Penile Mondor's disease, or dorsal vein thrombophlebitis, is vital for urologists to recognize. It causes pain and hardening in the penis due to triggers like trauma or neoplasms. Distinguishing it from similar conditions such as sclerosing lymphangitis and Peyronie’s disease is crucial. Penile Doppler ultrasound is the preferred diagnostic method. Providing reassurance can ease patient anxiety. This case report highlights a unique occurrence following forceful condom removal during sex, detailing symptoms, diagnosis, and successful treatment.