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Dick Lickin Dan 

The guy from the bay area San Francisco who went on a dick licking spree for 12 days before autorities caught him back in 1978. He would break into your house and lick your dick and then bolt out the window, door, etc... He has since then served his sentence and now he is an elementary school teacher at a san francisco public school. Dick Lickin' Dan is now used as an insult rather than a name of the infamous Dick Lickin' Dan of 78'
FRY GUY: here's youre order duuuuuude (in a stoner voice)
CUSTOMER: WtF DICK LICKIN DAN! u got my order wrong.
Fry GUy: whhhhhhhhhhat?

dick measuring contest 

A conflict in which two parties (ususally male) are vehemently disputing something of limited relevance. Generally, both parties are somewhat wrong, but each refuses to be back down for fear of being thought the have the smaller of their two penises. Similar to a pissing match, but generally, the conflict involved involves a larger element of machismo, and continues on only because neither side wants to be seen as the one who backs down.
The White House and the Conservative Right have been in a real dick measuring contest over the qualifications of this new Supreme Court apointee, Harriet Meiers.
dick measuring contest by Cosmo October 12, 2005

Donald Dick 

A micropenis; an unusually small penis.
The artist portrayed U.S. Presidential candidate Donald Trump with an apparent Donald Dick.
Donald Dick by Ruthless Bates February 24, 2017

crank that dick cheney 

when you go hunting with your friend and you ejaculare all over their face
i'm gonna crank that dick cheney with tom

Dick Down December 

Following “No Nut November”, Single men smash as many females as they wish in the month of December.
Guy 1: Bro, it’s finally December! You know what that means?
Guy 2: Christmas presents?
Guy 1: That and it’s also Dick Down December!
Guy 2: Oh yeah! I’m ready for it! I’ve been waiting for No Nut November to end!
Dick Down December by KingTau November 8, 2018

Unsolicited dick pic 

When a man doesn't warn his parter before he sends a picture of his dick
Girl: Why the fuck did u send an unsolicited dick pic?
Guy: I thought you like surprises...