Introduction: The number of transgender individuals seeking medical and surgical care has increased over the last years. Within the transgender population overweight and obesity is more frequently observed when compared to the general population. Little is known on the prevalence of bariatric surgery in the transgender population and the effects on the surgical gender transition path of the individual transgender with overweight or obesity. Material and methods: All transgender individuals who underwent gender-affirming surgery (GAS) between 1980 and 2020 were retrospectively identified from our hospital registry. Those with a history of bariatric surgery were selected. A retrospective chart study was conducted, recording gender identity, bariatric surgery specifications, gender surgery specifications, complications, reoperations and clinical follow-up time. Results: A total of 15 transgender individuals (11 transgender men, 4 transgender women) who underwent bariatric surgery were identified. All individuals underwent bariatric surgery before any GAS procedure, except for one transgender man. At the first GAS procedure, all individuals experienced significant weight loss when compared to their weight at bariatric surgery (mean 13.1 ± 3.8 BMI points lost for transgender men, mean BMI points lost 14.3 ± 2.8 for transgender women, p < 0.01). Obesity was still frequently prevalent in transgender men after bariatric surgery. All included transgender men underwent mastectomy via the double incision with free nipple grafting technique. Only one transgender man underwent genital GAS. All transgender women underwent penile-inversion vaginoplasty, one in combination with prosthesis-based augmentation mammoplasty. Conclusion: Surgical gender transition is possible after massive weight loss after bariatric surgery. Specific surgical subtechniques will be more prevalent in this population.