im thinking you may be able to feel it, just because you are thinking about it and you are not used to walking around having something foreign in there but there shouldn't be pain. that is unusual. a tampon is small enough that it shouldn't cause any pain being inserted. even sex after the first few tries shouldn't be painful. this is something, embarrassing as it is that you should talk to your dr about. something else you could try is to get some vaginal lube and put that with some easy glide tampons and see if that makes inserting them easier. take care