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Puerto Rican tollbooth 

When a person tries to jam something soft into a slot for a hard object and subsequently causes a delay in forward movement.
Mid stroke he went limp giving her a Puerto Rican tollbooth, there was a brief delay in which he called in a fluffer to get him ready for action again.

Tollbooth on the highway of education 

n. Popular and well-earned nickname for the ETS (Educational Testing Service), who produces and sells the GRE and SAT assessment tests. This parasite hauls in more than $0.6 billion in student money every year from its illegal monopoly on the testing market.
Every high school and college student in the country has to throw some big cash to ETS, the tollbooth on the highway of education. If a student doesn't pay his toll, he is usually shitcanned and forced to slave away at a McJob for the rest of his life.

phantom tollbooth 

a way to reach a fantastic world in a book of the same name
phantom tollbooth by Ben C. August 31, 2008

The Phantom Tollbooth 

A book/movie where a bored kid, Milo, gets this crazy toolbooth and drives away to this weird world filled with puns(Sea of Knowledge).
Milo was definitely on something.
"You ever read The Phantom Tollbooth?"
"Isn't that the one with the boring kid whos like so emo?"
"Huh..."
The Phantom Tollbooth by Pblcnme October 20, 2006

tollbooth to heaven 

Church you have to put money in the collection basket to get into heaven
All the old people flock to the tollbooth to heaven to give money to pay someones yearly salary

tollbooth hoe 

A money-hungry, scheming bitch with an enormous, gaping hole just inside the minor labia; commonly referred to as Hillary Clinton.
Hillary Clinton is a tollbooth hoe and had made her husband pay dearly for entrance.
tollbooth hoe by therealronn October 2, 2017