A high-school/college, where such a prank/act would realistically take place.

A horror setting, such as an abandoned house or lonely woods, where the most unfortunate/ironic events can occur.

Inside a single person's home, where the duration of the wedgie(s) are driven purely by the giver.

A superhero world/setting, where the punishment can be pushed to more extreme levels.

An otherworldly/magical setting, where a person's worst fears can be exploited.

A sports environment, like a stadium or training ground, where the equipment has also sorts of uses.

A public park or garden, where the victim can be exposed to the world.

An adventure setting, like a mountain path or cave, where one's humiliation cannot be stopped.

Other (please comment)