A new school year begins at Shin Ara Gakuen, a private middle school, with the arrival of the beautiful and energetic twenty-three-year-old teacher Machiko Mai. From her first day, Machiko-sensei quickly becomes the most popular teacher on campus, particularly with the boys, due to her kind, patient nature and her famously revealing bubblegum-pink miniskirt. However, this popularity comes with a near-constant stream of chaos. The students, led by the mischievous Kenta Ikegami, take delight in devising elaborate traps to lift her skirt, catch her in various states of undress, or otherwise create accidental sexual situations. Rather than punishing the boys or reacting with anger, the good-natured Machiko simply laughs off the humiliation, covering her face and uttering her trademark phrase, Maicchingu! an expression of embarrassed exasperation.

This premise is the foundation for a long-running series of live-action films produced primarily by Total Media Corporation and King Records. The earliest live-action adaptations feature Kaori Nakata as Machiko, with Minoru Kawasaki directing the first two films released in 2003. The third film in 2004 saw Haruka Nanami take over the role, again under Kawasaki's direction. The following year, a different production team released Maicching Machiko! Begins, a new take directed by Kosuke Suzuki with Sayaka Isoyama as the titular teacher. The narrative continued in 2006 with Maicching Machiko-sensei: Toudai o Juken Dai Sakusen!!, a theatrical film starring Hanako Nanjo and directed by Minoru Kawasaki, which focuses on a comedic scheme involving entrance exams for Tokyo University.

Beyond the core dynamic of mischievous students and their forgiving teacher, the live-action series develops its own storylines and recurring characters. A notable subplot involves a rivalry between Machiko's colleagues, teachers Yamagata and Kagoshima, who both compete for her affections. In one specific live-action DVD titled Kimodameshi de Maicchingu, Machiko attends summer school with her students. The trip descends into supernatural chaos when a student is cursed by a female ghost during a test of courage. Selflessly, Machiko asks the spirit to transfer the curse to herself. While trying to help the ghost find peace, it transforms into an evil spirit, forcing Machiko and the students to save her. The franchise continued well into the late 2000s with actresses Yuri Morishita and Hitomi Aizawa portraying Machiko in sequels directed by Tenkaku Naniwa and Chu Ueda respectively.

Almost a decade later, a new live-action film, Hatsukoi Sketch ~Maicching Machiko-sensei~, was released in September 2018. This version takes a slightly different approach, focusing on a student's crush. Reimi Ōsawa stars as Machiko, while Jum Murakami, a member of the comedy duo Shizuru, plays Kenta, who has harbored feelings for his teacher since middle school. The film follows their interactions as Kenta navigates his first love.