So many different ways, so many different concerns. OK, so I can honestly say that I'm the old broad on this block
and will tell you that after more than 20+ years of tucking, it actually becomes second nature for your body to adapt. If this might help (and I hope it may), I will describe the method that I found to work for me.
I tried that taping method a while back and found out the hard way what it involves and the results. It doesn't matter if it's duct tape or medical grade, after a while you could end up with a rash that isn't very comfortable. I also tried that method where I held myself in place before pulling up my panties. Most of the time, either I couldn't get my hand out of the way enough for this to be effective all the time or trying to keep my dress up while pulling up my panties one handed was a bit of a juggling act. What I did find to work is that once my undies were up, simply reaching in and placing everything in place seemed more successful. And by the way, this works with hi-cuts, bikini style as well as boy shorts. Just remember to make sure that the material in the crotch area is wide enough to allow for coverage (string bikinis and thongs don't always provide enough).
Ok so on the comfort. In the beginning, yes it was somewhat uncomfortable for me. The feeling of being squished was almost always present. Even semi erections was a problem in the beginning. Just remember that the mind controls all body functions and that with time the body starts compensating. In the beginning, though most don't want to admit it, just the sensations of something other than rough cotton underwear has a somewhat exotic and sexually charged sensation. Over time, the mind adapts to the body structure and it almost becomes natural to be in this position. I have to admit that when I
am swinging free so to speak, it becomes somewhat uncomfortable for me.