the tampon hurt you because you weren't actually on your period and were therefor much drier than you would be. You probably didn't insert it high enough into the vagina - if you were too push it in with your finger and not an applicator - it would be high enough to be able to insert your entire finger. I was difficult to pull out because of the cotton sticking too the inside of your vagina - because of not having enough moisture. This can happen if you use the wrong level of tampon as well at varying times of your cycle. Example - if your flow from your period was very light and you tried to use a super plus tampon - it would be quite uncomfortable, especially too remove it.