The Kingdom of Loathing

Only 2 ascensions and you are cheating already D: (only kidding heh, what does KoLMafia do? i've heard about it but don't know any specifics)

11 ascensions and counting, no cheats yet (though i did use some minor greasemonkey scripts for a short while)
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My class won't show up, because i'm trying out the new class released yesterday, Avatar of Boris.

I could have a lot more ascensions, but i used to play more casually, only recently have i started speed-running ascensions.

I wanted to try the new challenge too. ): It had to come on the day after I ascended to a Disco Bandit.

And I'm in the same boat as you. I used to play really casually, but now I'm trying to get into the groove of speedrunning ascensions. And I use KoLmafia to semi-automate the process of playing (saving me time and mouse clicks from doing repetitive stuff over and over). And before you go say that I'm hacking... it is perfectly legal to use with the game as declared by KoL staff. It's how the buffbots like Noblisse Oblige work with.