A delivery device for deploying an insertable into an orifice guided by a digit includes: an insertable orientation means having a first longitudinal axis and a base portion, the insertable orientation means adapted to load an insertable positioned in a deployment orientation, and a skirt member extending from adjacent the insertable orientation means and having a skirt length and comprising opposing digit contacting and orifice contacting surfaces, wherein the skirt member is adapted to be movable substantially parallel to the first longitudinal axis and along the skirt length, between: an insertable surrounding configuration, wherein an orifice contacting length of the orifice contacting surface substantially faces the insertable orientation means and any loaded insertable; and a digit surrounding configuration, wherein the orifice contacting length of the orifice contacting surface substantially faces away from the insertable orientation means and any loaded insertable.