Do you feel pain or stretching?

[Edgaron]

For some reason when I do the ankle wall stretch, I don't feel much of a stretch. I pretty much only feel the tensed up shins and the top of the feet. If I put the front of the foot on something and then try to stretch, I feel  discomfort in my ankle. Is this how it should feel?

 

And for wrists, what limits your front lean (or planche lean)? Is it pain in wrist or the feeling that it can't stretch any more, or maybe even both?

 

Besides, should you ''arch'' your feet when doing stretches if you have flat feet? I noticed that if I do this in the front bend stretch I don't get the uncomfortable ''pain'' in my calf.