Flexible sensing styluses deliver additional degrees of input for penbased interaction, yet no research has looked into the integration with creative digital applications as well as the influence of flexural stiffness. We present Hy-perBrush, a modular flexible stylus with interchangeable flexible components for digital drawing applications. We compare our HyperBrush to rigid pressure styluses in three studies, for brushstroke manipulation, for menu selection and for creative digital drawing tasks. HyperBrush yields comparable results with a commercial pressure pen. We concluded that different flexibilities could pose their own unique advantages analogous to an artist's assortment of paintbrushes.