painful and long-lasting election

The 2008 American Presidential election

Barack: Man, this race is going on too long.
Hilary: I agree, old bean. This is truly a painful and long-lasting election.

by Jean Shepherd ex-K2ORS (SK) July 25, 2008

Painful

Intense pain, next level of pain.

Pissing Saints off could be very painful.

by Saints October 19, 2003

Genuinely painful understanding

An understanding of a concept so strong that you have a disturbing understanding of it, no no no you don't get it like I mean someone can still know about it, but not know as much as you do, usually in a depressing "oh godi get it now" sort of manner, the more of this painful knowledge is amassed the worse ones mind becomes.

gary: oh god i understand.

larry: why what?

gary: the full saying isn't blood is thicker than water.

larry: what do you mean

gary: its "the blood of the covenant is thicker then the water of the womb"

larry: and that bad because?

gary: everyone thinks that blood relatives are more important

than friends because some fucker wouldn't say the full thing.

larry: oh god.

gary: this is a Genuinely painful understanding of the world as i know it.

by steve man mcgee February 8, 2022

Painful Orgasm

painful orgasm = orgasming when cramping at the same time, creating a strong feeling of pain and pleasure, afterwards leaving only slight pain

After masturbating for some time to ease her cramps, sally had a painful orgasm.

by Emilychan666 June 28, 2010

painfulpvp

a cringy faggot with oversized glasses

I like to sing bob the builder I'm painfulpvp

by PainfulCringe September 19, 2017

The painful parrot

Basically any sex position can be used but anytime your partner says anything you repeat it in a parrot voice then slap your partner in the face... That also applies for your partners exclamation of pain and their repeated pleas for you to stop slapping them

Sketch: My girl said she wanted to try something new so I surprised her with the painful parrot.

Jeremy: How did that go?

Sketch: I'm now single.

by sirsketchalot July 16, 2017

Painfulest

When your Bibba does the worst thing to man-kind so you have make up a word

Wow,this is the most painfulest thing ever to me.

by OffcialScienctist April 8, 2018