An optical stylus and host computing system is provided, as are methods related to the operation thereof. In particular, in an example embodiment, a method of operating the optical stylus is provided that includes determining when the optical stylus is in contact with a surface based on signals received by a processor from a pressure sensor of the optical stylus and capturing an image while the optical stylus is in contact with the surface using a camera of the optical stylus. The captured image is then transmitted to a host system.