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If the guy can't handle it, he can't handle it. But he has no right to torment his girlfriend and hold it over her head. And the two other people in her past don't qualify as competition. They're IN THE PAST. The only person standing in the way of the LW and her BF is...the BF.
I'm not a good person to ask, though, as I must not be insecure enough. When my sister-in-law asked me why I allowed (!) my husband to keep some pix of his old girlfriends in HIS photo albums, I told her "What difference does it make to me? He married ME". On the other hand, a student who wrote for a local college paper stressed EVERY WEEK that it was best to be a virgin when you married because you wouldn't compare the guy/girl to someone else and that the hottest sex ever was between two virgins because there was none of that icky comparison business going on. It was obvious to every one but him that he had some serious performance anxiety. The LW's BF sounds like that guy's kid brother.