Body dysmorphia is a debilitating disorder that centralizes on a preoccupation with one’s physical appearance. Often, these individuals seek surgical correction in an effort to subdue this preoccupation. A majority of complications from feminizing gender reassignment surgery, consists of urethral stricture or stenosis, leading to voiding dysfunction. The patient is 39-year old male who underwent bilateral nipple removal, bilateral orchiectomy, scrotectomy and total penectomy with perineal urethrostomy, one year prior to consult. The patient eventually presented with acute urinary retention secondary to perineal urethrostomy stenosis. Urethroplasty with revision of perineal urethrostomy site using a buccal graft was done; and on follow up, he was noted to have good urine flow on uroflowmetry with mild lower urinary tract symptoms. Complex urethral strictures may be noted in patients with prior reconstructive history and lengthy areas of fibrosis. Although perineal urethrostomy is a valid surgical course of treatment for patients with complex strictures, improper technique, suboptimal patient factors, and, poor healing may lead to stenosis. The study aims to describe the use of a buccal graft as a viable alternative and easily reproducible technique to augment a revision perineal urethrostomy and lessen the recurrence of stenosis.