In a genre boasting its fair share of uncomfortable series, Diabolik Lovers sits among the most unsettling of the bunch. Harem and shoujo always incorporate certain tropes; the central girl, who tends to lack much of a personality so she can serve as a stand-in for the audience, is stuck in a constant battle against a wide range of guys vying for her attention. It is not out of the ordinary for one of the dudes to be a masochist.

Diabolik Lovers opts to go in a different direction. Yui Komori is sent by her father to live in a mansion belonging to six brothers. Unbeknownst to the girl, the Sakamaki siblings are actually vampires and Yui is meant to be their next sacrificial bride. Viewing the protagonist as nothing more than a meal ticket, the brothers physically and psychologically torment the poor girl into submission. Yui enters the mansion as your average teenager, but she leaves it as the siblings' dog.

Permeated with a deranged sexuality that never truly feels appreciated by Yui, Diabolik Lovers seems to get pleasure out of torturing this sweet girl for the guys' amusement.

With the exception of shows that love to torture their protagonist, most anime introduce one character with masochistic traits. People are free to partake in whatever consensual behavior they see fit, but masochism is a relatively unconventional desire. When chiefly employed for comedic purposes, over-reliance on such a passion would lead to diminishing returns, as masochism is only funny when treated as abnormal by the rest of the cast.

A self-proclaimed doll lacking much in the way of emotion, Kohina summons Kokkuri-san out of sheer boredom, but the fox ghost feels sorry for the girl and decides to watch over her. Apparently, Kohina is simply a magnet for ghosts, as she quickly attracts a handful of other spirits. A former dog who was shown kindness by Kohina, Inugami, is part of her collection and the ghost completely embraces the life of a masochist!

One could describe Inugami as the quintessential masochist. Visibly deriving pleasure from the thought of being scolded by his master, Inugami goes out of his way to craft situations that might result in Kohina having to punish her dog. An unabashed pervert, Inugami refuses to hide who he is.

An incredibly twisted series with a diverse roster of characters, Danganronpa may not explicitly feature a masochist, but the entire premise boils down to constantly torturing teenagers in a strange game. Hope's Peak Academy is hailed as an elite high school for only the most gifted students, but this construction merely serves to mask the dark underbelly hidden by the academy's seemingly conventional corridors.

Trapped by a sadistic bear named Monokuma, fifteen students are forced into a death match. The only way out is to murder one of their colleagues, but the perpetrator would be executed if caught by any of the other students. Danganronpa's entire entertainment factor comes from watching these teenagers constantly struggle to break free.

Across multiple seasons, there are a number of characters who derive pleasure from emotional distress. To avoid going into spoilers, Danganronpa generally presents a more philosophical style of masochism, with the recipient desiring to experience despair rather than simply pain.

A somewhat underappreciated gem from yesteryear, Mahoraba: Heartful days is a laugh-out-loud comedy centering around a myriad of peculiar personalities. Accepted into a vocational school for young artists, Shiratori Ryuushi moves into a new apartment and instantly falls for his landlady. At first glance, Kozue Aoba seems utterly normal, but her temperament changes depending on the emotion she is feeling at the time. However, none of Kozue's alter-egos are masochistic, so she is not the reason Mahoraba: Heartful days landed a place on our list.

Erika Vermillion is a terrifying delight. Describing the occult research lab's club president as a masochist would be incorrect, as she also appears to reap pleasure from inflicting pain. Left without a name until the final episode, Erika drifts in and out of Ryuushi's life and constantly praises Tamami's violent behavior. Speaking of sadomasochists, Tamami also fits the bill! Despite appearing to be an average school girl, Kozue's classmate loves nothing more than to embarrass her friends or torture those she deems to be her subordinates.

Starring anime's least spiritual angels, Panty and Stocking are known as the Anarchy sisters. Due to their mischievous antics and refusal to obey the laws of heaven, the titular heroes find themselves banished to Earth's Daten City and tasked with exterminating any ghosts who slip through the cracks. While more than capable of defeating most opponents, Panty and Stocking tend to neglect their duties in favor of pursuing hedonistic diversions.

Chosen to set them straight, Garterbelt is a priest who talks a good game but might actually be even lewder than the sisters. Due to his past as a gangster, Garterbelt seeks atonement by pursuing absolute self-control. On paper, this sounds like a noble objective, but it is mostly an excuse for the priest to indulge in some BDSM. Seeking to keep this aspect of his personality a secret, Garterbelt creates an alter-ego named Master G so he can be free to practice "self-control" to his heart's content. Admittedly, the priest's preference for young males is a point of concern.

