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!

smiling caboose 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!"

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

Red Caboose 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!

Santa in the caboose by James Island thriller December 4, 2021

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.

sour caboose by jokuden August 5, 2016

Douche caboose 

A unessecarily large camping trailer or fifth wheel, preferably a toy hauler, driven by an asshat in a lifted diesel truck.

Looks like Ryan is taking his new douche caboose up into the hills for the weekend.

Douche caboose by Alberta Strong November 18, 2016

loose caboose 

When you have a sex train going and there are not enough people to make a full circle. The person in the rear is referred to as the loose caboose.

My swinging friends invited me over for a party. My girlfriend won't go. It is throwing off the numbers for the sex train. I hope I get to be the loose caboose rocking the train.

loose caboose by StyxxxCA September 27, 2009