One thing I'll say, please don't take on the task of de-virginizing a guy unless you can see it through. You may have to "play the lead" the first few times. What I mean is that you basically need to be generous, let it be about him, and just give the guy the time and space to find his way of making love. The best thing you can do is assure him that you're not going anywhere.

When I say be generous, i mean give him head, give him handjobs, don't skip the steps along the way. It's not just about intercourse, it's about him learning how to give you the space to give pleasure to him. It may feel like you're just servicing him the first few times. Allow it to unfold gracefully. Give him something special that he'll remember all his life.

On a practical level, he may not come the first time, if he's used to masturbating, you may need to "train" his c*ck to respond the stimulation of a woman's hand or a woman's mouth. This is normal. Take your time. Let him know it's OK.

Virginity is not merely the absence of sexual experience, it is the presence of a certain hestitancy, a sense of anticipation, all the primal stuff about a boy wanting to become a man. He may act strange, like he's too much inside his head. Understand that this is normal, look past your normal female reactions and see on a higher level, into his heart. He wants nothing more than to be a good man, a good lover for you, he just needs time to find that place inside himself.

Don't just try it once and then give up if things don't go well. And if you get cold feet, absolutely don't play games about it (that is, don't turn it into his problem). There is a special corner in for women who mess with a guy's head and heart that way.