I have to wear underwear that has some support that holds my genitals upwards, against my groin, and not so much laying on my thighs, so I am able to walk with a minimal amount of waddle (I walk funny) If I try to go commando, or walk naked, I have to either support my genitals with my hand, or walk with a severe waddle. What I do is I wear briefs but I wear them backwards, with the seat in the front. They're a larger waist size than my waist. My right testicle rests, suspended in the fabric that is supposed to cover the lower portion of the left buttock. My left testicle rests in the bottom portion of what would be for the right buttock. I pull the briefs leftward a little bit. I tuck my penis over my left testicle and over my left hip. The crotch fabric lays against the inner side of my left buttock and sometimes slips into my butt-crack, wedgie-like, and I have to pull it out of my butt-crack. I hook the elastic waistband over my hips. I can only wear sweat pants, or pants my mother has custom made, as outerwear. I try to align the pull-string waistband of the sweatpants over the underwear waistband to help hold the underwear waistband in place.
Often, by the end of a day, the elastic of the underwear waistband causes discomfort from digging into my skin above my hips.