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I would have to say my first one would have to be on Yu-Gi-Oh! Online. It was really simple stuff and then I moved to gmail with someone I met on Phantasy Star 2's online mode. It started to go up from there and I just remember some of the old cringe I roleplayed. I'm so glad that I've gotten better over the years.

It was years ago on Yahoo Groups, either late 2000 or early 2001 (technically it was eGroups at the start, then Yahoo bought them, which was not an improvement). It went through numerous shifts. The core points was that it was set in a fictional school and said school involved plenty of dueling between the students (the person who started it was inspired by 'Revolutionary Girl Utena', pretty obscure but if you know you will see the inspiration). The original version was yuri. The original creator was fairly inactive when I joined and disappeared shortly afterwards. Me and (mostly) one other person essentially took it over. We also took

My first roleplay was in history class with this girl I was crushing on. We a romantic but smutty roleplay about two lesbians in the post apocalyptic world. We had a wedding, adopted a mutant child, lots of sex and then we started dating in real life. But it just didn't work out.