A form of oral sex involving the positioning of the penis at a minimum 30 degree angle in the mouth, causing it to rub against the check of the blowjob administrator. The only reliable way to determine the success of a Cheek Job is to have an independent third party to observe and confirm that the penis is visibly bobbing back and forth in the mouth of the blowjob provider.
Cheek jobs are most prevalent two demographic groups: (1) younger teenagers that are inexperienced with blowjobs (and where the blowjob concerns a large penis); (2) For couples (but most usually men) who want to assess that they are 'actually' receiving a blowjob by monitoring the progress in a mirror, or through home made porn.
by Jiggle Swami May 24, 2014
when a girl has a huge ass and you fuck between her cheeks
Tyra had such a fat ass, that Isaac just had to giver her a cheek job.
by JizzyJake38 December 06, 2010
When you take an erect penis and give it a hand job, however you flip the direction and stick the man's penis between his legs and rub it against his butt cheeks
"My penis is lonely. I'm fiendin for a cheek job. Rub that shit on my cheek"'
by CheekMaster96 March 09, 2013
when you titty fuck a girl's butt cheeks.
I slammed that chick, finished it off with a cheekjob, busted all over her back.
by JBourne007 September 01, 2010