DERAIL; a term used by the shmoo clan in order to replace shit, do it, and pwn.
1) Dude i have been holding this in but i really gotta deRail!!
2) Are you ready? Lets deRail!!
3) Dude you just got DERAILED!
by Nathan C. August 26, 2005
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Attacking or failing to follow the tactics of a debater who railroads the conversation, by expressing unexpected views or challenging logical fallacies.
She's upset because I took a third option that will derail her planned one-sided conversation.
by Poor Lurker August 2, 2012
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<Verb> The act of blowing a joke or a rip, usually by sputtering out sentence fragments or by stuttering. This usually leads to laughter by one's friends and extreme embarrassment to the person who 'derailed.' The offender will stay very quiet for a long period of time following one of these outbursts.
"Man, you're so stupid when god handed out brains you thought he said trains...and you went...and got on...and went for a ride...wait....goddammit!!!"

"HAHAHAHAHAHAHAHAHA HOLY SHIT, you're retarded!! Nice derail, Jay!!"
by Jamon26 February 17, 2010
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The act of passing gas on an up escalator, while inadvertently (or purposely) farting in everyone else's face who is behind.
I totally derailed some people at the galleria today!
by darthxduder November 23, 2013
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To move from the pink, to the brown, when making the sweet sweet sechzor.

Or if you'd like it a bit clearer:

To go from vaginal to anal intercourse
Man A: Dude, I tried something new with my girl last night.
Man B: Oh yeah, what's that then?
Man A: Well, I went from pink to brown.
Man B: Oh...you derailed!! Fair play matey.
by Sid P June 13, 2007
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When you are railing your rib, cleopatra, bottom bitch, and wife of 14 years. And you slip into the wrong hole. This is called a derailment, and doesn't matter what hole.
Jim: fuck this feels good
Susan: oooooohhh ya harder harder
Jim: (slips into wrong hole)
Susan: ooooaaaahhhhhhhh

Jim: sorry babe I derailed
Susan: ok, next time I dont cause a derailment into me
by Cochieman 456 November 27, 2020
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To derail someone means while having sex you slide up off the penis that is placed somwhere inside the your body.
I was getting slammed and was tired so I derailed with no hands and went to bed.
by Ayy Finn November 5, 2010
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