Having read the OP again, I think you could play mind games with such a guy.
Next time you are drinking together and he makes one of his locker room jokes about someone;s wife you could say.
"Hey, when I fixed your computer I noticed those cross-dressing photos of you and you look great in stockings too!"
It would sure raise a laugh with the other guys and how would he handle being on the receiving end.
Of course it's not true but he has to be careful about not protesting too much in case the guys think it's true , but what if he was into cross-dressing and he'd deleted the photos and thought he's missed some?
Then he'd wonder if you'd seen the pic of his wife, but wouldn't know whether to ask you.
If he did, you could just smile and and say no but I'd like to.
So you don't do anything really mean but just use the situation to reel in a guy who likes to joke at others expense.
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