While playing a game of Texas Hold'em on Pokerstars you get your chips all in with a huge advantage only to see the typical runner runner miracle cards that make you shout in disgust and feel like you have just taken a big fat stiffy in the bum.
Yo Mikey Holla, "I was playing Pokerstars last night and called a preflop raise with 55, the flop was Q5Q, so i bet and he pushes all in! I call and donk has AK! Thinking I have him right where I want the turn brings another Q and the river shows the final Q!!!!!!!!"

Mikey Holla, "Typical! You just got dealt the Stars Stiffy!"
by Jlove's$ February 3, 2010
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The Dublin Spire, a monument in Dublin, Ireland, which some see as a phallic symbol. The Liffey is a nearby river.
The government is going to build another useless monument like the Stiffy by the Liffey.
by Michael David Reisman January 20, 2009
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To have your woman spread out on the bed, then take a run across the room and jump naked, with your feet touching your ass and hands behind you on your ankles, all while sporting a hard on. Then land with full insertion.
Amanda was impressed last night when i ran across the room and landed The Flying Stiffy.
by duke dynomite September 30, 2008
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When a girl puts a peppermint into her mouth when she is giving a man a blow job. The minty coolness causes extreme pleasure and gives the man what is called a "peppermint stiffy."
Bobby- "Guess what happened last night."
Jim-Bob- "What?"
Bobby- "Cheryl gave me a peppermint stiffy."
Jim-Bob "NO WAY! Was it awesome?"
Bobby- "Yah man, it was filled with minty pleasure."
by Amanda Seyfried August 2, 2010
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When you wake up with a morning boner and you have to shit and pee at the same time, So you sit down to shyt but your morning boner wont fit into the toilet.
Friend: Yo, wheres your bathroom?
Me: In the back to the left.
Friend: Fool there is piss everywhere!!!
Me: I couldn't help it man... I had a Columbian Stiffy this morning!
by S3XU@L CH0C0L@T3 March 1, 2009
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noun, verb.

applies to males/transsexuals only.

someone, or something so unattractive, it causes the penis to recede within the body--a reverse of the action of where a male has an erection, which is commonly known as a "stiffy".
"hearing about your venereal disease really just gave me an anti-stiffy."

"when the porno film shoot went horribly wrong when the star actress came to work with the flu, anti-stiffies were had all around."
by atilla February 17, 2005
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a phase in which the male sex organ know as the penis, or cock, becomes some what aroused but has yet to become a full hard on erection. Also known as half staff.
dude she stuck her hand down my drawers nd i had an iffy-stiffy nd she got scared away!
by Zachs January 9, 2005
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