Painful stranger 

Male masterbatury technique where one use his off hand to slam down on the head of his penis with his palm at the point of orgasm

Last night I gave myself a painful stranger hurt like hellbutt thats the way I like it

Painful stranger by Tothmacher July 3, 2006

Painful Shits 

One of three things that we are all going to do.

Dane Cook (holding fingers up): We're all gonna lie, we're all gonna cry, and we're all gonna take painful shits.

Painful Shits by Painful Shithead October 10, 2008

Painful Laughing 

Laughing so intensely that your larynx, entire face, and possibly your abdomen starts hurting.

Usually occurs under the influence of marijuana.

1: I laughed so hard last night I just wanted it to stop.
2: You experienced painful laughing.

Painful Laughing by trex33 November 19, 2009

Painful peanut 

(n) the result of sneezing while passing a large turd of moderate firmness

I was on the can, and I had a mid-grump sneezing fit which resulted in a painful peanut.

Painful peanut by Sig63 July 27, 2018

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.

painful and long-lasting election by Jean Shepherd ex-K2ORS (SK) July 25, 2008

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.

Painful Orgasm by Emilychan666 June 28, 2010

Painful to read 

A book (usually given to a student by a teacher) which makes one want to:
a) fall asleep
b) jump off a cliff
c) fail the class just so he doesn't have to read the book
d) go back in time to find/find in the present the author that ruined their life and permanently damage them.

NOOOOOOO! It's painful to read! throw it away!

Painful to read by manatee dog April 18, 2011