I remember being terrified of losing my first tooth! My mom tried everything, even tying a string around it and the other end of the string to the door knob. I started screaming bloody murder when she went to slam the door shut (and I could push my tooth front and back too...there was nothing holding it in!). Finally, she gave up and gave me one of those little carmel chews that I only got as treats. Well, it came out in seconds, but the carmel was kind of crunchy. I think I put the whole wad under my pillow for the tooth fairy since the tooth was kind of buried (it went in a baggie of course!
After that, I could do it myself.