This story won the vote when I asked what else you all wanted to hear about, so without further adieu…
I used to play a very popular MMO religiously. I was among the elite of the server and had a reputation that preceded me. One thing that shocked me about this scene was that there were lots of actual women playing, and I would shamelessly flirt with any of them, not to actually hit on them, it was simply what I did.
Teamspeak group chats would occasionally turn into one on one conversations, but only rarely would it ever become something more. Red was a bubbly outspoken member of my group who took my flirtations seriously and before long we were exchanging private messages.
We would talk about wrestling as we were both fans, and she mentioned that she was always the practice dummy for her brothers when they tried out moves. Eventually we started to exchange pics. Doing so was not as easy as it is today, since not every phone had a camera and phone plans back then would charge per picture message sent. The pics she sent got progressively dirtier, starting off with tits and ass, to finger masturbation (including pics of her licking her wetness off said fingers), and on to object insertion. One pic had her with most of a beer bottle in her pussy, and another had a sharpie in her asshole long before /r/buttsharpies was a thing (or even Reddit for that matter).