I would venture a guess that he is infected somewhere, yes. And even if his screening test is negative for HSV 1, I still think he has it. The screening test for HSV 1 is not the greatest. If he has genital HSV 1, he won’t get your HSV 1 from giving you oral sex. If he does test negative for HSV 1 and is worried that he might not really be infected, a western blot can help clarify that. The screening test misses 1-2 out of 10 infections.
I would not worry about having any kind of sex with him. It seems to me you are now both infected with HSV 1 and you are home free.
Yes you could have acquired HSV 1 in both places, did you have oral symptoms? In my experience, people who contract it in both places do have symptoms in both places of some kind. I am assuming you did not have oral symptoms.