How can I let this guy I like know that I's ok to feel me up while we are making out? And also, should I take my bra off and my shirt. I have large boobs, but I have big nipples and I'm self-conscious about guys seeing them. What should I do?
Firstly, don't worry about your nipples and boobs. He's going to like them. Secondly, most guys are pretty good at paying attention to what gets reactions from the girl they are with, so if he plays at the edge of your shirt, either with the shirt or your skin he is probably checking for your reaction! So anything he does that goes in the direction of what you want make sure to be obvious about liking it (he probably doesn't want to piss you off or move too fast because it will ruin his chances of ever getting your shirt off). Also, make sure he's in a position where he doesn't have to support some of his weight on his arms, because he won't be doing anything with his hands if that's the case. I suggest you try to get on top or beside and play with the parts of his body that you want him to play with on you (if you want his hands on your chest, put yours on his. Give his him some time to respond, but if he doesn't get it you can try touching, rubbing his arms (and sort of moving them where you want them). If he's really not figuring this out, you can always just take of your own shirt or take off his. If you remove his, chance is he won't be worried about taking off yours.
When things are heated you can start to give him some 'ok' signs of physical contact, so that he picks up from your body language and behavior that there may be a green light to go ahead and get a little more bold.
Some things you can do are starting to let your hands roam, you don't have to go anywhere explicit, just rub his body, caress his chest, things like that, get your hands involved.
If you really want to give the guy a hint you can always just guide his hand wherever you want him to go. The guy would have to be daft not to take the reigns from there.
I'll skip the how to give him a hint because everyone else has already said what I would.
I'm small breasted and was very self-concious about having my bra off so for a while I just kept it on and we both still had a lot of fun with that, I'm a lot more comfortable with him now and am much happier about having it off now. so if your not totally comfortable having 'it all hang out' keep your bra on for now, who knows... maybe he'll try his luck at taking it off, and by then hopefully you'll both be comfortable with it.