Inserting a lollipop into one's knob hole and deep throating a woman with it. At the point of cumming the man take out the lollipop cumms on it and hands it to the woman.

This extremely kinky thing has been banned in the province of Skyrim for 150 years.
By Harry McD. Lollygagging
by l Meraxes l December 19, 2012
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To do a lot of talking about nothing very important.
The girls were lollygagging all night about the new boy in town.
by SKYPEARL November 3, 2011
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Lolly:gagging- to Pussyfoot
you were lollygagging when slobbin my knob. Quit pussyfooting around.
by 307joe July 29, 2011
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lollygagging is a phrase some people don't know what it means or uses it as an excuse!
I like to accuse people of lollygagging
by nascarfan90 March 8, 2019
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(Verb) Th action and resulting noises that happen when someone named Lolly is "servicing" a guy with too big a tool.
Big Jim was so well endowed that when Lolly was trying to blow him she ended up Lollygagging and spit up all over his new shoes!
by czbg September 25, 2013
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To choke on a lolly.
Tate was dickheading around with a lollipop in his mouth. Predictably, he ended up lollygagging.
by Blue Socked Llama August 19, 2007
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