Place the black raspberries in a bowl and microwave until warm and some juice is released. Mash the berries with a fork as much as you can.
To make the fudge, heat the heavy cream in a saucepan over low heat until the edges just bubble and the cream is warm. Place the chopped chocolate in a bowl. Pour the warm cream over top and let sit for 30 seconds, then stir until the chocolate melts. This will take a few minutes! Once the chocolate is melted, stir in the black raspberries and any juice. Stir stir stir to make it come all together.
Rim the insides of the glasses with the chocolate. Spread a bit on the outside of the glasses too. Sprinkle graham crumbs on the chocolate.
Place the pie, ice cream and milk in the blender. Blend until pureed then pour in the glasses. Serve!