Sandwiches: Heat olive oil and cracked pepper over low heat. Turn off and let infuse for 10 minutes. Place sliced cheese on half of the bread slices (making sure the cheese comes to the edge of the crust). Place top slice on each sandwich and put them together so they are crust to crust. Cover all the sandwiches with a layer of plastic wrap and place a medium cutting board on top of sandwiches to gently weigh them down for 15 minutes. Using a pastry brush, thoroughly brush surface of both faces of the sandwich with the pepper oil. Preheat a Panini griddle on low or a medium sauté pan over low heat. Wipe surface with a little oil. Place sandwiches in griddle or pan and cook until slightly browned, 2 - 3 minutes per side until cheese is melted. Keep heat low so bread doesn't burn.
Tomato soup: Combine olive oil, onion and garlic in medium saucepan and sweat together for about 20 minutes, or until the onions are soft and translucent. Add tomatoes and cook another 15 minutes.
Add stock and basil leaves and bring to a simmer. Cook gently for 20 minutes.
Place soup into a large bowl through a fine strainer or food mill, to remove seeds, skins and basil. Salt and pepper (cayenne) to taste. Serve tomato soup hot with warm sandwiches. Drizzle extra virgin oil over the soup along with a couple small basil tops.