Shouldn't have is something of a moving target: it depends, I suppose on what standards we apply. I have fucked women who were off limits, and I suppose you could say I shouldn't have, but I've done it so much that I don't know that I see it that way.
On the other hand, there were a couple of occasions, now years ago, when it was flat out dangerous, and not with the risk. In both cases, I'm talking about barebacking wh*r*s. Why I did it is, I suppose, obvious: I let sex control my brain. In neither case was it spectacular sex and in both cases I worked about it enough that it was not worth it. Shouldn't have done it.
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