D-Frag!, Bokura wa Minna Kawai-sou Recommendations
A relatively normal guy has to put up with a bunch of weird girls who like to mess with him as well as a masochistic pervert "friend." The main girl in both is voiced by Hanazawa Kana.
Both of the male MC got dragged into bizarre place and have to play tsukkomi role
MC's guy friend both masochist