smiling caboose

When you take your first finger and middle finger and twist them together like your crossing your fingers, but you straighten them (still crossed) and you stick them in your rectum and uncross them. Enjoy

Last night we were doing in and he gave me a smiling caboose.
Please baby let me smiling caboose you!

by Atomic Shadow & Smil3kills August 25, 2013

obtuse caboose

1) a: a big fat booty (as opposed to "a cute" booty)
b: a tushy exceeding 90 degrees
c: an exceptionally wide train car bursting at the steams
d: the rear region of an obese person
e: an incredibly vast rump

1) "Wow! Look at that obtuse caboose!"

2) "Hey, Can you move? I can't get around your obtuse caboose."

3) "Hey, you need to train to turn that the obtuse caboose into a cute caboose!"

4) "Let's take a tour of the obtuse caboose!"

by geometriclogos November 25, 2019

Red Caboose

When your old lady’s on the rag and you eat er ass out from the back

I really wanna give my wife a red caboose tonight

by Back country gravy December 23, 2020

Santa in the caboose

1. Anal intercourse on or around the Christmas holiday.
2. Anal intercourse while the giver is dressed as Santa Claus.

After we finished wrapping the kids' gifts and placing them under the tree, my wife asked for a Santa in the caboose. So, I slid down her chimney and got soot on my Yule log. Ho! Ho! Ho!

by James Island thriller December 4, 2021

chaboozeshney

Chaboozeshney: a word orginally created by a Londoner, who sought to create a multi-purpose word which can be substituted for any word. Thus, Chaboozeshney was created, depending on slight differences in pitch, lenghth and emphasis this word can mean absolutely anything.

I went down to the chaboozeshney. How are you chaboozeshney. Can I have a chaboozeshney?

by Tom Li February 7, 2005

Caboose Robber

A Homo-Sexual who like giving anal sex and not getting it.

Jody doesn't like to take it he only gives it, that Caboose Robber!

by Hugh G. Rekshon August 21, 2009

sour caboose

When you are giving a girl anal and she is in a bad (sour) mood and she just wants you to finish and go to bed

-did you get that pussy last night?
- nah all I got was the sour caboose.

by jokuden August 5, 2016