One such game could be 'Ace Attorney'. It features detective - like elements where you solve mysteries. Although it's not strictly'masochist' in a negative sense, the challenging cases can give that feeling of being put through the wringer as you try to prove your clients' innocence.
I'm not sure specifically as I haven't played it. But generally, detective - themed visual novels often involve solving mysteries, following clues, and uncovering secrets in a story - driven way. Maybe in this one, the 'masochist' part could add an interesting twist to the detective's character or the overall plot.
Typically, it would have a strong detective element, like a complex mystery to solve. For example, there could be a series of murders to figure out. The'masochist' part might mean that the protagonist or the player is put in very difficult situations, such as being constantly doubted or facing dangerous opponents while trying to solve the case.
I don't know the main characters as I haven't read or played it. But it's likely to have the detective as one of the main characters, given the title. And perhaps there are other characters related to the cases the detective is trying to solve, like suspects, witnesses, or other law - enforcement colleagues.
I'm not aware of many visual novels that exactly match this very specific 'student council president masochist' description. However, some visual novels with complex character relationships in a school setting like 'Clannad' could be of interest. It focuses on different personalities and their growth within the school environment, which might give you a similar feeling in terms of exploring unique characters, even if not the exact concept.
One popular detective visual novel is 'Ace Attorney'. It has engaging storylines full of mystery and interesting characters. The player takes on the role of a defense attorney and has to solve cases through investigation and courtroom battles.
Another one is 'Mistress of the Manor'. In this visual novel, players can experience a variety of scenarios where the female characters are in control. The character development is well - done, and it offers different paths depending on the player's choices. There are also interesting dialogues that really capture the essence of the femdom theme.
One of the popular 2003 visual novels is 'Fate/stay night'. It has a complex story with different routes and interesting characters. The battle scenes and the magic system are quite engaging.
One similar game could be 'To the Moon'. It has a touching story with elements of memory exploration and emotional depth, much like many visual novels. Another one is 'Clannad', which is well - known for its complex characters and heart - warming storylines. There's also 'Planetarian: The Reverie of a Little Planet' that offers a unique and engaging narrative experience.
There is also 'Nekojishi'. It combines elements of the supernatural with gay relationships and presents an interesting visual novel experience. The art style is quite appealing and the story is immersive.
One similar game could be 'Clannad'. It also has a strong story - line and interesting characters. Another one is 'Air', which has a unique and emotional plot.