This is one of those things that, like anything else, a little practice goes a long way.
I’ve been wearing mine just for bulge augmentation for almost a year now, and it took me a while to figure out what worked best. Stretching first helps, and not just a little. I wear mine at the shaft base (not behind base) and it’s snug but not too tight; you can give yourself ugly little zit/cysts if you pinch the skin and trap it that way for hours at a time. Also, you may want to practice the bathroom unwrap/rewrap so you don’t re-tighten too much or too little when you go pee.
Incidentally, I’m also not huge- just under 6” ENBPL, about 5.25 EG lately. I can’t put it on and make it stay on when hard, has to be flaccid.