By using Kerr electro-optic technique, electric field in oil / pressboard (PB) composite insulation system, which is the typical insulation system of a transformer, was investigated at polarity reversal of HVDC voltage. When the applied voltage polarity was sharply reversed, the applied electric field was superimposed by the electric field of accumulated charges on PB, and very strong field appeared right after the polarity reversal. This could cause the discharge in the oil gap and on the PB surface. The critical value of the discharge initiation at the polarity reversal was verified to be determined by the sum of the applied electric field and the electric field of accumulated charges on PB. The discharge was observed by a high-speed video camera. It was clarified that the surface discharge on PB did not overlap with each other, which was explained by that the surface discharge could neutralize the charges on PB.