We report a rare case of penile metachronous metastasis of mesorectal adenocarcinoma in an asymptomatic patient, who initially only accepted chemotherapy, but after thirty months underwent total penectomy followed by radiotherapy, due to penile pain caused by ingravescent metastasis. After another cycle of chemotherapy, at five years follow-up from abdominoperineal resection, the patient was free from recurrence. Our case highlights the importance of penile examination during follow-up of many oncologic patients, in order to allow earlier diagnosis with a potential for more conservative penile surgery, also taking into consideration the good response to new oncologic drugs, as in our experience.