Human monkeypox is a viral zoonosis that has recently emerged worldwide. Clinical cutaneous features include papules, vesicles, and pustules. However, atypical manifestations mimicking other infectious diseases are being reported more frequently. We present a 41-year-old man patient with untreated HIV with generalized rupioid crusted ulcerated plaques with perineal ulceration that were found to represent monkeypox and cytomegalovirus infections.