Tim's friend has had ups and downs before, so there is a chance he just may not want to play this teasing game any more as it is not as fun for him as it was initially. At least for a while. His frustration levels at not having a girlfriend might affect his overall outlook. If he did, then the 4 of you could play some fun games of various sorts...
Tim - have you thought about changing how you go about getting your wife to reveal more, possibly to other people or in other situations. Maybe diversify how / where / with whom you have this fun. It seems most women are more willing to push the envelope when there is little to no chance of anyone they know possibly seeing them, so as to keep this sexy fun aspect separated from every day friends and acquaintances. Exposures can be "accidental" in nature like buttons popping off, sheer tops that show more in brighter lights, changing rooms at clothing stores, whether leaving a curtain slightly open while changing, or coming out to show you how a new top / dress / whatever looks. Of more deliberate.
Hope things work out with your friend.
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