Didn't read it all but only the opening when I was personally too young. Anyway the book lucky by the author of the lovely bones. I've read books with serious content in it like the first broken earth book and deeds of paksenaeian both which have rape/dubious consent but I was more than mature enough to handle that.
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My Advanced English class in High School made me read the stort story Bloodchild.
That was pretty WTF for me at the time.
Not really quite as bad as the others here, but I read the first two books of the Sword of Truth series by Terry Goodkind as a young teen before getting squicked out by it. The female lead almost gets sexually assaulted four times (one of them being when she rides into the middle of a battlefield completely naked for incredibly contrived reasons). The entire first half of the second book is the author's BDSM fantasy forced into plot relevancy. But perhaps the worst I read was some evil ritual that involved the villain cutting off and eating the genitals of a young boy.
So yeah, I stopped reading it.
I came here to talk about this exact series.
I think I read up to about book 8 and every one had some fucked up rape/bdsm shit.
The Wasp Factory. I mean the whole book is disturbing but the ending....
Go Ask Alice
Very good book but it goes through a young women's journey through SA, and hard addiction.
It's so creepy because you read the repeated sexual abuse of a minor through the eyes of the perpetrator who continuously justifies his acts and misrepresents Lolita's reactions. He's a very unreliable narrator. First he even becomes her stepdad to have better access to her. Then her mother dies, through a car accident just before she can call the police on him. Again this is recounted through Humberts eyes, so I'm thinking it was actually murder.
I haven't finished the book yet, it's kind of hard to read. It's been a few years, and I should be somewhere in the middle IIRC.
I read the A Child Called It series which is an autobiography about the abuse David Pelzer suffered at the hands of his mother and his experience with foster care.
Some pretty fucked up shit happened to this man. The fact that he grew up to be a functioning human being let alone put it all behind him is incredible.
Naked Lunch.
"The boy looks into Mugwump eyes blank as obsidian mirrors, pools of black blood, glory holes in a toilet wall closing on the Last Erection."
I mean thats definitely not the worst part. Dr Benway's medical experiments, the old people smother party, some horrific overdoses...
We need to leave then some surprises.
Exquisite Corpse by Poppy Z. Brite is an experience.
Day of the Oprichnik. I only wanted to read it because it is banned in Russia.
I read Hunter S Thompson's book about the Hells Angels when i was in high school and i regret it, i also really fucking hate bikers. Just rolling packs of rapists.
I recently read The Parable of the Sower and it really affected me, both because I felt empathy for the characters and because I saw some uncomfortable parallels in the recent history of our world. I also was disturbed by The Sparrow. Though frankly I wouldn't recommend it for a lot of reasons. Battle Royale is intensely violent, in a really personal way. For graphic novels, From Hell is a really rough read honestly, but also really interesting
Wish by Peter Goldsworthy. J.J. has always been more at home in Sign language than in spoken English. Recently divorced, he returns to school to teach Sign. His pupils include the foster parents of a beautiful and highly intelligent ape named Eliza.
As a fan of transgressive fiction, I've read quite a lot of fucked up books. Here's what I came up with off the top of my head - sorry, it's quite a long list!
Some different types of fucked up here (horrible fucked up and fun fucked up):
Cows by Matthew Stoke (not very well written, but very fucked up, a sick classic)
Anything by Carlton Mellick III, but especially Aspeshit, which is like Evil Dead on acid (semi literally). But he's definitely 'fun fucked up' not grotesquely nasty without humour. All Bizarro is fucked up and worth checking out.
Apocalypse Culture I and II are both intentionally fucked up compendiums of short pieces and art that will make you sick and angry, but also make you think about a lot of different things. Feral House have plenty of fucked up books that are worth reading.
Atrocity Exhibition by JG Ballard - experimental writing unlike most other Ballard books, but significantly more fucked up in parts. All Ballard is great and fucked up at some point; High Rise has one of the best opening paragraphs of any book, ever. Crash is probably second to Atrocity Exhibition in fucked-up-ness.
Marquis de Sade - Justine, 100 Days of Sodom. Juliette: (mentioned elsewhere) horrible imagination-run-wild in the worst way, but aimed at antagonising people against the aristocracy and satirising the extreme cruelty and nastiness of those in power, probably including himself.
UK publisher Creation books (and imprint Attack!) did "anti-books" as they called them - some fucked up stuff of all kinds there: from fun stupidity like Raiders of the Low Forehead to some really horrible stuff by Peter Sotos that was unreadable (even to me).
The Encyclopedia of Unusual Sex Practices by Brenda Love tells you all you need to know about human beings and a lot you never needed to know (eyeball licking fetishism is a thing, apparently).
Nick Cave's 'And The Ass Saw The Angel' is a wonderful pieces of fucked-up-ness and the reason for my username: a mute hillbilly recounts his sordid, psychotic life while drowning in quicksand, with biblical imagery and references, poetic 'Deep South' language, and lots of unpleasantness, especially from his parents. Kind of an ugly sibling to 'The Wasp Factory's.
Clive Barker's works can be pretty fucked up - Books of Blood is still his best work, in my opinion.
Supervert's 'Extraterrestrial Sex Fetish' was disappointing, badly written, and fucked up in boring but nasty ways. I'd avoid it, but it's a long time since I read it, so maybe I forgot a lot about it. I remember being bored and irritated, and little else.
Most Will Self books are pretty to very fucked up, particularly his early stuff.
Harry Crews was a wonderful writer, with some pretty fucked up stuff in Feast of Snakes and A Childhood - The Biography of a Place.
Chuck Palahniuk, Irvine Welsh, and William Burroughs all have lots of great fucked up work.
House of Leaves by Mark Z Danielewski is fucked up in terms of layout and typesetting as well as storyline. Some really effective parts, some get a little bogged down in their own cleverness. But very much worth reading. Not fucked up in terms of gore or sex, as far as I remember!
Patrick Suskind's Perfume is brilliant and fucked up, and possibly the only book that can change your sense of smell.
James Joyce - Ulysses and Finnegan's Wake are fucked up in terms of experimental style and language, and are wonderful pieces of writing, despite being notoriously 'difficult'.
Alejandro Jodorowsky's biographical books are wonderful and fucked up. 'The Spiritual Journey' is one of the best still.
That's enough for now - I'm sure I'm missing a lot!
The Last House on Needless Street by Catriona Ward!
Another I haven't actually read this comment but this post reminded me of The Turner Diaries and Thought Slime's video about it.