Dudes pretending to be girls online. Been there/done that, except it was way back in '94 or '95 when people still basically sent pics through snail mail and if you were lucky they had one online on an ftp site that would then maybe take 15-30 minutes to download on dialuip.

Like OP, I was curious, so I created two female characters who were roommates. Since seeing pics of people was rather difficult as aforementioned, you didn't need to worry about that aspect at all, really. You'd tell someone what you looked like, and they'd just accept it. The one gal I created was book smart, "intelligent" and all that sort of stuff. The other one, while not dumb was the more carefree of the two, liked to party, etc.

Both characters got equal amounts of getting hit on. By the way, this all occurred on what was known then as at "Ew-Too talker" based on the Elsewhere II code. It was basically a huge series of connected chat rooms, each with their own descriptions, like one might be outside on a beach or in a forest, etc. You had your own home ther for private chats and the like. It was actually a pretty robust program for the time.

Anyway, I'd often have both characters on at the same time and be having two separate conversations going and flipping between the two while linked in through two different connections, say Tallahassee Freenet and Denver Freenet so the "Super Users" (mods) couldn't nail you for having multiple characters.

It was all pretty daft and now I'm feeling nostalgic. Not for being the female characters, but how truly different shit was online back then. It was a you had to be there moment. Instant gratification took a little more work.