4. Maggie Gyllenhaal
The movie Secretary (2002) makes the boss-secretary fantasies come true. Maggie Gyllenhaal portrayed the secretary, Lee Holloway.
Lee is a young woman who was recently released from a mental hospital. She gets a job as a secretary to a demanding lawyer, portrayed by James Spader. Their employer-employee relationship turns into a sexual sadomasochistic one.
Lee couldn’t stop thinking about her boss. She pleasured herself thinking of him. It was intense and dramatic. It has been one of the most believable masturbation scenes in movies.
Maggie Gyllenhaal is Jake Gyllenhaal’s sister. Both of them have been successful in the Hollywood world. Maggie also starred Christopher Nolan’s Batman The Dark Knight.
