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Melt the chocolate in the microwave for 30 second increments, stirring after each. Let the chocolate cool for a bit after it's completely melted.
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In a large bowl, beat the butter and cream cheese together until smooth for about 1 minute.
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Add in the melted chocolate and vanilla and beat for another minute.
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Beat in the sugar by adding small amounts at a time until the mixture is light and fluffy.
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Add milk, one tablespoon at a time, until the desired consistency is reached.
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Transfer the frosting to a large Ziploc bag. I use a large cup to stabilize the bag while adding frosting. Cup the tip off the corner of the bag and ta-da! You have yourself a piping bag.
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Pipe the frosting onto the cupcakes.