Verb born from The Simpsons 4th season episode: "Marge vs. the Monorail". In which a con artist with vage background in monorail design and construction convinces the town of Springfield to give him a large sum of money to provide the humble town with a monorail service. Only to spend the minimum possible, scamming the town with a dangerous and flaky monorail so he can go away with the vast majority of the money he was given.

It's rarely used to describe a person or an entity that lives off of scamming small populations with fake or vage credentials, experience, recognition etc...
Cinephile- So the romanian town in which Borat was filmed were lied to and they weren't told that the main character would humiliate them and their children in front of god knows how many people.
Spimsons fan- Oh shit... So Sacha Baron went to that town to monorail it?
Cinephile- ... You're not even wrong!
by Zierbo March 17, 2020
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A elitist train costing $50 a month connecting 150000 100 story building in 2121
Let's make a 1000000 story building this generation so we can say the new marijuana is growing well? Who cares about fruit lick right? Worry about my Pogo stick! We're going to add a monorail.
by Cody5050 January 26, 2022
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when a man layes naked on his back while a woman - also naked - moves in such a manner that her pussy glides back and forth, up and down around the man’s dick, much like a monorail train glides on its single rail. Important to know that no penetration is involved in monorailing. Monorailing is made easier as the woman’s pussy gets wetter and wetter due to the friction and motion.
She wouldn’t let me bang her, but she was totally up for some monorailing.

Monorailing is a safer and enjoyable alternative to sex.
by Mister Bob Dobbaleena April 9, 2021
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When 2 Guys touch dickheads. Link opposing pinkies (golf grip style) and stroke both shafts simultaneously in a shared push-pull method. Maintaining index and thumb pressure on there respective members .
Bro... I heard Chis and Braxton got drunk and did a Monorail.
by Gus Chiggians March 9, 2022
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Something that everyone seems to want but nobody agrees on how to do.
The term monorailing is based on the struggle to establish a Washington State monorail, which had a very, very, very long history of the same. Many years of agreement that it needed to happen, but many, many, many years of discussion before it could happen.
by Julesong November 5, 2009
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Verb, "To monorail" - Sex act where two men stand facing each other with tips of erect dicks touching. One man moves his fist back and forth over both penises, from the base of his, to the base of his partner's, and so on. The fist is the monorail car, the touching dicks are the length of track.
"Dude... did you and James fuck yet?" "Naw, man. We did some monorailing, but that's about it."
by reftsh July 5, 2018
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