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When you fuck someone really hard.
You fuck someone so hard it's like a train getting derailed off the tracks.
"Greg derailed that bitch"
"I thought he had mono!"

"I'd derail her."
by Turbulence n' Jeff November 13, 2007
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When one person has strong feelings for another but breaks it off( through the phone) 😤
“Ya I’ve been DERAILED” said young Phillip
by Uncle Pen May 29, 2018
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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."
by FunkyPunkyJunky March 20, 2010
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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!
by Wendy (bob's girlfriend) October 12, 2008
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A band from stockport/manchester
Arthur - lead guitar/lead vocals
Luca - rythm guitar/vocals
Will - drums
Sam - bass
IG @derailerofficial
Derailer are a great band
by will galliway January 26, 2018
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The act of making any discussions gone off-topic

The extreme form of derailing is trolling, and because of the trolls, any discussions gone into flame wars/insult wars
Please don't derail the discussion, it's rude
by Sir. B June 30, 2021
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A: "I hung out with that cute blonde last night."
B: "Did you derail?"
A: "Hell yea. I derailed. So good."
by DryLee November 6, 2006
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