I've also been doing it for so many years that I don't recall ever feeling pain. (Sometimes I've felt some aching afterwards—I tell myself that they "ache" to be hidden again :-)). If after experimenting, you still can't find a comfortable "fit," maybe you can get by without tucking. Some t-girls don't tuck. Instead, they wear tight microfiber panties or girdle briefs that hold them quite flat. You can get by with this with many clothes, except the most revealing or skintight. You can experiment with this as well. But, I would agree that if it hurts, maintaining the tuck is not a good idea—will probably just hurt more and maybe even swell. Ugh! I HATE those ugly things. Nancy