Smegmatic pseudocysts are a source of clitoral pain and dyspareunia, contributing to sexual dysfunction. Its presentation as a large, painful clitoral mass and its non-surgical management have not been described. A patient in her 40's presented with clitoral pain, dysuria, dyspareunia, and a 2-cm clitoral mass. On examination, the mass was found to be a smegmatic pseudocyst collection and was expressed safely. The smegma also returned positive for Pseudomonas aeruginosa She completed a 7-day course of levofloxacin, and at subsequent follow-ups, her pain resolved. For prevention, she was counseled on appropriate hygiene and topical estrogen use. With this presentation, a thorough physical examination is warranted to rule out smegmatic pseudocysts. Once superinfection has been confirmed, treatment with the appropriate antibiotics can help with symptomatic relief. Additionally, in-office expression can be considered for immediate pain relief. Infected smegmatic pseudocysts can be safely managed conservatively, reducing unnecessary surgical procedures for removal.