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3.
This is when you mistakenly fallout of the vagina and literally smash the sphincter or asshole of a woman during sex.
I was having some intense sex with this chick, but I derailed and ruined everything. Especially her asshole.
by namgorf January 21, 2009
 
1.
To have sexual intercourse.
A: "I hung out with that cute blonde last night."
B: "Did you derail?"
A: "Hell yea. I derailed. So good."
by DryLee November 05, 2006
 
2.
Derail; a verb. Used to indicate the exact point of derailment, AKA EPDI (Exact Point of Derailment Indication) A topic is derailed when someone clearly goes off-topic with posts which are obviously not associated with the original topic subject, or goes about anally raping the topic tavles by posting huge-ass pictures.
Let's derail that fucking topic!

That topic is bound to derail.
by MeMB January 04, 2005
 
4.
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 22, 2013
 
5.
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 02, 2012
 
6.
<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 16, 2010
 
7.
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