A urinary catheter assembly includes a catheter member and a sleeve member receiving at least a portion of the catheter member and having a greater flexibility than the catheter member. The assembly also includes a stylet having a proximal end movably positioned within the catheter member, with a distal portion of the stylet being positioned outside of the catheter member. The assembly is movable between a compact configuration and an extended configuration. In the compact configuration, the distal portion of the stylet is positioned outside of the catheter member and at least partially within the sleeve member. In the extended configuration, a larger distal portion of the stylet is positioned outside of the catheter member than in the compact configuration. The assembly may be in the extended configuration for introduction into a urethra or may be advanced through a urethra prior to being moved to the extended configuration.