Penile fracture is a urological emergency, and surgery is usually recommended to prevent complications. However, proximal locations are scarce and not well investigated. We present two rare penile fractures involving the proximal corpora cavernosa with an original conservative strategy to manage this clinical presentation. Twenty-five- and thirty-eight-year-old men with no previous medical history were admitted to the emergency room for penile trauma during sexual intercourse a few months apart. Both presented with “butterfly pattern” ecchymosis with a palpable hematoma on the perineum. They had no hematuria or voiding dysfunction. Ultrasound found a hematoma and a tear of the proximal corpus cavernosum for the younger one. Then, an MRI confirmed a longitudinal fracture of the right corpus cavernosum for the first patient and left for the second, without urethral injury. In agreement with the patients facing this atypical presentation, we proposed a conservative treatment with analgesics, monitoring, and advice to stop sexual activity for three weeks. After six weeks and four weeks, respectively, we performed a clinical evaluation and a second MRI that found no residual tear or hematoma. The IIEF-5 questionnaire was 24/25 and 25/25. The patients were clinically symptom-free at 8 and 11 months of follow-up. Extreme proximal fracture of the corpus cavernosum can be managed conservatively in selected situations. MRI is useful for decision-making by confirming the diagnosis and location to avoid surgery.