I always used to be a very flexible person. In middle school, I could do full splits straddle and front-and-back on both sides. Even into high school and college, I continued to be able to do lotus positions, kicks above my head, deep lunges, stuff like that. I kind of fell off the wagon with it, but I'm trying to get back into it. Right now, I'm having a major problem with cramping in the soles of my feet during certain stretches.
The two stretches where it has become most evident are the Pigeon Stretch (pain in the front foot for both sides) and the kneeling shin stretch (it seems to go by a variety of names) on both feet. I get some degree of the same problem as the kneeling shin stretch just sitting in Seiza. The muscles in the sole of my feet ''feel'' cramped and hard. Massaging them will help relieve the pain and tension for a bit, but it often comes back when I stretch again. I've tried doing basic ankle stretches beforehand, but to little avail. I occasionally get something like this when doing deep lunges, but never nearly as badly.
I guess I'm a bit worried that, if I keep pushing through, I'm going to impair my stretching progress because my body will associate stretching with pain, but I don't want to drop these exercises because the pain seems unrelated to what I'm actually stretching.