What you're proposing to do really isn't that unusual. I know another couple who were virgins when they got married. A few years in felt like she needed some more experience and was able to get it. She got her experience and he knows that she's not sitting around wondering what it would have been like, so it worked out.
Be prepared, though, if the guy you have a crush on just wants to carve another notch in his pistol. You said he was "kind of a ladies man".