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Oct 23, 2017 · The answer to both of these questions is yes. You can insert a finger into penis and play with your urethra. In fact, there are many men who enjoy this type of stimulation to the fullest. Playing with your pee hole and inserting things into the penis are known as urethral stimulation or urethral play. This is a highly arousing sexual activity. Sep 04, 2010 · I want to finger my penis but it hurts? that it is harmful it may cause an infection on your penis ejaculation tube,also you can deep in your finger,well human finger is too big for penis hole,it is impossible in this case,do not waste your time buddy trying to hurt your self and doing the impossible,you can go with Thumbs down. Report Followers: 2.