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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.

Kisaragi Amatsuyu is invited out alone by the cool beauty upperclassman Cosmos and his childhood friend Himawari. Expecting to hear their confessions, he triumphantly goes to meet each of them in turn. But Cosmos and Himawari both instead confess to Amatsuyu that they like his friend. Amatsuyu fights this lonely battle, but there is another girl who is looking at him. She is a gloomy girl with glasses and braids. Amatsuyu finds that he hates her, because she's always turning her sharp tongue only on him and finding enjoyment in his troubles. But it turns out that she's the only one who actually does like him.

The original video anime episode will serve as the final chapter to the television series, focusing on the rivalry between the "background character" Amatsuyu Kisaragi (Jouro) and Yasuo Hazuki (Hose), "the protagonist."

The story centers on Nonoha Nonohara, a young manga artist who just enrolled in a new school. She finds herself surrounded by a group of three “super-cute” guys.