Painfun 

The easier to say and Anglicised version of the German word schadenfreude.

"Hey, did you see that old lady walk into the sign post? Totally painfun, bro."

"Taking painfun from those Youtube videos is despicable."

Painfun by WolfmanDan August 30, 2012

painfun 

1. Something that is considered painful, but yet is really fun.
2. A person who is a pain to be around but the things that they have such as a Wii are fun.

Person 1: That Jonah kid is such a painfun!
Person 2: Why is that?
Person 1: He is so annoying but yet his house has some of the most amazing things!

painfun by Ma-Rak January 19, 2008

Painful Debbie 

The act of getting a painful hand job by a muscular woman.

Dude why are you walking funny? I got a Painful Debbie last night.

Painful Debbie by jizzking October 5, 2012

painfull 

The feeling you get when you eat way too much and it hurts to be full.

Food baby is optional

In a diner with an all-you-can-eat option

Guy 1 : Maybe you shouldn't have ate the patty melts, buttered toast, scrambled eggs, sausages, biscuits and gravy, or the hashbrowns.

Guy 2 : Yeah, my food baby is due soon. All the eating was so painfull.

Guy 1: Asking for a second serving was also a bad idea.

painfull by Billy Billster July 15, 2010

Painful Boner 

When you get a painful boner after fapping way too many times in one day OR after having a stiffy for too long

Dan - oh dude i've got a painful boner

Joe- what the fuck dude? Stop whacking off.

Painful Boner by DKDKDJ December 3, 2013

Painfully Average 

A person who is painfully average would rate on a scale of 1-10 directly in the middle, a 5. This causes the person to become almost invisible because of their mediocrity rendering them completely undesirable. Therefore it's better to be a 4 than a 5.

I'd rather be with Rachel than Amy. Rachel's a 4 but it's better than being with a painfully average 5.

Painfully Average by Sundialist93 February 12, 2014

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