When Ichigo ran into a young Arrancar when navigating the vast desert of Hueco Mundo, he never would’ve thought that she would become a companion for most of his journey and a friend after the Arrancar arc. Ichigo also never expected a young child to have the mouth of an adult the way Nel did: she often said things that were too perverse in nature to come from a regular youngster and one of those things is what got her onto this list.

Nel describes herself to Ichigo at some point early in their relationship as a bit of a masochist and adds that he needs to “make her cry a little or else it’s no fun”. It’s worth mentioning that she is referring to the simple and innocent game of tag. In addition to needing to spice up tag with tears, Nel Tu later steals Ichigo’s Zangetsu to incite a new game of tag, screaming gleefully that Ichigo should catch her and beat her up. It is great to see children learning to become fully-fledged weirdos.

Fukawa Touko may seem like the average nerdy girl with atrocious social skills; however, she harbours a disturbing secret: she has multiple personalities and when she sneezes, Touko becomes Genocider Syo, a sadistic serial killer with an affinity for handsome young men. Ironically, Touko is incredibly squeamish and cannot stand the sight of blood and she faints upon seeing large amounts of blood, giving Genocider Syo the space to do some damage.

In addition to being a sadistic serial killer, Touko as Genocider Syo exhibits fairly masochistic traits, such as carving up her own leg after each new victim. Despite Genocider Syo being a “dark side” to Touko’s personality, the masochism is a trait they share and Touko often fantasizes about being punished in some way by Byakuya Togami, her “ideal boyfriend”. Her obsession with Togami goes to the point of her justifying some of the harsh things he says to her, believing them to be his expression of concern for her wellbeing. When he told her to take a bath because she “stinks”, she grinned from ear to ear, asking Naegi if he believes that there is hope for her & Togami’s “relationship”. That’s what love is all about!

Employed by the Prime Minister as one of the four Rakshasa Demons, Suzuka is a character able to manipulate her body. She fights by controlling the growth of her nails, turning them into sharp blades. Suzuka is a capable fighter, but not one without strange tendencies. In a fight against a group of spies, Suzuka deliberately received their blades in order to experience the pain, something she craves.

Suzuka is an outright masochist who seeks her pleasure in combat. Out of combat, it isn’t unlike Suzuka to fantasize about experiencing intense pain and at some point when she was sent to the torture chamber, she managed to even fantasize about being tortured by General Esdeath. Like the other Rakshasa Demons, she enjoys her battles, whether that is a result of her masochism is unknown.

It almost seems like characters with “Inu” in their names doggedly hide some of the most disturbing secrets. Except in this case, it isn’t quite a secret. Meet Inugami Yachiyo, a cat-lover who makes friends with one Nekoyama Suzu, a dog-lover. They end up being proof that opposites attract, as they become friends.

Inugami often proclaims her masochism and explained her love of cats by saying that she prefers “getting disciplined” over “disciplining others”, a clear nod to her masochistic tendencies. In one fairly hilarious case, Inugami drools in anticipation of being forcibly silenced by the school committee chairman, Sarutobi Sora and having made Sarutobi angry, Inugami playfully suggests that if she is going to express her displeasure, she should do it in a way that’ll get Inugami “hot and bothered”. 

When bookworm Harumi Kazuhito takes a bullet for his favourite author Natsuno Kirihime, he is reincarnated as a dachshund and suffers a life without books, until Kirihime herself offers to help him. Now banded together with his favourite author, he accompanies her to a strange woman’s office, where he meets Hiiragi Suzuna; Kirihime’s editor and the woman responsible for the publishing of Kirhime’s Seven Deadly Sins novel series.

As good at her job as she may be, Hiiragi is a hardcore masochist who derives pleasure from any form of abuse, especially that which comes courtesy of Natsuno Kirihime. When introduced in the series, Hiiragi’s eccentricism is quickly introduced but followed by her masochism, highlighted when in one of their scheduled meetings, Hiiragi makes a comment about Kirihime’s small breasts, provoking an angry slash with a pair of scissors from Kirihime. Instead of being scared or retaliating, Hiiragi responded with an ecstatic “Thank you!”, commenting that Kirihime’s scissors are “lovely as usual”, implying that Hiiragi had enjoyed similar attacks before. It’s important to do what you love, but Hiiragi may be enjoying her 9 to 5 a bit too much. 

