You ask how "bad". I never thought it bad. As far as frequency of him dressing up it was not every day but usually at least a few times a month, I think. I enjoyed stroking his erect penis while he wore undergarments though we did not have intercourse then. But a lot of talking dirty and teasing and I would strip tease for him.

He and I were a good match sexually. I had several sexual partners before him but I was only multi-orgasmic with him.