Your son is well on the way to buying his own swim briefs but would be too embarrassed to take you to the store's fitting room to check the fit. Casually (maybe after dinner) offer him $20 for new swimwear for the trip and suggest he gets something he really likes, don't attempt to suggest he gets a brief or men's bikini style and don't ever ask him to show you what he has bought, leave all that up to him.
Whilst on your trip together just go to the beach with him, don't mention what he may or may not be wearing, the more you tell him you want to see him in briefs the more shy and resistant he will be about it.
Finally when you are on the beach both stripped down to your skimpy swimwear act cool, go for a swim, lie around for a while, have lunch. Don't pull out the camera until he has forgotten what he is wearing and is comfortable in his swim briefs, get him to take a few shots of you first and then see if he is happy for you to point the camera at him.
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