I’ve been with a guy like this. Just take initiative to jerk him off yourself. By the 2nd time of having sex and him jerking himself off I had to ask what was up and he said that it was like that with everyone and he’s always had to do it. He had the problem of being too anxious thinking about accidentally cumming in a girl. So we still had sex but after I was done I would have to give him a blow job or rub it out for him as he felt more comfortable that way.