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For me, it's obvious that more daring adventures should be player's reward for not sucking and beating current stage. Player should never want to just walk up to enemies and lose, that should not be the driver of ENF. To get the game to work, you need to place the prize scene where heroine is exposed and humiliated in some way after the section that challenges player (but the ENF scene is not a "bad end", bad end is just game over and reset).
The progress player experiences may mean something like beating a level where you wear swimsuit in-doors and don't face students with cameras or disciplinary squad, to wearing risque costumes outdoors and dealing with increasingly rude onlookers, in the end maybe getting to be fully nude and handcuffed or something.
Progress, rewards, risk management, dynamic situations are strong points of video games. You shouldn't waste time making a bunch of bad ends with inconsequential gameplay.
