Nenjathai Killadhe 2008 one on netflix

A rich boy (Vasan) indulges in various bizarre experiments to have different experiences. He eats in a five star hotel without money, he wears girls’ outfit in a show room, he prefers to go to jail just for the heck of it, and he hires a sex worker and lets her sleep alone…A girl (Aanandhi), daughter of an NRI, staying alone in the city. She is making a documentary film on persons belonging to the fringe world. She meets the convicts in the prison and the sex workers for her documentary. The emotional game between them leads to an unpredictable climax.