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

Derailment by Cochieman 456 November 27, 2020

Alabama train derailment

When family members are engaged in group sex with another family member and something happens (superficial or catastrophic) to bring it to an early or unexpected end.

We was all banging cousin Shirley out back at the family reunion when uncle Bubba's liquor still blew up and started an Alabama train derailment almost instantly.

Alabama train derailment by Gliterbob the Clown March 10, 2023

Holbrook Derailment 

When a woman is engaging in anal sex with multiple partners, and accidentally defecates on the still erect locomotive of the final man standing.

Bro 1 “Dude Buster’s mom was pulling trains last night. I got there late and went last. As I was pulling out she shits on my dick.”

Bro 2 “Damn dude, Buster’s mom gaves you a Holbrook Derailment.”

Holbrook Derailment by Mr. Doses May 15, 2024

Holbrook Derailment 

When having anal sex with many partners, a woman shats on the rod of the last man standing.

Bro 1: Dude your mom was pulling trains again last night. I got there late and went last. As I was pulling out of the station she dropped a log on my schlong.

Bro 2: Dude moms gives you a Holbrook Derailment

Holbrook Derailment by Merle’s Mom June 15, 2024

Holbrook Derailment 

When a woman is having anal sex with multiple partners and she accidentally shats on the schlong of the last man standing.

Bro 1: Dude your mom was pulling trains again last night. Got there late had to be the caboose. As I was leaving the station she dropped a log on my iron horse.

Bro 2: Dude moms gives you a Holbrook Derailment.

Holbrook Derailment by Merle’s Mom June 15, 2024

Detailment 

The sense of being detailed.

Saab ji, ek detailment aaya hai.

Detailment by AdhirajCounterstrike July 22, 2022

rerailment 

The act of bringing a conversation, more commonly on an internet forum, back on topic after comments have derailed the conversation from the main topic.

Thanks to John's rerailment, the conversation went on as intended.

rerailment by rbsfreak June 3, 2011