Second season of Higeki no Genkyou to Naru Saikyou Gedou Last Boss Joou wa Tami no Tame ni Tsukushimasu..

With the tumultuous cultural festival behind him, Masamune Makabe continues his efforts to carry out his revenge: to make the Cruel Princess Aki Adagaki deeply fall for him and then immediately dump her. As his class is going on a trip to Paris, widely known as the City of Love, Masamune has the perfect opportunity to get even for his childhood heartbreak. Before Masamune can impress Aki, the two meet Muriel Besson, a French high school otaku who aspires to create a romantic comedy manga series. Muriel believes Masamune is the ideal model for the protagonist and asks for his help. The boy reluctantly agrees, dragging Aki along to provide inspiration for the love interest's character. But to do so, the two must show Muriel what Japanese love is like. To make matters more complicated, Kanetsugu Gasou is masquerading as Aki's childhood friend, Masamune, to trick and use her. With mix-ups and love rivals galore, Masamune's revenge is proving to be quite the difficult task.

Uchi no Mama ni Kagitte (Of Course, My Mom...) Upon returning home from school one day, Masamune Makabe is joyfully greeted by a young girl who he mistakes for his ever-cheerful mother. However, he quickly learns that she is actually his cousin Haruka! In fact, Haruka, his mother, and his Aunt Asae all happen to look strikingly similar to each other. Seizing the chance to reap the benefits of the situation, Masamune's sister Chinatsu persuades the three to dress up and have some fun. Tsunade Shima, Futatabi. (Tsunade Island, Once More.) Aki Adagaki invites Neko Fujinomiya, Tae Futaba, and Kojuurou Shuri back to Tsunade Island for another round of summer leisure. Missing from the trip is Masamune, who had injured himself by walking into a pole. His absence happens to evoke mixed feelings amongst the group, even perhaps a sense of loneliness. 12-Ji wo Sugita Cinderella (Cinderella After Twelve) Yoshino Koiwai is given the day off after completing her work at Tsunade Island. With the help of her sister, she receives a complete makeover and is involuntarily led to enjoy the opportunity away from her arduous maid duties. Despite having the brief freedom to finally indulge herself, Yoshino realizes there is satisfaction through other colorful ways.

When Masamune Makabe was a child, he was rejected by a rich, beautiful girl named Aki Adagaki, who gave him the nickname ''Piggy'' for being overweight. Devastated, Masamune put great effort into working out to improve his appearance. Now a handsome yet narcissistic high school student, Masamune is determined to exact revenge—he will have Aki fall madly in love with him and ultimately reject her the next time they meet. To his surprise, Masamune discovers he has transferred into Aki's school. Setting his plan into motion, Masamune first begins to form a relationship with the ''Brutal Princess'' but, despite his efforts, fails miserably at his initial attempts. Shockingly, when Masamune finally progresses towards his vengeance, he receives a mysterious letter addressing him by his old nickname. Unless Masamune discovers the sender's identity, his plan is doomed before it even starts!