It's even worse when you realise what dilation is actually doing. Think of it this way. All the cells on the surface of his penis which were used to being in an outside dry-ish environment (let's not get into Kevin's underpant hygiene routine) suddenly find themselves all squished together in a damp space (I'm talking damp in the sense that the sweat has nowhere to evaporate to rather than anything else). So there first instinct is what we call healing. What this means is that those cells will start to form little bonds with their new neighbours. It doesn't happen instantly everywhere, but slowly over the course of a couple of weeks to months.
Now the aim of dilating is to jump in before too many of those little bonds have formed, and to stretch them until they break. In other words, it has to hurt, and if it's not hurting then it's not working. You take a specially shaped surgical stick, lube it up, stick it inside the inverted penis and hold it there until it stops hurting. The lube is needed because you're trying to stretch that poor tortured bit of skin, so you need a stick that is slightly too big. Then when the pain dies down that means that that particular stick has stretched and popped as many of those little bonds as it is capable of. Then you take a slightly thicker stick, lube it up and repeat. You only stop when the stick you are using makes you think that you are in danger of splitting the remnants of the penis rather that just bursting those microscopic bonds.
And the moment you've finished, your body starts healing again, rebuilding all those bonds from scratch, like a spider rebuilding its web. So you have to repeat the whole process three times a day. Forever. I can't think of anything that sounds so horrible to do. And to go through all that effort knowing in the back of your mind that no-one really wants to fuck it anyway.