depressed stiffy

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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Late Night Stiffy

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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stiffy wiffy

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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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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