Most resorts now are clothing-optional; with nudity expected only in the pool area. Which means he has the option of keeping on shorts or a wrap around his mid-section after checking in. That should reassure him.
Beyond that, it's just a matter of him getting acclimated. After you get naked, just lead him away from the crowd so you can have some privacy. Seeing you being comfortable and having fun naked will probably be the only motivation he needs. I don't think it will take him very long to join you.
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