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On the other side of this issue, I know it can be a tough thing for a guy to deal with.
When a guy thinks about "other men who have had sex with my gf/wife/whatever in the past", our brains generally lock up at "other men who have had sex with my gf/wife/whatever" and don't get to the "in the past" part. It can be tough to separate it out. We know that the past is the past, and generally speaking try really hard not to let it bother us. I can't really speak for this particular dude, it sounds like you two have a lot of other things going on too if you're looking for ways to "get" him, thinking that the "backlash will be worth it".
Sit down with him and talk to him and tell him you totally understand what the deal is with it. Tell him how you really feel about him; tell him what you told us, that this issue is starting to piss you off. Tell him it hurts your feelings and your self-esteem for him to rant about you like that. And quite honestly, if he replies that you SHOULD feel bad about it, tell him to take a hike.
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Anamnesis
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