Long foreskin and condoms

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Hi everyone!

So, I'm a 19yo guy but I learned only 1 year and half ago that a penis is supposed to be able to pull back the foreskin. I have NEVER had any idea about it (nor my doctor nor my parents said anything about it) and my penis, during regular masturbation was never pulled back even a bit.

Anyway, not much time before learning about it, I started a distance relationship with a girl. Since We hadn't much chance to explore this matter, for the whole first year of our relationship we limited ourselves (both virgins) to oral and manual sex.
But 6 months ago I decided that I had to something that isn't circumicision. I started to strerch it and I am able to pull it back a bit, but still not enough to expose my glans (when erect, while flaccid I may be able to do it, but for now it hurts too much)
The point is that my foreskin is longer than the penis itself, and the top of it is a bit smaller than the rest of it. When I am fully erect and I try to expose the glans, at a certain point this smaller ring doesn't let me do that.

I don't know why, but when I try to put on a condom (I bought a full fucking pack of it) I just can't. It slide on the foreskin or part of it enters in the gap created by the smaller foreskin and it hurts A LOT.

For STDs we are safe, so I could even ask her to use female condoms or the pill for our first times (we are planning it) but I would prefer to avoid it for various reasons.

SO
What I am supposed to do?

@Hyperversum It seems as if you still have some stretching to do. Just to be clear, we're talking about stretching the width, not the length. You should be able to retract the foreskin completely without pain. The fact that this is not possible for you indicates that more stretching is needed. You might try doing it in a warm bath as the skin will be more flexible then.

Also you indicated that you might ask her to take a BC pill for your first times. Be aware that she will have to be taking the pill consistently for 7 days prior to unprotected sex for protection to exist.

Sure, we will do it without any doubt, if she will use it. But I doubt it. I would prefer to use a condom and end of the story.
The point is that, as I said above, it really HURTS me, when it "mix" (not the right word but I hope that you get what i mean) with the retracted foreskin. Even if I will be able to retract I will still have this problem.

The glans will get less sensitive with time, if that is the problem.

I wonder if your condom is on too loosely? I've wondering how it "enters the gap".

@Ineligible I am sorry if I can't explain myself decently, but I'm not a native English speaker and while I can speak decently in general I have some problem with this topic ahahahah!

Anyway, I will try. I feel like if the condom can't be properly streched on the shaft, because of the "mass" of foreskin that i can't pull under the glans.

Your English is very good, and I notice I made an error in mine. :)