I’m not sure if I can describe this problem succinctly so bare with me. Gay male 33.

I can fully retract my foreskin at all stages no problem. However, when I’m fully hard and manually retract my foreskin (it does not retract automatically), it essentially does not glide and stays pulled back unless I make a concerted effort to pull it up again. Easier to see with pics, but I’m hoping uncut guys will get it.

When I’m penetrating during anal sex, this means I cannot be retracted and enter, else it is painful and feels like my frenulum is about to rip. The only way I can do it is if I pull my foreskin far up before I enter (like literally manually bunching it over the head of my penis), and then entering.

But once I’m inside, I have to be careful with my thrusts, because if I push too far, my foreskin will retract all the way inside, and then the pain will start and I have to manually pull it forward again. This means I have to gauge the depth of each push to monitor how far my foreskin is pulled back to prevent pain.

My guess is that my foreskin is just somewhat tight when I’m fully hard, and that’s causing this. Has anyone had similar issues and what have you done to address it? Is it possible to achieve a smooth glide when erect?

Thanks for any tips.