Ankle hurts when i point toes foward, what could be wrong?

See below: Could just be due to the pull of the muscles or could be pressure on the nerve.

Tendinitis is common: When you point your toes forward, the tendons on top of your foot are being stretched maximally. If there is any strain or injury in these tendons, they will hurt when in this position. There is also the possibility of bone impingement in the front part of the ankle. This is generally an arthritic type condition if present. The more common presentations are soft tissue in nature.