I just remembered the first and only time I ever engaged in ERP online. I was about 16 and I met a girl in an MMO called Mabinogi while playing on a female character. Our conversations quickly became sexual so we started regularly going into dungeons as a party of two for privacy because dungeons are individually instanced leaving zero chance of being walked in on so we could ERP in peace and I RPd as my character rather then myself. This went on for months and I would even make plans with this girl to wake up early so we could go into various dungeons for different scenery to ERP in. This was a more arousing, satisfying, and emotionally connected experience then literally any actual sex I had as a man. Looking back on this I can't help but think, "Lexi, you idiot, how did you not figure this out sooner?!"

A cool detail about this story that's kinda... Wholesome? At one point I confessed to this girl that I was "actually a boy" irl. She said she didn't care. I asked if she wanted me to stop "pretending to be a girl" and she told me to do whatever I was comfortable with. I continued to RP as a girl until she eventually stopped playing the game. Nothing at all about our interactions changed following my confession.

So that's my current biggest "how did I not know" moment that I can recall. What's yours?