Depends. If I am already oulling down elastic waist of shorts or sweatoants, usually pull down jock front as well. Sometimes pissing outside and going more handsfree I can tug the shorts or sweats down and pull the jock aside, otherways the waistband impedes urine flow inside the cock without...
Unrelated to the content, but something I just noted looking for followup, this thread only took at most 43 minutes to show up on a DuckDuckGo search. I forget if they use Bing or Google's engine on the backend.
I added KFC Radio Barstool to my podcasts to listen to the Burt Kreischer episode, I've ignored it as obnoxious otherwise but it popped up again when I did an episode search for "jockstrap". Uninterested in the the title discussion,
but skipping ahead to chapter marked "jockstraps" on both audio...