Penile fracture is a very rare urological emergency resulting from the traumatic rupture of the tunica albuginea of one or both corpora cavernosa. Immediate surgical treatment is the current standard of care with lower risks of late complications, including erectile dysfunction, penile curvature, and tunical scar formation. We report a case of a patient with sexual dysfunction who took a combination of Anafranil and Sildenafil to enhance his sexual performance to satisfy his girlfriend, but ended with a penile fracture. Our case exposes the degree of frustration suffered by patients with sexual dysfunction and the extent to which they can go in the quest for a solution to their problem, the outcome may be unfavorable.Patients should be informed about the possible complications of Sildenafil either used singly or co-administered with Anafranil for improved sexual function, and recreational use of these drugs should be discouraged.