I tried this last night, medium difficulty with covers and nothing but the sock. I found it really comfy because the sock fits perfectly and the heal is just the right size to cup my balls. I finished the task as instructed by getting dressed as normal before removing the sock but then I decided to put it back on for the rest of the day.
I should add that I am uncircumcised so the sock doesn't cause any unwanted stimulation. I will try the dare again with my foreskin pulled back all night to see how different it is.
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