For some reason I suddenly can see your pictures. And your point!
Just an intuitive thought: because it used to be so very thight, all the skin seems to get together in a narrow ring. Making the ring stronger. Possibly stretching in the length will help it adjust better arond the shaft. Because it lessens the toughness of the ring. It is possibly the combined forces effect that might make the ring narrower over time, but not wider. When you try to spread out that force, each millimeter will have less strength and thus expand faster.
Just a thought.
In my case, it was never really an issue how LONG my combined skin was. More an issue of moving around freely. Like my scrotum has been expanding and contracting all my life. Contracted everything is in its place and firm. Not much to do with how low my balls can hang when at the lowest. Now that is all the same skin. Penis is different sections. Rigged band was very slow for me to adjust as well. I was narrow, but a little less then you. I actually still see my rigged band. After all progress, it is still not completely "skin like the rest of the skin". And yes, at certain times, when I sit and bend forward, it still is that rigged band that pushes the skin back over the glans. Nothing else. After all that time and effort.