
I wish I had some advice for you, but I only have a sympathetic hug.
Would I come off seeming abnoxious, if I were to say for you to try and relax? I can only imagine that your less than ideal experiences are causing a bit of tension for both of you. I know that you know this, but be sure to use a healing lube, even in between your times together. Are the two of you giving yourselves enough time? You don't have to answer that, but I just wanted to toss it out there and encourage you to do so, if you aren't already.
I am hoping that this phase passes VERY quickly.