Does it always hurt? There is this girl that I am talking to that is a virgin, and I have never had sex with a virgin. We are really close and she has even told me that she thinks I am the right one for her firs time. What I am asking is, Is there anything that can be done to make it gentler on her? I have heard things like if she wears tampons it makes it less painful. Is there anything else? Remeber now, the most this girl has ever done is gotten felt up, nothing below the waist.