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Desperado's Wager

Wordlessly and stoically brandishing one's penis as a last-ditch effort to win the heart of a reluctant female. As a result, she will either relinquish poontang or never speak to you again.
1. I gave up on ever being with Martha last night and pulled the Desperado's Wager. Needless to say, she has since defriended me on Facebook.

2. I laid the wager on Barbara at Giant Eagle and then we defiled the soup isle in a passionate frenzy.
Desperado's Wager by billcosby7 September 27, 2010
outlaw. Current literature indicates that desperado is derived from the spanish term desesperado which means a person with no hope. The term comes from esperanza which means hope. Adding “des” to the front makes it an antonym. Changing the ending “anza” to “ado” makes it an adjective and desesperado means a person with no hope. While this may be logical, it intuitively does not seem to fit well. I sounds like an Ivy league researcher explanation. I spoke with Native American oral historian and their oral history says that the term evolved in this fashion:

Spain created the Camino Real from Mexico to Santa Fe, New Mexico, in 1598. Camino Real literally means “Royal Road”. As such the road is protected by garrisons at intervals along the road. Spanish law levied a toll to travelers on the Camino Real in order to pay for these soldiers. The soldiers would stop the travelers and demand the toll be paid for them to continue on. In spanish “to stop” is “parar”. And as above “desparado” is a person that was not stopped. According to their oral history, the term desparado, described travelers that did not want to pay a toll and circled, off the road, around the military posts. The term became associated with “scofflaws”, people that openly disrespect the law. When the Americans immigrated into the area they modified the language of the region to suite. Words like “la reata” in Spanish became “lariat” and desparado became desperado. To me this explanation makes a better fit, desparado meaning law breaker is a better fit than desesperado a “a person with no hope”.
Desperados have been depicted in Western literature and film for decades. The movie Desperado is about a cowboy character running from the law. Which is appropriate for a person that shot the sheriff. He is a desperado, an outlaw.

The Eagles song Desperados has lyrics describing a cowboy wandering the range "out mending fences". This is not appropriate. Desperados are not necessarily cowboys. I thing the Eagles missed the target to this one.
desperado by Francisco Osuna January 28, 2007

debbie desperado 

According to Kim Kardashian it is worse than a Debbie downer. Debbie desperados are clearly more desperate, or in slang terms, a bitch thirsty !
Genevieve is over here trying to hang all over my man like a Debbie desperado .
debbie desperado by Student of hair December 22, 2017

Desperado Attempt 

A desperado attempt is where you would do almost anything to win. Normally used for gaming puposes. It's like breaking the fourth wall (by cheating) in order to win.
Say you are VS your friend in a fighting game. The desperado attempt would be if you would slam your shoulder into your friend so they would stop attacking you, and you kill them or even the odds for the win.
Kyle: Time for my Desperado Attempt!
*Hits Matt in the shin via foot*
Matt: Asshole!
Kyle: I finish the lap first, bitch!
Desperado Attempt by FWL January 14, 2008
a desperate criminal, so says the real one,
somebody who lives their life alone, but is desperate to be loved.
desperado by the great April 22, 2005
That definitions is as accurate as could be expected, until he missed the Eagles lyrics. "Out riding fences" is accurate because in those days, any fenced land was obviously protected by the local Sheriff and/or the United States Army. This is not a boundary of trespass that a wanted man would want to risk imposing himself on unless in the most dire circumstances. It say's nothing of mending fences in the song.
A Desperado would not venture on a rancher's fenced land for fear of being hung as a cattle thief.
desperado by Ratchet Thunderstud September 16, 2016