Once you are comfortable with your decision, you won't need me to tell you the answer to your original question, which is that, yes, you should tell him you are a virgin, but only if the topic comes up naturally. Telling a guy that you are a virgin should be no different than telling him who you voted for in the presidential elections, or whether or not you believe in god, or any other potentially divisive fact about yourself.You wouldn't feel a need to "confess" to him that you voted for Ron Paul on your first date; but you'd tell him if he asked - or if your political views came up in the course of conversation. - these are the kinds of things that you eventually need to know about each other because they reveal a person's values; but we don't immediately discuss them because a person's values aren't the only important thing about them.
So the first thing you need to do in order to start dating successfully as a virgin is to decide when or under what circumstances you want to stop dating as a virgin. This seems like a simple "yes" or "no" question, but it isn't.
I will say that Western society has undeniably pushed the normal marriage age beyond the years at which are bodies are prime for sex and children (few people will dispute this).
And while this doesn't mean that you should or shouldn't have sex, it does mean that if you want to stay a virgin until marriage, it's going to be tough.
The fear was so severe that I used to rehearse in my mind how I would equivocate if I were ever asked about it.
I was much less ashamed about being a virgin, because virginity was something I actively believed in at the time.
The very fact that you feel the need to ask it betrays a problem much deeper than your confusion about whether or not to tell a guy that you've never had sex before.