I've regretted a couple of dares that have ended up damaging items I hadn't intended to!
First, I had a dare from a good friend that got my jeans pretty dirty by the time I was done. I couldn't get to a washing machine due to the late hour, but I did a little hand-scrubbing in the tub. Unfortunately, when company came the next day, I had to move the still-wet jeans onto a drying rack in another room... and they were still wet enough that they ended up dripping a little on the wood floor. Because the floors were so old, I ended up having to refinish that area.
The dare was definitely not worth the effort it required!
Likewise, doing body writing under a white shirt, the permanent marker leeched onto the cloth and left an ongoing stain (usually I insist on dark clothing over writing now, for that reason).
I've also usually regretted agreeing to share (non-identifiable) photos, because I've found that newer playmates who ask early on then tend to ask for something new every few days. Since exhibitionism isn't a personal kink of mine, I always feel a bit taken advantage of when this happens, and am obliged to stop working with them altogether.
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