I've been sleeping naked for over 10 years now. As
@2xistTrunks mentioned before, it takes some getting used to. I stayed hard all night and had to wank too, when I started. That took just a few days.
It doesn't seem right to have your junk covered in tight boxers 24/7. Your balls should be able to breath
I noticed that since I'm sleeping naked, my (nightly) erections are way stronger. Not being blocked by fabric has its advantages...
I'd highly recommend sleeping naked to anyone!
I do so even when sharing a hotel room with (straight) friends. Used to remove my boxers when covered under the blankets... now I just undress. And also walk to the bathroom naked in the morning.