Ten years ago, "the Gate" appeared and connected the real world with the realm of magic and monsters. To combat these vile beasts, ordinary people received superhuman powers and became known as "Hunters." Twenty-year-old Sung Jin-Woo is one such Hunter, but he is known as the "World's Weakest," owing to his pathetic power compared to even a measly E-Rank. Still, he hunts monsters tirelessly in low-rank Gates to pay for his mother's medical bills. However, this miserable lifestyle changes when Jin-Woo—believing himself to be the only one left to die in a mission gone terribly wrong—awakens in a hospital three days later to find a mysterious screen floating in front of him. This "Quest Log" demands that Jin-Woo completes an unrealistic and intense training program, or face an appropriate penalty. Initially reluctant to comply because of the quest's rigor, Jin-Woo soon finds that it may just transform him into one of the world's most fearsome Hunters.

In a hidden school surrounded by mountains, young ladies of good families are taught everything a high class lady needs to know. They are also completely cut off from the outside world, keeping them sheltered and innocent; however, a problem has come up recently—more and more graduates are failing to cope with the modern world after graduation. To deal with this problem, they've decided to kidnap a male commoner student, and enroll him as a student. They hope that this will be a gentle way to introduce the girls to the outside world. Kagurazaka Kimito is chosen for this dubious honor, mostly because he seems utterly average; however, the school leaders also seem to have concluded he's a homosexual with a muscle fetish. When Kimito hears that the alternative may be castration (to protect the girls' purity), he eagerly plays along with this misconception. Now he'll just have to survive the attention of many high class young ladies that are completely out of touch with the world!

Suzuka Nagami is a beautiful third-year middle school student who has excellent grades and is the student council president. She wrote a novel about a little sister who dotes on her older brother, and the the novel wins a light novel award. After they discuss the matter, Yuu is the one who debuts as a proxy light novel author instead of Suzuka, under the pen name Chikai Towano.

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Gouda Takeo is a freshman in high school. (Both estimates) Weight: 120kg, Height: 2 meters. He spends his days peacefully with his super-popular-with-girls, yet insensitive childhood friend, Sunakawa. One morning, on the train to school, Takeo saves a girl, Yamato, from being molested by a pervert. Could this be the beginning of spring for Takeo?

With his muscular build and tall stature, Takeo Gouda is not exactly your average high school freshman. However, behind his intimidating appearance hides a heart of gold, and he is considered a hero by the boys for his courage and chivalry. Unfortunately, these traits do not help much with his love life. As if his looks are not enough to scare the opposite sex away, Takeo's cool and handsome best friend and constant companion Makoto Sunakawa easily steals the hearts of the female students—including every girl Takeo has ever liked. When Takeo gallantly saves cute and angelic Rinko Yamato from being molested, he falls in love with her instantly, but suspects that she might be interested in Sunakawa. With his own love for Yamato continuing to bloom, Takeo unselfishly decides to act as her cupid, even as he yearns for his own love story.

The true end arc of Ore no Imouto. These four episodes branch out after the 11th episode of the main TV series and present an alternative version to the end of the TV series. These episodes contrast with the good end arc of the TV series, which was an original ending written for the anime, and instead closely follows the original story from the light novels.

Short specials featuring chibi versions of OreImo characters, included on the first limited editions of the OreImo Season 2 BD/DVD volumes.

Unaired TV episode bundled with the light novel's volume eight.

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Teppei, brought up by his father in the mountains, is an energetic boy who is as tough as weeds and acts as free as a bird. His life changes completely when he enrolls in high school, the first school he has ever attended. Despite his eccentric behavior and being a constant source of troubles, he is soon recognized for his talent in sports—especially in Kendo (the Japanese swordplay art)—and becomes the school's hero.