I always skinned back to piss for as long as I can remember. I'm not sure why I started doing that as I certainly wasn't taught to do it by my parents; I probably saw other boys do it at school. When I reached 12 or 13 I started leaving it back after pissing because I liked the feel and thought it looked "grown up" after I'd seen some cocks with exposed heads in a porn magazine.
It was probably a little uncomfortable at first but after a while it would roll forwards again. After some months I started trying to get it to stay back for longer periods of time. I remember using the round part of a regular rubber balloon with the thin bit that you blow into and tie cut off as a device to keep my foreskin pushed back as I slept, wearing it over my glans a bit like a condom. I love playing with condoms and rubber cock and ball sheaths to this day.
After a while and with the onset of puberty, which made my cock grow but left my foreskin behind, my skin stayed back much more easily until it reached the point where it seemed to prefer to stay retracted. If I was to push it over the head it would roll back by itself. I've always peferred the look and feel of the exposed head and at the time I thought I was the only boy doing it and to this day I get a thrill if I see a cock with the head exposed. It simply looks sexier to me, while a cock with the foreskin covering the end looks juvenile.
I wore my foreskin permanently retracted for many years but I did have the courage of my conviction and at the age of 31 I decided to be circumcised. My experience is that it's so much better without the skin and my only regret is that I left it so long before choosing the circumcision. I'm not saying it's right for everybody but it is for me.
I can wank dry or with lubrication but for extended edging sessions I'll often wear a condom or a rubber sheath because I enjoy playing with them and ejaculating into them so much. My preference, when playing with another guy is for him to be circumcised too but if he has a foreskin that's not a problem as long as it's clean and retracts fully.
Tight, unretractable foreskins do seem to be on the increase here in the UK. OK, some people find phimosis a turn on, which is fine. What I'm talking about is the seemingly increasing number of men who can't skin back and who rather wish they could and who feel the need to apologise. They can be helped and I don't necessarily mean by circumcision because the foreskin opening can be stretched gently, the important thing being not to tear it and cause scarring.