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.
What I am supposed to do?