Tsukihi Phoenix, Part One Episode 8

Koyomi is concentrated on his studies when he is interrupted by Karen who, much by his surprise, is wearing her sister Tsukihi's clothes, displaying an air more feminine than usual. Karen asks Koyomi to introduce her to Suruga knowing that she is friends with him, but he refuses without giving a reason, fearing that she would make a move on his sister. Karen then challenges his brother to a contest, making him promise to comply with her request if he loses. Koyomi then choses the contents of the challenge - she would let him brush her teeth for five minutes without resisting, which she accepts. Surprisingly, both start getting more and more aroused as Koyomi brushes Karen's teeth until Tsukihi barges in demanding an explanation. Despite fearing what punishment Tsukihi has in store for them after she leaves and Koyomi accepting defeat, Karen asks him to continue from where they stopped.