Thanks very much to Uncut and Happy for his story entitled 'My Awakening & First Orgasm' when he was nearly 13. I thoroughly enjoyed it. I do love first time stories of boys. Anyway, like yourself, I had one of those tight foreskins that would only retract about half-way back on my glans, but there was another factor involved with my foreskin that kept me from even trying to get it to to back any further, although I knew it neeed to go back.
I had been jacking off since I was nearly nine years old and experiencing 'dry orgasms' even on my very first time, so I could move my foreskin back and forth enough to reach my orgasm real quick. However at this time, I was already 12 years old with a foreskin that had never been retracted very much.
My problem was a little tag of skin that had my foreskin attached to the top part of my glans near my pee slit and I was afraid to retract my foreskin back far enough to break this little small skin tag as I was afraid I might damage my dick someway.
My older cousin and I who was nearly 15 at this time were frequent mutual jack-off buddies and just about every time he would be jacking me off, he would ask me if I wanted him to push my foreskin back a little further on each stroke so this little skin tag would break and mke my foreskin free, but I would always answer 'NO' don't do it, It might hurt me someway.
Well on this particular day, both of us went down into the wooods to our special jacking spot for our afternoon penis play and as always he would always jack me off first, then I'd do him because it took so long to bring him to his orgasm, whereas I could have had 3 or 4 dry orgasms in the same time period. As I lay back on the leaves enjoying those wonderful sensations emanating from my little hard penis, cousin asked me the same question again, did I want him to slide my foreskin back far enough to sever this skin tag, but again, I said 'NO'. He didn't say anything but kept on stroking my 12 year old penis but as I lay there with my eyes shut I could tell he was going back further and further with his downstrokes as he was stretching this tag of skin a little bit more with each succeeding stroke, although there was no real pain involved. Anyway in another second or two I did feel an ever so slight tinge of pain and as I raised my torso up to see what had happened, I said, 'what was that'?. He said the little skin broke as I looked down at my penis and didn't see any damage, fell back again on the leaves as he finished me off to a good dry orgasm.
So from that day forward, I did what you did, I started stretching it back a litttle bit at a time, until I could get it all the way back, but I wouldn't on purpose pull it back behind the ridge of my glans, because as you said, it was very difficult at times to get it to go back over the head. The only way I could get it back over the head was for my dick to be completely soft, so if the foreskin was retracted behind the glans during jackin-off, I would have to finish to my climax in that position, but I very seldom let my foreskin go back that far.