derail the gravy train

A phrase, meaning to obstruct the flow of money.

some bitch: You ran your mouth to your parents, and now your living in a camper. You sure know how derail the gravy train.

some dude: I don't care if they own estates in Europe, the West Indies and America. I do miss my Ferrari Enzo, though.

by Cunty Fresh Fanatic November 15, 2010

Derail

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

derail

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 July 10, 2007

Derailment

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

Derail

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 6, 2010

Derailed

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) January 22, 2009

derailed

to fuck the shit out of somebody, then never talk to them again despite seeing them around a lot. Usualy occurs between upper and lower classmen in high school and college.

bro 1: jon derailed that chick at that party
bro 2: I know, shed in two of his classes to
Bro 1: awesome

by jon Appleseed August 25, 2008