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I had some of the same issues but Bruce worked with me to order a tapered Innerwear. When I started wearing the regular one, I loved it, but my head/glans kept slipping out of the ring. In addition, I was too “aggressive” when I stretched to measure, so Bruce recommended I go down a size. I’ll see when I get it.
Also, he sent videos of how to put it on. The second video of using the sheath to pull it through was great. Saved a lot of “pain” trying to pull the glans through. Thanks, Bruce, for all the help.