I've been in a relationship for the past few months. There is a slight issue however. I'm 22 and have been sexually active for eight years. I've had numerous sexual partners, and had several relationships where sex was a daily occurence. The girl I have been seeing is amazing, everything I've always wanted (intelligent, educated, funny, caring, beautiful, you name it!). The problem is a compound of a few different things. First, I'm the first person she has ever been in a relationship with (very sheltered life). This has made things slightly awkward for me, although manageable. The big problem is that she is a virgin. Her being a virgin doesn't bother me, how I should approach the issue is. I've never been with a virgin. I'm worried that at this point in our relationship we will soon be approaching the point of sexual activity. This doesn't bother her, however it bothers me. I'm worried that her first time will possibly be painful, or just unenjoyable. I'm afraid this will turn her away from the relationship. She has insinuated that she is ready for sex, although I don't want to ruin things. I'm worried to even speak to her about this because I don't want to come across like "Hey I'm worried about things and it's your fault for being a virgin", there just doesn't seem like a good way to approach her about this. She knows I have been sexually active. I have given her an idea of how many partners I've had, how often I've been intimate but left out the details; sexual fetishes I've engaged in and enjoy that I'm worried might bother her, the fact that I've engaged in threesomes, etc... Should I talk to her, if so how? Should I really be worried about this effecting our relationship? Also for the female members, what could have made your first time better, any advice? Anyone?