Combine the graham crackers and superfine sugar in a dish. Dip the rim of the drinking glasses into the lime juice to moisten, then dip into the graham cracker mixture. Carefully freeze for 5 minutes while preparing the cocktail .
Combine vodka, lime juice, simple syrup, vanilla extract, and ice in a cocktail shaker and "dry" shake for 1 minutes. the mixture will be frothy. Add in the ice and shake again until the shaker is frosted over.
Strain the martini mixture into the prepared martini glasses garnished with the frozen graham cracker rim. Garnish with a dollop of freshly whipped cream, lime wheel and a dusting of additional graham cracker crumbs.