Men In Dresses
Believability

I think that when your friend Dan is roleplaying Thargor the Mighty you have to be able to close your eyes and have a mental picture in your head of him as Thargor. Granted if Dan is five feet five, thin as a bean pole, with spots and glasses, whilst Thargor is an Arnie clone, this might be a little difficult. But you can do it. As Dan/Thargor enters combat you can be thinking to yourself: Yeah Dan/Thargor go for it, swing that sword, give the gorilla a right-hook to the chin!

But what if Dan is playing Lola the sexy hooker? As he describes that: "I'm wearing black stockings and suspenders, a mini dress that shows off my 32DD breasts, and I'm sitting on the cop's lap and grinding..." Are you visualising nicely? Or do you get some hideous image of your mate Dan in a dress?

In my experience when men generally roleplay women they don't actually roleplay any differently. I've actually played through about three sessions of a campaign before realising that two of the characters were female (it was a sci-fi campaign where you couldn't tell from the names).

Alternatively if someone really did try to roleplay a women, throwing in some vocal traits and mannerisms - I expect the effect would be more homosexual than female.

The mention above about the sexy hooker brings me to my second objection:
Stereotyping...

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