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Harry Potter and the Methods of Rationality

Most people already love Harry Potter and the Methods of Rationality which is like Harry Potter would be if it was written by Eliezer Yudkowsky[1].

It's sometimes annoying in the ways you'd expect -- I found the first couple of chapters unbearably smug. But it's fascinating for the way it takes the Harry Potter world as a backdrop for presenting a scientific or rationalist worldview.

[1] Because it is Harry Potter written by Eliezer Yudkowsky :)

Harry Potter and the Natural Twenty

Harry Potter and the Natural Twenty is generally reminiscent of Harry Potter and the Methods of Rationality but with a DnD munchkinism in the place of rationality.

It's not thought-provoking in the same way, and some of the jokes are tediously obvious, but people who liked Methods often said they found it very enjoyable and funny.

Tales of Magic University (NSFW)

Tales of MU is not technically fanfiction, but it comes from that sort of culture.

It's an ongoing story about a girl who goes to university in a DnD-inspired world.

It intermittently features many common fanfictiony sort of faults, but I also found it very very endearing, and have kept reading all the way through.

If you like the "magic school" genre, it's a good example of it.

It also features a lot of the main character coming to terms with her sexuality, and BDSM, LGBT, polyamory, trans characters, etc, etc. and quite a lot of fairly graphic sex scenes.

Whately Academy Stories (sometimes NSFW)

Whately Academy is a shared-universe fiction writing project about a school for superheroes. Again, it's not technically fanfiction, but has the same sort of style.

There's so much of it, don't try to read all of it. The safest place to start is probably with "Intro" and "Ninja 1" which are about most of the main characters, and start with them settling in to the school. Some of the origin stories before that were rather harrowing, and might be offputting. From then on, I read all the Jade/Generator stories, and then the Ayla/Phase stories.

Some parts I found very annoying or simplistic, but a lot I found very very endearing -- I fell in love with most of the characters, and how they learn to use their fairly random powers in increasingly interesting ways, the intertwining stories show different aspects of them, and how they all grow into who they are in different ways.

All the main characters are transgender, and this is often handled well, but sometimes handled in ways that made me very uncomfortable. I can be more specific if it would help.

ETA: Further suggestions added much later
ETA: Also see https://www.drmaciver.com/2018/05/trashy-fiction-recommendations/
ETA: Also see https://cartesiandaemon.livejournal.com/1056721.html e.g. Time Braid by ShaperV (Sakrua-centred Naruto groundhog day fic which AFAICT if much better than trying to watch Naruto: Shippuden straight. Warning for some disturbing sex stuff.)
ETA: Also from above, Super Powereds by Drew Hayes

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