A 28-year-old male-to-female transsexual presented with a sore throat and difficulty swallowing. Imaging showed an abscess on the left tonsil and thrombosis of the left internal jugular vein, consistent with Lemierre's syndrome. Lemierre's syndrome involves a neck infection leading to internal jugular vein thrombosis and potential sepsis. Estrogen levels in male-to-female transsexuals have been associated with higher risk of blood clots. This case illustrates the importance of monitoring transsexual patients on estrogen therapy for potential complications like Lemierre's syndrome.