When a human head is compressed in a manner which causes it to pop.
A man crosses a street and trips in front of a car making a right turn. His head lies perfectly in line with the cars front tire and is slowly ran over, causing a quick pop as the tire reaches the peak of the head.

Onlooker: "ah man!! Did you see his head pop?!"
Onlooker 2: "ahh jeah, that head popped hard!"
by Tommy Horse February 2, 2011
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Repeatedly inserting the head, and only the head, of the penis in and out of the anal or vaginal opening.
I was head popping Rachel’s little brown donut last night.

I can make Rachel cum by head popping her tight pussy.
by Eaton Holgoode March 21, 2018
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When someone holds their breath and pushes blood into their head until they turn red and veins start popping
by Head pop master August 4, 2020
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Hey Chan, your head is quite large compared to your stringy body. I think people might call you Lolly-Pop head behind your back.
by Shauff December 29, 2011
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When someone is too skinny and there head looks extra large - like a lolly pop.
"Have you seen Megan recently, she has lolly pop head!"
by Fangman February 6, 2007
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