In an information processing apparatus, a virtual object shape storage unit acquires the position of an operation unit, sets a virtual plane at the acquired position in the virtual space, and records the trajectory of the operation unit after the virtual plane is set. The virtual object shape storage unit then obtains a projection trajectory by projecting the trajectory onto the virtual plane, and records the obtained projection trajectory as contour data representing the contour of a target virtual object on the virtual plane. And then, the apparatus acquires a position and orientation of a viewpoint of the user, and generates and outputs an image of the virtual space seen from the viewpoint on the basis of the acquired position and orientation, the virtual space including the virtual plane and the virtual object having the contour represented by the contour data.