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The pleasuring of a man's penis using your butthole, aka sitting on a penis.
dude 1: Hey did you see that guys crank?
dude 2: Yeah, I totally wanted to jump off my Busa and sideboss him
sideboss by gootboxybox July 7, 2014
Related Words

Clown Sides 

The appearance of a vast amount of pubic hair protruding from beyond the bikini line, resembling the hairdo of Krusty the Klown from, "The Simpsons."
When Holly took off her pants, I assumed that 50 people would have jumped out of her panties based on those clown sides.
Clown Sides by UrbanBurban February 28, 2015

Sanders Sides 

An ongoing YouTube series created by the EX-viner Thomas Sanders.
Me: Aw man Sanders Sides is such a good series!!
Everyone around me: wtf is that??
Sanders Sides by tinajbee November 2, 2019
To download a file, esp. an application, to a smartphone or other electronic device outside of the accepted or usual channels.
The app center says the eBay app isn't available yet for the new OS on my phone, so I had to sideload an earlier version from a Dropbox link I found.
sideload by Eduardo Suave September 7, 2011

St. Louis Sidestep 

A slang racing term in which a driver starts out on the outside of a turn and then cuts to a sharp inside line to pass a driver that is near the center of the curve.
Kurt swiftly pulled off yet another St. Louis Sidestep which let him finish in first.

I see both sides like chanel 

A Bisexual statement made famous by Frank Ocean's song "Chanel," and it's supposed to be a metaphor since the Chanel logo has two C's facing opposite ways... c what he did there?
Boi: You gay?
Boi 2: nah fam, I see both sides like chanel