Here’s how Shelley handles draining the grain bag after it comes out of the oven. The top of the mesh bag cools very quickly and is easy to handle. With a bit of careful manipulation you can turn the bag to apply pressure to squeeze out more wort with your fingers.
Use your own judgement! You know what you can handle regarding hot things in the kitchen. If it’s too hot for you, use a spoon or fork (careful not to poke the bag open) instead of your hands.