Konosuba follows the adventure of Satou Kazuma, a hikkomori who died a pathetic death on his way back from buying a limited-edition online game. In the afterlife, he meets the goddess aqua who gives him two choices: head on over to Heaven, or reincarnate in a fantasy world, like in an RPG! Now, given a second chance at life, is Kazuma the hero his new world needed? Or is he just another average adventurer?

Like in an RPG, Kazuma decides to form a party and one of the members of his party is the beautiful Darkness, the crusader. When in battle, Darkness’ masochism kicks in and she often charges into the brunt of the opponent’s attack, hoping to take most of the damage and she seems to derive her pleasure from both physical and verbal abuse. Darkness goes to great lengths to sate her appetite for pain, sometimes “heroically” diving head first into dangerous situations to “protect” others, such as during the Flying Cabbage Harvest, when she shielded fellow adventurers from a flying cabbage onslaught, relishing the physical pain and the stares of the male adventurers present. Darkness: her attacks hardly ever hit their mark, but she’s very good at becoming a wall! 

Having originally hated humans due to the deaths of her parents, Ruby has since changed her stance towards human beings, perhaps due to the influence of the protagonist, Tsukune. Ruby is a witch who works under the board chairman at Youkai Academy doing a variety of odd jobs throughout the series. First warning sign: Ruby lives to take orders from others. Second warning sign: Ruby has a crush on Tsukune and calls herself his “toy”.

Surely two warning signs isn’t enough to call Ruby a masochist, right? Wrong. When helping Tsukune with his training to control his Youkai power, Ruby displayed several perverted traits, masochism being one of them. She often asked to be tortured or punished by Tsukune during this training, showing herself to be one of the most perverted girls in Tsukune’s harem. It’s always those quiet ones.

Sarutobi Ayame, or Sa-chan, was a ninja in training in the Oniwabanshuu, as well as an assassin in training and a waitress part-time at the Kunoichi Café. Despite her line of work needing her to be extremely meticulous, Sa-chan has terrible eyesight and cannot tell an inanimate object from a living one without her glasses. She has an obsession with the series’ protagonist, Sakata Gintoki. Sa-chan consistently displays a degree of perversion, especially with Gintoki.

Due to her infatuation with Gintoki, Sa-chan is often seen stalking the samurai. To her delight, Gintoki treats her very badly, often calling her “dirty woman”, appealing to the perverted masochistic Sa-chan. In one case, Gintoki managed to snatch Sa-chan’s glassess off of her face without her noticing. He then commented that she needed to be more careful and vigilant. Knowing just how horrendous her vision is without her glasses, Sa-chan asked Gintoki to “bully” her more, a reaction which leads us to believe that she not only enjoys being treated badly, but also enjoys being relatively blind at the hands of Gintoki too. Another thing worth noting his her perseverance; she never wavers in her pursuit of Gintoki despite being flat-out rejected at every turn. Could it be true love? Or could it just be the M-Effect?

As a Celestial Wizard, Lucy forms contracts and friendships with the spirits under her control and each one bearing its own abilities and quirks. It is of no surprise that the spirit hiding behind the Gate of the Maiden has some interesting characteristics herself. Virgo is one of Lucy’s most reliable spirits, despite having a very questionable passion…

Virgo seems to enjoy being punished, so much so that whenever she is summoned, she enters the fray with a timely: “Would you like to punish me, princess?” Another warning sign is the presence of shackles on both her hands, a reference to slavery. Virgo might only be joking, but due to her stoic nature, we may never know…

Sprinting her way into the number one spot on our list of pain-popping dames is Kanbaru Suruga from the Monogatari Series, a series which follows Araragi Koyomi and his knack of running into and subsequently helping various girls who are affected by supernatural oddities. Naturally, Kanbaru Suruga is one such girl and energetic and heavily social as she is, Kanbaru often enjoys casual banter with Araragi, banter which always harbours suggestive, sometimes masochistic undertones.

Kanbaru is a very liberated character when it comes to her sexuality and considers herself, in addition to being a masochist, a fujoshi and a lolicon. At one point, Kanbaru playfully answers a phone call from Araragi, claiming to be his “love slave”. Despite being homosexual, Kanbaru has no qualms about flirting with Araragi, and possibly other males. It is this very liberated nature which unsettles Hanekawa Tsubasa. Nevertheless, we love this athletic pervert and coupled together with an intense jealousy, Kanbaru’s masochism makes her one of the darker characters on this list.