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Jackbooking 

When a man jerks off whilst on facebook. He may or may not have an additional tab opened with porn. Can stem from the combined need for social attention and control over one's own life.
Torre knew he would have to conceal his jackbooking problem from everyone, yet he still got a disturbing thrill from masturbating while on facebook.
Jackbooking by GuidodrivesaCaddy August 14, 2010
A jackhob is somebody who gives and takes of semen orally. It is a concatenation and contraction of 'jack' for masturbate and 'hobnob' for the sharing of drinks together.
jackhob by Boris Blank January 10, 2008

Rusty Jackhole 

When you have just the tip of your dick in a asshole, and you proceed to stroke your shaft until you unload your load of baby batter.
“She wouldn’t let me go deep. All I could get was a rusty jackhole
1. A thick military boot.
2. A common epithet, used to conflate someone with Nazism.
"I am still without any clear information as to what a jackboot is. It is a kind of boot that you put on when you want to behave tyrannically: that is as much as anyone seems to know."

-George Orwell
jackboot by nedlum February 15, 2006

Toxic Jackhole 

A narcisistic ex or current boyfriend who strings you along and keeps you hopelessly in love with him by telling you everything you want to hear, including, but not limited to, "you are my soul mate", "I've never had a connection with anyone like this in my life", etc. in attempt to fill his black hole of a soul. He is of course incapable of loving anyone but himself.
I changed Aaron's contact information in my phone to read Toxic Jackhole to prevent me from receiving his texts or phone calls.
Toxic Jackhole by I'm Done 888 April 24, 2011

jackhole 

To clarify, it was Jimmy Kimmel and Adam Carolla who invented the word while they were working on the Kevin & Bean morning show on KROQ.
Ah, those were the days.
Doc, the news guy, is a complete and utter jackhole!!
jackhole by Walking E July 13, 2006