Yeah, nobody ever talks about the awkward part of sex, do they? You'd think that'd come up more often.
The best way to approach him about it is to be honest. Tell him you're not a virgin, but you're not very experienced and you're not sure what you want in the bedroom, so he'll need to go slow and be ready to stop if you're uncomfortable. It's unlikely he's extremely experienced himself, and it might even come as a relief. Start slow and keep an open mind, you'll get confidence as you practice. Fortunately, the practice is a lot of fun.
As far as the latex allergy goes, don't goof around; go to the doctor pronto and get that confirmed. But if that's going to take too long, go out and get some polyurethane condoms. Not sheepskin! That crap is like using a net to catch individual sperm. Polyurethane actually is FDA certified and will let you experiment with less risk.
Good luck and have fun!
oh sweetie, everybody is nervous about the first time with somebody whether you are 23 or 33, TRUST ME. especially if it's somebody who you've been spending time with over a couple of months. so my guess is that he is a little nervous himself, and if he has waited this long for you, he cares about you enough to want you to be nothing but comfortable and....as not nervous as possible. Dan is right, my hunch would be that he would be a bit relieved, it will take a LOT of pressure off of him, and chances are bring the two of you even closer. and copy that on the other thing too, chances are he will bring that topic up as well. include him in the process of finding the appropriate alternative and it will also bond you both a bit to ease those first time jitters. but we all have those awkward moments and it doesn't have anything to do with level of experience. and note that they are moments. they don't last. the anticipation makes them seem so much bigger and longer, but they aren't. have fun!
Lots of women have problems with latex condoms. Its pretty common, especially if you already have sensitive skin on the rest of your body. The polyeurothane can be a little harder to find and a bit more expensive, but they feel much much better than latex. Even guys notice the difference so they usually don't mind having to work harder to find them.