I have the impression that the reason Kate hasn't gotten pregnant in awhile is that she and Jimmy haven't been forced to have sex for quite awhile. I'm not sure the exact reason why Ray might not have done this for awhile, but my impression is that the last time Kate and Jimmy had sex was before his relationship with Tracy started. That was 2 years earlier (both of the young sons seem well older than 2). I have the impression because the act of forced intercourse with Kate that night seems to introduce conflicts in Jimmy's relationship with Tracy that didn't exist before.
At one point Tracy asks Jimmy why he hadn't told her about the situation with his mother (or the woman who appears to be his mother) before. There are two good reasons why he didn't. First, until the night depicted early in the film, he hadn't been unfaithful during his relationship with Tracy. His prior acts, although some would call them taboo (esp if Kate truly was his mother), occurred earlier than that. Second, until he realizes that Ray was wounded and lost his penis, he has no way of knowing whether he is the father of the boys.
He may, however, sense on some level that his brothers are more than just his brothers. In a very early scene, Tracy observes that he seems remarkably concerned about the kids.
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