I'm a chubby bear with thick thighs. I refuse to wear the waist band up over my belly. I've come to accept that the waistband is going to roll so I look for boxer briefs or trunks with a soft cotton covered waist band. They may not be the sexiest but I prefer Hanes soft cotton boxer briefs. I also have found the new microfiber trunks and boxerbriefs to be very comfortable. They have a lot of give in the legs and ass. I have all kinds of underwear but mostly wear trunks. I tried bikini briefs thinking that they wouldn't dig into my belly. They don't, but the legs either gap or are too tight. I have never liked jock straps. I have large balls and the elastic fabric is very itchy. When I was younger I went commando for the most part. As an older man I like the security of a layer of fabric between me and my pants if you know what I mean.
Was the guy in the picture wearing any underwear? All I thought of when I saw that pic was spreading his cheeks. ;D