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!
2) Are you ready? Lets deRail!!
3) Dude you just got DERAILED!
by Nathan C. September 18, 2005

<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!!"
"HAHAHAHAHAHAHAHAHA HOLY SHIT, you're retarded!! Nice derail, Jay!!"
by Jamon26 February 16, 2010

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."
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."
"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

The act of passing gas on an up escalator, while inadvertently (or purposely) farting in everyone else's face who is behind.
by darthxduder November 22, 2013

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
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

To derail someone means while having sex you slide up off the penis that is placed somwhere inside the your body.
by Ayy Finn November 6, 2010

by Wendy (bob's girlfriend) January 22, 2009
