Hi everybody!
I posted over in Introductions but this might be a better place to do progress updates.
I've always had a pretty tight foreskin. I remember when it first started to separate from the glans, and it was pretty painful gently stretching it to get it further and further separated. I was pretty surprised when I got it all the way, I'd only been able to go about 20% of the way before that!
It would tend to stay right over the glans all the time pretty well (even when erect) - the opening was always pretty tight so pulling it back there'd be a bit of resistance and then eventually it would pop all the way back.
A few years later I got a bit fascinated with circumcision, and I saw the 'how to feel circumcised' taping method image. I was pretty curious but my foreskin and glans were so sensitive I couldn't imagine doing it full time.
Later on (when I was 19-20ish), my foreskin had eventually stretched out a bit and would (annoyingly at the time) sometimes pop back on its own (coming down from an erection probably), which would be agonizing. But I came across some stuff about pulling back and was curious to start trying. I don't think I ever got more than two days back then.
More recently, I've done it a few times, up to about a week. Now I'm trying again to give it a decent go!
The pictures attached were from the start of this attempt.