In a medium bowl, combine the chopped cuttlefish with bread crumbs and eggs. Chop 2 of the garlic cloves and add with the onion and 1/3 cup parsley to the bread crumb mixture. Stir in the milk and 3 tablespoons oil and mix together briefly. Add salt and pepper, to taste, cheese, olives, and tomatoes. Using your hands, mix well, and stuff each of the whole cuttlefish loosely with the mixture.
Finely chop the remaining clove of garlicand add to a small bowl along with the remaining 3 tablespoons parsley. In a pan large enough to hold the cuttlefish in 1layer, heat remaining 3 tablespoons olive oil over medium heat and add finely chopped garlic and parsley. When aromatics begin to sizzle, arrange stuffed cuttlefish in the frying pan, open side down. Brown for about 3 to 4 minutes, then carefully turn, and brown on the other side. When brown on both sides, add white wine to the pan, reduce the heat to a gentle simmer and cook, uncovered, for about 30 minutes, or until cuttlefish are tender. If the pan starts to look dry, add more wine.
Serve immediately with lemon wedges, if desired, and the small amount of sauce left in the pan spooned over the cuttlefish.