I did a challenge a while ago when Skyrim Special Edition came out. I played as a female character with a nude mod, & the armor I could wear was inversely proportional to the clothes I was wearing. If I was fully clothed, no armor for me & vice versa. It was quite good because you would have to pick what type of challenge you wanted, & could adjust it on the fly.
I have also done multiple fap roulettes based around League of Legends & Overwatch that required me to be naked or crossdressed & to perform acts/dares while I played.
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