Place cut strawberries into a bowl and sprinkle sugar over the strawberries. Cover bowl with plastic wrap. Let sugar marinate over the strawberries for a couple of hours before using. Prepare whipped cream by combining heavy whipping cream, 2 teaspoons of sugar, and 1/2 teaspoon vanilla in a bowl and beat with a hand mixer until the whipped cream is fluffy.
Assemble shortcakes by placing one or two Twinkies on a plate. Spoon strawberries over the Twinkies and top with whipped cream.