The exceedingly uncomfortable and inconvenient bent-far-forward position that you are forced to assume when sitting on the toilet and trying to urinate, but you have a "stubborn" boner that refuses to "relax", and so you have to awkwardly lean way over with your head down between your knees in order to rotate your abdomen far enough to get the tip of Mr. Happy down into the bowl.
It's a good idea to take a good long whiz **before** "getting it on hot 'n' heavy" with a luscious chick --- especially if you also take a Viagra/Cialis pill prior to said bouncy-bouncy --- to avoid any unexpected stiffy-squats.
by QuacksO April 16, 2019
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Man, David Bowie in "Labyrinth" still gives me a nub stiffy.

Sarah has a serious nub stiffy from Viggo Mortensen in Aragorn gear... I wonder why
by ArcheryNerd July 8, 2013
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a slang term for an erection, usually used in dominant female / submissive male relationships.
dom: does my sub have a stiffy wiffy for me?
sub: yes mommy
by urhahamomhaha August 24, 2022
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When a heaps rough person leaves a nightclub in his undies asks ppl for a favour on their way to work but gets in a fight with a lawyer that’s also a secret ninja
That dude pitched a tent in his ripped undies and left the nightclub to touch a stiffy bro now we can’t say if he’s been knocked out or he’s having a Power Nap
by Hectic Mooslie October 8, 2023
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Those moments when you’re up late and get a grade-a raging cock penis boner hard enough to penetrate the earth’s crust
Girl on FaceTime: hey lol let’s stay up all night

Guy on FaceTime: I CANT THE LATE NIGHT STIFFY HAS STRUCK AGAIN
by _The_Fool_ May 16, 2023
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|The act of putting in an up right position under the elastic waist band of shorts/sweatpants to hide an erection.
The boy had gotten aroused when seeing his stepmothers mid drift so he a had to stiffy-stuff his erection in his shorts.
by poopsackle November 6, 2015
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When you are depressed and jerk yourself off to try to make the pain of living go away.
I was about to kms last night so I just did a quick depressed stiffy to help
by Yo8484 March 17, 2017
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