A multilevel, inflatable vaginal pessary device is soft, malleable and has a gentle gripping surface to assure retention and proper placement. The pessary device can offer options for pressure, either apically toward the cervix or anteriorly toward the bladder or posteriorly toward the rectum, via an inner silicone elastomeric (such as Silastic® by Dow Corning Corporation) balloon that can variably be filled with air from a syringe attached to a luer lock tip in the balloon. Exposure of the balloon is achieved by the physical opening potential of the fenestrated rings by cutting along guide lines in the pessary sleeve. The physician has multiple options for customizing the device to remedy the patients prolapse.