In this black and white photo shared by Trey Songz, 18-year-old Kendall seemed to be getting pretty close with the 29-year-old "Bottoms Up" singer, while 25-year-old Chris Brown smoked a cigarette with his arm around Kylie, 16.
Kylie and Chris posted a lot more Instagram pics, where the Jenner girls seemed right at home hanging out with some of the more successful rappers in the industry.
This house-party hang should come as no surprise to Kardashian-Jenner fans, as Kendall and Kylie's older sisters are both in relationships with rappers. Kim Kardashian is married to Yeezus artist Kanye West, while Khloe Kardashian is dating rapper French Montana.
Do you think the Jenner sisters are too young to be hanging out with these 20-something rappers?