Mostly been a mountain biker but am putting more and more road miles in the last few years. Never had a problem keeping the boys in place riding but since riding on the road a lot more, seem to have to adjust the boys in the chamois more. They seem to move around more and, excuse the visual, have to pull everything up every now and then when on the road bike. Usually wear only baggies with built in chammy while mtn biking and have no problem. I also generally like very minimal padding. Feels like I'm riding with a diaper with some brands. Zoic and Cannondale shorts seem to be the most comfortable.
Could it just be the different riding position on the road bike making them move around or has the effect of 36 years of gravity making everything hang lower making a difference? Seems like the jock might cause some chaffing down there.