Try and see stretches as an over exagerration of a muscle movement, therefore after reading your post all I did was immitate what I thought you wanted to achieve.... My findings...... (I even did it sat down)...
raise you foot off the floor, then point your toes towards the ground, now try and force your toes towards the ground whilst trying to force the top of your foot forward.... or bend your toes (towards the bottom of your foot) and put your foot on the floor (yes on your bent toes, as though making a fist like motion with your foot) now force your heel forward.
Its important with any stretch that if you feel pain you should stop, but pain shouldn't be confused with slight dis-comfort!
No, I'm not putting things on too tight and the tightness continues a little after running. Ironically a woman at work gave the same suggestion that you have. I think I'll give everything a go and let you know how things get on.
When I first started driving my ankle would feel stiff in the same place as you describe, Delinquent. That was a few years back and it never happens now, i'd forgot about it until I read your post.
Are you just starting to train more frequently after a period of relative innactivity? If so maybe the muscles there just need to build a little more? This is what I attributed the dissapearence of my own stiffness.