The demand for masculinizing breast surgery and hysterectomy with bilateral salpingo-oophorectomy (HBSO) from transmen has increased. With a multidisciplinary approach, these surgeries can be performed in a single session. The objective of this study was to retrospectively evaluate the feasibility, safety, and satisfaction of HBSO and chest surgery in transmen. A cohort of 142 subjects who underwent HBSO alone or combined with chest surgery at Sant’Orsola Hospital was analyzed. Intra and post operation events were evaluated. Subjective post-intervention satisfaction, acceptability, and impact of intervention were assessed via a semi-structured interview. Nineteen transmen underwent HBSO alone and 123 underwent combined surgery. HBSO was performed laparoscopically in 96.5% of transmen (137/142). As expected, length of hospital stay and blood loss were significantly higher in the combined surgery group. A total of 13 intra or post-operative complications occurred in the combined surgery group (10.5%) with thoracic hematoma being the most frequent complication (7.6%). Only one rare complication occurred in the HBSO group (omental herniation through a laparoscopic breach). The overall subjective satisfaction score was 9.9 out of 10 for both groups. Positive changes in all areas of life were reported, with no significant differences. We found that the combined surgery appears to be well tolerated, safe, and feasible in transmen and satisfaction with the combined procedure was high in all subjects.