Blackish freckle appeared suddenly. I squeezed it a little thinking its blister and now there is a lot of bleeding under my skin. The freckle hurts?

Derm consult. This may be a simple traumatic blister from a trauma that you weren't aware of or seem severe at the time. It would have some blood and clot beneath the blister and be painful as well. Melanomas on the other hand appear dark but are irregular. If this new freckle doesn't disappear in the next few days I would simple have either a good primary or dermatologist examine the lesion.