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Slice about 1/4 inch off the top of each tomato. If necessary, trim a sliver off the bottom so the tomato sits flat. Gently scoop out the seeds with a small spoon or the tip of a small knife.
Mash goat cheese, olives, milk and 1/8 teaspoon pepper in a small bowl until well combined. Fill each hollowed tomato with a generous 1 teaspoon of the cheese mixture. Sprinkle with oregano and more pepper, if desired.