If you decide to tell him, just keep it simple. If you're honest, he'll be able to be more understanding of your insecurity and your excitement. The cliché is true: Communication is important when it comes to sex, especially if you care about someone, and it seems you do. That said, I'm all for honesty, particularly when you're thinking about doing something as significant as having sex for the first time. It's your body, and it's always your right to share information about your sex life - or keep it to yourself - anytime you'd like. Whether you tell him or not is ultimately your call and nobody else's. I feel I'm ready to sleep with him, but should I tell him first? If so, how do I bring it up? We're getting on really well, and our relationship is progressing fast. Should you tell a guy you're a virgin before you sleep with him? I'm 23, and the guy I'm seeing now is 27.