An intimate pleasure enhancing device 10 (IPED 10) that is presented in four designs that function in combination with an elongated structure (12). The first design utilizes a rear ring (30) that is attached by a first spring (58) to a movable first stimulator (42) located adjacent the front end (14) of the structure (12). The second design utilizes a rear ring (30) and a front ring (82). The front ring (82) is attached to the rear ring (30) by the first spring (58) and a second spring (72). The third design utilizes a front ring (82) that has attached a resilient member (92) located across the first end (14) of the structure (12). The fourth design utilizes a magnetic displacement assembly (104) that utilizes a set of similar polarity permanent magnets (120,134) that cause a front ring (82) to move along the outer surface (18) of the elongated structure (12). The IPED (10) can also be designed to function with a spring roller (150) that allows the first ring (82) to roll over the elongated structure (12).