A deconstruction of the isekai subgenre, Kono Subarashii Sekai ni Shukufuku wo! is a comedic tour-de-force! Based on Natsume Akatsuki and Kurone Mishima's light novel series, Studio Deen crafted a nearly flawless adaptation. Dying of shock, Kazuma is mocked by the arrogant goddess Aqua, but this stunt soon proves to be her undoing. Prior to being reincarnated in a new world, Kazuma is allowed to take a single object with him, so the NEET opts for the goddess. Honestly, anything else would have been more useful!

Anyway, Aqua and Kazuma are not the main focus of this entry; no, that honor goes to Lalatina Dustiness Ford. Commonly referred to as Darkness, this powerful crusader's high defensive and offensive stats suggest she should be an indispensable part of any party. Unfortunately, Darkness cannot land a blow to save her life and seems to enjoy being subjected to attacks far more than anything else. At the very least, she seems to love her job...

Darkness' masochism is comfortably the character's most prominent personality trait, and she regularly works against Kazuma's party to put herself in as much danger as possible.

Fresh out of 2018's summer season, Jashin-chan Dropkick breathes gory violence. Based on a web manga by Yukiwo, Yurine is a delusional lolita who summons an obnoxious demon girl named Jashin-chan. Tied together for the foreseeable future, the devil decides that the only way to escape her newfound hell is to murder the crap out of Yurine. Alas, the best-laid plans of snakes and demons often go awry, and Jashin-chan frequently finds herself on the receiving end of a beating.

With the two central characters clearly cherishing the thought of torturing their roommate, sadomasochism is the name of the game. Unable to avoid firmly putting her foot in her mouth, Jashin-chan grasps every available opportunity to demean other people. As Yurine is far too terrifying to purposely annoy, Jashin-chan usually shifts her attention to the timid Medusa.

Jashin-chan is not the only monster in attendance, as Yurine practically has an orgasm whenever she retaliates against the demon. Be it a chainsaw or a crowbar, the goth girl employs an impressive toolkit to make the most of any such occasions.

Is there a better way to educate someone than by beating them to death with a spiked club? Among the first of its kind, Bokusatsu Tenshi Dokuro-chan is arguably the most infamous anime to derive its comedy from repeatedly torturing its protagonist. The attacks amount to far more than the occasional slap or stomp, as Bokusatsu Tenshi Dokuro-chan features multiple death scenes per OVA. Bordering on revolting, one would almost have to be a masochist to watch this anime.

So, we watched this anime. Does Bokusatsu Tenshi Dokuro-chan earn its notoriety? Oh, most definitely! 20 years into the future, Sakura Kusakabe will create a device that stops girls from hitting puberty. Considered an act against the heavens, the angel Dokuro Mitsukai is sent to put an end to the junior high student's existence. Fortunately for Sakura, Dokuro believes in rehabilitation; unfortunately, she thinks the best approach is to constantly kill and revive Sakura until he no longer possesses the will to create the loli machine.

The characters themselves hardly endure any pleasure from their violent acts, but the creators clearly had a blast animating Bokusatsu Tenshi Dokuro-chan's more violent moments!

Masochism: the anime. Prison School is a hilarious ecchi series about a group of high school boys who get caught peeping at a boarding school that used to be only for girls. As punishment, the student council locks the guys in a prison for an entire month! Like the manga it is based on, Prison School works due to showing a complete disregard for even a semblance of tact. J.C.Staff's anime holds nothing back and is not afraid to go "there."

While each one of the boys experiences some pleasure from the student council's punishments, Reiji Andou takes the cake! Tall and obese, Andre would not harm a fly and cherishes his friends, but even gentle giants have desires. Easily the captives' most overtly perverted member, Reiji wears his masochistic tendencies on his sleeve. Unable to resist the domineering charm of Risa Bettou, Andre willingly betrays his friends to assist the student council and prolong his pleasure.

When it comes to masochist anime, there was never going to be another contender for the top spot! MM!'s protagonist is a full-blown masochist, and this personality trait drives the plot forward. Rather than being used for a quick laugh or restricted to a secondary character, MM! thoroughly embraces the act of deriving pleasure from pain. Even if the protagonist's goal is to overcome this particular characteristic, Taro Sado's love for torture is an inescapable part of his identity!

Encouraged by his close friend, Taro requests assistance from the Second Voluntary Club, but he ends up being strong-armed into joining their ranks. Lead by the delusional Mio Isurugi, Taro is repeatedly tortured in attempts to force the fetish out of him. Admittedly, this tactic seems somewhat counterproductive but exposure therapy is a thing that exists.

Most of the comedy boils down to Taro's efforts to hide his masochism, but the main character cannot help but have a goofy smile on his face whenever Mio decides to literally stick the boot in!