Combine creamer and strawberries in a blender, use pusher or scrape down sides until mixture is of shake consistency. Add additional creamer or milk if you need to thin it out more. Add additional strawberries if you need to thicken it.
Pour about 3 ounces of shake into the bottom of a 16 ounce glass. Add a dollop of whipped cream. Add about 3 ounces more of shake, and then add another dollop of whipped cream. Give shake a light stir to swirl whipped cream and shake. Add 2 ounces of shake and top off with a dollop of whipped cream and a fresh strawberry. Repeat until all glasses are filled.