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The body allows you to be flexible to the extent you can handle those positions. Trying to power through a strong pain signal is your body saying you couldn't handle the responsibilities of that position. e.g. being able to get into the position but not out.
Increasing flexibility often benefits more from strengthening up rejected areas rather than trying to making strong something that is already strong enough.
Painful stretching is a sign you're doing it wrong, that you've missed something fundamental. Only when you shore up that necessary knowledge will the path open to you effortlessly and painlessly.
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