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Derailed 

1. During the act of doggy-style vaginal intercourse, the male, while recovering from a thrust, pulls out too far and his penis "accidentally" inserts itself into the girls anus.

2. An arctic map in the video game "Call Of Duty: Modern Warfare 2."
1.

"The other night my girl moaned some other guys name, so I derailed her. See if she does that again..."

2.

"Last night I was having some fun, then got derailed"
"You pulled out too far and got mud on your junk?"
"Worse. I got that shitty snow map."
Derailed by FunkyPunkyJunky March 20, 2010

Derailed 

A women losing her virginity in a very rough, hard manor.
Guy 1:Dude, I totally just derailed this one chick!
Guy 2: Me too!

derailed 

to fuck the shit out of somebody, then never talk to them again despite seeing them around a lot. Usualy occurs between upper and lower classmen in high school and college.
bro 1: jon derailed that chick at that party
bro 2: I know, shed in two of his classes to
Bro 1: awesome
derailed by jon Appleseed August 25, 2008