This is not your mama's canned tomato soup. This Creamy Heirloom Tomato Soup is on a completely different level and you will never ever go back. Use the best quality vine-ripened tomatoes you can find, heirlooms if they are available. And please please please don't cheat and use milk, the taste explosion just won't be the same.
Set the broiler to high. Pop the tomatoes on a baking try, cut side up, making sure they aren't touching each other. Pop under the broiler for about 10 minutes each side but WATCH THEM (using tongs to flip them after the first ten minutes). You want them to be charred but not completely burnt. A little bit of black is ok.
Transfer the grilled tomatoes to a large saucepan. Add in the salt and pepper and a splash of hot sauce (I only add a little bit, as I am serving to kids, but do what works for your tastes).
Cook over a medium heat for about 20 minutes, stirring frequently, until the tomatoes have reduced to a sauce-like consistency. Don't let them burn.
Using either an immersion blender or transferring to a blender, blend the mixture until smooth. Return to the saucepan and adjust salt, pepper and/or hot sauce as needed.
Add the cream and simmer until the whole thing is heated through, about 5 mins. Serve straight away.