The model siblings posed next to the former jail-bird in a series of candid Instagram snaps.
Chris, 25, was pictured with his arm draped around the youngest Jenner sister as he posed with a cigarette in his mouth.
Kendall, on the other hand, appeared to be getting rather close with Chris’s musician pal Trey Songz.
Kendall, 18, and Kylie, 16, have also been spotted out partying with another of music’s resident ‘bad boys’, Justin Bieber.
Chris and Justin are reportedly good friends and have been seen hitting the LA night club scene together in recent weeks.
Both Justin and Chris are currently on probation after their recent run-ins with the law.
Chris recently served over 100 days in jail for violating his probation, which he was sentenced with following his assault on ex-girlfriend Rihanna in 2009.
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Justin was arrested in Miami for an alleged DUI, but was later cleared of the charges.
He was previously in trouble with the police for causing thousands of dollars of damage to his neighbour’s property after an egging spree.
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He is now on probation for vandalism charges.
We hope that Kendall and Kylie Jenner can be good influences on these troublesome pop stars!
Do you think Bruce and Kris will be happy about their daughter's new friends?