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It's a D&D term where you tweak a skill of your character to the point of detriments in another skills, and the Dungeon Master specifically tailors the campaign to take advantage of that detriment, fully negating any point of pimping out the skill you were focused on. Thus, your character is skillfucked.

(Definition courtesy of MattK via www.ToplessRobot.com)
I'm sorry Brian, I guess you shouldn't have poured all your skill points in to bargain, since there are no merchants in this campaign. You my friend have been officially skillfucked.
Skillfuck by Swedish Jesus January 26, 2010
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Skullfucker 

Skullfucker (S'ck~uhll.fuh'ckurr) adj. Skullfuckery, verb. Skullfuck m/f Skullfucker:

A 'skullfucker' is someone who fucks you in the skull. Either in the eye socket, or mouth, or anywhere else where the penis can penetrate the skull, such as a hole smashed in the back of the skull with a hammer so you can feel the brains on your cock and shoot semen directly onto the area that gives people horrifying nightmares of dicks entering their skulls and shooting semen into their brains to impregnate them with the children of the master race of skullfuckers.
Suzy's a slut, she'll give you skull for weed.

Ashley skulled me all night till I busted in her throat.

Ethel has a glass eye so I skullfucked her socket and lubed it up with my semen for her glass eye. HAHAHAHAHAHA!
Skullfucker by D Pereira December 30, 2003

Skullfuck 

v. The action of inserting one's erect penis into the eye-socket of another person and proceeding to thrust your hips back and forth, thereby "fucking" their skull.
"Look at me while I skullfuck you"
Skullfuck by Temptation September 7, 2005

skullfuckable 

Your mother is skullfuckable
skullfuckable by David Loller October 4, 2019

Governmentally Skullfucked 

To have your eye removed from your socket and boned in the socket by the Gov.
We tried to raid area 51 and we were totally Governmentally skullfucked.

Skullfuckery 

Malicious mockery, directed at one individual, with the intention of causing that individual mental and emotional anguish on a comparable level to having their eye socket violated with a hard cylindrical object.
1: That was some pretty serious Skullfuckery there man.

2: Yeah, she's crying in the corner like you just raped her puppy.
Skullfuckery by spazmate December 8, 2009

skullsucker 

(n.) A jaded, stupid or unimaginative person who, by his/her negative or ambivalent reaction to another person's enthusiastic plan or idea, or by a general malaise about everything, sucks the life force directly out of the other person's brain.
I don't discuss my plans around him anymore; I've learned the hard way that he's nothing but a skullsucker.

She's the worst kind of skullsucker: somebody who thinks that her ideas about what's "realistic" are helpful.

Every time I leave that skullsucker, I feel drained and one day closer to death.
skullsucker by COrcutt February 13, 2014