Best Answer - Chosen by Asker actually, it is not so post to hurt, i started mine around Christmas(December) put a new one in- here are some positions, 1) put your leg on the toilet and tilt the tampon to the back of your body, trust me, that helped me!! 2) put your butt positioned on the end of the toilet(where you DON'T fall off), and point the tampon to the back of your spine(not straight, but slightly down) the first time i had to put one in, was WEIRD and i was kinda forced because i was just about to go swimming..:/ #2 works best for me.. also, place your middle finger on the separating part of the tampon(where you see it) and pointer finger on the end... hope this helps(: ANY OTHER ADVICE... just Message me, ive learned a ton! ALSO, this can help you.......... (but not as much for Tampon inserting) www.Beinggirl.com it WILL take a couple of trys but, you will get it..Much better than pads, you shouldnt feel it and when you take it out there is a tad bit of pain for like 3 seconds(which is not bad) Other Answers (3) It must be extremely uncomfortable to have it in like that. I know it's difficult the first times you try it. Like someone else said, you need to push it at a slight angle. And for a better position, put one leg up on the edge of the bathtub or something, it'll make