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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
Related Words
a very kind thoughtful girl who thinks about others and not her self, she can be very mean if provoked, but most of the time shes nice, has a beautiful smile and can steal somebodys heart in a heart beat, she doesnt really trust a lot of people and if she trusts you your lucky. she has a kind heart but falls for the wrong people at time. she is a true friend
That girl is so nice shes such a jacole

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
This is what happens when you get so angry at the rude bitchy people in the world you combine jackass and asshole together.
Boy was that Marine recruiter a jashole!
Get out of my way jasholes!!
Jashole by Mitch_760 August 9, 2007

Jackhole 

it is a combination of Jackass and Asshole and I started using the word back in 1985 at Perry High School
you are a jackhole if you think Jimmy Kimmel and Adam Carolla started this
Jackhole by Byron Woody May 30, 2018