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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.
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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"'
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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.
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When you bit a person's cheek off in a heat of passion, whether romantically or maliciously, and then proceed to stick your penis in the fresh wound.
"Back in prison, I bit that nigga's cheek off and gave that punk bitch a cheek job."
"Hey Tom, how did you like that cheek job last night?"