Ol' Switcheroo 

An ol' switcheroo is a woman pegging a man using a strapon

He said to his wife "Let's do an Ol' switcheroo"

Ol' Switcheroo by GeneTakovic August 14, 2024

The ol' switcheroo 

when a transgender person dates the gender they were born as without the other persons knowledge

yea I was going out with this "girl" when "she" pulled "The ol' switcheroo"

The ol' switcheroo by 7uck3r 573v3n5 February 24, 2021

The ol’ shotgun switcheroo 

An advanced sexual maneuver that invlolves a male that is proficient with firearms, a woman, and a (preferably 12 gauge) shotgun. The maneuver is started by having sex, usually in missionary position, but as soon as the man feels he is about to ejaculate, he removes his genitals from the woman and replaces it with the barrel of a loaded shotgun. He then pulls the trigger at the exact moment of his enaculation

Me: Bro I got arrested for murder a couple years back
Friend: Why?
Me: I tried the ol’ shotgun switcheroo

The ol’ shotgun switcheroo by awesomeplp9 November 11, 2018

The ol' spicy sausage surprise switcheroo supreme

When you trick your partner by using a ramen noodle spice package as a condom but then they give you a blowjob and taste the seasoning. They bite your dick with the intent of revenge but realize that you we're using a sausage casing full of chicken blood as your dick the whole time.

"I gave my girl The ol' spicy sausage surprise switcheroo supreme and she didn't call the cops on me"
"She's a keeper bro"
"I know I'm thinking of proposing this July"
"Oh no way, congrats bro"
"Thanks, bro"

The ol' spicy sausage surprise switcheroo supreme by SpikingThePuns July 1, 2016

the ol' Italian Switcheroofie 

the act of spiking someones drink, taking them home, and taking a roofie yourself, to even the chances, and escape charges

originated from Italy switching sides in the war

-My friend, Fernando, was on trial for raping a girl last week.
-Was he found guilty?
-Nah, he pulled the ol' Italian Switcheroofie.

the ol' Italian Switcheroofie by Cosbirius May 20, 2020