1Preheat an outdoor grill for medium heat, and lightly oil the grate.
Slice off the top of each tomato. Use a spoon to hollow out the inside. Rub the olive oil onto the outside of the tomatoes, coating well. Mix cream cheese, with bacon and cheddar cheese, and pepper, Fill each tomato with cheese filling,
Place tomatoes on preheated grill. Cook until tomatoes are soft and wrinkled, and cheese is hot, about 15 minutes.