The scope of the invention encompasses novel, multifunctional tools for maintaining the neovagina. The tools comprise novel dilator shapes that conform the anatomical pathway of the neovagina. The tools may further include a douching function for the effective and thorough washing of the neovagina, which is not achieved with standard douching devices. The tools may also comprise a measurement function for medical evaluation of the neovagina and to aid in proper dilation. Also presented herein are novel devices for delivery of agents to the natal vagina, including insemination devices.