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Prepare a grill for medium-high heat cooking. Thread cherry tomatoes onto 2 metal skewers and grill, turning frequently, until the skins begin to char and tomatoes are tender but not bursting, 4 to 5 minutes. Place in a blender with tahini, vinegar, salt and cayenne, and blend until smooth; add water a tablespoon at a time until dressing is a little thicker than heavy cream.