Background: Urethral coitus is an extremely rare clinical entity, often associated with congenital vaginal anomalies such as agenesis or hypoplasia. However, it may occasionally occur in women with normally developed external genitalia, presenting with non-specific symptoms like dyspareunia, urinary incontinence, and recurrent urinary tract infections (UTIs). Due to its rarity and sensitive nature, it is frequently misdiagnosed or overlooked. Case Report: A 33-year-old woman presented with dyspareunia, urinary incontinence, and recurrent UTIs during infertility evaluation. Despite normal menstrual cycles and external genitalia, she reported painful intercourse and confusion regarding penetration. Imaging revealed normal uterus and ovaries, with a collapsed lower vaginal segment. Examination under anesthesia identified a dilated, incompetent urethral meatus allowing one-finger passage, with urine leakage, and a small vaginal opening below it. Vaginal dilation was performed, and urethroplasty was advised alongside pelvic floor exercises. She was placed under follow-up for infertility management. Conclusion: Urethral coitus in the presence of a normal-appearing vagina is an underrecognized cause of dyspareunia and urinary symptoms. Early diagnosis through careful history-taking, imaging, and examination is essential to prevent long-term complications such as megalourethra and psychological distress.