Purpose and Methods Scrotal and perineal squamous cell carcinoma (SCC) is an uncommon and aggressive skin cancer predominantly affecting older men. This study presents the case of a 48-year-old male with a 7-month history of an enlarging ulcerating skin lesion on the scrotum and perineum. The patient, a long-term smoker with no occupational or radiation exposure, displayed a large fungating mass with serous discharge and potential infection. Diagnostic assessments, including biopsy, CT, and MRI, were employed to determine the extent of the cancer. Results The initial biopsy revealed an HPV-negative SCC, and imaging studies showed no metastatic or nodal disease. The patient underwent wide local excision, bilateral inguinal lymph node dissection, and a vertical rectus abdominus musculocutaneous (VRAM) pedicled flap in a collaborative urological and plastics procedure. Postoperatively, complications included groin dissection hematoma evacuation and bilateral inguinal seroma drainage. Histopathology confirmed HPV-associated SCC with negative margins and no lymphovascular or perineural invasion. Bilateral inguinal lymph nodes were negative for malignancy, indicating Stage T4 N0 M0. No recurrence was observed at the 3-month follow-up, showcasing positive cosmetic outcomes. Conclusion The study emphasizes the advantages of the VRAM flap, such as a robust pedicle, substantial volume, ease of harvest, and low necrosis risk. Overall, the case underscores the importance of early intervention and prompt management of scrotal lesions, urging individuals unaware of their risk factors to seek medical advice upon noticing suspicious scrotal abnormalities.