Well, I do not like the term but that is my problem. If three fingers are rooting around, there is likely no hymen left. So I guess the answer is yes. In the modern world with tampons and women's sport, bleeding is not necessarily expected.

Brandye is the doctor but I feel she left some things out. The "cherry" or more correctly the Hymen is a thin layer of skin inside the womans body. If you finger yourself, let him do it or use a dildo those can break the Hymen, at these points you might bleed or you might not, it depends on the largeness of the hole. Now comes in the other parts of what Brandye said, tampons can be like a dildo in the same respect but since you are planning on bleeding already you might not notice it. Also any rough contact, sports, car accident, etc could also cause the initial tear. And as brandye said since he has had 3 fingers inside of you this has probably taken what ever tear started and strechted it and worn the left over skin away. With all that you said I seriously doubt you have a full Hymen left or one of you would have felt it by now.