<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 17, 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 23, 2013
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
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.
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
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 5, 2010
by Wendy (bob's girlfriend) October 12, 2008