In a bowl, toss the strawberries with sugar and let stand, stirring occasionally, until the strawberries release their juices, about 10 minutes.
In a blender, combine half each of strawberries and their juices, vodka, and lime juice with 1 cup of ice.
Fill 10 collins glasses halfway up with ice. Pour the cocktail into the glasses, top each with ½ tablespoon of Riesling and serve.