Hi, We will try to help you in the best way possible. First of all, it s sad to know what your boyfriend had been going through lately. Based on the history you have shared, he needs to be reviewed by an infectious disease specialist and may need cultures and sensitivity tests after swab taken from penis tip. Local application of antibiotics and personal hygiene with good diabetes control along with oral antibiotics may be needed for proper treatment. Circumcision is recommended to avoid future infections once acute phase settles. Hope I have answered your query. Let me know if I can assist you further. Take care Regards, Dr Saddiq Ulabidin, General & Family Physician