If it's someone i dont know then i have no preconceived expectations of how the scene will play out. I am free to be myself and do what i feel is appropriate in the moment, based on the social cues given by the other(s) in the room. Start slow, and keep things easy and show in attitude an open, flexible demeanor to put the other guy(s) at ease. Basic etiquette.
I WILL NOT go out of my way to coddle or baby someone with social issues. We are men and men of a certain age should feel comfortable around other men without shame or judgement. But all participants in the room share the duty of building the social rules for the evening, and one guy should not take this freedom to a point where its uncomfortable for others.
I think wearing a tee shirt or boxer shorts or gym shorts (without underwear- meaning YES a stray testicle may be occasionally flashed) is a reasonable accomodation if the trip is planned. Once everyone has warmed to each other socially and trust has been built as fellow travelers and bunk mates, well MAYBE at that point inhibitions and jockey shorts will drop to the floor. But its a slow progression.
AND. I refuse to sleep wearing clothing unless i choose to do so of my own choice. I will not sacrifice my choice to sleep naked out of some sort of greater social good--- unless i feel that my roommate(s) may be hostile and that its better for ME to make that choice. I will drop my shorts to the side of the bed and slip under the sheets. No problem with that.
It's when i am staying with someone i know that i am more cautious- either to maintain the status of how the relationship is currently defined (friends, family, boss and subordinate, coworkers, etc) or to not escalate something unintentionally.
Some things cant be unseen or unsaid, so its best to just take baby steps a little bit at a time so that you know that your actions are welcome and that you are being viewed as confident, "normal" and appropriate.
And after all that is said, its a furkin' hotel room. Its like hardwired into any road weary traveler to strip down, relax, and "chill." Im not one to waste that opportunity so id be the first to drop my shorts on the floor and create a place where my night companion can enjoy the pleasure of doing the same.
When sharing a hotel room with someone you don't really know (for work, or a conference, or something like that), do you still sleep nude if you do normally? And do you strip down in front of them like in a locker room, or do you change in the bathroom with the door closed?