INTRODUCTION: The process of transitioning from female to male in transgender persons usually includes medical treatment as well as surgical interventions, including removal of the uterus and ovaries. Nulliparity and prolonged exposure of the vaginal mucosa to testosterone, which are common among transgender men, may present challenges to perform a vaginal hysterectomy with salpingo-oophorectomy. The aim of this study is to describe outcomes of vaginal-assisted natural orifice transluminal endoscopic surgery (vNOTES) approach to perform hysterectomy among transgender men as part of their gender-affirming care. METHODS: This is a case series observational study conducted at single tertiary medical center including all patients undergoing hysterectomy with bilateral salpingo-oophorectomy by vNOTES approach for gender-affirming care between February 2022 and April 2023. Primary outcome was defined as compound complication rate including intraoperative and postoperative. Patients' demographic and clinical charectaristics were collected from the electronic medical files. Pain at postoperative follow-up was evaluated using visual analog scores, which ranges from 0 (no pain) to 10 (worst pain possible). RESULTS: The study population included eight transgender men, all of whom were nulliparous and had undergone testosterone treatment for more than a year. Median age at surgery was 24 years and median body mass index was 30 kg/m2. Mean operative time of the surgery was 111 minutes (range: 91–143 minutes) and none required converting from vNOTES to an alternative approach. No extensive bleeding or organ damage was reported. For one patient, there was one small vaginal laceration requiring suture. All but one patient was discharged the same day. The patient requiring next-day discharge was complicated by postoperative urinary retention. On postoperative follow-up, median pain score was 3 (range: 1–5). CONCLUSION: Outcomes from this case series suggest that a vNOTES approach to hysterectomy among transgender men can be performed without surgical complications and with low self-reported pain.