There is provided a device for measuring an inside shape of a vagina, including a device body, operationally connected to one or more movable cheeks, the cheeks movable in a direction substantially transaxially relative to the device body longitudinal axis, and a width indicator, for indicating a distance between opposite faces of the cheeks. There is provided a method for fitting a pessary including inserting a Pessary Caliber (PC) into a vagina, extending cheeks of the PC to press against sides of the vagina, measuring a distance between the cheeks, measuring how deep the PC is inserted into the vagina, and selecting a pessary size based, at least in part, on the measuring. Related apparatus and methods are also described.