This follow-up study evaluated the outcome of sex reassignment as viewed by both clinicians and patients, with an additional focus on the outcome based on sex and subgroups. Of a total of 60 patients approved for sex reassignment, 42 (25 male-to-female [MF] and 17 female-to-male [FM]) transsexuals completed a follow-up assessment after 5 or more years in the process or 2 or more years after completed sex reassignment surgery. Twenty-six (62%) patients had an early onset and 16 (38%) patients had a late onset; 29 (69%) patients had a homosexual sexual orientation and 13 (31%) patients had a non-homosexual sexual orientation (relative to biological sex). At index and follow-up, a semi-structured interview was conducted. At follow-up, 32 patients had completed sex reassignment surgery, five were still in process, and five—following their own decision—had abstained from genital surgery. No one regretted their reassignment. The clinicians rated the global outcome as favorable in 62% of the cases, compared to 95% according to the patients themselves, with no differences between the subgroups. Based on the follow-up interview, more than 90% were stable or improved as regards work situation, partner relations, and sex life, but 5–15% were dissatisfied with the hormonal treatment, results of surgery, total sex reassignment procedure, or their present general health. Most outcome measures were rated positive and substantially equal for MF and FM. Late-onset transsexuals differed from those with early onset in some respects: these were mainly MF (88 vs. 42%), older when applying for sex reassignment (42 vs. 28 years), and non-homosexually oriented (56 vs. 15%). In conclusion, almost all patients were satisfied with the sex reassignment; 86% were assessed by clinicians at follow-up as stable or improved in global functioning.