Secretary (2002)

Dominant boy meets submissive girl in the sorta sweet, sorta disturbing, erotic flick Secretary (2002). Maggie Gyllenhaal is a slightly screwy girl named Lee, who, fresh out of the mental hospital and looking to be a productive member of society, takes a job as the secretary at the firm of neurotic lawyer E. Edward Grey (James Spader). In this office, all correspondence are done by typewriter, which gives Spader plenty of opportunities to punish his secretaries for errors. Yes, it ends up Maggie is just his type, and soon enough the two discover they really like to roleplay as master and slave, while trying out all sorts of BDSM. Mr. Grey (yes we know, but this one came first) feels conflicted about how much he's into Lee and the unusual sex games they play, so since he won't commit, she has go get a normal boyfriend named Peter (Jeremy Davies), who eventually proposes to her. This one's ending is wild. Lee leaves the loser, and is commanded to sit in a chair and not leave. Days pass with her family, then the news media begging her to get up, but she won't until Grey tells her it's okay. Talk about commitment. There's a decent shot of Amy Locane in a pink bikini, but this flick was made by Miss Gyllenhaal showing it all! Lee likes the spanky before the hanky panky, and at one point we see her pull down her granny panties to look at the bruise all that action has resulted in. She tries to do it herself, but it's not the same, so on top of pleasuring herself on company time in the bathroom, we see this dime pull down her panties and offer her ass to Edward Grey. Eventually he takes the offer, and we get to see all three of Maggie's B's as James Spader bathes her and eventually lays her. Everyone loves a fling with the girl that does the filing, but this much sex is ridiculous! You'll have a good jerk, then start thinking about hiring a clerk after watching Secretary.