Dude really, you got 2 numbers already? Killing it... it's GREAT to see you putting your balls on the line and talking to some hotties, and frankly if you just keep doing that and pushing your interactions then questions like this will become redundant, I mean once you start to go on several dates a week then who cares how my times you fuck up the sex (if any times) because you'll have plenty of pussy to practice on, can't fail to improve if u learn from mistakes.
But zooming in from the bigger picture and addressing your question... well firstly you are in pretty good shape already, you've had a makeout so you couldn't be going that far wrong, what could be more natural than simply making out with her till you are both ready, and then just slipping it in? You already know how to do this, it's in your DNA.
I appreciate your catch-22 but there's really no way around it except to jump in and try to do it. What you can do is arm yourself with an escalation plan, not in too much detail but the broad steps at least, and here Drexel Scott's book "Straight to Sex" is useful, it's less than $10 and will take you through warming her up with gentle kissing, dealing with her objections and having the sex itself. As a bonus it also discusses what to do when you've just pulled her home.
My procedure is a bit simpler than Drexel's, this might not work in every case since it will depend what she likes etc (so may have to be more creative if she doesn't respond as expected, and/or do more of the things she likes and less of others)... but as a broad outline:
1. Kiss her. A good way is to put your hand on her cheek or chin etc and turn her head towards you as you go in to kiss on the lips, if she resists turning her head then you have early warning of problems so won't end up kissing thin air.
2. How to kiss: With closed mouth and soft lips (muscles relaxed) just nibble on her lips a bit, try to take a little bit of her lip between yours and just play with it a little then let go and go for the other one, if she likes this her mouth will naturally open up a little as you proceed and you can try a little tongue, don't go overboard, just lick her lips slightly as you nibble and this will prompt her to meet your tongue with hers, if she doesn't then try just gently exploring between her lips, taking your time about it and not going further than you have to, and see if you can hook up with her tongue. By this stage I think you'll know what to do, just kiss her passionately with tongue for a bit and she should do the same.
3. Erogenous zones... at this stage I would generally start making love to her ear, you kiss it by nibbling and eventually adding some tongue, as you did before. Putting your tongue right down her earhole is something to build up to but she'll love it when properly warmed up. Remember to breathe some hot breath into her ear while nibbling, licking etc, especially if it's wet from your saliva this will have a hot/cold effect.
4. You should also be feeling her body whilst doing this, hands on her back, sides, stomach etc, usually inside her clothes depending on what she's wearing. If you're properly making love to her ear she'll begin to pant and moan and then it's pretty much a done deal (note her neck is also good although not as sensitive as the ear, also don't lick or slobber on her body except the orifices and the nipples, just kiss).
5. When she's expressing her pleasure, keep kissing her or doing the ear or neck or moving between these, plus go for that pussy and start stimulating it, through the pants at first, then moving inside to the panties and eventually to the pussy itself. It's handy to have some lube to put on your fingers here.
6. Locate the clit and gently stimulate, she should arch her body and writhe around and rhythmically push against your hand, when she's nicely warmed up from this it's time to throw on a condom and fuck her, you can refer to articles on this. A true pro would also continue to stimulate that pussy and other erogenous zones while dealing with the clothes, the condom etc, until inside her, cos it can happen they change their mind and run away, this has happened to me.
Hope that's useful.
Ray