student council.
- Looking for Love in All the Wrong Places: Yūhi, thanks to a combination of lying to her friends about her sexual experience and the reputation that comes with it, makes it hard to form a long-term relationship with any man. She later sets her sights on Keiki since he found out about it and doesn't care, but gave up when she realized that he was already in love with someone else.
- Snowball Lie: Yūhi often claims to have a lot of sexual experience, but this is later revealed to be a lie to make her seem more adult-like to her friends, and she can't back out of that lie easily. Unfortunately, this lie also makes it hard to form a long-term relationship with any man.
- Tomboy and Girly Girl: Downplayed as Asahi is a Tomboy with a Girly Streak while Yūhi is the girly girl of the pair.
- Unwitting Instigator of Doom: They didn't expect their overwhelming affection towards Shōma to turn him into a lolicon.
