It appears we have differening philosophies about this situation. Mine is that such activity is completely inappropriate. Moreover, I have my doubts that most games will be thorough when it comes to assuring the absence of trauma.
Therefore, I would suggest banning such activity altogether, regardless of whether it is "chaperoned."
Edit: I notice you said that you would give consideration to someone who indicated they had been raped in real life or that they would be greatly offended. I would think to most people that would serve as an immediate indication that such activity should be halted ASAP. The fact that the victim was a male playing a female gives less credence to your argument, as a man is less likely to consider the consequences of said activity.
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