I’ve been using tampons for 2 yrs and embarrassingly have to admit that I still can’t insert it properly without it feeling painful. I can’t say I’m experienced because my cycle has been very irregular for the past 2 yrs and is only just starting to become regular. Because I have always done an excessive amount of sport. I was a swimmer and had a few times that I could feel the tampon whilst swimming and would have to get out half way through the session and try inserting again. I was so desperate to get it right.