I just got the stealth passive stretcher. I have an issue with stretching in general. I put the ring up to my head against the ridge, but at the top, it kinda keeps pulling back under the ring making like a V where part of the ridge is pulled back underneath the ring. I experience the same with hanging as well. Does this mean that the rest of my penis will stretch longer but I've hit a stop with the top of my penis? If so, is there a specific stretch just to stretch the top out longer since that seems to be the main limiter of my stretching?

I don't have this issue while erect and I will get more length that when I am flaccid. Does this make amy sense?