Is it normal to be scared to have sex?

Yeah I can definietely relate.
There are therapists which can help you with this fear, open communication with your partner is good too if you have a trustworthy patient partner who cares about you and is willing to move slow. If he is not willing to be supportive and understanding of this he's not a good potential partner.
Also yes it does often hurt the first time but if you're relaxed and wet enough it will hurt much less and if you're lucky not at all. I think that for many it hurts because they are too tense due to making a big deal out of losing their virginity, as well as not having long enough foreplay.
It's likely it'll feel a bit uncomfortable the first time though if you've never been penetrated at all before.

I read this question a couple of times before I spotted the phrase "if I meet him" in reference to this great guy you've somehow found.

So, in other words, everything in your question is purely hypothetical. You've never had any sort of relationship with a guy, you've never even kissed a guy, and you having sex with this fantastic guy is something that has only ever happened in your head. And, given how you quite possibly know nothing about the guy beyond whatever image he presents to strangers or people he's vaguely friendly with, it's entirely possible he would not be interested in having sex with you.

To deal with your pregnancy phobia first and to be very blunt, any woman who puts all the responsibility for birth control on the guy and relies solely on a condom is totally fucking stupid. It's entirely rational for you to be extremely concerned about the possibility of becoming pregnant. No matter how decent and caring a man is and even if you stay together long-term, the pregnancy would be something that happened to your body. The whole process could be nine months of various types of crap, and there could be life-long effects on your health. And, no matter how responsible and emotionally mature a man is, the reality is that you would be the child's mother, and that's something which would affect you in countless ways - both positive and negative - for the rest of your life.

Modern methods of female birth control are highly effective. If you're really paranoid about getting pregnant and you ever were in a real-world relationship with a guy where sex was on the cards, than you would have two options: refuse to have any sort of sex which involved semen getting anywhere near your vagina, or accept that you bear half of the responsibility for preventing a pregnancy and find a method of birth control that suited you.

Something else that you might consider is that, contrary to what many people believe, the definition of sex is not limited to a penis being in a vagina. There are lots of other things you and a guy could do which are definitely sexual since they involve the genitals, but fall short of vaginal penetration by a penis.

Your question suggests to me that you've built penetrative sex up into this enormous, scary, life-altering and probably traumatic event which has been ominously lurking somewhere just over the horizon forever. I suspect that could well be the reason behind your "ridiculously specific and obscure standards"; you may have convinced yourself that they're a matter of personal choice and you having high personal standards, but actually you use them to avoid the possibility of sex. Those with a healthy attitude towards sex would probably call that self-sabotaging.

I obviously have no idea why you think of sex in this way. Maybe someone shoved a lot of really nasty, ignorant, sex-negative crap into your head when you were a kid and you haven't yet managed to overcome that indoctrination. Maybe something else has prompted you to talk yourself into being shit-scared of it. Whatever the reason, it's irrational. Maybe some good counselling would help you figure out why you have these feelings and deal with them.

It also sounds a lot to me like you're one of those women who clings to the delusional belief that there's a Mr Perfect waiting for you out there somewhere. Spoiler alert: he doesn't exist. If you ever get to the point where you're capable of engaging with real-life men in an intimate way, you'll find that they're all as messed up as you are, although probably not in exactly the same way. One sign that you might have found Mr Good-Enough is if, at some point when it seems appropriate to you, you mention that you have issues with sex and he doesn't grab his coat and leave. Such guys do exist, and a really good man who's seriously into you would have enough patience to gently explore what your limits and apprehensions are, and suggest ways the two of you could work around them.

Finally, concerning your final question, a woman does not necessarily feel pain the first time a penis penetrates her vagina. If she's not sexually aroused and well-lubricated (either naturally or by a commercial product) and the guy is rough and impatient and/or he has an unusually large penis, it is possible for there to be some degree of discomfort or even pain. However, a guy who knows what he's doing when it comes to sex and cares about his partner's pleasure will ensure that she's had at least one orgasm before he gets around to penetrating her, and he'll be guided by her reactions when he's going in. In that situation, it's entirely possible that the woman will feel the precise opposite of pain. Also, if you've ever put anything of any size in your vagina during masturbation, then it's highly unlikely you'd feel anything unpleasant.

Your's is not that unusual of a situation.

Most important you need to discuss this with your potential sexual partner. You can do that before or after you research birth control and STDs

If he cares about you he will be patient with you and go slow... allowing you to progress at your own rate.

The internet is full of information on how your monthly cycle works, when you are most likely to get pregnant (and when its almost impossible),along with the information on the various methods of birth control.

I suggest you figure out how you are going to address birth control; and you may wish to do that before you start having sex.

Of course, no birth control method is 100% - so there is always a risk. But, the vast majority of society understands that and you would find a lot of acceptance.

You might wish to read up on STD's as well - and look at private STD testing (10 panel tests can be gotten in most major cities for a fraction of what your insurance copay or deductible would be in most cases - and insurance normally only covers 4 STDs unless there is a real reason to test for the others.

I've found it's just faster and cheaper to fork out the several hundred for a full 10 panel STD test (and my planned partner does the same testing as well).

Here is the one I typically use. Please note the bottom of the page. Some of the test will not be accurate until up to 8 weeks after someone has had sex with an infected person, others are accurate in a few days or a week or so.

My personal rule is that any potential partner needs to have abstained from sex for up to 9 weeks in advance of the testing. I've had 2 cases in my youth (fortunately treatable) - and I'm done with that unless its the 1 in a thousand (or more) case of the test missing it (no test is 100% accurate - but most of the STD tests are highly accurate after the incubation period).

https://www.healthlabs.com/comprehensive-10-test-std-testing