Dermoid cysts are subcutaneous swellings that are usually congenital and originate from the sequestration of embryonic epithelium along the lines of embryonic closure. They are composed of a mixture of sebaceous fluid, keratin, cholesterol crystals, calcium, hair follicles, sweat glands, and sebaceous glands. They present as a non-tender mass that is well-circumscribed, firm in consistency, and usually asymptomatic. Occasionally, dermoid cysts can get infected and form an abscess. Surgical excision remains the linchpin of treatment for dermoid cysts. Dermoid cysts are most common on the head, face, neck, and thoracoabdominal region and are very rare on the prepuce (foreskin). We report the case of a 27-year-old male who presented with a midline penile mass, difficulty in retracting his prepuce, and painful intercourse. A basic hematological and radiological workup was done to rule out the other differentials. Surgical excision of the swelling was done, and a histopathology report proved it to be dermoid. This case report highlights the possibility of the presence of a dermoid at rare anatomical locations such as the penis.