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Herman Cain

An ass grabby boss, higher up, shot caller, or well networked individual who assumes any pretty women in a cute outfit wants to fuck him in exchange for jobs, access, or free pizza.
I'd wear my Louboutin's to my performance review, but I don't want my boss to go Herman Cain on my ass so I'll wear pants and clogs instead.
Herman Cain by Evewasframed November 7, 2011

Herman Cain

To push your girlfriends head towards your crotch in hopes of oral satisfaction.
Bill: "Dude, the movie we rented last night was so boring, I decided to Herman Cain my girl in hopes of passing the time more quickly."
Wayne: "That's awesome man, did she oblige?"
Bill: "Hell no! She said she was going to hold a news conference tomorrow with Gloria Allred and tell the world."
Wayne: "Dauumn!"
Herman Cain by battenrw November 9, 2011

Herman Cain

a sex move wherein you slide your hand up the girl's skirt to the crotch while simultaneously pushing her head down to your crotch while asking "you want a job, dontcha?"
"I pulled a Herman Cain on my date last night. She scratched me and said she never wants to see me again."

"That sure is a pimp move, dawg!"
Herman Cain by Lamont Sanford 5 November 15, 2011

Herman Cain Award 

An award for individuals who vocally opposed masks and vaccinations in response to COVID-19, and then either ended up in the hospital or died.
Person A: "Did you hear about Doug? He died of COVID last week. His family watched it happen on an iPad. So sad."
Person B: "Wasn't he bragging two weeks ago about injecting horse de-wormer up his asshole when he got diagnosed? That guy was a real Herman Cain Award winner right there."
Herman Cain Award by Y2k September 2, 2021

rock you like a Herman Cain

A black guy promising to put the moves on a large breasted, blonde white woman before he runs for POTUS.
Here I am!
rock you like a Herman Cain!

Herman Cained 

One who does not believe in the legitimacy of a disease or illness, only to die of it.
Yeah, my Uncle Bob was a huge Trumptard and didn't believe in the risks of COVID 19, only to be Herman Cained a few weeks later. RIP!
Herman Cained by Wack Jab August 12, 2020