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.
by Evewasframed November 07, 2011
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!"
by battenrw November 09, 2011
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!"
by Lamont Sanford 5 November 15, 2011

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