I've been wearing male underwear until now. Tomorrow, though, I'm going to go shopping for female underwear for the first time. That's good. However, I'm going to need help and information with tucking before I do that, because I'm sort of lost.
In the beginning, I could do it pretty well. I just put it behind, stuck it between my bosoms and it held, mostly. But after a while - I'm guessing because since I pulled it up so much - my underwear got stretched, and it started to hold a lot less. It would, ya know, "roll in", a bit like those water-filled tubes for children you see at the dollar store do. Then I had to rely on moist down there to "glue" the tip of the foreskin between my bosoms. That worked, however when I sat it could easily start to hurt like heck because it pinched the skin, so often I had to undo it myself (in class - awesome).
However now even that doesn't work. I've had skin problems (some pimples, and many pores mysteriously gushing out yucky white stuff) "down there" for a while, and some testing revealed that the problems were caused by moisture. So since I now put baby powder in the whole area, I can't "glue" it anymore. And it's really uncomfortable because no matter what, the tuck will just not hold. And how awful does it feel when you feel it undoing itself and you can't do anything about it? Or even if you can, have to redo it endlessly (and wash your hands endlessly) because of it? "Very" is the correct answer.
So. Before I go out and buy underwear, I need to know how I'm going to make this hold. Because I figure that what underwear you have makes a difference.
Also, I'm going to go to a regular lingerie store, so at this very moment suggesting trans-specific panties or whatever might not be relevant because I doubt they'll have them.
Finally, it must absolutely not require crafting of any sort. You just cannot imagine how incapable I am with my hands. You cannot.
