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”

Rusty Jackhole by Alex the cock Cannon April 12, 2019

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

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

Jackhole 

Someone who is an irritating, annoying, stuck up ding-dong. Not as bad as a**hole however is equivalent to a**hat.

Martha: OH MY GOD he is such a jackhole
Abby: Oh ya that's David

Jackhole by TheCultoftheBeatsproutGrowers October 23, 2019

jackroll 

Almost the same as jacked. To steal, take.

Ah You should jackroll that neek there bredwin.

Yeh skeen blud.

jackroll by Big D. Liu November 3, 2004

jackroll 

In the black townships of South Africa, it means to abduct a woman and rape her. Named for a gang called the Jackrollers who did this in the Diepkloof area of Soweto in the late '80s.

There are some bad boys in this township, they are all about jackrolling ladies and hijacking cars.

jackroll by sumkalo September 29, 2011