Spread (2009)

In Los Angeles, Nikki is homeless, car-less and closing in on 30, but he's amoral, good-looking, and adept in the sack, moving from one wealthy woman of 35 or 40 to another, a kept boy-toy. His newest gig, with Samantha, an attorney whose house overlooks L.A., is sweet, although it's unclear how long she'll put up with him. Then Nikki meets Heather, a waitress. Is the player being played, or might this be love? What will Nikki discover?

Source: TMDb