I will give you a little of my history, for what it is worth, jdm. Over 60 years ago, in an attempt to be pulled back, I had come across the info that the frenum needed to be freed to facilitate this state. I was able to thin it which did allow a better pulled back. I also developed a rubber ring that I have discussed earlier, made from liquid latex, to hold the foreskin back.
However, these steps never did give me the perfect ability to stay back freely. It wasn't until I started to wear snug briefs later that I was able to achieve perfection. I am a bit in the shower category so the following may be one sided for some. When I was dressing, or placing the penis back after relieving, I would pull the shaft skin well up so the foreskin then was smoother. In addition, I would ensure that the penis was not hanging down around the scrotum but was resting high up on it with the snug brief holding it in place. This would ensure that any downward movement of the glans would keep the shaft skin still high and folded with the foreskin not having folds.
I did this process over a few years when I decided that I wanted the foreskin to cover the glans again. I found that the shaft skin then was so tightly folded that it was impossible for it to stay that way without taping the prepuce, as in an artificial phimosis. It took some 5 years of taping before it would finally stay covered over the glans. By the way, the foreskin/glans had become so dried out that I had to then apply a cream of some sort to provide artificial lubricant for those years.
With the shaft skin having smoothed out over some 26 years, now it was not only the glans having to get used to being exposed again, but also the foreskin staying pulled back. However, with the shaft skin being thinner, it forms finer folds making the ability to stay pulled back easier so that I can stay pulled back without any aids of any kind again.
What I have described may not be of interest to those that choose not to have their frenums freed or choose not to wear restrictive items of any sort. But if it is of any interest to you, jdm, all the best!