Cinnamon rolling is a handshake whereby two or more people all put their right hands in together so their fingertips touch, wiggle their fingers then cry "CINNAMON ROLLLLL!" while curling their arms round so that all participants are making a big spirally shape with their arms. It was introduced by the Australian psych band Pond, and has since been adopted by UK bands Swim Deep and Peace among others, often as a pre-show ritual.
For an example, see Freshly Squeezed's interview with Swim Deep on youtube, skip to 3.13.

Great for making friends with people at gigs "Hey guys! Cinnamon rollll!" At this point they either have no idea what you're on about (in which case explain) or they do, and you bond over this shared piece of pop culture knowledge.
by petmonsta May 15, 2013

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When you have to take a deuce in a portapotty then you suddenly get the urge to rub one out.
Dude check out that cinnamon roll I just made!!
by Johnnie Elliott October 25, 2006

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The act of performing a hot carl aka cleveland steamer on a girl, followed by ejaculating on top of the cleveland steamer to make something in the resemblance of a cinnamon roll.
I was with your mom last night and she got excited when I gave her a cinnamon roll.
by Jared S August 08, 2006

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Whhen you bust in the ass hole of a man/woman and then he/she proceeds to shit out a cum glazed turd, known as a cinnamon roll.
Steve, Tiffany pumped out the raunchiest cinnamon roll last night.
by Warpenis6969 May 31, 2016

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A small innocent-seeming person that’s actually not pure at all.
OMG Billie Piper in Penny Dreadful is such a cinnamon roll.
by thedoctordonna July 13, 2015

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When a large penis is folded and stuffed into a mouth; an act of oral sex.
Julie wanted to pleasure Tyrone so she gave him a cinnamon roll; he provided the icing.
by Timmy Sticks February 03, 2015

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When one ejaculates on another's asshole. Then allowing it to dry like frosting.
Mando gave this bitch a cinnamon roll when hitting it from behind.
by The 34 Block November 08, 2013

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