In response to the original question, the idea of a woman being forced onto a traffic cone is a favorite of mine. I know they get kind of wide, but if the top is narrow enough to be inserted then you can guarantee you'll eventually find that painful point by pushing her lower and lower. In this case, I would recommend lots of lube, not because it would make it easier; it would make her more likely to slip lower and stretch her out more.
I also like the idea of seeing how many sharpie pens could be inserted, one at a time, over an extended period of time.
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