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[Stormrage]

I've recently read Cryptonomicon and just couldn't get THAT scene out of my head for a strange reason. I won't quote it here and spoil some people 900 or something pages of getting there, but I would like to start a thread to find the contender to the spot mentioned in the title.

Also, speaking of Cryptonomicon, there are many other hilarious sex-related themes in Cryptonomicon which are equally hilarious, but not as awkward as the cryptically aforementioned scene, which some people dislike because of their length and no apparent relation to the plot, but they, and other semi-plot related multiple page spanning bonuses, are what made the book for me.

[Duke 2.0]

 Open any Stephen King book. I kinda lost steam at the first book, but Dark Tower 1 had an odd one involving a ghost oracle spirit thing.

[Cthulhu]

The sex scene in IT is pretty uncomfortable.

[Grakelin]

My grandpa collects a long-running series of Western serial novels called "Jake Slocum". There is one sex scene in every book.

And yeah, the one I read included the obvious pun.

[The Transcendent Tyrant]

My grandpa collects a long-running series of Western serial novels called "Jake Slocum". There is one sex scene in every book.

And yeah, the one I read included the obvious pun.

Must be awkward.

Anything in Imajica is just "LULWAT". Some guy starts porking a man-like (not human, I mean like male-looking) alien thing that has a swirling vortex for a vagina and that's just the start of it. Lobstermen made of lobsterhands that rape small children, a pig-guy raping the aforementioned alien thing, two people having sex and imagining eating each other during the process...

The list just goes on and on.

[Eagleon]

90% of Piers Anthony has awkward sex or sex-related conversation. I still love him for his Adept and Incarnations of Immortality series, not to mention Tarot.

[Chutney]

The sex scene in IT is pretty uncomfortable.

That's the one with the

Spoiler (click to show/hide)

child orgy

right?
fuckin' gross

[MetalSlimeHunt]

The sex scene in IT is pretty uncomfortable.

Pretty uncomfortable? That was the only time I've ever taken a double take while reading to make sure my mind didn't just make somthing horrible up over the past two pages.

[Vector]

I was pretty discomfited by the scene in Winter's Tale where the dude seems to, er, thrust his way through multiple layers of clothing.

[Argembarger]

Song of Ice and Fire series, I forget which book but it's one of the first two.

The scene with the soldiers in the inn... pretty messed up

[KaguroDraven]

I was........uncomfortible, to put it lightly, with a scene from a book called "Warlock", its set in ancient egypt. Long story short, egypt currently devided into two kingdoms, two asshole cousins work their ways ento positions of power on each side then have their kings killed and themselves positioned as Regents. One marries both the King's daughters, one 16 and one like 12. The other marries the other King's daughter, like 14. Both the 12 year old and the 14 year old get very disturbing scenes, the 12 year old is worse, at the end of the book and she dies from it, and her sister is the one who does it.

[KaelGotDwarves]

I can't even remember the name of it, but there was this odd horror scifi novel that my friend recommended to me that featured a dwarfish midget main character and halfway through the book, out of no where, while avoiding human-collecting aliens and being frozen/being placed on meat hooks, the main character just hooks up with a prostitute on the spaceship.

And then there was the oral reading of choice bits of Stranger in a Strange Land in class. lolllllll

[Leafsnail]

I was pretty discomfited by the scene in Winter's Tale where the dude seems to, er, thrust his way through multiple layers of clothing.

...Ambiguity caused by bad writing, or just...?

[Vector]

Ohh, and I forgot to mention Mendel's Dwarf.  That is so full of awkward masturbation and sex scenes... it was really disgusting, because the author just couldn't stop reminding us that the "only regular-sized part of Benedict was his penis."  Plus, the adoration of the words "nacreous" and "tumescence."

Just... yergh.

I was pretty discomfited by the scene in Winter's Tale where the dude seems to, er, thrust his way through multiple layers of clothing.

...Ambiguity caused by bad writing, or just...?

No, the book was actually really good.  It was just that one part where he apparently rips through his pants and her dress in his passion, and then there's some more lurid descriptions of how this sex act was so different from all others in its intensity and heat blah blah blah.

[Mindmaker]

Open any Stephen King book.

This.
Thankfully most writers have the decency to not go into detail, when they include such scenes in their books.