Hello Capris: I'm sorry you are caught up in these difficult circumstances. I don't know as there is much I can offer with regard to this. (It's been a while since you posted it. Perhaps circumstances have changed?)

But I noticed no one replied to you post. (I do apologize for that.)

So I thought I would at least let you know I read your post. And I wish you well.
From my perspective, I think this is really a situation best handled by working through it with a skilled counselor or therapist. You need to sort through how much of this is related to your previous relationships versus your OCD. And that's not something you're going to be able to resolve quickly. It's something that must be worked through, delved into, gradually... over a period of time.
No matter what your bf says, there's going to be no way to know for certain if he's telling the truth (unless you actually catch him cheating of course.)

And I do think you're correct. There does come a point where asking these sorts of questions over-&-over simply becomes too much.

Anyway... I hope things are going well. My best wishes to you...