So I've been trying to figure out wtf is going on with Kev's straw of a vagina and I think figured it out. The reason why you're supposed to dilate is because you're trying make sure the wound heals in a way in which scar tissue doesn't build up and cause the hole to be smaller. This is what people mean when they say "you have to dilate or your neovagina will close up". The body will naturally want to cover the entire inside in scar tissue.
So the issue is two things: the surgery seemed to have been botched and Kevin is too lazy to maintain a daily regimen and dilate like he should. Botched surgeries cause scar tissue to form and lack of dilation allows the tissue to form.
The amount of coping when it comes to Kev talking about his axe wound is also a bit amusing. He'll say that it's not closing up and that his depth is still there.
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However, he seems to be misunderstanding that his "vagina" isn't closing up by losing depth. It's closing up by losing circumference. Either way, he fucked up and now he has to go back to get more surgery if he ever wants to be penetrated.