Re: A few question
No, your questions are not silly. In fact, I think a lot of women have them when they first start having sex.
You can put a towel down on the surface you are having sex on to avoid the "mess", or you could change your position such that it doesn't drip out. If he ejaculates inside of you while you are on top, the semen will come out as he pulls out. But if he is on top of you, while you have a pillow under your but to raise it up, when he pulls out, it won't make such a "mess". This is my favorite position because it allows for deep penetration and we can lock lips. In any event, what goes in will come out unless you use a condom. He could also pull out and ejaculate on your stomach or another part of your body.
I don't look at my husband's semen as a mess. It is something to enjoy. I don't like him ejaculating in my mouth. He either ejaculates inside of me (which I prefer)or on my stomach. I actually like the taste of it. We use a towel or pad so as to not make a "mess" on the bed, couch or whatever surface we have sex on.
I also can get sore around the edges of the entrance to my vagina the next day. A little extra foreplay can help minimize this. Sometimes we use lube, but mosty I get wet enough, but I need him to insert his fingers inside (or a dildo that is smaller than his penis) me to open me up enough before he attempts penetration.
The fact that he has to play around with the head of is penis at the entrance to your vagina before penetration is not unusual. My husband does this as well. In addition to taking his time with penetration, have him rub it up and down your vulva, concentrating on the clitoris. I find this arouses me more and helps to open me up to allow me to take him inside me without pain.
As to our question as to whether you are having an orgasm or not, I don't know. When I had my first orgasm I knew I was having one. Do some reading from previous posts as to the different types of orgasms (clitoral, g spot, and blended).
and ways of achieving them (oral sex, vibrators, certain positions during intercourse).
Just have fun and enjoy sex. You waited until you got married. So it is gonna take some time to grow sexually. Make sure you involve your husband,talk to him and tell him what feels good...and if you don't already do so, masturbate on your own.