Background and Objectives: This retrospective analysis investigated the impact of preparation of the pelvic floor for childbirth with stretching balloons and perineal massage on the risk of pelvic floor injuries. Materials and Methods: We analyzed 150 primiparous women who accessed private clinics in Padua (Italy) in the period 2019-2023 regarding the rate of perineal trauma and postpartum dysfunction across three groups: the balloon stretching group (BSG, N = 50, 33.3%), the perineal massage group (PMG, N = 39, 26.0%), and the control group (CG, 61, 40.7%). Results: Prenatal perineal training had a significant impact on reducing the rate of perineal injury and episiotomy (27.5% in BSG vs. 48.7% in PMG and 68.3% in CG, p = 0.008, respectively, 9.8% vs. 26% and 40%, p = 0.046) and the duration of the second stage of labor (BSG and PMG had a shorter duration compared to CG with a mean difference of -0.97892 h, p < 0.001, respectively, -0.63372 h, p = 0.002). Patients who carry out the preparation with the stretching balloon are less likely to develop urinary and anal incontinence and pain during intercourse. Specifically, the rate of urinary incontinence in BSG stands at around 23.5% compared to 43.6% in PMG (p = 0.345) and 55% in CG (p = 0.034). Dyspareunia in BSG was detected in 11.8% of cases compared to 35.5% in PMG (p = 0.035) and 61.7% in CG (p < 0.01). Symptomatology inherent to the posterior compartment was reported in 9.8% of cases in BSG vs. 23.11% in PMG (p = 0.085) and 33.3% in CG (p = 0.03%). Conclusions: Stretching balloons and perineal massage can be chosen as tools to prevent and reduce the rates of obstetric trauma during childbirth and to reduce the use of episiotomies as well as protect against the development of dysfunctions of the pelvic floor.