Sometimes when inserting their tampon or cup your preteen or teen may feel that they just can’t seem to get it in the correct place, or it just doesn’t feel right. It may take some practice to place it comfortably. If attempting to place a tampon is ever painful, there are a couple of simple techniques that they can try. Tell them to try to relax, and if the tampon or cup is dry, some KY Jelly or other water-based lubricant can also make insertion easier. The same goes for removal. If attempting to insert a tampon or cup is very painful or seems impossible, a gynecologist can help identify what may be causing this. This might be Vaginismus, an involuntary tightening or spasm that happens when something is being inserted into the vagina. Or sometimes, there can be changes in the hymen that can make insertion of a tampon difficult.