I found that if I wrap and hang in the fully flaccid state it will slip right off. So, I’m doing it with a very slightly engorged unit. You’ll have to do some experimentation to figure out just how much of a semi you need. I’m pulling the skin all the way back under the HTW, which seems like it would increase the chance of it sliding off, but for me it works best.
As for the wrap, I did the HTW as mentioned in the post above and used that same crinkly brown wrap over it. Letting the hair tie material extend about halfway onto the glans adds comfort. I start the brown crinkly stuff just behind the glans and wrap backward toward the body, fairly tight. I tried it the other direction, seemed sensible since I was trying to keep some blood IN, but it didn’t work as well.
Once the wrap is applied, I do some squeezing, mainly to make the shaft thinner and to plump up the glans. If necessary, kegel some extra blood in there. I apply the Captain’s Wench about half an inch behind the glans. When the weight is on, it slides forward a bit, but shouldn’t be putting painful pressure on the glans.
Again, you’re going to have to experiment ‘till you figure out the right combination of skin pull, blood, wrap, and hanger spacing. Expect, during the first week or two, that there will be some times when you set it up, apply weight, and have to start over again because it doesn’t feel right. Eventually that will become rare. Good luck, it can be done.