Introduction: While prostate cancer is the most common malignancy in men, cutaneous penile metastases are rare and indicate a poor prognosis. Case Presentation: A 63-year-old man with painful non-healing penile lesions was referred to our unit for workup. Clinical examination revealed indurated ulcerative lesions with bilateral inguinal lymphadenopathy. Incisional biopsy of the penile lesions confirmed metastatic adenocarcinoma with NKX3.1 positivity, indicating prostatic origin. Further workup showed a blood serum PSA level of 489 ng/mL; prostate biopsy confirmed Gleason Grade 8 prostate cancer, and bone metastases were seen on plain skeletal radiography. A bilateral orchidectomy was performed, and he was started on docetaxel chemotherapy and zoledronic acid. Conclusion: The multidisciplinary management of this case resulted in regression of the metastatic lesions at his six-month follow-up, with no new cutaneous lesions observed.Keynote message: Cutaneous penile metastases from prostate adenocarcinoma are a rare manifestation of advanced disease and are linked with a poor prognosis. This case highlights the importance of careful clinical evaluation of persistent penile lesions, as early recognition and multidisciplinary management are essential for oncological treatment and symptom control.