Stretching help

I find that stretching the way you’re supposed to (i.e. under the glans with the foreskin pulled back) is very uncomfortable. Is there any way of making this more comfortable? Or is it simply something one has to get used to?

Some, mostly uncut, use pulling with the foreskin on; other find flaccid dry jelqs a good alternative.

Pull with the foreskin extended. If you find your glans keeps on slipping under the foreskin, kegel some blood into your penor before pulling. THe kegeling should put some blood into the glans and provide something for you to push against.

You could try baby powder or wrap the head of your penis with something comfy like cloth or the like and see how you go :)