Cool stuff. You'd need to jailbreak your Glass to install the app though. Glassware only works as web services over the Mirror API for the time being, not as installable software.
How does Glass tell if you're winking or blinking?
I imagine duration and "measured muscle tension" around the eye would work. A deliberate strong wink should be distinguishable from a blink. It can work the same way a long click or long tap works (think about how you cause the icons on the iPhone launcher home screen to wiggle so you can rearrange or delete them)