Kendall and Kylie cozy up with Chris Brown Credit: Courtesy Trey Songz

What will Kris Jenner have to say about this? Kendall Jenner and Kylie Jenner got up close and personal with some high-profile party pals on Saturday, July 26—bad boy rappers Chris Brown and Trey Songz.

Reality TV stars Kendall, 18, and Kylie, 16, spent the evening at a house party with Rihanna's ex-boyfriend Brown, 25 and his pals. And judging by the photos Songz, 29, shared via Instagram, the foursome were getting very friendly.

In one picture, Kendall, wearing a black crop top, pouts at the camera while Songz hugs her from behind in a tight embrace. Standing next to them, convicted felon Brown has his arm around a smiling Kylie, a cigarette dangling from his lips as he flashes his grillz.

Brown was released from jail at the beginning of June after a three month stint behind bars for violating his probation in relation to the Rihanna domestic abuse case.

And while dating rappers is nothing new for the Kardashian clan, with Kim Kardashian married to Kanye West, and Khloe Kardashian dating French Montana, this new friendship is bound to be a source of worry for mom Kris.

Already concerned about the influence Montana is having on Khloe, the momager is unlikely to approve of any friendship her youngest daughters strike up with former jailbird Brown.

A source told Us Weekly previously that matriarch Kris, 58, is no fan of Khloe's relationship with Montana. "Kris thinks he's not right for Khloe," the source said. "She doesn't like that French is supergangster."