Is a freckle that hurts / feels like a bruise a sign of skin cancer?

Need to exclude : Cancer. Any pigmented skin lesion that has changed in size, or color needs to be investigated to exclude melanoma. Consult your doctor to see if the lesions needs to be excised and submitted to a pathologist for examination.

Hard to say: It's impossible to say yes or no based on that description alone. What you describe is unusual enough that you should have a thorough skin examination with a special focus on the area you mentioned.

Possible: While pain is not a usually symptom of skin cancer. Any changes in your freckles should be brought to the attention of your friendly dermatologist.